1-[(1S,2R,5S,9S,10S,11S,14S,15S)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-7-en-14-yl]ethan-1-one

• ChemBase ID: 171170
• Molecular Formular: C21H32O3
• Molecular Mass: 332.47698
• Monoisotopic Mass: 332.23514488
• SMILES: C1[C@@H](CC2=C[C@H]([C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CC[C@@H]1C(=O)C)C)O)O
• Canonical SMILES: O[C@H]1CC[C@]2(C(=C[C@H]([C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2C(=O)C)C)O)C1)C
• InChI: InChI=1S/C21H32O3/c1-12(22)15-4-5-16-19-17(7-9-21(15,16)3)20(2)8-6-14(23)10-13(20)11-18(19)24/h11,14-19,23-24H,4-10H2,1-3H3/t14-,15+,16-,17-,18+,19-,20-,21+/m0/s1
• InChIKey: UEWNVBNIVGLQPG-XXHSLLPRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(1S,2R,5S,9S,10S,11S,14S,15S)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-14-yl]ethan-1-one
• IUPAC Traditional name: 1-[(1S,2R,5S,9S,10S,11S,14S,15S)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-14-yl]ethanone
• Synonyms: (3β,7α)-3,7-Dihydroxypregn-5-en-20-one; 7α-Hydroxypregnenolone; 7α-Hydroxy Pregnenolone

Database IDs

• CAS Number: 30626-96-1
• PubChem SID: 164227080
• PubChem CID: 9967418

CALCULATED PROPERTIES

• Acid pKa: 18.204233
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.4285011
• LogD (pH = 7.4): 2.4285011
• Log P: 2.4285011
• Molar Refractivity: 95.1952 cm^3
• Polarizability: 37.560345 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H952415

7α-Hydroxy Pregnenolone is a hydroxylated metabolite of Pregnenolone (P712200).

REFERENCES

• Petkam, R. et al.: Gen Comp. Endocrinol., 131, 241 (2003)
• Morfin, R. et al.: J. Ster. Biochem. Mol. Biol., 50, 91 (2003)