Back to Compounds

Showing Compound cholate (FDB030724)

Record Information
Version1.0
Creation date2015-05-07 19:55:49 UTC
Update date2019-11-26 03:21:52 UTC
Primary IDFDB030724
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namecholate
DescriptionCholic acid, also known as 3a,7a,12a-trihydroxy-5b-cholanate or cholate, belongs to trihydroxy bile acids, alcohols and derivatives class of compounds. Those are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. Thus, cholic acid is considered to be a bile acid lipid molecule. Cholic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Cholic acid can be found in a number of food items such as cocoa bean, walnut, garden rhubarb, and carob, which makes cholic acid a potential biomarker for the consumption of these food products. Cholic acid can be found primarily in bile, blood, feces, and urine, as well as throughout all human tissues. Cholic acid exists in all living organisms, ranging from bacteria to humans. In humans, cholic acid is involved in few metabolic pathways, which include bile acid biosynthesis, cerebrotendinous xanthomatosis (CTX), congenital bile acid synthesis defect type II, and congenital bile acid synthesis defect type III. Cholic acid is also involved in few metabolic disorders, which include 27-hydroxylase deficiency, familial hypercholanemia (FHCA), and zellweger syndrome. Moreover, cholic acid is found to be associated with biliary atresia, cirrhosis, cystic fibrosis, and primary biliary cirrhosis. Cholic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound.
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
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)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
InChI KeyBHQCQFFYRZLCQQ-OELDTZBJSA-N
Isomeric SMILES[H][C@@](C)(CCC(O)=O)[C@@]1([H])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])C[C@]([H])(O)[C@]12C
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Indirect biological role:

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
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 IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference