Showing metabocard for 22b-Hydroxycholesterol (BMDB0004035)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:07:21 UTC
Update Date2020-05-11 20:31:01 UTC
BMDB IDBMDB0004035
Secondary Accession Numbers
  • BMDB04035
Metabolite Identification
Common Name22b-Hydroxycholesterol
Description22b-Hydroxycholesterol, also known as cholest-5-en-3b,22R-diol or 22(R)OH cholesterol, 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, 22b-hydroxycholesterol is considered to be a sterol lipid molecule. 22b-Hydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 22b-Hydroxycholesterol exists in all eukaryotes, ranging from yeast to humans. 22b-Hydroxycholesterol participates in a number of enzymatic reactions, within cattle. In particular, 22b-Hydroxycholesterol can be converted into 20a,22b-dihydroxycholesterol through its interaction with the enzyme cholesterol side-chain cleavage enzyme, mitochondrial. In addition, 22b-Hydroxycholesterol can be biosynthesized from cholesterol through its interaction with the enzyme cholesterol side-chain cleavage enzyme, mitochondrial. In cattle, 22b-hydroxycholesterol is involved in the metabolic pathway called the steroidogenesis pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3beta,22R)-Cholest-5-ene-3,22-diolChEBI
22beta-HydroxycholesterolChEBI
22R-HydroxycholesterolChEBI
Cholest-5-en-3beta,22R-diolChEBI
(22R)-22-HydroxycholesterolKegg
(3b,22R)-Cholest-5-ene-3,22-diolGenerator
(3Β,22R)-cholest-5-ene-3,22-diolGenerator
22Β-hydroxycholesterolGenerator
Cholest-5-en-3b,22R-diolGenerator
Cholest-5-en-3β,22R-diolGenerator
22-Hydroxycholesterol, (3beta,20R,22R)-isomerHMDB
22-Hydroxycholesterol, (3beta,20R,22S)-isomerHMDB
Cholest-5-ene-3beta,22-diolHMDB
22(R)-HydroxycholesterolHMDB
22-Hydroxycholesterol, (3beta,22S)-isomerHMDB
22(R)OH CholesterolHMDB
22-HydroxycholesterolHMDB
22-Hydroxycholesterol, (3beta,22R)-isomerHMDB
22S-HydroxycholesterolHMDB
Chemical FormulaC27H46O2
Average Molecular Weight402.6529
Monoisotopic Molecular Weight402.349780716
IUPAC Name(1S,2R,5S,10S,11S,14R,15S)-14-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol
Traditional Name22R-hydroxycholesterol
CAS Registry Number22348-64-7
SMILES
[H][C@@]12CC[C@H]([C@H](C)[C@H](O)CCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C27H46O2/c1-17(2)6-11-25(29)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+/m0/s1
InChI KeyRZPAXNJLEKLXNO-GFKLAVDKSA-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
  • Cholesterol
  • Cholesterol-skeleton
  • Cholestane-skeleton
  • Dihydroxy bile acid, alcohol, or derivatives
  • 22-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • 3-beta-hydroxysteroid
  • 3-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • 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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.69ALOGPS
logP5.8ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.73ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.21 m³·mol⁻¹ChemAxon
Polarizability50.77 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, Positivesplash10-00dr-1009000000-ed60780a407ecfba86a3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-2111490000-e04dc3bb7ab36f5571f8View 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, Positivesplash10-0f79-0009200000-2ae8fb6172d46e818cefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-2119100000-9925177c38f63ddc14a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-6049000000-44d8c7fcd6055391f8ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0004900000-10b9f0186b2a2ac37d53View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-1019700000-6b5a6ee8410d635f82c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-4059000000-8d88574ef4b0b7d39b85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gbi-0109200000-bd7670f27e11ece2eac0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-5339000000-858a48abc2f1b02935f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-6960000000-73b0982e9fcef4fa83d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-84d3363c4aa86f104c55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0012900000-973e1345841477d95a76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uea-7049300000-8042d2ca5cd8469196daView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
Biospecimen Locations
  • Adrenal Cortex
  • Epidermis
  • Fibroblasts
  • Neuron
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adrenal CortexExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0004035
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023285
KNApSAcK IDNot Available
Chemspider ID146693
KEGG Compound IDC05502
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7006
PubChem Compound167685
PDB IDNot Available
ChEBI ID67237
References
Synthesis ReferenceKoreeda, Masato; Ricca, Daniel J. Chirality transfer in stereoselective synthesis. A highly stereocontrolled synthesis of 22-hydroxylated steroid side chains via the [2,3]-Wittig rearrangement. Journal of Organic Chemistry (1986), 51(21), 4090-2.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available