(1S,2S,7R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.02,7.011,15]heptadecan-5-one

• ChemBase ID: 167793
• Molecular Formular: C27H46O3
• Molecular Mass: 418.65234
• Monoisotopic Mass: 418.34469533
• SMILES: C1C(=O)C[C@@H]2[C@](C1)([C@@H]1[C@@H]([C@@H](C2)O)[C@H]2[C@]([C@H](C1)O)([C@H](CC2)[C@@H](CCCC(C)C)C)C)C
• Canonical SMILES: CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)[C@@H](O)C[C@H]1[C@H]2[C@H](O)C[C@H]2[C@]1(C)CCC(=O)C2)C)C
• InChI: InChI=1S/C27H46O3/c1-16(2)7-6-8-17(3)20-9-10-21-25-22(15-24(30)27(20,21)5)26(4)12-11-19(28)13-18(26)14-23(25)29/h16-18,20-25,29-30H,6-15H2,1-5H3/t17-,18+,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1
• InChIKey: HHVQPBXBALLUDF-QORHGLQKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,7R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-one
• IUPAC Traditional name: (1S,2S,7R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-one
• Synonyms: (5β,7α,12α)-7,12-Dihydroxy-cholestan-3-one; 7α,12α-Dihydroxy-5β-cholestan-3-one

Database IDs

• CAS Number: 547-97-7
• PubChem SID: 162261926
• PubChem CID: 5284271

CALCULATED PROPERTIES

• Acid pKa: 19.986677
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.1863933
• LogD (pH = 7.4): 5.1863933
• Log P: 5.1863933
• Molar Refractivity: 121.8464 cm^3
• Polarizability: 48.85596 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 202-205°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D452410

Substrate for 3α-Hydroxysteroid Dehydrogenase in primary bile acid biosynthesis.

REFERENCES

• Aringer, L., et al.: J. Lip. Res., 16, 426 (1965)
• Berseus, O., et al.: J. Biol. Chem., 240, 2396 (1965)
• Berseus, O., et al.: Eur. J. Biochem., 2, 503 (1965)