2-[(4R)-4-[(1S,2S,5S,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanamido]acetic acid

• ChemBase ID: 169771
• Molecular Formular: C26H43NO6
• Molecular Mass: 465.62272
• Monoisotopic Mass: 465.3090381
• 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](CCC(=O)NCC(=O)O)C)C)C)O
• Canonical SMILES: O[C@H]1CC[C@]2([C@@H](C1)C[C@H]([C@@H]1[C@@H]2C[C@H](O)[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=O)NCC(=O)O)C)C)O)C
• InChI: InChI=1S/C26H43NO6/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33)/t14-,15+,16+,17-,18+,19+,20-,21+,24+,25+,26-/m1/s1
• InChIKey: RFDAIACWWDREDC-ACZMRKGOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4R)-4-[(1S,2S,5S,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanamido]acetic acid
• IUPAC Traditional name: [(4R)-4-[(1S,2S,5S,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanamido]acetic acid
• Synonyms: N-[(3β,5β,7α,12α)-3,7,12-Τrihydroxy-24-oxocholan-24-yl]glycine; 3β-N-Choloylglycine; 3β-Glycoreductodehydrocholic Acid; 3β,7α,12α-Trihydroxy-5β-cholanic Αcid-24-glycine; 3β-Cholylglycine; 3β-Glycine Cholate; 3β-Glycocholic Acid

Database IDs

• PubChem SID: 162263903
• PubChem CID: 12358463

CALCULATED PROPERTIES

• Acid pKa: 3.773337
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -0.35080916
• LogD (pH = 7.4): -1.8972445
• Log P: 1.3772112
• Molar Refractivity: 123.5928 cm^3
• Polarizability: 49.32588 Å^3
• Polar Surface Area: 127.09 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - G641355

Cholenoic acid present in significant proportions during early gastation.

REFERENCES

• Setchell, K., et al.: J. Biol. Chem. 263, 16637 (1988)
• Nakagawa, M., et al.: J. Lipid Res., 31, 1089 (1988)