Record Information
Version1.0
Creation date2010-04-08 22:09:18 UTC
Update date2019-11-26 03:04:06 UTC
Primary IDFDB010778
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameN-trans-p-Coumaroyloctopamine
DescriptionN-trans-p-Coumaroyloctopamine, also known as 4-coumaroylnoradrenaline, 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. N-trans-p-Coumaroyloctopamine 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-p-Coumaroyloctopamine has also been detected, but not quantified in, several different foods, such as eggplants (Solanum melongena), fruits, herbs and spices, and italian sweet red peppers (Capsicum annuum). This could make N-trans-p-coumaroyloctopamine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on N-trans-p-Coumaroyloctopamine.
CAS Number66648-45-1
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.053 g/LALOGPS
logP1.72ALOGPS
logP2.04ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)9.14ChemAxon
pKa (Strongest Basic)1.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area89.79 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity84.32 m³·mol⁻¹ChemAxon
Polarizability31.98 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H17NO4
IUPAC name(2E)-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide
InChI IdentifierInChI=1S/C17H17NO4/c19-14-6-1-12(2-7-14)3-10-17(22)18-11-16(21)13-4-8-15(20)9-5-13/h1-10,16,19-21H,11H2,(H,18,22)/b10-3+
InChI KeyVATOSFCFMOPAHX-XCVCLJGOSA-N
Isomeric SMILESOC(CNC(=O)\C=C\C1=CC=C(O)C=C1)C1=CC=C(O)C=C1
Average Molecular Weight299.3212
Monoisotopic Molecular Weight299.115758037
Classification
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
  • Cinnamic acid amide
  • Coumaric acid or derivatives
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aromatic alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSN-trans-p-Coumaroyloctopamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-0900000000-0ba05c978dff5b24c306Spectrum
Predicted GC-MSN-trans-p-Coumaroyloctopamine, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0gb9-1090450000-c10b722e4a5cd1e6bbd2Spectrum
Predicted GC-MSN-trans-p-Coumaroyloctopamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-trans-p-Coumaroyloctopamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - , positivesplash10-00kb-1900000000-29b16de0f286b9a092742017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0942000000-d0e0ef047e5f241982c82016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-0910000000-c15f4d7b37269c8beae82016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lr-2900000000-b4337e626d7250b577d22016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0490000000-e86731289ee0963bc99f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01qa-0940000000-36f3892e9aed33345b142016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-8900000000-6e5243030ba8a49f8f722016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0190000000-1bde48a474cc2f42cbac2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-0950000000-cae6c006eb3c2f99f1802021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-1900000000-a239a9ef516714796b202021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-13baaeac51cf8b64a0582021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-067m-2970000000-a24388608b907f3e2be82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1930000000-9458f3bff5805b98ed222021-09-22View Spectrum
NMRNot Available
ChemSpider ID23550803
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID23874492
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB32804
CRC / DFC (Dictionary of Food Compounds) IDFFG71-J:FON85-K
EAFUS IDNot Available
Dr. Duke IDN-TRANS-P-COUMAROYL-OCTOPAMINE
BIGG IDNot Available
KNApSAcK IDNot Available
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
EggplantExpected but not quantifiedNot AvailableDUKE
Green bell pepper0.10000 - 0.10000 mg/100 g0.10000 mg/100 gDUKE
Orange bell pepper0.10000 - 0.10000 mg/100 g0.10000 mg/100 gDUKE
Pepper0.10000 - 0.10000 mg/100 g0.10000 mg/100 gDUKE
Red bell pepper0.10000 - 0.10000 mg/100 g0.10000 mg/100 gDUKE
Yellow bell pepper0.10000 - 0.10000 mg/100 g0.10000 mg/100 gDUKE
Italian sweet red pepperExpected but not quantifiedNot AvailableInferred by geno/metabolomic analysis
Showing 1 to 7 of 7 entries
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).