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(3beta,4alpha,5alpha)-4-Methylergosta-8,14,24(28)-trien-3-ol (FDB011216)

Record Information
Version1.0
Creation date2010-04-08 22:09:31 UTC
Update date2019-11-26 03:04:41 UTC
Primary IDFDB011216
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(3beta,4alpha,5alpha)-4-Methylergosta-8,14,24(28)-trien-3-ol
DescriptionConstituent of wheat germ oil (Triticum aestivum) delta 8,14 -Sterol is an intermediate in the biosynthesis of steroids (KEGG ID ; C11508), and is converted from O butusifoliol via the enzyme cytochrome P450, family 51, subfamily A (sterol 14-demethylase)[EC:1.14.13.70]. It is then converted to 4-alpha-methylfecosterol via the enzyme delta14-sterol reductase [EC:1.3.1.70]. (3beta,4alpha,5alpha)-4-Methylergosta-8,14,24(28)-trien-3-ol is found in wheat and cereals and cereal products.
CAS Number74635-33-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0016 g/LALOGPS
logP7ALOGPS
logP6.97ChemAxon
logS-5.4ALOGPS
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
Refractivity130 m³·mol⁻¹ChemAxon
Polarizability52.92 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC29H46O
IUPAC name2,6,15-trimethyl-14-(6-methyl-5-methylideneheptan-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-5-ol
InChI IdentifierInChI=1S/C29H46O/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/h13,18,20-21,23-24,27,30H,3,8-12,14-17H2,1-2,4-7H3
InChI KeyHLAWVOWADPNAGN-UHFFFAOYSA-N
Isomeric SMILESCC(C)C(=C)CCC(C)C1CC=C2C3=C(CCC12C)C1(C)CCC(O)C(C)C1CC3
Average Molecular Weight410.6749
Monoisotopic Molecular Weight410.354866094
Classification
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
  • 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
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 84.81%; H 11.29%; O 3.90%DFC
Melting PointMp 124-126°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data[neutral] lmax 248 () (EtOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-1019500000-046d99a719521520a2212016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053u-5239100000-35e12a7ac241ea6b3d5e2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05o0-7179000000-157b7d71a0b50a4f6cfa2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0002900000-3112227426dc5f73b5982016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0004900000-6302f767a4949cfeabe02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-2009000000-1068ac4ee572fe372b162016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0wmi-0049400000-1531d2bd019304f672932021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-4094100000-0aaf78072ea8778d00612021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0apl-9330000000-b39dac0fa0e9a268cba02021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-84eae2c8ad8ccafd77412021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-a95fd3da7b71ce1eb5be2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1029800000-82608fb297738ae2ff152021-10-21View Spectrum
NMRNot Available
ChemSpider ID391501
ChEMBL IDNot Available
KEGG Compound IDC11508
Pubchem Compound ID443237
Pubchem Substance IDNot Available
ChEBI ID30109
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06928
CRC / DFC (Dictionary of Food Compounds) IDGDZ28-P:GFO31-W
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00007523
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Delta(14)-sterol reductaseTM7SF2O76062
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference