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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:53 UTC
Update Date2022-03-07 02:49:15 UTC
HMDB IDHMDB0002431
Secondary Accession Numbers
  • HMDB02431
Metabolite Identification
Common Name12b-Hydroxy-5b-cholanoic acid
Description12b-Hydroxy-5b-cholanoic acid, also known as 12-hydroxy-(5b,12b)-cholan-24-Oate or 12beta-hydroxy-5beta-cholanoate, belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group. 12b-Hydroxy-5b-cholanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1582752249
Synonyms
ValueSource
12b-Hydroxy-5b-cholanoateGenerator
12-Hydroxy-(5b,12b)-cholan-24-OateHMDB
12-Hydroxy-(5b,12b)-cholan-24-Oic acidHMDB
12b-Hydroxy-5b-cholan-24-OateHMDB
12b-Hydroxy-5b-cholan-24-Oic acidHMDB
12b-Hydroxy-5b-cholanic acidHMDB
12beta-Hydroxy-5beta-cholanoateHMDB
12beta-Hydroxy-5beta-cholanoic acidHMDB
(4R)-4-[(1S,2S,7S,10R,11S,14R,15R,16R)-16-Hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoateHMDB
12Β-hydroxy-5β-cholanoateHMDB
12Β-hydroxy-5β-cholanoic acidHMDB
12b-Hydroxy-5b-cholanoic acidGenerator
Chemical FormulaC24H40O3
Average Molecular Weight376.5726
Monoisotopic Molecular Weight376.297745146
IUPAC Name(4R)-4-[(1S,2S,7S,10R,11S,14R,15R,16R)-16-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
Traditional Name12b-hydroxy-5b-cholanoic acid
CAS Registry Number15173-23-6
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])CCCC[C@]4(C)[C@@]3([H])C[C@@H](O)[C@]12C)[C@H](C)CCC(O)=O
InChI Identifier
InChI=1S/C24H40O3/c1-15(7-12-22(26)27)18-10-11-19-17-9-8-16-6-4-5-13-23(16,2)20(17)14-21(25)24(18,19)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16+,17+,18-,19+,20+,21-,23+,24-/m1/s1
InChI KeyOBUOWZOYJNAMCZ-ORVKXXEISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentMonohydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Monohydroxy bile acid, alcohol, or derivatives
  • Hydroxysteroid
  • 12-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
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 Solubility0.0011 g/LALOGPS
logP4.5ALOGPS
logP5.18ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-0.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity107.53 m³·mol⁻¹ChemAxon
Polarizability45.28 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+188.76731661259
DarkChem[M-H]-182.70231661259
DeepCCS[M-2H]-226.38730932474
DeepCCS[M+Na]+200.45830932474
AllCCS[M+H]+197.332859911
AllCCS[M+H-H2O]+195.132859911
AllCCS[M+NH4]+199.432859911
AllCCS[M+Na]+200.032859911
AllCCS[M-H]-197.632859911
AllCCS[M+Na-2H]-198.832859911
AllCCS[M+HCOO]-200.232859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
12b-Hydroxy-5b-cholanoic acid,1TMS,isomer #1C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CCCC[C@]4(C)[C@H]3C[C@@H](O[Si](C)(C)C)[C@@]21C3157.2Semi standard non polar33892256
12b-Hydroxy-5b-cholanoic acid,1TMS,isomer #1C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CCCC[C@]4(C)[C@H]3C[C@@H](O[Si](C)(C)C)[C@@]21C2943.3Standard non polar33892256
12b-Hydroxy-5b-cholanoic acid,1TMS,isomer #1C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CCCC[C@]4(C)[C@H]3C[C@@H](O[Si](C)(C)C)[C@@]21C3491.2Standard polar33892256
12b-Hydroxy-5b-cholanoic acid,1TMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CCCC[C@]4(C)[C@H]3C[C@@H](O)[C@@]21C3078.6Semi standard non polar33892256
12b-Hydroxy-5b-cholanoic acid,1TMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CCCC[C@]4(C)[C@H]3C[C@@H](O)[C@@]21C2988.9Standard non polar33892256
12b-Hydroxy-5b-cholanoic acid,1TMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CCCC[C@]4(C)[C@H]3C[C@@H](O)[C@@]21C3490.8Standard polar33892256
12b-Hydroxy-5b-cholanoic acid,2TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CCCC[C@]4(C)[C@H]3C[C@@H](O[Si](C)(C)C)[C@@]21C3091.3Semi standard non polar33892256
12b-Hydroxy-5b-cholanoic acid,2TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CCCC[C@]4(C)[C@H]3C[C@@H](O[Si](C)(C)C)[C@@]21C3039.2Standard non polar33892256
12b-Hydroxy-5b-cholanoic acid,2TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CCCC[C@]4(C)[C@H]3C[C@@H](O[Si](C)(C)C)[C@@]21C3470.6Standard polar33892256
12b-Hydroxy-5b-cholanoic acid,1TBDMS,isomer #1C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CCCC[C@]4(C)[C@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@]21C3398.1Semi standard non polar33892256
12b-Hydroxy-5b-cholanoic acid,1TBDMS,isomer #1C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CCCC[C@]4(C)[C@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@]21C3184.6Standard non polar33892256
12b-Hydroxy-5b-cholanoic acid,1TBDMS,isomer #1C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CCCC[C@]4(C)[C@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@]21C3637.4Standard polar33892256
12b-Hydroxy-5b-cholanoic acid,1TBDMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CCCC[C@]4(C)[C@H]3C[C@@H](O)[C@@]21C3344.1Semi standard non polar33892256
12b-Hydroxy-5b-cholanoic acid,1TBDMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CCCC[C@]4(C)[C@H]3C[C@@H](O)[C@@]21C3225.6Standard non polar33892256
12b-Hydroxy-5b-cholanoic acid,1TBDMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CCCC[C@]4(C)[C@H]3C[C@@H](O)[C@@]21C3623.8Standard polar33892256
12b-Hydroxy-5b-cholanoic acid,2TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CCCC[C@]4(C)[C@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@]21C3595.5Semi standard non polar33892256
12b-Hydroxy-5b-cholanoic acid,2TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CCCC[C@]4(C)[C@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@]21C3533.3Standard non polar33892256
12b-Hydroxy-5b-cholanoic acid,2TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CCCC[C@]4(C)[C@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@]21C3684.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 12b-Hydroxy-5b-cholanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ot-0529000000-3b69425c7ae697ec414d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12b-Hydroxy-5b-cholanoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0a4i-3412790000-eb52115fafe72be037222017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12b-Hydroxy-5b-cholanoic 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 - 12b-Hydroxy-5b-cholanoic acid 10V, Positive-QTOFsplash10-0a4i-0009000000-15d32456a05796c74b9e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12b-Hydroxy-5b-cholanoic acid 20V, Positive-QTOFsplash10-0a4l-1129000000-42a672f4744641eef19e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12b-Hydroxy-5b-cholanoic acid 40V, Positive-QTOFsplash10-0002-9436000000-b906bafebf3f347be5882017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12b-Hydroxy-5b-cholanoic acid 10V, Negative-QTOFsplash10-004i-0009000000-f317b23fea7a9c31f96a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12b-Hydroxy-5b-cholanoic acid 20V, Negative-QTOFsplash10-0a6r-0009000000-7369aef23afe9f4d2fd42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12b-Hydroxy-5b-cholanoic acid 40V, Negative-QTOFsplash10-0a4l-9007000000-9e6e385970953e2c04902017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12b-Hydroxy-5b-cholanoic acid 10V, Negative-QTOFsplash10-004i-0009000000-eccc9e9b8c78169f53132021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12b-Hydroxy-5b-cholanoic acid 20V, Negative-QTOFsplash10-056r-0009000000-ba11f3143c6ba7fb91e92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12b-Hydroxy-5b-cholanoic acid 40V, Negative-QTOFsplash10-00di-1049000000-e239941ccc7bfead9dff2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12b-Hydroxy-5b-cholanoic acid 10V, Positive-QTOFsplash10-004i-0019000000-b5f69b5609f9c70066ac2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12b-Hydroxy-5b-cholanoic acid 20V, Positive-QTOFsplash10-0a6r-4295000000-af9a318aaf3d2a121d9c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12b-Hydroxy-5b-cholanoic acid 40V, Positive-QTOFsplash10-0a4l-9430000000-d8b1a979438d056e7fc82021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023003
KNApSAcK IDNot Available
Chemspider ID4446900
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283812
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. ENEROTH P: THIN-LAYER CHROMATOGRAPHY OF BILE ACIDS. J Lipid Res. 1963 Jan;4:11-6. [PubMed:14167657 ]

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