Showing Compound Card for Luteolin (CDB000371)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (3) Show 29 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:33:29 UTC
Updated at2020-11-18 16:35:07 UTC
CannabisDB IDCDB000371
Secondary Accession NumbersNot Available
Cannabis Compound 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 lipid molecule. Luteolin is a naturally occurring flavonoid. The selection of a particular food plant, plant tissue or herb for its potential health benefits appears to mirror its flavonoid composition. Luteolin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Luteolin is one of the Flavonoids that have been found in the cannabis plant. (PMID: 6991645 )
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 Weight286.24
Monoisotopic Molecular Weight286.0477
IUPAC Name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
Traditional Nameluteolin
CAS Registry Number491-70-3
SMILES
OC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC(O)=C(O)C=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

Route of exposure:

Source:

Biological location:

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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSLuteolin, 4 TMS, GC-MS Spectrumsplash10-0bt9-0000190000-f355e064b0e4a8fee2a8Spectrum
GC-MSLuteolin, non-derivatized, GC-MS Spectrumsplash10-0bt9-0001290000-3a6e4f4a889b4b595e3eSpectrum
GC-MSLuteolin, non-derivatized, GC-MS Spectrumsplash10-0bt9-0000190000-f355e064b0e4a8fee2a8Spectrum
GC-MSLuteolin, non-derivatized, GC-MS Spectrumsplash10-0bt9-0001290000-3a6e4f4a889b4b595e3eSpectrum
GC-MSLuteolin, non-derivatized, GC-MS Spectrumsplash10-00dj-1735900000-66504e5cc81bcf3dd0a2Spectrum
Predicted GC-MSLuteolin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0aou-0290000000-c72aa0a44afb34434ad5Spectrum
Predicted GC-MSLuteolin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0zmi-2040190000-5d0acf5ba2153f12546dSpectrum
Predicted GC-MSLuteolin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSLuteolin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-0490000000-b23f87f7af1af38d96862012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-0690000000-74dbeef56be77f266f6e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-001i-0900000000-4b5589ca157de0b5885b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-0079-0090080000-787383a28d957fc65a9e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0090000000-03ffb3e4764e7236f82d2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0a4i-0190000000-7f42ffe76ed9c3f69f112017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0090000000-03ffb3e4764e7236f82d2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0a4i-0190000000-7f42ffe76ed9c3f69f112017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-000i-0790000000-814cdaf9d50189cf2f2a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0490000000-b23f87f7af1af38d96862017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0690000000-4135ff68dafc65e9f3392017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-4b5589ca157de0b5885b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0090000000-568d5c1e3df3c5693fb42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0190000000-b20ef421e6accd0523a42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-2ca1121832520dd96a2c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0490000000-14b50e413340dc95fac32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0490000000-371552bb5776fd662dd92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0590000000-a412d0980f838bf496192017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0090000000-075f1c69f8e77ea5dbe92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4i-0190000000-7f42ffe76ed9c3f69f112017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-236ab0853a3df459fc372021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001i-0900000000-fda1f09c1506187911ff2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-0190000000-956ceb8d223bd9454f932021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001i-1900000000-ba91f3571fdd8398c5e92021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-001i-0900000000-051f4eceea0c40ddb1772021-09-20View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Catechol O-methyltransferaseCOMT22q11.21P21964 details
UDP-glucuronosyltransferase 1-1UGT1A12q37P22309 details
Sulfotransferase 1A3SULT1A3P0DMM9 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Catechol O-methyltransferaseCOMT22q11.21P21964 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 2 member 10TAS2R1012p13Q9NYW0 details
Taste receptor type 2 member 16TAS2R167q31.1-q31.3|7q31Q9NYV7 details
Taste receptor type 2 member 40TAS2R407q34P59535 details
Taste receptor type 2 member 3TAS2R37q31.3-q32Q9NYW6 details
Taste receptor type 2 member 4TAS2R47q31.3-q32Q9NYW5 details
Taste receptor type 2 member 7TAS2R712p13Q9NYW3 details
Taste receptor type 2 member 9TAS2R912p13Q9NYW1 details
Taste receptor type 2 member 50TAS2R5012p13.2P59544 details
Taste receptor type 2 member 38TAS2R387q34P59533 details
Taste receptor type 2 member 31TAS2R3112p13.2P59538 details
Taste receptor type 2 member 1TAS2R15p15.31Q9NYW7 details
Taste receptor type 2 member 20TAS2R2012p13.2P59543 details
Taste receptor type 2 member 39TAS2R397q34P59534 details
Taste receptor type 2 member 19TAS2R1912p13.2P59542 details
Taste receptor type 2 member 45TAS2R45P59539 details
Taste receptor type 2 member 30TAS2R3012p13.2P59541 details
Taste receptor type 2 member 42TAS2R42Q7RTR8 details
Taste receptor type 2 member 41TAS2R417q35P59536 details
Taste receptor type 2 member 43TAS2R4312p13.2P59537 details
Taste receptor type 2 member 5TAS2R57q34Q9NYW4 details
Taste receptor type 2 member 46TAS2R4612p13.2P59540 details
Taste receptor type 2 member 13TAS2R1312p13.2Q9NYV9 details
Taste receptor type 2 member 60TAS2R607q35P59551 details
Taste receptor type 2 member 8TAS2R812p13.2Q9NYW2 details
Taste receptor type 2 member 14TAS2R1412p13.2Q9NYV8 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0005800
DrugBank IDNot Available
Phenol Explorer Compound ID229
FoodDB 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
General ReferencesNot Available

Only showing the first 10 proteins. There are 29 proteins in total.

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Enzymes

Enzyme Details
1. Catechol O-methyltransferase
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
Enzyme Details
2. UDP-glucuronosyltransferase 1-1
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
Enzyme Details
3. Sulfotransferase 1A3
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

Only showing the first 10 proteins. There are 29 proteins in total.

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