(1S,2S,5R,7R,10R,11S,14S,15S)-14-[1-hydroxy(2H4)ethyl]-2,15-dimethyl(14-2H)tetracyclo[8.7.0.02,7.011,15]heptadecan-5-ol

• ChemBase ID: 176892
• Molecular Formular: C21H36O2
• Molecular Mass: 320.50934
• Monoisotopic Mass: 320.27153039
• SMILES: C1[C@H](C[C@@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H](CC2)C(O)C)C)C)O
• 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]2C(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-/m1/s1
• InChIKey: YWYQTGBBEZQBGO-WDDCBOSHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5R,7R,10R,11S,14S,15S)-14-[1-hydroxy(^2H₄)ethyl]-2,15-dimethyl(14-^2H)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-ol
• IUPAC Traditional name: (1S,2S,5R,7R,10R,11S,14S,15S)-14-[1-hydroxy(^2H₄)ethyl]-2,15-dimethyl(14-^2H)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-ol
• Synonyms: (3α,5β),20S)-Pregnane-3,20-diol; 3α,20α-Dihydroxy-5βpregnane-d5; NSC 1612-d5; NSC 47462-d5; Pregnanediol-d5; 5β-Pregnane-3α,20α-diol-d5

Database IDs

• PubChem SID: 164232802
• PubChem CID: 71751754

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

DETAILS

Toronto Research Chemicals - P705132

Labelled 5β-Pregnane-3α,20α-diol, 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., 88,