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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-05-11 14:21:33 UTC
Update Date2017-10-23 19:04:19 UTC
HMDB IDHMDB0006119
Secondary Accession Numbers
  • HMDB06119
Metabolite Identification
Common Name7b-Hydroxycholesterol
Description7b-Hydroxycholesterol is identified in atheromatous plaques and in plasma of atherosclerotic patients.(PMID: 16604541 ). 7b-Hydroxycholesterol induces apoptosis in Caco-2 cells and alters Lysosomal membrane integrity. It exhibites a specific enhancement of oxidative stress and of endonuclease G expression. (PMID: 17136497 ).
Structure
Thumb
Synonyms
ValueSource
(3beta,7beta)-Cholest-5-ene-3,7-diolChEBI
7-HYDROXYCHOLESTEROLChEBI
(3b,7b)-Cholest-5-ene-3,7-diolGenerator
(3β,7β)-cholest-5-ene-3,7-diolGenerator
5-Cholestene-3beta,7beta-diolHMDB
7beta-HydroxycholesterolHMDB
Cholest-5-ene-3beta,7beta-diolHMDB
7 alpha-HydroxycholesterolMeSH
7 beta-HydroxycholesterolMeSH
7alpha-HydroxycholesterolMeSH
Cholest-5-en-3 beta,7 alpha-diolMeSH
Cholest-5-en-3 beta,7 alpha-diol, (3beta)-isomerMeSH
Cholest-5-en-3 beta,7 alpha-diol, (3beta,7alpha)-isomer, 14C-labeledMeSH
Cholest-5-en-3 beta,7 alpha-diol, (3beta,7beta)-isomerMeSH
Cholest-5-en-3beta,7beta-diolMeSH
Chemical FormulaC27H46O2
Average Molecular Weight402.6529
Monoisotopic Molecular Weight402.349780716
IUPAC Name(1S,2R,5S,9R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol
Traditional Name7 β-hydroxycholesterol
CAS Registry Number566-27-8
SMILES
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChI Identifier
InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24+,25+,26+,27-/m1/s1
InChI KeyOYXZMSRRJOYLLO-KGZHIOMZSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cholesterols and derivatives. These are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol
  • Cholesterol-skeleton
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • 3-beta-hydroxysteroid
  • 7-alpha-hydroxysteroid
  • 7-hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

  Health condition:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Cell and elements:

Source:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Multicellular process:

Role

Industrial application:

  Pharmaceutical industry:

Biological role:

  Molecular messenger:

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 Solubility0.00048 g/LALOGPS
logP5.61ALOGPS
logP5.96ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.05 m³·mol⁻¹ChemAxon
Polarizability51.11 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007c-1229000000-8b7536c0aaf1a204c485View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-6110590000-3008d2fd9fd93235cd84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0009200000-dd83a63fa5280b1a0a32View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-2129100000-d4fcf32706fb430f9b9fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-7369000000-3cb2e62a7e2f2c82bd31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0003900000-631080b9e26008e235d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-0009800000-c89cf39b6f8d49fe8f54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-1009000000-2c0cdf0af0d6dd2fad2fView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.011 +/- 0.0027 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.003 +/- 0.0006 uMAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.004 +/- 0.0017 uMAdult (>18 years old)BothMultiple Sclerosis details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Multiple sclerosis
  1. Leoni V, Lutjohann D, Masterman T: Levels of 7-oxocholesterol in cerebrospinal fluid are more than one thousand times lower than reported in multiple sclerosis. J Lipid Res. 2005 Feb;46(2):191-5. Epub 2004 Dec 1. [PubMed:15576852 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023832
KNApSAcK IDNot Available
Chemspider ID415508
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound473141
PDB IDHCR
ChEBI ID42989
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Prunet C, Montange T, Vejux A, Laubriet A, Rohmer JF, Riedinger JM, Athias A, Lemaire-Ewing S, Neel D, Petit JM, Steinmetz E, Brenot R, Gambert P, Lizard G: Multiplexed flow cytometric analyses of pro- and anti-inflammatory cytokines in the culture media of oxysterol-treated human monocytic cells and in the sera of atherosclerotic patients. Cytometry A. 2006 May;69(5):359-73. [PubMed:16604541 ]
  2. Roussi S, Gosse F, Aoude-Werner D, Zhang X, Marchioni E, Geoffroy P, Miesch M, Raul F: Mitochondrial perturbation, oxidative stress and lysosomal destabilization are involved in 7beta-hydroxysitosterol and 7beta-hydroxycholesterol triggered apoptosis in human colon cancer cells. Apoptosis. 2007 Jan;12(1):87-96. [PubMed:17136497 ]