Showing Compound Card for 4alpha-Methylfecosterol (CDB004986)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2)transporters (1) Show 4 proteinsXML
Record Information
Version1.0
Created at2020-04-17 18:57:30 UTC
Updated at2020-12-07 19:11:24 UTC
CannabisDB IDCDB004986
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name4alpha-Methylfecosterol
Description4a-Methylfecosterol belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, 4a-methylfecosterol is considered to be a sterol lipid molecule. 4a-Methylfecosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4alpha-Methylfecosterol is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4alpha-MethylfecosterolHMDB
4 alpha-Methyl-5 alpha-ergosta-8,24(28)-dien-3 beta-olMeSH, HMDB
4a-MethylfecosterolGenerator
4Α-methylfecosterolGenerator, HMDB
(3beta,4alpha,5alpha)-4-Methylergosta-8,24(28)-dien-3-olHMDB
(3β,4α,5α)-4-Methylergosta-8,24(28)-dien-3-olHMDB
24,25-Dihydro-4alpha-methyl-24-methylenezymosterolHMDB
24,25-Dihydro-4α-methyl-24-methylenezymosterolHMDB
4α-MethylfecosterolHMDB
Chemical FormulaC29H48O
Average Molecular Weight412.69
Monoisotopic Molecular Weight412.3705
IUPAC Name(2S,5S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
Traditional Name(2S,5S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
CAS Registry Number17757-07-2
SMILES
[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC(=C)C(C)C
InChI Identifier
InChI=1S/C29H48O/c1-18(2)19(3)8-9-20(4)23-12-13-25-22-10-11-24-21(5)27(30)15-17-29(24,7)26(22)14-16-28(23,25)6/h18,20-21,23-25,27,30H,3,8-17H2,1-2,4-7H3/t20-,21+,23-,24+,25+,27+,28-,29+/m1/s1
InChI KeyQLDNWJOJCDIMKK-XLFBYWHPSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassErgostane steroids
Direct ParentErgosterols and derivatives
Alternative Parents
Substituents
  • Ergosterol-skeleton
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 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:

Biological location:

Source:

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
logP6.64ALOGPS
logP7.37ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)18.96ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity129.15 m³·mol⁻¹ChemAxon
Polarizability53.45 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-MS4alpha-Methylfecosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0032-0019000000-6f8c8cd8a7d225a3048fSpectrum
Predicted GC-MS4alpha-Methylfecosterol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06di-2004900000-8877055f754f2b4ac001Spectrum
Predicted GC-MS4alpha-Methylfecosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-1019400000-5a5687b63ecb5002e1c02017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03gj-5029100000-c5c21496ecefaf5c63792017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-6069000000-672d03b792b2837c18722017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-02f9c4807c829d504e2a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0004900000-cb8bcbf4d9a655149a7b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-1009000000-1ac1e40e61ccf477c8bb2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-363450e12a0ea926276e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000900000-363450e12a0ea926276e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0001900000-02f5c43e79de8082e4872021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xs-0049400000-b3d2f15911af4078abf42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066r-9278100000-93d1a3b37109728cc23e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053u-8930000000-e82c5a534a1740fa5cf32021-09-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Delta(14)-sterol reductaseTM7SF211q13O76062 details
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomeraseEBPXp11.23-p11.22Q15125 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomeraseEBPXp11.23-p11.22Q15125 details
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomeraseEBPXp11.23-p11.22Q15125 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0006845
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012688
KNApSAcK IDC00007524
Chemspider ID167937
KEGG Compound IDC15776
BioCyc IDCPD-4081
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound193524
PDB IDNot Available
ChEBI ID80094
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. 3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase
General function:
Involved in cholestenol delta-isomerase activity
Specific function:
Catalyzes the conversion of Delta(8)-sterols to their corresponding Delta(7)-isomers.
Gene Name:
EBP
Uniprot ID:
Q15125
Molecular weight:
26352.615

Transporters

Enzyme Details
1. 3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase
General function:
Involved in cholestenol delta-isomerase activity
Specific function:
Catalyzes the conversion of Delta(8)-sterols to their corresponding Delta(7)-isomers.
Gene Name:
EBP
Uniprot ID:
Q15125
Molecular weight:
26352.615