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

• ChemBase ID: 176903
• Molecular Formular: C21H32O2
• Molecular Mass: 316.47758
• Monoisotopic Mass: 316.24023026
• SMILES: C1[C@H](CC2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CC[C@@H]1C(=O)C)C)O
• Canonical SMILES: O[C@@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2C(=O)C)C)C1)C
• InChI: InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3/t15-,16+,17-,18+,19+,20+,21-/m1/s1
• InChIKey: ORNBQBCIOKFOEO-QYYVTAPASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(1S,2R,5R,10S,11S,14S,15S)-5-hydroxy-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: pregnenolone
• Synonyms: (3α)-3-Hydroxypregn-5-en-20-one; 3α-Hydroxy-20-oxopregn-5-ene; Pregn-5-en-3α-ol-20-one; Δ5-Pregnen-3α-ol-20-one; 3-epi-Pregnenolone

Database IDs

• CAS Number: 19037-28-6
• PubChem SID: 164232813
• PubChem CID: 146469

CALCULATED PROPERTIES

• Acid pKa: 18.20429
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.5813584
• LogD (pH = 7.4): 3.5813584
• Log P: 3.5813584
• Molar Refractivity: 93.7567 cm^3
• Polarizability: 36.94731 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P712205

An epimer of Pregnenolone (P712200), a GABAA antagonist and increases neurogenesis in the hippocampus.

REFERENCES

• Li, W. et al.: J, Pharmacol. Exp. Therap., 323, 236 (2007)
• Sunol, C. et al.: J. Med. Chem., 49, 3225 (2007)