Bovine Metabolome Database: Showing metabocard for Deoxycholic acid (BMDB0000626)

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Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:33:49 UTC

Update Date

2020-05-11 20:08:56 UTC

BMDB ID

BMDB0000626

Secondary Accession Numbers

BMDB00626

Metabolite Identification

Common Name

Deoxycholic acid

Description

Deoxycholic acid, also known as deoxycholate or acid, deoxycholic, 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. Deoxycholic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3ALPHA,5ALPHA,12ALPHA)-3,12-DIHYDROXYCHOLAN-24-OIC ACID	ChEBI
(3alpha,5beta,12alpha)-3,12-Dihydroxycholan-24-Oic acid	ChEBI
3alpha,12alpha-Dihydroxy-5beta-cholanic acid	ChEBI
7alpha-Deoxycholic acid	ChEBI
Desoxycholic acid	ChEBI
Desoxycholsaeure	ChEBI
Deoxycholate	Kegg
3alpha,12alpha-Dihydroxy-5beta-cholanate	Kegg
(3a,5a,12a)-3,12-DIHYDROXYCHOLAN-24-Oate	Generator
(3a,5a,12a)-3,12-DIHYDROXYCHOLAN-24-Oic acid	Generator
(3alpha,5alpha,12alpha)-3,12-DIHYDROXYCHOLAN-24-Oate	Generator
(3Α,5α,12α)-3,12-dihydroxycholan-24-Oate	Generator
(3Α,5α,12α)-3,12-dihydroxycholan-24-Oic acid	Generator
(3a,5b,12a)-3,12-Dihydroxycholan-24-Oate	Generator
(3a,5b,12a)-3,12-Dihydroxycholan-24-Oic acid	Generator
(3alpha,5beta,12alpha)-3,12-Dihydroxycholan-24-Oate	Generator
(3Α,5β,12α)-3,12-dihydroxycholan-24-Oate	Generator
(3Α,5β,12α)-3,12-dihydroxycholan-24-Oic acid	Generator
3a,12a-Dihydroxy-5b-cholanate	Generator
3a,12a-Dihydroxy-5b-cholanic acid	Generator
3Α,12α-dihydroxy-5β-cholanate	Generator
3Α,12α-dihydroxy-5β-cholanic acid	Generator
7a-Deoxycholate	Generator
7a-Deoxycholic acid	Generator
7alpha-Deoxycholate	Generator
7Α-deoxycholate	Generator
7Α-deoxycholic acid	Generator
Desoxycholate	Generator
5b-Cholanic acid-3a,12a-diol	HMDB
5b-Deoxycholate	HMDB
5b-Deoxycholic acid	HMDB
7-Deoxycholate	HMDB
7-Deoxycholic acid	HMDB
Cholerebic	HMDB
Cholorebic	HMDB
Degalol	HMDB
Deoxy-cholate	HMDB
Deoxy-cholic acid	HMDB
Deoxycholatate	HMDB
Deoxycholatic acid	HMDB
Acid, lagodeoxycholic	HMDB
Deoxycholic acid, 5alpha isomer	HMDB
Deoxycholic acid, sodium salt, 12beta-isomer	HMDB
Lagodeoxycholic acid	HMDB
Acid, choleic	HMDB
Deoxycholic acid, 12beta isomer	HMDB
Deoxycholic acid, 3beta-isomer	HMDB
Deoxycholic acid, monoammonium salt	HMDB
12beta-Isomer deoxycholic acid	HMDB
3beta-Isomer deoxycholic acid	HMDB
Acid, 5alpha-isomer deoxycholic	HMDB
Acid, deoxycholic	HMDB
Acid, desoxycholic	HMDB
Deoxycholate, sodium	HMDB
Deoxycholic acid, 12beta-isomer	HMDB
Deoxycholic acid, 5alpha-isomer	HMDB
Deoxycholic acid, monopotassium salt	HMDB
Deoxycholic acid, monosodium salt	HMDB
5alpha-Isomer deoxycholic acid	HMDB
Acid, dihydroxycholanoic	HMDB
Choleic acid	HMDB
Deoxycholic acid, 3beta isomer	HMDB
Deoxycholic acid, disodium salt	HMDB
Deoxycholic acid, magnesium (2:1) salt	HMDB
Dihydroxycholanoic acid	HMDB
Sodium deoxycholate	HMDB

Chemical Formula

C₂₄H₄₀O₄

Average Molecular Weight

392.572

Monoisotopic Molecular Weight

392.292659768

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

83-44-3

SMILES

Not Available

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-LLQZFEROSA-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-alpha-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

bile acid (CHEBI:28834 )
dihydroxy-5beta-cholanic acid (CHEBI:28834 )
C24 bile acids, alcohols, and derivatives (C04483 )
Cholane and derivatives (C04483 )
C24 bile acids, alcohols, and derivatives (LMST04010040 )

Ontology

Status

Detected 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

Not Available

Spectra

Spectrum Type	Description	Splash Key

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm

Biospecimen Locations

Erythrocyte
Fibroblasts
Intestine
Liver

Pathways

Name	SMPDB/Pathwhiz	KEGG
Bile Acid Biosynthesis		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Erythrocyte	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	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000626

DrugBank ID

DB03619

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

Deoxycholic acid

METLIN ID

265

PubChem Compound

222528

PDB ID

Not Available

ChEBI ID

28834

References

Synthesis Reference

He, Zhiquan. in-situ generation of deoxycholic acid by poultry for Chinese medicine. Faming Zhuanli Shenqing Gongkai Shuomingshu (1993), 3 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Bile acid receptor

General function:: Involved in sequence-specific DNA binding
Specific function:: Ligand-activated transcription factor. Receptor for bile acids (BAs) such as chenodeoxycholic acid (CDCA), lithocholic acid, deoxycholic acid (DCA) and allocholic acid (ACA). Plays a essential role in BA homeostasis through the regulation of genes involved in BA synthesis, conjugation and enterohepatic circulation. Also regulates lipid and glucose homeostasis and is involved innate immune response. The FXR-RXR heterodimer binds predominantly to farnesoid X receptor response elements (FXREs) containing two inverted repeats of the consensus sequence 5'-AGGTCA-3' in which the monomers are spaced by 1 nucleotide (IR-1) but also to tandem repeat DR1 sites with lower affinity, and can be activated by either FXR or RXR-specific ligands. It is proposed that monomeric nuclear receptors such as NR5A2/LRH-1 bound to coregulatory nuclear responsive element (NRE) halfsites located in close proximity to FXREs modulate transcriptional activity. In the liver activates transcription of the corepressor NR0B2 thereby indirectly inhibiting CYP7A1 and CYP8B1 (involved in BA synthesis) implicating at least in part histone demethylase KDM1A resulting in epigenomic repression, and SLC10A1/NTCP (involved in hepatic uptake of conjugated BAs). Activates transcription of the repressor MAFG (involved in regulation of BA synthesis). Activates transcription of SLC27A5/BACS and BAAT (involved in BA conjugation), ABCB11/BSEP (involved in bile salt export) by directly recruiting histone methyltransferase CARM1, and ABCC2/MRP2 (involved in secretion of conjugated BAs) and ABCB4 (involved in secretion of phosphatidylcholine in the small intestine). Activates transcription of SLC27A5/BACS and BAAT (involved in BA conjugation), ABCB11/BSEP (involved in bile salt export) by directly recruiting histone methyltransferase CARM1, and ABCC2/MRP2 (involved in secretion of conjugated BAs) and ABCB4 (involved in secretion of phosphatidylcholine in the small intestine). In the intestine activates FGF19 expression and secretion leading to hepatic CYP7A1 repression. The function also involves the coordinated induction of hepatic KLB/beta-klotho expression. Regulates transcription of liver UGT2B4 and SULT2A1 involved in BA detoxification; binding to the UGT2B4 promoter seems to imply a monomeric transactivation independent of RXRA. Modulates lipid homeostasis by activating liver NR0B2/SHP-mediated repression of SREBF1 (involved in de novo lipogenesis), expression of PLTP (involved in HDL formation), SCARB1 (involved in HDL hepatic uptake), APOE, APOC1, APOC4, PPARA (involved in beta-oxidation of fatty acids), VLDLR and SDC1 (involved in the hepatic uptake of LDL and IDL remnants), and inhibiting expression of MTTP (involved in VLDL assembly). Increases expression of APOC2 (promoting lipoprotein lipase activity implicated in triglyceride clearance). Transrepresses APOA1 involving a monomeric competition with NR2A1 for binding to a DR1 element. Also reduces triglyceride clearance by inhibiting expression of ANGPTL3 and APOC3 (both involved in inhibition of lipoprotein lipase). Involved in glucose homeostasis by modulating hepatic gluconeogenesis through activation of NR0B2/SHP-mediated repression of respective genes. Modulates glycogen synthesis (inducing phosphorylation of glycogen synthase kinase-3). Modulates glucose-stimulated insulin secretion and is involved in insulin resistance. Involved in intestinal innate immunity. Plays a role in protecting the distal small intestine against bacterial overgrowth and preservation of the epithelial barrier. Down-regulates inflammatory cytokine expression in several types of immune cells including macrophages and mononuclear cells. Mediates trans-repression of TLR4-induced cytokine expression; the function seems to require its sumoylation and prevents N-CoR nuclear receptor corepressor clearance from target genes such as IL1B and NOS2. Involved in the TLR9-mediated protective mechanism in intestinal inflammation. Plays an anti-inflammatory role in liver inflammation; proposed to inhibit proinflammatory (but not antiapoptotic) NF-kappa-B signaling.
Gene Name:: NR1H4
Uniprot ID:: Q3SZL0
Molecular weight:: 55460.0

Showing metabocard for Deoxycholic acid (BMDB0000626)

Structure for BMDB0000626 (Deoxycholic acid)

Enzymes