| Common Name |
Limocitrin
| Description |
Limocitrin is found in citrus. Limocitrin is a constituent of citrus fruit peels.Limocitrin belongs to the family of Flavonols. These are compounds that has the 3-hydroxyflavone backbone.
| Structure |
MOLSDFPDBSMILESInChI
Structure for HMDB29516 (Limocitrin)
| Synonyms |
| Value |
Source |
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
| Chemical Formlia |
C17H14O8
| Average Molecliar Weight |
346.2883
| Monoisotopic Molecliar Weight |
346.068867424
| IUPAC Name |
3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4H-chromen-4-one
| Traditional Name |
limocitrin
| CAS Registry Number |
489-33-8
| SMILES |
COC1=CC(=CC=C1O)C1=C(O)C(=O)C2=C(O1)C(OC)=C(O)C=C2O
| InChI Identifier |
InChI=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 Key |
IBXCKSUZOFKGSB-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of organic compounds known as flavonols. These are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.
| Kingdom |
Organic compounds
| Super Class |
Phenylpropanoids and polyketides
| Class |
Flavonoids
| Sub Class |
Flavones
| Direct Parent |
Flavonols
| Alternative Parents |
8-O-methylated flavonoids
3-O-methylated flavonoids
7-hydroxyflavonoids
5-hydroxyflavonoids
4-hydroxyflavonoids
3-hydroxyflavonoids
Chromones
Methoxyphenols
Hydroxyquinols and derivatives
Resorcinols
Methoxybenzenes
Anisoles
Pyranones and derivatives
Alkyl aryl ethers
Vinylogous acids
Heteroaromatic compounds
Polyols
Oxacyclic compounds
Hydrocarbon derivatives
| Substituents |
Methoxyflavonoid skeleton
3-hydroxyflavone
8-methoxyflavonoid-skeleton
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3-hydroxyflavonoid
Chromone
1-benzopyran
Methoxyphenol
Benzopyran
Hydroxyquinol derivative
Methoxybenzene
Resorcinol
Phenol ether
Anisole
Pyranone
Phenol
Alkyl aryl ether
Benzenoid
Pyran
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Polyol
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
Flavones and Flavonols (LMPK12113241 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
Food
| Biofunction |
Not Available
| Application |
Nutrient
| Cellliar locations |
Cytoplasm
Extracellliar
| Physical Properties |
| State |
Not Available
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point274 – 275 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.14 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity87.81 m3·mol-1ChemAxon
Polarizability33.26 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| LC-MS/MS |
LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-0002-0009000000-68df39c49592dae61826View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-001i-0009000000-92129baf970b23db0539View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-03y3-0950000000-b6df732dc8a613daa6f4View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-0002-0009000000-095643a6e479babccf52View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-000t-0009000000-f1352a438263d2a9a892View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-0002-0009000000-f4088022d7a1ce5904d4View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-0002-0009000000-072cbfd0f75bab2c8282View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-0ue9-1952000000-c8c1fc3ae74487ec1567View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-0002-0009000000-e4f48dc3b9efce5f0790View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-0002-0029000000-4b7f4346f71d27eecb9bView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-01bc-2982000000-a396d10514a1787c57c5View in MoNA
| Biological Properties |
| Cellliar Locations |
Cytoplasm
Extracellliar
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB000652
| KNApSAcK ID |
C00004731
| Chemspider ID |
4590163
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB29516
| Metagene Link |
HMDB29516
| METLIN ID |
Not Available
| PubChem Compound |
5489485
| PDB ID |
Not Available
| ChEBI ID |
542813
Product: PF-04979064
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
|
PMID: 23880372
