(1S,5S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.02,7.011,15]heptadec-2(7)-ene-5,14-diol

• ChemBase ID: 167853
• Molecular Formular: C18H28O2
• Molecular Mass: 276.41372
• Monoisotopic Mass: 276.20893014
• SMILES: C1[C@@H](CC2=C(C1)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H](CC2)O)C)O
• Canonical SMILES: O[C@H]1CCC2=C(C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C
• InChI: InChI=1S/C18H28O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h12,14-17,19-20H,2-10H2,1H3/t12-,14+,15+,16-,17-,18-/m0/s1
• InChIKey: IBHQSODTBQCZDA-MACGOEAWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-2(7)-ene-5,14-diol
• IUPAC Traditional name: (1S,5S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-2(7)-ene-5,14-diol
• Synonyms: (3β,17β)-Estr-5(10)-ene-3,17-diol; 3β,17β-Dihydroxy-19-norandrost-5(10)-ene

Database IDs

• CAS Number: 4993-32-2
• PubChem SID: 162261986
• PubChem CID: 9814177

CALCULATED PROPERTIES

• Acid pKa: 18.21662
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.4544723
• LogD (pH = 7.4): 2.4544723
• Log P: 2.4544723
• Molar Refractivity: 80.7395 cm^3
• Polarizability: 31.964787 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D453800

A metabolite of Androstenedione. A novel 19-norsteroid, from androstenedione and 19-hydroxyandrostenedione by cultured porcine granulosa cells is reported for the first time.

REFERENCES

• Haarbo, J., et al.: Clin. Physiol., 11, 331 (1991)
• Krebs-Smith, S., et al.: Eur. J. Clin. Nutr., 54, 281(1991)
• Rasmussen, B., et al.: J. Clin. Endocrinol. Metab., 85, 55 (1991)