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Showing Compound Limocitrol (FDB016819)

Record Information
Version1.0
Creation date2010-04-08 22:12:40 UTC
Update date2019-11-26 03:13:50 UTC
Primary IDFDB016819
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLimocitrol
DescriptionLimocitrol 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, limocitrol is considered to be a flavonoid. Limocitrol has been detected, but not quantified in, citrus and lemons (Citrus limon). This could make limocitrol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Limocitrol.
CAS Number549-10-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3,4',5,7-Tetrahydroxy-3',6,8-trimethoxyflavoneHMDB
Limocitroldb_source
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP2.02ALOGPS
logP1.99ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)6.45ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area134.91 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity94.27 m³·mol⁻¹ChemAxon
Polarizability36.22 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H16O9
IUPAC name3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,8-dimethoxy-4H-chromen-4-one
InChI IdentifierInChI=1S/C18H16O9/c1-24-9-6-7(4-5-8(9)19)15-13(22)11(20)10-12(21)17(25-2)14(23)18(26-3)16(10)27-15/h4-6,19,21-23H,1-3H3
InChI KeyLCKHNFJHVWUHTR-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C=CC(=C1)C1=C(O)C(=O)C2=C(O1)C(OC)=C(O)C(OC)=C2O
Average Molecular Weight376.3142
Monoisotopic Molecular Weight376.07943211
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
  • 6-methoxyflavonoid-skeleton
  • 8-methoxyflavonoid-skeleton
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Chromone
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Phenol ether
  • Anisole
  • Phenoxy compound
  • Methoxybenzene
  • Pyranone
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 57.45%; H 4.29%; O 38.26%DFC
Melting PointMp 221-222° (210-211°)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-MSLimocitrol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-0209000000-93f1fb58bcbe798bdc96Spectrum
Predicted GC-MSLimocitrol, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0kfw-1013039000-3b149966c5658ead50e6Spectrum
Predicted GC-MSLimocitrol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-180ad41b6dc71a65dc832016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0009000000-d75c79a9e262a578d16d2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-0928000000-d75b7c456786dc53a93b2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-1b16d8fb831c88f1d0db2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0009000000-93c2a5b876f381b4a2b82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-7897000000-76477852f976c540e0942016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-4389f520d5a46c87493e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0049000000-afeaeab71782110cadb32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dj-1933000000-7171f0fd02ad113c20cf2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-b6992d0ca4afb85cf2cc2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0009000000-93cf5a585ebab75d4c922021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0400-2395000000-f7925751adbf9dcd99b62021-09-22View Spectrum
NMRNot Available
ChemSpider ID10228270
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID12311234
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB37691
CRC / DFC (Dictionary of Food Compounds) IDCBS65-J:KTK70-Z
EAFUS IDNot Available
Dr. Duke IDLIMOCITROL
BIGG IDNot Available
KNApSAcK IDC00004792
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.