Record Information
Version1.0
Creation date2010-04-08 22:09:16 UTC
Update date2018-01-23 19:11:06 UTC
Primary IDFDB010726
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNb-trans-Feruloylserotonin
DescriptionAlkaloid from Carthamus tinctorius (safflower). Nb-trans-Feruloylserotonin is found in fats and oils and herbs and spices.
CAS Number68573-23-9
Structure
Thumb
Synonyms
SynonymSource
N-(Feruloyl)-serotonin (I)HMDB
N-FeruloylserotoninHMDB
NB-(e)-FeruloylserotoninHMDB
Tryptamine, N-feruloylHMDB
MoschamineChEBI
Nb-(E)-Feruloylserotonindb_source
Nb-trans-Feruloylserotoninmanual
Predicted Properties
PropertyValueSource
Water Solubility0.0078 g/LALOGPS
logP2.91ALOGPS
logP2.9ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)9.39ChemAxon
pKa (Strongest Basic)1.21ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area94.58 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity100.66 m³·mol⁻¹ChemAxon
Polarizability38.18 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H20N2O4
IUPAC name(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
InChI IdentifierInChI=1S/C20H20N2O4/c1-26-19-10-13(2-6-18(19)24)3-7-20(25)21-9-8-14-12-22-17-5-4-15(23)11-16(14)17/h2-7,10-12,22-24H,8-9H2,1H3,(H,21,25)/b7-3+
InChI KeyWGHKJYWENWLOMY-XVNBXDOJSA-N
Isomeric SMILESCOC1=CC(\C=C\C(=O)NCCC2=CNC3=C2C=C(O)C=C3)=CC=C1O
Average Molecular Weight352.3838
Monoisotopic Molecular Weight352.142307138
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
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid or derivatives
  • Cinnamic acid amide
  • Methoxyphenol
  • Hydroxyindole
  • 3-alkylindole
  • Indole
  • Phenol ether
  • Methoxybenzene
  • Styrene
  • Anisole
  • Phenoxy compound
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Ether
  • Carboxylic acid derivative
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 68.17%; H 5.72%; N 7.95%; O 18.16%DFC
Melting PointMp 115-117°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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054k-0923000000-3934de869b02cac9424eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-1060900000-dec25e50f91c4f3b3203View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fb9-0903000000-30b46bfb0c5639e25440View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0900000000-59a7ae68937dab6348b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0900000000-9b70509ceb90d4ee77ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0309000000-705280dc98eedf985ae9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-0905000000-5ce4ff9eac456f9b4393View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-3900000000-f211e7b93512d3a93f76View in MoNA
ChemSpider ID4766454
ChEMBL IDCHEMBL564482
KEGG Compound IDNot Available
Pubchem Compound ID5969616
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB32759
CRC / DFC (Dictionary of Food Compounds) IDHDV23-B:FOF81-S
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00026737
HET 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