Bovine Metabolome Database: Showing metabocard for Chenodeoxycholic acid (BMDB0000518)

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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 22:32:02 UTC

Update Date

2020-05-11 20:00:42 UTC

BMDB ID

BMDB0000518

Secondary Accession Numbers

BMDB00518

Metabolite Identification

Common Name

Chenodeoxycholic acid

Description

Chenodeoxycholic acid, also known as anthropodeoxycholate or chenix, 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. Chenodeoxycholic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3alpha,7alpha-Dihydroxy-5beta-cholanic acid	ChEBI
7alpha-Hydroxylithocholic acid	ChEBI
Anthropodeoxycholic acid	ChEBI
Anthropodesoxycholic acid	ChEBI
CDCA	ChEBI
Chenic acid	ChEBI
Chenix	ChEBI
Chenodiol	ChEBI
Gallodesoxycholic acid	ChEBI
3a,7a-Dihydroxy-5b-cholanate	Generator
3a,7a-Dihydroxy-5b-cholanic acid	Generator
3alpha,7alpha-Dihydroxy-5beta-cholanate	Generator
3Α,7α-dihydroxy-5β-cholanate	Generator
3Α,7α-dihydroxy-5β-cholanic acid	Generator
7a-Hydroxylithocholate	Generator
7a-Hydroxylithocholic acid	Generator
7alpha-Hydroxylithocholate	Generator
7Α-hydroxylithocholate	Generator
7Α-hydroxylithocholic acid	Generator
Anthropodeoxycholate	Generator
Anthropodesoxycholate	Generator
Chenate	Generator
Gallodesoxycholate	Generator
Chenodeoxycholate	Generator
(+)-Chenodeoxycholate	HMDB
(+)-Chenodeoxycholic acid	HMDB
(3a,5b,7a)-3,7-Dihydroxy-cholan-24-Oate	HMDB
(3a,5b,7a)-3,7-Dihydroxy-cholan-24-Oic acid	HMDB
3a,7a-Dihydroxy-5b,14a,17b-cholanate	HMDB
3a,7a-Dihydroxy-5b,14a,17b-cholanic acid	HMDB
3a,7a-Dihydroxy-5b-cholan-24-Oate	HMDB
3a,7a-Dihydroxy-5b-cholan-24-Oic acid	HMDB
7a-Hydroxy-desoxycholsaeure	HMDB
Chenodesoxycholsaeure	HMDB
Acid, chenique	HMDB
Chenofalk	HMDB
Chenophalk	HMDB
Acid, chenodeoxycholic	HMDB
Chenodeoxycholate, sodium	HMDB
Quenocol	HMDB
Solvay brand OF chenodeoxycholic acid	HMDB
Antigen brand OF chenodeoxycholic acid	HMDB
Falk brand OF chenodeoxycholic acid	HMDB
Quenobilan	HMDB
Sodium chenodeoxycholate	HMDB
Tramedico brand OF chenodeoxycholic acid	HMDB
Zambon brand OF chenodeoxycholic acid	HMDB
Acid, chenic	HMDB
Acid, gallodesoxycholic	HMDB
Chenique acid	HMDB
Estedi brand OF chenodeoxycholic acid	HMDB
Henohol	HMDB

Chemical Formula

C₂₄H₄₀O₄

Average Molecular Weight

392.572

Monoisotopic Molecular Weight

392.292659768

IUPAC Name

(4R)-4-[(1S,2S,5R,7S,9R,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,9R,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

474-25-9

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-BSWAIDMHSA-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-alpha-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

bile acid (CHEBI:16755 )
dihydroxy-5beta-cholanic acid (CHEBI:16755 )
C24 bile acids, alcohols, and derivatives (C02528 )
Cholane and derivatives (C02528 )
C24 bile acids, alcohols, and derivatives (LMST04010032 )

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	165 - 167 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0899 mg/mL	Not Available
LogP	4.15	SANGSTER (1993)

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	46.35 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
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0a6u-3920000000-ce93b24c6e2568b6087d	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a6u-3920000000-ce93b24c6e2568b6087d	View in MoNA
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	splash10-0006-1110390000-7a6c62344d1371b74081	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 (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 - Quattro_QQQ 10V, N/A (Annotated)	splash10-0a4i-0009000000-82ed6dc62b49ac0340e6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-01pa-2930000000-64edc819ad56b842cdba	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-053r-6900000000-c97325e1ca9bcff75af1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0002-0009000000-ad2d2440db7f3f1c8a2e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0009000000-2df562379077bf0f4b2a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0009000000-ff13f6ad8405e3969b6c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0009000000-1af3ba6ee17285da06a2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-5409557fb9a76a8a8e74	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0009000000-c77d97d0dfe48497b263	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0006-0009000000-d38671ccaaa16ac6d1f1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0596-0529000000-1ed436cc96fa78f90b88	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-25ba2afe78d7d8070765	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0019000000-c31d129de7de9df05167	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0009000000-fc161813afdb6d319d8d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0009000000-ee319e0cbd9987920deb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-858f2baceacfba406468	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
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm

Biospecimen Locations

Fibroblasts
Liver

Pathways

Name	SMPDB/Pathwhiz	KEGG
Bile Acid Biosynthesis		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Fibroblasts	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

HMDB0000518

DrugBank ID

DB06777

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022087

KNApSAcK ID

Not Available

Chemspider ID

9728

KEGG Compound ID

C02528

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chenodiol

METLIN ID

207

PubChem Compound

10133

PDB ID

Not Available

ChEBI ID

16755

References

Synthesis Reference

Sato, Yoshio; Ikekawa, Nobuo. Preparation of chenodeoxycholic acid. Journal of Organic Chemistry (1959), 24 1367-8.

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 Chenodeoxycholic acid (BMDB0000518)

Structure for BMDB0000518 (Chenodeoxycholic acid)

Enzymes