Bovine Metabolome Database: Showing metabocard for Ursodeoxycholic acid (BMDB0000946)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:38:59 UTC

Update Date

2020-05-11 20:50:44 UTC

BMDB ID

BMDB0000946

Secondary Accession Numbers

BMDB00946

Metabolite Identification

Common Name

Ursodeoxycholic acid

Description

Ursodeoxycholic acid, also known as ursodeoxycholate or actigall, 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
(3alpha,5beta,7beta)-3,7-Dihydroxycholan-24-Oic acid	ChEBI
3alpha,7beta-Dihydroxy-5beta-cholan-24-Oic acid	ChEBI
Actigall	ChEBI
Ursodeoxycholate	ChEBI
Ursodiol	ChEBI
Urso	Kegg
(3a,5b,7b)-3,7-Dihydroxycholan-24-Oate	Generator
(3a,5b,7b)-3,7-Dihydroxycholan-24-Oic acid	Generator
(3alpha,5beta,7beta)-3,7-Dihydroxycholan-24-Oate	Generator
(3Α,5β,7β)-3,7-dihydroxycholan-24-Oate	Generator
(3Α,5β,7β)-3,7-dihydroxycholan-24-Oic acid	Generator
3a,7b-Dihydroxy-5b-cholan-24-Oate	Generator
3a,7b-Dihydroxy-5b-cholan-24-Oic acid	Generator
3alpha,7beta-Dihydroxy-5beta-cholan-24-Oate	Generator
3Α,7β-dihydroxy-5β-cholan-24-Oate	Generator
3Α,7β-dihydroxy-5β-cholan-24-Oic acid	Generator
3 alpha,7 beta-Dihydroxy-5 beta-cholan-24-Oic acid	HMDB
Acid, deoxyursocholic	HMDB
Acid, ursacholic	HMDB
Acid, ursodeoxycholic	HMDB
Cholit-ursan	HMDB
Cholofalk	HMDB
Delursan	HMDB
Deoxyursocholic acid	HMDB
Ursochol	HMDB
Ursogal	HMDB
Ursolite	HMDB
Ursolvan	HMDB
Urso heumann	HMDB
Ursobilane	HMDB
Ursofalk	HMDB
Destolit	HMDB
Sodium ursodeoxycholate	HMDB
Ursacholic acid	HMDB
Ursodeoxycholate, sodium	HMDB
3 alpha,7 beta Dihydroxy 5 beta cholan 24 Oic acid	HMDB
Urdox	HMDB
(3a,5b,7b)-3,7-Dihydroxy-cholan-24-Oate	HMDB
(3a,5b,7b)-3,7-Dihydroxy-cholan-24-Oic acid	HMDB
3,7-Dihydroxycholan-24-Oic acid	HMDB
3-alpha,7-beta-Dihydroxy-5-beta-cholanoic acid	HMDB
3-alpha,7-beta-Dihydroxycholanic acid	HMDB
3-alpha,7-beta-Dioxycholanic acid	HMDB
Antigall	HMDB
Urosdesoxycholate	HMDB
Urosdesoxycholic acid	HMDB
Ursodeoxycholicacid	HMDB
Ursodexycholate	HMDB
Ursodexycholic acid	HMDB
Aventis brand OF ursodeoxycholic acid	HMDB
Axcan brand OF ursodeoxycholic acid	HMDB
Falk brand OF ursodeoxycholic acid	HMDB
Farmasa brand OF ursodeoxycholic acid	HMDB
Galen brand OF ursodeoxycholic acid	HMDB
Orphan brand OF ursodeoxycholic acid	HMDB
Antigen brand OF ursodeoxycholic acid	HMDB
CP Brand OF ursodeoxycholic acid	HMDB
Heumann brand OF ursodeoxycholic acid	HMDB
Niddapharm brand OF ursodeoxycholic acid	HMDB
Norgine brand OF ursodeoxycholic acid	HMDB
Sanofi synthelabo brand OF ursodeoxycholic acid	HMDB
Estedi brand OF ursodeoxycholic acid	HMDB
Provalis brand OF ursodeoxycholic acid	HMDB
Tramedico brand OF ursodeoxycholic acid	HMDB
Vita brand OF ursodeoxycholic acid	HMDB
Zambon brand OF ursodeoxycholic acid	HMDB

Chemical Formula

C₂₄H₄₀O₄

Average Molecular Weight

392.572

Monoisotopic Molecular Weight

392.292659768

IUPAC Name

(4R)-4-[(1S,2S,5R,7S,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,5R,7S,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@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

bile acid (CHEBI:9907 )
dihydroxy-5beta-cholanic acid (CHEBI:9907 )
C24 bile acids, alcohols, and derivatives (C07880 )
Cholane and derivatives (C07880 )
C24 bile acids, alcohols, and derivatives (LMST04010033 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	46.42 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01rt-0419000000-6a92f910581240163a99	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0006-1110390000-52bc66ab11fd14425d4f	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0a4l-3940000000-cf90a6f216d592e2ad4c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-00di-0029000000-54929e08fef761ba2b28	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0002-2911000000-eec2b269eeb08a30ac6e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0009000000-997e61e986e67265241c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-0009000000-81134947694f847d1c65	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02t9-1219000000-6a0ddebebacac090c27e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-efdaad69eee0ae934dd5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-1009000000-15b4edab9d05e4c3693a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9006000000-9291e69db3a3c47ecd97	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-7631731446db77938069	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-0009000000-39e7e555dc6b36ada2af	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-1009000000-351c21e3dab693818b22	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0019000000-56dc67f71a8507c1433f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-3039000000-510702cae19e3906b6e1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9550000000-7486a5f56afd302efa7e	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm

Biospecimen Locations

Adrenal Cortex
Bladder
Fibroblasts
Intestine
Liver
Placenta
Skeletal Muscle

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adrenal Cortex	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Bladder	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Skeletal Muscle	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000946

DrugBank ID

DB01586

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ursodiol

METLIN ID

5893

PubChem Compound

31401

PDB ID

Not Available

ChEBI ID

9907

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(

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Ursodeoxycholic acid (BMDB0000946)

Structure for BMDB0000946 (Ursodeoxycholic acid)