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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 18:10:10 UTC
Update Date2022-09-22 18:34:25 UTC
HMDB IDHMDB0033435
Secondary Accession Numbers
  • HMDB33435
Metabolite Identification
Common Name(±)-Aegeline
Description(±)-Aegeline, also known as aegeline, belongs to the class of organic compounds known as cinnamic acid amides. These are amides of cinnamic acids. Cinnamic acid is an aromatic compound containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid (±)-Aegeline has been detected, but not quantified in, fruits. This could make (±)-aegeline a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (±)-Aegeline.
Structure
Data?1563862405
Synonyms
ValueSource
AegelineHMDB
N-(2-Hydroxy-2(4-methoxyphenyl)ethyl)-3-phenyl-2-propenamideHMDB
(2E)-N-[2-Hydroxy-2-(4-methoxyphenyl)ethyl]-3-phenylprop-2-enimidateHMDB
Chemical FormulaC18H19NO3
Average Molecular Weight297.3484
Monoisotopic Molecular Weight297.136493479
IUPAC Name(2E)-N-[2-hydroxy-2-(4-methoxyphenyl)ethyl]-3-phenylprop-2-enamide
Traditional Name(2E)-N-[2-hydroxy-2-(4-methoxyphenyl)ethyl]-3-phenylprop-2-enamide
CAS Registry Number37791-13-2
SMILES
COC1=CC=C(C=C1)C(O)CNC(=O)\C=C\C1=CC=CC=C1
InChI Identifier
InChI=1S/C18H19NO3/c1-22-16-10-8-15(9-11-16)17(20)13-19-18(21)12-7-14-5-3-2-4-6-14/h2-12,17,20H,13H2,1H3,(H,19,21)/b12-7+
InChI KeyQRFDENJATPJOKG-KPKJPENVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cinnamic acid amides. These are amides of cinnamic acids. Cinnamic acid is an aromatic compound containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassCinnamic acid amides
Direct ParentCinnamic acid amides
Alternative Parents
Substituents
  • Cinnamic acid amide
  • Anisole
  • Phenol ether
  • Styrene
  • Methoxybenzene
  • Phenoxy compound
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Ether
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point176 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP2.48ALOGPS
logP2.49ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)14.09ChemAxon
pKa (Strongest Basic)1.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.56 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity86.82 m³·mol⁻¹ChemAxon
Polarizability32.94 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+169.84530932474
DeepCCS[M-H]-167.48730932474
DeepCCS[M-2H]-200.89330932474
DeepCCS[M+Na]+176.1230932474
AllCCS[M+H]+172.932859911
AllCCS[M+H-H2O]+169.532859911
AllCCS[M+NH4]+176.232859911
AllCCS[M+Na]+177.132859911
AllCCS[M-H]-175.132859911
AllCCS[M+Na-2H]-175.032859911
AllCCS[M+HCOO]-175.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(??)-AegelineCOC1=CC=C(C=C1)C(O)CNC(=O)\C=C\C1=CC=CC=C13955.8Standard polar33892256
(??)-AegelineCOC1=CC=C(C=C1)C(O)CNC(=O)\C=C\C1=CC=CC=C12478.5Standard non polar33892256
(??)-AegelineCOC1=CC=C(C=C1)C(O)CNC(=O)\C=C\C1=CC=CC=C12988.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(??)-Aegeline,1TMS,isomer #1COC1=CC=C(C(CNC(=O)/C=C/C2=CC=CC=C2)O[Si](C)(C)C)C=C12841.9Semi standard non polar33892256
(??)-Aegeline,1TMS,isomer #2COC1=CC=C(C(O)CN(C(=O)/C=C/C2=CC=CC=C2)[Si](C)(C)C)C=C12829.6Semi standard non polar33892256
(±)-Aegeline,2TMS,isomer #1COC1=CC=C(C(CN(C(=O)/C=C/C2=CC=CC=C2)[Si](C)(C)C)O[Si](C)(C)C)C=C12791.3Semi standard non polar33892256
(±)-Aegeline,2TMS,isomer #1COC1=CC=C(C(CN(C(=O)/C=C/C2=CC=CC=C2)[Si](C)(C)C)O[Si](C)(C)C)C=C12549.3Standard non polar33892256
(??)-Aegeline,1TBDMS,isomer #1COC1=CC=C(C(CNC(=O)/C=C/C2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)C=C13109.4Semi standard non polar33892256
(??)-Aegeline,1TBDMS,isomer #2COC1=CC=C(C(O)CN(C(=O)/C=C/C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C13068.3Semi standard non polar33892256
(±)-Aegeline,2TBDMS,isomer #1COC1=CC=C(C(CN(C(=O)/C=C/C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C13254.9Semi standard non polar33892256
(±)-Aegeline,2TBDMS,isomer #1COC1=CC=C(C(CN(C(=O)/C=C/C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C12991.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (±)-Aegeline GC-MS (Non-derivatized) - 70eV, Positivesplash10-001r-1910000000-633878445dce087383752017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-Aegeline GC-MS (1 TMS) - 70eV, Positivesplash10-0ff0-5931000000-c6c10b6edd7272ffa2ab2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-Aegeline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - (±)-Aegeline , positive-QTOFsplash10-0f89-0900000000-4d557981266b31d04b422017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (±)-Aegeline , positive-QTOFsplash10-0ue9-0900000000-0b319c3793f21b0b44232017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Aegeline 10V, Positive-QTOFsplash10-00ls-0970000000-836f8f28f565fd62efd22016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Aegeline 20V, Positive-QTOFsplash10-00l2-0910000000-de537485ed72ae9f3dae2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Aegeline 40V, Positive-QTOFsplash10-0f7t-0900000000-8eee608fa7e5e46881952016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Aegeline 10V, Negative-QTOFsplash10-0002-0390000000-42b16adcb965e754fb7f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Aegeline 20V, Negative-QTOFsplash10-002b-1950000000-e25d0adca22cf688ec382016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Aegeline 40V, Negative-QTOFsplash10-0006-5900000000-6397133471ec8dfe82c92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Aegeline 10V, Negative-QTOFsplash10-0002-0190000000-872a22a5097454ff34932021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Aegeline 20V, Negative-QTOFsplash10-0f97-4950000000-e7d04767984589f291c62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Aegeline 40V, Negative-QTOFsplash10-0w4l-7950000000-1f2cb789088ad05307cb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Aegeline 10V, Positive-QTOFsplash10-001i-0920000000-5c98a88f3b31cf384ee72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Aegeline 20V, Positive-QTOFsplash10-0udi-0900000000-34f40e51b77000b522562021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Aegeline 40V, Positive-QTOFsplash10-0udi-1900000000-a61e2784575df8e72ca72021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011473
KNApSAcK IDNot Available
Chemspider ID10296259
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15558419
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.. .