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

• ChemBase ID: 176906
• Molecular Formular: C21H34O3
• Molecular Mass: 334.49286
• Monoisotopic Mass: 334.25079495
• SMILES: C1[C@@H](CC2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CC[C@@]1([C@H](O)C)O)C)O
• 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@H](O)C)C)C1)C
• InChI: InChI=1S/C21H34O3/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/h4,13,15-18,22-24H,5-12H2,1-3H3/t13-,15+,16-,17+,18+,19+,20+,21+/m1/s1
• InChIKey: XGUQCUDPXSTKLI-JGVMTBIOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,10R,11S,14R,15S)-14-[(1R)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-ene-5,14-diol
• IUPAC Traditional name: (1S,2R,5S,10R,11S,14R,15S)-14-[(1R)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-ene-5,14-diol
• Synonyms: Pregn-5-ene-3β,17,20β-triol; 3β,17α,20β-Trihydroxypregn-5-ene; (3β,20R)-Pregn-5-ene-3,17,20-triol

Database IDs

• CAS Number: 2204-13-9
• PubChem SID: 164232816
• PubChem CID: 71751760

CALCULATED PROPERTIES

• Acid pKa: 13.417368
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 2.448419
• LogD (pH = 7.4): 2.4484186
• Log P: 2.448419
• Molar Refractivity: 96.0819 cm^3
• Polarizability: 38.107162 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P712320

(3β,20R)-Pregn-5-ene-3,17,20-triol is a steroid metabolite of Pregnenolone (P712200).

REFERENCES

• Li, S., et al.: Chem. Phys. Lipids, 99, 33 (1999)
• Shackleton, C., et al.: Steroids, 64, 446 (1999)
• Ruan, B., et a.: J. Lipid Res., 42, 799 (1999)