Luteolin (CHEM028737)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:39:40 UTC
Update Date2016-11-09 01:18:45 UTC
Accession NumberCHEM028737
Identification
Common NameLuteolin
ClassSmall Molecule
DescriptionA tetrahydroxyflavone in which the four hydroxy groups are located at positions 3', 4', 5 and 7. It is thought to play an important role in the human body as an antioxidant, a free radical scavenger, an anti-inflammatory agent and an immune system modulator as well as being active against several cancers.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical 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 Mass286.236 g/mol
Monoisotopic Mass286.048 g/mol
CAS Registry Number491-70-3
IUPAC Name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
Traditional Nameluteolin
SMILESOC1=CC2=C(C(O)=C1)C(=O)C=C(O2)C1=CC=C(O)C(O)=C1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0bt9-0000190000-f355e064b0e4a8fee2a8Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0bt9-0001290000-3a6e4f4a889b4b595e3eSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0bt9-0000190000-f355e064b0e4a8fee2a8Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0bt9-0001290000-3a6e4f4a889b4b595e3eSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-1735900000-66504e5cc81bcf3dd0a2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aou-0290000000-c72aa0a44afb34434ad5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0zmi-2040190000-5d0acf5ba2153f12546dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-0490000000-b23f87f7af1af38d9686Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-0690000000-74dbeef56be77f266f6eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-001i-0900000000-4b5589ca157de0b5885bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-0079-0090080000-787383a28d957fc65a9eSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0090000000-03ffb3e4764e7236f82dSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0a4i-0190000000-7f42ffe76ed9c3f69f11Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0090000000-03ffb3e4764e7236f82dSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0a4i-0190000000-7f42ffe76ed9c3f69f11Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-000i-0790000000-814cdaf9d50189cf2f2aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0490000000-b23f87f7af1af38d9686Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0690000000-4135ff68dafc65e9f339Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-4b5589ca157de0b5885bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0090000000-568d5c1e3df3c5693fb4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0190000000-b20ef421e6accd0523a4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-2ca1121832520dd96a2cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0490000000-14b50e413340dc95fac3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0490000000-371552bb5776fd662dd9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0590000000-a412d0980f838bf49619Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0090000000-075f1c69f8e77ea5dbe9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4i-0190000000-7f42ffe76ed9c3f69f11Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-236ab0853a3df459fc37Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001i-0900000000-fda1f09c1506187911ffSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-0190000000-956ceb8d223bd9454f93Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001i-1900000000-ba91f3571fdd8398c5e9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-001i-0900000000-051f4eceea0c40ddb177Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0005800
FooDB IDFDB013255
Phenol Explorer ID229
KNApSAcK IDC00000674
BiGG IDNot Available
BioCyc ID5734-TETRAHYDROXYFLAVONE
METLIN IDNot Available
PDB IDLU2
Wikipedia LinkLuteolin
Chemspider ID4444102
ChEBI ID15864
PubChem Compound ID5280445
Kegg Compound IDC01514
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11478688
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11897650
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6. https://www.ncbi.nlm.nih.gov/pubmed/?term=18991571
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=19263826
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=19509250
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10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21899269
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22391103
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22749133
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22794353
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22842046
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23035972
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23229294
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=23574272
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=26020516
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=26322379
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=27595800
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=27764981
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=27853236
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=27878246
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=27879665
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=27886116
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=27919958
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=27927066
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=27959422
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=28004344
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=28029146
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=28031430
32. https://www.ncbi.nlm.nih.gov/pubmed/?term=28035396
33. https://www.ncbi.nlm.nih.gov/pubmed/?term=28067377
34. https://www.ncbi.nlm.nih.gov/pubmed/?term=28069121
35. https://www.ncbi.nlm.nih.gov/pubmed/?term=28071803
36. https://www.ncbi.nlm.nih.gov/pubmed/?term=28090531
37. https://www.ncbi.nlm.nih.gov/pubmed/?term=28096694
38. https://www.ncbi.nlm.nih.gov/pubmed/?term=28101184
39. https://www.ncbi.nlm.nih.gov/pubmed/?term=28101223
40. https://www.ncbi.nlm.nih.gov/pubmed/?term=28110189
41. https://www.ncbi.nlm.nih.gov/pubmed/?term=28111945
42. https://www.ncbi.nlm.nih.gov/pubmed/?term=28112209
43. https://www.ncbi.nlm.nih.gov/pubmed/?term=28113103
44. https://www.ncbi.nlm.nih.gov/pubmed/?term=28166217
45. https://www.ncbi.nlm.nih.gov/pubmed/?term=29423013
46. https://www.ncbi.nlm.nih.gov/pubmed/?term=30624931
47. https://www.ncbi.nlm.nih.gov/pubmed/?term=32883638
48. Hutchins, W. A.; Wheeler, T. S. Chalcones: A new synthesis of chrysin, apigenin and luteolin. Journal of the Chemical Society (1939), 91-4.
49. Hutchins, W. A.; Wheeler, T. S. Chalcones: A new synthesis of chrysin, apigenin and luteolin. Journal of the Chemical Society (1939), 91-4.
50. Lupu R, Menendez JA: Pharmacological inhibitors of Fatty Acid Synthase (FASN)--catalyzed endogenous fatty acid biogenesis: a new family of anti-cancer agents? Curr Pharm Biotechnol. 2006 Dec;7(6):483-93.
51. Kandaswami C, Lee LT, Lee PP, Hwang JJ, Ke FC, Huang YT, Lee MT: The antitumor activities of flavonoids. In Vivo. 2005 Sep-Oct;19(5):895-909.