(2S)-2-{[(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-13-benzyl-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamido-N-(carbamoylmethyl)pentanamide

• ChemBase ID: 160733
• Molecular Formular: C46H65N15O12S2
• Molecular Mass: 1084.2316
• Monoisotopic Mass: 1083.4378546
• SMILES: [C@H]1(C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N1)Cc1ccc(cc1)O)N)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)NCC(=O)N)CCCNC(=N)N)CC(=O)N)CCC(=O)N)Cc1ccccc1
• Canonical SMILES: NC(=O)C[C@@H]1NC(=O)[C@H](CCC(=O)N)NC(=O)[C@@H](Cc2ccccc2)NC(=O)[C@H](Cc2ccc(cc2)O)NC(=O)[C@H](CSSC[C@H](NC1=O)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)NCC(=O)N)CCCNC(=N)N)N
• InChI: InChI=1S/C46H65N15O12S2/c47-27-22-74-75-23-33(45(73)61-17-5-9-34(61)44(72)56-28(8-4-16-53-46(51)52)39(67)54-21-37(50)65)60-43(71)32(20-36(49)64)59-40(68)29(14-15-35(48)63)55-41(69)31(18-24-6-2-1-3-7-24)58-42(70)30(57-38(27)66)19-25-10-12-26(62)13-11-25/h1-3,6-7,10-13,27-34,62H,4-5,8-9,14-23,47H2,(H2,48,63)(H2,49,64)(H2,50,65)(H,54,67)(H,55,69)(H,56,72)(H,57,66)(H,58,70)(H,59,68)(H,60,71)(H4,51,52,53)/t27-,28-,29-,30-,31-,32-,33-,34-/m0/s1
• InChIKey: KBZOIRJILGZLEJ-LGYYRGKSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-13-benzyl-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamido-N-(carbamoylmethyl)pentanamide
• IUPAC Traditional name: (2S)-2-{[(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-13-benzyl-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamido-N-(carbamoylmethyl)pentanamide
• Synonyms: 19-Amino-13-benzyl-7-(carbamoylmethyl)-4-[2-[[1-[(carbamoylmethyl)carbamoyl]-4-guanidinobutyl]carbamoyl]-1-pyrrolidinylcarbonyl]-16-p-hydroxybenzyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloeicosane-10-propionamide Diacetate; 3-(Phenylalanine)-8-arginineoxytocin; 8-L-Arginine-vasopressin Diacetate; AVP Diacetate; Arg8-vasopressin Diacetate; Arginine antidiuretic hormone Diacetate; Arginine-8-vasopressin Diacetate; Arginine-vasopressin Diacetate; Argipressin Diacetate; Leiormone Diacetate; [8-Arginine]vasopressin Diacetate; 3-(L-Phenylalanine)-8-L-arginine-oxytocin Diacetate; Pitressin Diacetate; Rindervasopressin Diacetate; L-Cysteinyl-L-tyrosyl-L-phenylalanyl-L-glutaminyl-L-asparaginyl-L-cysteinyl-L-prolyl-L-arginylglycinamide Cyclic (1→6)-Disulfide Diacetate; Arginine Vasopressin Diacetate

Database IDs

• CAS Number: 113-79-1
• PubChem SID: 162254868
• PubChem CID: 644077

CALCULATED PROPERTIES

• Acid pKa: 9.503666
• H Acceptors: 16
• H Donor: 15
• LogD (pH = 5.5): -11.218191
• LogD (pH = 7.4): -9.281981
• Log P: -7.180408
• Molar Refractivity: 282.886 cm^3
• Polarizability: 106.02851 Å^3
• Polar Surface Area: 461.43 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A769550

An endogenous antidiuretic hormone in most mammalian species. It is released into the blood from nerve terminals in the posterior pituitary and median eminence. It is a neurotransmitter in the central nervous system and also implicated in a variety of phy

REFERENCES

• Perucca, J. et al.: J. AM. Soc. Nephrol., 19, 1721 (2008)
• Toba, K. et al.: Prog. Brain Res., 119, 337 (2008)
• Berrada, K. et al.: J. Biol. Chem., 275, 27229 (2008)