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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:41 UTC
Update Date2022-03-07 02:49:13 UTC
HMDB IDHMDB0002195
Secondary Accession Numbers
  • HMDB02195
Metabolite Identification
Common NameVaranic acid
DescriptionVaranic acid is a bile acid that will accumulate in patients with deficiencies in the peroxisomal d-bifunctional protein. The final steps in bile acid biosynthesis take place in peroxisomes and involve oxidative cleavage of the side chain of C27-5beta-cholestanoic acids leading to the formation of the primary bile acids cholic acid and chenodeoxycholic acid. The enoyl-CoA hydratase and beta-hydroxy acyl-CoA dehydrogenase reactions involved in the chain shortening of C27-5beta-cholestanoic acids are catalyzed by peroxisomal d-bifunctional protein. (PMID: 9831634 ).
Structure
Data?1582752235
Synonyms
ValueSource
VaranateGenerator
3a,7a,12a,24-Tetrahydroxy-5b-cholestan-26-OateHMDB
3a,7a,12a,24-Tetrahydroxy-5b-cholestan-26-Oic acidHMDB
3a,7a,12a,24-Tetrahydroxy-5b-cholestanoateHMDB
3a,7a,12a,24-Tetrahydroxy-5b-cholestanoic acidHMDB
3alpha,7alpha,12alpha, 24-Tetrahydroxy-5beta-cholest-26-OateHMDB
3alpha,7alpha,12alpha, 24-Tetrahydroxy-5beta-cholest-26-Oic acidHMDB
BaranateHMDB
Baranic acidHMDB
(2R,3R,6R)-2,3-Dihydroxy-6-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanoateGenerator, HMDB
Chemical FormulaC26H44O5
Average Molecular Weight436.6246
Monoisotopic Molecular Weight436.318874518
IUPAC Name(2R,3R,6R)-2,3-dihydroxy-6-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanoic acid
Traditional Namevaranic acid
CAS Registry Number1061-64-9
SMILES
[H][C@@]12CC[C@H]([C@H](C)CC[C@@H](O)[C@@H](O)C(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C26H44O5/c1-15(4-9-22(28)23(29)24(30)31)19-7-8-20-18-6-5-16-14-17(27)10-12-25(16,2)21(18)11-13-26(19,20)3/h15-23,27-29H,4-14H2,1-3H3,(H,30,31)/t15-,16-,17-,18+,19-,20+,21+,22-,23-,25+,26-/m1/s1
InChI KeyNRDKNLGDNLHWHG-IYELHLJQSA-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
  • Cholesterol-skeleton
  • Cholestane-skeleton
  • 25-hydroxysteroid
  • Trihydroxy bile acid, alcohol, or derivatives
  • 24-hydroxysteroid
  • Steroid acid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Hydroxy fatty acid
  • Monosaccharide
  • Alpha-hydroxy acid
  • Fatty acid
  • Fatty acyl
  • Hydroxy acid
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0081 g/LALOGPS
logP3.41ALOGPS
logP3.97ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)4.05ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity119.74 m³·mol⁻¹ChemAxon
Polarizability51.21 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-240.41330932474
DeepCCS[M+Na]+214.61330932474
AllCCS[M+H]+211.532859911
AllCCS[M+H-H2O]+209.732859911
AllCCS[M+NH4]+213.232859911
AllCCS[M+Na]+213.632859911
AllCCS[M-H]-206.332859911
AllCCS[M+Na-2H]-208.332859911
AllCCS[M+HCOO]-210.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Varanic acid[H][C@@]12CC[C@H]([C@H](C)CC[C@@H](O)[C@@H](O)C(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C3472.1Standard polar33892256
Varanic acid[H][C@@]12CC[C@H]([C@H](C)CC[C@@H](O)[C@@H](O)C(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C3670.1Standard non polar33892256
Varanic acid[H][C@@]12CC[C@H]([C@H](C)CC[C@@H](O)[C@@H](O)C(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C3790.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Varanic acid,1TMS,isomer #1C[C@H](CC[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3773.9Semi standard non polar33892256
Varanic acid,1TMS,isomer #2C[C@H](CC[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3789.1Semi standard non polar33892256
Varanic acid,1TMS,isomer #3C[C@H](CC[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3652.4Semi standard non polar33892256
Varanic acid,1TMS,isomer #4C[C@H](CC[C@@H](O)[C@@H](O)C(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3768.6Semi standard non polar33892256
Varanic acid,2TMS,isomer #1C[C@H](CC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3775.0Semi standard non polar33892256
Varanic acid,2TMS,isomer #2C[C@H](CC[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3657.0Semi standard non polar33892256
Varanic acid,2TMS,isomer #3C[C@H](CC[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3761.1Semi standard non polar33892256
Varanic acid,2TMS,isomer #4C[C@H](CC[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3697.0Semi standard non polar33892256
Varanic acid,2TMS,isomer #5C[C@H](CC[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3770.1Semi standard non polar33892256
Varanic acid,2TMS,isomer #6C[C@H](CC[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3659.8Semi standard non polar33892256
Varanic acid,3TMS,isomer #1C[C@H](CC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3723.4Semi standard non polar33892256
Varanic acid,3TMS,isomer #2C[C@H](CC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3753.0Semi standard non polar33892256
Varanic acid,3TMS,isomer #3C[C@H](CC[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3660.6Semi standard non polar33892256
Varanic acid,3TMS,isomer #4C[C@H](CC[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3694.7Semi standard non polar33892256
Varanic acid,4TMS,isomer #1C[C@H](CC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3675.2Semi standard non polar33892256
Varanic acid,1TBDMS,isomer #1C[C@H](CC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4016.4Semi standard non polar33892256
Varanic acid,1TBDMS,isomer #2C[C@H](CC[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4027.3Semi standard non polar33892256
Varanic acid,1TBDMS,isomer #3C[C@H](CC[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3920.7Semi standard non polar33892256
Varanic acid,1TBDMS,isomer #4C[C@H](CC[C@@H](O)[C@@H](O)C(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3994.7Semi standard non polar33892256
Varanic acid,2TBDMS,isomer #1C[C@H](CC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4233.2Semi standard non polar33892256
Varanic acid,2TBDMS,isomer #2C[C@H](CC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4140.7Semi standard non polar33892256
Varanic acid,2TBDMS,isomer #3C[C@H](CC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4187.9Semi standard non polar33892256
Varanic acid,2TBDMS,isomer #4C[C@H](CC[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4159.9Semi standard non polar33892256
Varanic acid,2TBDMS,isomer #5C[C@H](CC[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4215.0Semi standard non polar33892256
Varanic acid,2TBDMS,isomer #6C[C@H](CC[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4112.7Semi standard non polar33892256
Varanic acid,3TBDMS,isomer #1C[C@H](CC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4405.7Semi standard non polar33892256
Varanic acid,3TBDMS,isomer #2C[C@H](CC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4411.8Semi standard non polar33892256
Varanic acid,3TBDMS,isomer #3C[C@H](CC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4349.4Semi standard non polar33892256
Varanic acid,3TBDMS,isomer #4C[C@H](CC[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4366.4Semi standard non polar33892256
Varanic acid,4TBDMS,isomer #1C[C@H](CC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4568.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Varanic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0990-2009600000-03a9afbac544619ba6492017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Varanic acid GC-MS (3 TMS) - 70eV, Positivesplash10-000i-2201059000-728fa6a7dfdef5a44d712017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Varanic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Varanic 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 - Varanic acid 10V, Positive-QTOFsplash10-0gb9-0003900000-bccb9b8d53d48b7a4eb92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Varanic acid 20V, Positive-QTOFsplash10-0gb9-0019400000-20845b139c4f42ddf3e92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Varanic acid 40V, Positive-QTOFsplash10-00kg-1029100000-e64d24bdada468bf9ac62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Varanic acid 10V, Negative-QTOFsplash10-000i-1007900000-0c76a93c32d92d4bd0412017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Varanic acid 20V, Negative-QTOFsplash10-00du-1009100000-89308fceaf5d08dd4f982017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Varanic acid 40V, Negative-QTOFsplash10-0ab9-9007000000-3244541b477b1a59c4c52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Varanic acid 10V, Negative-QTOFsplash10-00kr-1002900000-b5d4ef16711be048d9d82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Varanic acid 20V, Negative-QTOFsplash10-0adr-9005200000-432ff87864ffc7286a4c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Varanic acid 40V, Negative-QTOFsplash10-0a4i-9006300000-553bfe38abe7822aeb9a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Varanic acid 10V, Positive-QTOFsplash10-0gic-0004900000-815713e2cdc936bf19cb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Varanic acid 20V, Positive-QTOFsplash10-0ir0-1259400000-04ce9abd5182f75ecb612021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Varanic acid 40V, Positive-QTOFsplash10-0btd-9744000000-33ccfd422b6445ffcd7f2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0(0-0) uMInfant (0-1 year old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0(0-0.1) uMInfant (0-1 year old)Both
Severe acute malnutrition
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022897
KNApSAcK IDNot Available
Chemspider ID17216172
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6538
PubChem Compound22833587
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSynthesis of diastereomers of 3 alpha,7 alpha,12 alpha, 24-tetrahydroxy- and 3 alpha,7 alpha,24-trihydroxy-5 beta-cholestan- 26-oic acids and their structures. Kurosawa T, Sato M, Nakano H, Tohma M. Steroids. 1996 Jul;61(7):421-8.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Casteels M, Schepers L, Parmentier G, Eyssen HJ, Mannaerts GP: Activation and peroxisomal beta-oxidation of fatty acids and bile acid intermediates in liver from Bombina orientalis and from the rat. Comp Biochem Physiol B. 1989;92(1):129-32. [PubMed:2706931 ]
  2. Vreken P, van Rooij A, Denis S, van Grunsven EG, Cuebas DA, Wanders RJ: Sensitive analysis of serum 3alpha, 7alpha, 12alpha,24-tetrahydroxy- 5beta-cholestan-26-oic acid diastereomers using gas chromatography-mass spectrometry and its application in peroxisomal D-bifunctional protein deficiency. J Lipid Res. 1998 Dec;39(12):2452-8. [PubMed:9831634 ]
  3. Clayton PT, Patel E, Lawson AM, Carruthers RA, Collins J: Bile acid profiles in peroxisomal 3-oxoacyl-coenzyme A thiolase deficiency. J Clin Invest. 1990 Apr;85(4):1267-73. [PubMed:2318981 ]

Enzymes

General function:
Involved in binding
Specific function:
Ileal protein which stimulates gastric acid and pepsinogen secretion. Seems to be able to bind to bile salts and bilirubins. Isoform 2 is essential for the survival of colon cancer cells to bile acid-induced apoptosis
Gene Name:
FABP6
Uniprot ID:
P51161
Molecular weight:
14371.2
References
  1. Kurz M, Brachvogel V, Matter H, Stengelin S, Thuring H, Kramer W: Insights into the bile acid transportation system: the human ileal lipid-binding protein-cholyltaurine complex and its comparison with homologous structures. Proteins. 2003 Feb 1;50(2):312-28. [PubMed:12486725 ]

Transporters

General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP)
Gene Name:
SLCO1B3
Uniprot ID:
Q9NPD5
Molecular weight:
77402.2
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Molecular weight:
76448.0
References
  1. Michalski C, Cui Y, Nies AT, Nuessler AK, Neuhaus P, Zanger UM, Klein K, Eichelbaum M, Keppler D, Konig J: A naturally occurring mutation in the SLC21A6 gene causing impaired membrane localization of the hepatocyte uptake transporter. J Biol Chem. 2002 Nov 8;277(45):43058-63. Epub 2002 Aug 23. [PubMed:12196548 ]
General function:
Involved in ATP binding
Specific function:
May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes
Gene Name:
ABCC3
Uniprot ID:
O15438
Molecular weight:
169341.1
General function:
Involved in ATP binding
Specific function:
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:
ABCB11
Uniprot ID:
O95342
Molecular weight:
146405.8
General function:
Involved in bile acid:sodium symporter activity
Specific function:
Plays a critical role in the sodium-dependent reabsorption of bile acids from the lumen of the small intestine. Plays a key role in cholesterol metabolism
Gene Name:
SLC10A2
Uniprot ID:
Q12908
Molecular weight:
37697.4
References
  1. Kramer W, Girbig F, Glombik H, Corsiero D, Stengelin S, Weyland C: Identification of a ligand-binding site in the Na+/bile acid cotransporting protein from rabbit ileum. J Biol Chem. 2001 Sep 21;276(38):36020-7. Epub 2001 Jul 10. [PubMed:11447228 ]
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
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:
SLCO1A2
Uniprot ID:
P46721
Molecular weight:
74144.1
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as the thyroid hormones T3 (triiodo-L-thyronine), T4 (thyroxine) and rT3, and of estrone-3-sulfate and taurocholate
Gene Name:
SLCO4A1
Uniprot ID:
Q96BD0
Molecular weight:
77192.5