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Showing Compound Cholic acid (FDB012810)

Record Information
Version1.0
Creation date2010-04-08 22:10:22 UTC
Update date2019-11-26 03:07:39 UTC
Primary IDFDB012810
Secondary Accession Numbers
  • FDB011602
Chemical Information
FooDB NameCholic acid
DescriptionEmulsifying agent in foods A major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. ; Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. ; Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. ; Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487, 16037564, 12576301, 11907135); Cholic acid is a bile acid, a white crystalline substance insoluble in water (soluble in alcohol and acetic acid), with a melting point of 200-201 °C. Salts of cholic acid are called cholates. Cholic acid, along with chenodeoxycholic acid, is one of two major bile acids produced by the liver where it is synthesized from cholesterol. Of the two major bile acids, cholate derivatives represent approximately eighty percent of all bile acids. These derivatives are made from cholyl-CoA which forms a conjugate with either glycine, or taurine, yielding glycocholic and taurocholic acid respectively.
CAS Number81-25-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-Oic acidChEBI
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanateChEBI
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acidChEBI
CholsaeureChEBI
CholateKegg
(3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-OateGenerator
(3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-Oic acidGenerator
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-OateGenerator
(3Α,5β,7α,12α)-3,7,12-trihydroxycholan-24-OateGenerator
(3Α,5β,7α,12α)-3,7,12-trihydroxycholan-24-Oic acidGenerator
3a,7a,12a-Trihydroxy-5b-cholanateGenerator
3a,7a,12a-Trihydroxy-5b-cholanic acidGenerator
3Α,7α,12α-trihydroxy-5β-cholanateGenerator
3Α,7α,12α-trihydroxy-5β-cholanic acidGenerator
AllocholateHMDB
17b-[1-Methyl-3-carboxypropyl]etiocholane-3a,7a,12a-triolHMDB
3a,7a,12a-Trihydroxy-5b-cholan-24-OateHMDB
3a,7a,12a-Trihydroxy-5b-cholan-24-Oic acidHMDB
3a,7a,12a-Trihydroxy-5b-cholanoateHMDB
3a,7a,12a-Trihydroxy-5b-cholanoic acidHMDB
3a,7a,12a-Trihydroxy-b-cholanateHMDB
3a,7a,12a-Trihydroxy-b-cholanic acidHMDB
3a,7a,12a-Trihydroxy-beta-cholanateHMDB
3a,7a,12a-Trihydroxy-beta-cholanic acidHMDB
3a,7a,12a-TrihydroxycholanateHMDB
3a,7a,12a-Trihydroxycholanic acidHMDB
5b-Cholanic acid-3a,7a,12a-triolHMDB
5b-CholateHMDB
5b-Cholic acidHMDB
CholalateHMDB
Cholalic acidHMDB
CholalinHMDB
ColalinHMDB
Acid, cholicHMDB
Cholic acidGenerator
(3α,5β,7α,12α)-3,7,12-trihydroxycholan-24-OateGenerator
(3α,5β,7α,12α)-3,7,12-trihydroxycholan-24-Oic acidGenerator
3-&alpha,7-&alpha,12-&alpha-trihydroxy-5-&beta-cholanatebiospider
3,7,12-Trihydroxy-cholan-24-oic acidbiospider
3,7,12-Trihydroxycholanic acidbiospider
3a,7a,12a-Trihydroxy-5b-cholan-24-oatebiospider
3a,7a,12a-Trihydroxy-5b-cholan-24-oic acidbiospider
3alpha,7alpha-Dihydroxy-5beta-cholanic acidbiospider
3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-24-oic acidbiospider
3alpha,7alpha,12alpha-trihydroxy-5beta-cholanic acidbiospider
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanoic acidbiospider
3alpha,7alpha,12alpha-Trihydroxy-beta-cholanic acidbiospider
3alpha,7alpha,12alpha-Trihydroxycholanic acidbiospider
3α,7α,12α-trihydroxy-5β-cholanateGenerator
3α,7α,12α-trihydroxy-5β-cholanic acidGenerator
5beta-Cholan-24-oic acid, 3alpha,7alpha,12alpha-trihydroxy-biospider
5beta-Cholanic acid-3alpha,7alpha-diolbiospider
Chenodiolbiospider
Cholagitdb_source
Cholan-24-oic acidbiospider
Cholanic acidbiospider
Cholic acid, 5beta-biospider
Hypocholatedb_source
NSC 6135db_source
Predicted Properties
PropertyValueSource
logP2.48ChemAxon
pKa (Strongest Acidic)4.48ChemAxon
pKa (Strongest Basic)-0.16ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity110.79 m³·mol⁻¹ChemAxon
Polarizability47.05 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC24H40O5
IUPAC name(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
InChI IdentifierInChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)
InChI KeyBHQCQFFYRZLCQQ-UHFFFAOYSA-N
Isomeric SMILESCC(CCC(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C
Average Molecular Weight408.5714
Monoisotopic Molecular Weight408.28757439
Classification
Description Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTrihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Trihydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Polyol
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 70.55%; H 9.87%; O 19.58%DFC
Melting PointMp 197° (anhyd.)DFC
Boiling PointNot Available
Experimental Water Solubility0.175 mg/mL at 20 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP2.02RODA,A ET AL. (1990)
Experimental pKapKa1 4.98 (20°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +37 (EtOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0596-9642000000-e425981b8a0ac72ea6ee2014-09-20View Spectrum
GC-MScholate, non-derivatized, GC-MS Spectrumsplash10-0fk9-5796000000-2876080f3fa17fb96370Spectrum
GC-MScholate, non-derivatized, GC-MS Spectrumsplash10-0fk9-5796000000-2876080f3fa17fb96370Spectrum
Predicted GC-MScholate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dl-0439000000-4e43231560df6c61b96dSpectrum
Predicted GC-MScholate, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-1100049000-86faaffe1dc0eadf9e75Spectrum
Predicted GC-MScholate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScholate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScholate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScholate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScholate, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScholate, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScholate, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScholate, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScholate, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScholate, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScholate, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScholate, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScholate, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScholate, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScholate, TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScholate, TMS_3_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScholate, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScholate, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScholate, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScholate, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScholate, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0000900000-806d3b03c76019afbf7d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0000900000-4edb603ca5534669120e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0000900000-4a76e64b2f0411d0b7012017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0001900000-41aa3a7cb25fcf5490462017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0057900000-790a3808fa512d5d16872017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0010900000-e6bedfc253363160a37e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0030900000-da4a7bfccbaf1e42171c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0020900000-772055897702843a1d502017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0021900000-0405fe63d70d3a88bf6f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0aou-3844900000-cb3c2aba1b9a297856162017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0007-0019000000-fb9a5b5952cf65eb79882017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0001900000-9583bd9c6c0d2b069b682017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-1027900000-31f3cf065ad48561c0a22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0000900000-b0504ee652d51a711f3a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0000900000-18dd8b6be45775ec83c22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0007-0019000000-285d3d0d87f5471b419a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0007-0019000000-0fcb0f6819b05ab63c122017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0000900000-b0504ee652d51a711f3a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0000900000-18dd8b6be45775ec83c22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0007-0019000000-285d3d0d87f5471b419a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0007-0019000000-0fcb0f6819b05ab63c122017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-6fe7340aea27993f6ecb2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a4i-0001900000-9e5ac05d22599c16d77a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-a58dbdca74695c9c40e12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-1c1c35b35f948ca539432021-09-20View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 50.18 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
ChemSpider ID192176
ChEMBL IDCHEMBL205596
KEGG Compound IDC00695
Pubchem Compound ID221493
Pubchem Substance IDNot Available
ChEBI ID16359
Phenol-Explorer IDNot Available
DrugBank IDDB02659
HMDB IDHMDB00619
CRC / DFC (Dictionary of Food Compounds) IDHLJ16-X:HLJ07-V
EAFUS ID628
Dr. Duke IDNot Available
BIGG ID35720
KNApSAcK IDNot Available
HET IDCHD
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCholic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Liver carboxylesterase 1CES1P23141
Acyl-coenzyme A thioesterase 8ACOT8O14734
FerrochelataseDKFZp686P18130Q7KZA3
Cytochrome c oxidase subunit 7A1, mitochondrialCOX7A1P24310
Bile acyl-CoA synthetaseSLC27A5Q9Y2P5
Cytochrome c oxidase subunit 6A2, mitochondrialCOX6A2Q02221
Cytochrome c oxidase subunit 7B, mitochondrialCOX7BP24311
Cytochrome c oxidase subunit 7C, mitochondrialCOX7CP15954
Cytochrome c oxidase subunit 5B, mitochondrialCOX5BP10606
Cytochrome c oxidase subunit 6B1COX6B1P14854
Cytochrome c oxidase subunit 4 isoform 1, mitochondrialCOX4I1P13073
Cytochrome c oxidase subunit 8A, mitochondrialCOX8AP10176
Cytochrome c oxidase subunit 6CCOX6CP09669
Cytochrome c oxidase subunit 3MT-CO3P00414
Pathways
NameSMPDB LinkKEGG Link
Bile Acid BiosynthesisSMP00035 map00120
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference