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Record Information
Version4.0
Creation Date2008-08-13 13:30:12 UTC
Update Date2017-09-27 08:24:48 UTC
HMDB IDHMDB0006846
Secondary Accession Numbers
  • HMDB06846
Metabolite Identification
Common Name24-Methylenelophenol
Description24-Methylenelophenol is involved in the biosynthesis of steroids. 24-Methylenelophenol is converted from 4alpha-Methylfecosterol by cholestenol delta-isomerase [EC:5.3.3.5]. 24-Methylenelophenol is converted to 24-Ethylidene lophenol by 24-methylenesterol C-methyltransferase [EC:2.1.1.143]. 24-Methylenelophenol can also be converted to episterol.
Structure
Thumb
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-olMeSH
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[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol
Traditional Namegramisterol
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
DescriptionThis compound 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:

  Subcellular:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

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
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
Polarizability53.51 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
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, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 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
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB011546
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

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
4a-Methylfecosterol → 24-Methylenelophenoldetails