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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:52:53 UTC
Update Date2021-10-13 06:28:28 UTC
HMDB IDHMDB0032952
Secondary Accession Numbers
  • HMDB32952
Metabolite Identification
Common NameCitropten
DescriptionCitropten belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Citropten has been detected, but not quantified in, a few different foods, such as citrus, lemons (Citrus limon), and limes (Citrus aurantiifolia). This could make citropten a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Citropten.
Structure
Data?1563862330
Synonyms
ValueSource
57-DimethoxycoumarinChEMBL, HMDB
5, 7-DimethoxycoumarinHMDB
5,7-Dimethoxy-2-benzopyroneHMDB
5,7-Dimethoxy-2H-1-benzo-pyran-2-oneHMDB
5,7-Dimethoxy-2H-1-benzopyran-2-oneHMDB
5,7-Dimethoxy-2H-chromen-2-oneHMDB
5,7-Dimethoxy-coumarinHMDB
5,7-DimethoxycoumarinHMDB
5,7-Dimethyloxy-2H-1-benzopyran-2-oneHMDB
CitrapteneHMDB
CitropteneHMDB
LimetinHMDB
LimettinHMDB, MeSH
OmphamurrayinMeSH, HMDB
CitroptenMeSH
Chemical FormulaC11H10O4
Average Molecular Weight206.1947
Monoisotopic Molecular Weight206.057908808
IUPAC Name5,7-dimethoxy-2H-chromen-2-one
Traditional Namelimettin
CAS Registry Number487-06-9
SMILES
COC1=CC(OC)=C2C=CC(=O)OC2=C1
InChI Identifier
InChI=1S/C11H10O4/c1-13-7-5-9(14-2)8-3-4-11(12)15-10(8)6-7/h3-6H,1-2H3
InChI KeyNXJCRELRQHZBQA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassNot Available
Direct ParentCoumarins and derivatives
Alternative Parents
Substituents
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point147 °CNot Available
Boiling Point388.14 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1510 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.891 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available138.276http://allccs.zhulab.cn/database/detail?ID=AllCCS00001435
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.42 g/LALOGPS
logP10(1.79) g/LALOGPS
logP10(1.47) g/LChemAxon
logS10(-2.7) g/LALOGPS
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area44.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity54.48 m³·mol⁻¹ChemAxon
Polarizability20.36 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
DarkChem[M+H]+147.39331661259
DarkChem[M-H]-146.54731661259
DeepCCS[M+H]+143.5230932474
DeepCCS[M-H]-141.16230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CitroptenCOC1=CC(OC)=C2C=CC(=O)OC2=C12928.0Standard polar33892256
CitroptenCOC1=CC(OC)=C2C=CC(=O)OC2=C11873.0Standard non polar33892256
CitroptenCOC1=CC(OC)=C2C=CC(=O)OC2=C11984.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Citropten GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-1910000000-c835aeb89534cb54cc3e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citropten 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 - Citropten LC-ESI-qTof , Positive-QTOFsplash10-01ot-0900000000-2dcf0452621780fddfa12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citropten , positive-QTOFsplash10-01ot-0900000000-2dcf0452621780fddfa12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citropten 90V, Positive-QTOFsplash10-01ow-6900000000-80039ad9cbf6fe601dc92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citropten 45V, Positive-QTOFsplash10-0a4i-0790000000-0809e8c80bf4720a79f12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citropten 30V, Positive-QTOFsplash10-0a4i-0090000000-edeb0682b6bd14a0cb382021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citropten 60V, Positive-QTOFsplash10-06xx-1910000000-7a196af151e0b2edcb7b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citropten 75V, Positive-QTOFsplash10-03kd-2900000000-342d0e90014fcf4fe22b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citropten 15V, Positive-QTOFsplash10-0a4i-0090000000-8376dd6be91911fa85a22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citropten 40V, Positive-QTOFsplash10-0002-0900000000-9179167a94bd4e49b49f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citropten 10V, Positive-QTOFsplash10-0a4i-0190000000-9d2c3a95cabf01743b142021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citropten 20V, Positive-QTOFsplash10-0a4i-0940000000-e026fa3296c7bc198a372021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citropten 10V, Positive-QTOFsplash10-0a4i-0090000000-c860a23bde585864175d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citropten 20V, Positive-QTOFsplash10-0a4i-0190000000-a2abe886f1f1a2fdac282015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citropten 40V, Positive-QTOFsplash10-0bw9-1900000000-2d825b207f50100707362015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citropten 10V, Negative-QTOFsplash10-0a4i-0190000000-1994a17fe4b5a2038f442015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citropten 20V, Negative-QTOFsplash10-0a4i-0490000000-86ce0884f21d1559ccc42015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citropten 40V, Negative-QTOFsplash10-06si-1900000000-1f5b2f110cebe709cef22015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citropten 10V, Negative-QTOFsplash10-0a4i-0090000000-99c859898d8c3407680e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citropten 20V, Negative-QTOFsplash10-0a4i-0190000000-b08bc5f7c3a63eada3902021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citropten 40V, Negative-QTOFsplash10-0092-0900000000-6148648e8dd05417fcb92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citropten 10V, Positive-QTOFsplash10-0a4i-0090000000-d59b09fd60f8eef417932021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citropten 20V, Positive-QTOFsplash10-0a4i-0090000000-300b5239d4467b9990372021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citropten 40V, Positive-QTOFsplash10-06r2-2900000000-fd0319bb3609e0d6657d2021-09-24Wishart 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 IDFDB010938
KNApSAcK IDNot Available
Chemspider ID2673
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCitropten
METLIN IDNot Available
PubChem Compound2775
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1208211
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.. .