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Serine

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532: 352: 104: 118: 1015: 55: 1278:-serine, sometimes combined with glycine. Response to treatment is variable and the long-term and functional outcome is unknown. To provide a basis for improving the understanding of the epidemiology, genotype/phenotype correlation and outcome of these diseases their impact on the quality of life of patients, as well as for evaluating diagnostic and therapeutic strategies a patient registry was established by the noncommercial 1078: 75: 964: 2928: 826: 1851:
D-Serine is more potent than glycine as a coagonist at the NMDA receptor, has a regional distribution in the brain that is similar to that of NMDA receptors and appears to be more closely associated with synaptic NMDA receptors than glycine (which is more closely associated with non-synaptic NMDA
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These enzyme defects lead to severe neurological symptoms such as congenital microcephaly and severe psychomotor retardation and in addition, in patients with 3-phosphoglycerate dehydrogenase deficiency to intractable seizures. These symptoms respond to a variable degree to treatment with
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D-Serine is functionally a more potent activator of synaptic NMDARs than glycine, and mounting evidence suggests that it serves as the major NMDAR co-agonist in limbic brain regions implicated in neuropsychiatric
4736: 1279: 4756: 7979: 3241: 1305:-serine as a non-essential amino acid has come to be considered as conditional, since vertebrates such as humans cannot always synthesize optimal quantities over entire lifespans. Safety of 6753: 4729: 6787: 1766:
Liu Y, Hill RH, Arhem P, von Euler G (2001). "NMDA and glycine regulate the affinity of the Mg2+-block site in NR1-1a/NR2A NMDA receptor channels expressed in Xenopus oocytes".
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Madeira C, Lourenco MV, Vargas-Lopes C, Suemoto CK, Brandão CO, Reis T, Leite RE, Laks J, Jacob-Filho W, Pasqualucci CA, Grinberg LT, Ferreira ST, Panizzutti R (May 5, 2015).
7972: 6746: 2884: 7945: 7711: 4722: 3234: 1676: 1709: 7965: 1184:-serine is a more potent agonist at the NMDAR glycine site than glycine itself. However, D-serine has been shown to work as an antagonist/inverse co-agonist of 1927:"Triheteromeric N-methyl-D-aspartate receptors differentiate synaptic inputs onto pyramidal neurons in somatosensory cortex: involvement of the GluN3A subunit" 3227: 585: 7934: 4010: 1257: 2303:
Tabatabaie L, Klomp LW, Berger R, de Koning TJ (March 2010). "L-Serine synthesis in the central nervous system: a review on serine deficiency disorders".
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Takarada T, Hinoi E, Takahata Y, Yoneda Y (May 2008). "Serine racemase suppresses chondrogenic differentiation in cartilage in a Sox9-dependent manner".
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amino acid. It can be synthesized in the human body under normal physiological circumstances, making it a nonessential amino acid. It is encoded by the
6780: 5805: 2877: 1313:, patients (ClinicalTrials.gov identifier: NCT01835782), but treatment of ALS symptoms has yet to be shown. A 2011 meta-analysis found adjunctive 3177: 2260: 229: 5837: 3436: 1604: 7410: 5426: 6773: 4128: 3749: 3340: 5745: 3345: 2407:"The non-protein amino acid BMAA is misincorporated into human proteins in place of L-serine causing protein misfolding and aggregation" 7398: 8509: 8494: 6674: 5501: 2870: 2464:
Levine TD, Miller RG, Bradley WG, Moore DH, Saperstein DS, Flynn LE, Katz JS, Forshew DA, Metcalf JS, Banack SA, Cox PA (2017-01-02).
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Metcalf JS, Dunlop RA, Powell JT, Banack SA, Cox PA (2017). "L-Serine: a Naturally-Occurring Amino Acid with Therapeutic Potential".
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Ghasemi M, Rezania F, Lewin J, Moore KP, Mani AR (Jun 2010). "D-Serine modulates neurogenic relaxation in rat corpus cavernosum".
8095: 2625:"Multiple risk pathways for schizophrenia converge in serine racemase knockout mice, a mouse model of NMDA receptor hypofunction" 1290: 8524: 8504: 8499: 4003: 3571: 2521:
Singh SP, Singh V (Oct 2011). "Meta-analysis of the efficacy of adjunctive NMDA receptor modulators in chronic schizophrenia".
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amino acid discovered to naturally exist in humans, present as a signaling molecule in the brain, soon after the discovery of
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of probable AD patients. D-serine, which is made in the brain, has been shown to work as an antagonist/inverse co-agonist of
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Kawai M, Sekine-Hayakawa Y, Okiyama A, Ninomiya Y (Dec 2012). "Gustatory sensation of L- and D-amino acids in humans".
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Karlheinz Drauz, Ian Grayson, Axel Kleemann, Hans-Peter Krimmer, Wolfgang Leuchtenberger, Christoph Weckbecker (2006).
6034: 3908: 3441: 1082: 509: 1180:-serine must bind to it; in addition a pore blocker must not be bound (e.g. Mg or Zn). Some research has shown that 8489: 7568: 5827: 3996: 2857: 1703: 922: 701: 1309:-serine has been demonstrated in an FDA-approved human phase I clinical trial with Amyotrophic Lateral Sclerosis, 1225:-serine plays a signaling role in peripheral tissues and organs such as cartilage, kidney, and corpus cavernosum. 74: 8226: 8002: 7402: 4515: 4202: 4133: 3797: 3705: 3431: 3380: 3355: 2951: 2731:
Beesley S, Sullenberger T, Crotty K, Ailani R, D'Orio C, Evans K, Ogunkunle EO, Roper MG, Kumar SS (2020-10-02).
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amino acids been discovered in humans sooner, the glycine site on the NMDA receptor might instead be named the
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to have a medium effect size for negative and total symptoms of schizophrenia. There also is evidence that
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Wang J, Serratrice N, Lee CJ, François F, Sweedler JV, Puel JL, Mothet JP, Ruel J (17 December 2021).
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these enzymes are encoded by the genes serA (EC 1.1.1.95), serC (EC 2.6.1.52), and serB (EC 3.1.3.3).
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Mothet JP, Parent AT, Wolosker H, Brady RO, Linden DJ, Ferris CD, Rogawski MA, Snyder SH (Apr 2000).
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Besides disruption of serine biosynthesis, its transport may also become disrupted. One example is
983: 918: 165: 124: 8035: 7548: 7544: 7540: 7532: 5511: 8439: 8368: 8358: 8121: 8070: 8065: 7994: 7841: 7836: 7826: 7732: 6984: 6799: 6654: 5987: 5982: 5905: 5822: 5677: 5666: 5496: 4748: 4467: 4308: 4287: 4236: 3375: 2943: 2546: 2503: 2387: 2285: 2240: 2117: 1962: 891: 724: 8176: 8111: 8045: 7791: 6423: 6408: 5940: 5810: 5770: 5113: 3219: 1596: 1589: 1353:-Serine has been theorized as a potential treatment for sensorineural hearing disorders such as 117: 8353: 8276: 8261: 8231: 8186: 8151: 8146: 8085: 8080: 7894: 7776: 7668: 7302: 7155: 6972: 6928: 6659: 6639: 6634: 6591: 6418: 6388: 6079: 5977: 5950: 5900: 5867: 5847: 5842: 5785: 5780: 5765: 5755: 5735: 5730: 5321: 5281: 5229: 4967: 4902: 4892: 4887: 8271: 8236: 8211: 8206: 8141: 8136: 8131: 8075: 7761: 7660: 7341: 7331: 7221: 7139: 7023: 6569: 5935: 5920: 5692: 5687: 5575: 5475: 5371: 5189: 5082: 4277: 4251: 3913: 3871: 3207: 3029: 2837: 2819: 2778: 2760: 2713: 2664: 2623:
Balu DT, Li Y, Puhl MD, Benneyworth MA, Basu AC, Takagi S, Bolshakov VY, Coyle JT (Jun 2013).
2605: 2587: 2538: 2495: 2487: 2446: 2379: 2371: 2322: 2277: 2232: 2197: 2162: 2109: 2074: 2011: 2003: 1954: 1946: 1903: 1885: 1842: 1824: 1783: 1740: 1689: 1654: 1600: 1418: 982:. However, that reaction is reversible, and will convert excess glycine to serine. SHMT is a 810: 8266: 8256: 8246: 8171: 8126: 7899: 7416: 7034: 6455: 6450: 6445: 6440: 5972: 5392: 4867: 8391: 8311: 8201: 8196: 7988: 7602: 7431: 6999: 6995: 6824: 6796: 6124: 5441: 5387: 5165: 5103: 4780: 4681: 4638: 4432: 4019: 3421: 3301: 2827: 2809: 2768: 2752: 2703: 2695: 2654: 2644: 2595: 2577: 2530: 2477: 2436: 2426: 2363: 2314: 2269: 2224: 2189: 2152: 2101: 2064: 2054: 1993: 1938: 1893: 1877: 1832: 1814: 1775: 1748: 1681: 1540: 1473: 1464:"Nomenclature and symbolism for amino acids and peptides (IUPAC-IUB Recommendations 1983)", 955: 690: 617: 62: 8281: 8241: 7756: 5062: 4714: 1202:-serine was thought to exist only in bacteria until relatively recently; it was the second 497: 489: 481: 308: 8514: 8055: 7492: 7336: 7307: 7177: 7039: 7029: 6991: 6624: 6574: 6334: 6254: 6219: 6119: 5955: 5790: 5560: 5470: 5239: 5204: 5037: 4972: 4815: 4633: 3715: 3523: 2305: 1141: 1006: 933: 868:
protein, a particularly rich source, in 1865 by Emil Cramer. Its name is derived from the
292: 1803:"D-Serine: Potential Therapeutic Agent and/or Biomarker in Schizophrenia and Depression?" 300: 192: 184: 7957: 2748: 2640: 2422: 2258:
de Koning TJ (April 2006). "Treatment with amino acids in serine deficiency disorders".
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MacKay MA, Kravtsenyuk M, Thomas R, Mitchell ND, Dursun SM, Baker GB (6 February 2019).
1438: 1241:-Serine is sweet with an additional minor sour taste at medium and high concentrations. 978:(retro-aldol cleavage) from serine, transferring the resulting formalddehyde synthon to 531: 351: 250: 176: 7991: 7879: 7781: 7451: 7371: 7205: 6980: 6938: 6534: 6514: 6279: 6214: 6134: 6114: 5910: 5382: 5311: 5098: 5017: 4695: 4313: 4256: 4221: 4087: 3710: 3350: 3311: 3129: 2832: 2797: 2773: 2732: 2708: 2683: 2659: 2624: 2600: 2565: 2441: 2406: 2157: 2141:-methyl-D-aspartate receptors contribute to sensory activation in the rat renal pelvis" 2136: 1942: 1898: 1865: 1837: 1802: 1014: 787: 733: 2862: 2684:"D-Serine levels in Alzheimer's disease: implications for novel biomarker development" 1779: 1077: 8483: 8424: 7610: 7520: 7467: 7436: 7189: 7109: 7068: 7019: 6976: 6948: 6704: 6699: 6679: 6539: 6504: 6359: 6354: 6344: 6319: 6314: 6249: 6209: 6169: 5750: 5455: 5367: 5306: 5251: 5219: 5078: 5012: 4832: 4805: 4757: 4686: 4613: 4328: 4057: 3895: 3862: 3824: 3682: 3566: 3202: 3123: 3117: 3019: 2550: 2534: 2069: 2030: 1998: 1981: 1647: 1620: 1185: 1173: 1153: 806: 679: 340: 2391: 2289: 2244: 2121: 1966: 7644: 7588: 7580: 7536: 7504: 7114: 7091: 6494: 6324: 6294: 6199: 6164: 6099: 6084: 5862: 5363: 5336: 5291: 5088: 5074: 5042: 4992: 4947: 4667: 4647: 4502: 4369: 4292: 4194: 3933: 3811: 3687: 3518: 3451: 3316: 3306: 3286: 2917: 2507: 1723: 1354: 1249:
Serine deficiency disorders are rare defects in the biosynthesis of the amino acid
1122: 1098: 963: 849: 791: 6840: 4154: 3370: 2482: 2465: 1685: 460: 2431: 444: 8454: 7889: 7806: 7672: 7614: 7606: 7496: 7351: 7272: 7262: 7209: 7159: 7058: 7043: 7015: 6886: 6684: 6669: 6649: 6619: 6549: 6433: 6413: 6403: 6398: 6378: 6339: 6289: 6284: 6269: 6259: 6224: 6174: 6144: 6139: 6129: 6049: 5992: 5945: 5877: 5852: 5800: 5715: 5601: 5539: 5516: 5224: 5209: 5155: 5143: 4957: 4932: 4820: 4795: 4492: 4164: 4067: 3663: 3161: 3094: 2566:"L-serine: a neglected amino acid with a potential therapeutic role in diabetes" 2318: 1731: 1558: 1327:-Serine is being studied in rodents as a potential treatment for schizophrenia. 1106: 857: 767: 452: 2927: 2756: 2629:
Proceedings of the National Academy of Sciences of the United States of America
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Proceedings of the National Academy of Sciences of the United States of America
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in bacteria. It is also the precursor to numerous other metabolites, including
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spastic tetraplegia, thin corpus callosum, and progressive microcephaly
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Tooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
3696: 3277: 3076: 2955: 2733:"D-serine mitigates cell loss associated with temporal lobe epilepsy" 1126: 814: 261: 3988: 1335:(AD) diagnosis, due to a relatively high concentration of it in the 805:
form under biological conditions), and a side chain consisting of a
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Except where otherwise noted, data are given for materials in their
2798:"Physiopathological Relevance of D-Serine in the Mammalian Cochlea" 1331:-Serine also has been described as a potential biomarker for early 418: 410: 7227: 6579: 6004: 5795: 5521: 5331: 4857: 4847: 4401: 4207: 962: 869: 856:
to the human diet, since it is synthesized in the body from other
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International Working Group on Neurotransmitter Related Disorders
7687: 7559: 7232: 6472: 6299: 5885: 5872: 5506: 5326: 5296: 5286: 5199: 5032: 4997: 4987: 4785: 1441:. IUPAC-IUB Joint Commission on Biochemical Nomenclature. 1983. 1289:, a disease caused by mutations that affect the function of the 903: 865: 400: 7961: 6769: 4718: 3992: 3223: 2866: 2466:"Phase I clinical trial of safety of L-serine for ALS patients" 766:
that is used in the biosynthesis of proteins. It contains an α-
7173: 5710: 2031:"D-Serine is an endogenous ligand for the glycine site of the 1310: 2470:
Amyotrophic Lateral Sclerosis and Frontotemporal Degeneration
1509:(I will describe the body in question by the name "serine".) 1343:-NMDA receptors mitigating neuron loss in an animal model of 555:
InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1
1176:. For the receptor to open, glutamate and either glycine or 514: 116: 102: 73: 53: 1417:(62nd ed.). Boca Raton, FL: CRC Press. p. C-512. 998:-serine is produced from glycine and methanol catalyzed by 2340: 1439:"Nomenclature and Symbolism for Amino Acids and Peptides" 8096: 1253:-serine. At present three disorders have been reported: 1191:
through the glycine binding site on the GluN3 subunit.
1109:. It is the precursor to several amino acids including 8020: 6002:
Uncompetitive pore blockers (mostly dizocilpine site):
1321:‐serine could acquire a therapeutic role in diabetes. 1005:
Racemic serine can be prepared in the laboratory from
8323: 7698: 5408: 8404: 8367: 8344: 8321: 8304: 8094: 8018: 8001: 7855: 7742: 7725: 7696: 6823: 6806: 5406: 5164: 4755: 4660: 4626: 4606: 4599: 4587: 4550: 4543: 4533: 4501: 4410: 4400: 4368: 4348: 4270: 4229: 4220: 4193: 4142: 4116: 4045: 4036: 4026: 3964: 3957: 3931: 3894: 3884: 3861: 3842: 3773: 3739: 3695: 3680: 3648: 3609: 3590: 3556: 3541: 3488: 3473: 3464: 3394: 3330: 3276: 3263: 3103: 3062: 3028: 2995: 2942: 2935: 2900: 1531:-glucosaminic acid, and other oxyamino acids]. 388: 1646: 1588: 1156:, making them able to open if they then also bind 940:-phosphoserine) which is hydrolyzed to serine by 836:-serine (right) in zwitterionic form at neutral pH 2405:Dunlop RA, Cox PA, Banack SA, Rodgers KJ (2013). 1221:-serine site. Apart from central nervous system, 684:246 °C (475 °F; 519 K) decomposes 1595:(3rd ed.). New York: W.H. Freeman. p.  459: 451: 443: 878:. Serine's structure was established in 1902. 565:D/L: Key: MTCFGRXMJLQNBG-UHFFFAOYSA-N 191: 183: 175: 5660: 5645: 1677:Ullmann's Encyclopedia of Industrial Chemistry 1653:(3rd ed.). New York: W. H. Freeman. 1533:Berichte der Deutschen Chemischen Gesellschaft 1152:), serves as a neuromodulator by coactivating 7973: 7857: 7744: 6781: 4730: 4004: 3235: 2878: 2135:Ma MC, Huang HS, Chen YS, Lee SH (Nov 2008). 572:D: Key: MTCFGRXMJLQNBG-UWTATZPHSA-N 8: 1708:: CS1 maint: multiple names: authors list ( 1582: 1580: 1525:-Glucosaminsäure und anderer Oxyaminosäuren" 1258:3-phosphoglycerate dehydrogenase deficiency 886:The biosynthesis of serine starts with the 8369: 8318: 8015: 7980: 7966: 7958: 7739: 6820: 6788: 6774: 6766: 6747:Metabotropic glutamate receptor modulators 4737: 4723: 4715: 4657: 4623: 4603: 4594: 4547: 4540: 4507: 4407: 4374: 4226: 4042: 4033: 4011: 3997: 3989: 3961: 3891: 3692: 3553: 3485: 3470: 3273: 3242: 3228: 3220: 2939: 2885: 2871: 2863: 974:(SMHT) also catalyzes the biosynthesis of 530: 350: 307: 299: 291: 42: 6754:Glutamate metabolism/transport modulators 2831: 2813: 2772: 2707: 2658: 2648: 2599: 2581: 2481: 2440: 2430: 2156: 2068: 2058: 1997: 1897: 1836: 1818: 1268:Phosphoserine aminotransferase deficiency 496: 488: 480: 8101:Tooltip Sphingosine-1-phosphate receptor 7946:Ionotropic glutamate receptor modulators 6825: 5166: 1645:Lehninger AL, Nelson DL, Cox MM (2000). 1076: 1059: 1055: 1051: 1047: 1043: 1039: 1035: 1031: 1495:[On the constituents of silk]. 1392: 1021:Hydrogenation of serine gives the diol 590: 551: 526: 328: 8435:3-Ketosphinganine (dehydrosphingosine) 8025:Tooltip Lysophosphatidic acid receptor 6477:Alcohols/volatile anesthetics/related: 2261:Journal of Inherited Metabolic Disease 1701: 1263:3-phosphoserine phosphatase deficiency 1172:site (NR1) of canonical diheteromeric 341: 8328:Tooltip Serine C-palmitoyltransferase 8157:Dihydro-S1P (sphinganine 1-phosphate) 7703:Tooltip N-Methyl-D-aspartate receptor 5633:Other positive allosteric modulators: 5413:Tooltip N-Methyl-D-aspartate receptor 3437:2-Amino-3-carboxymuconic semialdehyde 1415:CRC Handbook of Chemistry and Physics 852:appears naturally in proteins. It is 786:form under biological conditions), a 558:Key: MTCFGRXMJLQNBG-REOHCLBHSA-N 270: 249: 7: 7395:4-hydroxyquinoline-3-carboxylic acid 7253:4-Phenyl-4-formyl-N-methylpiperidine 3750:2,3-Dihydroxy-3-methylpentanoic acid 7218:trichloroethane (methyl chloroform) 6374:Ifenprodil (NR2B) site antagonists: 2894:Encoded (proteinogenic) amino acids 1864:Wolosker H, Balu DT (9 June 2020). 1493:"Ueber die Bestandtheile der Seide" 1445:from the original on 9 October 2008 1140:-Serine, synthesized in neurons by 921:(transamination) of this ketone by 433: 417: 409: 7822:Pesampator (BIIB-104, PF-04958242) 4938:Pesampator (BIIB-104, PF-04958242) 2802:Frontiers in Cellular Neuroscience 2158:10.1161/HYPERTENSIONAHA.108.114116 1980:Beesley S, Kumar SS (2023-11-01). 1943:10.1016/j.neuroscience.2012.07.020 25: 1085:catalyzes the upper reaction and 864:. Serine was first obtained from 817:UCU, UCC, UCA, UCG, AGU and AGC. 8440:Dihydrosphingosine (sphinganine) 2926: 2535:10.2165/11586650-000000000-00000 1999:10.1016/j.neuropharm.2023.109654 1925:Pilli J, Kumar SS (2012-10-11). 1563:The Columbia Encyclopedia 6th ed 1403:, Oxford, Clarendon Press, 1959. 1291:neutral amino acid transporter A 1081:Cysteine synthesis from serine. 1013: 635: 629: 6414:Rislenemdaz (CERC-301, MK-0657) 5361:Negative allosteric modulators: 5249:Positive allosteric modulators: 5072:Negative allosteric modulators: 4825:Positive allosteric modulators: 3572:Imidazol-4-one-5-propionic acid 1097:in that it participates in the 972:Serine hydroxymethyltransferase 736:(at 25 °C , 100 kPa). 153:2-Amino-3-hydroxypropanoic acid 34:. For the toxic substance, see 30:For the French wine grape, see 5650:Tooltip Dehydroepiandrosterone 4958:Tulrampator (S-47445, CX-1632) 4853:Farampator (CX-691, ORG-24448) 4257:Norepinephrine (noradrenaline) 3386:β-Hydroxy β-methylglutaryl-CoA 3341:β-Hydroxy β-methylbutyric acid 2808:. Frontiers Media SA: 733004. 2094:Journal of Cellular Physiology 908:phosphoglycerate dehydrogenase 714:2.21 (carboxyl), 9.15 (amino) 638: 623: 1: 8470:Receptor/signaling modulators 7921:Receptor/signaling modulators 7862:Tooltip Glycine transporter 2 7772:Bitopertin (RG1678/RO4917838) 7749:Tooltip Glycine transporter 1 6740:Receptor/signaling modulators 6589:Unknown/unsorted antagonists: 5153:Unknown/unsorted antagonists: 4746:Ionotropic glutamate receptor 3601:1-Pyrroline-5-carboxylic acid 3346:β-Hydroxy β-methylbutyryl-CoA 2483:10.1080/21678421.2016.1221971 2035:-methyl-D-aspartate receptor" 1780:10.1016/S0024-3205(01)00975-4 1686:10.1002/14356007.a02_057.pub2 1527:[Synthesis of serine, of 1497:Journal für praktische Chemie 1401:Data for Biochemical Research 1089:catalyzes the lower reaction. 7939:receptor positive modulators 3731:2-Methyl-3-oxopropanoic acid 2564:Holm LJ, Buschard K (2019). 2432:10.1371/journal.pone.0075376 1519:Fischer E, Leuchs H (1902). 1297:Research for therapeutic use 840:This compound is one of the 6438:NR2A-selective antagonists: 5970:Polyamine site antagonists: 5195:Acromelic acid (acromelate) 4781:Acromelic acid (acromelate) 3909:4-Hydroxyphenylpyruvic acid 3442:2-Aminomuconic semialdehyde 2319:10.1016/j.ymgme.2009.10.012 1505:Serine is named on p. 93: 1083:Cystathionine beta synthase 809:group, classifying it as a 98: 49: 8541: 8374:Tooltip Sphingosine kinase 6977:chlorobutanol (chloretone) 4878:Hydrochlorothiazide (HCTZ) 3785:generation of homocysteine 2952:Branched-chain amino acids 2757:10.1038/s41467-020-18757-2 1882:10.1038/s41398-020-00870-x 1649:Principles of Biochemistry 1521:"Synthese des Serins, der 923:phosphoserine transaminase 78:Serine at physiological pH 29: 8510:Glycine receptor agonists 8495:Proteinogenic amino acids 8463: 7912: 7092:pregnenolone (eltanolone) 7069:Glutamic acid (glutamate) 6731: 5820:Glycine site antagonists: 4510: 4377: 4063:Glutamic acid (glutamate) 4058:Aspartic acid (aspartate) 3432:3-Hydroxyanthranilic acid 3155: 2924: 2815:10.3389/fncel.2021.733004 2368:10.1007/s12640-017-9814-x 2274:10.1007/s10545-006-0269-0 2229:10.1007/s00726-012-1315-x 2194:10.1016/j.bcp.2010.02.007 1545:10.1002/cber.190203503213 1087:cystathionine gamma-lyase 942:phosphoserine phosphatase 842:proteinogenic amino acids 730: 723: 718: 664:white crystals or powder 610: 581: 542: 158: 150: 140: 135: 97: 48: 7928:GABA receptor modulators 6830:Tooltip Glycine receptor 5708:Competitive antagonists: 5616:Polyamine site agonists: 5602:Neboglamine (nebostinel) 5171:Tooltip Kainate receptor 4247:Epinephrine (adrenaline) 3919:4-Maleylacetoacetic acid 3726:3-Hydroxyisobutyric acid 3582:Glutamate-1-semialdehyde 2688:Translational Psychiatry 2182:Biochemical Pharmacology 1870:Translational Psychiatry 1820:10.3389/fpsyt.2019.00025 1753:10.15227/orgsyn.020.0081 1399:Dawson, R.M.C., et al., 1000:hydroxymethyltransferase 986:(PLP) dependent enzyme. 980:5,6,7,8-tetrahydrofolate 900:3-phosphohydroxypyruvate 719:Supplementary data page 674:1.603 g/cm (22 °C) 7573:3β-androsterone sulfate 7569:3α-androsterone sulfate 6690:Pentamidine isethionate 6434:Traxoprodil (CP-101606) 5673:Epipregnanolone sulfate 3765:2-Methylacetoacetyl-CoA 3721:3-Hydroxyisobutyryl-CoA 3257:metabolic intermediates 2650:10.1073/pnas.1304308110 1807:Frontiers in Psychiatry 1680:. Weinheim: Wiley-VCH. 1478:10.1351/pac198456050595 1093:Serine is important in 990:Synthesis and reactions 8525:Inhibitory amino acids 8505:NMDA receptor agonists 8500:Glucogenic amino acids 7817:ORG-25935 (SCH-900435) 7006:Alkylbenzene sulfonate 6720:Allosteric modulators: 6655:Ipenoxazone (MLV-6976) 6310:Pethidine (meperidine) 5931:Licostinel (ACEA-1021) 5853:Apimostinel (NRX-1074) 5517:Apimostinel (NRX-1074) 5485:Glycine site agonists: 5317:Licostinel (ACEA-1021) 5028:Licostinel (ACEA-1021) 4913:Mibampator (LY-451395) 4682:Carbonyl sulfide (COS) 4283:N-Methylphenethylamine 3974:Cysteine sulfinic acid 3820:conversion to cysteine 3577:Formiminoglutamic acid 3504:3-Phosphoglyceric acid 3381:β-Methylglutaconyl-CoA 2356:Neurotoxicity Research 2060:10.1073/pnas.97.9.4926 1413:Weast RC, ed. (1981). 1382:Serine octamer cluster 1345:temporal lobe epilepsy 1301:The classification of 1090: 968: 894:(an intermediate from 837: 121: 107: 79: 59: 7890:Opiranserin (VVZ-149) 7190:diethyl ether (ether) 6389:CO-101244 (PD-174494) 6105:Delucemine (NPS-1506) 6055:Alazocine (SKF-10047) 4423:2-AGE (noladin ether) 3706:α-Ketoisovaleric acid 3361:β-Ketoisocaproic acid 3356:α-Ketoisocaproic acid 2737:Nature Communications 1245:Clinical significance 1080: 966: 828: 593:L: C((C(=O)O)N)O 120: 106: 77: 57: 8167:Fingolimod phosphate 7585:pregnenolone sulfate 7565:Neuroactive steroids 7523:constituents (e.g., 7483:Cyanotriphenylborate 7444:Negative modulators: 7367:N,N-Dimethylmuscimol 7293:Cyanotriphenylborate 7130:Tetrahydrocannabinol 7096:pregnenolone acetate 7084:Neuroactive steroids 7057:constituents (e.g., 6966:Positive modulators: 6409:Radiprodil (RGH-896) 6384:Buphenine (nylidrin) 5961:Rapastinel (GLYX-13) 5776:Midafotel (d-CPPene) 5683:Pregnenolone sulfate 5607:Rapastinel (GLYX-13) 5398:Pregnenolone sulfate 5139:Pregnenolone sulfate 4634:Carbon monoxide (CO) 3793:-Adenosyl methionine 3376:β-Methylcrotonyl-CoA 3366:β-Ketoisocaproyl-CoA 3322:β-Hydroxybutyryl-CoA 1472:(5): 595–624, 1984, 1164:-serine is a potent 954:In bacteria such as 111:Ball-and-stick model 7577:deoxycorticosterone 7357:N-Methylbicuculline 5640:-Hydroxycholesterol 5451:Homoquinolinic acid 5424:Main site agonists: 5182:Main site agonists: 4776:5-Fluorowillardiine 4773:Main site agonists: 4639:Hydrogen sulfide (H 4493:Virodhamine (O-AEA) 3966:Cysteine metabolism 3755:2-Methylbutyryl-CoA 3447:2-Aminomuconic acid 3427:3-Hydroxykynurenine 2749:2020NatCo..11.4966B 2641:2013PNAS..110E2400B 2635:(26): E2400–E2409. 2423:2013PLoSO...875376D 2051:2000PNAS...97.4926M 1337:cerebrospinal fluid 1333:Alzheimer's disease 1229:Gustatory sensation 1068:Biological function 984:pyridoxal phosphate 967:Serine biosynthesis 919:Reductive amination 832:-Serine (left) and 691:Solubility in water 656: g·mol 125:Space-filling model 45: 7787:Glycyldodecylamide 7391:4-hydroxyquinoline 7362:N-Methylstrychnine 5988:Diethylenetriamine 5667:prasterone sulfate 5442:Homocysteic acid ( 5185:5-Bromowillardiine 4696:Sulfur dioxide (SO 4607:Cholinergic system 4309:Phenylethanolamine 4288:N-Methyltryptamine 4252:NAS (normelatonin) 4039:inhibitory systems 4037:Major excitatory / 3853:α-Ketobutyric acid 3830:α-Ketobutyric acid 3668:γ-Glutamylcysteine 3412:′-Formylkynurenine 3297:α-Aminoadipic acid 3208:Dehydroamino acids 3168:Encoded (proteins) 3104:Negative charge (p 3063:Positive charge (p 2858:Serine MS Spectrum 2700:10.1038/tp.2015.52 2341:"Patient registry" 2137:"Mechanosensitive 1565:. encyclopedia.com 1091: 1009:in several steps: 969: 892:3-phosphoglycerate 838: 740:Infobox references 725:Serine (data page) 602:: C((C(=O)))O 122: 108: 80: 60: 43: 8490:Alpha-Amino acids 8477: 8476: 8400: 8399: 8315: 8300: 8299: 8012: 7955: 7954: 7908: 7907: 7880:Ethanol (alcohol) 7782:Ethanol (alcohol) 7736: 7721: 7720: 7342:Isonipecotic acid 7248:2-Nitrostrychnine 7243:2-Aminostrychnine 7222:trichloroethylene 7024:sodium thiopental 6981:ethanol (alcohol) 6923: 6915: 6907: 6899: 6871: 6863: 6817: 6763: 6762: 6614: 6570:Trichloroethylene 6515:Ethanol (alcohol) 5880: 5823:4-Cl-KYN (AV-101) 5591: 5583: 5550: 5542: 5534: 5491: 5476:Tetrazolylglycine 5445: 5383:Ethanol (alcohol) 5372:sodium thiopental 5190:5-Iodowillardiine 5099:Ethanol (alcohol) 5083:sodium thiopental 4712: 4711: 4708: 4707: 4656: 4655: 4648:Nitric oxide (NO) 4622: 4621: 4595: 4583: 4582: 4579: 4578: 4529: 4528: 4525: 4524: 4396: 4395: 4392: 4391: 4364: 4363: 4278:3-Iodothyronamine 4216: 4215: 4020:Neurotransmitters 3986: 3985: 3982: 3981: 3953: 3952: 3927: 3926: 3914:Homogentisic acid 3880: 3879: 3872:Methylmalonyl-CoA 3676: 3675: 3537: 3536: 3460: 3459: 3217: 3216: 3178:Non-proteinogenic 3151: 3150: 2583:10.1111/apm.12987 2188:(12): 1791–1796. 2106:10.1002/jcp.21310 1986:Neuropharmacology 1774:(16): 1817–1826. 1704:cite encyclopedia 1606:978-0-7167-1843-7 1587:Stryer L (1988). 1491:Cramer E (1865). 1352: 1330: 1326: 1320: 1308: 1304: 1277: 1252: 1240: 1236: 1224: 1220: 1216: 1210: 1205: 1201: 1183: 1179: 1163: 1147: 1139: 997: 847: 835: 831: 790:(which is in the 770:(which is in the 748:Chemical compound 746: 745: 510:CompTox Dashboard 369:L: 206-130-6 230:Interactive image 218:Interactive image 131: 130: 93: 92: 84: 68: 16:(Redirected from 8532: 8375: 8371: 8329: 8325: 8319: 8309: 8102: 8098: 8026: 8022: 8016: 8006: 7989:Lysophospholipid 7982: 7975: 7968: 7959: 7863: 7859: 7750: 7746: 7740: 7730: 7704: 7700: 7603:dextromethorphan 7493:Dihydropyridines 7432:Thiocolchicoside 7382:Pseudostrychnine 7322:Gaboxadol (THIP) 7316:anandamide (AEA) 7308:Endocannabinoids 7040:Dihydropyridines 7000:trifluoroethanol 6996:trichloroethanol 6921: 6913: 6905: 6897: 6869: 6861: 6831: 6827: 6821: 6811: 6797:Glycine receptor 6790: 6783: 6776: 6767: 6612: 6565:Trichloroethanol 6125:Dextromethorphan 5878: 5662: 5651: 5647: 5589: 5581: 5548: 5540: 5532: 5489: 5443: 5414: 5410: 5172: 5168: 5003:Fanapanel (MPQX) 4763: 4759: 4739: 4732: 4725: 4716: 4687:Nitrous oxide (N 4658: 4627:Gasotransmitters 4624: 4604: 4548: 4541: 4508: 4443:Anandamide (AEA) 4411:Endocannabinoids 4408: 4375: 4262:Serotonin (5-HT) 4227: 4046:Glutamate system 4043: 4034: 4013: 4006: 3999: 3990: 3962: 3892: 3806: 3805: 3693: 3554: 3486: 3471: 3422:Anthranilic acid 3302:2-Oxoadipic acid 3274: 3244: 3237: 3230: 3221: 2940: 2930: 2887: 2880: 2873: 2864: 2846: 2845: 2835: 2817: 2793: 2787: 2786: 2776: 2728: 2722: 2721: 2711: 2679: 2673: 2672: 2662: 2652: 2620: 2614: 2613: 2603: 2585: 2561: 2555: 2554: 2518: 2512: 2511: 2485: 2476:(1–2): 107–111. 2461: 2455: 2454: 2444: 2434: 2402: 2396: 2395: 2351: 2345: 2344: 2337: 2331: 2330: 2300: 2294: 2293: 2255: 2249: 2248: 2223:(6): 2349–2358. 2212: 2206: 2205: 2177: 2171: 2170: 2160: 2132: 2126: 2125: 2089: 2083: 2082: 2072: 2062: 2045:(9): 4926–4931. 2026: 2020: 2019: 2001: 1977: 1971: 1970: 1922: 1916: 1915: 1901: 1861: 1855: 1854: 1840: 1822: 1798: 1792: 1791: 1763: 1757: 1756: 1720: 1714: 1713: 1707: 1699: 1671: 1665: 1664: 1652: 1642: 1636: 1630: 1624: 1617: 1611: 1610: 1594: 1584: 1575: 1574: 1572: 1570: 1555: 1549: 1548: 1539:(3): 3787–3805. 1516: 1510: 1504: 1488: 1482: 1480: 1466:Pure Appl. Chem. 1461: 1455: 1454: 1452: 1450: 1435: 1429: 1428: 1410: 1404: 1397: 1350: 1328: 1324: 1318: 1306: 1302: 1275: 1250: 1238: 1234: 1222: 1218: 1214: 1208: 1203: 1199: 1181: 1177: 1161: 1145: 1137: 1063: 1017: 995: 845: 833: 829: 804: 803: 802: 785: 784: 783: 655: 640: 637: 631: 625: 618:Chemical formula 535: 534: 518: 516: 500: 492: 484: 463: 455: 447: 435: 421: 413: 392: 362: 354: 343: 332: 311: 303: 295: 274: 253: 232: 220: 195: 187: 179: 99: 82: 66: 63:Skeletal formula 58:Skeletal formula 50: 46: 21: 8540: 8539: 8535: 8534: 8533: 8531: 8530: 8529: 8480: 8479: 8478: 8473: 8459: 8445:Dihydroceramide 8396: 8373: 8363: 8340: 8327: 8308: 8296: 8100: 8090: 8041:1-Palmitoyl-LPA 8024: 8005: 7997: 7986: 7956: 7951: 7938: 7904: 7861: 7851: 7762:ALX-5407 (NFPS) 7748: 7729: 7717: 7702: 7692: 7452:Benzodiazepines 7337:Isobutyric acid 7178:chloral hydrate 7030:Chlormethiazole 6992:tribromoethanol 6988:-butanol (2M2P) 6829: 6810: 6802: 6794: 6764: 6759: 6727: 6625:Flufenamic acid 6560:Trichloroethane 6335:Rhynchophylline 6255:Methoxphenidine 6220:Levomilnacipran 6120:Dextromethadone 6045:α-Endopsychosin 5649: 5561:Dimethylglycine 5471:Quinolinic acid 5412: 5402: 5240:Quisqualic acid 5170: 5160: 4816:Quisqualic acid 4761: 4751: 4743: 4713: 4704: 4699: 4690: 4676: 4652: 4642: 4618: 4575: 4521: 4497: 4388: 4360: 4344: 4266: 4222:Biogenic amines 4212: 4189: 4138: 4112: 4038: 4022: 4017: 3987: 3978: 3949: 3923: 3876: 3857: 3838: 3803: 3802: 3769: 3735: 3716:Methacrylyl-CoA 3686: 3672: 3644: 3605: 3586: 3549:α-ketoglutarate 3547: 3533: 3524:Phosphocreatine 3493: 3479: 3456: 3390: 3326: 3259: 3248: 3218: 3213: 3212: 3193:Secondary amino 3147: 3110: 3099: 3069: 3058: 3024: 2991: 2931: 2922: 2896: 2891: 2854: 2849: 2795: 2794: 2790: 2730: 2729: 2725: 2681: 2680: 2676: 2622: 2621: 2617: 2576:(10): 655–659. 2563: 2562: 2558: 2529:(10): 859–885. 2520: 2519: 2515: 2463: 2462: 2458: 2404: 2403: 2399: 2353: 2352: 2348: 2339: 2338: 2334: 2306:Mol Genet Metab 2302: 2301: 2297: 2257: 2256: 2252: 2214: 2213: 2209: 2179: 2178: 2174: 2134: 2133: 2129: 2091: 2090: 2086: 2028: 2027: 2023: 1979: 1978: 1974: 1924: 1923: 1919: 1863: 1862: 1858: 1800: 1799: 1795: 1765: 1764: 1760: 1722: 1721: 1717: 1700: 1696: 1673: 1672: 1668: 1661: 1644: 1643: 1639: 1631: 1627: 1618: 1614: 1607: 1586: 1585: 1578: 1568: 1566: 1557: 1556: 1552: 1518: 1517: 1513: 1490: 1489: 1485: 1463: 1462: 1458: 1448: 1446: 1437: 1436: 1432: 1425: 1412: 1411: 1407: 1398: 1394: 1390: 1367: 1299: 1247: 1231: 1197: 1189:-NMDA receptors 1142:serine racemase 1135: 1075: 1070: 1061: 1057: 1053: 1049: 1045: 1041: 1037: 1033: 1029: 1007:methyl acrylate 992: 934:3-phosphoserine 884: 823: 801: 799: 798: 797: 795: 782: 779: 778: 777: 775: 749: 742: 737: 710: 693: 653: 643: 634: 628: 620: 606: 603: 594: 589: 588: 577: 574: 573: 567: 566: 560: 559: 556: 550: 549: 538: 519: 512: 503: 466: 436: 424: 395: 381: 372: 335: 314: 277: 256: 235: 209: 198: 168: 154: 146: 127: 113: 89: 70: 39: 28: 23: 22: 15: 12: 11: 5: 8538: 8536: 8528: 8527: 8522: 8520:Amino alcohols 8517: 8512: 8507: 8502: 8497: 8492: 8482: 8481: 8475: 8474: 8464: 8461: 8460: 8458: 8457: 8452: 8447: 8442: 8437: 8432: 8427: 8408: 8406: 8402: 8401: 8398: 8397: 8395: 8394: 8389: 8384: 8378: 8376: 8365: 8364: 8362: 8361: 8356: 8350: 8348: 8342: 8341: 8339: 8338: 8332: 8330: 8316: 8302: 8301: 8298: 8297: 8295: 8294: 8285: 8284: 8279: 8274: 8269: 8264: 8259: 8250: 8249: 8244: 8239: 8234: 8229: 8224: 8219: 8214: 8209: 8204: 8199: 8194: 8189: 8184: 8179: 8174: 8169: 8164: 8159: 8154: 8149: 8144: 8139: 8134: 8129: 8124: 8119: 8114: 8105: 8103: 8092: 8091: 8089: 8088: 8083: 8078: 8073: 8068: 8059: 8058: 8053: 8048: 8043: 8038: 8029: 8027: 8013: 7999: 7998: 7987: 7985: 7984: 7977: 7970: 7962: 7953: 7952: 7950: 7949: 7942: 7936: 7931: 7924: 7917: 7913: 7910: 7909: 7906: 7905: 7903: 7902: 7897: 7892: 7887: 7882: 7877: 7872: 7866: 7864: 7853: 7852: 7850: 7849: 7844: 7839: 7834: 7829: 7824: 7819: 7814: 7809: 7804: 7799: 7794: 7789: 7784: 7779: 7774: 7769: 7764: 7759: 7753: 7751: 7737: 7723: 7722: 7719: 7718: 7716: 7715: 7707: 7705: 7694: 7693: 7691: 7690: 7685: 7680: 7658: 7653: 7648: 7634: 7592: 7562: 7557: 7552: 7518: 7513: 7508: 7490: 7485: 7480: 7475: 7449: 7440: 7439: 7434: 7429: 7424: 7419: 7414: 7384: 7379: 7374: 7372:Nipecotic acid 7369: 7364: 7359: 7354: 7349: 7344: 7339: 7334: 7329: 7324: 7319: 7305: 7300: 7295: 7290: 7285: 7280: 7275: 7270: 7265: 7260: 7255: 7250: 7245: 7236: 7235: 7230: 7225: 7206:methoxyflurane 7167: 7137: 7132: 7127: 7122: 7117: 7112: 7107: 7081: 7076: 7071: 7066: 7063:ginsenoside-Rf 7052: 7047: 7037: 7032: 7027: 7013: 7008: 7003: 6962: 6961: 6956: 6951: 6946: 6941: 6939:Picolinic acid 6936: 6931: 6926: 6918: 6910: 6902: 6894: 6889: 6884: 6879: 6874: 6866: 6858: 6853: 6848: 6843: 6834: 6832: 6818: 6804: 6803: 6795: 6793: 6792: 6785: 6778: 6770: 6761: 6760: 6758: 6757: 6750: 6743: 6732: 6729: 6728: 6726: 6725: 6713: 6712: 6702: 6697: 6692: 6687: 6682: 6677: 6672: 6667: 6662: 6657: 6652: 6647: 6642: 6637: 6632: 6627: 6622: 6617: 6609: 6604: 6599: 6594: 6582: 6577: 6572: 6567: 6562: 6557: 6552: 6547: 6542: 6537: 6535:Methoxyflurane 6532: 6527: 6522: 6517: 6512: 6507: 6502: 6497: 6492: 6487: 6482: 6470: 6465: 6453: 6448: 6443: 6431: 6426: 6421: 6416: 6411: 6406: 6401: 6396: 6391: 6386: 6381: 6376: 6367: 6362: 6357: 6352: 6347: 6342: 6337: 6332: 6327: 6322: 6317: 6312: 6307: 6302: 6297: 6292: 6287: 6282: 6280:Nitromemantine 6277: 6272: 6267: 6262: 6257: 6252: 6247: 6242: 6237: 6232: 6227: 6222: 6217: 6215:Levomethorphan 6212: 6207: 6202: 6197: 6192: 6187: 6182: 6177: 6172: 6167: 6162: 6157: 6152: 6147: 6142: 6137: 6135:Dieticyclidine 6132: 6127: 6122: 6117: 6115:Dextrallorphan 6112: 6107: 6102: 6097: 6092: 6087: 6082: 6077: 6072: 6070:Argiotoxin-636 6067: 6062: 6057: 6052: 6047: 6042: 6037: 6032: 6027: 6022: 6017: 6012: 6007: 5995: 5990: 5985: 5983:Diaminopropane 5980: 5975: 5963: 5958: 5953: 5948: 5943: 5938: 5933: 5928: 5923: 5918: 5913: 5911:Kynurenic acid 5908: 5903: 5898: 5893: 5888: 5883: 5875: 5870: 5865: 5860: 5855: 5850: 5845: 5840: 5835: 5830: 5825: 5813: 5808: 5803: 5798: 5793: 5788: 5783: 5778: 5773: 5768: 5763: 5758: 5753: 5748: 5743: 5738: 5733: 5728: 5723: 5718: 5713: 5701: 5700: 5695: 5690: 5685: 5680: 5675: 5670: 5657: 5642: 5626: 5621: 5609: 5604: 5599: 5594: 5586: 5578: 5573: 5568: 5563: 5558: 5553: 5545: 5537: 5529: 5524: 5519: 5514: 5509: 5504: 5499: 5494: 5478: 5473: 5468: 5463: 5458: 5453: 5448: 5439: 5434: 5429: 5417: 5415: 5404: 5403: 5401: 5400: 5395: 5390: 5385: 5380: 5375: 5354: 5349: 5344: 5339: 5334: 5329: 5324: 5319: 5314: 5312:Kynurenic acid 5309: 5304: 5299: 5294: 5289: 5284: 5275: 5274: 5269: 5264: 5259: 5254: 5242: 5237: 5232: 5227: 5222: 5217: 5212: 5207: 5202: 5197: 5192: 5187: 5175: 5173: 5162: 5161: 5159: 5158: 5146: 5141: 5136: 5131: 5126: 5121: 5116: 5111: 5106: 5101: 5096: 5091: 5086: 5065: 5060: 5055: 5050: 5045: 5040: 5035: 5030: 5025: 5020: 5018:Kynurenic acid 5015: 5010: 5005: 5000: 4995: 4990: 4985: 4980: 4975: 4970: 4961: 4960: 4955: 4950: 4945: 4940: 4935: 4930: 4925: 4920: 4915: 4910: 4905: 4900: 4895: 4890: 4885: 4880: 4875: 4870: 4865: 4860: 4855: 4850: 4845: 4840: 4835: 4830: 4818: 4813: 4808: 4803: 4798: 4793: 4788: 4783: 4778: 4766: 4764: 4753: 4752: 4744: 4742: 4741: 4734: 4727: 4719: 4710: 4709: 4706: 4705: 4703: 4702: 4697: 4693: 4688: 4684: 4679: 4674: 4670: 4664: 4662: 4654: 4653: 4651: 4650: 4645: 4640: 4636: 4630: 4628: 4620: 4619: 4617: 4616: 4610: 4608: 4601: 4597: 4596: 4592: 4585: 4584: 4581: 4580: 4577: 4576: 4574: 4573: 4568: 4563: 4557: 4555: 4545: 4538: 4531: 4530: 4527: 4526: 4523: 4522: 4520: 4519: 4511: 4505: 4499: 4498: 4496: 4495: 4490: 4485: 4480: 4475: 4470: 4465: 4460: 4455: 4450: 4445: 4440: 4435: 4430: 4425: 4420: 4414: 4412: 4405: 4398: 4397: 4394: 4393: 4390: 4389: 4387: 4386: 4378: 4372: 4366: 4365: 4362: 4361: 4359: 4358: 4352: 4350: 4346: 4345: 4343: 4342: 4334: 4326: 4321: 4316: 4314:Phenethylamine 4311: 4306: 4298: 4290: 4285: 4280: 4274: 4272: 4268: 4267: 4265: 4264: 4259: 4254: 4249: 4244: 4239: 4233: 4231: 4224: 4218: 4217: 4214: 4213: 4211: 4210: 4205: 4199: 4197: 4191: 4190: 4188: 4187: 4182: 4177: 4172: 4167: 4162: 4157: 4152: 4146: 4144: 4143:Glycine system 4140: 4139: 4137: 4136: 4131: 4126: 4120: 4118: 4114: 4113: 4111: 4110: 4105: 4100: 4095: 4090: 4088:Kynurenic acid 4085: 4080: 4075: 4070: 4065: 4060: 4055: 4049: 4047: 4040: 4031: 4024: 4023: 4018: 4016: 4015: 4008: 4001: 3993: 3984: 3983: 3980: 3979: 3977: 3976: 3970: 3968: 3959: 3955: 3954: 3951: 3950: 3948: 3947: 3938: 3936: 3929: 3928: 3925: 3924: 3922: 3921: 3916: 3911: 3905: 3903: 3889: 3882: 3881: 3878: 3877: 3875: 3874: 3868: 3866: 3859: 3858: 3856: 3855: 3849: 3847: 3840: 3839: 3837: 3836: 3827: 3815: 3814: 3809: 3795: 3780: 3778: 3771: 3770: 3768: 3767: 3762: 3757: 3752: 3746: 3744: 3737: 3736: 3734: 3733: 3728: 3723: 3718: 3713: 3711:Isobutyryl-CoA 3708: 3702: 3700: 3690: 3678: 3677: 3674: 3673: 3671: 3670: 3652: 3650: 3646: 3645: 3643: 3642: 3637: 3632: 3627: 3622: 3616: 3614: 3607: 3606: 3604: 3603: 3597: 3595: 3588: 3587: 3585: 3584: 3579: 3574: 3569: 3563: 3561: 3551: 3539: 3538: 3535: 3534: 3532: 3531: 3526: 3521: 3507: 3506: 3500: 3498: 3483: 3468: 3462: 3461: 3458: 3457: 3455: 3454: 3449: 3444: 3439: 3434: 3429: 3424: 3419: 3414: 3405: 3403: 3392: 3391: 3389: 3388: 3383: 3378: 3373: 3368: 3363: 3358: 3353: 3351:Isovaleryl-CoA 3348: 3343: 3337: 3335: 3328: 3327: 3325: 3324: 3319: 3314: 3312:Glutaconyl-CoA 3309: 3304: 3299: 3294: 3289: 3283: 3281: 3271: 3261: 3260: 3249: 3247: 3246: 3239: 3232: 3224: 3215: 3214: 3211: 3210: 3205: 3200: 3195: 3190: 3185: 3180: 3175: 3170: 3157: 3156: 3153: 3152: 3149: 3148: 3146: 3145: 3139: 3133: 3130:Selenocysteine 3127: 3121: 3114: 3112: 3108: 3101: 3100: 3098: 3097: 3092: 3086: 3080: 3073: 3071: 3067: 3060: 3059: 3057: 3056: 3051: 3046: 3041: 3035: 3033: 3026: 3025: 3023: 3022: 3017: 3012: 3007: 3001: 2999: 2993: 2992: 2990: 2989: 2984: 2979: 2974: 2969: 2963: 2958: 2948: 2946: 2937: 2933: 2932: 2925: 2923: 2921: 2920: 2915: 2910: 2904: 2902: 2901:General topics 2898: 2897: 2892: 2890: 2889: 2882: 2875: 2867: 2861: 2860: 2853: 2852:External links 2850: 2848: 2847: 2788: 2723: 2674: 2615: 2556: 2513: 2456: 2397: 2362:(1): 213–221. 2346: 2332: 2313:(3): 256–262. 2295: 2268:(2): 347–351. 2250: 2207: 2172: 2151:(5): 938–944. 2127: 2100:(2): 320–328. 2084: 2021: 1972: 1917: 1856: 1793: 1758: 1715: 1695:978-3527306732 1694: 1666: 1659: 1637: 1625: 1612: 1605: 1576: 1550: 1511: 1483: 1456: 1430: 1423: 1405: 1391: 1389: 1386: 1385: 1384: 1379: 1378:(isothreonine) 1373: 1366: 1363: 1298: 1295: 1271: 1270: 1265: 1260: 1246: 1243: 1230: 1227: 1196: 1193: 1174:NMDA receptors 1154:NMDA receptors 1134: 1131: 1074: 1071: 1069: 1066: 1065: 1064: 1019: 1018: 994:Industrially, 991: 988: 883: 880: 822: 819: 800: 788:carboxyl group 780: 747: 744: 743: 738: 734:standard state 731: 728: 727: 721: 720: 716: 715: 712: 708: 698: 697: 694: 689: 686: 685: 682: 676: 675: 672: 666: 665: 662: 658: 657: 651: 645: 644: 641: 632: 626: 621: 616: 613: 612: 608: 607: 605: 604: 597: 595: 592: 584: 583: 582: 579: 578: 576: 575: 571: 570: 568: 564: 563: 561: 557: 554: 553: 545: 544: 543: 540: 539: 537: 536: 528:DTXSID60883230 522: 520: 508: 505: 504: 502: 501: 493: 485: 476: 474: 468: 467: 465: 464: 456: 448: 439: 437: 429: 426: 425: 423: 422: 414: 405: 403: 397: 396: 394: 393: 384: 382: 377: 374: 373: 371: 370: 366: 364: 356: 355: 345: 337: 336: 334: 333: 324: 322: 316: 315: 313: 312: 304: 296: 287: 285: 279: 278: 276: 275: 266: 264: 258: 257: 255: 254: 245: 243: 237: 236: 234: 233: 221: 212: 210: 203: 200: 199: 197: 196: 188: 180: 171: 169: 164: 161: 160: 156: 155: 152: 148: 147: 144: 138: 137: 133: 132: 129: 128: 123: 114: 109: 95: 94: 91: 90: 81: 71: 61: 26: 24: 14: 13: 10: 9: 6: 4: 3: 2: 8537: 8526: 8523: 8521: 8518: 8516: 8513: 8511: 8508: 8506: 8503: 8501: 8498: 8496: 8493: 8491: 8488: 8487: 8485: 8472: 8471: 8468: 8462: 8456: 8453: 8451: 8448: 8446: 8443: 8441: 8438: 8436: 8433: 8431: 8428: 8426: 8425:Palmitoyl-CoA 8423: 8419: 8416: 8413: 8410: 8409: 8407: 8403: 8393: 8390: 8388: 8385: 8383: 8380: 8379: 8377: 8372: 8366: 8360: 8357: 8355: 8352: 8351: 8349: 8347: 8343: 8337: 8334: 8333: 8331: 8326: 8320: 8317: 8313: 8307: 8303: 8293: 8290: 8287: 8286: 8283: 8280: 8278: 8275: 8273: 8270: 8268: 8265: 8263: 8260: 8258: 8255: 8252: 8251: 8248: 8245: 8243: 8240: 8238: 8235: 8233: 8230: 8228: 8225: 8223: 8220: 8218: 8215: 8213: 8210: 8208: 8205: 8203: 8200: 8198: 8195: 8193: 8190: 8188: 8185: 8183: 8180: 8178: 8175: 8173: 8170: 8168: 8165: 8163: 8160: 8158: 8155: 8153: 8150: 8148: 8145: 8143: 8140: 8138: 8135: 8133: 8130: 8128: 8125: 8123: 8120: 8118: 8115: 8113: 8110: 8107: 8106: 8104: 8099: 8093: 8087: 8084: 8082: 8079: 8077: 8074: 8072: 8069: 8067: 8064: 8061: 8060: 8057: 8054: 8052: 8049: 8047: 8044: 8042: 8039: 8037: 8034: 8031: 8030: 8028: 8023: 8017: 8014: 8010: 8004: 8000: 7996: 7993: 7990: 7983: 7978: 7976: 7971: 7969: 7964: 7963: 7960: 7948: 7947: 7943: 7941: 7940: 7932: 7930: 7929: 7925: 7923: 7922: 7918: 7915: 7914: 7911: 7901: 7898: 7896: 7893: 7891: 7888: 7886: 7883: 7881: 7878: 7876: 7873: 7871: 7868: 7867: 7865: 7860: 7854: 7848: 7845: 7843: 7840: 7838: 7835: 7833: 7830: 7828: 7825: 7823: 7820: 7818: 7815: 7813: 7810: 7808: 7805: 7803: 7800: 7798: 7795: 7793: 7790: 7788: 7785: 7783: 7780: 7778: 7775: 7773: 7770: 7768: 7765: 7763: 7760: 7758: 7755: 7754: 7752: 7747: 7741: 7738: 7734: 7728: 7724: 7713: 7709: 7708: 7706: 7701: 7695: 7689: 7686: 7684: 7681: 7678: 7674: 7670: 7666: 7662: 7659: 7657: 7654: 7652: 7649: 7646: 7642: 7638: 7635: 7632: 7628: 7624: 7620: 7616: 7612: 7611:levomethadone 7608: 7604: 7600: 7596: 7593: 7590: 7586: 7582: 7578: 7574: 7570: 7566: 7563: 7561: 7558: 7556: 7553: 7550: 7546: 7542: 7538: 7534: 7530: 7526: 7522: 7519: 7517: 7514: 7512: 7509: 7506: 7502: 7498: 7494: 7491: 7489: 7486: 7484: 7481: 7479: 7476: 7473: 7469: 7468:flunitrazepam 7465: 7461: 7457: 7453: 7450: 7448: 7445: 7442: 7441: 7438: 7435: 7433: 7430: 7428: 7425: 7423: 7420: 7418: 7415: 7412: 7408: 7404: 7400: 7396: 7392: 7388: 7385: 7383: 7380: 7378: 7375: 7373: 7370: 7368: 7365: 7363: 7360: 7358: 7355: 7353: 7350: 7348: 7347:Isostrychnine 7345: 7343: 7340: 7338: 7335: 7333: 7330: 7328: 7325: 7323: 7320: 7317: 7313: 7309: 7306: 7304: 7301: 7299: 7296: 7294: 7291: 7289: 7286: 7284: 7281: 7279: 7276: 7274: 7271: 7269: 7266: 7264: 7261: 7259: 7256: 7254: 7251: 7249: 7246: 7244: 7241: 7238: 7237: 7234: 7231: 7229: 7226: 7223: 7219: 7215: 7211: 7207: 7203: 7199: 7195: 7191: 7187: 7183: 7179: 7175: 7171: 7168: 7165: 7161: 7157: 7153: 7149: 7145: 7141: 7138: 7136: 7133: 7131: 7128: 7126: 7123: 7121: 7118: 7116: 7113: 7111: 7110:Nitrous oxide 7108: 7105: 7101: 7097: 7093: 7089: 7085: 7082: 7080: 7077: 7075: 7072: 7070: 7067: 7064: 7060: 7056: 7053: 7051: 7048: 7045: 7041: 7038: 7036: 7033: 7031: 7028: 7025: 7021: 7020:pentobarbital 7017: 7014: 7012: 7009: 7007: 7004: 7001: 6997: 6993: 6989: 6987: 6982: 6978: 6974: 6970: 6967: 6964: 6963: 6960: 6957: 6955: 6952: 6950: 6949:Quisqualamine 6947: 6945: 6942: 6940: 6937: 6935: 6932: 6930: 6927: 6925: 6919: 6917: 6911: 6909: 6903: 6901: 6895: 6893: 6890: 6888: 6885: 6883: 6880: 6878: 6875: 6873: 6867: 6865: 6859: 6857: 6854: 6852: 6849: 6847: 6844: 6842: 6839: 6836: 6835: 6833: 6828: 6822: 6819: 6815: 6809: 6805: 6801: 6798: 6791: 6786: 6784: 6779: 6777: 6772: 6771: 6768: 6756: 6755: 6751: 6749: 6748: 6744: 6742: 6741: 6738: 6734: 6733: 6730: 6724: 6721: 6718: 6715: 6714: 6710: 6706: 6705:Transcrocetin 6703: 6701: 6700:Psychotridine 6698: 6696: 6693: 6691: 6688: 6686: 6683: 6681: 6680:Niflumic acid 6678: 6676: 6673: 6671: 6668: 6666: 6663: 6661: 6658: 6656: 6653: 6651: 6648: 6646: 6643: 6641: 6638: 6636: 6633: 6631: 6628: 6626: 6623: 6621: 6618: 6616: 6610: 6608: 6605: 6603: 6600: 6598: 6595: 6593: 6590: 6586: 6583: 6581: 6578: 6576: 6573: 6571: 6568: 6566: 6563: 6561: 6558: 6556: 6553: 6551: 6548: 6546: 6543: 6541: 6540:Nitrous oxide 6538: 6536: 6533: 6531: 6528: 6526: 6523: 6521: 6518: 6516: 6513: 6511: 6508: 6506: 6505:Diethyl ether 6503: 6501: 6498: 6496: 6493: 6491: 6488: 6486: 6483: 6481: 6478: 6474: 6471: 6469: 6466: 6464: 6461: 6457: 6454: 6452: 6449: 6447: 6444: 6442: 6439: 6435: 6432: 6430: 6427: 6425: 6422: 6420: 6417: 6415: 6412: 6410: 6407: 6405: 6402: 6400: 6397: 6395: 6392: 6390: 6387: 6385: 6382: 6380: 6377: 6375: 6371: 6368: 6366: 6363: 6361: 6360:Tenocyclidine 6358: 6356: 6355:Tabernanthine 6353: 6351: 6348: 6346: 6345:Rolicyclidine 6343: 6341: 6338: 6336: 6333: 6331: 6328: 6326: 6323: 6321: 6320:Phencyclidine 6318: 6316: 6315:Phencyclamine 6313: 6311: 6308: 6306: 6303: 6301: 6298: 6296: 6293: 6291: 6288: 6286: 6283: 6281: 6278: 6276: 6273: 6271: 6268: 6266: 6263: 6261: 6258: 6256: 6253: 6251: 6250:Methoxetamine 6248: 6246: 6243: 6241: 6238: 6236: 6233: 6231: 6228: 6226: 6223: 6221: 6218: 6216: 6213: 6211: 6210:Levomethadone 6208: 6206: 6203: 6201: 6198: 6196: 6193: 6191: 6188: 6186: 6183: 6181: 6178: 6176: 6173: 6171: 6170:Fluorolintane 6168: 6166: 6163: 6161: 6158: 6156: 6153: 6151: 6148: 6146: 6143: 6141: 6138: 6136: 6133: 6131: 6128: 6126: 6123: 6121: 6118: 6116: 6113: 6111: 6108: 6106: 6103: 6101: 6098: 6096: 6093: 6091: 6088: 6086: 6083: 6081: 6078: 6076: 6073: 6071: 6068: 6066: 6063: 6061: 6058: 6056: 6053: 6051: 6048: 6046: 6043: 6041: 6038: 6036: 6033: 6031: 6028: 6026: 6023: 6021: 6018: 6016: 6013: 6011: 6008: 6006: 6003: 5999: 5996: 5994: 5991: 5989: 5986: 5984: 5981: 5979: 5976: 5974: 5971: 5967: 5964: 5962: 5959: 5957: 5954: 5952: 5949: 5947: 5944: 5942: 5939: 5937: 5934: 5932: 5929: 5927: 5924: 5922: 5919: 5917: 5914: 5912: 5909: 5907: 5904: 5902: 5899: 5897: 5894: 5892: 5889: 5887: 5884: 5882: 5876: 5874: 5871: 5869: 5866: 5864: 5861: 5859: 5856: 5854: 5851: 5849: 5846: 5844: 5841: 5839: 5836: 5834: 5831: 5829: 5826: 5824: 5821: 5817: 5814: 5812: 5809: 5807: 5804: 5802: 5799: 5797: 5794: 5792: 5789: 5787: 5784: 5782: 5779: 5777: 5774: 5772: 5769: 5767: 5764: 5762: 5759: 5757: 5754: 5752: 5751:Kaitocephalin 5749: 5747: 5744: 5742: 5739: 5737: 5734: 5732: 5729: 5727: 5724: 5722: 5719: 5717: 5714: 5712: 5709: 5706: 5703: 5702: 5699: 5696: 5694: 5691: 5689: 5686: 5684: 5681: 5679: 5676: 5674: 5671: 5668: 5664: 5658: 5655: 5648: 5643: 5641: 5639: 5634: 5630: 5627: 5625: 5622: 5620: 5617: 5613: 5610: 5608: 5605: 5603: 5600: 5598: 5595: 5593: 5587: 5585: 5579: 5577: 5574: 5572: 5569: 5567: 5564: 5562: 5559: 5557: 5554: 5552: 5546: 5544: 5538: 5536: 5530: 5528: 5525: 5523: 5520: 5518: 5515: 5513: 5510: 5508: 5505: 5503: 5500: 5498: 5495: 5493: 5486: 5482: 5479: 5477: 5474: 5472: 5469: 5467: 5464: 5462: 5459: 5457: 5456:Ibotenic acid 5454: 5452: 5449: 5447: 5440: 5438: 5435: 5433: 5430: 5428: 5425: 5422: 5419: 5418: 5416: 5411: 5405: 5399: 5396: 5394: 5391: 5389: 5386: 5384: 5381: 5379: 5376: 5373: 5369: 5368:pentobarbital 5365: 5362: 5358: 5355: 5353: 5350: 5348: 5345: 5343: 5340: 5338: 5335: 5333: 5330: 5328: 5325: 5323: 5320: 5318: 5315: 5313: 5310: 5308: 5307:Kaitocephalin 5305: 5303: 5300: 5298: 5295: 5293: 5290: 5288: 5285: 5283: 5280: 5277: 5276: 5273: 5270: 5268: 5265: 5263: 5260: 5258: 5255: 5253: 5252:Cyclothiazide 5250: 5246: 5243: 5241: 5238: 5236: 5233: 5231: 5228: 5226: 5223: 5221: 5220:Ibotenic acid 5218: 5216: 5213: 5211: 5208: 5206: 5203: 5201: 5198: 5196: 5193: 5191: 5188: 5186: 5183: 5180: 5177: 5176: 5174: 5169: 5163: 5157: 5154: 5150: 5147: 5145: 5142: 5140: 5137: 5135: 5132: 5130: 5127: 5125: 5122: 5120: 5117: 5115: 5112: 5110: 5107: 5105: 5102: 5100: 5097: 5095: 5092: 5090: 5087: 5084: 5080: 5079:pentobarbital 5076: 5073: 5069: 5066: 5064: 5061: 5059: 5056: 5054: 5051: 5049: 5046: 5044: 5041: 5039: 5036: 5034: 5031: 5029: 5026: 5024: 5021: 5019: 5016: 5014: 5013:Kaitocephalin 5011: 5009: 5006: 5004: 5001: 4999: 4996: 4994: 4991: 4989: 4986: 4984: 4981: 4979: 4976: 4974: 4971: 4969: 4966: 4963: 4962: 4959: 4956: 4954: 4951: 4949: 4946: 4944: 4941: 4939: 4936: 4934: 4931: 4929: 4926: 4924: 4921: 4919: 4916: 4914: 4911: 4909: 4906: 4904: 4901: 4899: 4896: 4894: 4891: 4889: 4886: 4884: 4881: 4879: 4876: 4874: 4871: 4869: 4866: 4864: 4861: 4859: 4856: 4854: 4851: 4849: 4846: 4844: 4841: 4839: 4836: 4834: 4833:Cyclothiazide 4831: 4829: 4826: 4822: 4819: 4817: 4814: 4812: 4809: 4807: 4806:Ibotenic acid 4804: 4802: 4799: 4797: 4794: 4792: 4789: 4787: 4784: 4782: 4779: 4777: 4774: 4771: 4768: 4767: 4765: 4760: 4754: 4750: 4747: 4740: 4735: 4733: 4728: 4726: 4721: 4720: 4717: 4701: 4694: 4692: 4685: 4683: 4680: 4678: 4671: 4669: 4666: 4665: 4663: 4659: 4649: 4646: 4644: 4637: 4635: 4632: 4631: 4629: 4625: 4615: 4614:Acetylcholine 4612: 4611: 4609: 4605: 4602: 4600:Miscellaneous 4598: 4593: 4590: 4586: 4572: 4569: 4567: 4564: 4562: 4559: 4558: 4556: 4553: 4549: 4546: 4542: 4539: 4536: 4532: 4517: 4513: 4512: 4509: 4506: 4504: 4503:Neurosteroids 4500: 4494: 4491: 4489: 4486: 4484: 4481: 4479: 4476: 4474: 4471: 4469: 4466: 4464: 4461: 4459: 4456: 4454: 4451: 4449: 4446: 4444: 4441: 4439: 4436: 4434: 4431: 4429: 4426: 4424: 4421: 4419: 4416: 4415: 4413: 4409: 4406: 4403: 4399: 4384: 4380: 4379: 4376: 4373: 4371: 4370:Neuropeptides 4367: 4357: 4354: 4353: 4351: 4347: 4341: 4339: 4335: 4333: 4331: 4327: 4325: 4322: 4320: 4317: 4315: 4312: 4310: 4307: 4305: 4303: 4299: 4297: 4295: 4291: 4289: 4286: 4284: 4281: 4279: 4276: 4275: 4273: 4269: 4263: 4260: 4258: 4255: 4253: 4250: 4248: 4245: 4243: 4240: 4238: 4235: 4234: 4232: 4228: 4225: 4223: 4219: 4209: 4206: 4204: 4201: 4200: 4198: 4196: 4192: 4186: 4183: 4181: 4178: 4176: 4173: 4171: 4168: 4166: 4163: 4161: 4158: 4156: 4153: 4151: 4148: 4147: 4145: 4141: 4135: 4132: 4130: 4127: 4125: 4122: 4121: 4119: 4115: 4109: 4106: 4104: 4101: 4099: 4096: 4094: 4091: 4089: 4086: 4084: 4081: 4079: 4076: 4074: 4071: 4069: 4066: 4064: 4061: 4059: 4056: 4054: 4051: 4050: 4048: 4044: 4041: 4035: 4032: 4029: 4025: 4021: 4014: 4009: 4007: 4002: 4000: 3995: 3994: 3991: 3975: 3972: 3971: 3969: 3967: 3963: 3960: 3956: 3946: 3945: 3940: 3939: 3937: 3935: 3930: 3920: 3917: 3915: 3912: 3910: 3907: 3906: 3904: 3901: 3897: 3896:phenylalanine 3893: 3890: 3888: 3883: 3873: 3870: 3869: 3867: 3864: 3863:propionyl-CoA 3860: 3854: 3851: 3850: 3848: 3845: 3841: 3835: 3831: 3828: 3826: 3825:Cystathionine 3823: 3821: 3817: 3816: 3813: 3810: 3808: 3807:-homocysteine 3800: 3796: 3794: 3792: 3788: 3786: 3782: 3781: 3779: 3776: 3772: 3766: 3763: 3761: 3758: 3756: 3753: 3751: 3748: 3747: 3745: 3742: 3738: 3732: 3729: 3727: 3724: 3722: 3719: 3717: 3714: 3712: 3709: 3707: 3704: 3703: 3701: 3698: 3694: 3691: 3689: 3684: 3683:propionyl-CoA 3679: 3669: 3665: 3661: 3657: 3654: 3653: 3651: 3647: 3641: 3638: 3636: 3633: 3631: 3628: 3626: 3623: 3621: 3618: 3617: 3615: 3612: 3608: 3602: 3599: 3598: 3596: 3593: 3589: 3583: 3580: 3578: 3575: 3573: 3570: 3568: 3567:Urocanic acid 3565: 3564: 3562: 3559: 3555: 3552: 3550: 3545: 3540: 3530: 3527: 3525: 3522: 3520: 3516: 3512: 3509: 3508: 3505: 3502: 3501: 3499: 3496: 3491: 3487: 3484: 3482: 3477: 3472: 3469: 3467: 3463: 3453: 3450: 3448: 3445: 3443: 3440: 3438: 3435: 3433: 3430: 3428: 3425: 3423: 3420: 3418: 3415: 3413: 3411: 3407: 3406: 3404: 3401: 3397: 3393: 3387: 3384: 3382: 3379: 3377: 3374: 3372: 3369: 3367: 3364: 3362: 3359: 3357: 3354: 3352: 3349: 3347: 3344: 3342: 3339: 3338: 3336: 3333: 3329: 3323: 3320: 3318: 3315: 3313: 3310: 3308: 3305: 3303: 3300: 3298: 3295: 3293: 3290: 3288: 3285: 3284: 3282: 3279: 3275: 3272: 3270: 3266: 3262: 3258: 3255: 3252: 3245: 3240: 3238: 3233: 3231: 3226: 3225: 3222: 3209: 3206: 3204: 3203:D-amino acids 3201: 3199: 3196: 3194: 3191: 3189: 3186: 3184: 3181: 3179: 3176: 3174: 3171: 3169: 3165: 3163: 3159: 3158: 3154: 3143: 3140: 3137: 3134: 3131: 3128: 3125: 3124:Glutamic acid 3122: 3119: 3118:Aspartic acid 3116: 3115: 3113: 3107: 3102: 3096: 3093: 3090: 3087: 3084: 3081: 3078: 3075: 3074: 3072: 3066: 3061: 3055: 3052: 3050: 3047: 3045: 3042: 3040: 3037: 3036: 3034: 3031: 3027: 3021: 3020:Phenylalanine 3018: 3016: 3013: 3011: 3008: 3006: 3003: 3002: 3000: 2998: 2994: 2988: 2985: 2983: 2980: 2978: 2975: 2973: 2970: 2967: 2964: 2962: 2959: 2957: 2953: 2950: 2949: 2947: 2945: 2941: 2938: 2936:By properties 2934: 2929: 2919: 2916: 2914: 2911: 2909: 2906: 2905: 2903: 2899: 2895: 2888: 2883: 2881: 2876: 2874: 2869: 2868: 2865: 2859: 2856: 2855: 2851: 2843: 2839: 2834: 2829: 2825: 2821: 2816: 2811: 2807: 2803: 2799: 2792: 2789: 2784: 2780: 2775: 2770: 2766: 2762: 2758: 2754: 2750: 2746: 2742: 2738: 2734: 2727: 2724: 2719: 2715: 2710: 2705: 2701: 2697: 2693: 2689: 2685: 2678: 2675: 2670: 2666: 2661: 2656: 2651: 2646: 2642: 2638: 2634: 2630: 2626: 2619: 2616: 2611: 2607: 2602: 2597: 2593: 2589: 2584: 2579: 2575: 2571: 2567: 2560: 2557: 2552: 2548: 2544: 2540: 2536: 2532: 2528: 2524: 2517: 2514: 2509: 2505: 2501: 2497: 2493: 2489: 2484: 2479: 2475: 2471: 2467: 2460: 2457: 2452: 2448: 2443: 2438: 2433: 2428: 2424: 2420: 2417:(9): e75376. 2416: 2412: 2408: 2401: 2398: 2393: 2389: 2385: 2381: 2377: 2373: 2369: 2365: 2361: 2357: 2350: 2347: 2342: 2336: 2333: 2328: 2324: 2320: 2316: 2312: 2308: 2307: 2299: 2296: 2291: 2287: 2283: 2279: 2275: 2271: 2267: 2263: 2262: 2254: 2251: 2246: 2242: 2238: 2234: 2230: 2226: 2222: 2218: 2211: 2208: 2203: 2199: 2195: 2191: 2187: 2183: 2176: 2173: 2168: 2164: 2159: 2154: 2150: 2146: 2142: 2140: 2131: 2128: 2123: 2119: 2115: 2111: 2107: 2103: 2099: 2095: 2088: 2085: 2080: 2076: 2071: 2066: 2061: 2056: 2052: 2048: 2044: 2040: 2036: 2034: 2025: 2022: 2017: 2013: 2009: 2005: 2000: 1995: 1991: 1987: 1983: 1976: 1973: 1968: 1964: 1960: 1956: 1952: 1948: 1944: 1940: 1936: 1932: 1928: 1921: 1918: 1914: 1909: 1905: 1900: 1895: 1891: 1887: 1883: 1879: 1875: 1871: 1867: 1860: 1857: 1853: 1848: 1844: 1839: 1834: 1830: 1826: 1821: 1816: 1812: 1808: 1804: 1797: 1794: 1789: 1785: 1781: 1777: 1773: 1769: 1768:Life Sciences 1762: 1759: 1754: 1750: 1746: 1743: 1742: 1737: 1735: 1729: 1725: 1719: 1716: 1711: 1705: 1697: 1691: 1687: 1683: 1679: 1678: 1670: 1667: 1662: 1660:1-57259-153-6 1656: 1651: 1650: 1641: 1638: 1635: 1629: 1626: 1622: 1616: 1613: 1608: 1602: 1598: 1593: 1592: 1583: 1581: 1577: 1564: 1560: 1554: 1551: 1546: 1542: 1538: 1535:(in German). 1534: 1530: 1526: 1524: 1515: 1512: 1508: 1502: 1499:(in German). 1498: 1494: 1487: 1484: 1479: 1475: 1471: 1467: 1460: 1457: 1444: 1440: 1434: 1431: 1426: 1424:0-8493-0462-8 1420: 1416: 1409: 1406: 1402: 1396: 1393: 1387: 1383: 1380: 1377: 1374: 1372: 1369: 1368: 1364: 1362: 1360: 1356: 1348: 1346: 1342: 1338: 1334: 1322: 1316: 1312: 1296: 1294: 1292: 1288: 1283: 1281: 1269: 1266: 1264: 1261: 1259: 1256: 1255: 1254: 1244: 1242: 1228: 1226: 1212: 1194: 1192: 1190: 1188: 1175: 1171: 1167: 1159: 1155: 1151: 1148:-serine (its 1143: 1132: 1130: 1128: 1124: 1123:sphingolipids 1120: 1117:, as well as 1116: 1112: 1108: 1104: 1100: 1096: 1088: 1084: 1079: 1072: 1067: 1028: 1027: 1026: 1024: 1016: 1012: 1011: 1010: 1008: 1003: 1001: 989: 987: 985: 981: 977: 973: 965: 961: 959: 958: 952: 950: 947: 943: 939: 935: 931: 928: 924: 920: 916: 913: 909: 905: 901: 897: 893: 889: 881: 879: 877: 876: 871: 867: 863: 859: 855: 854:not essential 851: 843: 827: 820: 818: 816: 812: 808: 807:hydroxymethyl 793: 789: 773: 769: 765: 761: 757: 753: 741: 735: 729: 726: 722: 717: 713: 707: 703: 700: 699: 695: 692: 688: 687: 683: 681: 680:Melting point 678: 677: 673: 671: 668: 667: 663: 660: 659: 652: 650: 647: 646: 622: 619: 615: 614: 609: 601: 596: 591: 587: 580: 569: 562: 552: 548: 541: 533: 529: 524: 523: 521: 511: 507: 506: 499: 494: 491: 486: 483: 478: 477: 475: 473: 470: 469: 462: 457: 454: 449: 446: 441: 440: 438: 432: 428: 427: 420: 415: 412: 407: 406: 404: 402: 399: 398: 391: 386: 385: 383: 380: 376: 375: 368: 367: 365: 363: 358: 357: 353: 349: 346: 344: 342:ECHA InfoCard 339: 338: 331: 326: 325: 323: 321: 318: 317: 310: 305: 302: 297: 294: 289: 288: 286: 284: 281: 280: 273: 268: 267: 265: 263: 260: 259: 252: 247: 246: 244: 242: 239: 238: 231: 226: 222: 219: 214: 213: 211: 207: 202: 201: 194: 189: 186: 181: 178: 173: 172: 170: 167: 163: 162: 157: 149: 143: 139: 134: 126: 119: 115: 112: 105: 101: 100: 96: 88: 76: 72: 64: 56: 52: 51: 47: 41: 37: 33: 19: 8466: 8465: 8429: 8421: 8414: 8411: 8288: 8254:Antagonists: 8253: 8108: 8063:Antagonists: 8062: 8036:1-Oleoyl-LPA 8032: 7944: 7933: 7926: 7919: 7645:picrotoxinin 7589:progesterone 7581:DHEA sulfate 7549:ginkgolide M 7545:ginkgolide J 7541:ginkgolide C 7537:ginkgolide B 7533:ginkgolide A 7505:nitrendipine 7443: 7240:Antagonists: 7239: 7115:Penicillin G 7059:ginsenosides 7016:Barbiturates 6985: 6965: 6912: 6868: 6846:β-ABA (BABA) 6837: 6752: 6745: 6736: 6735: 6719: 6716: 6588: 6495:Cyclopropane 6476: 6459: 6437: 6373: 6325:Propoxyphene 6295:Orphenadrine 6200:Ketobemidone 6165:Eticyclidine 6100:Coronaridine 6085:ARL-15896-AR 6001: 5969: 5881:-Cycloserine 5863:Carisoprodol 5819: 5707: 5705:Antagonists: 5704: 5637: 5632: 5615: 5588: 5547: 5543:-Cycloserine 5484: 5423: 5420: 5364:Barbiturates 5360: 5337:Selurampanel 5292:Dasolampanel 5279:Antagonists: 5278: 5248: 5181: 5178: 5152: 5089:Cyclopropane 5075:Barbiturates 5071: 5043:Selurampanel 4993:Dasolampanel 4965:Antagonists: 4964: 4948:Pramiracetam 4824: 4772: 4769: 4668:Acetaldehyde 4337: 4329: 4301: 4293: 4271:Trace amines 4179: 4107: 3941: 3934:oxaloacetate 3818: 3812:Homocysteine 3798: 3790: 3783: 3688:succinyl-CoA 3519:Glycocyamine 3494: 3452:Glutaryl-CoA 3409: 3317:Crotonyl-CoA 3307:Glutaryl-CoA 3287:Saccharopine 3160: 3105: 3064: 3048: 2918:Genetic code 2805: 2801: 2791: 2740: 2736: 2726: 2691: 2687: 2677: 2632: 2628: 2618: 2573: 2569: 2559: 2526: 2522: 2516: 2473: 2469: 2459: 2414: 2410: 2400: 2359: 2355: 2349: 2335: 2310: 2304: 2298: 2265: 2259: 2253: 2220: 2216: 2210: 2185: 2181: 2175: 2148: 2145:Hypertension 2144: 2138: 2130: 2097: 2093: 2087: 2042: 2038: 2032: 2024: 1989: 1985: 1975: 1934: 1931:Neuroscience 1930: 1920: 1911: 1873: 1869: 1859: 1850: 1810: 1806: 1796: 1771: 1767: 1761: 1744: 1739: 1733: 1718: 1675: 1669: 1648: 1640: 1628: 1615: 1591:Biochemistry 1590: 1567:. Retrieved 1562: 1553: 1536: 1532: 1528: 1522: 1514: 1506: 1500: 1496: 1486: 1469: 1465: 1459: 1447:. Retrieved 1433: 1414: 1408: 1400: 1395: 1355:hearing loss 1349: 1340: 1323: 1300: 1284: 1272: 1248: 1232: 1198: 1186: 1136: 1099:biosynthesis 1092: 1020: 1004: 993: 970: 956: 953: 937: 885: 882:Biosynthesis 873: 860:, including 850:stereoisomer 839: 792:deprotonated 759: 755: 751: 750: 705: 159:Identifiers 151:Other names 40: 8455:Sphingosine 8412:Precursors: 8122:Ceralifimod 8071:H2L-5765834 8066:H2L-5186303 7842:SSR-504,734 7837:SSR-103,800 7827:PF-03463275 7807:Mardepodect 7727:Transporter 7673:tropisetron 7615:levorphanol 7607:dextrorphan 7529:ginkgolides 7497:nicardipine 7352:Laudanosine 7273:Cacotheline 7263:Bicuculline 7210:sevoflurane 7160:tropisetron 7044:nicardipine 6887:Hypotaurine 6685:Pentamidine 6670:Minocycline 6650:Hodgkinsine 6620:Dexanabinol 6550:Sevoflurane 6404:Isoxsuprine 6399:Haloperidol 6379:Besonprodil 6340:Rimantadine 6290:Norketamine 6285:Noribogaine 6260:Milnacipran 6225:Levorphanol 6175:Gacyclidine 6145:Dizocilpine 6140:Diphenidine 6130:Dextrorphan 6050:Alaproclate 5993:Huperzine A 5946:Meprobamate 5906:Harkoseride 5801:Perzinfotel 5678:Plazinemdor 5225:Kainic acid 5210:Domoic acid 5156:Minocycline 5144:Sevoflurane 4821:Willardiine 4796:Domoic acid 4673:Ammonia (NH 4544:Nucleosides 4304:-Octopamine 4296:-Octopamine 4208:T-HCA (GHC) 4165:Hypotaurine 4117:GABA system 4068:Glutathione 3664:glutathione 3198:Imino acids 3162:Amino acids 3095:Pyrrolysine 3032:, uncharged 2743:(1): 4966. 2694:(5): e561. 2217:Amino Acids 1852:receptors). 1741:Org. Synth. 1107:pyrimidines 858:metabolites 844:. Only the 768:amino group 661:Appearance 611:Properties 348:100.000.250 272:ChEMBL11298 251:CHEBI:17115 8484:Categories 8346:Ceramidase 8312:inhibitors 8177:Mocravimod 8162:Fingolimod 8112:Amiselimod 8046:GRI-977143 7995:modulators 7847:Tilapertin 7802:LY-2365109 7797:Iclepertin 7792:GSK1018921 7677:zatosetron 7665:bemesetron 7637:Picrotoxin 7555:Imipramine 7525:bilobalide 7511:Furosemide 7501:nifedipine 7472:flurazepam 7460:clonazepam 7456:bromazepam 7427:Strychnine 7422:Sinomenine 7387:Quinolines 7377:Pitrazepin 7298:Dendrobine 7283:Colchicine 7202:isoflurane 7186:desflurane 7182:chloroform 7164:zatosetron 7148:bemesetron 7100:minaxolone 7088:alfaxolone 7074:Ivermectin 7011:Anandamide 6934:Milacemide 6924:-Threonine 6892:Ivermectin 6800:modulators 6723:AGN-241751 6695:Piretanide 6645:Furosemide 6630:Flupirtine 6607:Conantokin 6602:Caroverine 6597:Bumetanide 6530:Isoflurane 6500:Desflurane 6490:Chloroform 6429:Safaprodil 6424:Ro 25-6981 6365:Tiletamine 6350:Sabeluzole 6330:Remacemide 6275:Neramexane 6245:Methorphan 6230:Loperamide 6205:Lanicemine 6190:Indantadol 6155:Esketamine 6150:Ephenidine 6110:Dexoxadrol 6075:Arketamine 6060:Amantadine 6020:3-MeO-PCMo 5998:Putrescine 5941:MDL-105519 5916:Kynurenine 5896:Gavestinel 5811:SDZ-220581 5771:MDL-100453 5654:prasterone 5624:Spermidine 5597:Milacemide 5502:ACC (ACPC) 5388:Evans blue 5352:Topiramate 5342:Tezampanel 5272:Isoflurane 5149:Talampanel 5134:Perampanel 5129:Isoflurane 5114:GYKI-53655 5109:GYKI-52466 5104:Evans blue 5068:Zonampanel 5058:Topiramate 5048:Tezampanel 5023:Kynurenine 4983:Caroverine 4978:Becampanel 4928:Oxiracetam 4828:Aniracetam 4749:modulators 4661:Candidates 4535:Nucleobase 4324:Tryptamine 4319:Synephrine 4230:Monoamines 4195:GHB system 4028:Amino acid 3944:urea cycle 3801:-Adenosyl- 3775:methionine 3760:Tiglyl-CoA 3741:isoleucine 3640:Putrescine 3635:Cadaverine 3630:Citrulline 3529:Creatinine 3417:Kynurenine 3396:tryptophan 3269:acetyl-CoA 3254:metabolism 3251:Amino acid 3188:Glucogenic 3039:Asparagine 3015:Tryptophan 2972:Methionine 2961:Isoleucine 1992:: 109654. 1913:disorders. 1876:(1): 184. 1621:EC 3.1.3.3 1569:22 October 1388:References 1376:Homoserine 1211:-aspartate 1150:enantiomer 1119:tryptophan 1095:metabolism 1058:OH + 2 H 896:glycolysis 872:for silk, 821:Occurrence 772:protonated 764:amino acid 762:) is an α- 649:Molar mass 600:Zwitterion 498:1K77H2Z9B1 490:00PAR1C66F 487:D/L: 482:452VLY9402 450:D/L: 379:IUPHAR/BPS 298:D/L: 283:ChemSpider 225:Zwitterion 204:3D model ( 182:D/L: 166:CAS Number 142:IUPAC name 87:zwitterion 27:Amino acid 8467:See also: 8354:Ceranib 1 8292:Etrasimod 8289:Unsorted: 8277:VPC-23019 8262:CYM-50358 8232:TC-G 1006 8217:Siponimod 8192:Ponesimod 8187:Phyto-S1P 8152:CYM-50308 8147:CYM-50260 8117:Cenerimod 8109:Agonists: 8086:VPC-32183 8081:TC-LPA5 4 8033:Agonists: 7992:signaling 7895:ORG-25543 7875:Amoxapine 7832:Sarcosine 7812:ORG-24598 7777:CP-802079 7683:Verapamil 7669:LY-278584 7661:Tropeines 7627:pethidine 7623:oripavine 7516:Genistein 7447:Amiloride 7327:Gelsemine 7303:Diaboline 7288:Colubrine 7198:halothane 7194:enflurane 7170:Volatiles 7156:LY-278584 7140:Tropeines 7135:Triclofos 7125:Tamoxifen 7104:ORG-20599 7050:Etomidate 6973:brometone 6954:Sarcosine 6929:MDL-27531 6841:β-Alanine 6838:Agonists: 6737:See also: 6717:Unsorted: 6660:MDL-27266 6640:FR-115427 6635:FPL-12495 6592:ARR-15896 6520:Halothane 6510:Enflurane 6468:Magnesium 6419:Ro 8-4304 6394:Eliprodil 6305:PD-137889 6265:Morphanol 6240:Methadone 6235:Memantine 6185:Ibogamine 6160:Etoxadrol 6090:ARL-16247 6080:ARL-12495 6065:Aptiganel 6030:4-MeO-PCP 6025:3-MeO-PCP 6015:3-MeO-PCE 5978:Co 101676 5951:MRZ 2/576 5901:GV-196771 5891:Felbamate 5868:CGP-39653 5848:ACEA-1328 5843:ACEA-1011 5786:NPC-17742 5781:NPC-12626 5766:LY-274614 5761:LY-235959 5756:LY-233053 5741:CGS-19755 5736:CGP-40116 5731:CGP-39653 5726:CGP-39551 5721:CGP-37849 5711:AP5 (APV) 5612:Sarcosine 5488:β-Fluoro- 5437:Glutamate 5432:Aspartate 5421:Agonists: 5378:Enflurane 5322:LY-382884 5282:ACEA-1011 5267:Halothane 5262:Enflurane 5257:Diazoxide 5230:LY-339434 5215:Glutamate 5179:Agonists: 5124:Irampanel 5119:Halothane 5094:Enflurane 4968:ACEA-1011 4943:Piracetam 4923:ORG-26576 4918:Nooglutyl 4908:LY-503430 4903:LY-451646 4898:LY-404187 4893:LY-395153 4888:LY-392098 4873:Diazoxide 4801:Glutamate 4770:Agonists: 4552:Adenosine 4356:Histamine 4340:-Tyramine 4332:-Tyramine 4175:Sarcosine 4155:β-Alanine 4150:α-Alanine 3844:threonine 3660:glutamate 3625:Ornithine 3558:histidine 3544:glutamate 3371:β-Leucine 3183:Ketogenic 3173:Essential 3089:Histidine 3054:Threonine 3044:Glutamine 3005:Histidine 2944:Aliphatic 2824:1662-5102 2765:2041-1723 2592:0903-4641 2551:207299820 2523:CNS Drugs 2492:2167-8421 2376:1029-8428 2008:1873-7064 1951:1873-7544 1937:: 75–88. 1890:2158-3188 1829:1664-0640 1724:Carter HE 1632:Uniprot: 1371:Isoserine 1315:sarcosine 1158:glutamate 1133:Signaling 1073:Metabolic 1042:H + 2 H 932:) yields 888:oxidation 361:EC Number 8450:Ceramide 8387:Safingol 8336:Myriocin 8272:TY-52156 8237:TC-SP 14 8212:SEW-2871 8207:RPC-1063 8182:Ozanimod 8142:CYM 5541 8137:CYM-5520 8132:CYM-5442 8076:Ki-16425 8003:Receptor 7916:See also 7870:ALX-1393 7733:blockers 7714:instead. 7656:Riluzole 7641:picrotin 7631:thebaine 7619:morphine 7488:Daidzein 7478:Corymine 7464:diazepam 7399:5,7-CIQA 7332:iso-THAZ 7278:Caffeine 7144:atropine 7120:Propofol 7079:Ketamine 6969:Alcohols 6944:Propofol 6908:-Proline 6900:-Alanine 6864:-Alanine 6808:Receptor 6665:Metaphit 6575:Urethane 6463:Hydrogen 6460:Cations: 6370:Tramadol 6195:Ketamine 6180:Ibogaine 6095:Budipine 6010:3-HO-PCP 5936:LU-73068 5926:L-701324 5921:L-689560 5828:5,7-DCKA 5816:Selfotel 5698:SAGE-718 5693:SAGE-301 5688:SAGE-201 5629:Spermine 5619:Neomycin 5584:-Alanine 5576:L-687414 5535:-Alanine 5492:-alanine 5481:Theanine 5347:Theanine 5245:SYM-2081 5053:Theanine 4591:-derived 4537:-derived 4518:instead. 4473:Oleamide 4404:-derived 4385:instead. 4242:Dopamine 4053:Agmatine 4030:-derived 3900:tyrosine 3887:fumarate 3834:Cysteine 3656:cysteine 3620:Agmatine 3611:arginine 3515:creatine 3476:pyruvate 3292:Allysine 3142:Tyrosine 3136:Cysteine 3083:Arginine 3010:Tyrosine 2997:Aromatic 2842:34975405 2783:33009404 2718:25942042 2669:23729812 2610:31344283 2543:21936588 2500:27589995 2451:24086518 2411:PLOS ONE 2392:20271849 2384:28929385 2327:19963421 2290:25013468 2282:16763900 2245:17671611 2237:22588481 2202:20170643 2167:18809793 2122:45669104 2114:17929246 2079:10781100 2016:37437688 1967:23158971 1959:22814002 1908:32518273 1847:30787885 1788:11292060 1736:-Serine" 1730:(1940). 1559:"Serine" 1503:: 76–98. 1443:Archived 1365:See also 1359:tinnitus 1282:(iNTD). 1115:cysteine 930:2.6.1.52 915:1.1.1.95 754:(symbol 696:soluble 525:L: 495:D: 479:L: 458:D: 442:L: 416:D: 408:L: 387:L: 327:L: 320:DrugBank 306:D: 290:L: 269:L: 248:L: 215:L: 193:312-84-5 190:D: 185:302-84-1 174:L: 85:-serine 18:D-serine 8382:N,N-DMS 8267:JTE-013 8257:CS-0777 8247:XAX-162 8172:KRP-203 8127:CS-2100 8009:ligands 7900:VVZ-368 7767:ASP2535 7663:(e.g., 7639:(i.e., 7599:codeine 7597:(e.g., 7595:Opioids 7567:(e.g., 7531:(e.g., 7495:(e.g., 7454:(e.g., 7417:RU-5135 7389:(e.g., 7310:(e.g., 7268:Brucine 7214:toluene 7176:(e.g., 7152:cocaine 7142:(e.g., 7086:(e.g., 7061:(e.g., 7055:Ginseng 7042:(e.g., 7035:D12-116 7018:(e.g., 6971:(e.g., 6959:Taurine 6916:-Serine 6882:Glycine 6872:-Serine 6856:Caesium 6814:ligands 6709:saffron 6555:Toluene 6545:Octanol 6525:Hexanol 6480:Benzene 6456:TCN-213 6451:TCN-201 6446:MPX-007 6441:MPX-004 6035:8A-PDHQ 5973:Arcaine 5966:ZD-9379 5663:sulfate 5592:-Serine 5566:Glycine 5551:-Serine 5466:Proline 5393:NS-3763 5366:(e.g., 5357:UBP-302 5235:Proline 5077:(e.g., 4953:S-18986 4883:IDRA-21 4868:CX-1942 4863:CX-1739 4811:Proline 4589:Vitamin 4483:RVD-Hpα 4438:AA-5-HT 4185:Taurine 4170:Proline 4160:Glycine 4103:Proline 4073:Glycine 3592:proline 3511:glycine 3490:glycine 3481:citrate 3400:alanine 3332:leucine 3144:(≈10.1) 3085:(≈12.5) 3079:(≈10.8) 2987:Glycine 2982:Proline 2977:Alanine 2966:Leucine 2913:Peptide 2908:Protein 2833:8718999 2774:7532172 2745:Bibcode 2709:4471283 2660:3696825 2637:Bibcode 2601:6851881 2508:4584977 2442:3783393 2419:Bibcode 2047:Bibcode 1899:7283225 1838:6372501 1728:West HD 1449:5 March 1195:Ligands 1170:glycine 1168:at the 1166:agonist 1111:glycine 1103:purines 1046:→ HOCH 1023:serinol 976:glycine 957:E. coli 949:3.1.3.3 875:sericum 862:glycine 702:Acidity 670:Density 654:105.093 431:PubChem 330:DB00133 227:: 177:56-45-1 69:-serine 44:Serine 8515:Aldols 8430:Serine 8405:Others 8392:SKI II 8306:Enzyme 8202:RP-002 8197:RP-001 7521:Ginkgo 7411:7-TFQA 7258:αEMBTL 6851:β-AIBA 6585:Xylene 6485:Butane 5858:AV-101 5571:HA-966 4858:CX-717 4848:CX-614 4843:CX-546 4838:CX-516 4554:system 4428:2-ALPI 4349:Others 4180:Serine 4108:Serine 3697:valine 3495:serine 3278:lysine 3138:(≈8.3) 3132:(≈5.4) 3126:(≈4.1) 3120:(≈3.9) 3091:(≈6.1) 3077:Lysine 3049:Serine 2956:Valine 2840:  2830:  2822:  2781:  2771:  2763:  2716:  2706:  2667:  2657:  2608:  2598:  2590:  2549:  2541:  2506:  2498:  2490:  2449:  2439:  2390:  2382:  2374:  2325:  2288:  2280:  2243:  2235:  2200:  2165:  2120:  2112:  2077:  2067:  2014:  2006:  1965:  1957:  1949:  1906:  1896:  1888:  1845:  1835:  1827:  1813:: 25. 1786:  1747:: 81. 1692:  1657:  1603:  1421:  1213:. Had 1127:folate 815:codons 752:Serine 586:SMILES 419:C00740 411:C00065 262:ChEMBL 145:Serine 136:Names 32:Sérine 8282:W-146 8242:W-061 7885:NAGly 7858:GlyT2 7757:ACPPB 7745:GlyT1 7699:NMDAR 7437:Tutin 7407:7-TFQ 7403:7-CIQ 7228:Xenon 7174:gases 6580:Xenon 6040:18-MC 6005:2-MDP 5833:7-CKA 5796:PEAQX 5522:B6B21 5512:AK-51 5446:-HCA) 5409:NMDAR 5332:NS102 5063:YM90K 4758:AMPAR 4463:NAGly 4402:Lipid 4237:6-OHM 4129:GABOB 3958:Other 3649:other 3164:types 3030:Polar 2570:APMIS 2547:S2CID 2504:S2CID 2388:S2CID 2286:S2CID 2241:S2CID 2118:S2CID 2070:18334 1963:S2CID 1619:KEGG 1233:Pure 1144:from 1050:CH(NH 1034:CH(NH 898:) to 870:Latin 811:polar 547:InChI 461:71077 309:64231 241:ChEBI 206:JSmol 36:Sarin 8422:S1P: 8415:LPA: 8370:SphK 8097:S1PR 8056:OMPT 8021:LPAR 7935:GABA 7712:here 7710:See 7688:Zinc 7651:PMBA 7643:and 7560:NBQX 7312:2-AG 7233:Zinc 6986:tert 6877:GABA 6826:GlyR 6675:MPEP 6615:-αAA 6473:Zinc 6300:PCPr 6270:NEFA 5956:PNQX 5886:DNQX 5873:CNQX 5806:PPDA 5791:PBPD 5661:DHEA 5646:DHEA 5556:DHPG 5507:ACPD 5497:ACBD 5461:NMDA 5427:AMAA 5327:NBQX 5302:GAMS 5297:DNQX 5287:CNQX 5205:ATPA 5200:AMPA 5038:PNQX 5033:NBQX 5008:GAMS 4998:DNQX 4988:CNQX 4973:ATPO 4933:PEPA 4791:BOAA 4786:AMPA 4516:here 4514:See 4458:NADA 4433:2-OG 4418:2-AG 4383:here 4381:See 4124:GABA 4098:NAAG 4083:GSSG 4078:GSNO 3942:see 2838:PMID 2820:ISSN 2779:PMID 2761:ISSN 2714:PMID 2665:PMID 2606:PMID 2588:ISSN 2539:PMID 2496:PMID 2488:ISSN 2447:PMID 2380:PMID 2372:ISSN 2323:PMID 2278:PMID 2233:PMID 2198:PMID 2163:PMID 2110:PMID 2075:PMID 2012:PMID 2004:ISSN 1955:PMID 1947:ISSN 1904:PMID 1886:ISSN 1843:PMID 1825:ISSN 1784:PMID 1710:link 1690:ISBN 1655:ISBN 1634:serB 1623:etc. 1601:ISBN 1571:2012 1451:2018 1419:ISBN 1357:and 1125:and 1113:and 1105:and 1030:HOCH 904:NADH 902:and 866:silk 598:D/L 472:UNII 445:5951 401:KEGG 293:5736 223:D/L 8418:LPC 8359:OEA 8324:SPT 8227:SPC 8222:S1P 8051:LPA 5838:ACC 5746:CPP 5716:AP7 5527:CCG 5167:KAR 4571:ATP 4566:AMP 4561:ADP 4488:SEA 4478:PEA 4468:OEA 4453:LPI 4448:DEA 4203:GHB 4134:GHB 4093:NAA 2828:PMC 2810:doi 2769:PMC 2753:doi 2704:PMC 2696:doi 2655:PMC 2645:doi 2633:110 2596:PMC 2578:doi 2574:127 2531:doi 2478:doi 2437:PMC 2427:doi 2364:doi 2315:doi 2270:doi 2225:doi 2190:doi 2153:doi 2102:doi 2098:215 2065:PMC 2055:doi 1994:doi 1990:238 1939:doi 1935:222 1894:PMC 1878:doi 1833:PMC 1815:doi 1776:doi 1749:doi 1682:doi 1597:580 1541:doi 1474:doi 1311:ALS 1101:of 1054:)CH 1038:)CO 951:). 917:). 906:by 890:of 796:COO 758:or 756:Ser 515:EPA 453:617 434:CID 390:726 301:597 65:of 8486:: 8420:; 7675:, 7671:, 7667:, 7629:, 7625:, 7621:, 7617:, 7613:, 7609:, 7605:, 7601:, 7587:, 7583:, 7579:, 7575:, 7571:, 7551:)) 7547:, 7543:, 7539:, 7535:, 7527:, 7503:, 7499:, 7470:, 7466:, 7462:, 7458:, 7409:, 7405:, 7401:, 7397:, 7393:, 7314:, 7220:, 7216:, 7212:, 7208:, 7204:, 7200:, 7196:, 7192:, 7188:, 7184:, 7180:, 7162:, 7158:, 7154:, 7150:, 7146:, 7102:, 7098:, 7094:, 7090:, 7065:)) 7022:, 6998:, 6994:, 6990:, 6983:, 6979:, 6975:, 6587:; 6475:; 6458:; 6436:; 6372:; 6000:; 5968:; 5818:; 5636:24 5631:; 5614:; 5483:; 5370:, 5359:; 5247:; 5151:; 5081:, 5070:; 4823:; 4691:O) 4643:S) 3932:G→ 3885:G→ 3832:+ 3681:G→ 3666:: 3542:G→ 3517:: 3478:→ 3474:G→ 3166:: 2836:. 2826:. 2818:. 2806:15 2804:. 2800:. 2777:. 2767:. 2759:. 2751:. 2741:11 2739:. 2735:. 2712:. 2702:. 2690:. 2686:. 2663:. 2653:. 2643:. 2631:. 2627:. 2604:. 2594:. 2586:. 2572:. 2568:. 2545:. 2537:. 2527:25 2525:. 2502:. 2494:. 2486:. 2474:18 2472:. 2468:. 2445:. 2435:. 2425:. 2413:. 2409:. 2386:. 2378:. 2370:. 2360:33 2358:. 2321:. 2311:99 2309:. 2284:. 2276:. 2266:29 2264:. 2239:. 2231:. 2221:43 2219:. 2196:. 2186:79 2184:. 2161:. 2149:52 2147:. 2143:. 2116:. 2108:. 2096:. 2073:. 2063:. 2053:. 2043:97 2041:. 2037:. 2010:. 2002:. 1988:. 1984:. 1961:. 1953:. 1945:. 1933:. 1929:. 1910:. 1902:. 1892:. 1884:. 1874:10 1872:. 1868:. 1849:. 1841:. 1831:. 1823:. 1811:10 1809:. 1805:. 1782:. 1772:68 1770:. 1745:20 1738:. 1734:dl 1726:, 1706:}} 1702:{{ 1688:. 1599:. 1579:^ 1561:. 1537:35 1501:96 1470:56 1468:, 1361:. 1347:. 1293:. 1160:. 1025:: 1002:. 946:EC 927:EC 912:EC 776:NH 711:) 704:(p 8314:) 8310:( 8011:) 8007:( 7981:e 7974:t 7967:v 7937:A 7735:) 7731:( 7679:) 7647:) 7633:) 7591:) 7507:) 7474:) 7413:) 7318:) 7224:) 7172:/ 7166:) 7106:) 7046:) 7026:) 7002:) 6922:L 6914:L 6906:L 6898:L 6870:D 6862:D 6816:) 6812:( 6789:e 6782:t 6775:v 6711:) 6707:( 6613:D 5879:D 5669:) 5665:( 5656:) 5652:( 5638:S 5590:L 5582:L 5549:D 5541:D 5533:D 5490:D 5444:L 5374:) 5085:) 4738:e 4731:t 4724:v 4700:) 4698:2 4689:2 4677:) 4675:3 4641:2 4338:p 4330:m 4302:p 4294:m 4012:e 4005:t 3998:v 3902:→ 3898:→ 3865:→ 3846:→ 3822:: 3804:L 3799:S 3791:S 3787:: 3777:→ 3743:→ 3699:→ 3685:→ 3662:→ 3658:+ 3613:→ 3594:→ 3560:→ 3546:→ 3513:→ 3497:→ 3492:→ 3466:G 3410:N 3402:→ 3398:→ 3334:→ 3280:→ 3267:→ 3265:K 3243:e 3236:t 3229:v 3111:) 3109:a 3106:K 3070:) 3068:a 3065:K 2968:) 2954:( 2886:e 2879:t 2872:v 2844:. 2812:: 2785:. 2755:: 2747:: 2720:. 2698:: 2692:5 2671:. 2647:: 2639:: 2612:. 2580:: 2553:. 2533:: 2510:. 2480:: 2453:. 2429:: 2421:: 2415:8 2394:. 2366:: 2343:. 2329:. 2317:: 2292:. 2272:: 2247:. 2227:: 2204:. 2192:: 2169:. 2155:: 2139:N 2124:. 2104:: 2081:. 2057:: 2049:: 2033:N 2018:. 1996:: 1969:. 1941:: 1880:: 1817:: 1790:. 1778:: 1755:. 1751:: 1732:" 1712:) 1698:. 1684:: 1663:. 1609:. 1573:. 1547:. 1543:: 1529:l 1523:l 1481:. 1476:: 1453:. 1427:. 1351:D 1341:t 1329:D 1325:D 1319:L 1307:L 1303:L 1276:L 1251:L 1239:D 1235:D 1223:D 1219:D 1215:D 1209:D 1204:D 1200:D 1187:t 1182:D 1178:D 1162:D 1146:L 1138:D 1062:O 1060:2 1056:2 1052:2 1048:2 1044:2 1040:2 1036:2 1032:2 996:L 944:( 938:O 936:( 925:( 910:( 848:- 846:L 834:D 830:L 794:− 781:3 774:− 760:S 709:a 706:K 642:3 639:O 636:N 633:7 630:H 627:3 624:C 517:) 513:( 208:) 83:L 67:L 38:. 20:)

Index

D-serine
Sérine
Sarin
Skeletal formula
Skeletal formula
Serine at physiological pH
zwitterion

Ball-and-stick model

Space-filling model
IUPAC name
CAS Number
56-45-1
302-84-1
312-84-5
JSmol
Interactive image
Zwitterion
Interactive image
ChEBI
CHEBI:17115
ChEMBL
ChEMBL11298
ChemSpider
5736
597
64231
DrugBank
DB00133

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