2-({1-[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: 103819
• Molecular Formular: C46H65N15O12S2
• Molecular Mass: 1084.2316
• Monoisotopic Mass: 1083.4378546
• SMILES: NC1CSSCC(NC(=O)C(CC(=O)N)NC(=O)C(CCC(=O)N)NC(=O)C(Cc2ccccc2)NC(=O)C(Cc2ccc(O)cc2)NC1=O)C(=O)N1CCCC1C(=O)NC(CCCNC(=N)N)C(=O)NCC(=O)N
• Canonical SMILES: NC(=O)CC1NC(=O)C(CCC(=O)N)NC(=O)C(Cc2ccccc2)NC(=O)C(Cc2ccc(cc2)O)NC(=O)C(CSSCC(NC1=O)C(=O)N1CCCC1C(=O)NC(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)
• InChIKey: KBZOIRJILGZLEJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({1-[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: 2-({1-[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; vasopressin
• Synonyms: AVP; Arginine Vasopressin; Antidiuretic Hormone; β-Hypophamine; Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Arg-Gly-NH₂; [Arg^8]-VASOPRESSIN; β-Hypophamine; [Arg8]-Vasopressin solution

Database IDs

• CAS Number: 113-79-1
• EC Number: 204-035-4
• MDL Number: MFCD00076738
• PubChem SID: 24900692; 162103134
• PubChem CID: 8230

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

PROPERTIES

Physical Property

• pH: ~3.5

Safety Information

• Storage Condition: -20°C
• European Hazard Symbols: Harmful (Xn)
• Risk Statements: 20
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... AVP(551)

Product Information

• Concentration: ~100 I.U./mL in 0.9% NaCl
• Contains: 0.4% 4-chlorobutanol as preservative
• Type: Grade VI (synthetic)

DETAILS

MP Biomedicals - 02152962

Contains disulfide bond between Cys1 and Cys6.

Sigma Aldrich - V0377

Amino Acid Sequence
Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Arg-Gly-NH2 [Disulfide Bridge: 1-6]
Biochem/physiol Actions
Endogenous antidiuretic hormone in most mammalian species. It is released into the blood from nerve terminals in the posterior pituitary and median eminence. Arg8-vasopressin is also a neurotransmitter in the central nervous system. It is implicated in a variety of physiological processes including diuresis, vasoregulation, and memory. Regulates water balance by antidiuretic action; contracts arterioles (vasopressor action).