You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:51:37 UTC
Update Date2019-07-23 06:11:43 UTC
HMDB IDHMDB0032759
Secondary Accession Numbers
  • HMDB32759
Metabolite Identification
Common NameMoschamine
DescriptionMoschamine 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. Moschamine is a moderately basic compound (based on its pKa). Outside of the human body, moschamine has been detected, but not quantified in, fats and oils and herbs and spices. This could make moschamine a potential biomarker for the consumption of these foods. Chemically, it is an amide formed between serotonin and ferulic acid. N-Feruloylserotonin an alkaloid and polyphenol found in safflower seed. It has in vitro anti-atherogenic activity.
Structure
Data?1563862303
Synonyms
ValueSource
N-(Feruloyl)-serotonin (I)HMDB
N-FeruloylserotoninHMDB
NB-(e)-FeruloylserotoninHMDB
Tryptamine, N-feruloylHMDB
MoschamineChEBI
Chemical FormulaC20H20N2O4
Average Molecular Weight352.3838
Monoisotopic Molecular Weight352.142307138
IUPAC Name(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
Traditional Name(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
CAS Registry Number68573-23-9
SMILES
COC1=CC(\C=C\C(=O)NCCC2=CNC3=C2C=C(O)C=C3)=CC=C1O
InChI Identifier
InChI=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
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
  • 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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point115 - 117 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054k-0923000000-3934de869b02cac9424eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-1060900000-dec25e50f91c4f3b3203Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fb9-0903000000-30b46bfb0c5639e25440Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0900000000-59a7ae68937dab6348b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0900000000-9b70509ceb90d4ee77ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0309000000-705280dc98eedf985ae9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-0905000000-5ce4ff9eac456f9b4393Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-3900000000-f211e7b93512d3a93f76Spectrum
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 IDFDB010726
KNApSAcK IDC00026737
Chemspider ID4766454
KEGG Compound IDNot Available
BioCyc IDCPD-8935
BiGG IDNot Available
Wikipedia LinkN-Feruloylserotonin
METLIN IDNot Available
PubChem Compound5969616
PDB IDNot Available
ChEBI ID85158
Food Biomarker OntologyNot Available
VMH 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.. .