(3R)-3-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]butanoic acid

• ChemBase ID: 104045
• Molecular Formular: C23H38O4
• Molecular Mass: 378.54542
• Monoisotopic Mass: 378.2770097
• SMILES: O=C(O)C[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@@H]([C@@]4([C@H](CC3)C[C@H](O)CC4)C)C[C@H](O)[C@]12C
• Canonical SMILES: O[C@@H]1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2C[C@H](O)[C@]2([C@H]1CC[C@@H]2[C@@H](CC(=O)O)C)C)C
• InChI: InChI=1S/C23H38O4/c1-13(10-21(26)27)17-6-7-18-16-5-4-14-11-15(24)8-9-22(14,2)19(16)12-20(25)23(17,18)3/h13-20,24-25H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17-,18+,19+,20+,22+,23-/m1/s1
• InChIKey: PLRQOCVIINWCFA-AHFDLSHQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-3-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]butanoic acid; (3R)-3-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]butanoic acid
• IUPAC Traditional name: (3R)-3-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]butanoic acid; (3R)-3-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]butanoic acid
• Synonyms: 3,12-Dihydroxy-nor-cholanic Acid; NOR-DEOXYCHOLIC ACID; (3α,5β,12α)-3,12-Dihydroxy-24-norcholan-23-oic Acid; 23-Nordeoxycholic Acid; 24-Nordeoxycholic Acid; 3α,12α-Dihydroxy-24-nor-5β-cholan-23-oic Αcid; Nordeoxycholic Acid; Nor-Desoxycholic Acid

Database IDs

• CAS Number: 53608-86-9
• PubChem SID: 162091392
• PubChem CID: 193905

CALCULATED PROPERTIES

• H Donor: 3
• LogD (pH = 5.5): 2.3304691
• LogD (pH = 7.4): 0.5592086
• Log P: 3.3466907
• Molar Refractivity: 104.5958 cm^3
• Polarizability: 41.929417 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• Acid pKa: 4.526443
• H Acceptors: 4

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; Ethanol
• Apperance: White Solid
• Melting Point: 185-188°C

Safety Information

• Storage Condition: 0°C; Hygroscopic, -20°C Freezer, Under inert atmosphere
• Storage Warning: Hygroscopic

Product Information

• Purity: ≥98%

DETAILS

MP Biomedicals - 02154246

[3,12-Dihydroxy-nor-cholanic Acid] Purity ≥98%

Toronto Research Chemicals - N672000

A derivative of Deoxycholic acid (DC); the bile acid nor-DC showed considerable and continuing efflux into the perfusate; this involved mostly the unchanged acid. Nor-DC was not amidated but was metabolized to mostly ester glucuronides and hydroxylated de

REFERENCES

• Haslewood, G., et al.: Biochem. J., 62, 637 (1956)
• Clayton, L. M., et al.: J. Pharmacol. Exp. Therap., 248, 1130 (1956)
• Aggarwal, S., et al.: Steroids, 57, 107 (1956)
• Batta, A., et al.: J. Lipid Res., 33, 1403 (1956)