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

• ChemBase ID: 89046
• Molecular Formular: C24H40O5
• Molecular Mass: 408.5714
• Monoisotopic Mass: 408.28757438
• SMILES: O=C(O)CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@@H]([C@@]4([C@H](C[C@H](O)CC4)C[C@H]3O)C)C[C@H](O)[C@]12C
• 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)O)C)C)O)C
• InChI: InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14-,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
• InChIKey: BHQCQFFYRZLCQQ-PGHAKIONSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
• IUPAC Traditional name: (4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
• Synonyms: 3-a-7-a-12-a-Trihydroxy-5-a-cholanoic acid; Allocholic acid

Database IDs

• CAS Number: 2464-18-8
• MDL Number: MFCD00269872
• PubChem SID: 162075932
• PubChem CID: 160636

CALCULATED PROPERTIES

• Acid pKa: 4.4750123
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 1.4196734
• LogD (pH = 7.4): -0.346591
• Log P: 2.4824944
• Molar Refractivity: 110.7893 cm^3
• Polarizability: 44.403893 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 238-240°C

Safety Information

• Storage Warning: Irritant/Store at -20°C

DETAILS

Apollo Scientific Ltd - OR4500T

Found in a number of sources, including man as a manorbiliary metabolite.