Showing Metabocard for ursodeoxycholate (BASm0006596)

Common NameUrsodeoxycholate
DescriptionUrsodeoxycholic acid, also known as ursodeoxycholate or acid deoxyursocholic, belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. Ursodeoxycholic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
Molecular FormulaC24H40O4
Average Mass392.57200
Monoisotopic Mass392.29266
IUPAC Name(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
Traditional NameUrsodeoxycholic acid
CAS Registry Number128-13-2
SMILESC[C@H](CCC(=O)[O-])[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChI IdentifierInChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20+,22+,23+,24-/m1/s1
InChI KeyRUDATBOHQWOJDD-UZVSRGJWSA-N
CHEBI IDCHEBI:78604
HMDB IDHMDB0000946
StateSolid
Water Solubility1.97e-02 g/l
logP3.01
logS-4.30
pKa (Strongest Acidic)4.60
pKa (Strongest Basic)-0.54
Hydrogen Acceptor Count4
Hydrogen Donor Count3
Polar Surface Area77.76 Ų
Rotatable Bond Count4
Physiological Charge-1
Formal Charge0
Refractivity109.27 m³·mol⁻¹
Polarizability46.42

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