methyl (4R)-4-[(1R,2S,5S,7S,9S,10S,11S,14S,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoate

• ChemBase ID: 85859
• Molecular Formular: C25H42O5
• Molecular Mass: 422.59798
• Monoisotopic Mass: 422.30322444
• SMILES: O(C(=O)CC[C@H]([C@H]1[C@@]2([C@H]([C@@H]3[C@H]([C@@]4([C@@H](C[C@@H](O)CC4)C[C@@H]3O)C)C[C@@H]2O)CC1)C)C)C
• Canonical SMILES: COC(=O)CC[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
• InChI: InChI=1S/C25H42O5/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/h14-21,23,26-28H,5-13H2,1-4H3/t14-,15+,16+,17+,18+,19-,20+,21+,23-,24+,25-/m1/s1
• InChIKey: DLYVTEULDNMQAR-HNTWZPDDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (4R)-4-[(1R,2S,5S,7S,9S,10S,11S,14S,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoate
• IUPAC Traditional name: methyl (4R)-4-[(1R,2S,5S,7S,9S,10S,11S,14S,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoate
• Synonyms: Methyl cholate; Methyl 4-(3,7,12-trihydroxy-10,13-dimethylperhydrocyclopenta[a]phenanthren-17-yl)pentanoate

Database IDs

• CAS Number: 1448-36-8
• MDL Number: MFCD00064934
• PubChem SID: 162072975
• PubChem CID: 71299521

CALCULATED PROPERTIES

• Acid pKa: 18.296339
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.628388
• LogD (pH = 7.4): 2.6283884
• Log P: 2.6283884
• Molar Refractivity: 115.5584 cm^3
• Polarizability: 46.491676 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 155-156°C

Safety Information

• Storage Warning: Irritant