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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-13 13:30:12 UTC
Update Date2022-03-07 02:49:33 UTC
HMDB IDHMDB0006846
Secondary Accession Numbers
  • HMDB06846
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
Data?1582752409
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
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00019 g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+201.33231661259
DarkChem[M-H]-200.79931661259
DeepCCS[M-2H]-247.04830932474
DeepCCS[M+Na]+220.97630932474
AllCCS[M+H]+209.032859911
AllCCS[M+H-H2O]+207.032859911
AllCCS[M+NH4]+210.832859911
AllCCS[M+Na]+211.332859911
AllCCS[M-H]-207.532859911
AllCCS[M+Na-2H]-209.632859911
AllCCS[M+HCOO]-212.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
24-Methylenelophenol[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)C2794.3Standard polar33892256
24-Methylenelophenol[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)C3302.1Standard non polar33892256
24-Methylenelophenol[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)C3328.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
24-Methylenelophenol,1TMS,isomer #1C=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C3396.9Semi standard non polar33892256
24-Methylenelophenol,1TBDMS,isomer #1C=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C3623.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 24-Methylenelophenol GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-0019000000-09dafc9e00fc367295062017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 24-Methylenelophenol GC-MS (1 TMS) - 70eV, Positivesplash10-0avi-2003900000-dd3354b39f35324027292017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 24-Methylenelophenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 24-Methylenelophenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Methylenelophenol 10V, Positive-QTOFsplash10-03dj-1019400000-b4b299deff435bc8fcf72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Methylenelophenol 20V, Positive-QTOFsplash10-03gj-5029100000-9a62b968595bcdbff2392017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Methylenelophenol 40V, Positive-QTOFsplash10-001i-6059000000-364ed46f7bf6bd8b39d42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Methylenelophenol 10V, Negative-QTOFsplash10-03di-0002900000-02f9c4807c829d504e2a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Methylenelophenol 20V, Negative-QTOFsplash10-03di-0004900000-cb8bcbf4d9a655149a7b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Methylenelophenol 40V, Negative-QTOFsplash10-000t-1009000000-101ce75f02d55e1359d92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Methylenelophenol 10V, Positive-QTOFsplash10-03xs-0049400000-92fd5b925b9ac88017ad2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Methylenelophenol 20V, Positive-QTOFsplash10-0ar0-6139000000-565d813c41b7746b5e422021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Methylenelophenol 40V, Positive-QTOFsplash10-0api-9841000000-3c157842f6173f62fa5a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Methylenelophenol 10V, Negative-QTOFsplash10-03di-0000900000-363450e12a0ea926276e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Methylenelophenol 20V, Negative-QTOFsplash10-03di-0000900000-363450e12a0ea926276e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Methylenelophenol 40V, Negative-QTOFsplash10-0a4i-0001900000-eeae5de0a364bd543d4a2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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
Reactions
4alpha-Methylfecosterol → 24-Methylenelophenoldetails