(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; acetic acid

• ChemBase ID: 133268
• Molecular Formular: C48H69N15O14S2
• Molecular Mass: 1144.28356
• Monoisotopic Mass: 1143.45898396
• SMILES: CC(=O)O.c1ccc(cc1)C[C@H]1C(=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](CCCNC(=N)N)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N
• 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.CC(=O)O
• InChI: InChI=1S/C46H65N15O12S2.C2H4O2/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;1-2(3)4/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);1H3,(H,3,4)/t27-,28-,29-,30-,31-,32-,33-,34-;/m0./s1
• InChIKey: ZHFGXNMADRRGQP-HPILINOVSA-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; acetic acid
• 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; acetic acid
• Synonyms: β-Hypophamine; AVP; Antidiuretic hormone; Arginine vasopressin; [Arg8]-Vasopressin acetate salt; Argipressin acetate; [8-Arginine]Vasopressin acetate; [Arg8]Vasopressin acetate

Database IDs

• CAS Number: 113-79-1; 129979-57-3
• EC Number: 204-035-4
• MDL Number: MFCD00133939
• Beilstein Number: 8609690
• PubChem SID: 162227545; 24900773; 24890063
• PubChem CID: 9549168

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

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H332
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Pharmacology Properties

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

Product Information

• Purity: ≥95% (HPLC); ≥96.0% (HPLC)
• Empirical Formula (Hill Notation): C46H65N15O12S2

DETAILS

Sigma Aldrich - 94836

Amino Acid Sequence
Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Arg-Gly-NH2 [Disulfide bridge: 1-6]
Other Notes
Thyrotropin-releasing hormone1

Sigma Aldrich - V9879

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).