Showing Compound Card for 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol (CDB005330)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (3) Show 4 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:32:23 UTC
Updated at2020-12-07 19:11:58 UTC
CannabisDB IDCDB005330
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol
Description4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol, also known as 14-demethyllanosterol or 4,4-dimethyl-8,24-cholestadienol, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol is an extremely weak basic (essentially neutral) compound (based on its pKa). 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3beta,5alpha)-4,4-Dimethylcholesta-8,24-dien-3-olHMDB
14-DemethyllanosterolHMDB
4,4-Dimethyl-5 alpha -cholesta-8,24-dien-3 beta -olHMDB
4,4-Dimethyl-5-alpha-cholesta-(8,24)-dien-3-beta-olHMDB
4,4-Dimethyl-5-alpha-cholesta-8,24-dien-3-beta-olHMDB
4,4-Dimethyl-5a-cholesta-8,24-dien-3b-olHMDB
4,4-Dimethyl-5alpha -cholesta-8,24-dien-3-beta -olHMDB
4,4-Dimethyl-5alpha-cholest-7-en-3beta-olHMDB
4,4-Dimethyl-5alpha-cholesta-8,24-dien-3beta-olHMDB
4,4-Dimethyl-8,24-cholestadienolHMDB
4,4-DimethylzymosterolHMDB
4,4-Dimethyl-5-alpha-cholesta-(8,24)-dien-3-beta-ol, (3beta)-isomerHMDB
Chemical FormulaC29H48O
Average Molecular Weight412.69
Monoisotopic Molecular Weight412.3705
IUPAC Name(2S,5S,7R,11R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
Traditional Name(2S,5S,7R,11R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
CAS Registry Number7448-02-4
SMILES
[H][C@@]12CCC([C@H](C)CCC=C(C)C)[C@@]1(C)CCC1=C2CC[C@@]2([H])C(C)(C)[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C29H48O/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/h9,20,22-23,25-26,30H,8,10-18H2,1-7H3/t20-,22?,23+,25+,26+,28-,29-/m1/s1
InChI KeyCHGIKSSZNBCNDW-GKBRUXRCSA-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 DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.14ALOGPS
logP7.41ChemAxon
logS-5.9ALOGPS
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 Count4ChemAxon
Refractivity130.07 m³·mol⁻¹ChemAxon
Polarizability53.05 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-8,24-dien-3-b-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01pk-1009000000-715a7edb03ab16ddaa67Spectrum
Predicted GC-MS4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06di-3003900000-b4d1997a0f59b226076eSpectrum
Predicted GC-MS4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0009500000-5831f1297a9ddaefca1b2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-2139100000-1571d65e1b255cf2e4d32016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0170-3339000000-9b79492ac4a81d9025ec2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-e0f073ba6b1bddb613bc2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0005900000-276fec1a6d98e42e92a12016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002b-1009000000-9afa67f4cfe32f1b2acd2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-363450e12a0ea926276e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000900000-363450e12a0ea926276e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fs-1015900000-96469d6e79efcdc91ee92021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0009700000-803cd9d3863583645c292021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-9527100000-d4f09426d4583ec16d0b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4u-9743000000-3166c978b6fe24ddec4b2021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Delta(14)-sterol reductaseTM7SF211q13O76062 details
Methylsterol monooxygenase 1MSMO14q32-q34Q15800 details
Delta(24)-sterol reductaseDHCR241p32.3Q15392 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Methylsterol monooxygenase 1MSMO14q32-q34Q15800 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001286
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022534
KNApSAcK IDNot Available
Chemspider ID25994967
KEGG Compound IDC05108
BioCyc IDNot Available
BiGG ID45128
Wikipedia LinkNot Available
METLIN ID6135
PubChem Compound50990081
PDB IDNot Available
ChEBI ID18364
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Delta(14)-sterol reductase
General function:
Involved in delta14-sterol reductase activity
Specific function:
Involved in the conversion of lanosterol to cholesterol.
Gene Name:
TM7SF2
Uniprot ID:
O76062
Molecular weight:
46405.345
Enzyme Details
2. Methylsterol monooxygenase 1
General function:
Involved in iron ion binding
Specific function:
Not Available
Gene Name:
MSMO1
Uniprot ID:
Q15800
Molecular weight:
19470.325
Enzyme Details
3. 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