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Showing Compound Lophenol (FDB012028)

Record Information
Version1.0
Creation date2010-04-08 22:09:57 UTC
Update date2019-11-26 03:06:00 UTC
Primary IDFDB012028
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLophenol
DescriptionConstituent of potato leaves (Solanum tuberosum) 4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-ol is involved in the steroid biosynthesis pathway. In this pathway, 4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol is enzymatically converted to 4-alpha-methyl-5-alpha-cholest-7-en-3-one via the enzyme 3-keto-steroid reductase (EC: 1.1.1.270) and the cofactor NADP(+). This enzyme is responsible for the reduction of the keto group on the C-3 of sterols. (Pathway Commons); ; Steroid biosynthesis is an anabolic metabolic pathway that produces steroids from simple precursors. This pathway is carried out in different ways in animals than in many other organisms, making the pathway a common target for antibiotics and other anti-infective drugs. In addition, steroid metabolism in humans is the target of cholesterol-lowering drugs such as statins. Lophenol is found in many foods, some of which are red bell pepper, yellow bell pepper, potato, and orange bell pepper.
CAS Number481-25-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
4-Methylcholest-7-en-3-olChEBI
MethostenolChEBI
4alpha-Methyl-5alpha-cholest-7-en-3beta-olKegg
4a-Methyl-5a-cholest-7-en-3b-olGenerator
4Α-methyl-5α-cholest-7-en-3β-olGenerator
4-Methylcholest-7-en-3-ol, (3beta,4alpha)-isomerMeSH
4-alpha-Methyl-5-alpha-cholest-7-en-3-beta-olMeSH
4-α-Methyl-5-α-cholest-7-en-3-β-olbiospider
4-a-Methyl-5-a-cholest-7-en-3-b-olbiospider
Cholest-7-en-3-ol, 4-methyl-, (3beta,4alpha,5alpha)-biospider
Lophenoldb_source
Methosteroldb_source
Predicted Properties
PropertyValueSource
Water Solubility3.0e-05 g/LALOGPS
logP7.34ALOGPS
logP7.48ChemAxon
logS-7.1ALOGPS
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
Refractivity125.09 m³·mol⁻¹ChemAxon
Polarizability52.57 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC28H48O
IUPAC name(1R,2S,5S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol
InChI IdentifierInChI=1S/C28H48O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h10,18-20,22-26,29H,7-9,11-17H2,1-6H3/t19-,20+,22-,23+,24+,25+,26+,27-,28+/m1/s1
InChI KeyLMYZQUNLYGJIHI-SPONXPENSA-N
Isomeric 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)CCCC(C)C
Average Molecular Weight400.6801
Monoisotopic Molecular Weight400.370516158
Classification
Description Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • Cholesterol
  • 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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 83.93%; H 12.07%; O 3.99%DFC
Melting PointMp 149-151°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +5 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0ldm-6930100000-54c907bb02d027ff3a672015-03-01View Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0019500000-64e64b40ea31946513042016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0m89-3139100000-39856e46d4ab78dd6ff72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0c29-6339000000-06492203c05ed6a86cdd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-f6492eb67404432e3c042016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-f9d70a523634f6b0b2632016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0159-1009000000-2cda5b422edc920fed652016-08-03View Spectrum
NMR
TypeDescriptionView
ChemSpider ID25994938
ChEMBL IDNot Available
KEGG Compound IDC08825
Pubchem Compound ID50990062
Pubchem Substance IDNot Available
ChEBI ID18378
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB11605
CRC / DFC (Dictionary of Food Compounds) IDHCQ71-I:HCQ72-J
EAFUS IDNot Available
Dr. Duke IDLOPHENOL
BIGG IDNot Available
KNApSAcK IDC00003659
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).