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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:51:56 UTC
Update Date2022-03-07 02:53:28 UTC
HMDB IDHMDB0032805
Secondary Accession Numbers
  • HMDB32805
Metabolite Identification
Common NameN-trans-Feruloyloctopamine
DescriptionN-trans-Feruloyloctopamine belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated. N-trans-Feruloyloctopamine is found, on average, in the highest concentration within a few different foods, such as yellow bell peppers (Capsicum annuum), red bell peppers (Capsicum annuum), and peppers (Capsicum annuum) and in a lower concentration in orange bell peppers (Capsicum annuum) and green bell peppers (Capsicum annuum). N-trans-Feruloyloctopamine has also been detected, but not quantified in, several different foods, such as eggplants (Solanum melongena), fruits, herbs and spices, italian sweet red peppers (Capsicum annuum), and potatos (Solanum tuberosum). This could make N-trans-feruloyloctopamine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on N-trans-Feruloyloctopamine.
Structure
Data?1563862310
Synonyms
ValueSource
N-FeruloyloctopamineMeSH
N-cis-FeruloyloctopamineHMDB
(2E)-N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enimidateGenerator
N-trans-FeruloyloctopamineMeSH
Chemical FormulaC18H19NO5
Average Molecular Weight329.3472
Monoisotopic Molecular Weight329.126322723
IUPAC Name(2E)-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
Traditional Name(2E)-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
CAS Registry Number66648-44-0
SMILES
COC1=CC(\C=C\C(=O)NCC(O)C2=CC=C(O)C=C2)=CC=C1O
InChI Identifier
InChI=1S/C18H19NO5/c1-24-17-10-12(2-8-15(17)21)3-9-18(23)19-11-16(22)13-4-6-14(20)7-5-13/h2-10,16,20-22H,11H2,1H3,(H,19,23)/b9-3+
InChI KeyVJSCHQMOTSXAKB-YCRREMRBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids and derivatives
Alternative Parents
Substituents
  • Cinnamic acid amide
  • Hydroxycinnamic acid or derivatives
  • Methoxyphenol
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Styrene
  • Methoxybenzene
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid derivative
  • Ether
  • Organic oxygen compound
  • Aromatic alcohol
  • Organic nitrogen compound
  • Organic oxide
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organonitrogen 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 Point164 - 165 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.048 g/LALOGPS
logP1.61ALOGPS
logP1.88ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)9.33ChemAxon
pKa (Strongest Basic)1.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.02 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity90.78 m³·mol⁻¹ChemAxon
Polarizability34.9 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]+176.71330932474
DeepCCS[M-H]-174.35530932474
DeepCCS[M-2H]-208.6130932474
DeepCCS[M+Na]+184.20530932474
AllCCS[M+H]+179.432859911
AllCCS[M+H-H2O]+176.232859911
AllCCS[M+NH4]+182.432859911
AllCCS[M+Na]+183.332859911
AllCCS[M-H]-179.332859911
AllCCS[M+Na-2H]-179.332859911
AllCCS[M+HCOO]-179.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-trans-FeruloyloctopamineCOC1=CC(\C=C\C(=O)NCC(O)C2=CC=C(O)C=C2)=CC=C1O4751.4Standard polar33892256
N-trans-FeruloyloctopamineCOC1=CC(\C=C\C(=O)NCC(O)C2=CC=C(O)C=C2)=CC=C1O3150.6Standard non polar33892256
N-trans-FeruloyloctopamineCOC1=CC(\C=C\C(=O)NCC(O)C2=CC=C(O)C=C2)=CC=C1O3582.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-trans-Feruloyloctopamine,1TMS,isomer #1COC1=CC(/C=C/C(=O)NCC(O[Si](C)(C)C)C2=CC=C(O)C=C2)=CC=C1O3400.2Semi standard non polar33892256
N-trans-Feruloyloctopamine,1TMS,isomer #2COC1=CC(/C=C/C(=O)NCC(O)C2=CC=C(O[Si](C)(C)C)C=C2)=CC=C1O3431.7Semi standard non polar33892256
N-trans-Feruloyloctopamine,1TMS,isomer #3COC1=CC(/C=C/C(=O)NCC(O)C2=CC=C(O)C=C2)=CC=C1O[Si](C)(C)C3440.4Semi standard non polar33892256
N-trans-Feruloyloctopamine,1TMS,isomer #4COC1=CC(/C=C/C(=O)N(CC(O)C2=CC=C(O)C=C2)[Si](C)(C)C)=CC=C1O3371.4Semi standard non polar33892256
N-trans-Feruloyloctopamine,2TMS,isomer #1COC1=CC(/C=C/C(=O)NCC(O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C2)=CC=C1O3314.8Semi standard non polar33892256
N-trans-Feruloyloctopamine,2TMS,isomer #2COC1=CC(/C=C/C(=O)NCC(O[Si](C)(C)C)C2=CC=C(O)C=C2)=CC=C1O[Si](C)(C)C3376.1Semi standard non polar33892256
N-trans-Feruloyloctopamine,2TMS,isomer #3COC1=CC(/C=C/C(=O)N(CC(O[Si](C)(C)C)C2=CC=C(O)C=C2)[Si](C)(C)C)=CC=C1O3322.0Semi standard non polar33892256
N-trans-Feruloyloctopamine,2TMS,isomer #4COC1=CC(/C=C/C(=O)NCC(O)C2=CC=C(O[Si](C)(C)C)C=C2)=CC=C1O[Si](C)(C)C3444.8Semi standard non polar33892256
N-trans-Feruloyloctopamine,2TMS,isomer #5COC1=CC(/C=C/C(=O)N(CC(O)C2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)=CC=C1O3272.1Semi standard non polar33892256
N-trans-Feruloyloctopamine,2TMS,isomer #6COC1=CC(/C=C/C(=O)N(CC(O)C2=CC=C(O)C=C2)[Si](C)(C)C)=CC=C1O[Si](C)(C)C3323.8Semi standard non polar33892256
N-trans-Feruloyloctopamine,3TMS,isomer #1COC1=CC(/C=C/C(=O)NCC(O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C2)=CC=C1O[Si](C)(C)C3326.9Semi standard non polar33892256
N-trans-Feruloyloctopamine,3TMS,isomer #2COC1=CC(/C=C/C(=O)N(CC(O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)=CC=C1O3226.7Semi standard non polar33892256
N-trans-Feruloyloctopamine,3TMS,isomer #3COC1=CC(/C=C/C(=O)N(CC(O[Si](C)(C)C)C2=CC=C(O)C=C2)[Si](C)(C)C)=CC=C1O[Si](C)(C)C3292.7Semi standard non polar33892256
N-trans-Feruloyloctopamine,3TMS,isomer #4COC1=CC(/C=C/C(=O)N(CC(O)C2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)=CC=C1O[Si](C)(C)C3306.6Semi standard non polar33892256
N-trans-Feruloyloctopamine,4TMS,isomer #1COC1=CC(/C=C/C(=O)N(CC(O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)=CC=C1O[Si](C)(C)C3279.1Semi standard non polar33892256
N-trans-Feruloyloctopamine,4TMS,isomer #1COC1=CC(/C=C/C(=O)N(CC(O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)=CC=C1O[Si](C)(C)C2855.6Standard non polar33892256
N-trans-Feruloyloctopamine,1TBDMS,isomer #1COC1=CC(/C=C/C(=O)NCC(O[Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C2)=CC=C1O3667.9Semi standard non polar33892256
N-trans-Feruloyloctopamine,1TBDMS,isomer #2COC1=CC(/C=C/C(=O)NCC(O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=CC=C1O3719.2Semi standard non polar33892256
N-trans-Feruloyloctopamine,1TBDMS,isomer #3COC1=CC(/C=C/C(=O)NCC(O)C2=CC=C(O)C=C2)=CC=C1O[Si](C)(C)C(C)(C)C3716.9Semi standard non polar33892256
N-trans-Feruloyloctopamine,1TBDMS,isomer #4COC1=CC(/C=C/C(=O)N(CC(O)C2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)=CC=C1O3643.9Semi standard non polar33892256
N-trans-Feruloyloctopamine,2TBDMS,isomer #1COC1=CC(/C=C/C(=O)NCC(O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=CC=C1O3824.5Semi standard non polar33892256
N-trans-Feruloyloctopamine,2TBDMS,isomer #2COC1=CC(/C=C/C(=O)NCC(O[Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C2)=CC=C1O[Si](C)(C)C(C)(C)C3894.1Semi standard non polar33892256
N-trans-Feruloyloctopamine,2TBDMS,isomer #3COC1=CC(/C=C/C(=O)N(CC(O[Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)=CC=C1O3829.9Semi standard non polar33892256
N-trans-Feruloyloctopamine,2TBDMS,isomer #4COC1=CC(/C=C/C(=O)NCC(O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=CC=C1O[Si](C)(C)C(C)(C)C3987.7Semi standard non polar33892256
N-trans-Feruloyloctopamine,2TBDMS,isomer #5COC1=CC(/C=C/C(=O)N(CC(O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)=CC=C1O3807.2Semi standard non polar33892256
N-trans-Feruloyloctopamine,2TBDMS,isomer #6COC1=CC(/C=C/C(=O)N(CC(O)C2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C3837.1Semi standard non polar33892256
N-trans-Feruloyloctopamine,3TBDMS,isomer #1COC1=CC(/C=C/C(=O)NCC(O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=CC=C1O[Si](C)(C)C(C)(C)C4019.0Semi standard non polar33892256
N-trans-Feruloyloctopamine,3TBDMS,isomer #2COC1=CC(/C=C/C(=O)N(CC(O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)=CC=C1O3962.4Semi standard non polar33892256
N-trans-Feruloyloctopamine,3TBDMS,isomer #3COC1=CC(/C=C/C(=O)N(CC(O[Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C4012.1Semi standard non polar33892256
N-trans-Feruloyloctopamine,3TBDMS,isomer #4COC1=CC(/C=C/C(=O)N(CC(O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C4061.9Semi standard non polar33892256
N-trans-Feruloyloctopamine,4TBDMS,isomer #1COC1=CC(/C=C/C(=O)N(CC(O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C4210.5Semi standard non polar33892256
N-trans-Feruloyloctopamine,4TBDMS,isomer #1COC1=CC(/C=C/C(=O)N(CC(O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C3670.8Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-trans-Feruloyloctopamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0229-3922000000-70a98890dfafb6fb93a72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-trans-Feruloyloctopamine GC-MS (3 TMS) - 70eV, Positivesplash10-001i-4160490000-84d4224a354d6bc292d02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-trans-Feruloyloctopamine 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 - N-trans-Feruloyloctopamine , positive-QTOFsplash10-002b-0900000000-ee476b7a2a64a0fde0c52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-trans-Feruloyloctopamine 10V, Positive-QTOFsplash10-01t9-0914000000-c22dc038cc81578febd22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-trans-Feruloyloctopamine 20V, Positive-QTOFsplash10-004i-0900000000-0475d75f1df32fa4e1cc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-trans-Feruloyloctopamine 20V, Negative-QTOFsplash10-03di-0921000000-da4bf1c4510c680ed3d12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-trans-Feruloyloctopamine 10V, Negative-QTOFsplash10-03di-0109000000-fa82a2adb5754c3aa4772021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-trans-Feruloyloctopamine 40V, Negative-QTOFsplash10-001i-0900000000-04918079add60c49ec642021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-trans-Feruloyloctopamine 10V, Positive-QTOFsplash10-0w30-0906000000-b9cb734c887dcf756d5a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-trans-Feruloyloctopamine 20V, Positive-QTOFsplash10-0f89-0900000000-b691ce4e80debd4f00e52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-trans-Feruloyloctopamine 40V, Positive-QTOFsplash10-008a-1900000000-f5f510b5c1690842dc3e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-trans-Feruloyloctopamine 10V, Negative-QTOFsplash10-004i-0309000000-7619637282219a3cd8892016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-trans-Feruloyloctopamine 20V, Negative-QTOFsplash10-01r6-0904000000-795837b829982fc9f11e2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-trans-Feruloyloctopamine 40V, Negative-QTOFsplash10-0006-4900000000-3c40a3ce4f081c61f24c2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-trans-Feruloyloctopamine 10V, Negative-QTOFsplash10-004i-0109000000-b25010531c9363553a872021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-trans-Feruloyloctopamine 20V, Negative-QTOFsplash10-03gu-1903000000-4af2ab95365302b621f52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-trans-Feruloyloctopamine 40V, Negative-QTOFsplash10-0016-1910000000-e5f51a91c189bed734fd2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-trans-Feruloyloctopamine 10V, Positive-QTOFsplash10-03e9-0409000000-e1c902310c68290b04042021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-trans-Feruloyloctopamine 20V, Positive-QTOFsplash10-03di-0925000000-e86b4eff0c7f68c4d29c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-trans-Feruloyloctopamine 40V, Positive-QTOFsplash10-0002-2910000000-9619bbe6a050c19b62ba2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB010779
KNApSAcK IDC00035344
Chemspider ID22913041
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24096391
PDB IDNot Available
ChEBI IDNot Available
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.. .