Showing Compound Card for 3-Keto-4-methylzymosterol (CDB005341)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:33:30 UTC
Updated at2020-12-07 19:11:59 UTC
CannabisDB IDCDB005341
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name3-Keto-4-methylzymosterol
Description3-Keto-4-methylzymosterol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. 3-Keto-4-methylzymosterol is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Keto-4-methylzymosterol is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5a)-4-Methylcholesta-8,24-dien-3-oneHMDB
(5alpha)-4-Methylcholesta-8,24-dien-3-oneHMDB
3-Dehydro-4-methylzymosterolHMDB
4-Methyl-5a-cholesta-8,24-dien-3-oneHMDB
4-Methyl-5alpha-cholesta-8,24-dien-3-oneHMDB
Chemical FormulaC28H44O
Average Molecular Weight396.65
Monoisotopic Molecular Weight396.3392
IUPAC Name(2S,15R)-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-one
Traditional Name(2S,15R)-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-one
CAS Registry NumberNot Available
SMILES
C[C@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)C(C)C1CC3
InChI Identifier
InChI=1S/C28H44O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h8,19-20,22-24H,7,9-17H2,1-6H3/t19-,20?,22?,23?,24?,27-,28+/m1/s1
InChI KeyDBPZYKHQDWKORQ-JQDPPCHWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • Oxosteroid
  • 3-oxosteroid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

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
logP7.22ALOGPS
logP7.41ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)19.83ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity124.75 m³·mol⁻¹ChemAxon
Polarizability50.26 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-MS3-Keto-4-methylzymosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-02au-2019000000-5173500b11e18ce35b3bSpectrum
Predicted GC-MS3-Keto-4-methylzymosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Keto-4-methylzymosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-00d160bd3605d4c8b8462016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00pv-1119000000-e5a9171fb6049ee634312016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015i-2119000000-6b021eb86e51393d97982016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-e91a27c7e4df70239c242016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-766b7ce92b3bc6de20e72016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-3009000000-b4ba7e91fae9c3e7a4ba2016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0019000000-f87374bf70bdfa4a699f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ap0-3259000000-e97d8860c45e22b2a89d2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-6951000000-99c4649de525703330a72021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-2f6aa9af0bd8878fb6c62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-2f6aa9af0bd8878fb6c62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-0009000000-3e9131f464f27a3024a52021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Sterol-4-alpha-carboxylate 3-dehydrogenase, decarboxylatingNSDHLXq28Q15738 details
3-keto-steroid reductaseHSD17B71q23P56937 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0006838
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB024112
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC15816
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477900
PDB IDNot Available
ChEBI ID505093
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Sterol-4-alpha-carboxylate 3-dehydrogenase, decarboxylating
General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
Not Available
Gene Name:
NSDHL
Uniprot ID:
Q15738
Molecular weight:
41899.99
Enzyme Details
2. 3-keto-steroid reductase
General function:
Involved in oxidoreductase activity
Specific function:
Responsible for the reduction of the keto group on the C-3 of sterols.
Gene Name:
HSD17B7
Uniprot ID:
P56937
Molecular weight:
38205.77