Showing Compound Card for 24-Methylenelophenol (CDB005335)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1)transporters (1) Show 3 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:32:53 UTC
Updated at2020-12-07 19:11:58 UTC
CannabisDB IDCDB005335
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name24-Methylenelophenol
Description24-Methylenelophenol, also known as 4.alpha-methylepisterol or gramisterin, 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, 24-methylenelophenol is considered to be a sterol lipid molecule. 24-Methylenelophenol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 24-Methylenelophenol is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
24-Methylene lophenolChEBI
4-alpha-Methyl-5-alpha-ergosta-7,24-dien-3-beta-olChEBI
4-a-Methyl-5-a-ergosta-7,24-dien-3-b-olGenerator
4-Α-methyl-5-α-ergosta-7,24-dien-3-β-olGenerator
(3beta,4alpha,5alpha)- 4-Methyl-ergosta-7,24(28)-dien-3-olHMDB
24-Methylene-lophenolHMDB
4.alpha-methylepisterolHMDB
4Alpha.-methyl-24-methylene-5alpha-cholest-7-en-3beta-olHMDB
4Alpha.-methyl-5alpha-ergosta-7,24(28)-dien-3beta.-olHMDB
GramisterinHMDB
GramisterolHMDB
4-Methyl-5-ergosta-7,24(24')-diene-3-olHMDB
(3beta,4alpha,5alpha)-4-Methylergosta-7,24(28)-dien-3-olHMDB
(3Β,4α,5α)-4-methylergosta-7,24(28)-dien-3-olHMDB
4alpha-Methyl-24-methylene-5alpha-cholest-7-en-3beta-olHMDB
4alpha-MethylepisterolHMDB
4Α-methyl-24-methylene-5α-cholest-7-en-3β-olHMDB
4Α-methylepisterolHMDB
24-MethylenelophenolMeSH
Chemical FormulaC29H48O
Average Molecular Weight412.69
Monoisotopic Molecular Weight412.3705
IUPAC Name(1R,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-9-en-5-ol
Traditional Name(1R,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-9-en-5-ol
CAS Registry Number1176-52-9
SMILES
[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])[C@H](C)[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[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/h10,18,20-21,23-27,30H,3,8-9,11-17H2,1-2,4-7H3/t20-,21+,23-,24+,25+,26+,27+,28-,29+/m1/s1
InChI KeyRSMKYRDCCSNYFM-AAGDOFLISA-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
  • 3-hydroxy-delta-7-steroid
  • Delta-7-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:

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
logP6.99ALOGPS
logP7.42ChemAxon
logS-6.3ALOGPS
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
Refractivity129.41 m³·mol⁻¹ChemAxon
Polarizability53.46 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-MS24-Methylenelophenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001j-0019000000-09dafc9e00fc36729506Spectrum
Predicted GC-MS24-Methylenelophenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0avi-2003900000-dd3354b39f3532402729Spectrum
Predicted GC-MS24-Methylenelophenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS24-Methylenelophenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-1019400000-b4b299deff435bc8fcf72017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03gj-5029100000-9a62b968595bcdbff2392017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-6059000000-364ed46f7bf6bd8b39d42017-09-01View 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-1009000000-101ce75f02d55e1359d92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xs-0049400000-92fd5b925b9ac88017ad2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ar0-6139000000-565d813c41b7746b5e422021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0api-9841000000-3c157842f6173f62fa5a2021-09-23View 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, Negativesplash10-0a4i-0001900000-eeae5de0a364bd543d4a2021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
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 IDHMDB0006846
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011547
KNApSAcK IDC00007320
Chemspider ID4446733
KEGG Compound IDC11522
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283640
PDB IDNot Available
ChEBI ID29107
References
General ReferencesNot Available

Enzymes

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

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