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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 03:42:34 UTC
Update Date2021-10-01 19:42:17 UTC
HMDB IDHMDB0249206
Secondary Accession NumbersNone
Metabolite Identification
Common NameBile acid
DescriptionAllocholic acid, also known as allocholate, 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. Based on a literature review very few articles have been published on Allocholic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Bile acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Bile acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
AllocholateGenerator
7-Epicholic acidMeSH
Ursocholic acidMeSH
3 alpha,7 beta,12 alpha-Trihydroxy-5 beta-cholan-24-Oic acidMeSH
Chemical FormulaC24H40O5
Average Molecular Weight408.5714
Monoisotopic Molecular Weight408.28757439
IUPAC Name4-{5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanoic acid
Traditional Name4-{5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanoic acid
CAS Registry NumberNot Available
SMILES
CC(CCC(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C
InChI Identifier
InChI=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
Chemical Taxonomy
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
  • 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 DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP10(2.26) g/LALOGPS
logP10(2.48) g/LChemAxon
logS10(-3.7) g/LALOGPS
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
Polarizability47.34 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Bile acidCC(CCC(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C3345.2Standard polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bile acidCC(CCC(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C2682.6Standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bile acidCC(CCC(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C3599.5Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Bile acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-0439000000-4e43231560df6c61b96d2021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bile acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bile acid 10V, Positive-QTOFsplash10-00dl-0009100000-915584a506714c4702702016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bile acid 20V, Positive-QTOFsplash10-00dl-0009000000-f970a088fc3d9cdb8fe62016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bile acid 40V, Positive-QTOFsplash10-017j-3109000000-bb054743c390ef2660442016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bile acid 10V, Negative-QTOFsplash10-0a4i-0008900000-ed202aebd950e99a78522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bile acid 20V, Negative-QTOFsplash10-0a4r-1009300000-db2a4b9107b891a8ef3a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bile acid 40V, Negative-QTOFsplash10-0a4i-9006000000-87df039839010127a1a02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bile acid 10V, Positive-QTOFsplash10-0a4l-0017900000-ea8355c2341f46a54b682021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bile acid 20V, Positive-QTOFsplash10-059i-3049200000-1edfdcecdef809ead28f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bile acid 40V, Positive-QTOFsplash10-0a6r-9620000000-0a8ca5b022edfe923d952021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bile acid 10V, Negative-QTOFsplash10-0a4i-0000900000-ec1d9319a9eaf1f2aba62021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bile acid 20V, Negative-QTOFsplash10-0a4i-0002900000-3a80230497d8bf24985f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bile acid 40V, Negative-QTOFsplash10-0a4i-1019400000-5fd668afb69bd0558f6d2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011602
KNApSAcK IDC00054052
Chemspider ID297
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound303
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Only showing the first 10 proteins. There are 53 proteins in total.

Enzymes

General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Oxidizes the CoA esters of the bile acid intermediates di- and tri-hydroxycholestanoic acids.
Gene Name:
ACOX2
Uniprot ID:
Q99424
Molecular weight:
76826.14
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.
Gene Name:
SULT2A1
Uniprot ID:
Q06520
Molecular weight:
33779.57
General function:
Involved in oxidoreductase activity
Specific function:
Functions in mitochondrial tRNA maturation. Part of mitochondrial ribonuclease P, an enzyme composed of MRPP1/TRMT10C, MRPP2/HSD17B10 and MRPP3/KIAA0391, which cleaves tRNA molecules in their 5'-ends. By interacting with intracellular amyloid-beta, it may contribute to the neuronal dysfunction associated with Alzheimer disease (AD).
Gene Name:
HSD17B10
Uniprot ID:
Q99714
Molecular weight:
25983.695
General function:
Involved in oxidoreductase activity
Specific function:
Mediates in vitro the transfer of all common phospholipids, cholesterol and gangliosides between membranes. May play a role in regulating steroidogenesis.
Gene Name:
SCP2
Uniprot ID:
P22307
Molecular weight:
34974.505
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:
UGT2B28
Uniprot ID:
Q9BY64
Molecular weight:
38742.9
General function:
Involved in oxidoreductase activity
Specific function:
Bifunctional enzyme acting on the peroxisomal beta-oxidation pathway for fatty acids. Catalyzes the formation of 3-ketoacyl-CoA intermediates from both straight-chain and 2-methyl-branched-chain fatty acids.
Gene Name:
HSD17B4
Uniprot ID:
P51659
Molecular weight:
79685.715
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular weight:
60720.15
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:
UGT1A3
Uniprot ID:
P35503
Molecular weight:
60337.835
General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes a rate-limiting step in cholesterol catabolism and bile acid biosynthesis by introducing a hydrophilic moiety at position 7 of cholesterol. Important for cholesterol homeostasis.
Gene Name:
CYP7A1
Uniprot ID:
P22680
Molecular weight:
57660.155

Transporters

General function:
Involved in bile acid:sodium symporter activity
Specific function:
The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presence of sodium.
Gene Name:
SLC10A1
Uniprot ID:
Q14973
Molecular weight:
38118.64

Only showing the first 10 proteins. There are 53 proteins in total.