Record Information
Version1.0
Creation date2010-04-08 22:14:09 UTC
Update date2020-09-17 15:31:43 UTC
Primary IDFDB019132
Secondary Accession Numbers
  • FDB004679
  • FDB020357
Chemical Information
FooDB NameN-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide
DescriptionN-Trans-Coumaroyltyramine or N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide is also known as paprazine, N-trans-paprazine or trans-N-p-coumaroyl tyramine. It belongs to the class of organic compounds known as coumaric acids and derivatives. It is also classified as a hydroxycoumaric acid. Coumaric acids are 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. There are two isomers of paprazine, N-trans-paprazine and N-cis-paprazine. Paprazine is a neutral, hydrophobic molecule that is largely insoluble in water.
CAS Number36417-86-4
Structure
Thumb
Synonyms
SynonymSource
N-trans-CoumaroyltyramineChEMBL, HMDB
trans-N-HydroxycinnamoyltyramineChEMBL, HMDB
N-P-CoumaroyltyramineChEMBL, HMDB
N-P-trans-CoumaroyltyramineHMDB
PaprazineHMDB
4-CoumaroyltyramineMeSH, HMDB
N-(4-Hydroxy-beta-phenethyl)-4-hydroxycinnamideMeSH, HMDB
P-CoumaroyltyramineMeSH, HMDB
N-(P-Hydroxy-beta-phenethyl)-P-hydroxy-trans-cinnamideMeSH, HMDB
N-HBPHTCMeSH, HMDB
(2E)-3-(4-Hydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidateGenerator
trans-N-p-Coumaroyl tyramineMeSH
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamidedb_source
N-p-trans-Coumaroyltyraminedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.016 g/LALOGPS
logP2.58ALOGPS
logP3.19ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.56ChemAxon
pKa (Strongest Basic)6.52ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area73.05 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity83.63 m³·mol⁻¹ChemAxon
Polarizability31.67 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H17NO3
IUPAC name(Z,2E)-3-(4-hydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid
InChI IdentifierInChI=1S/C17H17NO3/c19-15-6-1-13(2-7-15)5-10-17(21)18-12-11-14-3-8-16(20)9-4-14/h1-10,19-20H,11-12H2,(H,18,21)/b10-5+
InChI KeyRXGUTQNKCXHALN-BJMVGYQFSA-N
Isomeric SMILESOC1=CC=C(CCNC(=O)\C=C\C2=CC=C(O)C=C2)C=C1
Average Molecular Weight283.3218
Monoisotopic Molecular Weight283.120843415
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 carboxylic acid amide
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 72.07%; H 6.05%; N 4.94%; O 16.94%DFC
Melting PointMp 260-261°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSN-trans-p-Coumaroyltyramine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052b-0910000000-6be5a92b4c900bc4314dSpectrum
Predicted GC-MSN-trans-p-Coumaroyltyramine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-5886900000-4e07b44443bb550b6f3aSpectrum
Predicted GC-MSN-trans-p-Coumaroyltyramine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-trans-p-Coumaroyltyramine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-0940000000-67eca6cd4610cdb6385cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-0900000000-76a2a687a7fdc6dff8acSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ap0-2900000000-37f55b85aa3f8f38b0acSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0390000000-c6c693214244c760e76dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03e9-0940000000-629ce8460c91a8cf71caSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-7900000000-670117754556b9bfd737Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0490000000-eb6448de7547cc12159fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00e9-0940000000-110219e85b66ace2e7ebSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0600-3900000000-3336c5e4da5dd7892b8aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0190000000-1ca5c616e12c1f59d6cdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053r-1970000000-ba1058b269f97d0521a5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-2920000000-ed1f42ff191ef6b46296Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBCB62-V:LPF53-G
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00028801
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
FoodReference
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