4-{[(1S,2R,10S,11S,14S,15S,17R)-14-acetyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-17-yl]oxy}-4-oxobutanoic acid

• ChemBase ID: 6157
• Molecular Formular: C25H34O6
• Molecular Mass: 430.53386
• Monoisotopic Mass: 430.23553881
• SMILES: C1CC(=O)C=C2CC[C@@H]3[C@@H]([C@@]12C)[C@H](OC(=O)CCC(=O)O)C[C@]1([C@H]3CC[C@@H]1C(=O)C)C
• Canonical SMILES: O=C(O[C@@H]1C[C@@]2(C)[C@H]([C@H]3[C@H]1[C@@]1(C)CCC(=O)C=C1CC3)CC[C@@H]2C(=O)C)CCC(=O)O
• InChI: InChI=1S/C25H34O6/c1-14(26)18-6-7-19-17-5-4-15-12-16(27)10-11-24(15,2)23(17)20(13-25(18,19)3)31-22(30)9-8-21(28)29/h12,17-20,23H,4-11,13H2,1-3H3,(H,28,29)/t17-,18+,19-,20+,23+,24-,25+/m0/s1
• InChIKey: JBBNFGYRYNBDIH-DBGGZKJISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(1S,2R,10S,11S,14S,15S,17R)-14-acetyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-17-yl]oxy}-4-oxobutanoic acid
• IUPAC Traditional name: 4-{[(1S,2R,10S,11S,14S,15S,17R)-14-acetyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-17-yl]oxy}-4-oxobutanoic acid
• Synonyms: PROGESTERONE-11-ALPHA-OL-HEMISUCCINATE

Database IDs

• PubChem SID: 99445018; 160969582
• PubChem CID: 5289373

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.2153034
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.8016149
• LogD (pH = 7.4): 0.082842246
• Log P: 3.1058278
• Molar Refractivity: 114.3426 cm^3
• Polarizability: 45.08079 Å^3
• Polar Surface Area: 97.74 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.2
• LOG S: -4.7
• Solubility (Water): 8.50e-03 g/l

DETAILS

DrugBank - DB08547

Drug information: experimental