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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:09:35 UTC
Update Date2022-03-07 02:56:17 UTC
HMDB IDHMDB0039632
Secondary Accession Numbers
  • HMDB39632
Metabolite Identification
Common NameN-[2-Methoxy-2-(4-methoxyphenyl)ethyl]cinnamide
DescriptionN-[2-Methoxy-2-(4-methoxyphenyl)ethyl]cinnamide belongs to the class of organic compounds known as cinnamic acid amides. These are amides of cinnamic acids. Cinnamic acid is an aromatic compound containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. N-[2-Methoxy-2-(4-methoxyphenyl)ethyl]cinnamide has been detected, but not quantified in, fruits. This could make N-[2-methoxy-2-(4-methoxyphenyl)ethyl]cinnamide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on N-[2-Methoxy-2-(4-methoxyphenyl)ethyl]cinnamide.
Structure
Data?1563863411
Synonyms
ValueSource
Aegle marmelos alkaloid DHMDB
(2E)-N-[2-Methoxy-2-(4-methoxyphenyl)ethyl]-3-phenylprop-2-enimidateGenerator
Chemical FormulaC19H21NO3
Average Molecular Weight311.3749
Monoisotopic Molecular Weight311.152143543
IUPAC Name(2E)-N-[2-methoxy-2-(4-methoxyphenyl)ethyl]-3-phenylprop-2-enamide
Traditional Name(2E)-N-[2-methoxy-2-(4-methoxyphenyl)ethyl]-3-phenylprop-2-enamide
CAS Registry Number70546-93-9
SMILES
COC(CNC(=O)\C=C\C1=CC=CC=C1)C1=CC=C(OC)C=C1
InChI Identifier
InChI=1S/C19H21NO3/c1-22-17-11-9-16(10-12-17)18(23-2)14-20-19(21)13-8-15-6-4-3-5-7-15/h3-13,18H,14H2,1-2H3,(H,20,21)/b13-8+
InChI KeyPJIOBHFHQZPYOX-MDWZMJQESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cinnamic acid amides. These are amides of cinnamic acids. Cinnamic acid is an aromatic compound containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassCinnamic acid amides
Direct ParentCinnamic acid amides
Alternative Parents
Substituents
  • Cinnamic acid amide
  • Benzylether
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Ether
  • Dialkyl ether
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point135 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility49.24 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0032 g/LALOGPS
logP2.92ALOGPS
logP3.13ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)15.59ChemAxon
pKa (Strongest Basic)1.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area47.56 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity91.57 m³·mol⁻¹ChemAxon
Polarizability34.97 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+178.03830932474
DeepCCS[M-H]-175.67930932474
DeepCCS[M-2H]-208.70930932474
DeepCCS[M+Na]+184.13130932474
AllCCS[M+H]+177.432859911
AllCCS[M+H-H2O]+174.032859911
AllCCS[M+NH4]+180.632859911
AllCCS[M+Na]+181.532859911
AllCCS[M-H]-179.732859911
AllCCS[M+Na-2H]-179.732859911
AllCCS[M+HCOO]-179.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-[2-Methoxy-2-(4-methoxyphenyl)ethyl]cinnamideCOC(CNC(=O)\C=C\C1=CC=CC=C1)C1=CC=C(OC)C=C13899.4Standard polar33892256
N-[2-Methoxy-2-(4-methoxyphenyl)ethyl]cinnamideCOC(CNC(=O)\C=C\C1=CC=CC=C1)C1=CC=C(OC)C=C12550.3Standard non polar33892256
N-[2-Methoxy-2-(4-methoxyphenyl)ethyl]cinnamideCOC(CNC(=O)\C=C\C1=CC=CC=C1)C1=CC=C(OC)C=C12804.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-[2-Methoxy-2-(4-methoxyphenyl)ethyl]cinnamide,1TMS,isomer #1COC1=CC=C(C(CN(C(=O)/C=C/C2=CC=CC=C2)[Si](C)(C)C)OC)C=C12763.2Semi standard non polar33892256
N-[2-Methoxy-2-(4-methoxyphenyl)ethyl]cinnamide,1TMS,isomer #1COC1=CC=C(C(CN(C(=O)/C=C/C2=CC=CC=C2)[Si](C)(C)C)OC)C=C12458.3Standard non polar33892256
N-[2-Methoxy-2-(4-methoxyphenyl)ethyl]cinnamide,1TBDMS,isomer #1COC1=CC=C(C(CN(C(=O)/C=C/C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)OC)C=C12978.9Semi standard non polar33892256
N-[2-Methoxy-2-(4-methoxyphenyl)ethyl]cinnamide,1TBDMS,isomer #1COC1=CC=C(C(CN(C(=O)/C=C/C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)OC)C=C12663.4Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-[2-Methoxy-2-(4-methoxyphenyl)ethyl]cinnamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ul0-2910000000-bcce5d654ed174cc10732017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-[2-Methoxy-2-(4-methoxyphenyl)ethyl]cinnamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-[2-Methoxy-2-(4-methoxyphenyl)ethyl]cinnamide 10V, Positive-QTOFsplash10-01q9-0913000000-81a211a68be18575fd302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-[2-Methoxy-2-(4-methoxyphenyl)ethyl]cinnamide 20V, Positive-QTOFsplash10-001i-0900000000-496fe12add15c5e5aa422016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-[2-Methoxy-2-(4-methoxyphenyl)ethyl]cinnamide 40V, Positive-QTOFsplash10-0udj-0900000000-74811511199daed19a3f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-[2-Methoxy-2-(4-methoxyphenyl)ethyl]cinnamide 10V, Negative-QTOFsplash10-03di-0319000000-0a25983dc17f2cb8734c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-[2-Methoxy-2-(4-methoxyphenyl)ethyl]cinnamide 20V, Negative-QTOFsplash10-03dj-1932000000-9937992487af183724342016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-[2-Methoxy-2-(4-methoxyphenyl)ethyl]cinnamide 40V, Negative-QTOFsplash10-0006-6900000000-9170f918ea08c43097e62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-[2-Methoxy-2-(4-methoxyphenyl)ethyl]cinnamide 10V, Positive-QTOFsplash10-001i-0922000000-0da663cdb4eec649bd732021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-[2-Methoxy-2-(4-methoxyphenyl)ethyl]cinnamide 20V, Positive-QTOFsplash10-0ue9-0910000000-b7ec668fcbae165d29d22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-[2-Methoxy-2-(4-methoxyphenyl)ethyl]cinnamide 40V, Positive-QTOFsplash10-0udi-0900000000-35ebc39b76956e5d95322021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-[2-Methoxy-2-(4-methoxyphenyl)ethyl]cinnamide 10V, Negative-QTOFsplash10-03fr-0179000000-83a78426fa9c65120a3e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-[2-Methoxy-2-(4-methoxyphenyl)ethyl]cinnamide 20V, Negative-QTOFsplash10-0w4m-3912000000-dd3ee6aeeeb028dbc8a72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-[2-Methoxy-2-(4-methoxyphenyl)ethyl]cinnamide 40V, Negative-QTOFsplash10-0pdu-7913000000-6a31b1edc49b7b20895b2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB019260
KNApSAcK IDNot Available
Chemspider ID4581612
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5471458
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1878941
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .