(1S,2R,5S,10S,11S,15S)-14-(1-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-7-en-5-ol

• ChemBase ID: 167472
• Molecular Formular: C21H34O2
• Molecular Mass: 318.49346
• Monoisotopic Mass: 318.25588033
• SMILES: C1[C@@H](CC2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CCC1C(O)C)C)O
• Canonical SMILES: O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CCC2C(O)C)C)C1)C
• InChI: InChI=1S/C21H34O2/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/h4,13,15-19,22-23H,5-12H2,1-3H3/t13?,15-,16-,17?,18-,19-,20-,21+/m0/s1
• InChIKey: QAAQQTDJEXMIMF-PGDNBVRPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,10S,11S,15S)-14-(1-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-ol
• IUPAC Traditional name: (1S,2R,5S,10S,11S,15S)-14-(1-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-ol
• Synonyms: (3β,20R)-Pregn-5-ene-3,20-diol; Pregn-5-ene-3β,20β-diol; (20R)-Pregn-5-ene-3β,20-diol; 3β,20β-Dihydroxypregn-5-ene; Pregn-5-ene-3β,20(R)-diol; 20β-Dihydro Pregnenolone

Database IDs

• CAS Number: 901-57-5
• PubChem SID: 162261605
• PubChem CID: 71316100

CALCULATED PROPERTIES

• Acid pKa: 18.20429
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 3.3738575
• LogD (pH = 7.4): 3.3738577
• Log P: 3.3738577
• Molar Refractivity: 94.7848 cm^3
• Polarizability: 37.495953 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D446420

20β-Dihydro Pregnenolone is a metabolite of Pregnenolone (P712200).

REFERENCES

• Purdy, R., et al.: J. Med. Chem., 33, 1572 (1990)
• Bixo, M., et al.: Brain Res., 764, 173 (1990)
• Huang, X., et al.: J. Biol. Chem., 275, 29452 (1990)