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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:37:58 UTC
Update Date2019-07-23 06:26:21 UTC
HMDB IDHMDB0038340
Secondary Accession Numbers
  • HMDB38340
Metabolite Identification
Common NameN6-cis-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.
Structure
Data?1563863181
Synonyms
ValueSource
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
Chemical FormulaC19H18N2O3
Average Molecular Weight322.3578
Monoisotopic Molecular Weight322.131742452
IUPAC Name(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide
Traditional Name(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide
CAS Registry NumberNot Available
SMILES
OC1=CC=C(\C=C\C(=O)NCCC2=CNC3=C2C=C(O)C=C3)C=C1
InChI Identifier
InChI=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
Chemical Taxonomy
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
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point205 - 206 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0056 g/LALOGPS
logP10(3.01) g/LALOGPS
logP10(3.06) g/LChemAxon
logS10(-4.8) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N6-cis-p-CoumaroylserotoninOC1=CC=C(\C=C\C(=O)NCCC2=CNC3=C2C=C(O)C=C3)C=C15071.3Standard polar33892256
N6-cis-p-CoumaroylserotoninOC1=CC=C(\C=C\C(=O)NCCC2=CNC3=C2C=C(O)C=C3)C=C13094.1Standard non polar33892256
N6-cis-p-CoumaroylserotoninOC1=CC=C(\C=C\C(=O)NCCC2=CNC3=C2C=C(O)C=C3)C=C13928.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N6-cis-p-Coumaroylserotonin,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCC2=C[NH]C3=CC=C(O)C=C23)C=C13687.3Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,1TMS,isomer #2C[Si](C)(C)OC1=CC=C2[NH]C=C(CCNC(=O)/C=C/C3=CC=C(O)C=C3)C2=C13705.9Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,1TMS,isomer #3C[Si](C)(C)N(CCC1=C[NH]C2=CC=C(O)C=C12)C(=O)/C=C/C1=CC=C(O)C=C13672.1Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,1TMS,isomer #4C[Si](C)(C)N1C=C(CCNC(=O)/C=C/C2=CC=C(O)C=C2)C2=CC(O)=CC=C213762.0Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCC2=C[NH]C3=CC=C(O[Si](C)(C)C)C=C23)C=C13670.5Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,2TMS,isomer #2C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCC2=C[NH]C3=CC=C(O)C=C23)[Si](C)(C)C)C=C13655.7Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,2TMS,isomer #3C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCC2=CN([Si](C)(C)C)C3=CC=C(O)C=C23)C=C13756.7Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,2TMS,isomer #4C[Si](C)(C)OC1=CC=C2C(=C1)C(CCNC(=O)/C=C/C1=CC=C(O)C=C1)=CN2[Si](C)(C)C3772.4Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,2TMS,isomer #5C[Si](C)(C)OC1=CC=C2[NH]C=C(CCN(C(=O)/C=C/C3=CC=C(O)C=C3)[Si](C)(C)C)C2=C13687.4Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,2TMS,isomer #6C[Si](C)(C)N(CCC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)C(=O)/C=C/C1=CC=C(O)C=C13788.1Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCC2=C[NH]C3=CC=C(O[Si](C)(C)C)C=C23)[Si](C)(C)C)C=C13602.3Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCC2=C[NH]C3=CC=C(O[Si](C)(C)C)C=C23)[Si](C)(C)C)C=C13607.6Standard non polar33892256
N6-cis-p-Coumaroylserotonin,3TMS,isomer #2C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCC2=CN([Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C23)C=C13713.3Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,3TMS,isomer #2C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCC2=CN([Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C23)C=C13550.2Standard non polar33892256
N6-cis-p-Coumaroylserotonin,3TMS,isomer #3C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCC2=CN([Si](C)(C)C)C3=CC=C(O)C=C23)[Si](C)(C)C)C=C13697.9Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,3TMS,isomer #3C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCC2=CN([Si](C)(C)C)C3=CC=C(O)C=C23)[Si](C)(C)C)C=C13600.8Standard non polar33892256
N6-cis-p-Coumaroylserotonin,3TMS,isomer #4C[Si](C)(C)OC1=CC=C2C(=C1)C(CCN(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C)=CN2[Si](C)(C)C3714.9Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,3TMS,isomer #4C[Si](C)(C)OC1=CC=C2C(=C1)C(CCN(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C)=CN2[Si](C)(C)C3575.5Standard non polar33892256
N6-cis-p-Coumaroylserotonin,4TMS,isomer #1C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCC2=CN([Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C23)[Si](C)(C)C)C=C13635.6Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,4TMS,isomer #1C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCC2=CN([Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C23)[Si](C)(C)C)C=C13426.6Standard non polar33892256
N6-cis-p-Coumaroylserotonin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCC2=C[NH]C3=CC=C(O)C=C23)C=C13971.1Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C2[NH]C=C(CCNC(=O)/C=C/C3=CC=C(O)C=C3)C2=C13974.5Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(CCC1=C[NH]C2=CC=C(O)C=C12)C(=O)/C=C/C1=CC=C(O)C=C13920.6Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C=C(CCNC(=O)/C=C/C2=CC=C(O)C=C2)C2=CC(O)=CC=C213996.6Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCC2=C[NH]C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C23)C=C14239.8Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCC2=C[NH]C3=CC=C(O)C=C23)[Si](C)(C)C(C)(C)C)C=C14175.8Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCC2=CN([Si](C)(C)C(C)(C)C)C3=CC=C(O)C=C23)C=C14251.8Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(CCNC(=O)/C=C/C1=CC=C(O)C=C1)=CN2[Si](C)(C)C(C)(C)C4244.3Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=CC=C2[NH]C=C(CCN(C(=O)/C=C/C3=CC=C(O)C=C3)[Si](C)(C)C(C)(C)C)C2=C14179.7Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)N(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)C(=O)/C=C/C1=CC=C(O)C=C14219.2Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCC2=C[NH]C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C23)[Si](C)(C)C(C)(C)C)C=C14360.9Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCC2=C[NH]C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C23)[Si](C)(C)C(C)(C)C)C=C14152.1Standard non polar33892256
N6-cis-p-Coumaroylserotonin,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCC2=CN([Si](C)(C)C(C)(C)C)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C23)C=C14473.2Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCCC2=CN([Si](C)(C)C(C)(C)C)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C23)C=C14149.1Standard non polar33892256
N6-cis-p-Coumaroylserotonin,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCC2=CN([Si](C)(C)C(C)(C)C)C3=CC=C(O)C=C23)[Si](C)(C)C(C)(C)C)C=C14388.6Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCC2=CN([Si](C)(C)C(C)(C)C)C3=CC=C(O)C=C23)[Si](C)(C)C(C)(C)C)C=C14125.6Standard non polar33892256
N6-cis-p-Coumaroylserotonin,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(CCN(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C4373.2Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(CCN(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C4071.4Standard non polar33892256
N6-cis-p-Coumaroylserotonin,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCC2=CN([Si](C)(C)C(C)(C)C)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C23)[Si](C)(C)C(C)(C)C)C=C14539.4Semi standard non polar33892256
N6-cis-p-Coumaroylserotonin,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CCC2=CN([Si](C)(C)C(C)(C)C)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C23)[Si](C)(C)C(C)(C)C)C=C14048.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N6-cis-p-Coumaroylserotonin GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kb-0910000000-037a97844777dd79abce2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N6-cis-p-Coumaroylserotonin GC-MS (2 TMS) - 70eV, Positivesplash10-0udi-3394800000-8991661558a8e8fa285b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N6-cis-p-Coumaroylserotonin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N6-cis-p-Coumaroylserotonin 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 - N6-cis-p-Coumaroylserotonin 10V, Positive-QTOFsplash10-00b9-0903000000-84fe2e000fe834419c632016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N6-cis-p-Coumaroylserotonin 20V, Positive-QTOFsplash10-056r-0900000000-7309c1f71fe3d92275832016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N6-cis-p-Coumaroylserotonin 40V, Positive-QTOFsplash10-06r2-1900000000-3fe2b7a2aa846d1498e82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N6-cis-p-Coumaroylserotonin 10V, Negative-QTOFsplash10-00di-0309000000-f5fabf8a91db547434c32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N6-cis-p-Coumaroylserotonin 20V, Negative-QTOFsplash10-022a-0914000000-6ea027e67f01db5ef1612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N6-cis-p-Coumaroylserotonin 40V, Negative-QTOFsplash10-0006-6900000000-bce88a8597408f7f01742016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N6-cis-p-Coumaroylserotonin 10V, Positive-QTOFsplash10-00di-0409000000-b5e695c1496bbd99453c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N6-cis-p-Coumaroylserotonin 20V, Positive-QTOFsplash10-03fr-0902000000-36f1391fa39443f836542021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N6-cis-p-Coumaroylserotonin 40V, Positive-QTOFsplash10-0006-1900000000-9278907f3a5d0f6f91392021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N6-cis-p-Coumaroylserotonin 10V, Negative-QTOFsplash10-00di-0009000000-0a90bce16d9084968bc32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N6-cis-p-Coumaroylserotonin 20V, Negative-QTOFsplash10-00xr-1926000000-dc21115b4587fbbf850a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N6-cis-p-Coumaroylserotonin 40V, Negative-QTOFsplash10-014i-8920000000-c9f2042f64c8cc4b18eb2021-09-23Wishart 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 IDFDB017675
KNApSAcK IDC00026736
Chemspider ID4572762
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5458879
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.. .