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

• ChemBase ID: 153560
• Molecular Formular: C51H74N12O10S2
• Molecular Mass: 1079.33766
• Monoisotopic Mass: 1078.50922863
• SMILES: CCOc1ccc(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)N)CC(=O)N)C(C)C)Cc1ccccc1
• Canonical SMILES: CCOc1ccc(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)C(C)C)CC(=O)N)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N)CCCNC(=N)N
• InChI: InChI=1S/C51H74N12O10S2/c1-4-73-33-19-17-32(18-20-33)26-35-44(67)59-36(25-31-13-7-5-8-14-31)46(69)62-42(30(2)3)48(71)60-37(27-40(52)64)45(68)61-38(29-74-75-51(28-41(65)57-35)21-9-6-10-22-51)49(72)63-24-12-16-39(63)47(70)58-34(43(53)66)15-11-23-56-50(54)55/h5,7-8,13-14,17-20,30,34-39,42H,4,6,9-12,15-16,21-29H2,1-3H3,(H2,52,64)(H2,53,66)(H,57,65)(H,58,70)(H,59,67)(H,60,71)(H,61,68)(H,62,69)(H4,54,55,56)/t34-,35-,36-,37-,38-,39-,42-/m0/s1
• InChIKey: DRLYXDZRLDZVIS-RYGIWOHNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S)-1-[(10R,13S,16S,19S,22S)-19-benzyl-13-(carbamoylmethyl)-22-[(4-ethoxyphenyl)methyl]-12,15,18,21,24-pentaoxo-16-(propan-2-yl)-7,8-dithia-11,14,17,20,23-pentaazaspiro[5.19]pentacosane-10-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanamide
• IUPAC Traditional name: (2S)-2-{[(2S)-1-[(10R,13S,16S,19S,22S)-19-benzyl-13-(carbamoylmethyl)-22-[(4-ethoxyphenyl)methyl]-16-isopropyl-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-carbamimidamidopentanamide
• Synonyms: (d(CH2)51, Tyr(Et)2, Val4, Arg8, des-Gly-NH29)-Vasopressin; [des-Gly9-β-Mercapto-β,β-cyclopentamethylenepropionyl1,O-Et-Tyr2,Val4,Arg8]-Vasopressin

Database IDs

• CAS Number: 90332-81-3
• MDL Number: MFCD00076750
• PubChem SID: 162247699
• PubChem CID: 10418671

CALCULATED PROPERTIES

• Acid pKa: 11.334275
• H Acceptors: 13
• H Donor: 11
• LogD (pH = 5.5): -2.7370136
• LogD (pH = 7.4): -2.7288103
• Log P: -1.0262082
• Molar Refractivity: 293.4385 cm^3
• Polarizability: 110.44416 Å^3
• Polar Surface Area: 352.22 Å^2
• Rotatable Bonds: 17
• 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: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C51H74N12O10S2

DETAILS

Sigma Aldrich - V4503

Amino Acid Sequence
(1-Mercaptocyclohexyl)acetyl-Tyr(O-Ethyl)-Phe-Val-Asn-Cys-Pro-Arg-NH2 [Disulfide Bridge: 1-6]
Biochem/physiol Actions
Potent V1 (vasopressor) and V2 (antidiuretic) vasopressin receptor antagonist.