Showing metabocard for 4,4-Dimethyl-5a-cholesta-8-en-3b-ol (BMDB0006840)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:26:39 UTC
Update Date2020-05-21 16:27:03 UTC
BMDB IDBMDB0006840
Secondary Accession Numbers
  • BMDB06840
Metabolite Identification
Common Name4,4-Dimethyl-5a-cholesta-8-en-3b-ol
Description4,4-Dimethyl-5a-cholesta-8-en-3b-ol, also known as 3b-hydroxy-4,4-dimethyl-8(9)-cholestene or 4,4-dimethyl-3b-hydroxy-8(9)-cholestene, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, 4,4-dimethyl-5a-cholesta-8-en-3b-ol is considered to be a sterol. Based on a literature review very few articles have been published on 4,4-Dimethyl-5a-cholesta-8-en-3b-ol.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3beta,5alpha)-4,4-Dimethylcholest-8-en-3-olChEBI
3beta-Hydroxy-4,4-dimethyl-8(9)-cholesteneChEBI
3beta-Hydroxy-4,4-dimethylcholest-8(9)-eneChEBI
4,4-Dimethyl-3beta-hydroxy-8(9)-cholesteneChEBI
4,4-Dimethyl-3beta-hydroxycholest-8(9)-eneChEBI
4,4-Dimethyl-5alpha-cholesta-8-en-3beta-olChEBI
4,4-Dimethyl-8-cholesten-3beta-olChEBI
4,4-Dimethylcholest-8(9)-en-3beta-olChEBI
4,4-Dimethylcholesta-8(9)-en-3beta-olChEBI
(3b,5a)-4,4-Dimethylcholest-8-en-3-olGenerator
(3Β,5α)-4,4-dimethylcholest-8-en-3-olGenerator
3b-Hydroxy-4,4-dimethyl-8(9)-cholesteneGenerator
3Β-hydroxy-4,4-dimethyl-8(9)-cholesteneGenerator
3b-Hydroxy-4,4-dimethylcholest-8(9)-eneGenerator
3Β-hydroxy-4,4-dimethylcholest-8(9)-eneGenerator
4,4-Dimethyl-3b-hydroxy-8(9)-cholesteneGenerator
4,4-Dimethyl-3β-hydroxy-8(9)-cholesteneGenerator
4,4-Dimethyl-3b-hydroxycholest-8(9)-eneGenerator
4,4-Dimethyl-3β-hydroxycholest-8(9)-eneGenerator
4,4-Dimethyl-5α-cholesta-8-en-3β-olGenerator
4,4-Dimethyl-8-cholesten-3b-olGenerator
4,4-Dimethyl-8-cholesten-3β-olGenerator
4,4-Dimethylcholest-8(9)-en-3b-olGenerator
4,4-Dimethylcholest-8(9)-en-3β-olGenerator
4,4-Dimethylcholesta-8(9)-en-3b-olGenerator
4,4-Dimethylcholesta-8(9)-en-3β-olGenerator
Chemical FormulaC29H50O
Average Molecular Weight414.7067
Monoisotopic Molecular Weight414.386166222
IUPAC Name(2S,5S,7R,14R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
Traditional Name(2S,5S,7R,14R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
CAS Registry NumberNot Available
SMILES
[H][C@@](C)(CCCC(C)C)[C@@]1([H])CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3
InChI Identifier
InChI=1S/C29H50O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h19-20,22-23,25-26,30H,8-18H2,1-7H3/t20-,22-,23?,25+,26+,28-,29-/m1/s1
InChI KeyFYHRVINOXYETMN-HFPXORMNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Cholesterol-skeleton
  • Cholestane-skeleton
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen 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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.16ALOGPS
logP7.81ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)19.55ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity129.22 m³·mol⁻¹ChemAxon
Polarizability53.67 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, Positivesplash10-01pa-1009000000-a33746936424d40177c0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-3003900000-9e0d5f3612356977101cView 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, Positivesplash10-00kb-0009500000-485fd160c5195d04d4d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mt-4029100000-580315d3fda0dfb48c7dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a70-4229000000-7d9d791bb7b2786a3c80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0001900000-158617c2e43f1a46b58aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0004900000-fdb687d0f9f704a35555View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-1009000000-fd10933f1f8d4206aeb3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-eda302082c5114b2ab3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000900000-eda302082c5114b2ab3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0002900000-130c5bdcc045fd1f8eb1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0004900000-8371c34318fbf5235346View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-090r-9816700000-5ecb58e5630ff095cd7cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pwa-9532000000-f0377ea6ebbd48ef5762View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID19990055
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12070223
PDB IDNot Available
ChEBI ID87044
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. 24-dehydrocholesterol reductase
General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
DHCR24
Uniprot ID:
A6QR14
Molecular weight:
60173.0
Reactions
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADPH → 4,4-Dimethyl-5a-cholesta-8-en-3b-ol + NADPdetails