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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-08-13 11:06:51 UTC
Update Date2022-03-07 02:49:33 UTC
HMDB IDHMDB0006840
Secondary Accession Numbers
  • HMDB06840
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
Data?1582752409
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
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00015 g/LALOGPS
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+201.06731661259
DarkChem[M-H]-202.85531661259
DeepCCS[M-2H]-242.75530932474
DeepCCS[M+Na]+217.41230932474
AllCCS[M+H]+210.732859911
AllCCS[M+H-H2O]+208.832859911
AllCCS[M+NH4]+212.532859911
AllCCS[M+Na]+213.032859911
AllCCS[M-H]-207.732859911
AllCCS[M+Na-2H]-210.032859911
AllCCS[M+HCOO]-212.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4,4-Dimethyl-5a-cholesta-8-en-3b-ol[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])CC33047.5Standard polar33892256
4,4-Dimethyl-5a-cholesta-8-en-3b-ol[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])CC33293.9Standard non polar33892256
4,4-Dimethyl-5a-cholesta-8-en-3b-ol[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])CC33268.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4,4-Dimethyl-5a-cholesta-8-en-3b-ol,1TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)C(C)(C)[C@@H]1CC33255.7Semi standard non polar33892256
4,4-Dimethyl-5a-cholesta-8-en-3b-ol,1TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)C(C)(C)[C@@H]1CC33473.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4,4-Dimethyl-5a-cholesta-8-en-3b-ol GC-MS (Non-derivatized) - 70eV, Positivesplash10-01pa-1009000000-a33746936424d40177c02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4-Dimethyl-5a-cholesta-8-en-3b-ol GC-MS (1 TMS) - 70eV, Positivesplash10-00di-3003900000-9e0d5f3612356977101c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4-Dimethyl-5a-cholesta-8-en-3b-ol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-Dimethyl-5a-cholesta-8-en-3b-ol 10V, Positive-QTOFsplash10-00kb-0009500000-485fd160c5195d04d4d42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-Dimethyl-5a-cholesta-8-en-3b-ol 20V, Positive-QTOFsplash10-05mt-4029100000-580315d3fda0dfb48c7d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-Dimethyl-5a-cholesta-8-en-3b-ol 40V, Positive-QTOFsplash10-0a70-4229000000-7d9d791bb7b2786a3c802017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-Dimethyl-5a-cholesta-8-en-3b-ol 10V, Negative-QTOFsplash10-03di-0001900000-158617c2e43f1a46b58a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-Dimethyl-5a-cholesta-8-en-3b-ol 20V, Negative-QTOFsplash10-03di-0004900000-fdb687d0f9f704a355552017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-Dimethyl-5a-cholesta-8-en-3b-ol 40V, Negative-QTOFsplash10-000t-1009000000-fd10933f1f8d4206aeb32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-Dimethyl-5a-cholesta-8-en-3b-ol 10V, Negative-QTOFsplash10-03di-0000900000-eda302082c5114b2ab3a2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-Dimethyl-5a-cholesta-8-en-3b-ol 20V, Negative-QTOFsplash10-03di-0000900000-eda302082c5114b2ab3a2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-Dimethyl-5a-cholesta-8-en-3b-ol 40V, Negative-QTOFsplash10-03di-0002900000-130c5bdcc045fd1f8eb12021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-Dimethyl-5a-cholesta-8-en-3b-ol 10V, Positive-QTOFsplash10-014i-0004900000-8371c34318fbf52353462021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-Dimethyl-5a-cholesta-8-en-3b-ol 20V, Positive-QTOFsplash10-090r-9816700000-5ecb58e5630ff095cd7c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4-Dimethyl-5a-cholesta-8-en-3b-ol 40V, Positive-QTOFsplash10-0pwa-9532000000-f0377ea6ebbd48ef57622021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.000121 uMNewborn (0-30 days old)Not Specified
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Energy production and conversion
Specific function:
Catalyzes the reduction of the delta-24 double bond of sterol intermediates. Protects cells from oxidative stress by reducing caspase 3 activity during apoptosis induced by oxidative stress. Also protects against amyloid-beta peptide-induced apoptosis.
Gene Name:
DHCR24
Uniprot ID:
Q15392
Molecular weight:
60100.805
Reactions
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADPH + Hydrogen Ion → 4,4-Dimethyl-5a-cholesta-8-en-3b-ol + NADPdetails