Livestock Metabolome Database: Showing metabocard for Ursodeoxycholic acid (LMDB00283)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:46:23 UTC

Update Date

2016-08-02 20:15:04 UTC

Lmdb

LMDB00283

Secondary Accession Numbers

None

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

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

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

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Plasma

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	20231903	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	Natalja P. Nørsko...	details