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Showing Compound Limocitrin (FDB000652)

Record Information
Version1.0
Creation date2010-04-08 22:04:39 UTC
Update date2020-02-24 19:10:11 UTC
Primary IDFDB000652
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLimocitrin
DescriptionLimocitrin belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, limocitrin is considered to be a flavonoid. Limocitrin has been detected, but not quantified in, citrus and lemons (Citrus limon). This could make limocitrin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Limocitrin.
CAS Number489-33-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4H-1-benzopyran-4-one, 9ciHMDB
4',5,7-Trihydroxy-3',8-dimethoxyflavonolHMDB
Gossypetin 3',8-dimethyl etherHMDB
SedoflorigeninHMDB
3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4H-1-benzopyran-4-one, 9CIdb_source
3',8-Dimethoxygossypetinmanual
Limocitrindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP1.97ALOGPS
logP2.14ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)6.96ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area125.68 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity87.81 m³·mol⁻¹ChemAxon
Polarizability33.26 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H14O8
IUPAC name3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4H-chromen-4-one
InChI IdentifierInChI=1S/C17H14O8/c1-23-11-5-7(3-4-8(11)18)15-14(22)13(21)12-9(19)6-10(20)16(24-2)17(12)25-15/h3-6,18-20,22H,1-2H3
InChI KeyIBXCKSUZOFKGSB-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(=CC=C1O)C1=C(O)C(=O)C2=C(O1)C(OC)=C(O)C=C2O
Average Molecular Weight346.2883
Monoisotopic Molecular Weight346.068867424
Classification
Description Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavonols
Alternative Parents
Substituents
  • 3-hydroxyflavone
  • 3p-methoxyflavonoid-skeleton
  • 8-methoxyflavonoid-skeleton
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Chromone
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Phenoxy compound
  • Pyranone
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 58.96%; H 4.07%; O 36.96%DFC
Melting PointMp 274-275°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSLimocitrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-0319000000-916e78a0249246554fa6Spectrum
Predicted GC-MSLimocitrin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01b9-2312089000-167f74930f837df18f1fSpectrum
Predicted GC-MSLimocitrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0009000000-68df39c49592dae618262017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0009000000-92129baf970b23db05392017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03y3-0950000000-b6df732dc8a613daa6f42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0009000000-095643a6e479babccf522017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000t-0009000000-f1352a438263d2a9a8922017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-080474eeeaacd09b4a872021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-84db9ce8c659ba58f2032021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000t-0009000000-f1352a438263d2a9a8922021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-095643a6e479babccf522021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-03y3-0950000000-b6df732dc8a613daa6f42021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-f4088022d7a1ce5904d42015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0009000000-072cbfd0f75bab2c82822015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-1952000000-c8c1fc3ae74487ec15672015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-e4f48dc3b9efce5f07902015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0029000000-4b7f4346f71d27eecb9b2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01bc-2982000000-a396d10514a1787c57c52015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-24b80c82c41a998b9ea52021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0009000000-b4bb1ffb9bc021542b412021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ls-1903000000-cefe5a930f54d156cf122021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-4173ab4cf400ed4c20372021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0439000000-90b8a03523c50fc7a1782021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00yi-1921000000-ecebb4a8ac8569f176c32021-09-25View Spectrum
NMRNot Available
ChemSpider ID4590163
ChEMBL IDCHEMBL452488
KEGG Compound IDNot Available
Pubchem Compound ID5489485
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB29516
CRC / DFC (Dictionary of Food Compounds) IDBFK50-E:BFK50-E
EAFUS IDNot Available
Dr. Duke IDLIMOCITRIN
BIGG IDNot Available
KNApSAcK IDC00004731
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.