Showing metabocard for 24-Methylenelophenol (BMDB0006846)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:26:44 UTC
Update Date2020-04-22 15:18:49 UTC
BMDB IDBMDB0006846
Secondary Accession Numbers
  • BMDB06846
Metabolite 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.
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 Weight412.6908
Monoisotopic Molecular Weight412.370516158
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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-0019000000-09dafc9e00fc36729506View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0avi-2003900000-dd3354b39f3532402729View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-1019400000-b4b299deff435bc8fcf7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03gj-5029100000-9a62b968595bcdbff239View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-6059000000-364ed46f7bf6bd8b39d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-02f9c4807c829d504e2aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0004900000-cb8bcbf4d9a655149a7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-1009000000-101ce75f02d55e1359d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xs-0049400000-92fd5b925b9ac88017adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ar0-6139000000-565d813c41b7746b5e42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0api-9841000000-3c157842f6173f62fa5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-363450e12a0ea926276eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000900000-363450e12a0ea926276eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0001900000-eeae5de0a364bd543d4aView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006846
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available