Showing metabocard for 20α-Hydroxycholesterol (BMDB0006283)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:21:13 UTC
Update Date2020-04-22 15:17:11 UTC
BMDB IDBMDB0006283
Secondary Accession Numbers
  • BMDB06283
Metabolite Identification
Common Name20α-Hydroxycholesterol
Description20alpha-Hydroxycholesterol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 20alpha-hydroxycholesterol is considered to be a sterol lipid molecule. 20alpha-Hydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 20alpha-Hydroxycholesterol participates in a number of enzymatic reactions, within cattle. In particular, 20alpha-Hydroxycholesterol can be converted into 20a,22b-dihydroxycholesterol; which is mediated by the enzyme cholesterol side-chain cleavage enzyme, mitochondrial. In addition, 20alpha-Hydroxycholesterol can be biosynthesized from cholesterol through the action of the enzyme cholesterol side-chain cleavage enzyme, mitochondrial. In cattle, 20alpha-hydroxycholesterol is involved in the metabolic pathway called the steroidogenesis pathway.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
20a-HydroxycholesterolGenerator
20Α-hydroxycholesterolGenerator
(20S)-20-HydroxycholesterolMeSH
(20S)-Cholest-5-ene-3 beta,20-diolMeSH
20 alpha-HydroxycholesterolMeSH
20-HydroxycholesterolMeSH
20-Hydroxycholesterol, (3beta,20 xi)-isomerMeSH
20-Hydroxycholesterol, 3H-labeled, (3beta,20 xi)-isomerMeSH
20R-HydroxycholesterolMeSH
(3beta,20R)-Cholest-5-ene-3,20-diolHMDB
20alpha-Hydroxy cholesterolHMDB
Chemical FormulaC27H46O2
Average Molecular Weight402.6529
Monoisotopic Molecular Weight402.349780716
IUPAC Name(1S,2R,5S,10S,11S,14S,15S)-14-[(2R)-2-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol
Traditional Name20a-hydroxy cholesterol
CAS Registry Number516-72-3
SMILES
CC(C)CCC[C@@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChI Identifier
InChI=1S/C27H46O2/c1-18(2)7-6-14-27(5,29)24-11-10-22-21-9-8-19-17-20(28)12-15-25(19,3)23(21)13-16-26(22,24)4/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t20-,21-,22-,23-,24-,25-,26-,27+/m0/s1
InChI KeyMCKLJFJEQRYRQT-MGNSQDQZSA-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
  • 20-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 3-beta-hydroxysteroid
  • Delta-5-steroid
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen 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
  • Membrane
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.06ALOGPS
logP5.8ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.3 m³·mol⁻¹ChemAxon
Polarizability51.1 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
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-1139000000-2c00b5523723b960fa5aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-3011490000-84aa9e3675270a653af2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0009200000-78634a50a076fbe30975View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05tr-3039100000-08dfa0b5e30063e9930aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0avi-8189000000-c3bb06d3d099c9c4f440View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0003900000-4b881293f669607058ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-1039800000-4c4801e96fa5d9126da5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059i-3089000000-806365cc5d181d0d25d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-079f76b4d985e4b92c9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0000900000-079f76b4d985e4b92c9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0009500000-63d3ce6872e526ad179dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f9i-0109100000-ba23251dfb42b1ea90e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9147100000-ed7f14edc5be9509ea46View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9820000000-1d6a2993646068927786View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006283
DrugBank IDDB04704
Phenol Explorer Compound IDNot Available
FooDB IDFDB023876
KNApSAcK IDNot Available
Chemspider ID389586
KEGG Compound IDC05500
BioCyc ID20A-HYDROXY-CHOLESTEROL
BiGG ID1443018
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440711
PDB IDHC2
ChEBI ID1296
References
Synthesis ReferenceMijares, A.; Cargill, David I.; Glasel, Jay A.; Lieberman, Seymour. C-20 epimers of 20-hydroxycholesterol. Journal of Organic Chemistry (1967), 32(3), 810-12.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available