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Record Information
Version1.0
Creation Date2016-09-30 22:51:15 UTC
Update Date2020-05-21 16:28:49 UTC
BMDB IDBMDB0002103
Secondary Accession Numbers
  • BMDB02103
Metabolite Identification
Common Name27-Hydroxycholesterol
Description27-Hydroxycholesterol, also known as cholest-5-ene-3b,27-diol, 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, 27-hydroxycholesterol is considered to be a sterol lipid molecule. 27-Hydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 27-Hydroxycholesterol is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
(25R)-26-HydroxycholesterolChEBI
5-Cholestene-3beta,27-diolChEBI
Cholest-5-ene-3beta,27-diolChEBI
5-Cholestene-3b,27-diolGenerator
5-Cholestene-3β,27-diolGenerator
Cholest-5-ene-3b,27-diolGenerator
Cholest-5-ene-3β,27-diolGenerator
(25R)-Cholest-5-ene-3b,26-diolHMDB
(25R)-Cholest-5-ene-3beta,26-diolHMDB
(3-beta)-Cholest-5-ene-3,26-diolHMDB
(3b,25R)-Cholest-5-ene-3,26-diolHMDB
(3beta,25R)-Cholest-5-ene-3,26,diolHMDB
26-Hydroxycholesterol(25R)HMDB
Cholest-(25R)-5-en-3beta,26-diolHMDB
Cholest-5-ene-3-b,27-diolHMDB
Cholest-5-ene-3-beta,26-diolHMDB
Cholest-5-ene-3-beta,27-diolHMDB
Cholest-5-ene-3beta,26-diolHMDB
Cholest-5-ene-3 beta,27-diolHMDB
5-Cholestene-3 beta,27-diolHMDB
(25R)-Cholest-5-ene-3β,26-diolHMDB
(3Β,25R)-cholest-5-ene-3,26-diolHMDB
(3beta,25R)-Cholest-5-ene-3,26-diolHMDB
Cholest-5-ene-3β,26-diolHMDB
(3Β)-cholest-5-ene-3,26-diolHMDB
(3beta)-Cholest-5-ene-3,26-diolHMDB
26-HydroxycholesterolHMDB
(3 beta,25R)-Cholest-5-ene-3,26-diolHMDB
26-Hydroxycholesterol, (25R)HMDB
(25R)-Cholest-5-ene-3 beta,26-diolHMDB
Chemical FormulaC27H46O2
Average Molecular Weight402.6529
Monoisotopic Molecular Weight402.349780716
IUPAC Name(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,6R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
Traditional Name(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,6R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
CAS Registry Number20380-11-4
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC[C@@H](C)CO
InChI Identifier
InChI=1S/C27H46O2/c1-18(17-28)6-5-7-19(2)23-10-11-24-22-9-8-20-16-21(29)12-14-26(20,3)25(22)13-15-27(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3/t18-,19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChI KeyFYHRJWMENCALJY-YSQMORBQSA-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
  • 26-hydroxysteroid
  • Dihydroxy bile acid, alcohol, or derivatives
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • 3-beta-hydroxysteroid
  • Delta-5-steroid
  • Fatty alcohol
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Primary 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
logP6.21ALOGPS
logP5.75ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)17.42ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity122.47 m³·mol⁻¹ChemAxon
Polarizability51.56 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00du-0009000000-c409240ea9f4c08e2ba0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-1211490000-d6f5e80defdccceda31cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0009200000-9ee1df2377674be6691cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-2109000000-2471d899cb75de6d3684View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0r29-3139000000-969ef6deb6437f21d9adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0004900000-2045d37649040dcd2d05View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-0009500000-ac02d066655429b00b85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-3009000000-8b6280720e1ee0be80b4View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
Biospecimen Locations
  • Brain
  • Fibroblasts
  • Neuron
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected 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 IDHMDB0002103
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022846
KNApSAcK IDNot Available
Chemspider ID110495
KEGG Compound IDC06340
BioCyc IDNot Available
BiGG ID48021
Wikipedia Link27-Hydroxycholesterol
METLIN ID6487
PubChem Compound123976
PDB IDNot Available
ChEBI ID76591
References
Synthesis ReferenceHausheer, Frederick H.; Haridas, Kochat. Process for preparing 27-hydroxycholesterol and related derivatives. PCT Int. Appl. (1997), 38 pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Catalyzes the isomerization of prostaglandin H2 to prostacyclin (= prostaglandin I2).
Gene Name:
PTGIS
Uniprot ID:
Q29626
Molecular weight:
56629.0
Reactions
Cholesterol + 3 NADPH + 3 Oxygen → 27-Hydroxycholesterol +3 NADP +4 Waterdetails
27-Hydroxycholesterol + NADPH + Oxygen → 7-a,27-dihydroxycholesterol + NADP + Waterdetails
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
A cytochrome P450 monooxygenase that catalyzes the side-chain hydroxylation and cleavage of cholesterol to pregnenolone, the precursor of most steroid hormones (PubMed:11412116). Catalyzes three sequential oxidation reactions of cholesterol, namely the hydroxylation at C22 followed with the hydroxylation at C20 to yield 20R,22R-hydroxycholesterol that is further cleaved between C20 and C22 to yield the C21-steroid pregnenolone and 4-methylpentanal (PubMed:11412116). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate and reducing the second into a water molecule. Two electrons are provided by NADPH via a two-protein mitochondrial transfer system comprising flavoprotein FDXR (adrenodoxin/ferredoxin reductase) and nonheme iron-sulfur protein FDX1 or FDX2 (adrenodoxin/ferredoxin) (PubMed:11412116).
Gene Name:
CYP11A1
Uniprot ID:
P00189
Molecular weight:
60333.0
Reactions
27-Hydroxycholesterol + 3 NADPH + 3 Oxygen → 3beta-Hydroxy-5-cholestenoic acid +3 NADP +4 Waterdetails