(2S)-2-{[(2S)-1-[(10R,13S,16S,19S,22S)-19-benzyl-16-(2-carbamoylethyl)-13-(carbamoylmethyl)-22-[(4-methoxyphenyl)methyl]-12,15,18,21,24-pentaoxo-7,8-dithia-11,14,17,20,23-pentaazaspiro[5.19]pentacosane-10-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamido-N-(carbamoylmethyl)pentanamide

• ChemBase ID: 132639
• Molecular Formular: C52H74N14O12S2
• Molecular Mass: 1151.36056
• Monoisotopic Mass: 1150.50520588
• SMILES: COc1ccc(cc1)C[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC2(CCCCC2)CC(=O)N1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(=N)N)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N)Cc1ccccc1
• Canonical SMILES: COc1ccc(cc1)C[C@@H]1NC(=O)CC2(CCCCC2)SSC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC1=O)Cc1ccccc1)CCC(=O)N)CC(=O)N)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)NCC(=O)N)CCCNC(=N)N
• InChI: InChI=1S/C52H74N14O12S2/c1-78-32-16-14-31(15-17-32)25-35-46(73)63-36(24-30-10-4-2-5-11-30)47(74)61-34(18-19-40(53)67)45(72)64-37(26-41(54)68)48(75)65-38(29-79-80-52(27-43(70)60-35)20-6-3-7-21-52)50(77)66-23-9-13-39(66)49(76)62-33(12-8-22-58-51(56)57)44(71)59-28-42(55)69/h2,4-5,10-11,14-17,33-39H,3,6-9,12-13,18-29H2,1H3,(H2,53,67)(H2,54,68)(H2,55,69)(H,59,71)(H,60,70)(H,61,74)(H,62,76)(H,63,73)(H,64,72)(H,65,75)(H4,56,57,58)/t33-,34-,35-,36-,37-,38-,39-/m0/s1
• InChIKey: QVQOGNOOAMQKCE-ZTYVOHGWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S)-1-[(10R,13S,16S,19S,22S)-19-benzyl-16-(2-carbamoylethyl)-13-(carbamoylmethyl)-22-[(4-methoxyphenyl)methyl]-12,15,18,21,24-pentaoxo-7,8-dithia-11,14,17,20,23-pentaazaspiro[5.19]pentacosane-10-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamido-N-(carbamoylmethyl)pentanamide
• IUPAC Traditional name: (2S)-2-{[(2S)-1-[(10R,13S,16S,19S,22S)-19-benzyl-16-(2-carbamoylethyl)-13-(carbamoylmethyl)-22-[(4-methoxyphenyl)methyl]-12,15,18,21,24-pentaoxo-7,8-dithia-11,14,17,20,23-pentaazaspiro[5.19]pentacosane-10-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamido-N-(carbamoylmethyl)pentanamide
• Synonyms: [β-Mercapto-β,β-cyclopentamethylenepropionyl1, O-me-Tyr2, Arg8]-Vasopressin

Database IDs

• CAS Number: 73168-24-8
• MDL Number: MFCD00076747
• PubChem SID: 162226916
• PubChem CID: 9833460

CALCULATED PROPERTIES

• Acid pKa: 11.26995
• H Acceptors: 15
• H Donor: 13
• LogD (pH = 5.5): -6.2466745
• LogD (pH = 7.4): -6.23703
• Log P: -4.4922843
• Molar Refractivity: 305.1104 cm^3
• Polarizability: 114.82467 Å^3
• Polar Surface Area: 424.41 Å^2
• Rotatable Bonds: 20
• 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

Pharmacology Properties

• Gene Information: human ... AVPR1A(552)mouse ... AVPR1A(54140)rat ... AVPR1A(25107)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - V2255

Amino Acid Sequence
(1-Mercaptocyclohexyl)acetyl-Tyr-OMet-Phe-Gln-Asn-Cys-Pro-Arg-Gly-NH2 [Disulfide Bridge: 1-6]
Biochem/physiol Actions
V1a selective vasopressin receptor antagonist.