Luteolin

Representations & DB's id
ChEBI:	CHEBI:15864
ChEMBL:	CHEMBL151
PubChem:	5280445
IUPAC:	2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
Standard 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
Standard InChI Key:	IQPNAANSBPBGFQ-UHFFFAOYSA-N
SMILES:	Oc1cc(O)c2c(c1)oc(cc2=O)c1ccc(c(c1)O)O

Molecular propeties
AlogP:	2.28
Hydrogen bonds acceptors:	6
Hydrogen bonds donors:	4
Rotatable bonds:	1
Number of rings:	3
Molecular Weight:	286.05
Topological polar surface area:	107
Number of aromatic rings:	3
Fsp3:	0
Number of carbons:	15

Plant sources

Part of plant	Plant name	Ref.
Herba	Polygonum aviculare
Cortex	Punica granatum
Cortex	Punica granatum
Cortex	Punica granatum
Cortex	Punica granatum
Cortex	Punica granatum
Cortex	Punica granatum
Cortex	Punica granatum
Cortex	Punica granatum
Plant	Aconitum napellus
Plant	Cannabis sativa
Plant	Arachis hypogaea
Plant	Arachis hypogaea
Radix	Arctium lappa
Plant	Vinca minor
Flower	Taraxacum officinale
Flower	Taraxacum officinale
Fructus	Capsicum annuum
Leaf	Plantago major
Plant	Rhodiola rosea
Plant	Thymus vulgaris
Leaf	Thymus vulgaris
Leaf	Marrubium vulgare
Shoot	Marrubium vulgare
Plant	Marrubium vulgare
Plant	Eucalyptus maideni

In vitro data

Activity Type	Activity Value	Target Name	UniProt ID
IC50	300000 nM	Cyclin-dependent kinase 6	Q00534
Others	14 %	Serine/threonine-protein kinase PIM1	P11309
Others	0 %	Serine/threonine-protein kinase PIM1	P11309
IC50	62500 nM	Fatty acid synthase	P49327
Others	0.28	DNA topoisomerase I	P11387
Others	4.08	DNA topoisomerase II alpha	P11388
IC50	7700 nM	Glyoxalase I	Q04760
IC50	18400 nM	Salivary alpha-amylase	P04745
Others	88.8 %	Salivary alpha-amylase	P04745
Ki	166100 nM	Butyrylcholinesterase	P06276
Ki	65800 nM	Acetylcholinesterase	P22303
IC50	130000 nM	Sialidase 2	Q9Y3R4
IC50	3370 nM	Cytochrome P450 1A2	P05177
IC50	1249 nM	Cytochrome P450 1A1	P04798
IC50	79 nM	Cytochrome P450 1B1	Q16678
Others	1	Lymphocyte differentiation antigen CD38	P28907
Potency	3162.3 nM	Prelamin-A/C	P02545
Potency	7943.3 nM	ATP-dependent DNA helicase Q1	P46063
Potency	47269 nM	Galactokinase	P51570
Potency	6309.6 nM	ATP-dependent DNA helicase Q1	P46063
Potency	8912.5 nM	ATP-dependent DNA helicase Q1	P46063
Potency	12589.3 nM	ATP-dependent DNA helicase Q1	P46063
Potency	10000 nM	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Q99714
Potency	8912.5 nM	Lysine-specific demethylase 4D-like	B2RXH2
Potency	8912.5 nM	Lysine-specific demethylase 4D-like	B2RXH2
Potency	12589.3 nM	Lysine-specific demethylase 4D-like	B2RXH2
Potency	8912.5 nM	Survival motor neuron protein	Q16637
Potency	39810.7 nM	Thyroid stimulating hormone receptor	P16473
Potency	19952.6 nM	Tyrosyl-DNA phosphodiesterase 1	Q9NUW8
Potency	39810.7 nM	Tyrosyl-DNA phosphodiesterase 1	Q9NUW8
Potency	44668.4 nM	Thyroid hormone receptor beta-1	P10828
Potency	15848.9 nM	Cytochrome P450 2C19	P33261
Potency	12589.3 nM	Microtubule-associated protein tau	P10636
Potency	12589.3 nM	Microtubule-associated protein tau	P10636
Potency	398.1 nM	Hypoxia-inducible factor 1 alpha	Q16665
Potency	19952.6 nM	Aldehyde dehydrogenase 1A1	P00352
Potency	8912.5 nM	Aldehyde dehydrogenase 1A1	P00352
Potency	2511.9 nM	Arachidonate 15-lipoxygenase	P16050
Potency	1584.9 nM	Arachidonate 15-lipoxygenase	P16050
Potency	398.1 nM	Hypoxia-inducible factor 1 alpha	Q16665
Potency	15848.9 nM	Arachidonate 12-lipoxygenase	P18054
Potency	2511.9 nM	Arachidonate 12-lipoxygenase	P18054
Potency	11220.2 nM	15-hydroxyprostaglandin dehydrogenase [NAD+]	P15428
Potency	3162.3 nM	Cellular tumor antigen p53	P04637
Potency	10000 nM	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Q99714
Potency	15848.9 nM	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Q99714
Potency	12589.3 nM	Cellular tumor antigen p53	P04637
Potency	5011.9 nM	Cellular tumor antigen p53	P04637
Potency	50118.7 nM	Alpha-galactosidase A	P06280
Potency	19952.6 nM	Bloom syndrome protein	P54132
Potency	15848.9 nM	Bloom syndrome protein	P54132
Potency	25118.9 nM	Lysosomal alpha-glucosidase	P10253
Potency	7079.5 nM	DNA polymerase beta	P06746
Potency	35481.3 nM	Bloom syndrome protein	P54132
Potency	15848.9 nM	Cytochrome P450 3A4	P08684
Potency	31622.8 nM	Cytochrome P450 2D6	P10635
Potency	5011.9 nM	Cytochrome P450 3A4	P08684
Potency	31622.8 nM	Cytochrome P450 2C9	P11712
Potency	15848.9 nM	Cytochrome P450 3A4	P08684
Potency	39810.7 nM	ATP-dependent DNA helicase Q1	P46063
Potency	5011.9 nM	Cytochrome P450 3A4	P08684
Potency	28183.8 nM	Beta-glucocerebrosidase	P04062
Potency	12589.3 nM	Beta-glucocerebrosidase	P04062
Potency	44668.4 nM	Lysine-specific demethylase 4A	O75164
Potency	20596.2 nM	Nuclear factor erythroid 2-related factor 2	Q16236
Potency	28183.8 nM	Cellular tumor antigen p53	P04637
Potency	7304.8 nM	ATPase family AAA domain-containing protein 5	Q96QE3
Potency	10000 nM	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Q96KQ7
Potency	79432.8 nM	Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8
Potency	15848.9 nM	Arachidonate 15-lipoxygenase, type II	O15296
Potency	10000 nM	Arachidonate 15-lipoxygenase, type II	O15296
Potency	9196.2 nM	ATPase family AAA domain-containing protein 5	Q96QE3
IC50	8200 nM	Lymphocyte differentiation antigen CD38	P28907
EC50	7240 nM	G-protein coupled receptor 35	Q9HC97
EC50	3200 nM	G-protein coupled receptor 35	Q9HC97
IC50	18600 nM	G-protein coupled receptor 35	Q9HC97
Others	1.5	G-protein coupled receptor 35	Q9HC97
IC50	3610 nM	Matrix metalloproteinase-2	P08253
IC50	16200 nM	Matrix metalloproteinase 3	P08254
IC50	5620 nM	Matrix metalloproteinase 9	P14780
IC50	980 nM	Matrix metalloproteinase 12	P39900
IC50	10050 nM	Matrix metalloproteinase 13	P45452
Others	30 %	Matrix metalloproteinase-2	P08253
Others	30 %	Matrix metalloproteinase 3	P08254
Others	30 %	Matrix metalloproteinase 9	P14780
Others	30 %	Matrix metalloproteinase 12	P39900
Others	30 %	Matrix metalloproteinase 13	P45452
Potency	3662.6 nM	Geminin	O75496
Potency	35481.3 nM	Glutaminase kidney isoform, mitochondrial	O94925
Potency	18.4 nM	Geminin	O75496
Potency	11220.2 nM	Ataxin-2	Q99700
Potency	19952.6 nM	Ataxin-2	Q99700
Potency	10000 nM	Werner syndrome ATP-dependent helicase	Q14191
Potency	35481.3 nM	Breast cancer type 1 susceptibility protein	P38398
EC50	4500 nM	Tyrosine-protein kinase SYK	P43405
Others	99.89 %	Lysosomal alpha-glucosidase	P10253
IC50	5.96 ug/ml	Lysosomal alpha-glucosidase	P10253
IC50	300000 nM	Cyclin-dependent kinase 6	Q00534
IC50	1500 nM	Glycogen synthase kinase-3 beta	P49841
IC50	830 nM	Tyrosine-protein kinase receptor FLT3	P36888
IC50	4265.8 nM	Poly [ADP-ribose] polymerase-1	P09874
IC50	4200 nM	Poly [ADP-ribose] polymerase-1	P09874
IC50	1071.52 nM	Tankyrase-2	Q9H2K2
IC50	1100 nM	Tankyrase-2	Q9H2K2
IC50	2398.83 nM	Tankyrase-1	O95271
IC50	2400 nM	Tankyrase-1	O95271
IC50	600 nM	Aldose reductase	P15121
IC50	1600 nM	Arachidonate 5-lipoxygenase	P09917
Others	14.4 %	Beta amyloid A4 protein	P05067
IC50	6400 nM	Beta amyloid A4 protein	P05067
Ki	2900 nM	Xanthine dehydrogenase	P47989
Others	28.7 %	Plasminogen	P00747
IC50	7000 nM	Transthyretin	P02766
Kd	70 nM	Transthyretin	P02766
Others	50 %	Xanthine dehydrogenase	P47989
IC50	7800 nM	Xanthine dehydrogenase	P47989
IC50	21000 nM	Death-associated protein kinase 1	P53355
Ki	3691.6 nM	Carbonic anhydrase II	P00918
Ki	10000 nM	Carbonic anhydrase I	P00915
Ki	4.7 nM	Carbonic anhydrase VII	P43166
Ki	60.3 nM	Carbonic anhydrase XII	O43570
Ki	293 nM	Carbonic anhydrase IV	P22748
Others	93.6 %	Isocitrate dehydrogenase [NADP] cytoplasmic	O75874
Others	96.8 %	Isocitrate dehydrogenase [NADP] cytoplasmic	O75874
Others	33 %	Aldo-keto reductase family 1 member B10	O60218
IC50	107800 nM	Aldo-keto reductase family 1 member B10	O60218
IC50	3200 nM	Aldose reductase	P15121
IC50	9200 nM	Aldo-keto reductase family 1 member B10	O60218
Others	10	Aldo-keto reductase family 1 member B10	O60218
Others	46 %	Apoptosis regulator Bcl-2	P10415
Others	49 %	Apoptosis regulator Bcl-X	Q07817

Luteolin

Representations & DB's id

Molecular propeties

Plant sources

In vitro data