IMPPAT Phytochemical information: 
Luteolin
Luteolin
Summary

SMILES: Oc1cc(O)c2c(c1)oc(cc2=O)c1ccc(c(c1)O)O
InChI: 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
InChIKey: IQPNAANSBPBGFQ-UHFFFAOYSA-N
DeepSMILES: OcccO)ccc6)occc6=O)))cccccc6)O))O
Scaffold Graph/Node/Bond level: O=c1cc(-c2ccccc2)oc2ccccc12
Scaffold Graph/Node level: OC1CC(C2CCCCC2)OC2CCCCC12
Scaffold Graph level: CC1CC(C2CCCCC2)CC2CCCCC12
Functional groups: cO; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavones
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavones
Synonymous chemical names:
luteolin, luteoline, 3',4',7,8-tetrahydroxyflavonoid, Luteolin, luteolin glycoside
External chemical identifiers:
CID:CID_5280445; ChEMBL:CHEMBL151; ChEBI:CHEBI:15864; ZINC:ZINC000018185774; FDASRS:KUX1ZNC9J2; SureChEMBL:SCHEMBL20426; MolPort-000-706-683
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Luteolin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 286.24
Log P RDKit 2.28
Topological polar surface area (Å2) RDKit 111.13
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 0
Shape complexity RDKit 0
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Luteolin
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.510622
Luteolin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.25
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No
Luteolin
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_001795ENSG00000147082CCNB385417ChEMBL
TAR_EXP_001737ENSG00000145391SETD780854ChEMBL, NPASS
TAR_EXP_000516ENSG00000151151IPMK253430ChEMBL, NPASS
TAR_EXP_000545ENSG00000108479GALK12584NPASS
TAR_EXP_001735ENSG00000107854TNKS280351ChEMBL, NPASS
TAR_EXP_000500ENSG00000275565ALOX5240BindingDB, ChEMBL, NPASS
TAR_EXP_000503ENSG00000161905ALOX15246BindingDB, ChEMBL, NPASS
TAR_EXP_000519ENSG00000171298GAA2548BindingDB, ChEMBL, NPASS
TAR_EXP_000504ENSG00000179593ALOX15B247ChEMBL, NPASS
TAR_EXP_001728ENSG00000176208ATAD579915NPASS
TAR_EXP_001150ENSG00000070501POLB5423ChEMBL, NPASS
TAR_EXP_001689ENSG00000168748CA7766BindingDB, ChEMBL, NPASS
TAR_EXP_000499ENSG00000108839ALOX12239NPASS
TAR_EXP_000814ENSG00000108424KPNB13837NPASS
TAR_EXP_000773ENSG00000169083AR367ChEMBL, NPASS
TAR_EXP_000752ENSG00000142192APP351BindingDB, ChEMBL, NPASS
TAR_EXP_000747ENSG00000138413IDH13417ChEMBL, NPASS
TAR_EXP_000715ENSG00000044574HSPA53309NPASS
TAR_EXP_000706ENSG00000291796APEX1328ChEMBL, NPASS
TAR_EXP_000701ENSG00000164120HPGD3248ChEMBL, NPASS
TAR_EXP_001683ENSG00000133742CA1759BindingDB, ChEMBL, NPASS
TAR_EXP_000687ENSG00000100644HIF1A3091NPASS
TAR_EXP_000676ENSG00000072506HSD17B103028ChEMBL, NPASS
TAR_EXP_000674ENSG00000123636BAZ2B29994ChEMBL, NPASS
TAR_EXP_000660ENSG00000082701GSK3B2932BindingDB, ChEMBL, NPASS
TAR_EXP_000659ENSG00000105723GSK3A2931ChEMBL
TAR_EXP_000645ENSG00000113580NR3C12908ChEMBL, NPASS
TAR_EXP_000634ENSG00000099875MKNK22872BindingDB, ChEMBL, NPASS
TAR_EXP_000626ENSG00000178623GPR352859BindingDB, ChEMBL, NPASS
TAR_EXP_000619ENSG00000254598CSNK2A3283106BindingDB, ChEMBL, NPASS
TAR_EXP_000611ENSG00000174876AMY1B277BindingDB
TAR_EXP_000609ENSG00000237763AMY1A276ChEMBL
TAR_EXP_000608ENSG00000115419GLS2744NPASS
TAR_EXP_000603ENSG00000124767GLO12739ChEMBL, NPASS
TAR_EXP_000593ENSG00000102393GLA2717NPASS
TAR_EXP_000567ENSG00000177628GBA12629NPASS
TAR_EXP_000554ENSG00000101347SAMHD125939ChEMBL
TAR_EXP_001148ENSG00000172115CYCS54205ChEMBL, NPASS
TAR_EXP_001686ENSG00000167434CA4762BindingDB, ChEMBL, NPASS
TAR_EXP_001691ENSG00000074410CA12771BindingDB, ChEMBL, NPASS
TAR_EXP_000491ENSG00000186318BACE123621BindingDB, ChEMBL
TAR_EXP_000132ENSG00000137491SLCO2B111309ChEMBL
TAR_EXP_000456ENSG00000085662AKR1B1231ChEMBL, NPASS
TAR_EXP_000053ENSG00000079337RAPGEF310411ChEMBL, NPASS
TAR_EXP_000034ENSG00000105810CDK61021BindingDB, NPASS
TAR_EXP_000032ENSG00000164885CDK51020ChEMBL
TAR_EXP_000027ENSG00000123374CDK21017BindingDB, ChEMBL, NPASS
TAR_EXP_000017ENSG00000169371SNUPN10073NPASS
TAR_EXP_000016ENSG00000254986DPP310072BindingDB
TAR_EXP_000015ENSG00000025434NR1H310062ChEMBL
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_001801ENSG00000079277MKNK18569BindingDB, ChEMBL, NPASS
TAR_EXP_001810ENSG00000067955CBFB865NPASS
TAR_EXP_001812ENSG00000173273TNKS8658ChEMBL, NPASS
TAR_EXP_001822ENSG00000120889TNFRSF10B8795ChEMBL
TAR_EXP_001834ENSG00000176749CDK5R18851ChEMBL, NPASS
TAR_EXP_001845ENSG00000134057CCNB1891ChEMBL
TAR_EXP_001872ENSG00000157456CCNB29133ChEMBL, NPASS
TAR_EXP_001885ENSG00000178999AURKB9212BindingDB
TAR_EXP_001906ENSG00000118777ABCG29429BindingDB, ChEMBL, NPASS
TAR_EXP_001912ENSG00000158859ADAMTS49507BindingDB, ChEMBL
TAR_EXP_001913ENSG00000004468CD38952BindingDB, ChEMBL, NPASS
TAR_EXP_001923ENSG00000066135KDM4A9682ChEMBL, NPASS
TAR_EXP_001930ENSG00000170312CDK1983ChEMBL
TAR_EXP_000095ENSG00000224143EHMT210919ChEMBL, NPASS
TAR_EXP_000105ENSG00000154736ADAMTS511096BindingDB, ChEMBL
TAR_EXP_000111ENSG00000164985PSIP111168BindingDB
TAR_EXP_000119ENSG00000101751POLI11201ChEMBL, NPASS
TAR_EXP_000433ENSG00000168496FEN12237ChEMBL, NPASS
TAR_EXP_000428ENSG00000165140FBP12203ChEMBL, NPASS
TAR_EXP_000424ENSG00000169710FASN2194ChEMBL, NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216ChEMBL, NPASS
TAR_EXP_000357ENSG00000277571ELANE1991BindingDB, ChEMBL, NPASS
TAR_EXP_000322ENSG00000197635DPP41803BindingDB, ChEMBL, NPASS
TAR_EXP_000290ENSG00000196730DAPK11612BindingDB, ChEMBL, NPASS
TAR_EXP_000285ENSG00000137869CYP19A11588ChEMBL
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000276ENSG00000272532CYP2D61565NPASS
TAR_EXP_000462ENSG00000122025FLT32322ChEMBL, NPASS
TAR_EXP_000273ENSG00000138109CYP2C91559NPASS
TAR_EXP_000264ENSG00000138061CYP1B11545BindingDB, ChEMBL, NPASS
TAR_EXP_000263ENSG00000140505CYP1A21544BindingDB, ChEMBL, NPASS
TAR_EXP_000262ENSG00000140465CYP1A11543BindingDB, ChEMBL, NPASS
TAR_EXP_000259ENSG00000165168CYBB1536ChEMBL
TAR_EXP_000234ENSG00000230700CSNK2B1460ChEMBL, NPASS
TAR_EXP_000232ENSG00000070770CSNK2A21459ChEMBL, NPASS
TAR_EXP_000231ENSG00000101266CSNK2A11457ChEMBL, NPASS
TAR_EXP_000222ENSG00000112062MAPK141432BindingDB
TAR_EXP_000219ENSG00000143799PARP1142ChEMBL, NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245ChEMBL, NPASS
TAR_EXP_000271ENSG00000165841CYP2C191557NPASS
TAR_EXP_000822ENSG00000182866LCK3932ChEMBL, NPASS
TAR_EXP_001684ENSG00000104267CA2760BindingDB, ChEMBL, NPASS
TAR_EXP_000843ENSG00000284190MIR21406991ChEMBL
TAR_EXP_000885ENSG00000149968MMP34314ChEMBL, NPASS
TAR_EXP_000884ENSG00000087245MMP24313ChEMBL, NPASS
TAR_EXP_000881ENSG00000087085ACHE43BindingDB, ChEMBL, NPASS
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_000860ENSG00000152601MBNL14154NPASS
TAR_EXP_000853ENSG00000276155MAPT4137ChEMBL, NPASS
TAR_EXP_000852ENSG00000069535MAOB4129ChEMBL, NPASS
TAR_EXP_000833ENSG00000160789LMNA4000NPASS
TAR_EXP_001309ENSG00000145388METTL1457721ChEMBL
TAR_EXP_001343ENSG00000114200BCHE590BindingDB, NPASS
TAR_EXP_001344ENSG00000132341RAN5901NPASS
TAR_EXP_000886ENSG00000137673MMP74316BindingDB, ChEMBL
TAR_EXP_001359ENSG00000171791BCL2596ChEMBL, NPASS
TAR_EXP_001362ENSG00000173039RELA5970ChEMBL
TAR_EXP_001364ENSG00000171552BCL2L1598ChEMBL, NPASS
TAR_EXP_001431ENSG00000177189RPS6KA36197BindingDB, ChEMBL
TAR_EXP_001468ENSG00000204842ATXN26311NPASS
TAR_EXP_001485ENSG00000197299BLM641ChEMBL, NPASS
TAR_EXP_001538ENSG00000175003SLC22A16580BindingDB, ChEMBL
TAR_EXP_001540ENSG00000112499SLC22A26582BindingDB, ChEMBL
TAR_EXP_001547ENSG00000275349SMN16606ChEMBL, NPASS
TAR_EXP_001551ENSG00000145335SNCA6622ChEMBL, NPASS
TAR_EXP_001557ENSG00000012048BRCA1672NPASS
TAR_EXP_001584ENSG00000165025SYK6850BindingDB, ChEMBL, NPASS
TAR_EXP_001360ENSG00000004700RECQL5965ChEMBL, NPASS
TAR_EXP_000888ENSG00000100985MMP94318BindingDB, ChEMBL, NPASS
TAR_EXP_000890ENSG00000262406MMP124321BindingDB, ChEMBL, NPASS
TAR_EXP_000891ENSG00000137745MMP134322BindingDB, ChEMBL, NPASS
TAR_EXP_001151ENSG00000170734POLH5429BindingDB, ChEMBL, NPASS
TAR_EXP_001152ENSG00000005421PON15444ChEMBL, NPASS
TAR_EXP_001145ENSG00000175535PNLIP5406ChEMBL
TAR_EXP_001137ENSG00000122194PLG5340ChEMBL, NPASS
TAR_EXP_001125ENSG00000127445PIN15300NPASS
TAR_EXP_001119ENSG00000137193PIM15292ChEMBL, NPASS
TAR_EXP_001106ENSG00000085563ABCB15243ChEMBL, NPASS
TAR_EXP_001080ENSG00000152256PDK15163ChEMBL, NPASS
TAR_EXP_001073ENSG00000077463SIRT651548ChEMBL
TAR_EXP_001062ENSG00000068745IP6K251447ChEMBL, NPASS
TAR_EXP_001180ENSG00000163939PBRM155193ChEMBL, NPASS
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_001248ENSG00000165819METTL356339ChEMBL
TAR_EXP_001273ENSG00000100804PSMB55693BindingDB, ChEMBL, NPASS
TAR_EXP_001280ENSG00000198074AKR1B1057016ChEMBL, NPASS
TAR_EXP_001298ENSG00000095303PTGS15742ChEMBL, NPASS
TAR_EXP_001299ENSG00000073756PTGS25743BindingDB, ChEMBL, NPASS
TAR_EXP_001306ENSG00000196396PTPN15770ChEMBL, NPASS
TAR_EXP_001059ENSG00000122008POLK51426ChEMBL, NPASS
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_001018ENSG00000086991NOX450507BindingDB, ChEMBL, NPASS
TAR_EXP_000969ENSG00000077150NFKB24791ChEMBL
TAR_EXP_000968ENSG00000109320NFKB14790ChEMBL
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_000961ENSG00000115488NEU24759BindingDB, NPASS
TAR_EXP_001602ENSG00000068323TFE37030ChEMBL
TAR_EXP_001609ENSG00000151090THRB7068NPASS
TAR_EXP_001238ENSG00000109339MAPK105602BindingDB
TAR_EXP_001636ENSG00000118271TTR7276ChEMBL, NPASS
TAR_EXP_001678ENSG00000158125XDH7498BindingDB, ChEMBL, NPASS
TAR_EXP_001676ENSG00000165392WRN7486ChEMBL, NPASS
TAR_EXP_001663ENSG00000162607USP17398NPASS
TAR_EXP_001618ENSG00000198900TOP17150ChEMBL, NPASS
TAR_EXP_001619ENSG00000131747TOP2A7153ChEMBL, NPASS
TAR_EXP_001621ENSG00000141510TP537157NPASS
TAR_EXP_001628ENSG00000072315TRPC57224ChEMBL, NPASS
TAR_EXP_001631ENSG00000165409TSHR7253ChEMBL, NPASS
TAR_EXP_001647ENSG00000077498TYR7299BindingDB, ChEMBL, NPASS
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL, NPASS
TAR_EXP_001680ENSG00000176105YES17525BindingDB, ChEMBL, NPASS
TAR_EXP_000845ENSG00000166949SMAD34088NPASS
TAR_EXP_001662ENSG00000131408NR1H27376ChEMBL