Showing Compound Card for 4,4-Dimethyl-5a-cholesta-8-en-3b-ol (CDB005331)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Created at2020-04-17 19:32:29 UTC
Updated at2020-12-07 19:11:58 UTC
CannabisDB IDCDB005331
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name4,4-Dimethyl-5a-cholesta-8-en-3b-ol
DescriptionTetrahydrofolyl-[Glu](n), also known as THF-L-glutamic acid or THF-polyglutamate, belongs to the class of organic compounds known as tetrahydrofolic acids and derivatives. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit (or a derivative thereof) . Tetrahydrofolyl-[Glu](n) is a strong basic compound (based on its pKa). Within humans, tetrahydrofolyl-[glu](N) participates in a number of enzymatic reactions. In particular, tetrahydrofolyl-[glu](N) can be biosynthesized from tetrahydrofolyl-[glu](2) and L-glutamic acid; which is mediated by the enzyme folylpolyglutamate synthase. In addition, tetrahydrofolyl-[glu](N) can be converted into tetrahydrofolyl-[glu](2) and L-glutamic acid through its interaction with the enzyme Gamma-glutamyl hydrolase. In humans, tetrahydrofolyl-[glu](N) is involved in the metabolic disorder called the methylenetetrahydrofolate reductase deficiency (mthfrd) pathway. Sample structure image shows the case when n=3. 4,4-Dimethyl-5a-cholesta-8-en-3b-ol is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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 Weight414.71
Monoisotopic Molecular Weight414.3862
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS4,4-Dimethyl-5a-cholesta-8-en-3b-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01pa-1009000000-a33746936424d40177c0Spectrum
Predicted GC-MS4,4-Dimethyl-5a-cholesta-8-en-3b-ol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-3003900000-9e0d5f3612356977101cSpectrum
Predicted GC-MS4,4-Dimethyl-5a-cholesta-8-en-3b-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0009500000-485fd160c5195d04d4d42017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mt-4029100000-580315d3fda0dfb48c7d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a70-4229000000-7d9d791bb7b2786a3c802017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0001900000-158617c2e43f1a46b58a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0004900000-fdb687d0f9f704a355552017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-1009000000-fd10933f1f8d4206aeb32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-eda302082c5114b2ab3a2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000900000-eda302082c5114b2ab3a2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0002900000-130c5bdcc045fd1f8eb12021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0004900000-8371c34318fbf52353462021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-090r-9816700000-5ecb58e5630ff095cd7c2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pwa-9532000000-f0377ea6ebbd48ef57622021-09-25View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Delta(24)-sterol reductaseDHCR241p32.3Q15392 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
General ReferencesNot Available

Enzymes

Enzyme Details
1. Delta(24)-sterol reductase
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