(1S,2S,5R,7R,10R,11S,14S,15S)-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol

• ChemBase ID: 111219
• Molecular Formular: C21H36O2
• Molecular Mass: 320.50934
• Monoisotopic Mass: 320.27153039
• SMILES: O[C@@H]1CC[C@]2([C@H](CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@H]23)[C@@H](O)C)C1)C
• Canonical SMILES: O[C@@H]1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](O)C)C)C
• InChI: InChI=1S/C21H36O2/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/h13-19,22-23H,4-12H2,1-3H3/t13-,14+,15+,16-,17+,18-,19-,20-,21+/m0/s1
• InChIKey: YWYQTGBBEZQBGO-BERLURQNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5R,7R,10R,11S,14S,15S)-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol; (1S,2S,5R,7R,10R,11S,14S,15S)-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-ol
• IUPAC Traditional name: pregnanediol
• Synonyms: PREGNANE-3α-20α-DIOL; 5β-Pregnane-3α,20α-diol; Pregnanediol; (3α,5β),20S)-Pregnane-3,20-diol; 3α,20α-Dihydroxy-5βpregnane; NSC 1612; NSC 47462; Pregnanediol; 5β-Pregnane-3α,20α-diol

Database IDs

• CAS Number: 80-92-2
• PubChem SID: 162103047
• PubChem CID: 219833
• CHEMBL: 269897
• Chemspider ID: 190585
• Unique Ingredient Identifier: JR3JD1Y22C
• Wikipedia Title: Pregnanediol

CALCULATED PROPERTIES

• Acid pKa: 18.296396
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 3.779437
• LogD (pH = 7.4): 3.779437
• Log P: 3.779437
• Molar Refractivity: 93.9348 cm^3
• Polarizability: 37.734753 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol
• Apperance: White Solid
• Melting Point: 240-242°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

MP Biomedicals - 05218199

MP Biomedicals Rare Chemical collection

Toronto Research Chemicals - P705130

5β-Pregnane-3α,20α-diol is a metabolite of Progesterone (P755900).

REFERENCES

• Beall, et al.: Biochem. J., 31, 35 (1937)
• Okuda, A., et al.: J. Biol. Chem., 259, 7519 (1937)
• Russell, D., et al.: Biochemistry, 31, 4737 (1937)
• Kondo, K., et al.: Eur. J. Biochem., 219, 357 (1937)
• Westerbacka, J., et al.: J. Clin. Endocrinol. Metab.,