Showing metabocard for Luteolin (BMDB0005800)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:18:43 UTC
Update Date2020-05-05 18:38:19 UTC
BMDB IDBMDB0005800
Secondary Accession Numbers
  • BMDB05800
Metabolite Identification
Common NameLuteolin
DescriptionLuteolin, also known as digitoflavone or flacitran, belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Thus, luteolin is considered to be a flavonoid. Based on a literature review a significant number of articles have been published on Luteolin.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-benzopyroneChEBI
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-oneChEBI
3',4',5,7-TetrahydroxyflavoneChEBI
5,7,3',4'-TetrahydroxyflavoneChEBI
DigitoflavoneChEBI
FlacitranChEBI
LuteololChEBI
SalifazideChEBI
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-benzopyrone-4-oneHMDB
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-oneHMDB
LuteolineMeSH, HMDB
3',4',5,7-Tetrahydroxy-flavoneMeSH, HMDB
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-benzopyran-4-onePhytoBank
3’,4’,5,7-TetrahydroxyflavonePhytoBank
5,7,3’,4’-TetrahydroxyflavonePhytoBank
CyanidenonPhytoBank
Chemical FormulaC15H10O6
Average Molecular Weight286.2363
Monoisotopic Molecular Weight286.047738052
IUPAC Name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
Traditional Nameluteolin
CAS Registry Number491-70-3
SMILES
OC1=CC2=C(C(O)=C1)C(=O)C=C(O2)C1=CC=C(O)C(O)=C1
InChI Identifier
InChI=1S/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H
InChI KeyIQPNAANSBPBGFQ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavones
Alternative Parents
Substituents
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point329.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.53PERRISSOUD,D & TESTA,B (1986)
Predicted Properties
PropertyValueSource
logP2.73ALOGPS
logP2.4ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)6.57ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity74.89 m³·mol⁻¹ChemAxon
Polarizability27.73 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0bt9-0000190000-f355e064b0e4a8fee2a8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0bt9-0001290000-3a6e4f4a889b4b595e3eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0bt9-0000190000-f355e064b0e4a8fee2a8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0bt9-0001290000-3a6e4f4a889b4b595e3eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-1735900000-66504e5cc81bcf3dd0a2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aou-0290000000-c72aa0a44afb34434ad5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0zmi-2040190000-5d0acf5ba2153f12546dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-0490000000-b23f87f7af1af38d9686View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-0690000000-74dbeef56be77f266f6eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-001i-0900000000-4b5589ca157de0b5885bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-0079-0090080000-787383a28d957fc65a9eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0090000000-03ffb3e4764e7236f82dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0a4i-0190000000-7f42ffe76ed9c3f69f11View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0090000000-03ffb3e4764e7236f82dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0a4i-0190000000-7f42ffe76ed9c3f69f11View in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-000i-0790000000-814cdaf9d50189cf2f2aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0490000000-b23f87f7af1af38d9686View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0690000000-4135ff68dafc65e9f339View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-4b5589ca157de0b5885bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0090000000-568d5c1e3df3c5693fb4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0190000000-b20ef421e6accd0523a4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-2ca1121832520dd96a2cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0490000000-14b50e413340dc95fac3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0490000000-371552bb5776fd662dd9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0590000000-a412d0980f838bf49619View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0090000000-075f1c69f8e77ea5dbe9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4i-0190000000-7f42ffe76ed9c3f69f11View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-236ab0853a3df459fc37View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001i-0900000000-fda1f09c1506187911ffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-0190000000-956ceb8d223bd9454f93View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001i-1900000000-ba91f3571fdd8398c5e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-001i-0900000000-051f4eceea0c40ddb177View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0005800
DrugBank IDNot Available
Phenol Explorer Compound ID229
FooDB IDFDB013255
KNApSAcK IDC00000674
Chemspider ID4444102
KEGG Compound IDC01514
BioCyc ID5734-TETRAHYDROXYFLAVONE
BiGG IDNot Available
Wikipedia LinkLuteolin
METLIN IDNot Available
PubChem Compound5280445
PDB IDLU2
ChEBI ID15864
References
Synthesis ReferenceHutchins, W. A.; Wheeler, T. S. Chalcones: A new synthesis of chrysin, apigenin and luteolin. Journal of the Chemical Society (1939), 91-4.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available