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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:51:37 UTC
Update Date2022-03-07 02:53:27 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 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. Moschamine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Moschamine.
Structure
Data?1563862303
Synonyms
ValueSource
N-FeruloylserotoninMeSH
N-(Feruloyl)-serotonin (I)HMDB
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point115 - 117 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+183.80530932474
DeepCCS[M-H]-181.44730932474
DeepCCS[M-2H]-215.67830932474
DeepCCS[M+Na]+190.90530932474
AllCCS[M+H]+185.632859911
AllCCS[M+H-H2O]+182.632859911
AllCCS[M+NH4]+188.432859911
AllCCS[M+Na]+189.232859911
AllCCS[M-H]-186.332859911
AllCCS[M+Na-2H]-186.032859911
AllCCS[M+HCOO]-185.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MoschamineCOC1=CC(\C=C\C(=O)NCCC2=CNC3=C2C=C(O)C=C3)=CC=C1O5259.4Standard polar33892256
MoschamineCOC1=CC(\C=C\C(=O)NCCC2=CNC3=C2C=C(O)C=C3)=CC=C1O3587.0Standard non polar33892256
MoschamineCOC1=CC(\C=C\C(=O)NCCC2=CNC3=C2C=C(O)C=C3)=CC=C1O4057.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Moschamine,1TMS,isomer #1COC1=CC(/C=C/C(=O)NCCC2=C[NH]C3=CC=C(O[Si](C)(C)C)C=C23)=CC=C1O3851.0Semi standard non polar33892256
Moschamine,1TMS,isomer #2COC1=CC(/C=C/C(=O)NCCC2=C[NH]C3=CC=C(O)C=C23)=CC=C1O[Si](C)(C)C3839.5Semi standard non polar33892256
Moschamine,1TMS,isomer #3COC1=CC(/C=C/C(=O)N(CCC2=C[NH]C3=CC=C(O)C=C23)[Si](C)(C)C)=CC=C1O3815.7Semi standard non polar33892256
Moschamine,1TMS,isomer #4COC1=CC(/C=C/C(=O)NCCC2=CN([Si](C)(C)C)C3=CC=C(O)C=C23)=CC=C1O3938.0Semi standard non polar33892256
Moschamine,2TMS,isomer #1COC1=CC(/C=C/C(=O)NCCC2=C[NH]C3=CC=C(O[Si](C)(C)C)C=C23)=CC=C1O[Si](C)(C)C3842.5Semi standard non polar33892256
Moschamine,2TMS,isomer #2COC1=CC(/C=C/C(=O)N(CCC2=C[NH]C3=CC=C(O[Si](C)(C)C)C=C23)[Si](C)(C)C)=CC=C1O3718.3Semi standard non polar33892256
Moschamine,2TMS,isomer #3COC1=CC(/C=C/C(=O)NCCC2=CN([Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C23)=CC=C1O3879.8Semi standard non polar33892256
Moschamine,2TMS,isomer #4COC1=CC(/C=C/C(=O)N(CCC2=C[NH]C3=CC=C(O)C=C23)[Si](C)(C)C)=CC=C1O[Si](C)(C)C3748.9Semi standard non polar33892256
Moschamine,2TMS,isomer #5COC1=CC(/C=C/C(=O)NCCC2=CN([Si](C)(C)C)C3=CC=C(O)C=C23)=CC=C1O[Si](C)(C)C3871.6Semi standard non polar33892256
Moschamine,2TMS,isomer #6COC1=CC(/C=C/C(=O)N(CCC2=CN([Si](C)(C)C)C3=CC=C(O)C=C23)[Si](C)(C)C)=CC=C1O3860.1Semi standard non polar33892256
Moschamine,3TMS,isomer #1COC1=CC(/C=C/C(=O)N(CCC2=C[NH]C3=CC=C(O[Si](C)(C)C)C=C23)[Si](C)(C)C)=CC=C1O[Si](C)(C)C3720.6Semi standard non polar33892256
Moschamine,3TMS,isomer #1COC1=CC(/C=C/C(=O)N(CCC2=C[NH]C3=CC=C(O[Si](C)(C)C)C=C23)[Si](C)(C)C)=CC=C1O[Si](C)(C)C3709.0Standard non polar33892256
Moschamine,3TMS,isomer #2COC1=CC(/C=C/C(=O)NCCC2=CN([Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C23)=CC=C1O[Si](C)(C)C3853.1Semi standard non polar33892256
Moschamine,3TMS,isomer #2COC1=CC(/C=C/C(=O)NCCC2=CN([Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C23)=CC=C1O[Si](C)(C)C3675.0Standard non polar33892256
Moschamine,3TMS,isomer #3COC1=CC(/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)=CC=C1O3746.3Semi standard non polar33892256
Moschamine,3TMS,isomer #3COC1=CC(/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)=CC=C1O3719.6Standard non polar33892256
Moschamine,3TMS,isomer #4COC1=CC(/C=C/C(=O)N(CCC2=CN([Si](C)(C)C)C3=CC=C(O)C=C23)[Si](C)(C)C)=CC=C1O[Si](C)(C)C3782.5Semi standard non polar33892256
Moschamine,3TMS,isomer #4COC1=CC(/C=C/C(=O)N(CCC2=CN([Si](C)(C)C)C3=CC=C(O)C=C23)[Si](C)(C)C)=CC=C1O[Si](C)(C)C3679.4Standard non polar33892256
Moschamine,4TMS,isomer #1COC1=CC(/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)=CC=C1O[Si](C)(C)C3740.3Semi standard non polar33892256
Moschamine,4TMS,isomer #1COC1=CC(/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)=CC=C1O[Si](C)(C)C3520.8Standard non polar33892256
Moschamine,1TBDMS,isomer #1COC1=CC(/C=C/C(=O)NCCC2=C[NH]C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C23)=CC=C1O4137.5Semi standard non polar33892256
Moschamine,1TBDMS,isomer #2COC1=CC(/C=C/C(=O)NCCC2=C[NH]C3=CC=C(O)C=C23)=CC=C1O[Si](C)(C)C(C)(C)C4116.1Semi standard non polar33892256
Moschamine,1TBDMS,isomer #3COC1=CC(/C=C/C(=O)N(CCC2=C[NH]C3=CC=C(O)C=C23)[Si](C)(C)C(C)(C)C)=CC=C1O4060.4Semi standard non polar33892256
Moschamine,1TBDMS,isomer #4COC1=CC(/C=C/C(=O)NCCC2=CN([Si](C)(C)C(C)(C)C)C3=CC=C(O)C=C23)=CC=C1O4170.8Semi standard non polar33892256
Moschamine,2TBDMS,isomer #1COC1=CC(/C=C/C(=O)NCCC2=C[NH]C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C23)=CC=C1O[Si](C)(C)C(C)(C)C4372.5Semi standard non polar33892256
Moschamine,2TBDMS,isomer #2COC1=CC(/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)=CC=C1O4237.2Semi standard non polar33892256
Moschamine,2TBDMS,isomer #3COC1=CC(/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)=CC=C1O4354.7Semi standard non polar33892256
Moschamine,2TBDMS,isomer #4COC1=CC(/C=C/C(=O)N(CCC2=C[NH]C3=CC=C(O)C=C23)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C4255.6Semi standard non polar33892256
Moschamine,2TBDMS,isomer #5COC1=CC(/C=C/C(=O)NCCC2=CN([Si](C)(C)C(C)(C)C)C3=CC=C(O)C=C23)=CC=C1O[Si](C)(C)C(C)(C)C4337.9Semi standard non polar33892256
Moschamine,2TBDMS,isomer #6COC1=CC(/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)=CC=C1O4294.8Semi standard non polar33892256
Moschamine,3TBDMS,isomer #1COC1=CC(/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)=CC=C1O[Si](C)(C)C(C)(C)C4451.8Semi standard non polar33892256
Moschamine,3TBDMS,isomer #1COC1=CC(/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)=CC=C1O[Si](C)(C)C(C)(C)C4254.2Standard non polar33892256
Moschamine,3TBDMS,isomer #2COC1=CC(/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)=CC=C1O[Si](C)(C)C(C)(C)C4566.5Semi standard non polar33892256
Moschamine,3TBDMS,isomer #2COC1=CC(/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)=CC=C1O[Si](C)(C)C(C)(C)C4264.6Standard non polar33892256
Moschamine,3TBDMS,isomer #3COC1=CC(/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)=CC=C1O4420.6Semi standard non polar33892256
Moschamine,3TBDMS,isomer #3COC1=CC(/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)=CC=C1O4201.3Standard non polar33892256
Moschamine,3TBDMS,isomer #4COC1=CC(/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)=CC=C1O[Si](C)(C)C(C)(C)C4436.5Semi standard non polar33892256
Moschamine,3TBDMS,isomer #4COC1=CC(/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)=CC=C1O[Si](C)(C)C(C)(C)C4202.5Standard non polar33892256
Moschamine,4TBDMS,isomer #1COC1=CC(/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)=CC=C1O[Si](C)(C)C(C)(C)C4605.3Semi standard non polar33892256
Moschamine,4TBDMS,isomer #1COC1=CC(/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)=CC=C1O[Si](C)(C)C(C)(C)C4123.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Moschamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-054k-0923000000-3934de869b02cac9424e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Moschamine GC-MS (2 TMS) - 70eV, Positivesplash10-001i-1060900000-dec25e50f91c4f3b32032017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Moschamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Moschamine 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 - Moschamine 10V, Positive-QTOFsplash10-0fb9-0903000000-30b46bfb0c5639e254402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moschamine 20V, Positive-QTOFsplash10-056r-0900000000-59a7ae68937dab6348b42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moschamine 40V, Positive-QTOFsplash10-0002-0900000000-9b70509ceb90d4ee77ec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moschamine 10V, Negative-QTOFsplash10-0udi-0309000000-705280dc98eedf985ae92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moschamine 20V, Negative-QTOFsplash10-0fb9-0905000000-5ce4ff9eac456f9b43932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moschamine 40V, Negative-QTOFsplash10-002f-3900000000-f211e7b93512d3a93f762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moschamine 10V, Positive-QTOFsplash10-0udi-0309000000-9a24f05f428938809d602021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moschamine 20V, Positive-QTOFsplash10-0ik9-0904000000-1c82ce2f38c4ec8760862021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moschamine 40V, Positive-QTOFsplash10-01rx-1900000000-3797e8ab2793cbc688752021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moschamine 10V, Negative-QTOFsplash10-0udi-0009000000-5910fb854608b2191a932021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moschamine 20V, Negative-QTOFsplash10-0f8j-0913000000-2b67e8c3bae5fde39d5e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moschamine 40V, Negative-QTOFsplash10-001j-0923000000-bdfffd81dab971d98ce22021-09-24Wishart 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 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
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.. .