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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:00:29 UTC
Update Date2022-03-07 02:56:14 UTC
HMDB IDHMDB0039521
Secondary Accession Numbers
  • HMDB39521
Metabolite Identification
Common NameN-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide
DescriptionN-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 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-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide has been detected, but not quantified in, several different foods, such as red onion, green onion, onion-family vegetables, garden onions (Allium cepa), and pulses. This could make N-(p-hydroxyphenyl)ethyl p-hydroxycinnamide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide.
Structure
Data?1563863390
Synonyms
ValueSource
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
Chemical FormulaC17H17NO3
Average Molecular Weight283.3218
Monoisotopic Molecular Weight283.120843415
IUPAC Name(Z,2E)-3-(4-hydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid
Traditional Name(Z,2E)-3-(4-hydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid
CAS Registry Number36417-86-4
SMILES
OC1=CC=C(CCNC(=O)\C=C\C2=CC=C(O)C=C2)C=C1
InChI Identifier
InChI=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
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
  • 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point260 - 261 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility405.8 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+166.95430932474
DeepCCS[M-H]-164.59630932474
DeepCCS[M-2H]-197.48230932474
DeepCCS[M+Na]+173.04730932474
AllCCS[M+H]+167.632859911
AllCCS[M+H-H2O]+164.032859911
AllCCS[M+NH4]+170.832859911
AllCCS[M+Na]+171.832859911
AllCCS[M-H]-171.132859911
AllCCS[M+Na-2H]-170.832859911
AllCCS[M+HCOO]-170.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamideOC1=CC=C(CCNC(=O)\C=C\C2=CC=C(O)C=C2)C=C14330.7Standard polar33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamideOC1=CC=C(CCNC(=O)\C=C\C2=CC=C(O)C=C2)C=C12539.2Standard non polar33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamideOC1=CC=C(CCNC(=O)\C=C\C2=CC=C(O)C=C2)C=C13223.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(CCNC(=O)/C=C/C2=CC=C(O)C=C2)C=C13086.8Semi standard non polar33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,1TMS,isomer #2C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCC2=CC=C(O)C=C2)C=C13124.0Semi standard non polar33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,1TMS,isomer #3C[Si](C)(C)N(CCC1=CC=C(O)C=C1)C(=O)/C=C/C1=CC=C(O)C=C13094.5Semi standard non polar33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCC2=CC=C(O[Si](C)(C)C)C=C2)C=C13156.2Semi standard non polar33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,2TMS,isomer #2C[Si](C)(C)OC1=CC=C(CCN(C(=O)/C=C/C2=CC=C(O)C=C2)[Si](C)(C)C)C=C13124.7Semi standard non polar33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,2TMS,isomer #3C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCC2=CC=C(O)C=C2)[Si](C)(C)C)C=C13145.0Semi standard non polar33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCC2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)C=C13092.4Semi standard non polar33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCC2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)C=C12863.3Standard non polar33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CCNC(=O)/C=C/C2=CC=C(O)C=C2)C=C13356.4Semi standard non polar33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCC2=CC=C(O)C=C2)C=C13399.0Semi standard non polar33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(CCC1=CC=C(O)C=C1)C(=O)/C=C/C1=CC=C(O)C=C13358.4Semi standard non polar33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C=C13718.3Semi standard non polar33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(CCN(C(=O)/C=C/C2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)C=C13630.0Semi standard non polar33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCC2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)C=C13647.1Semi standard non polar33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)C=C13851.6Semi standard non polar33892256
N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)C=C13440.0Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-052b-0910000000-6be5a92b4c900bc4314d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide GC-MS (2 TMS) - 70eV, Positivesplash10-03di-5886900000-4e07b44443bb550b6f3a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 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-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 10V, Positive-QTOFsplash10-0019-0940000000-67eca6cd4610cdb6385c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 20V, Positive-QTOFsplash10-00kr-0900000000-76a2a687a7fdc6dff8ac2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 40V, Positive-QTOFsplash10-0ap0-2900000000-37f55b85aa3f8f38b0ac2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 10V, Negative-QTOFsplash10-001i-0390000000-c6c693214244c760e76d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 20V, Negative-QTOFsplash10-03e9-0940000000-629ce8460c91a8cf71ca2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 40V, Negative-QTOFsplash10-0006-7900000000-670117754556b9bfd7372016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 10V, Positive-QTOFsplash10-001i-0490000000-eb6448de7547cc12159f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 20V, Positive-QTOFsplash10-00e9-0940000000-110219e85b66ace2e7eb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 40V, Positive-QTOFsplash10-0600-3900000000-3336c5e4da5dd7892b8a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 10V, Negative-QTOFsplash10-001i-0190000000-1ca5c616e12c1f59d6cd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 20V, Negative-QTOFsplash10-053r-1970000000-ba1058b269f97d0521a52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide 40V, Negative-QTOFsplash10-014i-2920000000-ed1f42ff191ef6b462962021-09-22Wishart 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 IDFDB019132
KNApSAcK IDC00028801
Chemspider ID4523095
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5372945
PDB IDNot Available
ChEBI ID65665
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1878051
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.. .