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Moupinamide (FDB000432)

Record Information
Version1.0
Creation date2010-04-08 22:04:34 UTC
Update date2020-09-17 15:33:07 UTC
Primary IDFDB000432
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMoupinamide
DescriptionMoupinamide, also known as Alfrutamide or N-feruloyltyramine or N-trans-feruloyltyramine (NTF), belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. It is also classified as a phenylpropanoid amide. Phenylpropanoids consist of a six-carbon, aromatic phenyl group and a three-carbon propene tail of coumaric acid, which is the central intermediate in phenylpropanoid biosynthesis. A phenylpropanoid amide has an amide group incorporated into its propanoid chain. There are two known isomers of N-Feruloyltyramine, N-trans-Feruloyltyramine and N-cis-Feruloyltyramine. Moupinamide is a largely neutral molecule, that is somewhat insoluble in water. It exists as a pale yellow oil. Moupinamide or N-trans-Feruloyltyramine is found in black and white peppers. N-cis-Feruloyltyramine has been identified in yellow bell peppers, red bell peppers and in a lower concentration in orange bell peppers, green bell peppers, celery leaves, hyssops, quinoa, agars, and oxheart cabbages. Moupinamide is an inhibitor of COX 1 and COX 2 and has potential antioxidant properties (PMID: 19807156)
CAS Number66648-43-9
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP2.46ALOGPS
logP3.05ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)4.41ChemAxon
pKa (Strongest Basic)6.38ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area82.28 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity90.09 m³·mol⁻¹ChemAxon
Polarizability34.56 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H19NO4
IUPAC name(Z,2E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid
InChI IdentifierInChI=1S/C18H19NO4/c1-23-17-12-14(4-8-16(17)21)5-9-18(22)19-11-10-13-2-6-15(20)7-3-13/h2-9,12,20-21H,10-11H2,1H3,(H,19,22)/b9-5+
InChI KeyNPNNKDMSXVRADT-WEVVVXLNSA-N
Isomeric SMILESCOC1=CC(\C=C\C(=O)NCCC2=CC=C(O)C=C2)=CC=C1O
Average Molecular Weight313.3478
Monoisotopic Molecular Weight313.131408101
Classification
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Styrene
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Carboximidic acid
  • Carboximidic acid derivative
  • Ether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 69.00%; H 6.11%; N 4.47%; O 20.42%DFC
Melting PointMp 144.5-145°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSMoupinamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4j-0930000000-0d34a7b54bbeaebc282bSpectrum
Predicted GC-MSMoupinamide, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-9433600000-1e204cd575b97a4b0e8eSpectrum
Predicted GC-MSMoupinamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMoupinamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - , negativesplash10-03di-0509000000-7a8a88d076bfbf1cf48c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-00ba-1900000000-1acd727ab1a27d74943c2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01p9-0902000000-35cbd3fbcb8058d643292016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-0900000000-714a65fcbd5aa8249bea2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0avs-3900000000-cdd8344e1c4c188399fb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0419000000-87271f4c26fc442256b32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08ic-0922000000-64a362d838af2e86e0dc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-3900000000-b725e376ed0d4ee8b4052016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0209000000-c1a4d6d9de34cccce22b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-0913000000-efa7c33a7ab2898ad0e32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-2920000000-c1af345555bf57620ee12021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-5cd9c8e6e0b2900b51af2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ri-0902000000-10d6192946f54c2146a72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-1920000000-bbb470c57468688aaedc2021-09-22View Spectrum
NMRNot Available
ChemSpider ID4444168
ChEMBL IDCHEMBL206555
KEGG Compound IDC02717
Pubchem Compound ID5280537
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB29365
CRC / DFC (Dictionary of Food Compounds) IDBCB62-V:BCB61-U
EAFUS IDNot Available
Dr. Duke IDN-TRANS-FERULOYL-TYRAMINE
BIGG IDNot Available
KNApSAcK IDC00025334
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.