AFCDB: Ursodeoxycholic acid (FDB022332)

Record Information

Version

1.0

Creation date

2011-09-21 00:12:17 UTC

Update date

2015-10-09 22:29:37 UTC

Primary ID

FDB022332

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Ursodeoxycholic acid

Description

Ursodeoxycholic acid, also known as ursodeoxycholate, 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 an extremely weak basic (essentially neutral) compound (based on its pKa).

CAS Number

128-13-2

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.02 g/L	ALOGPS
logP	3.01	ALOGPS
logP	3.71	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.6	ChemAxon
pKa (Strongest Basic)	-0.54	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.27 m³·mol⁻¹	ChemAxon
Polarizability	46.88 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C24H40O4

IUPAC name

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

InChI Identifier

InChI=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 Key

RUDATBOHQWOJDD-ROKSHQGPSA-N

Isomeric SMILES

[H][C@@](C)(CCC(O)=O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])[C@@]([H])(O)CC4C[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C

Average Molecular Weight

392.572

Monoisotopic Molecular Weight

392.292659768

Classification

Description

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Dihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Dihydroxy bile acid, alcohol, or derivatives
7-hydroxysteroid
7-alpha-hydroxysteroid
3-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Not Available

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

DB01586

HMDB ID

HMDB00946

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Ursodeoxycholic acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
bitter	Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Ursodeoxycholic acid (FDB022332)

Structure for FDB022332 (Ursodeoxycholic acid)