Showing Compound Card for n-(p-hydroxy-β-phenylethyl)-p-hydroxy-(trans)-cinnamide (CDB000229)

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Record Information
Version1.0
Created at2020-03-19 00:25:43 UTC
Updated at2020-12-07 19:07:16 UTC
CannabisDB IDCDB000229
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namen-(p-hydroxy-β-phenylethyl)-p-hydroxy-(trans)-cinnamide
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. Paprazine is one of the compounds that have been identified in hempseed (Cannabis sativa) ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight283.32
Monoisotopic Molecular Weight283.1208
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 Number20375-37-5
SMILES
O\C(\C=C\C1=CC=C(O)C=C1)=N/CCC1=CC=C(O)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
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point260 - 261 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSn-(p-hydroxy-β-phenylethyl)-p-hydroxy-(trans)-cinnamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052b-0910000000-6be5a92b4c900bc4314dSpectrum
Predicted GC-MSn-(p-hydroxy-β-phenylethyl)-p-hydroxy-(trans)-cinnamide, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-5886900000-4e07b44443bb550b6f3aSpectrum
Predicted GC-MSn-(p-hydroxy-β-phenylethyl)-p-hydroxy-(trans)-cinnamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSn-(p-hydroxy-β-phenylethyl)-p-hydroxy-(trans)-cinnamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-0940000000-67eca6cd4610cdb6385c2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-0900000000-76a2a687a7fdc6dff8ac2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ap0-2900000000-37f55b85aa3f8f38b0ac2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0390000000-c6c693214244c760e76d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03e9-0940000000-629ce8460c91a8cf71ca2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-7900000000-670117754556b9bfd7372016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0490000000-eb6448de7547cc12159f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00e9-0940000000-110219e85b66ace2e7eb2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0600-3900000000-3336c5e4da5dd7892b8a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0190000000-1ca5c616e12c1f59d6cd2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053r-1970000000-ba1058b269f97d0521a52021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-2920000000-ed1f42ff191ef6b462962021-09-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0039521
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]