Showing metabocard for 7a-Hydroxycholesterol (LMDB00339)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:47:39 UTC
Update Date2016-07-20 20:59:57 UTC
LmdbLMDB00339
Secondary Accession NumbersNone
Metabolite Identification
Common Name7a-Hydroxycholesterol
Description7alpha-hydroxycholesterol is an oxysterol and can serve as a biomarker for lipid peroxidation. (PMID: 17386651 ) Products of cholesterol oxidation accumulate within atherosclerotic plaque and have been proposed to contribute to inflammatory signalling in the diseased artery. (PMID: 17364953 ). 7alpha-hydroxycholesterol is a cholesterol oxide that has been described as biomarker of oxidative stress in subjects with impaired glucose tolerance and diabetes. (PMID: 16634125 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
7 alpha-HydroxycholesterolHMDB
7-a-HydroxycholesterolHMDB
7-alpha-HydroxycholesterolHMDB
7alpha-HydroxycholesterolHMDB
Cholest-5-ene-3beta,7alpha-diolHMDB
Cholest-5-en-3 beta,7 alpha-diol, (3beta,7alpha)-isomer, 14C-labeledHMDB
7 beta-HydroxycholesterolHMDB
7beta-HydroxycholesterolHMDB
Cholest-5-en-3 beta,7 alpha-diolHMDB
Cholest-5-en-3 beta,7 alpha-diol, (3beta)-isomerHMDB
Cholest-5-en-3beta,7beta-diolHMDB
Cholest-5-en-3 beta,7 alpha-diol, (3beta,7beta)-isomerHMDB
Chemical FormulaC27H46O2
Average Molecular Weight402.6529
Monoisotopic Molecular Weight402.349780716
IUPAC Name(1S,2R,5S,9S,11R,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 Name(1S,2R,5S,9S,11R,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
CAS Registry NumberNot Available
SMILES
CC(C)CCC[C@@H](C)[C@H]1CC[C@@H]2C3[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-AWBHSAGMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives 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-hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability50.32 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007c-1229000000-8b7536c0aaf1a204c485Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-6110590000-b66f740fbc107b812df8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0009200000-a31b2c397468b45366b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-2129100000-ec56e413c79f36bad24bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-5249000000-b8ddfa6034e8a89a74aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0003900000-554f04a87ac749f5ccdeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-0008900000-b67edccfb405ce918eb1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01bi-1009000000-111324aaf6701d08d72aSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Plasma
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDNot Available
HMDB IDHMDB0001496
FooDB IDFDB022655
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID42155
BioCyc IDNot Available
METLIN ID6280
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID89281
PubChem Compound ID53477732
Kegg Compound IDC03594
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kitano S, Yoshida Y, Kawano K, Hibi N, Niki E: Oxidative status of human low density lipoprotein isolated by anion-exchange high-performance liquid chromatography--assessment by total hydroxyoctadecadienoic acid, 7-hydroxycholesterol, and 8-iso-prostaglandin F(2alpha). Anal Chim Acta. 2007 Feb 28;585(1):86-93. Epub 2006 Dec 23. [17386651 ]
  2. Erridge C, Webb DJ, Spickett CM: 25-Hydroxycholesterol, 7beta-hydroxycholesterol and 7-ketocholesterol upregulate interleukin-8 expression independently of Toll-like receptor 1, 2, 4 or 6 signalling in human macrophages. Free Radic Res. 2007 Mar;41(3):260-6. [17364953 ]
  3. Ferderbar S, Pereira EC, Apolinario E, Bertolami MC, Faludi A, Monte O, Calliari LE, Sales JE, Gagliardi AR, Xavier HT, Abdalla DS: Cholesterol oxides as biomarkers of oxidative stress in type 1 and type 2 diabetes mellitus. Diabetes Metab Res Rev. 2007 Jan;23(1):35-42. [16634125 ]