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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-01-22 22:39:32 UTC
Update Date2021-10-13 04:47:28 UTC
HMDB IDHMDB0005800
Secondary Accession Numbers
  • HMDB05800
Metabolite Identification
Common NameLuteolin
DescriptionLuteolin is a naturally occurring flavonoid. (PMID:17168665 ). The flavonoids are polyphenolic compounds found as integral components of the human diet. They are universally present as constituents of flowering plants, particularly of food plants. The flavonoids are phenyl substituted chromones (benzopyran derivatives) consisting of a 15-carbon basic skeleton (C6-C3-C6), composed of a chroman (C6-C3) nucleus (the benzo ring A and the heterocyclic ring C), also shared by the tocopherols, with a phenyl (the aromatic ring B) substitution usually at the 2-position. Different substitutions can typically occur in the rings, A and B. Several plants and spices containing flavonoid derivatives have found application as disease preventive and therapeutic agents in traditional medicine in Asia for thousands of years. The selection of a particular food plant, plant tissue or herb for its potential health benefits appears to mirror its flavonoid composition. The much lower risk of colon, prostate and breast cancers in Asians, who consume more vegetables, fruits and tea than populations in the Western hemisphere do, raises the question of whether flavonoid components mediate the protective effects of diets rich in these foodstuffs by acting as natural chemopreventive and anticancer agents. An impressive body of information exists on the antitumoral action of plant flavonoids. In vitro work has concentrated on the direct and indirect actions of flavonoids on tumor cells, and has found a variety of anticancer effects such as cell growth and kinase activity inhibition, apoptosis induction, suppression of the secretion of matrix metalloproteinases and of tumor invasive behavior. Furthermore, some studies have reported the impairment of in vivo angiogenesis by dietary flavonoids. Experimental animal studies indicate that certain dietary flavonoids possess antitumoral activity. The hydroxylation pattern of the B ring of the flavones and flavonols, such as luteolin seems to critically influence their activities, especially the inhibition of protein kinase activity and antiproliferation. The different mechanisms underlying the potential anticancer action of plant flavonoids await further elucidation. Certain dietary flavonols and flavones targeting cell surface signal transduction enzymes, such as protein tyrosine and focal adhesion kinases, and the processes of angiogenesis appear to be promising candidates as anticancer agents. Further in vivo studies of these bioactive constituents is deemed necessary in order to develop flavonoid-based anticancer strategies. In view of the increasing interest in the association between dietary flavonoids and cancer initiation and progression, this important field is likely to witness expanded effort and to attract and stimulate further vigorous investigations (PMID:16097445 ).
Structure
Data?1582752365
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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point329.5 °CNot Available
Boiling Point616.00 to 617.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility387.5 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.53PERRISSOUD,D & TESTA,B (1986)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP10(2.73) g/LALOGPS
logP10(2.4) g/LChemAxon
logS10(-3.3) g/LALOGPS
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+166.58730932474
DeepCCS[M-H]-164.22930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LuteolinOC1=CC2=C(C(O)=C1)C(=O)C=C(O2)C1=CC=C(O)C(O)=C15101.5Standard polar33892256
LuteolinOC1=CC2=C(C(O)=C1)C(=O)C=C(O2)C1=CC=C(O)C(O)=C13118.6Standard non polar33892256
LuteolinOC1=CC2=C(C(O)=C1)C(=O)C=C(O2)C1=CC=C(O)C(O)=C13285.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Luteolin,1TMS,isomer #1C[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C(O)=C3)OC2=C13321.5Semi standard non polar33892256
Luteolin,1TMS,isomer #2C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C=C(C1=CC=C(O)C(O)=C1)O23267.0Semi standard non polar33892256
Luteolin,1TMS,isomer #3C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1O3339.1Semi standard non polar33892256
Luteolin,1TMS,isomer #4C[Si](C)(C)OC1=CC(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)=CC=C1O3316.9Semi standard non polar33892256
Luteolin,2TMS,isomer #1C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C(O)=C3)OC2=C13228.0Semi standard non polar33892256
Luteolin,2TMS,isomer #2C[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C)C(O)=C3)OC2=C13318.8Semi standard non polar33892256
Luteolin,2TMS,isomer #3C[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C(O[Si](C)(C)C)=C3)OC2=C13286.4Semi standard non polar33892256
Luteolin,2TMS,isomer #4C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)C=C1O3223.0Semi standard non polar33892256
Luteolin,2TMS,isomer #5C[Si](C)(C)OC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)=CC=C1O3190.1Semi standard non polar33892256
Luteolin,2TMS,isomer #6C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1O[Si](C)(C)C3181.9Semi standard non polar33892256
Luteolin,3TMS,isomer #1C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C)C(O)=C3)OC2=C13235.5Semi standard non polar33892256
Luteolin,3TMS,isomer #2C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C(O[Si](C)(C)C)=C3)OC2=C13200.6Semi standard non polar33892256
Luteolin,3TMS,isomer #3C[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)OC2=C13097.9Semi standard non polar33892256
Luteolin,3TMS,isomer #4C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)C=C1O[Si](C)(C)C3045.5Semi standard non polar33892256
Luteolin,4TMS,isomer #1C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)OC2=C13159.3Semi standard non polar33892256
Luteolin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C(O)=C3)OC2=C13594.4Semi standard non polar33892256
Luteolin,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C=C(C1=CC=C(O)C(O)=C1)O23534.3Semi standard non polar33892256
Luteolin,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1O3594.6Semi standard non polar33892256
Luteolin,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)=CC=C1O3572.9Semi standard non polar33892256
Luteolin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C(O)=C3)OC2=C13797.4Semi standard non polar33892256
Luteolin,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)OC2=C13860.3Semi standard non polar33892256
Luteolin,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C13834.2Semi standard non polar33892256
Luteolin,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)C=C1O3797.1Semi standard non polar33892256
Luteolin,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)=CC=C1O3745.5Semi standard non polar33892256
Luteolin,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1O[Si](C)(C)C(C)(C)C3780.0Semi standard non polar33892256
Luteolin,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)OC2=C14000.9Semi standard non polar33892256
Luteolin,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C13972.2Semi standard non polar33892256
Luteolin,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C13940.9Semi standard non polar33892256
Luteolin,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)C=C1O[Si](C)(C)C(C)(C)C3863.4Semi standard non polar33892256
Luteolin,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C14067.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Luteolin GC-MS (4 TMS)splash10-0bt9-0000190000-f355e064b0e4a8fee2a82014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Luteolin GC-MS (Non-derivatized)splash10-0bt9-0001290000-3a6e4f4a889b4b595e3e2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Luteolin GC-MS (Non-derivatized)splash10-0bt9-0000190000-f355e064b0e4a8fee2a82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Luteolin GC-MS (Non-derivatized)splash10-0bt9-0001290000-3a6e4f4a889b4b595e3e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Luteolin GC-EI-TOF (Non-derivatized)splash10-00dj-1735900000-66504e5cc81bcf3dd0a22017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Luteolin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aou-0290000000-c72aa0a44afb34434ad52017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Luteolin GC-MS (4 TMS) - 70eV, Positivesplash10-0zmi-2040190000-5d0acf5ba2153f12546d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Luteolin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Luteolin 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 - Luteolin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive-QTOFsplash10-000i-0090000000-c8d8c5048f03b4f9ad5e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Luteolin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-000i-0490000000-b23f87f7af1af38d96862012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Luteolin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-0f79-1940000000-006d75dee56e7481a44f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Luteolin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-000i-0290000000-e0e08b588cde4ec7d7c82012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Luteolin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-000i-0190000000-f142e0417f0f94a4623b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Luteolin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive-QTOFsplash10-0f79-1920000000-42c47240052ab59116f72012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Luteolin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-000i-0690000000-74dbeef56be77f266f6e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Luteolin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative-QTOFsplash10-001i-0900000000-4b5589ca157de0b5885b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Luteolin LC-ESI-ITTOF (LCMS-IT-TOF) , Positive-QTOFsplash10-000i-0090000000-7b507d1551bc27fa69522012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Luteolin LC-ESI-ITTOF (LCMS-IT-TOF) , Negative-QTOFsplash10-0079-0090080000-787383a28d957fc65a9e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Luteolin ESI-TOF , Negative-QTOFsplash10-000i-0090000000-03ffb3e4764e7236f82d2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Luteolin ESI-TOF 30V, Negative-QTOFsplash10-0a4i-0190000000-7f42ffe76ed9c3f69f112017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Luteolin ESI-TOF , Negative-QTOFsplash10-000i-0090000000-03ffb3e4764e7236f82d2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Luteolin ESI-TOF 30V, Negative-QTOFsplash10-0a4i-0190000000-7f42ffe76ed9c3f69f112017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Luteolin DI-ESI-qTof , Negative-QTOFsplash10-000i-0790000000-814cdaf9d50189cf2f2a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Luteolin DI-ESI-qTof , Positive-QTOFsplash10-0udr-0930000000-ad4b17e37626938411712017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Luteolin LC-ESI-QTOF , negative-QTOFsplash10-000i-0490000000-b23f87f7af1af38d96862017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Luteolin LC-ESI-QTOF , negative-QTOFsplash10-000i-0690000000-4135ff68dafc65e9f3392017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Luteolin LC-ESI-QTOF , negative-QTOFsplash10-001i-0900000000-4b5589ca157de0b5885b2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Luteolin 10V, Positive-QTOFsplash10-000i-0090000000-1682faadbefced000a712015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Luteolin 20V, Positive-QTOFsplash10-000i-0090000000-fd32d917fb0b393a99aa2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Luteolin 40V, Positive-QTOFsplash10-1000-5690000000-407bf2d6b008427648fa2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Luteolin 10V, Negative-QTOFsplash10-000i-0090000000-c5cbc6ffe79c8cd576042015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Luteolin 20V, Negative-QTOFsplash10-000i-0090000000-147d7dcca6436066ce442015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Luteolin 40V, Negative-QTOFsplash10-0uxu-4960000000-ee3c93ba84300846c3332015-05-27Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0999 +/- 0.0977 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.101 +/- 0.0985 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0-0.288 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1504531
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)Download (PDF)
General References
  1. 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. [PubMed:17168665 ]
  2. 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. [PubMed:16097445 ]

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
Luteolin → Chrysoerioldetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Luteolin → 6-{[2-(3,4-dihydroxyphenyl)-7-hydroxy-4-oxo-4H-chromen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Luteolin → 6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Luteolin → 6-[5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Luteolin → 6-[4-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Luteolin → [5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]oxidanesulfonic aciddetails