1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-7-en-14-yl](2H3)ethan-1-one

• ChemBase ID: 171154
• Molecular Formular: C21H32O3
• Molecular Mass: 332.47698
• Monoisotopic Mass: 332.23514488
• SMILES: [C@@]12(C(=CC[C@@H]3[C@@H]1CC[C@]1([C@H]3CC[C@@]1(C(=O)C)O)C)C[C@H](CC2)O)C
• Canonical SMILES: O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@]2(O)C(=O)C)C)C1)C
• InChI: InChI=1S/C21H32O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h4,15-18,23-24H,5-12H2,1-3H3/t15-,16+,17-,18-,19-,20-,21-/m0/s1
• InChIKey: JERGUCIJOXJXHF-TVWVXWENSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-14-yl](^2H₃)ethan-1-one
• IUPAC Traditional name: 1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-14-yl](^2H₃)ethanone
• Synonyms: (3β)-3,17-dihydroxypregn-5-en-20-one; 17α-Hydroxypregnenolone-21,21,21-d3; β,17-Dihydroxy-5-pregnen-20-one; 5-Pregnen-3β,17α-diol-20-one; NSC 63853; 17α-Hydroxy Pregnenolone-d3

Database IDs

• CAS Number: 105078-92-0
• PubChem SID: 164227064
• PubChem CID: 71434080

CALCULATED PROPERTIES

• Acid pKa: 12.699632
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.8339334
• LogD (pH = 7.4): 2.8339312
• Log P: 2.8339334
• Molar Refractivity: 95.1567 cm^3
• Polarizability: 37.560345 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 264-267°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H952322

A labelled metabolite of Pregnenolone (P712200).

REFERENCES

• Eiichi, T., et al.: J. Pharmacol. Sci., 95, 140 (1983)
• Kramer, R., et al.: J. Steroid Biochemi., 18, 715 (1983)
• Hiwatashi, A., et al.: J. Biochem., 98, 619 (1983)