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Showing metabocard for 24-Hydroxycholesterol (BMDB0001419)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:45:40 UTC
Update Date2020-05-21 16:28:49 UTC
BMDB IDBMDB0001419
Secondary Accession Numbers
  • BMDB01419
Metabolite Identification
Common Name24-Hydroxycholesterol
Description24-Hydroxycholesterol, also known as cholest-5-ene-3,24-diol or cerebrosterol, belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. Thus, 24-hydroxycholesterol is considered to be a sterol lipid molecule. 24-Hydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(24S)-HydroxycholesterolChEBI
24S-Hydroxy-cholesterolChEBI
CerebrosterolChEBI
Cholest-5-en-3beta,24S-diolChEBI
Cholest-5-ene-3,24-diolChEBI
(24S)-24-HydroxycholesterolKegg
(24S)-Cholest-5-ene-3beta,24-diolKegg
Cholest-5-en-3b,24S-diolGenerator
Cholest-5-en-3β,24S-diolGenerator
(24S)-Cholest-5-ene-3b,24-diolGenerator
(24S)-Cholest-5-ene-3β,24-diolGenerator
24(S)-HydroxycholesterolHMDB
24S-Cholest-5-ene-3b,24-diolHMDB
24S-HydroxycholesterolHMDB
CerebrosterinHMDB
Cholest-5-ene-3b,24b-diolHMDB
Chemical FormulaC27H46O2
Average Molecular Weight402.6529
Monoisotopic Molecular Weight402.349780716
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number474-73-7
SMILESNot Available
InChI Identifier
InChI=1S/C27H46O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,26+,27-/m1/s1
InChI KeyIOWMKBFJCNLRTC-XWXSNNQWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentDihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • 24-hydroxysteroid
  • Dihydroxy bile acid, alcohol, or derivatives
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001419
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022611
KNApSAcK IDNot Available
Chemspider ID108790
KEGG Compound IDC13550
BioCyc IDNot Available
BiGG ID2197434
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound121948
PDB IDNot Available
ChEBI ID34310
References
Synthesis ReferencePrasad V V; Ponticorvo L; Lieberman S Identification of 24-hydroxycholesterol in bovine adrenals in both free and esterified forms and in bovine brains as its sulfate ester. Journal of steroid biochemistry (1984), 21(6), 733-6.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Lanosterol 14-alpha demethylase
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
A cytochrome P450 monooxygenase involved in sterol biosynthesis. Catalyzes 14-alpha demethylation of lanosterol and 24,25-dihydrolanosterol likely through sequential oxidative conversion of 14-alpha methyl group to hydroxymethyl, then to carboxylaldehyde, followed by the formation of the delta 14,15 double bond in the sterol core and concomitant release of formic acid. Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase).
Gene Name:
CYP51A1
Uniprot ID:
Q4PJW3
Molecular weight:
56596.0
Reactions
24-Hydroxycholesterol + NADPH + Oxygen → (24R)-Cholest-5-ene-3-beta,7-alpha,24-triol + NADP + Waterdetails
Enzyme Details
2. Cytochrome P450 3A28
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A28
Uniprot ID:
P79102
Molecular weight:
58152.0
Reactions
Cholesterol + NADPH + Oxygen → 24-Hydroxycholesterol + NADP + Waterdetails