2-[2-(2-{2-[2-amino-2-(methanethioyl)acetamido]-3-(4-hydroxyphenyl)propanamido}-3-methylpentanamido)-3-hydroxybutanamido]-N-(1-{[({1-[(carbamoylmethyl)carbamoyl]-3-methylbutyl}carbamoyl)methyl]carbamoyl}-2-sulfanylethyl)butanediamide

• ChemBase ID: 103818
• Molecular Formular: C39H61N11O12S2
• Molecular Mass: 940.09814
• Monoisotopic Mass: 939.39425845
• SMILES: CCC(C)C(NC(=O)C(Cc1ccc(O)cc1)NC(=O)C(N)C=S)C(=O)NC(C(C)O)C(=O)NC(CC(=O)N)C(=O)NC(CS)C(=O)NCC(=O)NC(CC(C)C)C(=O)NCC(=O)N
• Canonical SMILES: CCC(C(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NCC(=O)N)CC(C)C)CS)CC(=O)N)C(O)C)NC(=O)C(NC(=O)C(C=S)N)Cc1ccc(cc1)O)C
• InChI: InChI=1S/C39H61N11O12S2/c1-6-19(4)31(49-37(60)25(46-33(56)23(40)16-63)12-21-7-9-22(52)10-8-21)38(61)50-32(20(5)51)39(62)47-26(13-28(41)53)36(59)48-27(17-64)35(58)44-15-30(55)45-24(11-18(2)3)34(57)43-14-29(42)54/h7-10,16,18-20,23-27,31-32,51-52,64H,6,11-15,17,40H2,1-5H3,(H2,41,53)(H2,42,54)(H,43,57)(H,44,58)(H,45,55)(H,46,56)(H,47,62)(H,48,59)(H,49,60)(H,50,61)
• InChIKey: SJRRTEZQOSELMP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[2-(2-{2-[2-amino-2-(methanethioyl)acetamido]-3-(4-hydroxyphenyl)propanamido}-3-methylpentanamido)-3-hydroxybutanamido]-N-(1-{[({1-[(carbamoylmethyl)carbamoyl]-3-methylbutyl}carbamoyl)methyl]carbamoyl}-2-sulfanylethyl)butanediamide
• IUPAC Traditional name: 2-[2-(2-{2-[2-amino-2-(methanethioyl)acetamido]-3-(4-hydroxyphenyl)propanamido}-3-methylpentanamido)-3-hydroxybutanamido]-N-{1-[({[1-(carbamoylmethylcarbamoyl)-3-methylbutyl]carbamoyl}methyl)carbamoyl]-2-sulfanylethyl}butanediamide
• Synonyms: Cys-Tyr-Ile-Thr-Asn-Cys-Gly-Leu-Gly-NH₂; [Thr^4,Gly^7]-OXYTOCIN

Database IDs

• CAS Number: 60786-59-6
• PubChem SID: 162091381
• PubChem CID: 44134880

CALCULATED PROPERTIES

• LogD (pH = 5.5): -6.112537
• LogD (pH = 7.4): -4.5768147
• Log P: -4.3092475
• Molar Refractivity: 235.741 cm^3
• Polarizability: 92.71405 Å^3
• Polar Surface Area: 385.46 Å^2
• Rotatable Bonds: 28
• Lipinski's Rule of Five: false
• Acid pKa: 9.373175
• H Acceptors: 13
• H Donor: 14

DETAILS

MP Biomedicals - 02152959

Contains disulfide bond between Cys1 and Cys6.
A selective oxytocin agonist.

REFERENCES

• Lowbridge, J., et al., Med. Chem., 20: 120 (1977).