3-(2-amino-3-methylbutanamido)-3-({13-benzyl-4-[2-({4-carbamimidamido-1-[(carboxymethyl)carbamoyl]butyl}carbamoyl)pyrrolidine-1-carbonyl]-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-19-yl}carbamoyl)propanoic acid

• ChemBase ID: 130927
• Molecular Formular: C55H78N16O17S2
• Molecular Mass: 1299.43482
• Monoisotopic Mass: 1298.51722712
• SMILES: CC(C)C(C(=O)NC(CC(=O)O)C(=O)NC1CSSCC(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)Cc1ccc(cc1)O)Cc1ccccc1)CCC(=O)N)CC(=O)N)C(=O)N1CCCC1C(=O)NC(CCCNC(=N)N)C(=O)NCC(=O)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)O)CCCNC(=N)N)NC(=O)C(NC(=O)C(C(C)C)N)CC(=O)O
• InChI: InChI=1S/C55H78N16O17S2/c1-27(2)44(58)53(87)68-36(23-42(75)76)50(84)69-37-25-89-90-26-38(54(88)71-19-7-11-39(71)52(86)64-31(10-6-18-61-55(59)60)45(79)62-24-43(77)78)70-49(83)35(22-41(57)74)67-46(80)32(16-17-40(56)73)63-47(81)33(20-28-8-4-3-5-9-28)65-48(82)34(66-51(37)85)21-29-12-14-30(72)15-13-29/h3-5,8-9,12-15,27,31-39,44,72H,6-7,10-11,16-26,58H2,1-2H3,(H2,56,73)(H2,57,74)(H,62,79)(H,63,81)(H,64,86)(H,65,82)(H,66,85)(H,67,80)(H,68,87)(H,69,84)(H,70,83)(H,75,76)(H,77,78)(H4,59,60,61)
• InChIKey: PRWNILGOKADWST-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(2-amino-3-methylbutanamido)-3-({13-benzyl-4-[2-({4-carbamimidamido-1-[(carboxymethyl)carbamoyl]butyl}carbamoyl)pyrrolidine-1-carbonyl]-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-19-yl}carbamoyl)propanoic acid
• IUPAC Traditional name: 3-(2-amino-3-methylbutanamido)-3-{[13-benzyl-4-(2-{[4-carbamimidamido-1-(carboxymethylcarbamoyl)butyl]carbamoyl}pyrrolidine-1-carbonyl)-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-19-yl]carbamoyl}propanoic acid
• Synonyms: Val-Asp-[Arg8]-Vasopressin

Database IDs

• CAS Number: 100930-18-5
• MDL Number: MFCD00076742
• PubChem SID: 162225205
• PubChem CID: 25081413

CALCULATED PROPERTIES

• Acid pKa: 3.1514268
• H Acceptors: 21
• H Donor: 18
• LogD (pH = 5.5): -10.632442
• LogD (pH = 7.4): -10.686079
• Log P: -10.629107
• Molar Refractivity: 330.6896 cm^3
• Polarizability: 125.03187 Å^3
• Polar Surface Area: 551.14 Å^2
• Rotatable Bonds: 26
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20
• Safety Statements: 36
• 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

Product Information

• Purity: ≥95% (HPLC)

DETAILS

Sigma Aldrich - V5253

Amino Acid Sequence
Val-Asp-Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Arg-Gly-NH2 [Disulfide Bridge: 1-6]
Biochem/physiol Actions
Has natriuretic activity equivalent to Arg8-vasopressin with low pressor activity
Other Notes
Originally isolated from bovine posterior pituitary, thought to be a storage form of Arg8-vasopressin