Bovine Metabolome Database: Showing metabocard for 3b,12a-Dihydroxy-5b-cholanoic acid (BMDB0000438)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:30:45 UTC

Update Date

2020-05-11 20:20:54 UTC

BMDB ID

BMDB0000438

Secondary Accession Numbers

BMDB00438

Metabolite Identification

Common Name

3b,12a-Dihydroxy-5b-cholanoic acid

Description

3b,12a-Dihydroxy-5b-cholanoic acid, also known as 3-epideoxycholic acid or (3b,5b,12a)-3,12-dihydroxycholan-24-Oate, 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. 3b,12a-Dihydroxy-5b-cholanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3beta,5beta,12alpha)-3,12-Dihydroxycholan-24-Oic acid	ChEBI
3-Epideoxycholic acid	ChEBI
3beta-Deoxycholic acid	ChEBI
Isodeoxycholic acid	ChEBI
(3b,5b,12a)-3,12-Dihydroxycholan-24-Oate	Generator
(3b,5b,12a)-3,12-Dihydroxycholan-24-Oic acid	Generator
(3beta,5beta,12alpha)-3,12-Dihydroxycholan-24-Oate	Generator
(3Β,5β,12α)-3,12-dihydroxycholan-24-Oate	Generator
(3Β,5β,12α)-3,12-dihydroxycholan-24-Oic acid	Generator
3-Epideoxycholate	Generator
3b-Deoxycholate	Generator
3b-Deoxycholic acid	Generator
3beta-Deoxycholate	Generator
3Β-deoxycholate	Generator
3Β-deoxycholic acid	Generator
Isodeoxycholate	Generator
3b,12a-Dihydroxy-5b-cholanoate	Generator
3b,12a-Dihydroxy-5b-cholan-24-Oate	HMDB
3b,12a-Dihydroxy-5b-cholan-24-Oic acid	HMDB
3b,12a-Dihydroxy-5b-cholanate	HMDB
3b,12a-Dihydroxy-5b-cholanic acid	HMDB
3b,12a-Dihydroxycholanoate	HMDB
3b,12a-Dihydroxycholanoic acid	HMDB
5b-Cholanic acid-3b,12a-diol	HMDB

Chemical Formula

C₂₄H₄₀O₄

Average Molecular Weight

392.572

Monoisotopic Molecular Weight

392.292659768

IUPAC Name

(4R)-4-[(1S,2S,5S,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

Traditional Name

3-epideoxycholic acid

CAS Registry Number

570-63-8

SMILES

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

InChI Identifier

InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17+,18-,19+,20+,21+,23+,24-/m1/s1

InChI Key

KXGVEGMKQFWNSR-OFYXWCICSA-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
3-beta-hydroxysteroid
12-hydroxysteroid
Hydroxysteroid
Cyclic alcohol
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C24 bile acids, alcohols, and derivatives (LMST04010042 )

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	3.3	ALOGPS
logP	3.79	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-0.35	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	109.2 m³·mol⁻¹	ChemAxon
Polarizability	46.16 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	splash10-00os-0119000000-ff101495d4bc6a37fc83	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0006-1110390000-cc7d539ad02f4039ec09	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 (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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0009000000-862fe061e17daf909f81	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-0009000000-d2bc073ceca3e5b14c88	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02vi-3109000000-5a4bd324fa583768a2e1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-006x-0009000000-f969293bf286459bff3f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dl-0009000000-6d3e401b3a1ad3688eb2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9007000000-b74124eb1410789ddd2b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-054o-0009000000-042c286dcf0175c346a7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0adi-4369000000-386bba727c7c7b5bb692	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-8950000000-659edbcb6317b8faa9c7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-d1f986325aed82b811c5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-0009000000-22208ced9e4760090001	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ts-1049000000-7c902ce3c2dd5fb3009c	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm

Biospecimen Locations

Gallbladder
Intestine
Kidney
Liver

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Gallbladder	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
Kidney	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

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000438

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022045

KNApSAcK ID

Not Available

Chemspider ID

141062

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5427

PubChem Compound

160530

PDB ID

Not Available

ChEBI ID

88098

References

Synthesis Reference

Danielsson, Henry; Eneroth, Peter; Hellstrom, Kjell; Sjovall, Jan. Bile acids and steroids. CXXIII. Synthesis of some 3b-hydroxylated bile acids and the isolation of 3b,12a-dihydroxy-5b-cholanic acid from feces. Journal of Biological Chemistry (1962), 237 3657-9.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 3b,12a-Dihydroxy-5b-cholanoic acid (BMDB0000438)

Structure for BMDB0000438 (3b,12a-Dihydroxy-5b-cholanoic acid)