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Showing Compound Fenugrin A (FDB007353)

Record Information
Version1.0
Creation date2010-04-08 22:07:34 UTC
Update date2019-11-26 03:01:37 UTC
Primary IDFDB007353
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameFenugrin A
DescriptionFenugrin a, also known as sumithrin or phenothrin, (1s-cis)-isomer, is a member of the class of compounds known as pyrethroids. Pyrethroids are organic compounds similar to the pyrethrins. Some pyrethroids containing a chrysanthemic acid esterified with a cyclopentenone (pyrethrins), or with a phenoxybenzyl group. Fenugrin a is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Fenugrin a can be found in fenugreek, which makes fenugrin a a potential biomarker for the consumption of this food product. Fenugrin a is a non-carcinogenic (not listed by IARC) potentially toxic compound. Following oral exposure, the treatment is symptomatic and supportive and includes monitoring for the development of hypersensitivity reactions with respiratory distress. Provide adequate airway management when needed. Gastric decontamination is usually not required unless the pyrethrin product is combined with a hydrocarbon. Following inhalation exposure, move patient to fresh air. monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist, the patient should be seen in a health care facility. If the contamination occurs through dermal exposure, Remove contaminated clothing and wash exposed area thoroughly with soap and water. A physician may need to examine the area if irritation or pain persists. Vitamin E topical application is highly effective in relieving parenthesis (L363) (T3DB).
CAS Number26002-80-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.002 g/LALOGPS
logP6.42ALOGPS
logP5.57ChemAxon
logS-5.2ALOGPS
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity103.84 m³·mol⁻¹ChemAxon
Polarizability39.2 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC23H26O3
IUPAC name(3-phenoxyphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate
InChI IdentifierInChI=1S/C23H26O3/c1-16(2)13-20-21(23(20,3)4)22(24)25-15-17-9-8-12-19(14-17)26-18-10-6-5-7-11-18/h5-14,20-21H,15H2,1-4H3
InChI KeySBNFWQZLDJGRLK-UHFFFAOYSA-N
Isomeric SMILESCC(C)=CC1C(C(=O)OCC2=CC=CC(OC3=CC=CC=C3)=C2)C1(C)C
Average Molecular Weight350.4507
Monoisotopic Molecular Weight350.188194698
Classification
Description Belongs to the class of organic compounds known as pyrethroids. These are organic compounds similar to the pyrethrins. Some pyrethroids containing a chrysanthemic acid esterified with a cyclopentenone (pyrethrins), or with a phenoxybenzyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentPyrethroids
Alternative Parents
Substituents
  • Pyrethroid skeleton
  • Diphenylether
  • Diaryl ether
  • Aromatic monoterpenoid
  • Benzyloxycarbonyl
  • Monocyclic monoterpenoid
  • Monoterpenoid
  • Phenoxy compound
  • Phenol ether
  • Monocyclic benzene moiety
  • Cyclopropanecarboxylic acid or derivatives
  • Benzenoid
  • Carboxylic acid ester
  • Ether
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00e9-5900000000-82828ceb9c78ca7154052014-09-20View Spectrum
Predicted GC-MSFenugrin A, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFenugrin A, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFenugrin A, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFenugrin A, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0a4i-0009000000-40229bc9204047a906962021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0a4i-0009000000-ef289d9b6c43e9ffbab12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0002-0009000000-aaf1dcdf1335b088a86b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a4i-0009000000-b8fdf60d2da1b9af6def2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0a6u-0900000000-c9855a3f9fc537fb0bcf2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-0a4l-0900000000-efa2e4a7c20189b908ea2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0409000000-29f91143368a5e1636382016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-3935000000-1f5ba52cfd1331e3c8292016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pvi-7900000000-a7c057d4e94614b05bf62016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0109000000-2146ad06bc95b25bf4422016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-2809000000-986cbdb101e42868e61b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-8f041a7fa0db67d9ea242016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f7k-2794000000-e3308d4427a553ee9e332021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2913000000-92692d151e0539f88ca02021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-7900000000-c59f160f7452c1b7d5452021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0309000000-1a857626b5331003790e2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0901000000-e1b9792b83ff015d64f72021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9322000000-254c9ac19a5f51b0b4b22021-10-12View Spectrum
NMR
TypeDescriptionView
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDFENUGRIN-A
BIGG IDNot Available
KNApSAcK IDNot Available
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
Processing...
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).