methyl (4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanoate

• ChemBase ID: 173803
• Molecular Formular: C25H40O4
• Molecular Mass: 404.5827
• Monoisotopic Mass: 404.29265976
• SMILES: C1C(=O)C[C@@H]2[C@](C1)([C@@H]1[C@@H]([C@@H](C2)O)[C@H]2[C@](CC1)([C@H](CC2)[C@@H](CCC(=O)OC)C)C)C
• Canonical SMILES: COC(=O)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2[C@H](O)C[C@H]2[C@]1(C)CCC(=O)C2)C
• InChI: InChI=1S/C25H40O4/c1-15(5-8-22(28)29-4)18-6-7-19-23-20(10-12-25(18,19)3)24(2)11-9-17(26)13-16(24)14-21(23)27/h15-16,18-21,23,27H,5-14H2,1-4H3/t15-,16+,18-,19+,20+,21-,23+,24+,25-/m1/s1
• InChIKey: XHRLTYUHWGHDCJ-WZAAVQHPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanoate
• IUPAC Traditional name: methyl (4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanoate
• Synonyms: 7α-Hydroxy-3-oxo-5β-cholan-24-oic Acid Methyl Ester; 7α-Hydroxy-3-oxo-5β-cholanic Acid Methyl Ester; Methyl 7α-Hydroxy-3-oxo-5β-cholan-24-oate; Methyl-3-keto-7α-hydroxy-5β-cholanoate; Methyl 7α-Hydroxy-3-ketocholanoate

Database IDs

• CAS Number: 14773-00-3
• PubChem SID: 164229713
• PubChem CID: 11750068

CALCULATED PROPERTIES

• Acid pKa: 19.987846
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.0667005
• LogD (pH = 7.4): 4.0667005
• Log P: 4.0667005
• Molar Refractivity: 113.0148 cm^3
• Polarizability: 45.31572 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol; Toluene
• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - M312755

Steroidal fused pyrazoles useful as bile acid transporters.

REFERENCES

• Bhat, L. et al.; Bioorgan. Med. Chem. 15, 85 (2005)