601:
369:
1458:. This allows citrulline, a byproduct of the NOS-catalyzed production of nitric oxide, to be recycled to arginine in a pathway known as the citrulline to nitric oxide (citrulline-NO) or arginine-citrulline pathway. This is demonstrated by the fact that, in many cell types, nitric oxide synthesis can be supported to some extent by citrulline, and not just by arginine. This recycling is not quantitative, however, because citrulline accumulates in nitric oxide producing cells along with
1419:
1751:
metabolites L-citrulline, L-ornithine and agmatine formed distinct groups, which were altered in the schizophrenia group. Despite this, the biological basis of schizophrenia is still poorly understood, a number of factors, such as dopamine hyperfunction, glutamatergic hypofunction, GABAergic deficits, cholinergic system dysfunction, stress vulnerability and neurodevelopmental disruption, have been linked to the aetiology and/or pathophysiology of the disease.
47:
1005:
27:
61:
3751:
1602:
1337:, depending on the developmental stage and health status of the individual. Preterm infants are unable to synthesize arginine internally, making the amino acid nutritionally essential for them. Most healthy people do not need to supplement with arginine because it is a component of all protein-containing foods and can be synthesized in the body from
1750:
concentration and glutamate/GABA ratio in the schizophrenia cases. Regression analysis indicated positive correlations between arginase activity and the age of disease onset and between L-ornithine level and the duration of illness. Moreover, cluster analyses revealed that L-arginine and its main
1698:
may lie more in prevention than treatment." and that "the use of lysine for decreasing the severity or duration of outbreaks" is not supported, while further research is needed. A 2017 study concludes that "clinicians could consider advising patients that there is a theoretical role of lysine
1450:, which extract the citrulline and convert it to arginine, which is returned to the blood. This means that impaired small bowel or renal function can reduce arginine synthesis and thus create a dietary requirement for arginine. For such a person, arginine would become "essential".
1667:. A review of clinical trials concluded that oral arginine increases growth hormone, but decreases growth hormone secretion, which is normally associated with exercising. However, a more recent trial reported that although oral arginine increased plasma levels of
1510:
hydrocarbon chain. Because globular proteins have hydrophobic interiors and hydrophilic surfaces, arginine is typically found on the outside of the protein, where the hydrophilic head group can interact with the polar environment, for example taking part in
1368:
which need to be processed through the urea cycle, and if not enough arginine is present, the resulting ammonia toxicity can be lethal. This is not a problem in practice, because meat contains sufficient arginine to avoid this situation.
1345:. Additional, dietary arginine is necessary for otherwise healthy individuals temporarily under physiological stress, for example during recovery from burns, injury or sepsis, or if either of the major sites of arginine biosynthesis, the
1292:(αΌΟΞ³Ο
ΟΞΏΟ) meaning "silver" due to the silver-white appearance of arginine nitrate crystals. In 1897, Schulze and Ernst Winterstein (1865β1949) determined the structure of arginine. Schulze and Winterstein synthesized arginine from
1770:
L-arginine is recognized as safe (GRAS-status) at intakes of up to 20 grams per day. L-arginine is found in many foods, such as fish, poultry, and dairy products, and is used as a dietary supplement. It may interact with various
1699:
supplementation in the prevention of herpes simplex sores but the research evidence is insufficient to back this. Patients with cardiovascular or gallbladder disease should be cautioned and warned of the theoretical risks."
1013:
985:
1453:
Synthesis of arginine from citrulline also occurs at a low level in many other cells, and cellular capacity for arginine synthesis can be markedly increased under circumstances that increase the production of
3405:
Dong JY, Qin LQ, Zhang Z, et al. (December 2011). "Effect of oral L-arginine supplementation on blood pressure: a meta-analysis of randomized, double-blind, placebo-controlled trials". review.
4064:
4833:
1047:
955:
3707:
4057:
2183:
1519:
For this reason, it is frequently found at the interface between two proteins. The aliphatic part of the side chain sometimes remains below the surface of the protein.
1948:
4826:
3151:
Alba-Roth J, MΓΌller OA, Schopohl J, von Werder K (December 1988). "Arginine stimulates growth hormone secretion by suppressing endogenous somatostatin secretion".
4050:
654:
5966:
4819:
1372:
Animal sources of arginine include meat, dairy products, and eggs, and plant sources include seeds of all types, for example grains, beans, and nuts.
1530:.This is important in fetal development, is part of the normal immune process, as well as the control of gene expression, but is also significant in
1516:
184:
3700:
4000:
923:
4259:
3659:
3237:
Forbes SC, Bell GJ (June 2011). "The acute effects of a low and high dose of oral L-arginine supplementation in young active males at rest".
2503:
2473:
2446:
2416:
2363:
2333:
1899:
896:
4572:
4163:
1554:, as well as an intercellular messenger which regulates vasodilation, and also has functions in the immune system's reaction to infection.
1711:-arginine reduces blood pressure with pooled estimates of 5.4 mmHg for systolic blood pressure and 2.7 mmHg for diastolic blood pressure.
168:
196:
5595:
4168:
1691:, would interfere markedly with virus synthesis", but concludes that "no ready explanation is available for any of these observations".
176:
6143:
6021:
3693:
2929:
2200:
1506:, because at physiological pH it contains a positively charged guanidinium group, which is highly polar, at the end of a hydrophobic
5280:
2994:
2967:
2571:
2390:
1742:
Both liquid chromatography and liquid chromatography/mass spectrometric assays have found that brain tissue of deceased people with
615:
5446:
1827:
1746:
shows altered arginine metabolism. Assays also confirmed significantly reduced levels of Ξ³-aminobutyric acid (GABA), but increased
5633:
3442:"Arginine supplementation for improving maternal and neonatal outcomes in hypertensive disorder of pregnancy: a systematic review"
1415:
are bidirectional. Thus, the net use or production of these amino acids is highly dependent on cell type and developmental stage.
4959:
1353:, have reduced function, because the small bowel does the first step of the synthesizing process and the kidneys do the second.
6148:
5250:
4394:
1523:
1360:. For some carnivores, for example cats, dogs and ferrets, arginine is essential, because after a meal, their highly efficient
5355:
6035:
1325:. It is obtained commercially by fermentation. In this way, 25-35 g/liter can be produced, using glucose as a carbon source.
423:
1955:
5717:
5585:
4423:
1862:
1190:
6123:
5285:
5109:
4553:
3990:
1385:
1041:
532:
3675:
1663:
Intravenously administered arginine is used in growth hormone stimulation tests because it stimulates the secretion of
26:
5971:
5782:
5255:
4995:
4731:
4264:
1578:
578:
1004:
6158:
6153:
5854:
5740:
5673:
5540:
5119:
1629:
1120:
829:
5005:
4893:
4620:
4528:
4254:
4203:
4178:
3774:
376:
5812:
5686:
5603:
5245:
1233:
group appended to a standard amino acid framework. At physiological pH, the carboxylic acid is deprotonated (βCO
4741:
4548:
4404:
4183:
3716:
2295:
1723:
1719:
1577:(mainly through ornithine and to a lesser degree through agmatine, citrulline, and glutamate). The presence of
1108:
455:
5500:
2587:
Stechmiller JK, Childress B, Cowan L (February 2005). "Arginine supplementation and wound healing". (review).
5792:
5623:
5490:
4188:
3587:
Shao A, Hathcock JN (April 2008). "Risk assessment for the amino acids taurine, L-glutamine and L-arginine".
1494:. Arginine is necessary for T-cells to function in the body, and can lead to their deregulation if depleted.
6052:
5663:
5580:
5312:
5124:
5000:
4587:
4543:
4371:
4144:
1980:
1551:
1401:
1389:
1285:
1132:
5952:
5859:
5608:
5340:
364:
6049:
5753:
5699:
5562:
5549:
5307:
5010:
4796:
4675:
4652:
4490:
4399:
4326:
4231:
4119:
4079:
4010:
1397:
872:
5668:
5270:
5240:
1581:(ADMA), a close relative, inhibits the nitric oxide reaction; therefore, ADMA is considered a marker for
288:
5976:
5658:
5473:
5260:
4612:
4288:
4005:
3995:
2749:"Upregulation of colonic luminal polyamines produced by intestinal microbiota delays senescence in mice"
1550:
Arginine is the immediate precursor of nitric oxide, an important signaling molecule which can act as a
1455:
1393:
1262:
1027:
997:
816:
84:
5613:
5317:
5265:
5089:
5084:
3680:
1638:
of 13.8, and is therefore always protonated and positively charged at physiological pH. Because of the
461:
280:
5898:
5495:
5235:
5104:
5094:
2808:"Understanding the association of stem cells in fetal development and carcinogenesis during pregnancy"
5510:
5505:
5335:
5322:
5275:
5099:
5025:
5015:
4087:
4076:
4015:
2760:
1680:
1443:
1334:
1175:
53:
6168:
6163:
5986:
5916:
4788:
4577:
4269:
4249:
3819:
596:
108:
67:
4934:
2622:
Witte MB, Barbul A (2003). "Arginine physiology and its implication for wound healing". (review).
5653:
5638:
5416:
5396:
5365:
5217:
5174:
4939:
4919:
4914:
4909:
4848:
4198:
3766:
3569:
3219:
3176:
2837:
2647:
1916:"IUPAC-IUB Commission on Biochemical Nomenclature A One-Letter Notation for Amino Acid Sequences"
1802:
1784:
1531:
1507:
1361:
227:
5921:
5712:
5643:
5391:
5370:
4042:
1418:
1301:
215:
5797:
5530:
4924:
4904:
2002:
5832:
5827:
5441:
5436:
5360:
5194:
5055:
5050:
5045:
5040:
4884:
4736:
4694:
4030:
3852:
3655:
3604:
3561:
3553:
3514:
3463:
3422:
3387:
3346:
3305:
3254:
3211:
3168:
3116:
3067:
2990:
2963:
2957:
2935:
2925:
2894:
2876:
2829:
2788:
2729:
2688:
2639:
2604:
2567:
2542:
2499:
2469:
2463:
2442:
2436:
2412:
2386:
2359:
2329:
2277:
2236:
2196:
2087:
1895:
1889:
1772:
1639:
1539:
1080:
46:
5822:
5817:
5807:
5787:
5520:
5035:
2984:
2561:
2493:
2406:
2380:
2353:
2323:
2256:"Arginine deficiency in preterm infants: biochemical mechanisms and nutritional implications"
5868:
5462:
5431:
5345:
5296:
5189:
5140:
5020:
4244:
4124:
3596:
3545:
3504:
3494:
3453:
3414:
3377:
3336:
3295:
3285:
3246:
3203:
3160:
3106:
3098:
3057:
3047:
2921:
2884:
2868:
2819:
2778:
2768:
2719:
2678:
2631:
2596:
2532:
2267:
2228:
2188:
2163:
2136:
2068:
2036:
1927:
1760:
1582:
1142:
787:
701:
32:
5618:
5230:
566:
558:
550:
542:
325:
6056:
5727:
5515:
5350:
5114:
4538:
4346:
1695:
1483:
1431:
1427:
1346:
1258:
1237:) and both the amino and guanidino groups are protonated, resulting in a cation. Only the
395:
309:
143:
127:
60:
624:
InChI=1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t4-/m0/s1
317:
135:
2959:
Bioinformatics for
Geneticists: A Bioinformatics Primer for the Analysis of Genetic Data
2764:
1915:
1859:
Recommendations on
Organic & Biochemical Nomenclature, Symbols & Terminology etc
1831:
1522:
Arginine residues in proteins can be deiminated by PAD enzymes to form citrulline, in a
600:
368:
259:
119:
6076:
5735:
5628:
5525:
5225:
5212:
5199:
4845:
4533:
4173:
4134:
3952:
3509:
3482:
3382:
3365:
3111:
3086:
3062:
3035:
2889:
2783:
2748:
1664:
1527:
1491:
1281:
1184:
3685:
3300:
3273:
2683:
2666:
2232:
1932:
6137:
6017:
5766:
5575:
5204:
5184:
5179:
5164:
4718:
4685:
4647:
4505:
4389:
4025:
3946:
3940:
3842:
3034:
Gambardella J, Khondkar W, Morelli MB, Wang X, Santulli G, Trimarco V (August 2020).
2841:
2635:
1743:
1727:
1647:
1512:
1479:
1475:
1087:
853:
776:
766:
357:
4811:
3625:
3573:
3223:
2651:
6094:
6070:
5401:
5169:
4869:
4856:
4842:
4756:
4634:
4510:
4341:
4274:
4139:
4129:
4109:
3740:
3180:
2914:
1731:
1487:
1266:
1254:
966:
961:
4193:
3139:
2272:
2255:
2192:
500:
3290:
3207:
2872:
2824:
2807:
484:
6107:
5878:
5802:
5411:
5406:
5291:
5132:
5030:
4874:
4486:
3984:
3917:
3600:
3134:
3052:
2300:
2219:
Tapiero H, MathΓ© G, Couvreur P, Tew KD (November 2002). "L-Arginine". (review).
1617:
1590:
1535:
1230:
1068:
809:
492:
3750:
2856:
2600:
2092:(2nd ed.). New York, New York, USA: Longmans, Green & Co. p. 140.
1601:
6080:
6060:
5994:
5648:
5065:
5060:
4949:
4929:
4766:
4642:
4607:
4597:
4582:
4563:
4462:
4457:
4452:
4351:
4239:
4218:
4091:
4073:
4020:
3861:
3837:
3794:
3783:
3549:
3418:
2724:
2707:
2537:
2520:
2140:
1854:
1830:. IUPAC-IUB Joint Commission on Biochemical Nomenclature. 1983. Archived from
1794:
1614:
1503:
1381:
1357:
1342:
1318:
1272:
The one-letter symbol R was assigned to arginine for its phonetic similarity.
1206:
798:
735:
683:
412:
299:
191:
3557:
3458:
3441:
2880:
2833:
2167:
2072:
2040:
1033:
6066:
6025:
5888:
5883:
4944:
4666:
4482:
4447:
4380:
4366:
3911:
3876:
3866:
3827:
3533:
3341:
3324:
2939:
2806:
Banerjee, Kasturi; Chattopadhyay, Agnibha; Banerjee, Satarupa (2022-07-01).
1806:
1684:
1643:
1625:
1621:
1574:
1562:
1439:
1435:
1408:
1338:
1297:
1293:
1160:
3608:
3565:
3518:
3467:
3426:
3391:
3350:
3309:
3258:
3215:
3164:
3120:
3071:
2898:
2792:
2733:
2692:
2643:
2608:
2546:
2281:
2240:
6100:
cGMP preferring PDE inhibitors (e.g., sildenafil, paraxanthine, tadalafil)
3172:
6087:
6043:
6029:
5846:
5535:
5426:
4973:
4864:
4722:
4709:
4656:
4478:
4442:
4337:
4298:
4114:
3964:
3958:
3832:
3652:
Analysis of
Protein Post-Translational Modifications by Mass Spectrometry
1798:
1747:
1646:, the positive charge is delocalized, enabling the formation of multiple
1570:
1566:
1261:
CGU, CGC, CGA, CGG, AGA, and AGG. The guanidine group in arginine is the
1137:
336:
3499:
2855:
Rodriguez, Paulo C.; Quiceno, David G.; Ochoa, Augusto C. (2006-10-05).
1392:. This is an energetically costly process, because for each molecule of
346:
6007:
5873:
5386:
5381:
5330:
5149:
5144:
5070:
4990:
4979:
4414:
4333:
4312:
4303:
4222:
4208:
4154:
3809:
3804:
3799:
3788:
3735:
3730:
2857:"l-arginine availability regulates T-lymphocyte cell-cycle progression"
1463:
1459:
1412:
1365:
1322:
1250:
1249:) enantiomer is found naturally. Arg residues are common components of
804:
470:
377:
3534:"Oral L-arginine can reverse digital necrosis in Raynaud's phenomenon"
2773:
2438:
Nutrition and
Disease Management for Veterinary Technicians and Nurses
1486:, and the release of hormones. It is a precursor for the synthesis of
6103:
5999:
5893:
5456:
4519:
4317:
4100:
3899:
3871:
3778:
3102:
1688:
1447:
1356:
Arginine is an essential amino acid for birds, as they do not have a
1350:
270:
3250:
3194:
Kanaley JA (January 2008). "Growth hormone, arginine and exercise".
2104:
2056:
2024:
1384:
in the urea cycle by the sequential action of the cytosolic enzymes
1183:
Except where otherwise noted, data are given for materials in their
2920:(3rd ed.). San Francisco, Calif.: Benjamin Cummings. pp.
2181:
Drauz K, Grayson I, Kleemann A, et al. (2006). "Amino Acids".
1300:
in 1899, but some doubts about arginine's structure lingered until
444:
1600:
1417:
511:
249:
195:
183:
175:
167:
156:
3366:"Lysine for Herpes Simplex Prophylaxis: A Review of the Evidence"
1442:, which is secreted into the bloodstream which carries it to the
5981:
5908:
5482:
3628:. MedlinePlus, US National Institutes of Health. 13 October 2021
3274:"Amino Acid Requirements of Herpes Simplex Virus in Human Cells"
1789:
1558:
756:
434:
4815:
4046:
3689:
1534:. Another post-translational modification of arginine involves
2563:
The
Metabolic Challenges of Immune Cells in Health and Disease
1759:
Oral L-arginine has been shown to reverse digital necrosis in
2119:[On the synthesis of racemic arginine (Ξ±-amino-Ξ΄-guanido-
2003:"BIOETYMOLOGY: ORIGIN IN BIO-MEDICAL TERMS: arginine (Arg R)"
1288:
and his assistant Ernst
Steiger. He named it from the Greek
1269:. Like all amino acids, it is a white, water-soluble solid.
583:
59:
45:
3532:
Rembold, Christopher M.; Ayers, Carlos R. (February 2003).
2495:
Bioactive
Dietary Factors and Plant Extracts in Dermatology
1333:
Arginine is classified as a semiessential or conditionally
1853:
IUPAC-IUBMB Joint
Commission on Biochemical Nomenclature.
1683:
in human cells indicated that "...the lack of arginine or
1671:-arginine it did not cause an increase in growth hormone.
1855:"Nomenclature and Symbolism for Amino Acids and Peptides"
1828:"Nomenclature and Symbolism for Amino Acids and Peptides"
3196:
Current
Opinion in Clinical Nutrition and Metabolic Care
2325:
Dietitian's
Handbook of Enteral and Parenteral Nutrition
2154:
Brand E, Sandberg M (1932). "d-Arginine Hydrochloride".
1624:
straight chain, the distal end of which is capped by a
4865:
Nitroxyl anion (NO; oxonitrate(1-), hyponitrite anion)
1730:. It did not lower systolic blood pressure or improve
1726:, including women with high blood pressure as part of
3481:
Liu P, Jing Y, Collie ND, et al. (August 2016).
3085:
Fitch CA, Platzer G, Okon M, et al. (May 2015).
2498:. Springer Science & Business Media. p. 75.
2385:. Springer Science & Business Media. p. 45.
2123:-valeric acid) and of the isomeric Ξ±-guanido-Ξ΄-amino-
1694:
Further reviews conclude that "lysine's efficacy for
1466:, the stable end-products of nitric oxide breakdown.
3483:"Altered brain arginine metabolism in schizophrenia"
3153:
The Journal of Clinical Endocrinology and Metabolism
2254:
Wu G, Jaeger LA, Bazer FW, Rhoads JM (August 2004).
5934:
5907:
5845:
5775:
5726:
5594:
5481:
5472:
5455:
5356:
Methylamine hexamethylene methylamine/NO (MAHMA/NO)
4972:
4892:
4883:
4855:
4787:
4780:
4754:
4717:
4707:
4684:
4665:
4596:
4562:
4518:
4503:
4471:
4432:
4413:
4379:
4364:
4311:
4296:
4287:
4217:
4153:
4099:
4086:
3926:
3885:
3851:
3818:
3765:
3758:
3723:
3446:
Journal of the Renin-Angiotensin-Aldosterone System
2113:-valeriansΓ€ure) und der isomeren Ξ±-Guanido-Ξ΄-amino-
2045:
The structure for arginine is presented on p. 2882.
1679:Research from 1964 into amino acid requirements of
422:
2913:
5170:Amyl nitrite (isoamyl nitrite, isopentyl nitrite)
2747:Kibe R, Kurihara S, Sakai Y, et al. (2014).
2718:(10 Suppl): 2807Sβ2811S, discussion 2818Sβ2819S.
2531:(10 Suppl): 2743Sβ2747S, discussion 2765Sβ2767S.
1605:Delocalization of charge in guanidinium group of
214:
842:2.18 (carboxyl), 9.09 (amino), 13.8 (guanidino)
499:
491:
483:
5031:Naproxcinod (nitronaproxen; AZD-3582, HCT-3012)
3440:Gui S, Jia J, Niu X, et al. (March 2014).
2462:Spano MA, Kruskall LJ, Thomas DT (2017-08-30).
2089:Organic Chemistry for Advanced Students, Part 3
1490:(NO), making it important in the regulation of
634:D/L: Key: ODKSFYDXXFIFQN-UHFFFAOYSA-N
142:
134:
126:
118:
3021:
3009:
2667:"Enzymatic function of nitric oxide synthases"
2411:. National Academies Press. 1985. p. 65.
2184:Ullmann's Encyclopedia of Industrial Chemistry
2129:Berichte der Deutschen Chemischen Gesellschaft
2061:Berichte der Deutschen Chemischen Gesellschaft
2029:Berichte der Deutschen Chemischen Gesellschaft
5447:N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide
5006:Ethylene glycol dinitrate (EGDN; nitroglycol)
4827:
4058:
3701:
3239:Applied Physiology, Nutrition, and Metabolism
2358:. Jones & Bartlett Learning. p. 48.
2328:. Jones & Bartlett Learning. p. 76.
2027:[On a cleavage product of arginine].
1426:Arginine is made by the body as follows. The
1321:of various cheap sources of protein, such as
641:D: Key: ODKSFYDXXFIFQN-SCSAIBSYSA-N
8:
1589:-arginine is considered a sign of a healthy
1573:; and can also be used for the synthesis of
2912:Mathews CK, Van Holde KE, Ahern KG (2000).
2059:[On the constitution of arginine].
2023:Schulze E, Winterstein E (September 1897).
5478:
5469:
4889:
4834:
4820:
4812:
4784:
4714:
4515:
4376:
4308:
4293:
4096:
4065:
4051:
4043:
3762:
3708:
3694:
3686:
3329:American Journal of Health-System Pharmacy
3325:"Lysine for management of herpes labialis"
2214:
2212:
2025:"Ueber ein Spaltungs-product des Arginins"
599:
367:
324:
316:
308:
18:
5190:Isobutyl nitrite (2-methylpropyl nitrite)
5100:Nitroglycerin (glyceryl trinitrate (GTN))
3508:
3498:
3457:
3381:
3340:
3299:
3289:
3110:
3061:
3051:
2888:
2823:
2782:
2772:
2723:
2682:
2536:
2465:Nutrition for Sport, Exercise, and Health
2271:
2055:Schulze E, Winterstein E (October 1899).
1931:
1642:between the double bond and the nitrogen
1280:Arginine was first isolated in 1886 from
565:
557:
549:
541:
5266:S-Nitrosocysteine (SNC, CysNO, SNO-Cys)
5256:S-Nitroso-N-valerylpenicillamine (SNVP)
2989:. Oxford University Press. p. 13.
2812:Advances in Cancer Biology - Metastasis
2260:The Journal of Nutritional Biochemistry
1819:
1722:and lengthens pregnancy for women with
659:
620:
595:
460:
345:
5251:S-Nitroso-N-acetylpenicillamine (SNAP)
5125:Sodium trioxodinitrate (Angeli's salt)
3620:
3618:
3589:Regulatory Toxicology and Pharmacology
3323:Tomblin FA, Lucas KH (February 2001).
2962:. John Wiley & Sons. p. 326.
2441:. John Wiley & Sons. p. 232.
1891:Nitric Oxide: Biology and Pathobiology
1766:Safety and potential drug interactions
1404:(AMP), consuming two ATP equivalents.
781:368 Β°C (694 Β°F; 641 K)
358:
4260:2-Amino-3-carboxymuconic semialdehyde
2951:
2949:
2487:
2485:
2430:
2428:
2379:Freedland RA, Briggs S (2012-12-06).
2347:
2345:
2057:"Ueber die Constitution des Arginins"
1985:Zeitschrift fΓΌr Physiologische Chemie
1456:inducible nitric oxide synthase (NOS)
1396:that is synthesized, one molecule of
771:260 Β°C; 500 Β°F; 533 K
627:Key: ODKSFYDXXFIFQN-BYPYZUCNSA-N
287:
279:
258:
7:
6086:non-selective PDE inhibitors (e.g.,
4870:Nitric oxide (NO; nitrogen monoxide)
4573:2,3-Dihydroxy-3-methylpentanoic acid
1883:
1881:
1879:
1569:; is necessary for the synthesis of
1474:Arginine plays an important role in
965:
5110:Pentaerithrityl tetranitrate (PETN)
4996:Diethylene glycol dinitrate (DEGDN)
3717:Encoded (proteinogenic) amino acids
3538:Molecular and Cellular Biochemistry
3087:"Arginine: Its pKa value revisited"
3036:"Arginine and Endothelial Function"
2435:Wortinger A, Burns K (2015-06-11).
2382:A Biochemical Approach to Nutrition
1620:of arginine consists of a 3-carbon
1434:produce citrulline, primarily from
473:
443:
6015:Indirect/downstream NO modulators:
5783:Asymmetric dimethylarginine (ADMA)
2665:Andrew PJ, Mayer B (August 1999).
2566:. Frontiers Media SA. p. 17.
2492:Watson RR, Zibadi S (2012-11-28).
1482:, removing ammonia from the body,
14:
5813:Nitroarginine methyl ester (NAME)
5276:S-Nitrosoglutathione (GSNO, SNOG)
5246:S-Nitroso-N-acetylcysteine (SNAC)
5120:Propylene glycol dinitrate (PGDN)
4875:Nitrosonium (NO; nitrosyl cation)
3364:Mailoo VJ, Rampes S (June 2017).
2221:Biomedicine & Pharmacotherapy
1675:Herpes-Simplex Virus (Cold sores)
1557:Arginine is also a precursor for
96:2-Amino-5-guanidinopentanoic acid
3749:
2636:10.1046/j.1524-475X.2003.11605.x
2560:Mauro C, Frezza C (2015-07-13).
2521:"Enzymes of arginine metabolism"
2296:"Drugs and Supplements Arginine"
1865:from the original on 29 May 2007
1317:It is traditionally obtained by
1284:seedlings by the German chemist
1003:
719:
713:
667:D/L: C(CC(C(=O)O)N)CNC(=N)N
25:
5341:Diethylenetriamine/NO (DETA/NO)
4395:Imidazol-4-one-5-propionic acid
3650:Griffiths JR, Unwin RD (2016).
3140:Growth hormone stimulation test
2468:. Human Kinetics. p. 240.
1926:(13): 3557β3559. 10 July 1968.
1920:Journal of Biological Chemistry
1894:. Academic Press. p. 189.
1687:, and possibly the presence of
1524:post-translational modification
1407:The pathways linking arginine,
1187:(at 25 Β°C , 100 kPa).
677:L HCl: .NC(CCCNC(N)=)C()=O
5541:N-(1-Iminoethyl)-L-ornithine (
4209:Ξ²-Hydroxy Ξ²-methylglutaryl-CoA
4164:Ξ²-Hydroxy Ξ²-methylbutyric acid
2589:Nutrition in Clinical Practice
1949:"Biographie von Ernst Schulze"
725:
707:
1:
6124:Receptor/signaling modulators
5793:Guanidinoethyldisulfide (GED)
5011:Isosorbide mononitrate (ISMN)
5001:Erythritol tetranitrate (ETN)
4424:1-Pyrroline-5-carboxylic acid
4169:Ξ²-Hydroxy Ξ²-methylbutyryl-CoA
2708:"L-arginine and hypertension"
2684:10.1016/S0008-6363(99)00115-7
2624:Wound Repair and Regeneration
2408:Nutrient Requirements of Dogs
2273:10.1016/j.jnutbio.2003.11.010
2233:10.1016/s0753-3322(02)00284-6
2193:10.1002/14356007.a02_057.pub2
2109:-Arginins (Ξ±-Amino-Ξ΄-guanido-
2103:SΓΆlrensen SP (January 1910).
1979:Schulze E, Steiger E (1887).
1933:10.1016/S0021-9258(19)34176-6
1380:Arginine is synthesized from
1364:produces large quantities of
672:D: C(C(C(=O)O)N)CNC(=N)N
662:L: C(C(C(=O)O)N)CNC(=N)N
5261:S-Nitrosocaptopril (SNO-Cap)
5090:Nitroflurbiprofen (HCT-1026)
5085:Nitroatorvastatin (NCX-6560)
4554:2-Methyl-3-oxopropanoic acid
3291:10.1128/jb.87.3.609-613.1964
3272:Tankersley RW (March 1964).
3208:10.1097/MCO.0b013e3282f2b0ad
2873:10.1182/blood-2006-06-031856
2825:10.1016/j.adcanc.2022.100042
1707:A meta-analysis showed that
1386:argininosuccinate synthetase
1229:H. The molecule features a
5736:Aminoguanidine (pimagedine)
5629:Aminoguanidine (pimagedine)
5526:Aminoguanidine (pimagedine)
5290:N-Nitroso compounds (e.g.,
5105:Nitropravastatin (NCX-6550)
5016:Isosorbide dinitrate (ISDN)
4732:4-Hydroxyphenylpyruvic acid
4265:2-Aminomuconic semialdehyde
3601:10.1016/j.yrtph.2008.01.004
3053:10.3390/biomedicines8080277
2986:Protein-protein Recognition
1579:asymmetric dimethylarginine
1057:or concentration (LD, LC):
866:232.8 J K mol (at 23.7 Β°C)
41:
6185:
6022:AT-II receptor antagonists
5767:Nitroarginine (NNA, NOARG)
5604:1-Amino-2-hydroxyguanidine
5576:Nitroarginine (NNA, NOARG)
5323:Sodium nitroprusside (SNP)
4608:generation of homocysteine
3775:Branched-chain amino acids
3022:Griffiths & Unwin 2016
3010:Griffiths & Unwin 2016
2601:10.1177/011542650502000152
2519:Morris SM (October 2004).
1754:
6144:Proteinogenic amino acids
6117:
4255:3-Hydroxyanthranilic acid
3978:
3747:
3654:. John Wiley & Sons.
3419:10.1016/j.ahj.2011.09.012
2141:10.1002/cber.191004301109
1888:Ignarro LJ (2000-09-13).
1502:Arginine's side chain is
1181:
1174:
1169:
1094:
1053:
984:
979:
948:
846:
694:
686:: NC(CCCNC(N)=)C()=O
650:
611:
101:
93:
83:
78:
40:
24:
5501:3-Chloro-5-nitroindazole
5336:Diethylamine/NO (DEA/NO)
5308:Metal nitrosyl complexes
5236:S-Nitrosoalbumin (SNALB)
4930:Cinaciguat (BAY 58-2667)
4742:4-Maleylacetoacetic acid
4549:3-Hydroxyisobutyric acid
4405:Glutamate-1-semialdehyde
3487:Translational Psychiatry
3459:10.1177/1470320313475910
3135:MedlinePlus Encyclopedia
2956:Barnes MR (2007-04-16).
2712:The Journal of Nutrition
2706:Gokce N (October 2004).
2525:The Journal of Nutrition
2168:10.15227/orgsyn.012.0004
2073:10.1002/cber.18990320385
2041:10.1002/cber.18970300389
1775:and herbal supplements.
1724:gestational hypertension
1720:diastolic blood pressure
1265:for the biosynthesis of
1170:Supplementary data page
1042:Precautionary statements
6093:PDE9 inhibitors (e.g.,
5581:Pentamidine isethionate
5491:3-Bromo-7-nitroindazole
5378:Heterocyclic compounds:
4902:Activators/stimulators:
4588:2-Methylacetoacetyl-CoA
4544:3-Hydroxyisobutyryl-CoA
4080:metabolic intermediates
3681:L-arginine, Mayo Clinic
3550:10.1023/A:1022422932108
3278:Journal of Bacteriology
2725:10.1093/jn/134.10.2807S
2671:Cardiovascular Research
2538:10.1093/jn/134.10.2743S
2187:. Weinheim: Wiley-VCH.
2105:"Γber die Synthese des
1983:[On arginine].
1402:adenosine monophosphate
1400:(ATP) is hydrolyzed to
1390:argininosuccinate lyase
1133:Guanidinopropionic acid
1075:5110 mg/kg (rat, oral)
944:β3.7396ββ3.7370 MJ mol
793:14.87 g/100 mL (20 Β°C)
6149:Glucogenic amino acids
6050:L-Type calcium channel
4797:Cysteine sulfinic acid
4643:conversion to cysteine
4400:Formiminoglutamic acid
4327:3-Phosphoglyceric acid
4204:Ξ²-Methylglutaconyl-CoA
3676:NIST Chemistry Webbook
3407:American Heart Journal
3165:10.1210/jcem-67-6-1186
1610:
1423:
1422:Arginine biosynthesis.
1398:adenosine triphosphate
1101:Related alkanoic acids
64:
50:
5654:Cindunistat (SD-6010)
5609:2-Ethylaminoguanidine
5366:Spermine/NO (SPER/NO)
5163:O-Nitroso compounds (
4529:Ξ±-Ketoisovaleric acid
4184:Ξ²-Ketoisocaproic acid
4179:Ξ±-Ketoisocaproic acid
3342:10.1093/ajhp/58.4.298
2983:Kleanthous C (2000).
1714:Supplementation with
1604:
1444:proximal tubule cells
1421:
917:β624.9ββ622.3 kJ mol
63:
49:
6040:receptor antagonists
5713:Ronopterin (VAS-203)
5412:Molsidomine (SIN-10)
5333:(diazeniumdiolates):
5313:Roussin's black salt
5026:Mannitol hexanitrate
4616:-Adenosyl methionine
4199:Ξ²-Methylcrotonyl-CoA
4189:Ξ²-Ketoisocaproyl-CoA
4145:Ξ²-Hydroxybutyryl-CoA
3370:Integrative Medicine
2127:-valeric acid].
1947:Apel F (July 2015).
1755:Raynaud's phenomenon
1681:herpes simplex virus
1335:essential amino acid
1176:Arginine (data page)
803:slightly soluble in
54:Ball-and-stick model
5407:Linsidomine (SIN-1)
5304:Nitrosyl compounds:
5271:S-Nitrosodiclofenac
5241:S-Nitrosated AR545C
5226:S-Nitroso compounds
4789:Cysteine metabolism
4578:2-Methylbutyryl-CoA
4270:2-Aminomuconic acid
4250:3-Hydroxykynurenine
3500:10.1038/tp.2016.144
3335:(4): 298β300, 304.
2765:2014NatSR...4E4548K
2352:Borlase BC (1994).
1981:"Ueber das Arginin"
1961:on 17 November 2015
1703:High blood pressure
1628:group, which has a
1532:autoimmune diseases
1304:synthesis of 1910.
1209:with the formula (H
788:Solubility in water
743: gΒ·mol
228:Beilstein Reference
68:Space-filling model
21:
5318:Roussin's red salt
5175:Cyclohexyl nitrite
5066:Nipradilol (K-351)
4676:Ξ±-Ketobutyric acid
4653:Ξ±-Ketobutyric acid
4491:Ξ³-Glutamylcysteine
4235:β²-Formylkynurenine
4120:Ξ±-Aminoadipic acid
4031:Dehydroamino acids
3991:Encoded (proteins)
3927:Negative charge (p
3886:Positive charge (p
2753:Scientific Reports
2322:Skipper A (1998).
1785:Arginine glutamate
1773:prescription drugs
1718:-arginine reduces
1611:
1540:methyltransferases
1424:
1362:protein catabolism
1241:-arginine (symbol
1191:Infobox references
1095:Related compounds
519:L: CF1934200
65:
51:
19:
6159:Basic amino acids
6154:Alpha-Amino acids
6131:
6130:
5956:
5947:
5930:
5929:
5863:
5841:
5840:
5761:
5757:
5748:
5744:
5741:N-(1-Iminoethyl)-
5707:
5703:
5694:
5690:
5687:N-(1-Iminoethyl)-
5681:
5677:
5674:N-(1-Iminoethyl)-
5614:2-Iminopiperidine
5570:
5566:
5557:
5553:
5544:
5466:
5195:Isopropyl nitrite
5141:Nitroso compounds
4983:
4968:
4967:
4809:
4808:
4805:
4804:
4776:
4775:
4750:
4749:
4737:Homogentisic acid
4703:
4702:
4695:Methylmalonyl-CoA
4499:
4498:
4360:
4359:
4283:
4282:
4040:
4039:
4001:Non-proteinogenic
3974:
3973:
3661:978-1-119-25088-3
2774:10.1038/srep04548
2505:978-1-62703-167-7
2475:978-1-4504-1487-6
2448:978-1-118-81108-5
2418:978-0-309-03496-8
2365:978-0-412-98471-6
2355:Enteral Nutrition
2335:978-0-8342-0920-6
2086:Cohen JB (1919).
1901:978-0-08-052503-7
1834:on 9 October 2008
1710:
1670:
1588:
1394:argininosuccinate
1199:Chemical compound
1197:
1196:
1153:Related compounds
1127:
1115:
1081:Safety data sheet
1028:Hazard statements
975:
579:CompTox Dashboard
524:
406:
386:L: 230-571-3
244:
238:
233:1725411, 1725412
197:Interactive image
185:Interactive image
177:Interactive image
169:Interactive image
74:
73:
6176:
6057:dihydropyridines
5957:-arginine (NOHA)
5954:
5945:
5899:alpha aminoacids
5869:chlorogenic acid
5864:-arginine (NOHA)
5861:
5759:
5755:
5746:
5742:
5705:
5701:
5692:
5688:
5679:
5675:
5568:
5564:
5555:
5551:
5542:
5496:3-Chloroindazole
5479:
5470:
5460:
5158:
5157:
5095:Nitrofluvastatin
5079:
5078:
5021:Itramin tosilate
4977:
4890:
4836:
4829:
4822:
4813:
4785:
4715:
4629:
4628:
4516:
4377:
4309:
4294:
4245:Anthranilic acid
4125:2-Oxoadipic acid
4097:
4067:
4060:
4053:
4044:
3763:
3753:
3710:
3703:
3696:
3687:
3665:
3637:
3636:
3634:
3633:
3622:
3613:
3612:
3584:
3578:
3577:
3544:(1β2): 139β141.
3529:
3523:
3522:
3512:
3502:
3478:
3472:
3471:
3461:
3437:
3431:
3430:
3402:
3396:
3395:
3385:
3361:
3355:
3354:
3344:
3320:
3314:
3313:
3303:
3293:
3269:
3263:
3262:
3234:
3228:
3227:
3191:
3185:
3184:
3148:
3142:
3131:
3125:
3124:
3114:
3103:10.1002/pro.2647
3082:
3076:
3075:
3065:
3055:
3031:
3025:
3019:
3013:
3007:
3001:
3000:
2980:
2974:
2973:
2953:
2944:
2943:
2919:
2909:
2903:
2902:
2892:
2867:(4): 1568β1573.
2852:
2846:
2845:
2827:
2803:
2797:
2796:
2786:
2776:
2744:
2738:
2737:
2727:
2703:
2697:
2696:
2686:
2662:
2656:
2655:
2619:
2613:
2612:
2584:
2578:
2577:
2557:
2551:
2550:
2540:
2516:
2510:
2509:
2489:
2480:
2479:
2459:
2453:
2452:
2432:
2423:
2422:
2403:
2397:
2396:
2376:
2370:
2369:
2349:
2340:
2339:
2319:
2313:
2312:
2310:
2308:
2292:
2286:
2285:
2275:
2251:
2245:
2244:
2216:
2207:
2206:
2178:
2172:
2171:
2151:
2145:
2144:
2100:
2094:
2093:
2083:
2077:
2076:
2067:(3): 3191β3194.
2052:
2046:
2044:
2035:(3): 2879β2882.
2020:
2014:
2013:
2011:
2009:
1999:
1993:
1992:
1976:
1970:
1969:
1967:
1966:
1960:
1954:. Archived from
1953:
1944:
1938:
1937:
1935:
1912:
1906:
1905:
1885:
1874:
1873:
1871:
1870:
1850:
1844:
1843:
1841:
1839:
1824:
1805:of arginine and
1761:Raynaud syndrome
1717:
1708:
1668:
1608:
1586:
1583:vascular disease
1552:second messenger
1513:hydrogen bonding
1428:epithelial cells
1240:
1143:Pantothenic acid
1125:
1113:
1090:
1049:
1035:
1007:
971:
969:
940:
913:
886:
862:
847:Thermochemistry
742:
727:
721:
715:
709:
702:Chemical formula
604:
603:
587:
585:
569:
561:
553:
545:
520:
503:
495:
487:
475:
464:
447:
426:
402:
396:Gmelin Reference
379:
371:
360:
349:
328:
320:
312:
291:
283:
262:
240:
234:
218:
199:
187:
179:
171:
146:
138:
130:
122:
42:
33:Skeletal formula
29:
22:
6184:
6183:
6179:
6178:
6177:
6175:
6174:
6173:
6134:
6133:
6132:
6127:
6113:
6077:PDE5 inhibitors
6039:
6003:
5990:
5926:
5903:
5837:
5771:
5722:
5590:
5516:7-Nitroindazole
5511:6-Nitroindazole
5506:5-Nitroindazole
5459:
5451:
5228:(thionitrites):
5156:
5153:
5152:
5151:
5115:Propatylnitrate
5077:
5074:
5073:
5072:
4976:
4964:
4879:
4851:
4840:
4810:
4801:
4772:
4746:
4699:
4680:
4661:
4626:
4625:
4592:
4558:
4539:Methacrylyl-CoA
4509:
4495:
4467:
4428:
4409:
4372:Ξ±-ketoglutarate
4370:
4356:
4347:Phosphocreatine
4316:
4302:
4279:
4213:
4149:
4082:
4071:
4041:
4036:
4035:
4016:Secondary amino
3970:
3933:
3922:
3892:
3881:
3847:
3814:
3754:
3745:
3719:
3714:
3672:
3662:
3649:
3646:
3641:
3640:
3631:
3629:
3624:
3623:
3616:
3586:
3585:
3581:
3531:
3530:
3526:
3480:
3479:
3475:
3439:
3438:
3434:
3404:
3403:
3399:
3363:
3362:
3358:
3322:
3321:
3317:
3271:
3270:
3266:
3251:10.1139/h11-035
3236:
3235:
3231:
3193:
3192:
3188:
3150:
3149:
3145:
3132:
3128:
3091:Protein Science
3084:
3083:
3079:
3033:
3032:
3028:
3020:
3016:
3008:
3004:
2997:
2982:
2981:
2977:
2970:
2955:
2954:
2947:
2932:
2911:
2910:
2906:
2854:
2853:
2849:
2805:
2804:
2800:
2746:
2745:
2741:
2705:
2704:
2700:
2664:
2663:
2659:
2621:
2620:
2616:
2586:
2585:
2581:
2574:
2559:
2558:
2554:
2518:
2517:
2513:
2506:
2491:
2490:
2483:
2476:
2461:
2460:
2456:
2449:
2434:
2433:
2426:
2419:
2405:
2404:
2400:
2393:
2378:
2377:
2373:
2366:
2351:
2350:
2343:
2336:
2321:
2320:
2316:
2306:
2304:
2294:
2293:
2289:
2253:
2252:
2248:
2218:
2217:
2210:
2203:
2180:
2179:
2175:
2153:
2152:
2148:
2117:-valeriansΓ€ure"
2102:
2101:
2097:
2085:
2084:
2080:
2054:
2053:
2049:
2022:
2021:
2017:
2007:
2005:
2001:
2000:
1996:
1978:
1977:
1973:
1964:
1962:
1958:
1951:
1946:
1945:
1941:
1914:
1913:
1909:
1902:
1887:
1886:
1877:
1868:
1866:
1852:
1851:
1847:
1837:
1835:
1826:
1825:
1821:
1816:
1781:
1768:
1757:
1740:
1732:weight at birth
1715:
1705:
1696:herpes labialis
1677:
1661:
1656:
1636:
1606:
1599:
1548:
1526:process called
1500:
1484:immune function
1472:
1432:small intestine
1378:
1347:small intestine
1331:
1329:Dietary sources
1315:
1310:
1278:
1238:
1236:
1228:
1224:
1220:
1216:
1212:
1200:
1193:
1188:
1165:
1154:
1147:
1102:
1086:
1072:
1066:
1044:
1030:
1016:
1000:
958:
941:
938:
932:
928:
925:
924:Std enthalpy of
914:
911:
905:
901:
898:
897:Std enthalpy of
887:
884:
877:
874:
863:
856:
838:
807:
790:
751:White crystals
740:
730:
724:
718:
712:
704:
690:
687:
678:
673:
668:
663:
658:
657:
646:
643:
642:
636:
635:
629:
628:
625:
619:
618:
607:
588:
581:
572:
527:
506:
476:
450:
429:
415:
398:
389:
352:
331:
294:
265:
230:
221:
202:
160:
149:
111:
97:
89:
70:
56:
36:
30:
17:
12:
11:
5:
6182:
6180:
6172:
6171:
6166:
6161:
6156:
6151:
6146:
6136:
6135:
6129:
6128:
6118:
6115:
6114:
6112:
6111:
6101:
6098:
6091:
6084:
6074:
6064:
6047:
6037:
6033:
6018:ACE inhibitors
6011:
6010:
6005:
6001:
5997:
5992:
5988:
5984:
5979:
5974:
5969:
5960:
5959:
5950:
5938:
5936:
5932:
5931:
5928:
5927:
5925:
5924:
5919:
5913:
5911:
5905:
5904:
5902:
5901:
5896:
5891:
5886:
5881:
5876:
5871:
5866:
5857:
5851:
5849:
5843:
5842:
5839:
5838:
5836:
5835:
5830:
5825:
5820:
5815:
5810:
5805:
5800:
5795:
5790:
5785:
5779:
5777:
5773:
5772:
5770:
5769:
5764:
5751:
5738:
5732:
5730:
5724:
5723:
5721:
5720:
5715:
5710:
5697:
5684:
5671:
5666:
5661:
5656:
5651:
5646:
5641:
5636:
5631:
5626:
5621:
5616:
5611:
5606:
5600:
5598:
5592:
5591:
5589:
5588:
5583:
5578:
5573:
5560:
5547:
5538:
5533:
5528:
5523:
5518:
5513:
5508:
5503:
5498:
5493:
5487:
5485:
5476:
5467:
5453:
5452:
5450:
5449:
5444:
5439:
5434:
5429:
5420:
5419:
5414:
5409:
5404:
5389:
5374:
5373:
5368:
5363:
5358:
5353:
5348:
5343:
5338:
5326:
5325:
5320:
5315:
5300:
5299:
5283:
5278:
5273:
5268:
5263:
5258:
5253:
5248:
5243:
5238:
5233:
5221:-Butyl nitrite
5215:
5213:Pentyl nitrite
5210:
5208:-Butyl nitrite
5202:
5200:Methyl nitrite
5197:
5192:
5187:
5182:
5177:
5172:
5165:alkyl nitrites
5154:
5136:
5135:
5130:
5127:
5122:
5117:
5112:
5107:
5102:
5097:
5092:
5087:
5082:
5075:
5068:
5063:
5058:
5053:
5048:
5043:
5038:
5033:
5028:
5023:
5018:
5013:
5008:
5003:
4998:
4986:
4984:
4970:
4969:
4966:
4965:
4963:
4962:
4953:
4952:
4947:
4942:
4937:
4932:
4927:
4922:
4917:
4912:
4907:
4898:
4896:
4887:
4881:
4880:
4878:
4877:
4872:
4867:
4861:
4859:
4853:
4852:
4841:
4839:
4838:
4831:
4824:
4816:
4807:
4806:
4803:
4802:
4800:
4799:
4793:
4791:
4782:
4778:
4777:
4774:
4773:
4771:
4770:
4761:
4759:
4752:
4751:
4748:
4747:
4745:
4744:
4739:
4734:
4728:
4726:
4712:
4705:
4704:
4701:
4700:
4698:
4697:
4691:
4689:
4682:
4681:
4679:
4678:
4672:
4670:
4663:
4662:
4660:
4659:
4650:
4638:
4637:
4632:
4618:
4603:
4601:
4594:
4593:
4591:
4590:
4585:
4580:
4575:
4569:
4567:
4560:
4559:
4557:
4556:
4551:
4546:
4541:
4536:
4534:Isobutyryl-CoA
4531:
4525:
4523:
4513:
4501:
4500:
4497:
4496:
4494:
4493:
4475:
4473:
4469:
4468:
4466:
4465:
4460:
4455:
4450:
4445:
4439:
4437:
4430:
4429:
4427:
4426:
4420:
4418:
4411:
4410:
4408:
4407:
4402:
4397:
4392:
4386:
4384:
4374:
4362:
4361:
4358:
4357:
4355:
4354:
4349:
4344:
4330:
4329:
4323:
4321:
4306:
4291:
4285:
4284:
4281:
4280:
4278:
4277:
4272:
4267:
4262:
4257:
4252:
4247:
4242:
4237:
4228:
4226:
4215:
4214:
4212:
4211:
4206:
4201:
4196:
4191:
4186:
4181:
4176:
4174:Isovaleryl-CoA
4171:
4166:
4160:
4158:
4151:
4150:
4148:
4147:
4142:
4137:
4135:Glutaconyl-CoA
4132:
4127:
4122:
4117:
4112:
4106:
4104:
4094:
4084:
4083:
4072:
4070:
4069:
4062:
4055:
4047:
4038:
4037:
4034:
4033:
4028:
4023:
4018:
4013:
4008:
4003:
3998:
3993:
3980:
3979:
3976:
3975:
3972:
3971:
3969:
3968:
3962:
3956:
3953:Selenocysteine
3950:
3944:
3937:
3935:
3931:
3924:
3923:
3921:
3920:
3915:
3909:
3903:
3896:
3894:
3890:
3883:
3882:
3880:
3879:
3874:
3869:
3864:
3858:
3856:
3849:
3848:
3846:
3845:
3840:
3835:
3830:
3824:
3822:
3816:
3815:
3813:
3812:
3807:
3802:
3797:
3792:
3786:
3781:
3771:
3769:
3760:
3756:
3755:
3748:
3746:
3744:
3743:
3738:
3733:
3727:
3725:
3724:General topics
3721:
3720:
3715:
3713:
3712:
3705:
3698:
3690:
3684:
3683:
3678:
3671:
3670:External links
3668:
3667:
3666:
3660:
3645:
3642:
3639:
3638:
3614:
3579:
3524:
3473:
3432:
3397:
3356:
3315:
3284:(3): 609β613.
3264:
3229:
3186:
3143:
3126:
3077:
3026:
3024:, p. 176.
3014:
3012:, p. 275.
3002:
2995:
2975:
2968:
2945:
2931:978-0805330663
2930:
2904:
2847:
2798:
2759:(4548): 4548.
2739:
2698:
2657:
2614:
2579:
2572:
2552:
2511:
2504:
2481:
2474:
2454:
2447:
2424:
2417:
2398:
2391:
2371:
2364:
2341:
2334:
2314:
2287:
2246:
2227:(9): 439β445.
2208:
2202:978-3527306732
2201:
2173:
2146:
2135:(1): 643β651.
2095:
2078:
2047:
2015:
1994:
1971:
1939:
1907:
1900:
1875:
1845:
1818:
1817:
1815:
1812:
1811:
1810:
1792:
1787:
1780:
1777:
1767:
1764:
1756:
1753:
1739:
1736:
1704:
1701:
1676:
1673:
1665:growth hormone
1660:
1659:Growth hormone
1657:
1655:
1652:
1648:hydrogen bonds
1634:
1598:
1595:
1547:
1544:
1528:citrullination
1499:
1496:
1492:blood pressure
1471:
1468:
1377:
1374:
1330:
1327:
1314:
1311:
1309:
1306:
1277:
1274:
1234:
1226:
1222:
1218:
1214:
1213:N)(HN)CN(H)(CH
1210:
1198:
1195:
1194:
1189:
1185:standard state
1182:
1179:
1178:
1172:
1171:
1167:
1166:
1164:
1163:
1157:
1155:
1152:
1149:
1148:
1146:
1145:
1140:
1135:
1130:
1118:
1116:-aspartic acid
1105:
1103:
1100:
1097:
1096:
1092:
1091:
1084:
1077:
1076:
1073:
1064:
1062:
1059:
1058:
1051:
1050:
1048:P305+P351+P338
1045:
1040:
1037:
1036:
1031:
1026:
1023:
1022:
1017:
1012:
1009:
1008:
1001:
996:
993:
992:
982:
981:
977:
976:
959:
954:
951:
950:
946:
945:
942:
936:
930:
922:
919:
918:
915:
909:
903:
895:
892:
891:
890:250.6 J K mol
888:
882:
871:
868:
867:
864:
852:
849:
848:
844:
843:
840:
836:
826:
825:
822:
813:
812:
801:
795:
794:
791:
786:
783:
782:
779:
773:
772:
769:
763:
762:
759:
753:
752:
749:
745:
744:
738:
732:
731:
728:
722:
716:
710:
705:
700:
697:
696:
692:
691:
689:
688:
681:
679:
676:
674:
671:
669:
666:
664:
661:
653:
652:
651:
648:
647:
645:
644:
640:
639:
637:
633:
632:
630:
626:
623:
622:
614:
613:
612:
609:
608:
606:
605:
591:
589:
577:
574:
573:
571:
570:
562:
554:
546:
537:
535:
529:
528:
526:
525:
516:
514:
508:
507:
505:
504:
496:
488:
479:
477:
469:
466:
465:
458:
452:
451:
449:
448:
439:
437:
431:
430:
428:
427:
418:
416:
411:
408:
407:
399:
394:
391:
390:
388:
387:
383:
381:
373:
372:
362:
354:
353:
351:
350:
341:
339:
333:
332:
330:
329:
321:
313:
304:
302:
296:
295:
293:
292:
284:
275:
273:
267:
266:
264:
263:
254:
252:
246:
245:
231:
226:
223:
222:
220:
219:
210:
208:
204:
203:
201:
200:
188:
180:
172:
163:
161:
154:
151:
150:
148:
147:
139:
131:
123:
114:
112:
107:
104:
103:
99:
98:
95:
91:
90:
87:
81:
80:
76:
75:
72:
71:
66:
57:
52:
38:
37:
31:
15:
13:
10:
9:
6:
4:
3:
2:
6181:
6170:
6167:
6165:
6162:
6160:
6157:
6155:
6152:
6150:
6147:
6145:
6142:
6141:
6139:
6126:
6125:
6122:
6116:
6109:
6105:
6102:
6099:
6096:
6092:
6089:
6085:
6082:
6078:
6075:
6072:
6068:
6065:
6062:
6058:
6054:
6051:
6048:
6045:
6041:
6034:
6031:
6027:
6023:
6019:
6016:
6013:
6012:
6009:
6006:
6004:
5998:
5996:
5993:
5991:
5985:
5983:
5980:
5978:
5975:
5973:
5970:
5968:
5965:
5962:
5961:
5958:
5951:
5949:
5943:
5940:
5939:
5937:
5933:
5923:
5920:
5918:
5917:Calmidazolium
5915:
5914:
5912:
5910:
5906:
5900:
5897:
5895:
5892:
5890:
5887:
5885:
5882:
5880:
5877:
5875:
5872:
5870:
5867:
5865:
5858:
5856:
5853:
5852:
5850:
5848:
5844:
5834:
5831:
5829:
5826:
5824:
5821:
5819:
5816:
5814:
5811:
5809:
5806:
5804:
5801:
5799:
5796:
5794:
5791:
5789:
5786:
5784:
5781:
5780:
5778:
5774:
5768:
5765:
5763:
5752:
5750:
5739:
5737:
5734:
5733:
5731:
5729:
5725:
5719:
5716:
5714:
5711:
5709:
5698:
5696:
5685:
5683:
5672:
5670:
5667:
5665:
5662:
5660:
5657:
5655:
5652:
5650:
5647:
5645:
5642:
5640:
5637:
5635:
5632:
5630:
5627:
5625:
5622:
5620:
5617:
5615:
5612:
5610:
5607:
5605:
5602:
5601:
5599:
5597:
5593:
5587:
5584:
5582:
5579:
5577:
5574:
5572:
5561:
5559:
5548:
5546:
5539:
5537:
5534:
5532:
5529:
5527:
5524:
5522:
5519:
5517:
5514:
5512:
5509:
5507:
5504:
5502:
5499:
5497:
5494:
5492:
5489:
5488:
5486:
5484:
5480:
5477:
5475:
5471:
5468:
5464:
5458:
5454:
5448:
5445:
5443:
5440:
5438:
5435:
5433:
5430:
5428:
5425:
5422:
5421:
5418:
5415:
5413:
5410:
5408:
5405:
5403:
5400:
5398:
5393:
5390:
5388:
5385:
5383:
5379:
5376:
5375:
5372:
5369:
5367:
5364:
5362:
5359:
5357:
5354:
5352:
5349:
5347:
5344:
5342:
5339:
5337:
5334:
5332:
5328:
5327:
5324:
5321:
5319:
5316:
5314:
5311:
5309:
5305:
5302:
5301:
5298:
5295:
5293:
5287:
5284:
5282:
5279:
5277:
5274:
5272:
5269:
5267:
5264:
5262:
5259:
5257:
5254:
5252:
5249:
5247:
5244:
5242:
5239:
5237:
5234:
5232:
5229:
5227:
5222:
5220:
5216:
5214:
5211:
5209:
5207:
5203:
5201:
5198:
5196:
5193:
5191:
5188:
5186:
5185:Hexyl nitrite
5183:
5181:
5180:Ethyl nitrite
5178:
5176:
5173:
5171:
5168:
5166:
5160:
5148:
5146:
5142:
5138:
5137:
5134:
5131:
5128:
5126:
5123:
5121:
5118:
5116:
5113:
5111:
5108:
5106:
5103:
5101:
5098:
5096:
5093:
5091:
5088:
5086:
5083:
5081:
5069:
5067:
5064:
5062:
5059:
5057:
5054:
5052:
5049:
5047:
5044:
5042:
5039:
5037:
5034:
5032:
5029:
5027:
5024:
5022:
5019:
5017:
5014:
5012:
5009:
5007:
5004:
5002:
4999:
4997:
4994:
4992:
4988:
4987:
4985:
4981:
4975:
4971:
4961:
4958:
4955:
4954:
4951:
4948:
4946:
4943:
4941:
4938:
4936:
4933:
4931:
4928:
4926:
4923:
4921:
4918:
4916:
4913:
4911:
4908:
4906:
4903:
4900:
4899:
4897:
4895:
4891:
4888:
4886:
4882:
4876:
4873:
4871:
4868:
4866:
4863:
4862:
4860:
4858:
4854:
4850:
4847:
4844:
4837:
4832:
4830:
4825:
4823:
4818:
4817:
4814:
4798:
4795:
4794:
4792:
4790:
4786:
4783:
4779:
4769:
4768:
4763:
4762:
4760:
4758:
4753:
4743:
4740:
4738:
4735:
4733:
4730:
4729:
4727:
4724:
4720:
4719:phenylalanine
4716:
4713:
4711:
4706:
4696:
4693:
4692:
4690:
4687:
4686:propionyl-CoA
4683:
4677:
4674:
4673:
4671:
4668:
4664:
4658:
4654:
4651:
4649:
4648:Cystathionine
4646:
4644:
4640:
4639:
4636:
4633:
4631:
4630:-homocysteine
4623:
4619:
4617:
4615:
4611:
4609:
4605:
4604:
4602:
4599:
4595:
4589:
4586:
4584:
4581:
4579:
4576:
4574:
4571:
4570:
4568:
4565:
4561:
4555:
4552:
4550:
4547:
4545:
4542:
4540:
4537:
4535:
4532:
4530:
4527:
4526:
4524:
4521:
4517:
4514:
4512:
4507:
4506:propionyl-CoA
4502:
4492:
4488:
4484:
4480:
4477:
4476:
4474:
4470:
4464:
4461:
4459:
4456:
4454:
4451:
4449:
4446:
4444:
4441:
4440:
4438:
4435:
4431:
4425:
4422:
4421:
4419:
4416:
4412:
4406:
4403:
4401:
4398:
4396:
4393:
4391:
4390:Urocanic acid
4388:
4387:
4385:
4382:
4378:
4375:
4373:
4368:
4363:
4353:
4350:
4348:
4345:
4343:
4339:
4335:
4332:
4331:
4328:
4325:
4324:
4322:
4319:
4314:
4310:
4307:
4305:
4300:
4295:
4292:
4290:
4286:
4276:
4273:
4271:
4268:
4266:
4263:
4261:
4258:
4256:
4253:
4251:
4248:
4246:
4243:
4241:
4238:
4236:
4234:
4230:
4229:
4227:
4224:
4220:
4216:
4210:
4207:
4205:
4202:
4200:
4197:
4195:
4192:
4190:
4187:
4185:
4182:
4180:
4177:
4175:
4172:
4170:
4167:
4165:
4162:
4161:
4159:
4156:
4152:
4146:
4143:
4141:
4138:
4136:
4133:
4131:
4128:
4126:
4123:
4121:
4118:
4116:
4113:
4111:
4108:
4107:
4105:
4102:
4098:
4095:
4093:
4089:
4085:
4081:
4078:
4075:
4068:
4063:
4061:
4056:
4054:
4049:
4048:
4045:
4032:
4029:
4027:
4026:D-amino acids
4024:
4022:
4019:
4017:
4014:
4012:
4009:
4007:
4004:
4002:
3999:
3997:
3994:
3992:
3988:
3986:
3982:
3981:
3977:
3966:
3963:
3960:
3957:
3954:
3951:
3948:
3947:Glutamic acid
3945:
3942:
3941:Aspartic acid
3939:
3938:
3936:
3930:
3925:
3919:
3916:
3913:
3910:
3907:
3904:
3901:
3898:
3897:
3895:
3889:
3884:
3878:
3875:
3873:
3870:
3868:
3865:
3863:
3860:
3859:
3857:
3854:
3850:
3844:
3843:Phenylalanine
3841:
3839:
3836:
3834:
3831:
3829:
3826:
3825:
3823:
3821:
3817:
3811:
3808:
3806:
3803:
3801:
3798:
3796:
3793:
3790:
3787:
3785:
3782:
3780:
3776:
3773:
3772:
3770:
3768:
3764:
3761:
3759:By properties
3757:
3752:
3742:
3739:
3737:
3734:
3732:
3729:
3728:
3726:
3722:
3718:
3711:
3706:
3704:
3699:
3697:
3692:
3691:
3688:
3682:
3679:
3677:
3674:
3673:
3669:
3663:
3657:
3653:
3648:
3647:
3643:
3627:
3621:
3619:
3615:
3610:
3606:
3602:
3598:
3595:(3): 376β99.
3594:
3590:
3583:
3580:
3575:
3571:
3567:
3563:
3559:
3555:
3551:
3547:
3543:
3539:
3535:
3528:
3525:
3520:
3516:
3511:
3506:
3501:
3496:
3492:
3488:
3484:
3477:
3474:
3469:
3465:
3460:
3455:
3451:
3447:
3443:
3436:
3433:
3428:
3424:
3420:
3416:
3413:(6): 959β65.
3412:
3408:
3401:
3398:
3393:
3389:
3384:
3379:
3375:
3371:
3367:
3360:
3357:
3352:
3348:
3343:
3338:
3334:
3330:
3326:
3319:
3316:
3311:
3307:
3302:
3297:
3292:
3287:
3283:
3279:
3275:
3268:
3265:
3260:
3256:
3252:
3248:
3245:(3): 405β11.
3244:
3240:
3233:
3230:
3225:
3221:
3217:
3213:
3209:
3205:
3201:
3197:
3190:
3187:
3182:
3178:
3174:
3170:
3166:
3162:
3159:(6): 1186β9.
3158:
3154:
3147:
3144:
3141:
3137:
3136:
3130:
3127:
3122:
3118:
3113:
3108:
3104:
3100:
3097:(5): 752β61.
3096:
3092:
3088:
3081:
3078:
3073:
3069:
3064:
3059:
3054:
3049:
3045:
3041:
3037:
3030:
3027:
3023:
3018:
3015:
3011:
3006:
3003:
2998:
2996:9780199637607
2992:
2988:
2987:
2979:
2976:
2971:
2969:9780470026199
2965:
2961:
2960:
2952:
2950:
2946:
2941:
2937:
2933:
2927:
2923:
2918:
2917:
2908:
2905:
2900:
2896:
2891:
2886:
2882:
2878:
2874:
2870:
2866:
2862:
2858:
2851:
2848:
2843:
2839:
2835:
2831:
2826:
2821:
2817:
2813:
2809:
2802:
2799:
2794:
2790:
2785:
2780:
2775:
2770:
2766:
2762:
2758:
2754:
2750:
2743:
2740:
2735:
2731:
2726:
2721:
2717:
2713:
2709:
2702:
2699:
2694:
2690:
2685:
2680:
2677:(3): 521β31.
2676:
2672:
2668:
2661:
2658:
2653:
2649:
2645:
2641:
2637:
2633:
2630:(6): 419β23.
2629:
2625:
2618:
2615:
2610:
2606:
2602:
2598:
2594:
2590:
2583:
2580:
2575:
2573:9782889196227
2569:
2565:
2564:
2556:
2553:
2548:
2544:
2539:
2534:
2530:
2526:
2522:
2515:
2512:
2507:
2501:
2497:
2496:
2488:
2486:
2482:
2477:
2471:
2467:
2466:
2458:
2455:
2450:
2444:
2440:
2439:
2431:
2429:
2425:
2420:
2414:
2410:
2409:
2402:
2399:
2394:
2392:9789400957329
2388:
2384:
2383:
2375:
2372:
2367:
2361:
2357:
2356:
2348:
2346:
2342:
2337:
2331:
2327:
2326:
2318:
2315:
2303:
2302:
2297:
2291:
2288:
2283:
2279:
2274:
2269:
2266:(8): 442β51.
2265:
2261:
2257:
2250:
2247:
2242:
2238:
2234:
2230:
2226:
2222:
2215:
2213:
2209:
2204:
2198:
2194:
2190:
2186:
2185:
2177:
2174:
2169:
2165:
2161:
2157:
2150:
2147:
2142:
2138:
2134:
2131:(in German).
2130:
2126:
2122:
2118:
2116:
2112:
2108:
2099:
2096:
2091:
2090:
2082:
2079:
2074:
2070:
2066:
2063:(in German).
2062:
2058:
2051:
2048:
2042:
2038:
2034:
2031:(in German).
2030:
2026:
2019:
2016:
2004:
1998:
1995:
1991:(1β2): 43β65.
1990:
1986:
1982:
1975:
1972:
1957:
1950:
1943:
1940:
1934:
1929:
1925:
1921:
1917:
1911:
1908:
1903:
1897:
1893:
1892:
1884:
1882:
1880:
1876:
1864:
1860:
1856:
1849:
1846:
1833:
1829:
1823:
1820:
1813:
1808:
1804:
1800:
1796:
1793:
1791:
1788:
1786:
1783:
1782:
1778:
1776:
1774:
1765:
1763:
1762:
1752:
1749:
1745:
1744:schizophrenia
1738:Schizophrenia
1737:
1735:
1733:
1729:
1728:pre-eclampsia
1725:
1721:
1712:
1702:
1700:
1697:
1692:
1690:
1686:
1682:
1674:
1672:
1666:
1658:
1653:
1651:
1649:
1645:
1641:
1637:
1633:
1627:
1623:
1619:
1616:
1603:
1596:
1594:
1592:
1584:
1580:
1576:
1572:
1568:
1564:
1560:
1555:
1553:
1545:
1543:
1541:
1537:
1533:
1529:
1525:
1520:
1518:
1517:salt bridges.
1514:
1509:
1505:
1497:
1495:
1493:
1489:
1485:
1481:
1480:wound healing
1477:
1476:cell division
1469:
1467:
1465:
1461:
1457:
1451:
1449:
1445:
1441:
1437:
1433:
1429:
1420:
1416:
1414:
1410:
1405:
1403:
1399:
1395:
1391:
1387:
1383:
1375:
1373:
1370:
1367:
1363:
1359:
1354:
1352:
1348:
1344:
1340:
1336:
1328:
1326:
1324:
1320:
1312:
1307:
1305:
1303:
1299:
1295:
1291:
1287:
1286:Ernst Schulze
1283:
1275:
1273:
1270:
1268:
1264:
1260:
1256:
1252:
1248:
1244:
1232:
1208:
1204:
1192:
1186:
1180:
1177:
1173:
1168:
1162:
1159:
1158:
1156:
1151:
1150:
1144:
1141:
1139:
1136:
1134:
1131:
1129:
1124:-Methylamino-
1123:
1119:
1117:
1111:
1107:
1106:
1104:
1099:
1098:
1093:
1089:
1085:
1082:
1079:
1078:
1074:
1070:
1061:
1060:
1056:
1052:
1046:
1043:
1039:
1038:
1032:
1029:
1025:
1024:
1021:
1018:
1015:
1011:
1010:
1006:
1002:
999:
995:
994:
990:
988:
983:
978:
974:
968:
963:
960:
957:
953:
952:
949:Pharmacology
947:
943:
935:
927:
921:
920:
916:
908:
900:
894:
893:
889:
881:
876:
870:
869:
865:
860:
855:
854:Heat capacity
851:
850:
845:
841:
835:
831:
828:
827:
823:
821:
820:
815:
814:
811:
808:insoluble in
806:
802:
800:
797:
796:
792:
789:
785:
784:
780:
778:
777:Boiling point
775:
774:
770:
768:
767:Melting point
765:
764:
760:
758:
755:
754:
750:
747:
746:
739:
737:
734:
733:
706:
703:
699:
698:
693:
685:
680:
675:
670:
665:
660:
656:
649:
638:
631:
621:
617:
610:
602:
598:
597:DTXSID6041056
593:
592:
590:
580:
576:
575:
568:
563:
560:
555:
552:
547:
544:
539:
538:
536:
534:
531:
530:
523:
518:
517:
515:
513:
510:
509:
502:
497:
494:
489:
486:
481:
480:
478:
472:
468:
467:
463:
459:
457:
454:
453:
446:
441:
440:
438:
436:
433:
432:
425:
420:
419:
417:
414:
410:
409:
405:
400:
397:
393:
392:
385:
384:
382:
380:
375:
374:
370:
366:
363:
361:
359:ECHA InfoCard
356:
355:
348:
343:
342:
340:
338:
335:
334:
327:
322:
319:
314:
311:
306:
305:
303:
301:
298:
297:
290:
285:
282:
277:
276:
274:
272:
269:
268:
261:
256:
255:
253:
251:
248:
247:
243:
237:
232:
229:
225:
224:
217:
212:
211:
209:
206:
205:
198:
193:
189:
186:
181:
178:
173:
170:
165:
164:
162:
158:
153:
152:
145:
140:
137:
132:
129:
124:
121:
116:
115:
113:
110:
106:
105:
100:
92:
86:
82:
77:
69:
62:
58:
55:
48:
44:
43:
39:
34:
28:
23:
6120:
6119:
6095:paraxanthine
6071:beta blocker
6014:
5963:
5944:
5941:
5745:-ornithine (
5678:-ornithine (
5423:
5402:Feprosidnine
5397:Sydnonimines
5395:
5380:
5377:
5329:
5306:
5303:
5292:nitrosamines
5289:
5224:
5218:
5205:
5162:
5139:
4989:
4956:
4935:GSK-2181236A
4901:
4843:Nitric oxide
4764:
4757:oxaloacetate
4641:
4635:Homocysteine
4621:
4613:
4606:
4511:succinyl-CoA
4433:
4342:Glycocyamine
4275:Glutaryl-CoA
4232:
4140:Crotonyl-CoA
4130:Glutaryl-CoA
4110:Saccharopine
3983:
3928:
3905:
3887:
3741:Genetic code
3651:
3630:. Retrieved
3626:"L-Arginine"
3592:
3588:
3582:
3541:
3537:
3527:
3490:
3486:
3476:
3452:(1): 88β96.
3449:
3445:
3444:. (review).
3435:
3410:
3406:
3400:
3376:(3): 42β46.
3373:
3369:
3359:
3332:
3328:
3318:
3281:
3277:
3267:
3242:
3238:
3232:
3199:
3195:
3189:
3156:
3152:
3146:
3133:
3129:
3094:
3090:
3080:
3043:
3040:Biomedicines
3039:
3029:
3017:
3005:
2985:
2978:
2958:
2916:Biochemistry
2915:
2907:
2864:
2860:
2850:
2815:
2811:
2801:
2756:
2752:
2742:
2715:
2711:
2701:
2674:
2670:
2669:. (review).
2660:
2627:
2623:
2617:
2595:(1): 52β61.
2592:
2588:
2582:
2562:
2555:
2528:
2524:
2523:. (review).
2514:
2494:
2464:
2457:
2437:
2407:
2401:
2381:
2374:
2354:
2324:
2317:
2305:. Retrieved
2299:
2290:
2263:
2259:
2258:. (review).
2249:
2224:
2220:
2182:
2176:
2159:
2155:
2149:
2132:
2128:
2124:
2120:
2114:
2110:
2106:
2098:
2088:
2081:
2064:
2060:
2050:
2032:
2028:
2018:
2006:. Retrieved
1997:
1988:
1984:
1974:
1963:. Retrieved
1956:the original
1942:
1923:
1919:
1910:
1890:
1867:. Retrieved
1858:
1848:
1836:. Retrieved
1832:the original
1822:
1769:
1758:
1741:
1713:
1706:
1693:
1678:
1662:
1631:
1612:
1556:
1549:
1521:
1501:
1488:nitric oxide
1473:
1452:
1425:
1406:
1379:
1376:Biosynthesis
1371:
1355:
1332:
1316:
1289:
1282:yellow lupin
1279:
1271:
1267:nitric oxide
1246:
1242:
1202:
1201:
1121:
1109:
1054:
1019:
986:
972:
933:
906:
879:
858:
833:
818:
564:L HCl:
521:
512:RTECS number
403:
289:ChEMBL212301
241:
235:
182:L HCl:
141:L HCl:
102:Identifiers
94:Other names
6108:simvastatin
5942:Precursors:
5879:epicatechin
5803:Indospicine
5758:-arginine (
5704:-arginine (
5639:AR-C 102222
5567:-arginine (
5554:-arginine (
5417:Sydnonimine
5150:Nitrite (NO
5133:Trolnitrate
5129:Tenitramine
5071:Nitrate (NO
4957:Inhibitors:
4940:Praliciguat
4920:BAY 60-4552
4915:BAY 41-8543
4910:BAY 41-2272
4487:glutathione
4021:Imino acids
3985:Amino acids
3918:Pyrrolysine
3855:, uncharged
3493:(8): e871.
3202:(1): 50β4.
2301:Mayo Clinic
1640:conjugation
1626:guanidinium
1591:endothelium
1538:by protein
1536:methylation
1504:amphipathic
1069:median dose
1055:Lethal dose
1014:Signal word
810:ethyl ether
748:Appearance
695:Properties
365:100.000.738
260:CHEBI:29016
85:IUPAC names
35:of arginine
6169:Urea cycle
6164:Guanidines
6138:Categories
6081:sildenafil
6061:nifedipine
5964:Cofactors:
5953:N-Hydroxy-
5860:N-Hydroxy-
5649:Canavanine
5644:BYK-191023
5463:inhibitors
5392:REC15/2739
5371:V-PYRRO/NO
5061:Nicorandil
4950:Vericiguat
4849:modulators
4767:urea cycle
4624:-Adenosyl-
4598:methionine
4583:Tiglyl-CoA
4564:isoleucine
4463:Putrescine
4458:Cadaverine
4453:Citrulline
4352:Creatinine
4240:Kynurenine
4219:tryptophan
4092:acetyl-CoA
4077:metabolism
4074:Amino acid
4011:Glucogenic
3862:Asparagine
3838:Tryptophan
3795:Methionine
3784:Isoleucine
3632:2021-05-27
3046:(8): 277.
2818:: 100042.
2307:15 January
2156:Org. Synth
1965:2017-11-06
1869:2007-05-17
1814:References
1801:are toxic
1795:Canavanine
1644:lone pairs
1618:side-chain
1615:amino acid
1585:, just as
1575:polyamines
1382:citrulline
1358:urea cycle
1343:citrulline
1319:hydrolysis
1313:Production
1302:SΓΈrensen's
1207:amino acid
1088:L-Arginine
998:Pictograms
926:combustion
799:Solubility
761:Odourless
736:Molar mass
684:Zwitterion
567:F7LTH1E20Y
559:R54Z304Z7C
551:FL26NTK3EP
548:D/L:
543:94ZLA3W45F
490:D/L:
413:IUPHAR/BPS
315:D/L:
300:ChemSpider
281:ChEMBL1485
239:, 1725413
192:Zwitterion
155:3D model (
125:D/L:
109:CAS Number
16:Amino acid
6121:See also:
6067:Nebivolol
6026:captopril
5948:-Arginine
5889:norvaline
5884:ornithine
5798:GW-273629
5754:N-Methyl-
5700:N-Methyl-
5691:-lysine (
5563:N-Propyl-
5550:N-Methyl-
5531:ARL-17477
5424:Unsorted:
4974:NO donors
4945:Riociguat
4925:BI-703704
4905:Ataciguat
4846:signaling
4667:threonine
4483:glutamate
4448:Ornithine
4381:histidine
4367:glutamate
4194:Ξ²-Leucine
4006:Ketogenic
3996:Essential
3912:Histidine
3877:Threonine
3867:Glutamine
3828:Histidine
3767:Aliphatic
3558:0300-8177
2881:0006-4971
2842:248485831
2834:2667-3940
1807:ornithine
1685:histidine
1622:aliphatic
1609:-Arginine
1597:Structure
1563:ornithine
1546:Precursor
1508:aliphatic
1440:glutamate
1436:glutamine
1409:glutamine
1339:glutamine
1298:cyanamide
1294:ornithine
1263:precursor
1231:guanidino
1161:Panthenol
989:labelling
899:formation
873:Std molar
378:EC Number
144:1119-34-2
128:7200-25-1
20:Arginine
6088:caffeine
6053:blockers
6044:bosentan
6030:losartan
5847:Arginase
5833:VAS-2381
5828:ONO-1714
5776:Unsorted
5536:Indazole
5442:FR146881
5437:FR144220
5427:Cimlanod
5382:Furoxans
5361:PROLI/NO
5331:NONOates
5281:SNO-t-PA
5145:nitrites
5056:NCX-4215
5051:NCX 4040
5046:NCX-4016
5041:NCX-2216
4991:Nitrates
4980:prodrugs
4723:tyrosine
4710:fumarate
4657:Cysteine
4479:cysteine
4443:Agmatine
4434:arginine
4338:creatine
4299:pyruvate
4115:Allysine
3965:Tyrosine
3959:Cysteine
3906:Arginine
3833:Tyrosine
3820:Aromatic
3609:18325648
3574:30249281
3566:12701823
3519:27529679
3468:23435582
3427:22137067
3392:30881246
3351:11225166
3310:14127578
3259:21574873
3224:22842434
3216:18090659
3121:25808204
3072:32781796
2940:42290721
2899:17023580
2793:24686447
2734:15465790
2693:10690324
2652:21239136
2644:14617280
2609:16207646
2547:15465778
2282:15302078
2241:12481980
1863:Archived
1799:canaline
1779:See also
1748:agmatine
1654:Research
1571:creatine
1567:agmatine
1498:Proteins
1470:Function
1253:. It is
1251:proteins
1203:Arginine
1138:Theanine
1128:-alanine
1112:-Methyl-
980:Hazards
956:ATC code
594:L:
556:D:
540:L:
498:D:
482:L:
462:Arginine
442:L:
421:L:
344:L:
337:DrugBank
323:D:
307:L:
286:D:
278:L:
257:L:
213:L:
174:D:
166:L:
136:157-06-2
133:D:
117:L:
88:Arginine
6106:(e.g.,
6104:Statins
6079:(e.g.,
6055:(e.g.,
6042:(e.g.,
6024:(e.g.,
5874:ginseng
5823:NXN-462
5818:NCX-456
5808:KD-7040
5788:CKD-712
5521:A-84643
5387:Furoxan
5286:SNO-vWF
5036:NCX-466
4885:Targets
4415:proline
4334:glycine
4313:glycine
4304:citrate
4223:alanine
4155:leucine
3967:(β10.1)
3908:(β12.5)
3902:(β10.8)
3810:Glycine
3805:Proline
3800:Alanine
3789:Leucine
3736:Peptide
3731:Protein
3644:Sources
3510:5022089
3383:6419779
3181:7488757
3173:2903866
3112:4420524
3063:7460461
2890:1794048
2784:4070089
2761:Bibcode
2008:25 July
1838:5 March
1803:analogs
1464:nitrite
1460:nitrate
1446:of the
1430:of the
1413:proline
1366:ammonia
1351:kidneys
1323:gelatin
1308:Sources
1290:Γ‘rgyros
1276:History
1257:by the
1255:encoded
1205:is the
1020:Warning
964: (
962:B05XB01
875:entropy
830:Acidity
824:β1.652
805:ethanol
741:174.204
471:PubChem
401:364938
347:DB00125
194::
120:74-79-3
5935:Others
5894:lysine
5457:Enzyme
5432:FK-409
5346:GLO/NO
5297:SIN-1A
4520:valine
4318:serine
4101:lysine
3961:(β8.3)
3955:(β5.4)
3949:(β4.1)
3943:(β3.9)
3914:(β6.1)
3900:Lysine
3872:Serine
3779:Valine
3658:
3607:
3572:
3564:
3556:
3517:
3507:
3466:
3425:
3390:
3380:
3349:
3308:
3301:277062
3298:
3257:
3222:
3214:
3179:
3171:
3119:
3109:
3070:
3060:
2993:
2966:
2938:
2928:
2897:
2887:
2879:
2840:
2832:
2791:
2781:
2732:
2691:
2650:
2642:
2607:
2570:
2545:
2502:
2472:
2445:
2415:
2389:
2362:
2332:
2280:
2239:
2199:
1898:
1689:lysine
1565:, and
1448:kidney
1411:, and
1259:codons
1083:(SDS)
655:SMILES
445:C02385
271:ChEMBL
216:B01331
207:3DMet
79:Names
5967:NADPH
5762:-NMA)
5749:-NIO)
5708:-NMA)
5695:-NIL)
5682:-NIO)
5624:AEITU
5619:1400W
5571:-NPA)
5558:-NMA)
5545:-NIO)
5231:LA810
4857:Forms
4781:Other
4472:other
3987:types
3853:Polar
3570:S2CID
3220:S2CID
3177:S2CID
2861:Blood
2838:S2CID
2648:S2CID
2162:: 4.
1959:(PDF)
1952:(PDF)
1221:CH(NH
616:InChI
501:71070
326:64224
250:ChEBI
157:JSmol
5982:Heme
5909:CAMK
5728:eNOS
5718:TRIM
5669:MITU
5664:IPTU
5659:EITU
5596:iNOS
5586:TRIM
5483:nNOS
5351:JS-K
5219:tert
4765:see
3656:ISBN
3605:PMID
3562:PMID
3554:ISSN
3515:PMID
3464:PMID
3423:PMID
3388:PMID
3347:PMID
3306:PMID
3255:PMID
3212:PMID
3169:PMID
3117:PMID
3068:PMID
2991:ISBN
2964:ISBN
2936:OCLC
2926:ISBN
2895:PMID
2877:ISSN
2830:ISSN
2789:PMID
2730:PMID
2689:PMID
2640:PMID
2605:PMID
2568:ISBN
2543:PMID
2500:ISBN
2470:ISBN
2443:ISBN
2413:ISBN
2387:ISBN
2360:ISBN
2330:ISBN
2309:2015
2278:PMID
2237:PMID
2197:ISBN
2010:2019
1896:ISBN
1840:2018
1797:and
1790:AAKG
1613:The
1559:urea
1515:and
1462:and
1438:and
1388:and
1349:and
1341:via
1296:and
1122:beta
1034:H319
817:log
757:Odor
533:UNII
485:6322
456:MeSH
435:KEGG
310:6082
5995:CaM
5977:FMN
5972:FAD
5922:W-7
5855:ABH
5634:AMT
5474:NOS
4960:ODQ
4894:sGC
3597:doi
3546:doi
3542:244
3505:PMC
3495:doi
3454:doi
3415:doi
3411:162
3378:PMC
3337:doi
3296:PMC
3286:doi
3247:doi
3204:doi
3161:doi
3107:PMC
3099:doi
3058:PMC
3048:doi
2922:180
2885:PMC
2869:doi
2865:109
2820:doi
2779:PMC
2769:doi
2720:doi
2716:134
2679:doi
2632:doi
2597:doi
2533:doi
2529:134
2268:doi
2229:doi
2189:doi
2164:doi
2137:doi
2069:doi
2037:doi
1928:doi
1924:243
1245:or
1243:Arg
1225:)CO
987:GHS
967:WHO
937:298
910:298
883:298
584:EPA
493:232
474:CID
424:721
318:227
6140::
6059::
6036:ET
6028:,
6008:Ca
5987:BH
5394:;
5294:):
5288:;
5223:;
5167:):
5161:;
4755:Gβ
4708:Gβ
4655:+
4504:Gβ
4489::
4365:Gβ
4340::
4301:β
4297:Gβ
3989::
3617:^
3603:.
3593:50
3591:.
3568:.
3560:.
3552:.
3540:.
3536:.
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3421:.
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3374:16
3372:.
3368:.
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3333:58
3331:.
3327:.
3304:.
3294:.
3282:87
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3276:.
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3200:11
3198:.
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2158:.
2133:43
2107:dl
2065:32
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1989:11
1987:.
1922:.
1918:.
1878:^
1861:.
1857:.
1734:.
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1542:.
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1065:50
1063:LD
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929:(Ξ
902:(Ξ
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832:(p
717:14
682:L
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6110:)
6097:)
6090:)
6083:)
6073:)
6069:(
6063:)
6046:)
6038:B
6032:)
6020:/
6002:2
6000:O
5989:4
5955:L
5946:L
5862:L
5760:L
5756:L
5747:L
5743:L
5706:L
5702:L
5693:L
5689:L
5680:L
5676:L
5569:L
5565:L
5556:L
5552:L
5543:L
5465:)
5461:(
5399::
5384::
5310::
5206:n
5159:)
5155:2
5147::
5143:/
5080:)
5076:3
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4982:)
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4835:e
4828:t
4821:v
4725:β
4721:β
4688:β
4669:β
4645::
4627:L
4622:S
4614:S
4610::
4600:β
4566:β
4522:β
4508:β
4485:β
4481:+
4436:β
4417:β
4383:β
4369:β
4336:β
4320:β
4315:β
4289:G
4233:N
4225:β
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4157:β
4103:β
4090:β
4088:K
4066:e
4059:t
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1126:L
1114:D
1110:N
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1067:(
973:S
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236:D
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