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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:54 UTC
Update Date2022-03-07 02:52:11 UTC
HMDB IDHMDB0029516
Secondary Accession Numbers
  • HMDB29516
Metabolite Identification
Common 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.
Structure
Data?1582753429
Synonyms
ValueSource
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 FormulaC17H14O8
Average Molecular Weight346.2883
Monoisotopic Molecular Weight346.068867424
IUPAC Name3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-4H-chromen-4-one
Traditional Namelimocitrin
CAS Registry Number489-33-8
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 KeyIBXCKSUZOFKGSB-UHFFFAOYSA-N
Chemical Taxonomy
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

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point274 - 275 °CNot Available
Boiling Point621.20 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility275.7 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.020 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+179.2931661259
DarkChem[M-H]-180.82831661259
DeepCCS[M+H]+179.65430932474
DeepCCS[M-H]-177.29630932474
DeepCCS[M-2H]-211.40730932474
DeepCCS[M+Na]+186.63430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LimocitrinCOC1=CC(=CC=C1O)C1=C(O)C(=O)C2=C(O1)C(OC)=C(O)C=C2O5321.7Standard polar33892256
LimocitrinCOC1=CC(=CC=C1O)C1=C(O)C(=O)C2=C(O1)C(OC)=C(O)C=C2O3325.9Standard non polar33892256
LimocitrinCOC1=CC(=CC=C1O)C1=C(O)C(=O)C2=C(O1)C(OC)=C(O)C=C2O3249.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Limocitrin,1TMS,isomer #1COC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O)C(OC)=C3O2)=CC=C1O[Si](C)(C)C3307.6Semi standard non polar33892256
Limocitrin,1TMS,isomer #2COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C(O)C(OC)=C3O2)=CC=C1O3303.5Semi standard non polar33892256
Limocitrin,1TMS,isomer #3COC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O[Si](C)(C)C)C(OC)=C3O2)=CC=C1O3315.4Semi standard non polar33892256
Limocitrin,1TMS,isomer #4COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C(OC)=C3O2)=CC=C1O3366.1Semi standard non polar33892256
Limocitrin,2TMS,isomer #1COC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O[Si](C)(C)C)C(OC)=C3O2)=CC=C1O[Si](C)(C)C3194.2Semi standard non polar33892256
Limocitrin,2TMS,isomer #2COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C(OC)=C3O2)=CC=C1O[Si](C)(C)C3275.1Semi standard non polar33892256
Limocitrin,2TMS,isomer #3COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C(O)C(OC)=C3O2)=CC=C1O[Si](C)(C)C3167.1Semi standard non polar33892256
Limocitrin,2TMS,isomer #4COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C(O[Si](C)(C)C)C(OC)=C3O2)=CC=C1O3163.4Semi standard non polar33892256
Limocitrin,2TMS,isomer #5COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C(OC)=C3O2)=CC=C1O3268.8Semi standard non polar33892256
Limocitrin,2TMS,isomer #6COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(OC)=C3O2)=CC=C1O3286.0Semi standard non polar33892256
Limocitrin,3TMS,isomer #1COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(OC)=C3O2)=CC=C1O[Si](C)(C)C3180.0Semi standard non polar33892256
Limocitrin,3TMS,isomer #2COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C(O[Si](C)(C)C)C(OC)=C3O2)=CC=C1O[Si](C)(C)C3102.1Semi standard non polar33892256
Limocitrin,3TMS,isomer #3COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C(OC)=C3O2)=CC=C1O[Si](C)(C)C3188.7Semi standard non polar33892256
Limocitrin,3TMS,isomer #4COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(OC)=C3O2)=CC=C1O3188.2Semi standard non polar33892256
Limocitrin,4TMS,isomer #1COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(OC)=C3O2)=CC=C1O[Si](C)(C)C3158.2Semi standard non polar33892256
Limocitrin,1TBDMS,isomer #1COC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O)C(OC)=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3577.2Semi standard non polar33892256
Limocitrin,1TBDMS,isomer #2COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(O)C(OC)=C3O2)=CC=C1O3569.6Semi standard non polar33892256
Limocitrin,1TBDMS,isomer #3COC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3O2)=CC=C1O3572.8Semi standard non polar33892256
Limocitrin,1TBDMS,isomer #4COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C(OC)=C3O2)=CC=C1O3627.8Semi standard non polar33892256
Limocitrin,2TBDMS,isomer #1COC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3723.8Semi standard non polar33892256
Limocitrin,2TBDMS,isomer #2COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C(OC)=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3791.7Semi standard non polar33892256
Limocitrin,2TBDMS,isomer #3COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(O)C(OC)=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3704.7Semi standard non polar33892256
Limocitrin,2TBDMS,isomer #4COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3O2)=CC=C1O3688.1Semi standard non polar33892256
Limocitrin,2TBDMS,isomer #5COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C(OC)=C3O2)=CC=C1O3777.1Semi standard non polar33892256
Limocitrin,2TBDMS,isomer #6COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3O2)=CC=C1O3789.6Semi standard non polar33892256
Limocitrin,3TBDMS,isomer #1COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3930.6Semi standard non polar33892256
Limocitrin,3TBDMS,isomer #2COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3801.0Semi standard non polar33892256
Limocitrin,3TBDMS,isomer #3COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C(OC)=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3902.4Semi standard non polar33892256
Limocitrin,3TBDMS,isomer #4COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3O2)=CC=C1O3893.3Semi standard non polar33892256
Limocitrin,4TBDMS,isomer #1COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C4010.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Limocitrin GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-0319000000-916e78a0249246554fa62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Limocitrin GC-MS (4 TMS) - 70eV, Positivesplash10-01b9-2312089000-167f74930f837df18f1f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Limocitrin 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 - Limocitrin LC-ESI-QTOF , negative-QTOFsplash10-0002-0009000000-68df39c49592dae618262017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Limocitrin LC-ESI-QTOF , negative-QTOFsplash10-001i-0009000000-92129baf970b23db05392017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Limocitrin LC-ESI-QTOF , negative-QTOFsplash10-03y3-0950000000-b6df732dc8a613daa6f42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Limocitrin LC-ESI-QTOF , positive-QTOFsplash10-0002-0009000000-095643a6e479babccf522017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Limocitrin LC-ESI-QTOF , positive-QTOFsplash10-000t-0009000000-f1352a438263d2a9a8922017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Limocitrin 10V, Negative-QTOFsplash10-0002-0009000000-080474eeeaacd09b4a872021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Limocitrin 20V, Negative-QTOFsplash10-001i-0009000000-84db9ce8c659ba58f2032021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Limocitrin 20V, Positive-QTOFsplash10-000t-0009000000-f1352a438263d2a9a8922021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Limocitrin 10V, Positive-QTOFsplash10-0002-0009000000-095643a6e479babccf522021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Limocitrin 40V, Negative-QTOFsplash10-03y3-0950000000-b6df732dc8a613daa6f42021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Limocitrin 10V, Positive-QTOFsplash10-0002-0009000000-f4088022d7a1ce5904d42015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Limocitrin 20V, Positive-QTOFsplash10-0002-0009000000-072cbfd0f75bab2c82822015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Limocitrin 40V, Positive-QTOFsplash10-0ue9-1952000000-c8c1fc3ae74487ec15672015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Limocitrin 10V, Negative-QTOFsplash10-0002-0009000000-e4f48dc3b9efce5f07902015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Limocitrin 20V, Negative-QTOFsplash10-0002-0029000000-4b7f4346f71d27eecb9b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Limocitrin 40V, Negative-QTOFsplash10-01bc-2982000000-a396d10514a1787c57c52015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Limocitrin 10V, Positive-QTOFsplash10-0002-0009000000-24b80c82c41a998b9ea52021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Limocitrin 20V, Positive-QTOFsplash10-0002-0009000000-b4bb1ffb9bc021542b412021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Limocitrin 40V, Positive-QTOFsplash10-00ls-1903000000-cefe5a930f54d156cf122021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Limocitrin 10V, Negative-QTOFsplash10-0002-0009000000-4173ab4cf400ed4c20372021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Limocitrin 20V, Negative-QTOFsplash10-0002-0439000000-90b8a03523c50fc7a1782021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Limocitrin 40V, Negative-QTOFsplash10-00yi-1921000000-ecebb4a8ac8569f176c32021-09-25Wishart 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 IDFDB000652
KNApSAcK IDC00004731
Chemspider ID4590163
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5489485
PDB IDNot Available
ChEBI ID542813
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1486341
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.. .