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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:52:32 UTC
Update Date2022-03-07 02:55:49 UTC
HMDB IDHMDB0038551
Secondary Accession Numbers
  • HMDB38551
Metabolite Identification
Common NameMethyl 3,4,5-trimethoxycinnamate
DescriptionMethyl 3,4,5-trimethoxycinnamate, also known as 3,4,5-trimethoxycinnamate methyl ester, belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Methyl 3,4,5-trimethoxycinnamate has been detected, but not quantified in, herbs and spices. This could make methyl 3,4,5-trimethoxycinnamate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Methyl 3,4,5-trimethoxycinnamate.
Structure
Data?1563863216
Synonyms
ValueSource
3,4,5-Trimethoxycinnamic acid methyl esterChEBI
3,4,5-Trimethoxycinnamate methyl esterGenerator
Methyl 3,4,5-trimethoxycinnamic acidGenerator
Methyl-3,4,5-trimethoxy cinnamic acidHMDB
Chemical FormulaC13H16O5
Average Molecular Weight252.2631
Monoisotopic Molecular Weight252.099773622
IUPAC Namemethyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate
Traditional Namemethyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate
CAS Registry Number20329-96-8
SMILES
COC(=O)\C=C\C1=CC(OC)=C(OC)C(OC)=C1
InChI Identifier
InChI=1S/C13H16O5/c1-15-10-7-9(5-6-12(14)17-3)8-11(16-2)13(10)18-4/h5-8H,1-4H3/b6-5+
InChI KeyKLXHCGFNNUQTEY-AATRIKPKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acids and derivatives
Alternative Parents
Substituents
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Styrene
  • Alkyl aryl ether
  • Fatty acid ester
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Alpha,beta-unsaturated carboxylic ester
  • Methyl ester
  • Enoate ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point99 - 100 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.079 g/LALOGPS
logP2.53ALOGPS
logP2.04ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area53.99 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity67.22 m³·mol⁻¹ChemAxon
Polarizability26.6 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+163.73431661259
DarkChem[M-H]-163.27531661259
DeepCCS[M+H]+160.59430932474
DeepCCS[M-H]-158.2230932474
DeepCCS[M-2H]-191.10630932474
DeepCCS[M+Na]+166.67130932474
AllCCS[M+H]+157.732859911
AllCCS[M+H-H2O]+154.032859911
AllCCS[M+NH4]+161.132859911
AllCCS[M+Na]+162.132859911
AllCCS[M-H]-159.932859911
AllCCS[M+Na-2H]-160.232859911
AllCCS[M+HCOO]-160.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Methyl 3,4,5-trimethoxycinnamateCOC(=O)\C=C\C1=CC(OC)=C(OC)C(OC)=C13184.2Standard polar33892256
Methyl 3,4,5-trimethoxycinnamateCOC(=O)\C=C\C1=CC(OC)=C(OC)C(OC)=C11938.8Standard non polar33892256
Methyl 3,4,5-trimethoxycinnamateCOC(=O)\C=C\C1=CC(OC)=C(OC)C(OC)=C12102.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Methyl 3,4,5-trimethoxycinnamate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00du-0690000000-36255dc7ae0bd83ff8a52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl 3,4,5-trimethoxycinnamate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate , positive-QTOFsplash10-022c-0940000000-96354eb898855b8e905d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate , positive-QTOFsplash10-000i-1920000000-f2f693c1c78cd6ef2b292017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 10V, Positive-QTOFsplash10-00di-0290000000-c8ecf3965a9c83a563812021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 20V, Positive-QTOFsplash10-022c-0940000000-8b93bb36ccc3e076e9452021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 40V, Positive-QTOFsplash10-07mv-4900000000-c635331ee3e0b65d77412021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 10V, Negative-QTOFsplash10-0udi-0090000000-fe93b401f1321fcc37ba2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 20V, Negative-QTOFsplash10-0uy0-0290000000-2807d3e5a8560757b0502016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 40V, Negative-QTOFsplash10-0a59-1930000000-e4ce758b6ce5a108f57b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 10V, Negative-QTOFsplash10-0uxr-0090000000-df5f63af7cb771b611ad2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 20V, Negative-QTOFsplash10-0i0c-0980000000-6c28694657f3a00eeed12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 40V, Negative-QTOFsplash10-06vj-1910000000-5ba44afb44d12123a0662021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 10V, Positive-QTOFsplash10-0fk9-0090000000-c8e7b119aab8b699ab7c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 20V, Positive-QTOFsplash10-0fk9-1390000000-117d5df646bc9ca490102016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 40V, Positive-QTOFsplash10-0a4l-2940000000-ab5ee043bc5d575d6fdd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 10V, Positive-QTOFsplash10-0uk9-0090000000-76606a89e13ac877c1632021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 20V, Positive-QTOFsplash10-0fkc-0490000000-93a87722bafafb1739722021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3,4,5-trimethoxycinnamate 40V, Positive-QTOFsplash10-0a4j-0910000000-6811633d14eb7b224c9e2021-09-22Wishart 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 IDFDB017938
KNApSAcK IDC00057228
Chemspider ID643000
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound735846
PDB IDNot Available
ChEBI ID86898
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.. .