Showing metabocard for Deoxycholic acid (BMDB0000626)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:33:49 UTC
Update Date2020-05-11 20:08:56 UTC
BMDB IDBMDB0000626
Secondary Accession Numbers
  • BMDB00626
Metabolite Identification
Common NameDeoxycholic acid
DescriptionDeoxycholic 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
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3ALPHA,5ALPHA,12ALPHA)-3,12-DIHYDROXYCHOLAN-24-OIC ACIDChEBI
(3alpha,5beta,12alpha)-3,12-Dihydroxycholan-24-Oic acidChEBI
3alpha,12alpha-Dihydroxy-5beta-cholanic acidChEBI
7alpha-Deoxycholic acidChEBI
Desoxycholic acidChEBI
DesoxycholsaeureChEBI
DeoxycholateKegg
3alpha,12alpha-Dihydroxy-5beta-cholanateKegg
(3a,5a,12a)-3,12-DIHYDROXYCHOLAN-24-OateGenerator
(3a,5a,12a)-3,12-DIHYDROXYCHOLAN-24-Oic acidGenerator
(3alpha,5alpha,12alpha)-3,12-DIHYDROXYCHOLAN-24-OateGenerator
(3Α,5α,12α)-3,12-dihydroxycholan-24-OateGenerator
(3Α,5α,12α)-3,12-dihydroxycholan-24-Oic acidGenerator
(3a,5b,12a)-3,12-Dihydroxycholan-24-OateGenerator
(3a,5b,12a)-3,12-Dihydroxycholan-24-Oic acidGenerator
(3alpha,5beta,12alpha)-3,12-Dihydroxycholan-24-OateGenerator
(3Α,5β,12α)-3,12-dihydroxycholan-24-OateGenerator
(3Α,5β,12α)-3,12-dihydroxycholan-24-Oic acidGenerator
3a,12a-Dihydroxy-5b-cholanateGenerator
3a,12a-Dihydroxy-5b-cholanic acidGenerator
3Α,12α-dihydroxy-5β-cholanateGenerator
3Α,12α-dihydroxy-5β-cholanic acidGenerator
7a-DeoxycholateGenerator
7a-Deoxycholic acidGenerator
7alpha-DeoxycholateGenerator
7Α-deoxycholateGenerator
7Α-deoxycholic acidGenerator
DesoxycholateGenerator
5b-Cholanic acid-3a,12a-diolHMDB
5b-DeoxycholateHMDB
5b-Deoxycholic acidHMDB
7-DeoxycholateHMDB
7-Deoxycholic acidHMDB
CholerebicHMDB
CholorebicHMDB
DegalolHMDB
Deoxy-cholateHMDB
Deoxy-cholic acidHMDB
DeoxycholatateHMDB
Deoxycholatic acidHMDB
Acid, lagodeoxycholicHMDB
Deoxycholic acid, 5alpha isomerHMDB
Deoxycholic acid, sodium salt, 12beta-isomerHMDB
Lagodeoxycholic acidHMDB
Acid, choleicHMDB
Deoxycholic acid, 12beta isomerHMDB
Deoxycholic acid, 3beta-isomerHMDB
Deoxycholic acid, monoammonium saltHMDB
12beta-Isomer deoxycholic acidHMDB
3beta-Isomer deoxycholic acidHMDB
Acid, 5alpha-isomer deoxycholicHMDB
Acid, deoxycholicHMDB
Acid, desoxycholicHMDB
Deoxycholate, sodiumHMDB
Deoxycholic acid, 12beta-isomerHMDB
Deoxycholic acid, 5alpha-isomerHMDB
Deoxycholic acid, monopotassium saltHMDB
Deoxycholic acid, monosodium saltHMDB
5alpha-Isomer deoxycholic acidHMDB
Acid, dihydroxycholanoicHMDB
Choleic acidHMDB
Deoxycholic acid, 3beta isomerHMDB
Deoxycholic acid, disodium saltHMDB
Deoxycholic acid, magnesium (2:1) saltHMDB
Dihydroxycholanoic acidHMDB
Sodium deoxycholateHMDB
Chemical FormulaC24H40O4
Average Molecular Weight392.572
Monoisotopic Molecular Weight392.292659768
IUPAC Name(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-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,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
CAS Registry Number83-44-3
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O
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 KeyKXGVEGMKQFWNSR-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentDihydroxy 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 FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.3ALOGPS
logP3.79ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-0.35ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.2 m³·mol⁻¹ChemAxon
Polarizability46.3 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00os-0119000000-ff101495d4bc6a37fc83View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0006-1110390000-cc7d539ad02f4039ec09View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0006-0009000000-8b9c4803e9cb1d194c2eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-0009000000-cccabd9d13ac783b6e31View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0007-2009000000-d7c20760d2074c07af22View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0006-0009000000-269a5d1ed75b71c78ecbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0007-0009000000-72f1acf9f31f344daaa1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-000x-0008000900-ebb0e6a61bd8f06a21f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0002-0009000000-8078ef73008efc65c713View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-0009000000-269a5d1ed75b71c78ecbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0007-0009000000-827a9ce119d7f2f1cb5cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-0009000000-ade8ee412cabab0a5cddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0007-0009000000-827a9ce119d7f2f1cb5cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-46347f9ccba012a193b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0007-0009000000-7de3b9549dc580acb2afView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0007-0009000000-72f1acf9f31f344daaa1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0007-0009000000-fa7c4f74eaf1bb2e1f57View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-737c78b82fef7180b7acView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-0009000000-eb86d43bab0334d7cfe4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0009000000-db8bf3905980e8620f12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0009000000-6a632f1c8fbb19a314cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-4219000000-29a9a2c5d3d148fca202View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-ab9ac299290313e78fe4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-1009000000-6444232cac6b7a24dd96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9006000000-b2f4c82d34550211259cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-054o-0019000000-a4dfbb4ad2f96e8ee6dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0adl-4298000000-b6171657518bf9639cbeView in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
Biospecimen Locations
  • Erythrocyte
  • Fibroblasts
  • Intestine
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
ErythrocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000626
DrugBank IDDB03619
Phenol Explorer Compound IDNot Available
FooDB IDFDB012780
KNApSAcK IDC00030117
Chemspider ID193196
KEGG Compound IDC04483
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDeoxycholic acid
METLIN ID265
PubChem Compound222528
PDB IDNot Available
ChEBI ID28834
References
Synthesis ReferenceHe, 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 ReferencesNot 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