Showing metabocard for (24R)-Cholest-5-ene-3-beta,7-alpha,24-triol (BMDB0011644)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 18:22:13 UTC
Update Date2020-05-21 16:28:49 UTC
BMDB IDBMDB0011644
Secondary Accession Numbers
  • BMDB11644
Metabolite Identification
Common Name(24R)-Cholest-5-ene-3-beta,7-alpha,24-triol
Description(24R)-Cholest-5-ene-3-beta,7-alpha,24-triol , also known as 5a-cholesta-7,24-dien-3-b-ol, 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 (24R)-Cholest-5-ene-3-beta,7-alpha,24-triol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(24R)-Cholest-5-ene-3-b,7-a,24-triolGenerator
(24R)-Cholest-5-ene-3-β,7-α,24-triolGenerator
(24R)-Cholest-5-ene 3-b,7-a,24-triolHMDB
(24R)-Cholest-5-ene-3beta,7alpha,24-triolHMDB
5a-Cholesta-7,24-dien-3-b-olHMDB
5a-Cholesta-7,24-dien-3-beta-olHMDB
Chemical FormulaC27H46O3
Average Molecular Weight418.6523
Monoisotopic Molecular Weight418.344695338
IUPAC Name(1S,2R,5S,9S,10S,11S,15R)-14-[(2R,5R)-5-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol
Traditional Name(1S,2R,5S,9S,10S,11S,15R)-14-[(2R,5R)-5-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol
CAS Registry NumberNot Available
SMILES
[H][C@@]12CCC([C@H](C)CC[C@@H](O)C(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C27H46O3/c1-16(2)23(29)9-6-17(3)20-7-8-21-25-22(11-13-27(20,21)5)26(4)12-10-19(28)14-18(26)15-24(25)30/h15-17,19-25,28-30H,6-14H2,1-5H3/t17-,19+,20?,21+,22+,23-,24-,25+,26+,27-/m1/s1
InChI KeyZNCHPOYZMVVJCK-DPFMVWRKSA-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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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
logP4.28ALOGPS
logP4.65ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.66ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity123.65 m³·mol⁻¹ChemAxon
Polarizability51.47 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-1239400000-cd1b8c75eaf66591d8c2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00xu-2110149000-138cf2097993192ea364View 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, Positivesplash10-0ue9-0007900000-17814845dbf0bec54cfdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-3009400000-fd95622ed3f4f1fae1c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-5029000000-70e1fb26560a91668d82View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0005900000-a892257c0a1e6d75d1d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-0009500000-66d60259ffcab13684b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fl9-7009200000-99af00a0dfd9097d149bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-f2cb6399034352e924c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1002900000-b6143eba8eae9ed9668bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014j-3019800000-4bfcf5c6acaa256d7599View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zgi-0308900000-66129b219db1313f7273View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-3329100000-91ec216cab7fcf837bafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0adi-3943000000-12a20d116574d822ddefView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0011644
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028340
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481010
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Lanosterol 14-alpha demethylase
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
A cytochrome P450 monooxygenase involved in sterol biosynthesis. Catalyzes 14-alpha demethylation of lanosterol and 24,25-dihydrolanosterol likely through sequential oxidative conversion of 14-alpha methyl group to hydroxymethyl, then to carboxylaldehyde, followed by the formation of the delta 14,15 double bond in the sterol core and concomitant release of formic acid. Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase).
Gene Name:
CYP51A1
Uniprot ID:
Q4PJW3
Molecular weight:
56596.0
Reactions
24-Hydroxycholesterol + NADPH + Oxygen → (24R)-Cholest-5-ene-3-beta,7-alpha,24-triol + NADP + Waterdetails