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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-13 13:21:54 UTC
Update Date2021-09-14 15:19:02 UTC
HMDB IDHMDB0006845
Secondary Accession Numbers
  • HMDB0006925
  • HMDB06845
  • HMDB06925
Metabolite Identification
Common Name4alpha-Methylfecosterol
Description4alpha-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, 4alpha-methylfecosterol is considered to be a sterol lipid molecule. 4alpha-Methylfecosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4alpha-Methylfecosterol is involved in the biosynthesis of steroids. 4alpha-Methylfecosterol is converted from delta8,14-sterol by delta14-sterol reductase (EC 1.3.1.70). 4alpha-Methylfecosterol is converted into 24-methylenelophenol by cholestenol delta-isomerase (EC 5.3.3.5).
Structure
Data?1586456399
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 Weight412.6908
Monoisotopic Molecular Weight412.370516158
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

Biological location

Source

Route of exposure

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 Solubility0.00069 g/LALOGPS
logP10(6.64) g/LALOGPS
logP10(7.37) g/LChemAxon
logS10(-5.8) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+202.84431661259
DarkChem[M-H]-200.24831661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4alpha-Methylfecosterol[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)C2637.5Standard polar33892256
4alpha-Methylfecosterol[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)C3279.2Standard non polar33892256
4alpha-Methylfecosterol[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)C3253.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4alpha-Methylfecosterol,1TMS,isomer #1C=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)[C@@H](C)[C@@H]1CC3)C(C)C3306.2Semi standard non polar33892256
4alpha-Methylfecosterol,1TBDMS,isomer #1C=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)[C@@H]1CC3)C(C)C3545.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4alpha-Methylfecosterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0032-0019000000-6f8c8cd8a7d225a3048f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4alpha-Methylfecosterol GC-MS (1 TMS) - 70eV, Positivesplash10-06di-2004900000-8877055f754f2b4ac0012017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4alpha-Methylfecosterol 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 - 4alpha-Methylfecosterol 10V, Positive-QTOFsplash10-03dj-1019400000-5a5687b63ecb5002e1c02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Methylfecosterol 20V, Positive-QTOFsplash10-03gj-5029100000-c5c21496ecefaf5c63792017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Methylfecosterol 40V, Positive-QTOFsplash10-001i-6069000000-672d03b792b2837c18722017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Methylfecosterol 10V, Negative-QTOFsplash10-03di-0002900000-02f9c4807c829d504e2a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Methylfecosterol 20V, Negative-QTOFsplash10-03di-0004900000-cb8bcbf4d9a655149a7b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Methylfecosterol 40V, Negative-QTOFsplash10-000t-1009000000-1ac1e40e61ccf477c8bb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Methylfecosterol 10V, Negative-QTOFsplash10-03di-0000900000-363450e12a0ea926276e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Methylfecosterol 20V, Negative-QTOFsplash10-03di-0000900000-363450e12a0ea926276e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Methylfecosterol 40V, Negative-QTOFsplash10-0a4i-0001900000-02f5c43e79de8082e4872021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Methylfecosterol 10V, Positive-QTOFsplash10-03xs-0049400000-b3d2f15911af4078abf42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Methylfecosterol 20V, Positive-QTOFsplash10-066r-9278100000-93d1a3b37109728cc23e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-Methylfecosterol 40V, Positive-QTOFsplash10-053u-8930000000-e82c5a534a1740fa5cf32021-09-22Wishart 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 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
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 delta14-sterol reductase activity
Specific function:
Involved in the conversion of lanosterol to cholesterol.
Gene Name:
TM7SF2
Uniprot ID:
O76062
Molecular weight:
46405.345
Reactions
delta8,14-Sterol + NADPH + Hydrogen Ion → 4alpha-Methylfecosterol + NADPdetails
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