Showing Compound Card for Moupinamide (CDB000361)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (3) Show 7 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:32:55 UTC
Updated at2022-07-15 15:31:39 UTC
CannabisDB IDCDB000361
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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. N-trans-feruloyltyramine (Moupinamide) is one of the major phenylpropanoid amides that have been identified in the cannabis plant (PMID:6991645 ). Moupinamide is an inhibitor of COX 1 and COX 2 and has potential antioxidant properties (PMID: 19807156 )
Structure
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MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
N-[(e)-Feruloyl]tyramineChEBI
trans-N-FeruloyltyramineChEBI
Feruloyltyramine, (Z)-isomerMeSH
N-FeruloyltyramineMeSH
FeruloyltyramineMeSH
Feruloyltyramine, (e)-isomerMeSH
(2,3)trans-N-(P-Hydroxyphenethyl)ferulamideHMDB
N-trans-FeruloyltyramineHMDB
MoupinamideChEBI
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidate HMDB
(2,3) trans-N-(P-Hydroxyphenethyl)ferulamide HMDB
(2E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-2-propenamideHMDB
(2E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamideHMDB
NFTHMDB
AlfrutamideHMDB
3-(4-hydroxy-3-methoxyphenyl)-N-(2-(4-hydroxyphenyl)ethyl)-2-PropenamideHMDB
Chemical FormulaC18H19NO4
Average Molecular Weight313.35
Monoisotopic Molecular Weight313.1314
IUPAC Name(Z,2E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid
Traditional Name(Z,2E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid
CAS Registry Number66648-43-9
SMILES
COC1=C(O)C=CC(\C=C\C(\O)=N\CCC2=CC=C(O)C=C2)=C1
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point144.5 - 145 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Prostaglandin G/H synthase 2PTGS21q25.2-q25.3P35354 details
Prostaglandin G/H synthase 1PTGS19q32-q33.3P23219 details
Epidermal growth factor receptorEGFR7p12P00533 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Prostaglandin G/H synthase 2PTGS21q25.2-q25.3P35354 details
Prostaglandin G/H synthase 1PTGS19q32-q33.3P23219 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Prostaglandin G/H synthase 1PTGS19q32-q33.3P23219 details
Epidermal growth factor receptorEGFR7p12P00533 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0029365
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000432
KNApSAcK IDC00000660
Chemspider ID4444168
KEGG Compound IDC02717
BioCyc IDCPD-440
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280537
PDB IDNot Available
ChEBI ID17818
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Park JB: Isolation and characterization of N-feruloyltyramine as the P-selectin expression suppressor from garlic (Allium sativum). J Agric Food Chem. 2009 Oct 14;57(19):8868-72. doi: 10.1021/jf9018382. [PubMed:19807156 ]

Enzymes

Enzyme Details
1. Prostaglandin G/H synthase 2
General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
Enzyme Details
2. Prostaglandin G/H synthase 1
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
Enzyme Details
3. Epidermal growth factor receptor
General function:
Involved in transmembrane receptor protein tyrosine kinase activity
Specific function:
Isoform 2 may act as an antagonist of EGF action
Gene Name:
EGFR
Uniprot ID:
P00533
Molecular weight:
134276.2