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

• ChemBase ID: 179137
• Molecular Formular: C27H48O3
• Molecular Mass: 420.66822
• Monoisotopic Mass: 420.3603454
• SMILES: C1[C@H](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)O
• 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)CC[C@H](C2)O)C)C
• InChI: InChI=1S/C27H48O3/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/h16-25,28-30H,6-15H2,1-5H3/t17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1
• InChIKey: RIVQQZVHIVNQFH-XJZYBRFWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane-5,9,16-triol
• IUPAC Traditional name: trihydroxycoprostane
• Synonyms: (3α,5β,7α,12α)-Cholestane-3,7,12-triol; 3α,7α,12α-Trihydroxycoprostane; Trihydroxycoprostane

Database IDs

• CAS Number: 547-96-6
• PubChem SID: 164235047
• PubChem CID: 160520

CALCULATED PROPERTIES

• Lipinski's Rule of Five: true
• Acid pKa: 18.296339
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 4.978892
• LogD (pH = 7.4): 4.978893
• Log P: 4.978893
• Molar Refractivity: 122.8745 cm^3
• Polarizability: 49.40406 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 5

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 180-181°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - T795150

A sterol, similar to cholesterol and is a substrate for the sterol 27-hydroxylase enzyme in the bile salt synthetic pathway. The accumulation of this compound in urine can manifest as jaundice or, in more extreme cases, is a sign of Xanthomatosis.

REFERENCES

• Honda, A., et al.: J. Biol. Chem., 276, 34579 (2001)
• Krasowski, M., et al.: Mol. Endocrinol., 19, 1720 (2001)
• Mast, N., et al.: Biochem., 45, 4396 (2001)