(4R)-4-[(1S,2R,5S,7R,8S,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanoic acid

• ChemBase ID: 171474
• Molecular Formular: C24H40O4
• Molecular Mass: 392.572
• Monoisotopic Mass: 392.29265976
• SMILES: C1C[C@@H](C[C@@H]2[C@]1([C@@H]1[C@@H](C[C@@H]2O)[C@H]2[C@](CC1)([C@H](CC2)[C@@H](CCC(=O)O)C)C)C)O
• Canonical SMILES: O[C@H]1CC[C@]2([C@@H](C1)[C@@H](O)C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=O)O)C)C)C
• InChI: InChI=1S/C24H40O4/c1-14(4-7-22(27)28)17-5-6-18-16-13-21(26)20-12-15(25)8-10-24(20,3)19(16)9-11-23(17,18)2/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16+,17-,18+,19+,20+,21+,23-,24-/m1/s1
• InChIKey: DGABKXLVXPYZII-MMTMODRTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-[(1S,2R,5S,7R,8S,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanoic acid
• IUPAC Traditional name: β-hyodeoxycholic acid
• Synonyms: (3β,5β,6α)-3,6-Dihydroxycholan-24-oic Acid; 3β,6α-dihydroxy-5β-Cholan-24-oic Acid; Isohyodeoxycholic Acid; β-Hyodeoxycholic Acid

Database IDs

• CAS Number: 570-84-3
• PubChem SID: 164227384
• PubChem CID: 5283822

CALCULATED PROPERTIES

• Acid pKa: 4.791043
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.9274719
• LogD (pH = 7.4): 1.1525321
• Log P: 3.7133055
• Molar Refractivity: 109.2738 cm^3
• Polarizability: 43.768806 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 117-121°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H998105

A potential bile acid metabolite.

REFERENCES

• Abadie, C., et al.: Biochem. J., 299, 725 (1994)
• Taniguchi, T., et al.: J. Biol. Chem., 269, 10071 (1994)
• Davis, R., et al.: J. Lipid Res., 43, 533 (1994)