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Showing metabocard for 3 beta-Hydroxy-5-cholestenoate (HMDB12453)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version3.6
Creation Date2009-07-13 12:02:10 UTC
Update Date2017-03-02 21:32:33 UTC
HMDB IDHMDB12453
Secondary Accession NumbersNone
Metabolite Identification
Common Name3 beta-Hydroxy-5-cholestenoate
Description3 beta-Hydroxy-5-cholestenoate is found in the primary bile acid biosynthesis pathway. 3 beta-Hydroxy-5-cholestenoate is created from Cholest-5-ene-3 beta,26-diol through the action of CYP27A (E1.14.13.15). 3 beta-Hydroxy-5-cholestenoate is then converted to 3 beta,7alpha-Dihydroxy-5-cholestenoate by the action of CYP7B (E1.14.13.100).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3beta)-3-Hydroxy-cholest-5-en-26-OateHMDB
(3beta)-3-Hydroxy-cholest-5-en-26-Oic acidHMDB
3 beta-Hydroxycholest-5-en-27-OateHMDB
3 beta-Hydroxycholest-5-en-27-Oic acidHMDB
3-HCOAHMDB
3-Hydroxy-5-cholesten-26-OateHMDB
3-Hydroxy-5-cholesten-26-Oic acidHMDB
3-Hydroxy-5-cholestenoateHMDB
3-Hydroxy-5-cholestenoic acidHMDB
3beta-Hydroxy-5-cholesten-26-OateHMDB
3beta-Hydroxy-5-cholesten-26-Oic acidHMDB
3beta-Hydroxy-5-cholestenoateHMDB
3beta-Hydroxy-5-cholestenoic acidHMDB
Chemical FormulaC27H44O3
Average Molecular Weight416.6365
Monoisotopic Molecular Weight416.329045274
IUPAC Name(6R)-6-[(2R,5S,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-2-methylheptanoic acid
Traditional Name(6R)-6-[(2R,5S,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-2-methylheptanoic acid
CAS Registry Number6561-58-6
SMILES
C[C@H](CCCC(C)C(O)=O)C1CCC2C3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C
InChI Identifier
InChI=1S/C27H44O3/c1-17(6-5-7-18(2)25(29)30)22-10-11-23-21-9-8-19-16-20(28)12-14-26(19,3)24(21)13-15-27(22,23)4/h8,17-18,20-24,28H,5-7,9-16H2,1-4H3,(H,29,30)/t17-,18?,20+,21?,22?,23?,24?,26+,27-/m1/s1
InChI KeyWVXOMPRLWLXFAP-UBJAGWMESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassSteroids and steroid derivatives
Direct ParentMonohydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Monohydroxy bile acid, alcohol, or derivatives
  • Steroid acid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.000485 mg/mLALOGPS
logP5.57ALOGPS
logP6.05ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)4.83ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity122.31 m3·mol-1ChemAxon
Polarizability50.2 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
27-Hydroxylase DeficiencySMP00720Not Available
Bile Acid BiosynthesisSMP00035map00120
Cerebrotendinous Xanthomatosis (CTX)SMP00315Not Available
Congenital Bile Acid Synthesis Defect Type IISMP00314Not Available
Congenital Bile Acid Synthesis Defect Type IIISMP00318Not Available
Familial Hypercholanemia (FHCA)SMP00317Not Available
Zellweger SyndromeSMP00316Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB029069
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC17333
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12453
Metagene LinkHMDB12453
METLIN IDNot Available
PubChem Compound53481407
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Sterol 26-hydroxylase, mitochondrial
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the first step in the oxidation of the side chain of sterol intermediates; the 27-hydroxylation of 5-beta-cholestane-3-alpha,7-alpha,12-alpha-triol. Has also a vitamin D3-25-hydroxylase activity.
Gene Name:
CYP27A1
Uniprot ID:
Q02318
Molecular weight:
60234.28
Reactions
27-Hydroxycholesterol + Oxygen + NADPH + Hydrogen Ion → 3 beta-Hydroxy-5-cholestenoate + NADP + Waterdetails
Enzyme Details
2. 25-hydroxycholesterol 7-alpha-hydroxylase
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP7B1
Uniprot ID:
O75881
Molecular weight:
58255.325
Reactions
3 beta-Hydroxy-5-cholestenoate + Oxygen + NADPH + Hydrogen Ion → 3 beta,7 alpha-Dihydroxy-5-cholestenoate + NADP + Waterdetails