(2R,3S)-2-[(1S,2R,5S,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-7-en-14-yl]-6-methylheptane-2,3-diol

• ChemBase ID: 167796
• Molecular Formular: C27H46O3
• Molecular Mass: 418.65234
• Monoisotopic Mass: 418.34469533
• SMILES: C1[C@@H](CC2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CC[C@@H]1[C@]([C@H](CCC(C)C)O)(O)C)C)O
• Canonical SMILES: CC(CC[C@@H]([C@@]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)O)(O)C)O)C
• InChI: InChI=1S/C27H46O3/c1-17(2)6-11-24(29)27(5,30)23-10-9-21-20-8-7-18-16-19(28)12-14-25(18,3)22(20)13-15-26(21,23)4/h7,17,19-24,28-30H,6,8-16H2,1-5H3/t19-,20-,21-,22-,23-,24-,25-,26-,27+/m0/s1
• InChIKey: ISBSSBGEYIBVTO-OFCXPOQJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-2-[(1S,2R,5S,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-14-yl]-6-methylheptane-2,3-diol
• IUPAC Traditional name: (2R,3S)-2-[(1S,2R,5S,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-14-yl]-6-methylheptane-2,3-diol
• Synonyms: (3β,22S)-Cholest-5-ene-3,20,22-triol; (22S)-Cholest-5-ene-3β,20,22-triol; (20R,22S)-20,22-Dihydroxycholesterol; 20α,22S-Dihydroxycholesterol; (3β,22S)-Dihydroxy Cholesterol

Database IDs

• CAS Number: 26649-05-8
• PubChem SID: 162261929
• PubChem CID: 59184514

CALCULATED PROPERTIES

• Acid pKa: 13.605227
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 4.7227783
• LogD (pH = 7.4): 4.722778
• Log P: 4.7227783
• Molar Refractivity: 123.6601 cm^3
• Polarizability: 49.16483 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D452470

A metabolite of Cholesterol (C432501). Cholesterol is metabolized to Pregnenolone by way of 22R-hydroxycholesterol and 20R,22R-dihydroxycholesterol by P 450scc.

REFERENCES

• Sugano, S., et al.: J. Biochem., 120, 780 (1996)