612:
380:
1469:. 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
1430:
1762:
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.
58:
1016:
38:
72:
3762:
1613:
1348:, 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
1761:
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
1709:
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
1461:, 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".
1678:. 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
1521:
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
1379:
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.
1356:. 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
1303:(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
1781:
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
1710:
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."
1024:
996:
1464:
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
3416:
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.
4075:
4844:
1058:
966:
3718:
4068:
2194:
1530:
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.
1959:
4837:
3162:
Alba-Roth J, MΓΌller OA, Schopohl J, von Werder K (December 1988). "Arginine stimulates growth hormone secretion by suppressing endogenous somatostatin secretion".
4061:
665:
5977:
4830:
1383:
Animal sources of arginine include meat, dairy products, and eggs, and plant sources include seeds of all types, for example grains, beans, and nuts.
1541:.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
1527:
195:
3711:
4011:
934:
4270:
3670:
3248:
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".
2514:
2484:
2457:
2427:
2374:
2344:
1910:
907:
4583:
4174:
1565:, as well as an intercellular messenger which regulates vasodilation, and also has functions in the immune system's reaction to infection.
1722:-arginine reduces blood pressure with pooled estimates of 5.4 mmHg for systolic blood pressure and 2.7 mmHg for diastolic blood pressure.
179:
207:
5606:
4179:
1702:, would interfere markedly with virus synthesis", but concludes that "no ready explanation is available for any of these observations".
187:
6154:
6032:
3704:
2940:
2211:
1517:, because at physiological pH it contains a positively charged guanidinium group, which is highly polar, at the end of a hydrophobic
5291:
3005:
2978:
2582:
2401:
1753:
Both liquid chromatography and liquid chromatography/mass spectrometric assays have found that brain tissue of deceased people with
626:
5457:
1838:
1757:
shows altered arginine metabolism. Assays also confirmed significantly reduced levels of Ξ³-aminobutyric acid (GABA), but increased
5644:
3453:"Arginine supplementation for improving maternal and neonatal outcomes in hypertensive disorder of pregnancy: a systematic review"
1426:
are bidirectional. Thus, the net use or production of these amino acids is highly dependent on cell type and developmental stage.
4970:
1364:, have reduced function, because the small bowel does the first step of the synthesizing process and the kidneys do the second.
6159:
5261:
4405:
1534:
1371:. For some carnivores, for example cats, dogs and ferrets, arginine is essential, because after a meal, their highly efficient
5366:
6046:
1336:. It is obtained commercially by fermentation. In this way, 25-35 g/liter can be produced, using glucose as a carbon source.
434:
1966:
5728:
5596:
4434:
1873:
6134:
5296:
5120:
4564:
4001:
1396:
1052:
543:
3686:
1674:
Intravenously administered arginine is used in growth hormone stimulation tests because it stimulates the secretion of
37:
5982:
5793:
5266:
5006:
4742:
4275:
1589:
589:
1015:
6169:
6164:
5865:
5751:
5684:
5551:
5130:
1640:
1201:
1131:
840:
5016:
4904:
4631:
4539:
4265:
4214:
4189:
3785:
387:
5823:
5697:
5614:
5256:
1244:
group appended to a standard amino acid framework. At physiological pH, the carboxylic acid is deprotonated (βCO
4752:
4559:
4415:
4194:
3727:
2306:
1734:
1730:
1588:(mainly through ornithine and to a lesser degree through agmatine, citrulline, and glutamate). The presence of
1119:
466:
5511:
2598:
Stechmiller JK, Childress B, Cowan L (February 2005). "Arginine supplementation and wound healing". (review).
5803:
5634:
5501:
4199:
3598:
Shao A, Hathcock JN (April 2008). "Risk assessment for the amino acids taurine, L-glutamine and L-arginine".
1505:. Arginine is necessary for T-cells to function in the body, and can lead to their deregulation if depleted.
6063:
5674:
5591:
5323:
5135:
5011:
4598:
4554:
4382:
4155:
1991:
1562:
1412:
1400:
1296:
1143:
5963:
5870:
5619:
5351:
375:
6060:
5764:
5710:
5573:
5560:
5318:
5021:
4807:
4686:
4663:
4501:
4410:
4337:
4242:
4130:
4090:
4021:
1408:
883:
5679:
5281:
5251:
1592:(ADMA), a close relative, inhibits the nitric oxide reaction; therefore, ADMA is considered a marker for
299:
5987:
5669:
5484:
5271:
4623:
4299:
4016:
4006:
2760:"Upregulation of colonic luminal polyamines produced by intestinal microbiota delays senescence in mice"
1561:
Arginine is the immediate precursor of nitric oxide, an important signaling molecule which can act as a
1466:
1404:
1273:
1038:
1008:
827:
95:
5624:
5328:
5276:
5100:
5095:
3691:
1649:
of 13.8, and is therefore always protonated and positively charged at physiological pH. Because of the
472:
291:
5909:
5506:
5246:
5115:
5105:
2819:"Understanding the association of stem cells in fetal development and carcinogenesis during pregnancy"
5521:
5516:
5346:
5333:
5286:
5110:
5036:
5026:
4098:
4087:
4026:
2771:
1691:
1454:
1345:
1186:
64:
6179:
6174:
5997:
5927:
4799:
4588:
4280:
4260:
3830:
607:
119:
78:
4945:
2633:
Witte MB, Barbul A (2003). "Arginine physiology and its implication for wound healing". (review).
5664:
5649:
5427:
5407:
5376:
5228:
5185:
4950:
4930:
4925:
4920:
4859:
4209:
3777:
3580:
3230:
3187:
2848:
2658:
1927:"IUPAC-IUB Commission on Biochemical Nomenclature A One-Letter Notation for Amino Acid Sequences"
1813:
1795:
1542:
1518:
1372:
238:
5932:
5723:
5654:
5402:
5381:
4053:
1429:
1312:
226:
5808:
5541:
4935:
4915:
2013:
5843:
5838:
5452:
5447:
5371:
5205:
5066:
5061:
5056:
5051:
4895:
4747:
4705:
4041:
3863:
3666:
3615:
3572:
3564:
3525:
3474:
3433:
3398:
3357:
3316:
3265:
3222:
3179:
3127:
3078:
3001:
2974:
2968:
2946:
2936:
2905:
2887:
2840:
2799:
2740:
2699:
2650:
2615:
2578:
2553:
2510:
2480:
2474:
2453:
2447:
2423:
2397:
2370:
2340:
2288:
2247:
2207:
2098:
1906:
1900:
1783:
1650:
1550:
1091:
57:
5833:
5828:
5818:
5798:
5531:
5046:
2995:
2572:
2504:
2417:
2391:
2364:
2334:
2267:"Arginine deficiency in preterm infants: biochemical mechanisms and nutritional implications"
5879:
5473:
5442:
5356:
5307:
5200:
5151:
5031:
4255:
4135:
3607:
3556:
3515:
3505:
3464:
3425:
3388:
3347:
3306:
3296:
3257:
3214:
3171:
3117:
3109:
3068:
3058:
2932:
2895:
2879:
2830:
2789:
2779:
2730:
2689:
2642:
2607:
2543:
2278:
2239:
2199:
2174:
2147:
2079:
2047:
1938:
1771:
1593:
1153:
798:
712:
43:
5629:
5241:
577:
569:
561:
553:
336:
6067:
5738:
5526:
5361:
5125:
4549:
4357:
1706:
1494:
1442:
1438:
1357:
1269:
1248:) and both the amino and guanidino groups are protonated, resulting in a cation. Only the
406:
320:
154:
138:
71:
635:
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
328:
146:
2970:
Bioinformatics for
Geneticists: A Bioinformatics Primer for the Analysis of Genetic Data
2775:
1926:
1870:
Recommendations on
Organic & Biochemical Nomenclature, Symbols & Terminology etc
1842:
1533:
Arginine residues in proteins can be deiminated by PAD enzymes to form citrulline, in a
611:
379:
270:
130:
6087:
5746:
5639:
5536:
5236:
5223:
5210:
4856:
4544:
4184:
4145:
3963:
3520:
3493:
3393:
3376:
3122:
3097:
3073:
3046:
2900:
2794:
2759:
1675:
1538:
1502:
1292:
1195:
3696:
3311:
3284:
2694:
2677:
2243:
1943:
6148:
6028:
5777:
5586:
5215:
5195:
5190:
5175:
4729:
4696:
4658:
4516:
4400:
4036:
3957:
3951:
3853:
3045:
Gambardella J, Khondkar W, Morelli MB, Wang X, Santulli G, Trimarco V (August 2020).
2852:
2646:
1754:
1738:
1658:
1523:
1490:
1486:
1098:
864:
787:
777:
368:
4822:
3636:
3584:
3234:
2662:
6105:
6081:
5412:
5180:
4880:
4867:
4853:
4767:
4645:
4521:
4352:
4285:
4150:
4140:
4120:
3751:
3191:
2925:
1742:
1498:
1277:
1265:
977:
972:
4204:
3150:
2283:
2266:
2203:
511:
3301:
3218:
2883:
2835:
2818:
495:
6118:
5889:
5813:
5422:
5417:
5302:
5143:
5041:
4885:
4497:
3995:
3928:
3611:
3145:
3063:
2311:
2230:
Tapiero H, MathΓ© G, Couvreur P, Tew KD (November 2002). "L-Arginine". (review).
1628:
1601:
1546:
1241:
1079:
820:
503:
3761:
2867:
2611:
2103:(2nd ed.). New York, New York, USA: Longmans, Green & Co. p. 140.
1612:
6091:
6071:
6005:
5659:
5076:
5071:
4960:
4940:
4777:
4653:
4618:
4608:
4593:
4574:
4473:
4468:
4463:
4362:
4250:
4229:
4102:
4084:
4031:
3872:
3848:
3805:
3794:
3560:
3429:
2735:
2718:
2548:
2531:
2151:
1865:
1841:. IUPAC-IUB Joint Commission on Biochemical Nomenclature. 1983. Archived from
1805:
1625:
1514:
1392:
1368:
1353:
1329:
1283:
The one-letter symbol R was assigned to arginine for its phonetic similarity.
1217:
809:
746:
694:
423:
310:
202:
3568:
3469:
3452:
2891:
2844:
2178:
2083:
2051:
1044:
6077:
6036:
5899:
5894:
4955:
4677:
4493:
4458:
4391:
4377:
3922:
3887:
3877:
3838:
3544:
3352:
3335:
2950:
2817:
Banerjee, Kasturi; Chattopadhyay, Agnibha; Banerjee, Satarupa (2022-07-01).
1817:
1695:
1654:
1636:
1632:
1585:
1573:
1450:
1446:
1419:
1349:
1308:
1304:
1171:
3619:
3576:
3529:
3478:
3437:
3402:
3361:
3320:
3269:
3226:
3175:
3131:
3082:
2909:
2803:
2744:
2703:
2654:
2619:
2557:
2292:
2251:
6111:
cGMP preferring PDE inhibitors (e.g., sildenafil, paraxanthine, tadalafil)
3183:
17:
6098:
6054:
6040:
5857:
5546:
5437:
4984:
4875:
4733:
4720:
4667:
4489:
4453:
4348:
4309:
4125:
3975:
3969:
3843:
3663:
Analysis of
Protein Post-Translational Modifications by Mass Spectrometry
1809:
1758:
1657:, the positive charge is delocalized, enabling the formation of multiple
1581:
1577:
1272:
CGU, CGC, CGA, CGG, AGA, and AGG. The guanidine group in arginine is the
1148:
347:
3510:
2866:
Rodriguez, Paulo C.; Quiceno, David G.; Ochoa, Augusto C. (2006-10-05).
1403:. This is an energetically costly process, because for each molecule of
357:
6018:
5884:
5397:
5392:
5341:
5160:
5155:
5081:
5001:
4990:
4425:
4344:
4323:
4314:
4233:
4219:
4165:
3820:
3815:
3810:
3799:
3746:
3741:
2868:"l-arginine availability regulates T-lymphocyte cell-cycle progression"
1474:
1470:
1423:
1376:
1333:
1261:
1260:) enantiomer is found naturally. Arg residues are common components of
815:
481:
388:
3545:"Oral L-arginine can reverse digital necrosis in Raynaud's phenomenon"
2784:
2449:
Nutrition and
Disease Management for Veterinary Technicians and Nurses
1497:, and the release of hormones. It is a precursor for the synthesis of
6114:
6010:
5904:
5467:
4530:
4328:
4111:
3910:
3882:
3789:
3113:
1699:
1458:
1367:
Arginine is an essential amino acid for birds, as they do not have a
1361:
281:
3261:
3205:
Kanaley JA (January 2008). "Growth hormone, arginine and exercise".
2115:
2067:
2035:
1395:
in the urea cycle by the sequential action of the cytosolic enzymes
1194:
Except where otherwise noted, data are given for materials in their
2931:(3rd ed.). San Francisco, Calif.: Benjamin Cummings. pp.
2192:
Drauz K, Grayson I, Kleemann A, et al. (2006). "Amino Acids".
1311:
in 1899, but some doubts about arginine's structure lingered until
455:
1611:
1428:
522:
260:
206:
194:
186:
178:
167:
3377:"Lysine for Herpes Simplex Prophylaxis: A Review of the Evidence"
1453:, which is secreted into the bloodstream which carries it to the
5992:
5919:
5493:
3639:. MedlinePlus, US National Institutes of Health. 13 October 2021
3285:"Amino Acid Requirements of Herpes Simplex Virus in Human Cells"
1800:
1569:
767:
445:
4826:
4057:
3700:
1545:. Another post-translational modification of arginine involves
2574:
The
Metabolic Challenges of Immune Cells in Health and Disease
1770:
Oral L-arginine has been shown to reverse digital necrosis in
2130:[On the synthesis of racemic arginine (Ξ±-amino-Ξ΄-guanido-
2014:"BIOETYMOLOGY: ORIGIN IN BIO-MEDICAL TERMS: arginine (Arg R)"
1299:
and his assistant Ernst
Steiger. He named it from the Greek
1280:. Like all amino acids, it is a white, water-soluble solid.
594:
70:
56:
3543:
Rembold, Christopher M.; Ayers, Carlos R. (February 2003).
2506:
Bioactive
Dietary Factors and Plant Extracts in Dermatology
1344:
Arginine is classified as a semiessential or conditionally
1864:
IUPAC-IUBMB Joint
Commission on Biochemical Nomenclature.
1694:
in human cells indicated that "...the lack of arginine or
1682:-arginine it did not cause an increase in growth hormone.
1866:"Nomenclature and Symbolism for Amino Acids and Peptides"
1839:"Nomenclature and Symbolism for Amino Acids and Peptides"
3207:
Current
Opinion in Clinical Nutrition and Metabolic Care
2336:
Dietitian's
Handbook of Enteral and Parenteral Nutrition
2165:
Brand E, Sandberg M (1932). "d-Arginine Hydrochloride".
1635:
straight chain, the distal end of which is capped by a
4876:
Nitroxyl anion (NO; oxonitrate(1-), hyponitrite anion)
1741:. It did not lower systolic blood pressure or improve
1737:, including women with high blood pressure as part of
3492:
Liu P, Jing Y, Collie ND, et al. (August 2016).
3096:
Fitch CA, Platzer G, Okon M, et al. (May 2015).
2509:. Springer Science & Business Media. p. 75.
2396:. Springer Science & Business Media. p. 45.
2134:-valeric acid) and of the isomeric Ξ±-guanido-Ξ΄-amino-
1705:
Further reviews conclude that "lysine's efficacy for
1477:, the stable end-products of nitric oxide breakdown.
3494:"Altered brain arginine metabolism in schizophrenia"
3164:
The Journal of Clinical Endocrinology and Metabolism
2265:
Wu G, Jaeger LA, Bazer FW, Rhoads JM (August 2004).
5945:
5918:
5856:
5786:
5737:
5605:
5492:
5483:
5466:
5367:
Methylamine hexamethylene methylamine/NO (MAHMA/NO)
4983:
4903:
4894:
4866:
4798:
4791:
4765:
4728:
4718:
4695:
4676:
4607:
4573:
4529:
4514:
4482:
4443:
4424:
4390:
4375:
4322:
4307:
4298:
4228:
4164:
4110:
4097:
3937:
3896:
3862:
3829:
3776:
3769:
3734:
3457:
Journal of the Renin-Angiotensin-Aldosterone System
2124:-valeriansΓ€ure) und der isomeren Ξ±-Guanido-Ξ΄-amino-
2056:
The structure for arginine is presented on p. 2882.
1690:Research from 1964 into amino acid requirements of
433:
2924:
5181:Amyl nitrite (isoamyl nitrite, isopentyl nitrite)
2758:Kibe R, Kurihara S, Sakai Y, et al. (2014).
2729:(10 Suppl): 2807Sβ2811S, discussion 2818Sβ2819S.
2542:(10 Suppl): 2743Sβ2747S, discussion 2765Sβ2767S.
1616:Delocalization of charge in guanidinium group of
225:
853:2.18 (carboxyl), 9.09 (amino), 13.8 (guanidino)
510:
502:
494:
5042:Naproxcinod (nitronaproxen; AZD-3582, HCT-3012)
3451:Gui S, Jia J, Niu X, et al. (March 2014).
2473:Spano MA, Kruskall LJ, Thomas DT (2017-08-30).
2100:Organic Chemistry for Advanced Students, Part 3
1501:(NO), making it important in the regulation of
645:D/L: Key: ODKSFYDXXFIFQN-UHFFFAOYSA-N
153:
145:
137:
129:
3032:
3020:
2678:"Enzymatic function of nitric oxide synthases"
2422:. National Academies Press. 1985. p. 65.
2195:Ullmann's Encyclopedia of Industrial Chemistry
2140:Berichte der Deutschen Chemischen Gesellschaft
2072:Berichte der Deutschen Chemischen Gesellschaft
2040:Berichte der Deutschen Chemischen Gesellschaft
5458:N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide
5017:Ethylene glycol dinitrate (EGDN; nitroglycol)
4838:
4069:
3712:
3250:Applied Physiology, Nutrition, and Metabolism
2369:. Jones & Bartlett Learning. p. 48.
2339:. Jones & Bartlett Learning. p. 76.
2038:[On a cleavage product of arginine].
1437:Arginine is made by the body as follows. The
1332:of various cheap sources of protein, such as
652:D: Key: ODKSFYDXXFIFQN-SCSAIBSYSA-N
8:
1600:-arginine is considered a sign of a healthy
1584:; and can also be used for the synthesis of
2923:Mathews CK, Van Holde KE, Ahern KG (2000).
2070:[On the constitution of arginine].
2034:Schulze E, Winterstein E (September 1897).
5489:
5480:
4900:
4845:
4831:
4823:
4795:
4725:
4526:
4387:
4319:
4304:
4107:
4076:
4062:
4054:
3773:
3719:
3705:
3697:
3340:American Journal of Health-System Pharmacy
3336:"Lysine for management of herpes labialis"
2225:
2223:
2036:"Ueber ein Spaltungs-product des Arginins"
610:
378:
335:
327:
319:
29:
5201:Isobutyl nitrite (2-methylpropyl nitrite)
5111:Nitroglycerin (glyceryl trinitrate (GTN))
3519:
3509:
3468:
3392:
3351:
3310:
3300:
3121:
3072:
3062:
2899:
2834:
2793:
2783:
2734:
2693:
2547:
2476:Nutrition for Sport, Exercise, and Health
2282:
2066:Schulze E, Winterstein E (October 1899).
1942:
1653:between the double bond and the nitrogen
1291:Arginine was first isolated in 1886 from
576:
568:
560:
552:
5277:S-Nitrosocysteine (SNC, CysNO, SNO-Cys)
5267:S-Nitroso-N-valerylpenicillamine (SNVP)
3000:. Oxford University Press. p. 13.
2823:Advances in Cancer Biology - Metastasis
2271:The Journal of Nutritional Biochemistry
1830:
1733:and lengthens pregnancy for women with
670:
631:
606:
471:
356:
5262:S-Nitroso-N-acetylpenicillamine (SNAP)
5136:Sodium trioxodinitrate (Angeli's salt)
3631:
3629:
3600:Regulatory Toxicology and Pharmacology
3334:Tomblin FA, Lucas KH (February 2001).
2973:. John Wiley & Sons. p. 326.
2452:. John Wiley & Sons. p. 232.
1902:Nitric Oxide: Biology and Pathobiology
1777:Safety and potential drug interactions
1415:(AMP), consuming two ATP equivalents.
792:368 Β°C (694 Β°F; 641 K)
369:
4271:2-Amino-3-carboxymuconic semialdehyde
2962:
2960:
2498:
2496:
2441:
2439:
2390:Freedland RA, Briggs S (2012-12-06).
2358:
2356:
2068:"Ueber die Constitution des Arginins"
1996:Zeitschrift fΓΌr Physiologische Chemie
1467:inducible nitric oxide synthase (NOS)
1407:that is synthesized, one molecule of
782:260 Β°C; 500 Β°F; 533 K
638:Key: ODKSFYDXXFIFQN-BYPYZUCNSA-N
298:
290:
269:
7:
6097:non-selective PDE inhibitors (e.g.,
4881:Nitric oxide (NO; nitrogen monoxide)
4584:2,3-Dihydroxy-3-methylpentanoic acid
1894:
1892:
1890:
1580:; is necessary for the synthesis of
1485:Arginine plays an important role in
976:
5121:Pentaerithrityl tetranitrate (PETN)
5007:Diethylene glycol dinitrate (DEGDN)
3728:Encoded (proteinogenic) amino acids
3549:Molecular and Cellular Biochemistry
3098:"Arginine: Its pKa value revisited"
3047:"Arginine and Endothelial Function"
2446:Wortinger A, Burns K (2015-06-11).
2393:A Biochemical Approach to Nutrition
1631:of arginine consists of a 3-carbon
1445:produce citrulline, primarily from
484:
454:
6026:Indirect/downstream NO modulators:
5794:Asymmetric dimethylarginine (ADMA)
2676:Andrew PJ, Mayer B (August 1999).
2577:. Frontiers Media SA. p. 17.
2503:Watson RR, Zibadi S (2012-11-28).
1493:, removing ammonia from the body,
25:
5824:Nitroarginine methyl ester (NAME)
5287:S-Nitrosoglutathione (GSNO, SNOG)
5257:S-Nitroso-N-acetylcysteine (SNAC)
5131:Propylene glycol dinitrate (PGDN)
4886:Nitrosonium (NO; nitrosyl cation)
3375:Mailoo VJ, Rampes S (June 2017).
2232:Biomedicine & Pharmacotherapy
1686:Herpes-Simplex Virus (Cold sores)
1568:Arginine is also a precursor for
107:2-Amino-5-guanidinopentanoic acid
3760:
2647:10.1046/j.1524-475X.2003.11605.x
2571:Mauro C, Frezza C (2015-07-13).
2532:"Enzymes of arginine metabolism"
2307:"Drugs and Supplements Arginine"
1876:from the original on 29 May 2007
1328:It is traditionally obtained by
1295:seedlings by the German chemist
1014:
730:
724:
678:D/L: C(CC(C(=O)O)N)CNC(=N)N
36:
5352:Diethylenetriamine/NO (DETA/NO)
4406:Imidazol-4-one-5-propionic acid
3661:Griffiths JR, Unwin RD (2016).
3151:Growth hormone stimulation test
2479:. Human Kinetics. p. 240.
1937:(13): 3557β3559. 10 July 1968.
1931:Journal of Biological Chemistry
1905:. Academic Press. p. 189.
1698:, and possibly the presence of
1535:post-translational modification
1418:The pathways linking arginine,
1198:(at 25 Β°C , 100 kPa).
688:L HCl: .NC(CCCNC(N)=)C()=O
5552:N-(1-Iminoethyl)-L-ornithine (
4220:Ξ²-Hydroxy Ξ²-methylglutaryl-CoA
4175:Ξ²-Hydroxy Ξ²-methylbutyric acid
2600:Nutrition in Clinical Practice
1960:"Biographie von Ernst Schulze"
736:
718:
1:
6135:Receptor/signaling modulators
5804:Guanidinoethyldisulfide (GED)
5022:Isosorbide mononitrate (ISMN)
5012:Erythritol tetranitrate (ETN)
4435:1-Pyrroline-5-carboxylic acid
4180:Ξ²-Hydroxy Ξ²-methylbutyryl-CoA
2719:"L-arginine and hypertension"
2695:10.1016/S0008-6363(99)00115-7
2635:Wound Repair and Regeneration
2419:Nutrient Requirements of Dogs
2284:10.1016/j.jnutbio.2003.11.010
2244:10.1016/s0753-3322(02)00284-6
2204:10.1002/14356007.a02_057.pub2
2120:-Arginins (Ξ±-Amino-Ξ΄-guanido-
2114:SΓΆlrensen SP (January 1910).
1990:Schulze E, Steiger E (1887).
1944:10.1016/S0021-9258(19)34176-6
1391:Arginine is synthesized from
1375:produces large quantities of
683:D: C(C(C(=O)O)N)CNC(=N)N
673:L: C(C(C(=O)O)N)CNC(=N)N
5272:S-Nitrosocaptopril (SNO-Cap)
5101:Nitroflurbiprofen (HCT-1026)
5096:Nitroatorvastatin (NCX-6560)
4565:2-Methyl-3-oxopropanoic acid
3302:10.1128/jb.87.3.609-613.1964
3283:Tankersley RW (March 1964).
3219:10.1097/MCO.0b013e3282f2b0ad
2884:10.1182/blood-2006-06-031856
2836:10.1016/j.adcanc.2022.100042
1718:A meta-analysis showed that
1397:argininosuccinate synthetase
1240:H. The molecule features a
5747:Aminoguanidine (pimagedine)
5640:Aminoguanidine (pimagedine)
5537:Aminoguanidine (pimagedine)
5301:N-Nitroso compounds (e.g.,
5116:Nitropravastatin (NCX-6550)
5027:Isosorbide dinitrate (ISDN)
4743:4-Hydroxyphenylpyruvic acid
4276:2-Aminomuconic semialdehyde
3612:10.1016/j.yrtph.2008.01.004
3064:10.3390/biomedicines8080277
2997:Protein-protein Recognition
1590:asymmetric dimethylarginine
1068:or concentration (LD, LC):
877:232.8 J K mol (at 23.7 Β°C)
52:
6196:
6033:AT-II receptor antagonists
5778:Nitroarginine (NNA, NOARG)
5615:1-Amino-2-hydroxyguanidine
5587:Nitroarginine (NNA, NOARG)
5334:Sodium nitroprusside (SNP)
4619:generation of homocysteine
3786:Branched-chain amino acids
3033:Griffiths & Unwin 2016
3021:Griffiths & Unwin 2016
2612:10.1177/011542650502000152
2530:Morris SM (October 2004).
1765:
6155:Proteinogenic amino acids
6128:
4266:3-Hydroxyanthranilic acid
3989:
3758:
3665:. John Wiley & Sons.
3430:10.1016/j.ahj.2011.09.012
2152:10.1002/cber.191004301109
1899:Ignarro LJ (2000-09-13).
1513:Arginine's side chain is
1192:
1185:
1180:
1105:
1064:
995:
990:
959:
857:
705:
697:: NC(CCCNC(N)=)C()=O
661:
622:
112:
104:
94:
89:
51:
35:
5512:3-Chloro-5-nitroindazole
5347:Diethylamine/NO (DEA/NO)
5319:Metal nitrosyl complexes
5247:S-Nitrosoalbumin (SNALB)
4941:Cinaciguat (BAY 58-2667)
4753:4-Maleylacetoacetic acid
4560:3-Hydroxyisobutyric acid
4416:Glutamate-1-semialdehyde
3498:Translational Psychiatry
3470:10.1177/1470320313475910
3146:MedlinePlus Encyclopedia
2967:Barnes MR (2007-04-16).
2723:The Journal of Nutrition
2717:Gokce N (October 2004).
2536:The Journal of Nutrition
2179:10.15227/orgsyn.012.0004
2084:10.1002/cber.18990320385
2052:10.1002/cber.18970300389
1786:and herbal supplements.
1735:gestational hypertension
1731:diastolic blood pressure
1276:for the biosynthesis of
1181:Supplementary data page
1053:Precautionary statements
6104:PDE9 inhibitors (e.g.,
5592:Pentamidine isethionate
5502:3-Bromo-7-nitroindazole
5389:Heterocyclic compounds:
4913:Activators/stimulators:
4599:2-Methylacetoacetyl-CoA
4555:3-Hydroxyisobutyryl-CoA
4091:metabolic intermediates
3692:L-arginine, Mayo Clinic
3561:10.1023/A:1022422932108
3289:Journal of Bacteriology
2736:10.1093/jn/134.10.2807S
2682:Cardiovascular Research
2549:10.1093/jn/134.10.2743S
2198:. Weinheim: Wiley-VCH.
2116:"Γber die Synthese des
1994:[On arginine].
1413:adenosine monophosphate
1411:(ATP) is hydrolyzed to
1401:argininosuccinate lyase
1144:Guanidinopropionic acid
1086:5110 mg/kg (rat, oral)
955:β3.7396ββ3.7370 MJ mol
804:14.87 g/100 mL (20 Β°C)
6160:Glucogenic amino acids
6061:L-Type calcium channel
4808:Cysteine sulfinic acid
4654:conversion to cysteine
4411:Formiminoglutamic acid
4338:3-Phosphoglyceric acid
4215:Ξ²-Methylglutaconyl-CoA
3687:NIST Chemistry Webbook
3418:American Heart Journal
3176:10.1210/jcem-67-6-1186
1621:
1434:
1433:Arginine biosynthesis.
1409:adenosine triphosphate
1112:Related alkanoic acids
75:
61:
5665:Cindunistat (SD-6010)
5620:2-Ethylaminoguanidine
5377:Spermine/NO (SPER/NO)
5174:O-Nitroso compounds (
4540:Ξ±-Ketoisovaleric acid
4195:Ξ²-Ketoisocaproic acid
4190:Ξ±-Ketoisocaproic acid
3353:10.1093/ajhp/58.4.298
2994:Kleanthous C (2000).
1725:Supplementation with
1615:
1455:proximal tubule cells
1432:
928:β624.9ββ622.3 kJ mol
74:
60:
6051:receptor antagonists
5724:Ronopterin (VAS-203)
5423:Molsidomine (SIN-10)
5344:(diazeniumdiolates):
5324:Roussin's black salt
5037:Mannitol hexanitrate
4627:-Adenosyl methionine
4210:Ξ²-Methylcrotonyl-CoA
4200:Ξ²-Ketoisocaproyl-CoA
4156:Ξ²-Hydroxybutyryl-CoA
3381:Integrative Medicine
2138:-valeric acid].
1958:Apel F (July 2015).
1766:Raynaud's phenomenon
1692:herpes simplex virus
1346:essential amino acid
1187:Arginine (data page)
814:slightly soluble in
65:Ball-and-stick model
5418:Linsidomine (SIN-1)
5315:Nitrosyl compounds:
5282:S-Nitrosodiclofenac
5252:S-Nitrosated AR545C
5237:S-Nitroso compounds
4800:Cysteine metabolism
4589:2-Methylbutyryl-CoA
4281:2-Aminomuconic acid
4261:3-Hydroxykynurenine
3511:10.1038/tp.2016.144
3346:(4): 298β300, 304.
2776:2014NatSR...4E4548K
2363:Borlase BC (1994).
1992:"Ueber das Arginin"
1972:on 17 November 2015
1714:High blood pressure
1639:group, which has a
1543:autoimmune diseases
1315:synthesis of 1910.
1220:with the formula (H
799:Solubility in water
754: gΒ·mol
239:Beilstein Reference
79:Space-filling model
32:
5329:Roussin's red salt
5186:Cyclohexyl nitrite
5077:Nipradilol (K-351)
4687:Ξ±-Ketobutyric acid
4664:Ξ±-Ketobutyric acid
4502:Ξ³-Glutamylcysteine
4246:β²-Formylkynurenine
4131:Ξ±-Aminoadipic acid
4042:Dehydroamino acids
4002:Encoded (proteins)
3938:Negative charge (p
3897:Positive charge (p
2764:Scientific Reports
2333:Skipper A (1998).
1796:Arginine glutamate
1784:prescription drugs
1729:-arginine reduces
1622:
1551:methyltransferases
1435:
1373:protein catabolism
1252:-arginine (symbol
1202:Infobox references
1106:Related compounds
530:L: CF1934200
76:
62:
30:
6170:Basic amino acids
6165:Alpha-Amino acids
6142:
6141:
5967:
5958:
5941:
5940:
5874:
5852:
5851:
5772:
5768:
5759:
5755:
5752:N-(1-Iminoethyl)-
5718:
5714:
5705:
5701:
5698:N-(1-Iminoethyl)-
5692:
5688:
5685:N-(1-Iminoethyl)-
5625:2-Iminopiperidine
5581:
5577:
5568:
5564:
5555:
5477:
5206:Isopropyl nitrite
5152:Nitroso compounds
4994:
4979:
4978:
4820:
4819:
4816:
4815:
4787:
4786:
4761:
4760:
4748:Homogentisic acid
4714:
4713:
4706:Methylmalonyl-CoA
4510:
4509:
4371:
4370:
4294:
4293:
4051:
4050:
4012:Non-proteinogenic
3985:
3984:
3672:978-1-119-25088-3
2785:10.1038/srep04548
2516:978-1-62703-167-7
2486:978-1-4504-1487-6
2459:978-1-118-81108-5
2429:978-0-309-03496-8
2376:978-0-412-98471-6
2366:Enteral Nutrition
2346:978-0-8342-0920-6
2097:Cohen JB (1919).
1912:978-0-08-052503-7
1845:on 9 October 2008
1721:
1681:
1599:
1405:argininosuccinate
1210:Chemical compound
1208:
1207:
1164:Related compounds
1138:
1126:
1092:Safety data sheet
1039:Hazard statements
986:
590:CompTox Dashboard
535:
417:
397:L: 230-571-3
255:
249:
244:1725411, 1725412
208:Interactive image
196:Interactive image
188:Interactive image
180:Interactive image
85:
84:
16:(Redirected from
6187:
6068:dihydropyridines
5968:-arginine (NOHA)
5965:
5956:
5910:alpha aminoacids
5880:chlorogenic acid
5875:-arginine (NOHA)
5872:
5770:
5766:
5757:
5753:
5716:
5712:
5703:
5699:
5690:
5686:
5579:
5575:
5566:
5562:
5553:
5507:3-Chloroindazole
5490:
5481:
5471:
5169:
5168:
5106:Nitrofluvastatin
5090:
5089:
5032:Itramin tosilate
4988:
4901:
4847:
4840:
4833:
4824:
4796:
4726:
4640:
4639:
4527:
4388:
4320:
4305:
4256:Anthranilic acid
4136:2-Oxoadipic acid
4108:
4078:
4071:
4064:
4055:
3774:
3764:
3721:
3714:
3707:
3698:
3676:
3648:
3647:
3645:
3644:
3633:
3624:
3623:
3595:
3589:
3588:
3555:(1β2): 139β141.
3540:
3534:
3533:
3523:
3513:
3489:
3483:
3482:
3472:
3448:
3442:
3441:
3413:
3407:
3406:
3396:
3372:
3366:
3365:
3355:
3331:
3325:
3324:
3314:
3304:
3280:
3274:
3273:
3245:
3239:
3238:
3202:
3196:
3195:
3159:
3153:
3142:
3136:
3135:
3125:
3114:10.1002/pro.2647
3093:
3087:
3086:
3076:
3066:
3042:
3036:
3030:
3024:
3018:
3012:
3011:
2991:
2985:
2984:
2964:
2955:
2954:
2930:
2920:
2914:
2913:
2903:
2878:(4): 1568β1573.
2863:
2857:
2856:
2838:
2814:
2808:
2807:
2797:
2787:
2755:
2749:
2748:
2738:
2714:
2708:
2707:
2697:
2673:
2667:
2666:
2630:
2624:
2623:
2595:
2589:
2588:
2568:
2562:
2561:
2551:
2527:
2521:
2520:
2500:
2491:
2490:
2470:
2464:
2463:
2443:
2434:
2433:
2414:
2408:
2407:
2387:
2381:
2380:
2360:
2351:
2350:
2330:
2324:
2323:
2321:
2319:
2303:
2297:
2296:
2286:
2262:
2256:
2255:
2227:
2218:
2217:
2189:
2183:
2182:
2162:
2156:
2155:
2111:
2105:
2104:
2094:
2088:
2087:
2078:(3): 3191β3194.
2063:
2057:
2055:
2046:(3): 2879β2882.
2031:
2025:
2024:
2022:
2020:
2010:
2004:
2003:
1987:
1981:
1980:
1978:
1977:
1971:
1965:. Archived from
1964:
1955:
1949:
1948:
1946:
1923:
1917:
1916:
1896:
1885:
1884:
1882:
1881:
1861:
1855:
1854:
1852:
1850:
1835:
1816:of arginine and
1772:Raynaud syndrome
1728:
1719:
1679:
1619:
1597:
1594:vascular disease
1563:second messenger
1524:hydrogen bonding
1439:epithelial cells
1251:
1154:Pantothenic acid
1136:
1124:
1101:
1060:
1046:
1018:
982:
980:
951:
924:
897:
873:
858:Thermochemistry
753:
738:
732:
726:
720:
713:Chemical formula
615:
614:
598:
596:
580:
572:
564:
556:
531:
514:
506:
498:
486:
475:
458:
437:
413:
407:Gmelin Reference
390:
382:
371:
360:
339:
331:
323:
302:
294:
273:
251:
245:
229:
210:
198:
190:
182:
157:
149:
141:
133:
53:
44:Skeletal formula
40:
33:
21:
6195:
6194:
6190:
6189:
6188:
6186:
6185:
6184:
6145:
6144:
6143:
6138:
6124:
6088:PDE5 inhibitors
6050:
6014:
6001:
5937:
5914:
5848:
5782:
5733:
5601:
5527:7-Nitroindazole
5522:6-Nitroindazole
5517:5-Nitroindazole
5470:
5462:
5239:(thionitrites):
5167:
5164:
5163:
5162:
5126:Propatylnitrate
5088:
5085:
5084:
5083:
4987:
4975:
4890:
4862:
4851:
4821:
4812:
4783:
4757:
4710:
4691:
4672:
4637:
4636:
4603:
4569:
4550:Methacrylyl-CoA
4520:
4506:
4478:
4439:
4420:
4383:Ξ±-ketoglutarate
4381:
4367:
4358:Phosphocreatine
4327:
4313:
4290:
4224:
4160:
4093:
4082:
4052:
4047:
4046:
4027:Secondary amino
3981:
3944:
3933:
3903:
3892:
3858:
3825:
3765:
3756:
3730:
3725:
3683:
3673:
3660:
3657:
3652:
3651:
3642:
3640:
3635:
3634:
3627:
3597:
3596:
3592:
3542:
3541:
3537:
3491:
3490:
3486:
3450:
3449:
3445:
3415:
3414:
3410:
3374:
3373:
3369:
3333:
3332:
3328:
3282:
3281:
3277:
3262:10.1139/h11-035
3247:
3246:
3242:
3204:
3203:
3199:
3161:
3160:
3156:
3143:
3139:
3102:Protein Science
3095:
3094:
3090:
3044:
3043:
3039:
3031:
3027:
3019:
3015:
3008:
2993:
2992:
2988:
2981:
2966:
2965:
2958:
2943:
2922:
2921:
2917:
2865:
2864:
2860:
2816:
2815:
2811:
2757:
2756:
2752:
2716:
2715:
2711:
2675:
2674:
2670:
2632:
2631:
2627:
2597:
2596:
2592:
2585:
2570:
2569:
2565:
2529:
2528:
2524:
2517:
2502:
2501:
2494:
2487:
2472:
2471:
2467:
2460:
2445:
2444:
2437:
2430:
2416:
2415:
2411:
2404:
2389:
2388:
2384:
2377:
2362:
2361:
2354:
2347:
2332:
2331:
2327:
2317:
2315:
2305:
2304:
2300:
2264:
2263:
2259:
2229:
2228:
2221:
2214:
2191:
2190:
2186:
2164:
2163:
2159:
2128:-valeriansΓ€ure"
2113:
2112:
2108:
2096:
2095:
2091:
2065:
2064:
2060:
2033:
2032:
2028:
2018:
2016:
2012:
2011:
2007:
1989:
1988:
1984:
1975:
1973:
1969:
1962:
1957:
1956:
1952:
1925:
1924:
1920:
1913:
1898:
1897:
1888:
1879:
1877:
1863:
1862:
1858:
1848:
1846:
1837:
1836:
1832:
1827:
1792:
1779:
1768:
1751:
1743:weight at birth
1726:
1716:
1707:herpes labialis
1688:
1672:
1667:
1647:
1617:
1610:
1559:
1537:process called
1511:
1495:immune function
1483:
1443:small intestine
1389:
1358:small intestine
1342:
1340:Dietary sources
1326:
1321:
1289:
1249:
1247:
1239:
1235:
1231:
1227:
1223:
1211:
1204:
1199:
1176:
1165:
1158:
1113:
1097:
1083:
1077:
1055:
1041:
1027:
1011:
969:
952:
949:
943:
939:
936:
935:Std enthalpy of
925:
922:
916:
912:
909:
908:Std enthalpy of
898:
895:
888:
885:
874:
867:
849:
818:
801:
762:White crystals
751:
741:
735:
729:
723:
715:
701:
698:
689:
684:
679:
674:
669:
668:
657:
654:
653:
647:
646:
640:
639:
636:
630:
629:
618:
599:
592:
583:
538:
517:
487:
461:
440:
426:
409:
400:
363:
342:
305:
276:
241:
232:
213:
171:
160:
122:
108:
100:
81:
67:
47:
41:
28:
23:
22:
15:
12:
11:
5:
6193:
6191:
6183:
6182:
6177:
6172:
6167:
6162:
6157:
6147:
6146:
6140:
6139:
6129:
6126:
6125:
6123:
6122:
6112:
6109:
6102:
6095:
6085:
6075:
6058:
6048:
6044:
6029:ACE inhibitors
6022:
6021:
6016:
6012:
6008:
6003:
5999:
5995:
5990:
5985:
5980:
5971:
5970:
5961:
5949:
5947:
5943:
5942:
5939:
5938:
5936:
5935:
5930:
5924:
5922:
5916:
5915:
5913:
5912:
5907:
5902:
5897:
5892:
5887:
5882:
5877:
5868:
5862:
5860:
5854:
5853:
5850:
5849:
5847:
5846:
5841:
5836:
5831:
5826:
5821:
5816:
5811:
5806:
5801:
5796:
5790:
5788:
5784:
5783:
5781:
5780:
5775:
5762:
5749:
5743:
5741:
5735:
5734:
5732:
5731:
5726:
5721:
5708:
5695:
5682:
5677:
5672:
5667:
5662:
5657:
5652:
5647:
5642:
5637:
5632:
5627:
5622:
5617:
5611:
5609:
5603:
5602:
5600:
5599:
5594:
5589:
5584:
5571:
5558:
5549:
5544:
5539:
5534:
5529:
5524:
5519:
5514:
5509:
5504:
5498:
5496:
5487:
5478:
5464:
5463:
5461:
5460:
5455:
5450:
5445:
5440:
5431:
5430:
5425:
5420:
5415:
5400:
5385:
5384:
5379:
5374:
5369:
5364:
5359:
5354:
5349:
5337:
5336:
5331:
5326:
5311:
5310:
5294:
5289:
5284:
5279:
5274:
5269:
5264:
5259:
5254:
5249:
5244:
5232:-Butyl nitrite
5226:
5224:Pentyl nitrite
5221:
5219:-Butyl nitrite
5213:
5211:Methyl nitrite
5208:
5203:
5198:
5193:
5188:
5183:
5176:alkyl nitrites
5165:
5147:
5146:
5141:
5138:
5133:
5128:
5123:
5118:
5113:
5108:
5103:
5098:
5093:
5086:
5079:
5074:
5069:
5064:
5059:
5054:
5049:
5044:
5039:
5034:
5029:
5024:
5019:
5014:
5009:
4997:
4995:
4981:
4980:
4977:
4976:
4974:
4973:
4964:
4963:
4958:
4953:
4948:
4943:
4938:
4933:
4928:
4923:
4918:
4909:
4907:
4898:
4892:
4891:
4889:
4888:
4883:
4878:
4872:
4870:
4864:
4863:
4852:
4850:
4849:
4842:
4835:
4827:
4818:
4817:
4814:
4813:
4811:
4810:
4804:
4802:
4793:
4789:
4788:
4785:
4784:
4782:
4781:
4772:
4770:
4763:
4762:
4759:
4758:
4756:
4755:
4750:
4745:
4739:
4737:
4723:
4716:
4715:
4712:
4711:
4709:
4708:
4702:
4700:
4693:
4692:
4690:
4689:
4683:
4681:
4674:
4673:
4671:
4670:
4661:
4649:
4648:
4643:
4629:
4614:
4612:
4605:
4604:
4602:
4601:
4596:
4591:
4586:
4580:
4578:
4571:
4570:
4568:
4567:
4562:
4557:
4552:
4547:
4545:Isobutyryl-CoA
4542:
4536:
4534:
4524:
4512:
4511:
4508:
4507:
4505:
4504:
4486:
4484:
4480:
4479:
4477:
4476:
4471:
4466:
4461:
4456:
4450:
4448:
4441:
4440:
4438:
4437:
4431:
4429:
4422:
4421:
4419:
4418:
4413:
4408:
4403:
4397:
4395:
4385:
4373:
4372:
4369:
4368:
4366:
4365:
4360:
4355:
4341:
4340:
4334:
4332:
4317:
4302:
4296:
4295:
4292:
4291:
4289:
4288:
4283:
4278:
4273:
4268:
4263:
4258:
4253:
4248:
4239:
4237:
4226:
4225:
4223:
4222:
4217:
4212:
4207:
4202:
4197:
4192:
4187:
4185:Isovaleryl-CoA
4182:
4177:
4171:
4169:
4162:
4161:
4159:
4158:
4153:
4148:
4146:Glutaconyl-CoA
4143:
4138:
4133:
4128:
4123:
4117:
4115:
4105:
4095:
4094:
4083:
4081:
4080:
4073:
4066:
4058:
4049:
4048:
4045:
4044:
4039:
4034:
4029:
4024:
4019:
4014:
4009:
4004:
3991:
3990:
3987:
3986:
3983:
3982:
3980:
3979:
3973:
3967:
3964:Selenocysteine
3961:
3955:
3948:
3946:
3942:
3935:
3934:
3932:
3931:
3926:
3920:
3914:
3907:
3905:
3901:
3894:
3893:
3891:
3890:
3885:
3880:
3875:
3869:
3867:
3860:
3859:
3857:
3856:
3851:
3846:
3841:
3835:
3833:
3827:
3826:
3824:
3823:
3818:
3813:
3808:
3803:
3797:
3792:
3782:
3780:
3771:
3767:
3766:
3759:
3757:
3755:
3754:
3749:
3744:
3738:
3736:
3735:General topics
3732:
3731:
3726:
3724:
3723:
3716:
3709:
3701:
3695:
3694:
3689:
3682:
3681:External links
3679:
3678:
3677:
3671:
3656:
3653:
3650:
3649:
3625:
3590:
3535:
3484:
3443:
3408:
3367:
3326:
3295:(3): 609β613.
3275:
3240:
3197:
3154:
3137:
3088:
3037:
3035:, p. 176.
3025:
3023:, p. 275.
3013:
3006:
2986:
2979:
2956:
2942:978-0805330663
2941:
2915:
2858:
2809:
2770:(4548): 4548.
2750:
2709:
2668:
2625:
2590:
2583:
2563:
2522:
2515:
2492:
2485:
2465:
2458:
2435:
2428:
2409:
2402:
2382:
2375:
2352:
2345:
2325:
2298:
2257:
2238:(9): 439β445.
2219:
2213:978-3527306732
2212:
2184:
2157:
2146:(1): 643β651.
2106:
2089:
2058:
2026:
2005:
1982:
1950:
1918:
1911:
1886:
1856:
1829:
1828:
1826:
1823:
1822:
1821:
1803:
1798:
1791:
1788:
1778:
1775:
1767:
1764:
1750:
1747:
1715:
1712:
1687:
1684:
1676:growth hormone
1671:
1670:Growth hormone
1668:
1666:
1663:
1659:hydrogen bonds
1645:
1609:
1606:
1558:
1555:
1539:citrullination
1510:
1507:
1503:blood pressure
1482:
1479:
1388:
1385:
1341:
1338:
1325:
1322:
1320:
1317:
1288:
1285:
1245:
1237:
1233:
1229:
1225:
1224:N)(HN)CN(H)(CH
1221:
1209:
1206:
1205:
1200:
1196:standard state
1193:
1190:
1189:
1183:
1182:
1178:
1177:
1175:
1174:
1168:
1166:
1163:
1160:
1159:
1157:
1156:
1151:
1146:
1141:
1129:
1127:-aspartic acid
1116:
1114:
1111:
1108:
1107:
1103:
1102:
1095:
1088:
1087:
1084:
1075:
1073:
1070:
1069:
1062:
1061:
1059:P305+P351+P338
1056:
1051:
1048:
1047:
1042:
1037:
1034:
1033:
1028:
1023:
1020:
1019:
1012:
1007:
1004:
1003:
993:
992:
988:
987:
970:
965:
962:
961:
957:
956:
953:
947:
941:
933:
930:
929:
926:
920:
914:
906:
903:
902:
901:250.6 J K mol
899:
893:
882:
879:
878:
875:
863:
860:
859:
855:
854:
851:
847:
837:
836:
833:
824:
823:
812:
806:
805:
802:
797:
794:
793:
790:
784:
783:
780:
774:
773:
770:
764:
763:
760:
756:
755:
749:
743:
742:
739:
733:
727:
721:
716:
711:
708:
707:
703:
702:
700:
699:
692:
690:
687:
685:
682:
680:
677:
675:
672:
664:
663:
662:
659:
658:
656:
655:
651:
650:
648:
644:
643:
641:
637:
634:
633:
625:
624:
623:
620:
619:
617:
616:
602:
600:
588:
585:
584:
582:
581:
573:
565:
557:
548:
546:
540:
539:
537:
536:
527:
525:
519:
518:
516:
515:
507:
499:
490:
488:
480:
477:
476:
469:
463:
462:
460:
459:
450:
448:
442:
441:
439:
438:
429:
427:
422:
419:
418:
410:
405:
402:
401:
399:
398:
394:
392:
384:
383:
373:
365:
364:
362:
361:
352:
350:
344:
343:
341:
340:
332:
324:
315:
313:
307:
306:
304:
303:
295:
286:
284:
278:
277:
275:
274:
265:
263:
257:
256:
242:
237:
234:
233:
231:
230:
221:
219:
215:
214:
212:
211:
199:
191:
183:
174:
172:
165:
162:
161:
159:
158:
150:
142:
134:
125:
123:
118:
115:
114:
110:
109:
106:
102:
101:
98:
92:
91:
87:
86:
83:
82:
77:
68:
63:
49:
48:
42:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
6192:
6181:
6178:
6176:
6173:
6171:
6168:
6166:
6163:
6161:
6158:
6156:
6153:
6152:
6150:
6137:
6136:
6133:
6127:
6120:
6116:
6113:
6110:
6107:
6103:
6100:
6096:
6093:
6089:
6086:
6083:
6079:
6076:
6073:
6069:
6065:
6062:
6059:
6056:
6052:
6045:
6042:
6038:
6034:
6030:
6027:
6024:
6023:
6020:
6017:
6015:
6009:
6007:
6004:
6002:
5996:
5994:
5991:
5989:
5986:
5984:
5981:
5979:
5976:
5973:
5972:
5969:
5962:
5960:
5954:
5951:
5950:
5948:
5944:
5934:
5931:
5929:
5928:Calmidazolium
5926:
5925:
5923:
5921:
5917:
5911:
5908:
5906:
5903:
5901:
5898:
5896:
5893:
5891:
5888:
5886:
5883:
5881:
5878:
5876:
5869:
5867:
5864:
5863:
5861:
5859:
5855:
5845:
5842:
5840:
5837:
5835:
5832:
5830:
5827:
5825:
5822:
5820:
5817:
5815:
5812:
5810:
5807:
5805:
5802:
5800:
5797:
5795:
5792:
5791:
5789:
5785:
5779:
5776:
5774:
5763:
5761:
5750:
5748:
5745:
5744:
5742:
5740:
5736:
5730:
5727:
5725:
5722:
5720:
5709:
5707:
5696:
5694:
5683:
5681:
5678:
5676:
5673:
5671:
5668:
5666:
5663:
5661:
5658:
5656:
5653:
5651:
5648:
5646:
5643:
5641:
5638:
5636:
5633:
5631:
5628:
5626:
5623:
5621:
5618:
5616:
5613:
5612:
5610:
5608:
5604:
5598:
5595:
5593:
5590:
5588:
5585:
5583:
5572:
5570:
5559:
5557:
5550:
5548:
5545:
5543:
5540:
5538:
5535:
5533:
5530:
5528:
5525:
5523:
5520:
5518:
5515:
5513:
5510:
5508:
5505:
5503:
5500:
5499:
5497:
5495:
5491:
5488:
5486:
5482:
5479:
5475:
5469:
5465:
5459:
5456:
5454:
5451:
5449:
5446:
5444:
5441:
5439:
5436:
5433:
5432:
5429:
5426:
5424:
5421:
5419:
5416:
5414:
5411:
5409:
5404:
5401:
5399:
5396:
5394:
5390:
5387:
5386:
5383:
5380:
5378:
5375:
5373:
5370:
5368:
5365:
5363:
5360:
5358:
5355:
5353:
5350:
5348:
5345:
5343:
5339:
5338:
5335:
5332:
5330:
5327:
5325:
5322:
5320:
5316:
5313:
5312:
5309:
5306:
5304:
5298:
5295:
5293:
5290:
5288:
5285:
5283:
5280:
5278:
5275:
5273:
5270:
5268:
5265:
5263:
5260:
5258:
5255:
5253:
5250:
5248:
5245:
5243:
5240:
5238:
5233:
5231:
5227:
5225:
5222:
5220:
5218:
5214:
5212:
5209:
5207:
5204:
5202:
5199:
5197:
5196:Hexyl nitrite
5194:
5192:
5191:Ethyl nitrite
5189:
5187:
5184:
5182:
5179:
5177:
5171:
5159:
5157:
5153:
5149:
5148:
5145:
5142:
5139:
5137:
5134:
5132:
5129:
5127:
5124:
5122:
5119:
5117:
5114:
5112:
5109:
5107:
5104:
5102:
5099:
5097:
5094:
5092:
5080:
5078:
5075:
5073:
5070:
5068:
5065:
5063:
5060:
5058:
5055:
5053:
5050:
5048:
5045:
5043:
5040:
5038:
5035:
5033:
5030:
5028:
5025:
5023:
5020:
5018:
5015:
5013:
5010:
5008:
5005:
5003:
4999:
4998:
4996:
4992:
4986:
4982:
4972:
4969:
4966:
4965:
4962:
4959:
4957:
4954:
4952:
4949:
4947:
4944:
4942:
4939:
4937:
4934:
4932:
4929:
4927:
4924:
4922:
4919:
4917:
4914:
4911:
4910:
4908:
4906:
4902:
4899:
4897:
4893:
4887:
4884:
4882:
4879:
4877:
4874:
4873:
4871:
4869:
4865:
4861:
4858:
4855:
4848:
4843:
4841:
4836:
4834:
4829:
4828:
4825:
4809:
4806:
4805:
4803:
4801:
4797:
4794:
4790:
4780:
4779:
4774:
4773:
4771:
4769:
4764:
4754:
4751:
4749:
4746:
4744:
4741:
4740:
4738:
4735:
4731:
4730:phenylalanine
4727:
4724:
4722:
4717:
4707:
4704:
4703:
4701:
4698:
4697:propionyl-CoA
4694:
4688:
4685:
4684:
4682:
4679:
4675:
4669:
4665:
4662:
4660:
4659:Cystathionine
4657:
4655:
4651:
4650:
4647:
4644:
4642:
4641:-homocysteine
4634:
4630:
4628:
4626:
4622:
4620:
4616:
4615:
4613:
4610:
4606:
4600:
4597:
4595:
4592:
4590:
4587:
4585:
4582:
4581:
4579:
4576:
4572:
4566:
4563:
4561:
4558:
4556:
4553:
4551:
4548:
4546:
4543:
4541:
4538:
4537:
4535:
4532:
4528:
4525:
4523:
4518:
4517:propionyl-CoA
4513:
4503:
4499:
4495:
4491:
4488:
4487:
4485:
4481:
4475:
4472:
4470:
4467:
4465:
4462:
4460:
4457:
4455:
4452:
4451:
4449:
4446:
4442:
4436:
4433:
4432:
4430:
4427:
4423:
4417:
4414:
4412:
4409:
4407:
4404:
4402:
4401:Urocanic acid
4399:
4398:
4396:
4393:
4389:
4386:
4384:
4379:
4374:
4364:
4361:
4359:
4356:
4354:
4350:
4346:
4343:
4342:
4339:
4336:
4335:
4333:
4330:
4325:
4321:
4318:
4316:
4311:
4306:
4303:
4301:
4297:
4287:
4284:
4282:
4279:
4277:
4274:
4272:
4269:
4267:
4264:
4262:
4259:
4257:
4254:
4252:
4249:
4247:
4245:
4241:
4240:
4238:
4235:
4231:
4227:
4221:
4218:
4216:
4213:
4211:
4208:
4206:
4203:
4201:
4198:
4196:
4193:
4191:
4188:
4186:
4183:
4181:
4178:
4176:
4173:
4172:
4170:
4167:
4163:
4157:
4154:
4152:
4149:
4147:
4144:
4142:
4139:
4137:
4134:
4132:
4129:
4127:
4124:
4122:
4119:
4118:
4116:
4113:
4109:
4106:
4104:
4100:
4096:
4092:
4089:
4086:
4079:
4074:
4072:
4067:
4065:
4060:
4059:
4056:
4043:
4040:
4038:
4037:D-amino acids
4035:
4033:
4030:
4028:
4025:
4023:
4020:
4018:
4015:
4013:
4010:
4008:
4005:
4003:
3999:
3997:
3993:
3992:
3988:
3977:
3974:
3971:
3968:
3965:
3962:
3959:
3958:Glutamic acid
3956:
3953:
3952:Aspartic acid
3950:
3949:
3947:
3941:
3936:
3930:
3927:
3924:
3921:
3918:
3915:
3912:
3909:
3908:
3906:
3900:
3895:
3889:
3886:
3884:
3881:
3879:
3876:
3874:
3871:
3870:
3868:
3865:
3861:
3855:
3854:Phenylalanine
3852:
3850:
3847:
3845:
3842:
3840:
3837:
3836:
3834:
3832:
3828:
3822:
3819:
3817:
3814:
3812:
3809:
3807:
3804:
3801:
3798:
3796:
3793:
3791:
3787:
3784:
3783:
3781:
3779:
3775:
3772:
3770:By properties
3768:
3763:
3753:
3750:
3748:
3745:
3743:
3740:
3739:
3737:
3733:
3729:
3722:
3717:
3715:
3710:
3708:
3703:
3702:
3699:
3693:
3690:
3688:
3685:
3684:
3680:
3674:
3668:
3664:
3659:
3658:
3654:
3638:
3632:
3630:
3626:
3621:
3617:
3613:
3609:
3606:(3): 376β99.
3605:
3601:
3594:
3591:
3586:
3582:
3578:
3574:
3570:
3566:
3562:
3558:
3554:
3550:
3546:
3539:
3536:
3531:
3527:
3522:
3517:
3512:
3507:
3503:
3499:
3495:
3488:
3485:
3480:
3476:
3471:
3466:
3462:
3458:
3454:
3447:
3444:
3439:
3435:
3431:
3427:
3424:(6): 959β65.
3423:
3419:
3412:
3409:
3404:
3400:
3395:
3390:
3386:
3382:
3378:
3371:
3368:
3363:
3359:
3354:
3349:
3345:
3341:
3337:
3330:
3327:
3322:
3318:
3313:
3308:
3303:
3298:
3294:
3290:
3286:
3279:
3276:
3271:
3267:
3263:
3259:
3256:(3): 405β11.
3255:
3251:
3244:
3241:
3236:
3232:
3228:
3224:
3220:
3216:
3212:
3208:
3201:
3198:
3193:
3189:
3185:
3181:
3177:
3173:
3170:(6): 1186β9.
3169:
3165:
3158:
3155:
3152:
3148:
3147:
3141:
3138:
3133:
3129:
3124:
3119:
3115:
3111:
3108:(5): 752β61.
3107:
3103:
3099:
3092:
3089:
3084:
3080:
3075:
3070:
3065:
3060:
3056:
3052:
3048:
3041:
3038:
3034:
3029:
3026:
3022:
3017:
3014:
3009:
3007:9780199637607
3003:
2999:
2998:
2990:
2987:
2982:
2980:9780470026199
2976:
2972:
2971:
2963:
2961:
2957:
2952:
2948:
2944:
2938:
2934:
2929:
2928:
2919:
2916:
2911:
2907:
2902:
2897:
2893:
2889:
2885:
2881:
2877:
2873:
2869:
2862:
2859:
2854:
2850:
2846:
2842:
2837:
2832:
2828:
2824:
2820:
2813:
2810:
2805:
2801:
2796:
2791:
2786:
2781:
2777:
2773:
2769:
2765:
2761:
2754:
2751:
2746:
2742:
2737:
2732:
2728:
2724:
2720:
2713:
2710:
2705:
2701:
2696:
2691:
2688:(3): 521β31.
2687:
2683:
2679:
2672:
2669:
2664:
2660:
2656:
2652:
2648:
2644:
2641:(6): 419β23.
2640:
2636:
2629:
2626:
2621:
2617:
2613:
2609:
2605:
2601:
2594:
2591:
2586:
2584:9782889196227
2580:
2576:
2575:
2567:
2564:
2559:
2555:
2550:
2545:
2541:
2537:
2533:
2526:
2523:
2518:
2512:
2508:
2507:
2499:
2497:
2493:
2488:
2482:
2478:
2477:
2469:
2466:
2461:
2455:
2451:
2450:
2442:
2440:
2436:
2431:
2425:
2421:
2420:
2413:
2410:
2405:
2403:9789400957329
2399:
2395:
2394:
2386:
2383:
2378:
2372:
2368:
2367:
2359:
2357:
2353:
2348:
2342:
2338:
2337:
2329:
2326:
2314:
2313:
2308:
2302:
2299:
2294:
2290:
2285:
2280:
2277:(8): 442β51.
2276:
2272:
2268:
2261:
2258:
2253:
2249:
2245:
2241:
2237:
2233:
2226:
2224:
2220:
2215:
2209:
2205:
2201:
2197:
2196:
2188:
2185:
2180:
2176:
2172:
2168:
2161:
2158:
2153:
2149:
2145:
2142:(in German).
2141:
2137:
2133:
2129:
2127:
2123:
2119:
2110:
2107:
2102:
2101:
2093:
2090:
2085:
2081:
2077:
2074:(in German).
2073:
2069:
2062:
2059:
2053:
2049:
2045:
2042:(in German).
2041:
2037:
2030:
2027:
2015:
2009:
2006:
2002:(1β2): 43β65.
2001:
1997:
1993:
1986:
1983:
1968:
1961:
1954:
1951:
1945:
1940:
1936:
1932:
1928:
1922:
1919:
1914:
1908:
1904:
1903:
1895:
1893:
1891:
1887:
1875:
1871:
1867:
1860:
1857:
1844:
1840:
1834:
1831:
1824:
1819:
1815:
1811:
1807:
1804:
1802:
1799:
1797:
1794:
1793:
1789:
1787:
1785:
1776:
1774:
1773:
1763:
1760:
1756:
1755:schizophrenia
1749:Schizophrenia
1748:
1746:
1744:
1740:
1739:pre-eclampsia
1736:
1732:
1723:
1713:
1711:
1708:
1703:
1701:
1697:
1693:
1685:
1683:
1677:
1669:
1664:
1662:
1660:
1656:
1652:
1648:
1644:
1638:
1634:
1630:
1627:
1614:
1607:
1605:
1603:
1595:
1591:
1587:
1583:
1579:
1575:
1571:
1566:
1564:
1556:
1554:
1552:
1548:
1544:
1540:
1536:
1531:
1529:
1528:salt bridges.
1525:
1520:
1516:
1508:
1506:
1504:
1500:
1496:
1492:
1491:wound healing
1488:
1487:cell division
1480:
1478:
1476:
1472:
1468:
1462:
1460:
1456:
1452:
1448:
1444:
1440:
1431:
1427:
1425:
1421:
1416:
1414:
1410:
1406:
1402:
1398:
1394:
1386:
1384:
1381:
1378:
1374:
1370:
1365:
1363:
1359:
1355:
1351:
1347:
1339:
1337:
1335:
1331:
1323:
1318:
1316:
1314:
1310:
1306:
1302:
1298:
1297:Ernst Schulze
1294:
1286:
1284:
1281:
1279:
1275:
1271:
1267:
1263:
1259:
1255:
1243:
1219:
1215:
1203:
1197:
1191:
1188:
1184:
1179:
1173:
1170:
1169:
1167:
1162:
1161:
1155:
1152:
1150:
1147:
1145:
1142:
1140:
1135:-Methylamino-
1134:
1130:
1128:
1122:
1118:
1117:
1115:
1110:
1109:
1104:
1100:
1096:
1093:
1090:
1089:
1085:
1081:
1072:
1071:
1067:
1063:
1057:
1054:
1050:
1049:
1043:
1040:
1036:
1035:
1032:
1029:
1026:
1022:
1021:
1017:
1013:
1010:
1006:
1005:
1001:
999:
994:
989:
985:
979:
974:
971:
968:
964:
963:
960:Pharmacology
958:
954:
946:
938:
932:
931:
927:
919:
911:
905:
904:
900:
892:
887:
881:
880:
876:
871:
866:
865:Heat capacity
862:
861:
856:
852:
846:
842:
839:
838:
834:
832:
831:
826:
825:
822:
819:insoluble in
817:
813:
811:
808:
807:
803:
800:
796:
795:
791:
789:
788:Boiling point
786:
785:
781:
779:
778:Melting point
776:
775:
771:
769:
766:
765:
761:
758:
757:
750:
748:
745:
744:
717:
714:
710:
709:
704:
696:
691:
686:
681:
676:
671:
667:
660:
649:
642:
632:
628:
621:
613:
609:
608:DTXSID6041056
604:
603:
601:
591:
587:
586:
579:
574:
571:
566:
563:
558:
555:
550:
549:
547:
545:
542:
541:
534:
529:
528:
526:
524:
521:
520:
513:
508:
505:
500:
497:
492:
491:
489:
483:
479:
478:
474:
470:
468:
465:
464:
457:
452:
451:
449:
447:
444:
443:
436:
431:
430:
428:
425:
421:
420:
416:
411:
408:
404:
403:
396:
395:
393:
391:
386:
385:
381:
377:
374:
372:
370:ECHA InfoCard
367:
366:
359:
354:
353:
351:
349:
346:
345:
338:
333:
330:
325:
322:
317:
316:
314:
312:
309:
308:
301:
296:
293:
288:
287:
285:
283:
280:
279:
272:
267:
266:
264:
262:
259:
258:
254:
248:
243:
240:
236:
235:
228:
223:
222:
220:
217:
216:
209:
204:
200:
197:
192:
189:
184:
181:
176:
175:
173:
169:
164:
163:
156:
151:
148:
143:
140:
135:
132:
127:
126:
124:
121:
117:
116:
111:
103:
97:
93:
88:
80:
73:
69:
66:
59:
55:
54:
50:
45:
39:
34:
19:
6131:
6130:
6106:paraxanthine
6082:beta blocker
6025:
5974:
5955:
5952:
5756:-ornithine (
5689:-ornithine (
5434:
5413:Feprosidnine
5408:Sydnonimines
5406:
5391:
5388:
5340:
5317:
5314:
5303:nitrosamines
5300:
5235:
5229:
5216:
5173:
5150:
5000:
4967:
4946:GSK-2181236A
4912:
4854:Nitric oxide
4775:
4768:oxaloacetate
4652:
4646:Homocysteine
4632:
4624:
4617:
4522:succinyl-CoA
4444:
4353:Glycocyamine
4286:Glutaryl-CoA
4243:
4151:Crotonyl-CoA
4141:Glutaryl-CoA
4121:Saccharopine
3994:
3939:
3916:
3898:
3752:Genetic code
3662:
3641:. Retrieved
3637:"L-Arginine"
3603:
3599:
3593:
3552:
3548:
3538:
3501:
3497:
3487:
3463:(1): 88β96.
3460:
3456:
3455:. (review).
3446:
3421:
3417:
3411:
3387:(3): 42β46.
3384:
3380:
3370:
3343:
3339:
3329:
3292:
3288:
3278:
3253:
3249:
3243:
3210:
3206:
3200:
3167:
3163:
3157:
3144:
3140:
3105:
3101:
3091:
3054:
3051:Biomedicines
3050:
3040:
3028:
3016:
2996:
2989:
2969:
2927:Biochemistry
2926:
2918:
2875:
2871:
2861:
2826:
2822:
2812:
2767:
2763:
2753:
2726:
2722:
2712:
2685:
2681:
2680:. (review).
2671:
2638:
2634:
2628:
2606:(1): 52β61.
2603:
2599:
2593:
2573:
2566:
2539:
2535:
2534:. (review).
2525:
2505:
2475:
2468:
2448:
2418:
2412:
2392:
2385:
2365:
2335:
2328:
2316:. Retrieved
2310:
2301:
2274:
2270:
2269:. (review).
2260:
2235:
2231:
2193:
2187:
2170:
2166:
2160:
2143:
2139:
2135:
2131:
2125:
2121:
2117:
2109:
2099:
2092:
2075:
2071:
2061:
2043:
2039:
2029:
2017:. Retrieved
2008:
1999:
1995:
1985:
1974:. Retrieved
1967:the original
1953:
1934:
1930:
1921:
1901:
1878:. Retrieved
1869:
1859:
1847:. Retrieved
1843:the original
1833:
1780:
1769:
1752:
1724:
1717:
1704:
1689:
1673:
1642:
1623:
1567:
1560:
1532:
1512:
1499:nitric oxide
1484:
1463:
1436:
1417:
1390:
1387:Biosynthesis
1382:
1366:
1343:
1327:
1300:
1293:yellow lupin
1290:
1282:
1278:nitric oxide
1257:
1253:
1213:
1212:
1132:
1120:
1065:
1030:
997:
983:
944:
917:
890:
869:
844:
829:
575:L HCl:
532:
523:RTECS number
414:
300:ChEMBL212301
252:
246:
193:L HCl:
152:L HCl:
113:Identifiers
105:Other names
6119:simvastatin
5953:Precursors:
5890:epicatechin
5814:Indospicine
5769:-arginine (
5715:-arginine (
5650:AR-C 102222
5578:-arginine (
5565:-arginine (
5428:Sydnonimine
5161:Nitrite (NO
5144:Trolnitrate
5140:Tenitramine
5082:Nitrate (NO
4968:Inhibitors:
4951:Praliciguat
4931:BAY 60-4552
4926:BAY 41-8543
4921:BAY 41-2272
4498:glutathione
4032:Imino acids
3996:Amino acids
3929:Pyrrolysine
3866:, uncharged
3504:(8): e871.
3213:(1): 50β4.
2312:Mayo Clinic
1651:conjugation
1637:guanidinium
1602:endothelium
1549:by protein
1547:methylation
1515:amphipathic
1080:median dose
1066:Lethal dose
1025:Signal word
821:ethyl ether
759:Appearance
706:Properties
376:100.000.738
271:CHEBI:29016
96:IUPAC names
46:of arginine
6180:Urea cycle
6175:Guanidines
6149:Categories
6092:sildenafil
6072:nifedipine
5975:Cofactors:
5964:N-Hydroxy-
5871:N-Hydroxy-
5660:Canavanine
5655:BYK-191023
5474:inhibitors
5403:REC15/2739
5382:V-PYRRO/NO
5072:Nicorandil
4961:Vericiguat
4860:modulators
4778:urea cycle
4635:-Adenosyl-
4609:methionine
4594:Tiglyl-CoA
4575:isoleucine
4474:Putrescine
4469:Cadaverine
4464:Citrulline
4363:Creatinine
4251:Kynurenine
4230:tryptophan
4103:acetyl-CoA
4088:metabolism
4085:Amino acid
4022:Glucogenic
3873:Asparagine
3849:Tryptophan
3806:Methionine
3795:Isoleucine
3643:2021-05-27
3057:(8): 277.
2829:: 100042.
2318:15 January
2167:Org. Synth
1976:2017-11-06
1880:2007-05-17
1825:References
1812:are toxic
1806:Canavanine
1655:lone pairs
1629:side-chain
1626:amino acid
1596:, just as
1586:polyamines
1393:citrulline
1369:urea cycle
1354:citrulline
1330:hydrolysis
1324:Production
1313:SΓΈrensen's
1218:amino acid
1099:L-Arginine
1009:Pictograms
937:combustion
810:Solubility
772:Odourless
747:Molar mass
695:Zwitterion
578:F7LTH1E20Y
570:R54Z304Z7C
562:FL26NTK3EP
559:D/L:
554:94ZLA3W45F
501:D/L:
424:IUPHAR/BPS
326:D/L:
311:ChemSpider
292:ChEMBL1485
250:, 1725413
203:Zwitterion
166:3D model (
136:D/L:
120:CAS Number
27:Amino acid
18:L-Arginine
6132:See also:
6078:Nebivolol
6037:captopril
5959:-Arginine
5900:norvaline
5895:ornithine
5809:GW-273629
5765:N-Methyl-
5711:N-Methyl-
5702:-lysine (
5574:N-Propyl-
5561:N-Methyl-
5542:ARL-17477
5435:Unsorted:
4985:NO donors
4956:Riociguat
4936:BI-703704
4916:Ataciguat
4857:signaling
4678:threonine
4494:glutamate
4459:Ornithine
4392:histidine
4378:glutamate
4205:Ξ²-Leucine
4017:Ketogenic
4007:Essential
3923:Histidine
3888:Threonine
3878:Glutamine
3839:Histidine
3778:Aliphatic
3569:0300-8177
2892:0006-4971
2853:248485831
2845:2667-3940
1818:ornithine
1696:histidine
1633:aliphatic
1620:-Arginine
1608:Structure
1574:ornithine
1557:Precursor
1519:aliphatic
1451:glutamate
1447:glutamine
1420:glutamine
1350:glutamine
1309:cyanamide
1305:ornithine
1274:precursor
1242:guanidino
1172:Panthenol
1000:labelling
910:formation
884:Std molar
389:EC Number
155:1119-34-2
139:7200-25-1
31:Arginine
6099:caffeine
6064:blockers
6055:bosentan
6041:losartan
5858:Arginase
5844:VAS-2381
5839:ONO-1714
5787:Unsorted
5547:Indazole
5453:FR146881
5448:FR144220
5438:Cimlanod
5393:Furoxans
5372:PROLI/NO
5342:NONOates
5292:SNO-t-PA
5156:nitrites
5067:NCX-4215
5062:NCX 4040
5057:NCX-4016
5052:NCX-2216
5002:Nitrates
4991:prodrugs
4734:tyrosine
4721:fumarate
4668:Cysteine
4490:cysteine
4454:Agmatine
4445:arginine
4349:creatine
4310:pyruvate
4126:Allysine
3976:Tyrosine
3970:Cysteine
3917:Arginine
3844:Tyrosine
3831:Aromatic
3620:18325648
3585:30249281
3577:12701823
3530:27529679
3479:23435582
3438:22137067
3403:30881246
3362:11225166
3321:14127578
3270:21574873
3235:22842434
3227:18090659
3132:25808204
3083:32781796
2951:42290721
2910:17023580
2804:24686447
2745:15465790
2704:10690324
2663:21239136
2655:14617280
2620:16207646
2558:15465778
2293:15302078
2252:12481980
1874:Archived
1810:canaline
1790:See also
1759:agmatine
1665:Research
1582:creatine
1578:agmatine
1509:Proteins
1481:Function
1264:. It is
1262:proteins
1214:Arginine
1149:Theanine
1139:-alanine
1123:-Methyl-
991:Hazards
967:ATC code
605:L:
567:D:
551:L:
509:D:
493:L:
473:Arginine
453:L:
432:L:
355:L:
348:DrugBank
334:D:
318:L:
297:D:
289:L:
268:L:
224:L:
185:D:
177:L:
147:157-06-2
144:D:
128:L:
99:Arginine
6117:(e.g.,
6115:Statins
6090:(e.g.,
6066:(e.g.,
6053:(e.g.,
6035:(e.g.,
5885:ginseng
5834:NXN-462
5829:NCX-456
5819:KD-7040
5799:CKD-712
5532:A-84643
5398:Furoxan
5297:SNO-vWF
5047:NCX-466
4896:Targets
4426:proline
4345:glycine
4324:glycine
4315:citrate
4234:alanine
4166:leucine
3978:(β10.1)
3919:(β12.5)
3913:(β10.8)
3821:Glycine
3816:Proline
3811:Alanine
3800:Leucine
3747:Peptide
3742:Protein
3655:Sources
3521:5022089
3394:6419779
3192:7488757
3184:2903866
3123:4420524
3074:7460461
2901:1794048
2795:4070089
2772:Bibcode
2019:25 July
1849:5 March
1814:analogs
1475:nitrite
1471:nitrate
1457:of the
1441:of the
1424:proline
1377:ammonia
1362:kidneys
1334:gelatin
1319:Sources
1301:Γ‘rgyros
1287:History
1268:by the
1266:encoded
1216:is the
1031:Warning
975: (
973:B05XB01
886:entropy
841:Acidity
835:β1.652
816:ethanol
752:174.204
482:PubChem
412:364938
358:DB00125
205::
131:74-79-3
5946:Others
5905:lysine
5468:Enzyme
5443:FK-409
5357:GLO/NO
5308:SIN-1A
4531:valine
4329:serine
4112:lysine
3972:(β8.3)
3966:(β5.4)
3960:(β4.1)
3954:(β3.9)
3925:(β6.1)
3911:Lysine
3883:Serine
3790:Valine
3669:
3618:
3583:
3575:
3567:
3528:
3518:
3477:
3436:
3401:
3391:
3360:
3319:
3312:277062
3309:
3268:
3233:
3225:
3190:
3182:
3130:
3120:
3081:
3071:
3004:
2977:
2949:
2939:
2908:
2898:
2890:
2851:
2843:
2802:
2792:
2743:
2702:
2661:
2653:
2618:
2581:
2556:
2513:
2483:
2456:
2426:
2400:
2373:
2343:
2291:
2250:
2210:
1909:
1700:lysine
1576:, and
1459:kidney
1422:, and
1270:codons
1094:(SDS)
666:SMILES
456:C02385
282:ChEMBL
227:B01331
218:3DMet
90:Names
5978:NADPH
5773:-NMA)
5760:-NIO)
5719:-NMA)
5706:-NIL)
5693:-NIO)
5635:AEITU
5630:1400W
5582:-NPA)
5569:-NMA)
5556:-NIO)
5242:LA810
4868:Forms
4792:Other
4483:other
3998:types
3864:Polar
3581:S2CID
3231:S2CID
3188:S2CID
2872:Blood
2849:S2CID
2659:S2CID
2173:: 4.
1970:(PDF)
1963:(PDF)
1232:CH(NH
627:InChI
512:71070
337:64224
261:ChEBI
168:JSmol
5993:Heme
5920:CAMK
5739:eNOS
5729:TRIM
5680:MITU
5675:IPTU
5670:EITU
5607:iNOS
5597:TRIM
5494:nNOS
5362:JS-K
5230:tert
4776:see
3667:ISBN
3616:PMID
3573:PMID
3565:ISSN
3526:PMID
3475:PMID
3434:PMID
3399:PMID
3358:PMID
3317:PMID
3266:PMID
3223:PMID
3180:PMID
3128:PMID
3079:PMID
3002:ISBN
2975:ISBN
2947:OCLC
2937:ISBN
2906:PMID
2888:ISSN
2841:ISSN
2800:PMID
2741:PMID
2700:PMID
2651:PMID
2616:PMID
2579:ISBN
2554:PMID
2511:ISBN
2481:ISBN
2454:ISBN
2424:ISBN
2398:ISBN
2371:ISBN
2341:ISBN
2320:2015
2289:PMID
2248:PMID
2208:ISBN
2021:2019
1907:ISBN
1851:2018
1808:and
1801:AAKG
1624:The
1570:urea
1526:and
1473:and
1449:and
1399:and
1360:and
1352:via
1307:and
1133:beta
1045:H319
828:log
768:Odor
544:UNII
496:6322
467:MeSH
446:KEGG
321:6082
6006:CaM
5988:FMN
5983:FAD
5933:W-7
5866:ABH
5645:AMT
5485:NOS
4971:ODQ
4905:sGC
3608:doi
3557:doi
3553:244
3516:PMC
3506:doi
3465:doi
3426:doi
3422:162
3389:PMC
3348:doi
3307:PMC
3297:doi
3258:doi
3215:doi
3172:doi
3118:PMC
3110:doi
3069:PMC
3059:doi
2933:180
2896:PMC
2880:doi
2876:109
2831:doi
2790:PMC
2780:doi
2731:doi
2727:134
2690:doi
2643:doi
2608:doi
2544:doi
2540:134
2279:doi
2240:doi
2200:doi
2175:doi
2148:doi
2080:doi
2048:doi
1939:doi
1935:243
1256:or
1254:Arg
1236:)CO
998:GHS
978:WHO
948:298
921:298
894:298
595:EPA
504:232
485:CID
435:721
329:227
6151::
6070::
6047:ET
6039:,
6019:Ca
5998:BH
5405:;
5305:):
5299:;
5234:;
5178:):
5172:;
4766:Gβ
4719:Gβ
4666:+
4515:Gβ
4500::
4376:Gβ
4351::
4312:β
4308:Gβ
4000::
3628:^
3614:.
3604:50
3602:.
3579:.
3571:.
3563:.
3551:.
3547:.
3524:.
3514:.
3500:.
3496:.
3473:.
3461:15
3459:.
3432:.
3420:.
3397:.
3385:16
3383:.
3379:.
3356:.
3344:58
3342:.
3338:.
3315:.
3305:.
3293:87
3291:.
3287:.
3264:.
3254:36
3252:.
3229:.
3221:.
3211:11
3209:.
3186:.
3178:.
3168:67
3166:.
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3116:.
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2273:.
2246:.
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2206:.
2171:12
2169:.
2144:43
2118:dl
2076:32
2044:30
2000:11
1998:.
1933:.
1929:.
1889:^
1872:.
1868:.
1745:.
1661:.
1604:.
1572:,
1553:.
1489:,
1076:50
1074:LD
1002::
981:)
940:(Ξ
913:(Ξ
850:)
843:(p
728:14
693:L
201:L
6121:)
6108:)
6101:)
6094:)
6084:)
6080:(
6074:)
6057:)
6049:B
6043:)
6031:/
6013:2
6011:O
6000:4
5966:L
5957:L
5873:L
5771:L
5767:L
5758:L
5754:L
5717:L
5713:L
5704:L
5700:L
5691:L
5687:L
5580:L
5576:L
5567:L
5563:L
5554:L
5476:)
5472:(
5410::
5395::
5321::
5217:n
5170:)
5166:2
5158::
5154:/
5091:)
5087:3
5004::
4993:)
4989:(
4846:e
4839:t
4832:v
4736:β
4732:β
4699:β
4680:β
4656::
4638:L
4633:S
4625:S
4621::
4611:β
4577:β
4533:β
4519:β
4496:β
4492:+
4447:β
4428:β
4394:β
4380:β
4347:β
4331:β
4326:β
4300:G
4244:N
4236:β
4232:β
4168:β
4114:β
4101:β
4099:K
4077:e
4070:t
4063:v
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1947:.
1941::
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1820:.
1727:l
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1226:2
1222:2
1137:L
1125:D
1121:N
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950:)
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915:f
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891:S
889:(
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870:C
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725:H
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533:L
415:D
253:L
247:D
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