methyl (4S)-4-[(1S,2S,7S,9R,10R,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanoate

• ChemBase ID: 173866
• Molecular Formular: C25H40O5
• Molecular Mass: 420.5821
• Monoisotopic Mass: 420.28757438
• SMILES: C1C(=O)C[C@H]2[C@](C1)([C@@H]1[C@@H]([C@@H](C2)O)C2[C@]([C@H](C1)O)([C@H](CC2)[C@H](CCC(=O)OC)C)C)C
• Canonical SMILES: COC(=O)CC[C@@H]([C@H]1CCC2[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
• InChI: InChI=1S/C25H40O5/c1-14(5-8-22(29)30-4)17-6-7-18-23-19(13-21(28)25(17,18)3)24(2)10-9-16(26)11-15(24)12-20(23)27/h14-15,17-21,23,27-28H,5-13H2,1-4H3/t14-,15+,17+,18?,19-,20+,21-,23-,24-,25+/m0/s1
• InChIKey: CIZOGAIBGCZRCL-CREZPWRFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (4S)-4-[(1S,2S,7S,9R,10R,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanoate
• IUPAC Traditional name: methyl (4S)-4-[(1S,2S,7S,9R,10R,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanoate
• Synonyms: (5α,7α,12α)-7,12-Dihydroxy-3-oxo-cholan-24-oic Acid Methyl Ester; 7α,12α-Dihydroxy-3-oxo-5α-cholan-24-oic Acid Methyl Ester; Methyl 3-Keto-7α,12α-dihydroxy-5α-cholanoate

Database IDs

• CAS Number: 14772-92-0
• PubChem SID: 164229776
• PubChem CID: 71750409

CALCULATED PROPERTIES

• Acid pKa: 19.986677
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.8358889
• LogD (pH = 7.4): 2.8358893
• Log P: 2.8358893
• Molar Refractivity: 114.5303 cm^3
• Polarizability: 45.947132 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Methanol
• Apperance: Slightly Yellow Solid
• Melting Point: 120--123°C

DETAILS

Toronto Research Chemicals - M315050

Synthetic derivative of Petromyzonol, a bile salt derivative isolated from the sea lamprey (Petromyzon marinus ) ammocoete (larval form). May be used to study the biochemical characteristics of these and other compounds containing the allocholic acid rin

REFERENCES

• Haslewood, G., et al.: Biochem. J., 114, 179 (1969)
• Sorensen, P.W., et al.: J. Gen. Physiol., 105, 569 (1969)