Showing metabocard for 7-a,27-dihydroxycholesterol (BMDB0006281)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:21:11 UTC
Update Date2020-05-21 16:28:49 UTC
BMDB IDBMDB0006281
Secondary Accession Numbers
  • BMDB06281
Metabolite Identification
Common Name7-a,27-dihydroxycholesterol
Description7-a,27-Dihydroxycholesterol, also known as cholest-5-ene-3b,7a,26-triol, belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. Thus, 7-a,27-dihydroxycholesterol is considered to be a bile acid lipid molecule. 7-a,27-Dihydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
5-Cholestene-3beta,7alpha,26-triolChEBI
7-alpha,27-DihydroxycholesterolChEBI
Cholest-5-ene-3beta,7alpha,26-triolChEBI
Cholest-5-ene-3beta,7alpha,27-triolChEBI
5-Cholestene-3b,7a,26-triolGenerator
5-Cholestene-3β,7α,26-triolGenerator
7-Α,27-dihydroxycholesterolGenerator
Cholest-5-ene-3b,7a,26-triolGenerator
Cholest-5-ene-3β,7α,26-triolGenerator
Cholest-5-ene-3b,7a,27-triolGenerator
Cholest-5-ene-3β,7α,27-triolGenerator
7alpha,26-DihydroxycholesterolHMDB
7alpha,27-DihydroxycholesterolHMDB
Cholest-5-ene-3,7,27-triolHMDB
Cholest-5-ene-3- b,7-a,27-triolHMDB
Cholest-5-ene-3-b,7-a,27-triolHMDB
Cholest-5-ene-3-beta,7-alpha,27-triolHMDB
Chemical FormulaC27H46O3
Average Molecular Weight418.6523
Monoisotopic Molecular Weight418.344695338
IUPAC Name(1S,2R,5S,9S,10S,11S,14R,15R)-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol
Traditional Name7α,27-dihydroxycholesterol
CAS Registry Number4725-24-0
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)CO
InChI Identifier
InChI=1S/C27H46O3/c1-17(16-28)6-5-7-18(2)21-8-9-22-25-23(11-13-27(21,22)4)26(3)12-10-20(29)14-19(26)15-24(25)30/h15,17-18,20-25,28-30H,5-14,16H2,1-4H3/t17?,18-,20+,21-,22+,23+,24-,25+,26+,27-/m1/s1
InChI KeyRXMHNAKZMGJANZ-DTTSCKGMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTrihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • 26-hydroxysteroid
  • Trihydroxy bile acid, alcohol, or derivatives
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 7-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Fatty alcohol
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Primary alcohol
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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
logP4.67ALOGPS
logP4.6ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)17.42ChemAxon
pKa (Strongest Basic)-0.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity123.91 m³·mol⁻¹ChemAxon
Polarizability52.19 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, Positivesplash10-0udi-0139300000-221e3200779e0697d017View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00xr-1310149000-0a3195294de24630bcb5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0006900000-c1354f70aeba87e8bddfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-1009300000-a1e89f6c04fc2d2865d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-062c-3029000000-d0d93103295de6ed3d2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0006900000-6b334d55dd76faff4df8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0009400000-c2983b5dbb3cbfbf357eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dr-2009100000-2e80feb58d681f70a6f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0002900000-a0815d1227c30636020cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0003900000-810b115febb00f469d25View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0003900000-558c2f025f3c29e2e952View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-1202900000-bd6f4c8c658841ee2d20View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-6359400000-afbc03ffc36e1b423024View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abi-7950000000-0145ada702a586b3b664View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006281
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023875
KNApSAcK IDNot Available
Chemspider ID389810
KEGG Compound IDC06341
BioCyc IDNot Available
BiGG ID48023
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440985
PDB IDNot Available
ChEBI ID18431
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Prostacyclin synthase
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
27-Hydroxycholesterol + NADPH + Oxygen → 7-a,27-dihydroxycholesterol + NADP + Waterdetails
Enzyme Details
2. 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids.
Gene Name:
HSD3B
Uniprot ID:
P14893
Molecular weight:
42220.0
Reactions
7-a,27-dihydroxycholesterol + NADP → 7 alpha,26-Dihydroxy-4-cholesten-3-one + NADPHdetails