Record Information
Version1.0
Creation date2010-04-08 22:15:44 UTC
Update date2019-11-26 03:20:27 UTC
Primary IDFDB021495
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNb-trans-p-Coumaroylserotonin
DescriptionN6-cis-p-Coumaroylserotonin, also known as p-C-serotonin, belongs to the class of organic compounds known as n-acylserotonins. These are aromatic heterocyclic compounds containing a serotonin, in which the amine group is acylated. N6-cis-p-Coumaroylserotonin has been detected, but not quantified in, root vegetables. This could make N6-cis-p-coumaroylserotonin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on N6-cis-p-Coumaroylserotonin.
CAS Number68573-24-0
Structure
Thumb
Synonyms
SynonymSource
N-(p-Coumaroyl)serotoninHMDB
4-CoumaroylserotoninHMDB
p-C-SerotoninHMDB
(2E)-N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enimidateHMDB
Ipobscurine Adb_source
N6-cis-P-CoumaroylserotoninHMDB
Nb-p-Coumaroylserotonindb_source
Nb-trans-p-Coumaroylserotoninmanual
Predicted Properties
PropertyValueSource
Water Solubility0.0056 g/LALOGPS
logP3.01ALOGPS
logP3.06ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)9.18ChemAxon
pKa (Strongest Basic)1.21ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area85.35 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity94.19 m³·mol⁻¹ChemAxon
Polarizability35.27 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC19H18N2O3
IUPAC name(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide
InChI IdentifierInChI=1S/C19H18N2O3/c22-15-4-1-13(2-5-15)3-8-19(24)20-10-9-14-12-21-18-7-6-16(23)11-17(14)18/h1-8,11-12,21-23H,9-10H2,(H,20,24)/b8-3+
InChI KeyWLZPAFGVOWCVMG-FPYGCLRLSA-N
Isomeric SMILESOC1=CC=C(\C=C\C(=O)NCCC2=CNC3=C2C=C(O)C=C3)C=C1
Average Molecular Weight322.3578
Monoisotopic Molecular Weight322.131742452
Classification
Description Belongs to the class of organic compounds known as n-acylserotonins. These are aromatic heterocyclic compounds containing a serotonin, in which the amine group is acylated.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassTryptamines and derivatives
Direct ParentN-acylserotonins
Alternative Parents
Substituents
  • N-acylserotonin
  • Cinnamic acid amide
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Hydroxyindole
  • 3-alkylindole
  • Indole
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Azacycle
  • Carboxylic acid derivative
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 70.79%; H 5.63%; N 8.69%; O 14.89%DFC
Melting PointNot Available
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-MSNb-cis-p-Coumaroylserotonin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00kb-0910000000-037a97844777dd79abceSpectrum
Predicted GC-MSNb-cis-p-Coumaroylserotonin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-3394800000-8991661558a8e8fa285bSpectrum
Predicted GC-MSNb-cis-p-Coumaroylserotonin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNb-cis-p-Coumaroylserotonin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00b9-0903000000-84fe2e000fe834419c63Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0900000000-7309c1f71fe3d9227583Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06r2-1900000000-3fe2b7a2aa846d1498e8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0309000000-f5fabf8a91db547434c3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-022a-0914000000-6ea027e67f01db5ef161Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-6900000000-bce88a8597408f7f0174Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0409000000-b5e695c1496bbd99453cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fr-0902000000-36f1391fa39443f83654Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-1900000000-9278907f3a5d0f6f9139Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-0a90bce16d9084968bc3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-1926000000-dc21115b4587fbbf850aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-8920000000-c9f2042f64c8cc4b18ebSpectrum
NMRNot Available
ChemSpider ID4572762
ChEMBL IDCHEMBL1760547
KEGG Compound IDNot Available
Pubchem Compound ID5458879
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB38340
CRC / DFC (Dictionary of Food Compounds) IDHDV23-B:NZJ11-A
EAFUS IDNot Available
Dr. Duke IDNot Available
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
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