Bovine Metabolome Database: Showing metabocard for 3b,7a-Dihydroxy-5b-cholanoic acid (BMDB0000361)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:29:18 UTC

Update Date

2020-05-11 20:20:31 UTC

BMDB ID

BMDB0000361

Secondary Accession Numbers

BMDB00361

Metabolite Identification

Common Name

3b,7a-Dihydroxy-5b-cholanoic acid

Description

3b,7a-Dihydroxy-5b-cholanoic acid, also known as 3-epi-chenodeoxycholic acid or (3b,5b,7a)-3,7-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. Based on a literature review a significant number of articles have been published on 3b,7a-Dihydroxy-5b-cholanoic acid.

Structure

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

Synonyms

Value	Source
(3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-Oic acid	ChEBI
3-Epi-chenodeoxycholic acid	ChEBI
3-Epichenodeoxycholic acid	ChEBI
3beta,7alpha-Dihydroxy-5beta-cholanic acid	ChEBI
3beta-Chenodeoxycholic acid	ChEBI
Isochenodeoxycholic acid	ChEBI
(3b,5b,7a)-3,7-Dihydroxycholan-24-Oate	Generator
(3b,5b,7a)-3,7-Dihydroxycholan-24-Oic acid	Generator
(3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-Oate	Generator
(3Β,5β,7α)-3,7-dihydroxycholan-24-Oate	Generator
(3Β,5β,7α)-3,7-dihydroxycholan-24-Oic acid	Generator
3-Epi-chenodeoxycholate	Generator
3-Epichenodeoxycholate	Generator
3b,7a-Dihydroxy-5b-cholanate	Generator
3b,7a-Dihydroxy-5b-cholanic acid	Generator
3beta,7alpha-Dihydroxy-5beta-cholanate	Generator
3Β,7α-dihydroxy-5β-cholanate	Generator
3Β,7α-dihydroxy-5β-cholanic acid	Generator
3b-Chenodeoxycholate	Generator
3b-Chenodeoxycholic acid	Generator
3beta-Chenodeoxycholate	Generator
3Β-chenodeoxycholate	Generator
3Β-chenodeoxycholic acid	Generator
Isochenodeoxycholate	Generator
3b,7a-Dihydroxy-5b-cholanoate	Generator
3b,7a-Dihydroxy-5b-cholan-24-Oate	HMDB
3b,7a-Dihydroxy-5b-cholan-24-Oic acid	HMDB

Chemical Formula

C₂₄H₄₀O₄

Average Molecular Weight

392.572

Monoisotopic Molecular Weight

392.292659768

IUPAC Name

(4R)-4-[(1S,2S,5S,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2S,5S,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

CAS Registry Number

566-24-5

SMILES

[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@@H](O)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-JGFDLHJZSA-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
Hydroxysteroid
3-beta-hydroxysteroid
7-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

cholanoid (CHEBI:81255 )
C24 bile acids, alcohols, and derivatives (LMST04010034 )

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	46.23 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-0529000000-3b28c649fc51c7806ad3	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0006-1110390000-7a6c62344d1371b74081	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-caf73ba5a49d006bb35c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-0009000000-19e20147b99f0203beea	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02di-1219000000-2712784370392aae8dfe	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-9007000000-941ad38857c04e2f5622	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-054o-0009000000-4e0986447d05e9362fad	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-3229000000-0ec43eb64212ba6669ce	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-3930000000-0af26f4ca58ef37524aa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-9ec5a4bbbe3c1396f290	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-0009000000-94b82bd5679a84a4db10	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052p-2009000000-302f7e60ce3076bc9db1	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

HMDB0000361

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021981

KNApSAcK ID

Not Available

Chemspider ID

144359

KEGG Compound ID

C17660

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5350

PubChem Compound

164673

PDB ID

Not Available

ChEBI ID

88102

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,7a-Dihydroxy-5b-cholanoic acid (BMDB0000361)

Structure for BMDB0000361 (3b,7a-Dihydroxy-5b-cholanoic acid)