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Showing metabocard for (24R)-Cholest-5-ene-3-beta,7-alpha,24-triol (HMDB11644)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
enzymes (1) Show 1 protein
Record Information
Version3.6
Creation Date2009-02-02 11:59:47 UTC
Update Date2017-03-02 21:31:55 UTC
HMDB IDHMDB11644
Secondary Accession NumbersNone
Metabolite Identification
Common Name(24R)-Cholest-5-ene-3-beta,7-alpha,24-triol
Description(24R)-Cholest-5-ene-3-beta,7-alpha,24-triol is a hydroxysterol and a bile acid intermediate. It is produced from the reaction of 24(R)-Hydroxycholesterol with the enzyme CYP39A, which is also known as 24-hydroxycholesterol 7alpha-hydroxylase (EC 1.14.13.99). This enzyme catalyzes the following reaction: (24R)-cholest-5-ene-3beta,24-diol + NADPH + H+ O2 = (24R)-cholest-5-ene-3beta,7alpha,24-triol + NADP+ + H2O. This leads to the 7-alpha hydroxylation of 24(R)-hydroxycholesterol. This enzyme can act on both the 24R and 24S isomers.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(24R)-Cholest-5-ene 3-b,7-a,24-triolHMDB
(24R)-Cholest-5-ene-3beta,7alpha,24-triolHMDB
5a-Cholesta-7,24-dien-3-b-olHMDB
5a-Cholesta-7,24-dien-3-beta-olHMDB
Chemical FormulaC27H46O3
Average Molecular Weight418.6523
Monoisotopic Molecular Weight418.344695338
IUPAC Name(1S,2R,5S,9S,10S,11S,15R)-14-[(2R,5R)-5-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol
Traditional Name(1S,2R,5S,9S,10S,11S,15R)-14-[(2R,5R)-5-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol
CAS Registry NumberNot Available
SMILES
[H][C@@]12CCC([C@H](C)CC[C@@H](O)C(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C27H46O3/c1-16(2)23(29)9-6-17(3)20-7-8-21-25-22(11-13-27(20,21)5)26(4)12-10-19(28)14-18(26)15-24(25)30/h15-17,19-25,28-30H,6-14H2,1-5H3/t17-,19+,20?,21+,22+,23-,24-,25+,26+,27-/m1/s1
InChI KeyZNCHPOYZMVVJCK-DPFMVWRKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassSteroids and steroid derivatives
Direct ParentTrihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Trihydroxy bile acid, alcohol, or derivatives
  • 24-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 7-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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 Solubility0.0085 mg/mLALOGPS
logP4.28ALOGPS
logP4.65ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.66ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity123.65 m3·mol-1ChemAxon
Polarizability51.47 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot 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 IDFDB028340
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-10481
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB11644
Metagene LinkHMDB11644
METLIN IDNot Available
PubChem Compound53481010
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. 24-hydroxycholesterol 7-alpha-hydroxylase
General function:
Involved in monooxygenase activity
Specific function:
Involved in the bile acid metabolism. Has a preference for 24-hydroxycholesterol, and converts it into a 7-alpha-hydroxylated product.
Gene Name:
CYP39A1
Uniprot ID:
Q9NYL5
Molecular weight:
54115.29
Reactions
(24R)-Cholest-5-ene-3-beta,24-diol + NADPH + Oxygen → (24R)-Cholest-5-ene-3-beta,7-alpha,24-triol + NADP + Waterdetails