(2S)-2-{[(2S)-1-[(3R,6S,9S,12R,15S)-12-[(2S)-butan-2-yl]-9-(2-carbamoylethyl)-6-(carbamoylmethyl)-15-[(4-methoxyphenyl)methyl]-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentaazacycloicosane-3-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)-3,3-dimethylbutanamide

• ChemBase ID: 163627
• Molecular Formular: C45H69N11O12S
• Molecular Mass: 988.16086
• Monoisotopic Mass: 987.4847877
• SMILES: [C@@H]1(NC(=O)[C@@H](NC(=O)CCCSC[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC1=O)CCC(=O)N)CC(=O)N)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)(C)C)C(=O)NCC(=O)N)Cc1ccc(cc1)OC)[C@H](CC)C
• Canonical SMILES: CC[C@@H]([C@H]1NC(=O)[C@@H](NC(=O)CCCSC[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC1=O)CCC(=O)N)CC(=O)N)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)(C)C)C(=O)NCC(=O)N)Cc1ccc(cc1)OC)C
• InChI: InChI=1S/C45H69N11O12S/c1-7-24(2)36-42(65)51-27(16-17-32(46)57)38(61)52-29(21-33(47)58)39(62)53-30(23-69-19-9-11-35(60)50-28(40(63)54-36)20-25-12-14-26(68-6)15-13-25)44(67)56-18-8-10-31(56)41(64)55-37(45(3,4)5)43(66)49-22-34(48)59/h12-15,24,27-31,36-37H,7-11,16-23H2,1-6H3,(H2,46,57)(H2,47,58)(H2,48,59)(H,49,66)(H,50,60)(H,51,65)(H,52,61)(H,53,62)(H,54,63)(H,55,64)/t24-,27-,28-,29-,30-,31-,36+,37+/m0/s1
• InChIKey: GOANGOSGGZAITB-RPCPVKGFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S)-1-[(3R,6S,9S,12R,15S)-12-[(2S)-butan-2-yl]-9-(2-carbamoylethyl)-6-(carbamoylmethyl)-15-[(4-methoxyphenyl)methyl]-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentaazacycloicosane-3-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)-3,3-dimethylbutanamide
• IUPAC Traditional name: (2S)-2-{[(2S)-1-[(3R,6S,9S,12R,15S)-12-[(2S)-butan-2-yl]-9-(2-carbamoylethyl)-6-(carbamoylmethyl)-15-[(4-methoxyphenyl)methyl]-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentaazacycloicosane-3-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)-3,3-dimethylbutanamide
• Synonyms: 1-Butanoic Acid-2-(O-methyl-L-tyrosine)-1-carbaoxytocin; Deamino-2-O-methyltyrosine-1-carbaoxytocin; Depotocin; [2-O-Methyltyrosine]deamino-1-carba-oxytocin; Carbetocin

Database IDs

• CAS Number: 37025-55-1
• PubChem SID: 162257762
• PubChem CID: 71314505

CALCULATED PROPERTIES

• Acid pKa: 11.43711
• H Acceptors: 12
• H Donor: 10
• LogD (pH = 5.5): -3.572386
• LogD (pH = 7.4): -3.5724208
• Log P: -3.5723855
• Molar Refractivity: 249.9048 cm^3
• Polarizability: 98.02569 Å^3
• Polar Surface Area: 362.51 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C175925

An obstetric drug used to control postpartum hemorrhaging.

REFERENCES

• Sanz-Nebot, V., et al.: Anal. Bioanal. Chem., 377, 306 (2003)
• Gimpl, G., et al.: Eur. J. Pharmacol., 510, 9 (2003)
• Handler, J., et al.: Theriogenol., 66, 1397 (2003)
• Klenerova, V., et al.: J. Physiol. Pharmacol., 60, 57 (2003)