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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:47:25 UTC
Update Date2023-02-21 17:25:27 UTC
HMDB IDHMDB0036627
Secondary Accession Numbers
  • HMDB36627
Metabolite Identification
Common NameEugenin
DescriptionEugenin belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety. Eugenin has been detected, but not quantified in, several different foods, such as carrots (Daucus carota ssp. sativus), cloves (Syzygium aromaticum), herbs and spices, java plums (Syzygium cumini), and wild carrots (Daucus carota). This could make eugenin a potential biomarker for the consumption of these foods. Eugenin 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 small amount of articles have been published on Eugenin.
Structure
Data?1677000327
Synonyms
ValueSource
5-Hydroxy-7-methoxy-2-methyl-4H-1-benzopyran-4-oneChEBI
5-Hydroxy-7-methoxy-2-methylchromen-4-oneChEBI
5-Hydroxy-7-methoxy-2-methylchromoneChEBI
2-Methyl-5-hydroxy-7-methoxychromoneKegg
5-Hydroxy-7-methoxy-2-methyl-4H-chromen-4-oneHMDB
5-Hydroxy-7-methoxy-2-methyl-chromoneHMDB
5-Hydroxy-7-methoxy-2-methylchroneHMDB
Chemical FormulaC11H10O4
Average Molecular Weight206.1947
Monoisotopic Molecular Weight206.057908808
IUPAC Name5-hydroxy-7-methoxy-2-methyl-4H-chromen-4-one
Traditional Nameeugenin
CAS Registry Number480-34-2
SMILES
COC1=CC(O)=C2C(=O)C=C(C)OC2=C1
InChI Identifier
InChI=1S/C11H10O4/c1-6-3-8(12)11-9(13)4-7(14-2)5-10(11)15-6/h3-5,13H,1-2H3
InChI KeySUTUBQHKZRNZRA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct ParentChromones
Alternative Parents
Substituents
  • Chromone
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Ether
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • 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 Point119 - 120 °CNot Available
Boiling Point389.00 to 390.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility812.3 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.661 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.91 g/LALOGPS
logP1.98ALOGPS
logP2.06ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)8.58ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity55.55 m³·mol⁻¹ChemAxon
Polarizability20.55 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]+149.78530932474
DeepCCS[M-H]-147.42730932474
DeepCCS[M-2H]-180.71130932474
DeepCCS[M+Na]+155.87830932474
AllCCS[M+H]+142.832859911
AllCCS[M+H-H2O]+138.432859911
AllCCS[M+NH4]+146.832859911
AllCCS[M+Na]+148.032859911
AllCCS[M-H]-144.032859911
AllCCS[M+Na-2H]-144.032859911
AllCCS[M+HCOO]-144.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EugeninCOC1=CC(O)=C2C(=O)C=C(C)OC2=C13041.9Standard polar33892256
EugeninCOC1=CC(O)=C2C(=O)C=C(C)OC2=C11952.4Standard non polar33892256
EugeninCOC1=CC(O)=C2C(=O)C=C(C)OC2=C11911.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Eugenin,1TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C2C(=O)C=C(C)OC2=C12118.5Semi standard non polar33892256
Eugenin,1TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=C(C)OC2=C12366.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Eugenin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a73-0920000000-166493955765f2af796e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Eugenin GC-MS (1 TMS) - 70eV, Positivesplash10-08mi-3290000000-44e8533816a77387e0f62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Eugenin 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 - Eugenin 10V, Positive-QTOFsplash10-0a4i-0190000000-9d3284c6c48660f910cd2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenin 20V, Positive-QTOFsplash10-0a4i-0290000000-b48df3b08073c0ba0a5d2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenin 40V, Positive-QTOFsplash10-05n0-1900000000-dfa3f428a8c0211cd7d22016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenin 10V, Negative-QTOFsplash10-0a4i-0090000000-4c90595e1fdeeb6c4dde2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenin 20V, Negative-QTOFsplash10-0a4i-0190000000-b2df505f2b6732b8640c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenin 40V, Negative-QTOFsplash10-00rj-5900000000-36d8f1c802565e5005762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenin 10V, Positive-QTOFsplash10-0a4i-0090000000-d59b09fd60f8eef417932021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenin 20V, Positive-QTOFsplash10-0a4i-0190000000-d356be22aa951378cb272021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenin 40V, Positive-QTOFsplash10-007d-4900000000-3fa044fbf762e6d6061e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenin 10V, Negative-QTOFsplash10-0a4i-0090000000-99c859898d8c3407680e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenin 20V, Negative-QTOFsplash10-0a4i-0090000000-99c859898d8c3407680e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenin 40V, Negative-QTOFsplash10-014l-9800000000-8fccbe606d2054e3d3812021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB015545
KNApSAcK IDC00030226
Chemspider ID9777
KEGG Compound IDC20210
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEugenin
METLIN IDNot Available
PubChem Compound10189
PDB IDNot Available
ChEBI ID67374
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1500591
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.. .