ChemFOnt: Showing chemical card for Ursodeoxycholic acid (CFc000000755)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:14 UTC

Chemfont ID

CFc000000755

Molecule Identification

Common Name

Ursodeoxycholic acid

Definition

Ursodeoxycholic 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Ursodeoxycholate	Generator

Chemical Formula

C₂₄H₄₀O₄

Average Molecular Weight

392.572

Monoisotopic Molecular Weight

392.292659768

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

Traditional 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

CAS Registry Number

128-13-2

SMILES

[H][C@@](C)(CCC(O)=O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])[C@@]([H])(O)CC4([H])C[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C

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

Chemical Taxonomy

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

Functional Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 15185309)

Organ substructure

Adrenal cortex (HMDB: HMDB0000946)

Organ

Cell

Fibroblasts (HMDB: HMDB0000946)

Tissue

Muscle tissue

Skeletal muscle (HMDB: HMDB0000946)

Excreta

Biofluid or Excreta

Urine (PMID: 2621422)
Feces (PMID: 22664055)

Cellular substructure

Extracellular (HMDB: HMDB0000946)

Source

Exogenous

Exogenous (HMDB: HMDB0000946)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0000946)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Cystic fibrosis (MarkerDB: MDB00000289)
Cirrhosis (MarkerDB: MDB00000289)

Physical Properties

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022332

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ursodeoxycholic acid

METLIN ID

Not Available

PubChem Compound

13505246

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Sawada, Haruji; Kulprecha, Songsri; Nilubol, Naline; Yoshida, Toshiomi; Kinoshita, Shinichi; Taguchi, Hisaharu. Microbial production of ursodeoxycholic acid from lithocholic acid by Fusarium equiseti M41. Applied and Environmental Microbiology (1982), 44(6):1249-52

Showing chemical card for Ursodeoxycholic acid (CFc000000755)

MOL for CFc000000755 (Ursodeoxycholic acid)

3D MOL for CFc000000755 (Ursodeoxycholic acid)

3D SDF for CFc000000755 (Ursodeoxycholic acid)

3D-SDF for CFc000000755 (Ursodeoxycholic acid)

PDB for CFc000000755 (Ursodeoxycholic acid)

3D PDB for CFc000000755 (Ursodeoxycholic acid)

SMILES for CFc000000755 (Ursodeoxycholic acid)

INCHI for CFc000000755 (Ursodeoxycholic acid)

Structure for CFc000000755 (Ursodeoxycholic acid)

3D Structure for CFc000000755 (Ursodeoxycholic acid)