Apigenin

Representations & DB's id
ChEBI:	CHEBI:18388
ChEMBL:	CHEMBL28
PubChem:	5280443
IUPAC:	5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Standard InChI:	InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H
Standard InChI Key:	KZNIFHPLKGYRTM-UHFFFAOYSA-N
SMILES:	Oc1ccc(cc1)c1cc(=O)c2c(o1)cc(cc2O)O

Molecular propeties
AlogP:	2.58
Hydrogen bonds acceptors:	5
Hydrogen bonds donors:	3
Rotatable bonds:	1
Number of rings:	3
Molecular Weight:	270.05
Topological polar surface area:	87
Number of aromatic rings:	3
Fsp3:	0
Number of carbons:	15

Plant sources

Part of plant	Plant name	Ref.
Plant	Aconitum napellus
Plant	Cannabis sativa
Plant	Lavandula vera
Plant	Arachis hypogaea
Plant	Ocimum gratissimum
Plant	Vinca minor
Plant	Taraxacum officinale
Plant	Rhaponticum carthamoides
Plant	Rhodiola rosea
Plant	Glycyrrhiza uralensis
Plant	Glycyrrhiza echinata
Shoot	Ononis spinosa
Plant	Thymus vulgaris
Plant	Thymus serpyllum
Plant	Achillea millefolium
Plant	Marrubium vulgare
Leaf	Marrubium vulgare
Shoot	Marrubium vulgare
Flower	Crocus sativus

In vitro data

Activity Type	Activity Value	Target Name	UniProt ID
IC50	1700 nM	Cyclin-dependent kinase 6	Q00534
Others	21 %	Serine/threonine-protein kinase PIM1	P11309
Others	16 %	Serine/threonine-protein kinase PIM1	P11309
IC50	30 ug/ml	Epidermal growth factor receptor erbB1	P00533
Others	12 %	Phosphodiesterase 5A	O76074
IC50	10000 nM	Cytochrome P450 19A1	P11511
Others	94 %	Canalicular multispecific organic anion transporter 1	Q92887
Others	8.7 %	DNA topoisomerase II alpha	P11388
Others	1.6	DNA topoisomerase II alpha	P11388
Others	60 %	DNA topoisomerase II alpha	P11388
Others	10 %	Estradiol 17-beta-dehydrogenase 1	P14061
Others	25.2 %	Estradiol 17-beta-dehydrogenase 2	P37059
IC50	710 nM	Estradiol 17-beta-dehydrogenase 1	P14061
IC50	20000 nM	Estradiol 17-beta-dehydrogenase 2	P37059
IC50	800 nM	Casein kinase II alpha	P68400
IC50	5200 nM	Androgen Receptor	P10275
Ki	37400 nM	Butyrylcholinesterase	P06276
Ki	121600 nM	Acetylcholinesterase	P22303
Others	1.9	Peroxisome proliferator-activated receptor gamma	P37231
Others	5.4	Peroxisome proliferator-activated receptor gamma	P37231
Others	2	Peroxisome proliferator-activated receptor alpha	Q07869
Others	2.3	Peroxisome proliferator-activated receptor alpha	Q07869
IC50	570000 nM	Sialidase 2	Q9Y3R4
IC50	900 nM	Cytochrome P450 19A1	P11511
IC50	795 nM	Cytochrome P450 1A2	P05177
IC50	427 nM	Cytochrome P450 1A1	P04798
IC50	25 nM	Cytochrome P450 1B1	Q16678
Potency	11220.2 nM	Prelamin-A/C	P02545
Potency	50118.7 nM	Thyroid hormone receptor beta-1	P10828
Potency	12589.3 nM	Prelamin-A/C	P02545
Potency	19952.6 nM	Nuclear factor NF-kappa-B p105 subunit	P19838
Potency	31622.8 nM	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Q99714
Potency	11220.2 nM	Lysine-specific demethylase 4D-like	B2RXH2
Potency	31622.8 nM	Hemoglobin beta chain	P68871
Potency	22387.2 nM	Survival motor neuron protein	Q16637
Potency	35481.3 nM	Survival motor neuron protein	Q16637
Potency	14125.4 nM	Survival motor neuron protein	Q16637
Potency	14125.4 nM	Survival motor neuron protein	Q16637
Potency	25118.9 nM	Survival motor neuron protein	Q16637
Potency	3981.1 nM	Thyroid stimulating hormone receptor	P16473
Potency	8912.5 nM	Tyrosyl-DNA phosphodiesterase 1	Q9NUW8
Potency	1778.3 nM	Tyrosyl-DNA phosphodiesterase 1	Q9NUW8
Potency	7079.5 nM	Tyrosyl-DNA phosphodiesterase 1	Q9NUW8
Potency	25118.9 nM	Tyrosyl-DNA phosphodiesterase 1	Q9NUW8
Potency	19952.6 nM	Cytochrome P450 2C19	P33261
Potency	7943.3 nM	Cytochrome P450 2C19	P33261
Potency	39810.7 nM	Thyroid hormone receptor beta-1	P10828
Potency	10000 nM	Microtubule-associated protein tau	P10636
Potency	3162.3 nM	Microtubule-associated protein tau	P10636
Potency	10000 nM	Microtubule-associated protein tau	P10636
Potency	15848.9 nM	Microtubule-associated protein tau	P10636
Potency	8912.5 nM	Microtubule-associated protein tau	P10636
Potency	25118.9 nM	Aldehyde dehydrogenase 1A1	P00352
Potency	1995.3 nM	Hypoxia-inducible factor 1 alpha	Q16665
Potency	12589.3 nM	Hypoxia-inducible factor 1 alpha	Q16665
Potency	12589.3 nM	Aldehyde dehydrogenase 1A1	P00352
Potency	12589.3 nM	Aldehyde dehydrogenase 1A1	P00352
Potency	1778.3 nM	Aldehyde dehydrogenase 1A1	P00352
Potency	6309.6 nM	Aldehyde dehydrogenase 1A1	P00352
Potency	10000 nM	Aldehyde dehydrogenase 1A1	P00352
Potency	60119.8 nM	Peripheral myelin protein 22	Q01453
Potency	3162.3 nM	Pyruvate kinase isozymes M1/M2	P14618
Potency	12589.3 nM	Prelamin-A/C	P02545
Potency	5011.9 nM	Arachidonate 15-lipoxygenase	P16050
Potency	12589.3 nM	Hypoxia-inducible factor 1 alpha	Q16665
Potency	1995.3 nM	Hypoxia-inducible factor 1 alpha	Q16665
Potency	35481.3 nM	Microtubule-associated protein tau	P10636
Potency	19952.6 nM	MAP kinase ERK2	P28482
Potency	3162.3 nM	Pyruvate kinase isozymes M1/M2	P14618
Potency	19952.6 nM	Nuclear factor NF-kappa-B p105 subunit	P19838
Potency	5804.8 nM	Niemann-Pick C1 protein	O15118
Potency	39810.7 nM	DNA-(apurinic or apyrimidinic site) lyase	P27695
Potency	10000 nM	Ubiquitin carboxyl-terminal hydrolase 2	O75604
Potency	28183.8 nM	15-hydroxyprostaglandin dehydrogenase [NAD+]	P15428
Potency	3548.1 nM	15-hydroxyprostaglandin dehydrogenase [NAD+]	P15428
Potency	22387.2 nM	15-hydroxyprostaglandin dehydrogenase [NAD+]	P15428
Potency	31622.8 nM	15-hydroxyprostaglandin dehydrogenase [NAD+]	P15428
Potency	501.2 nM	Thrombopoietin	P40225
Potency	31622.8 nM	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Q99714
Potency	3981.1 nM	Cellular tumor antigen p53	P04637
Potency	5011.9 nM	Cellular tumor antigen p53	P04637
Potency	398.1 nM	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Q99714
Potency	15848.9 nM	Cellular tumor antigen p53	P04637
Potency	25118.9 nM	Neuropeptide S receptor	Q6W5P4
Potency	39810.7 nM	Cytochrome P450 2D6	P10635
Potency	7943.3 nM	Cytochrome P450 3A4	P08684
Potency	1258.9 nM	Cytochrome P450 3A4	P08684
Potency	3162.3 nM	Cytochrome P450 3A4	P08684
Potency	12589.3 nM	Cytochrome P450 2D6	P10635
Potency	5011.9 nM	Cytochrome P450 2C9	P11712
Potency	7943.3 nM	Cytochrome P450 3A4	P08684
Potency	1258.9 nM	Cytochrome P450 3A4	P08684
Potency	12589.3 nM	Geminin	O75496
Potency	31622.8 nM	Cytochrome P450 2C9	P11712
Potency	3162.3 nM	Cytochrome P450 3A4	P08684
Potency	501.2 nM	Thrombopoietin	P40225
Potency	11220.2 nM	Beta-glucocerebrosidase	P04062
Potency	8912.5 nM	Beta-glucocerebrosidase	P04062
Potency	3262.9 nM	ATPase family AAA domain-containing protein 5	Q96QE3
Potency	19952.6 nM	Beta-glucocerebrosidase	P04062
Potency	12589.3 nM	Beta-glucocerebrosidase	P04062
Potency	7079.5 nM	Beta-glucocerebrosidase	P04062
Potency	461.1 nM	Nuclear factor erythroid 2-related factor 2	Q16236
Potency	794.3 nM	M-phase phosphoprotein 8	Q99549
Potency	37933 nM	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Q13526
Potency	2058.8 nM	ATPase family AAA domain-containing protein 5	Q96QE3
Others	88 pm/min/mg	UDP-glucuronosyltransferase 1-1	P22309
Others	164 pm/min/mg	UDP-glucuronosyltransferase 1-10	Q9HAW8
Others	508 pm/min/mg	UDP-glucuronosyltransferase 1-3	P35503
Others	0 pm/min/mg	UDP-glucuronosyltransferase 1A4	P22310
Others	845 pm/min/mg	UDP-glucuronosyltransferase 1-8	Q9HAW9
Others	574 pm/min/mg	UDP-glucuronosyltransferase 1-8	Q9HAW9
Others	18 pm/min/mg	UDP-glucuronosyltransferase 2B15	P54855
IC50	38500 nM	Beta-secretase 1	P56817
Potency	35481.3 nM	Aryl hydrocarbon receptor	P35869
Potency	28183.8 nM	Aryl hydrocarbon receptor	P35869
Potency	35481.3 nM	Cellular tumor antigen p53	P04637
Potency	33491.5 nM	Nuclear factor erythroid 2-related factor 2	Q16236
Potency	24336.5 nM	Nuclear factor erythroid 2-related factor 2	Q16236
Potency	31622.8 nM	Cellular tumor antigen p53	P04637
Potency	35481.3 nM	Glutaminase kidney isoform, mitochondrial	O94925
Potency	11220.2 nM	Ataxin-2	Q99700
Potency	22387.2 nM	Breast cancer type 1 susceptibility protein	P38398
Potency	66824.2 nM	Interleukin-8	P10145
Potency	4216.3 nM	Nuclear receptor ROR-gamma	P51449
EC50	3000 nM	Tyrosine-protein kinase SYK	P43405
IC50	1700 nM	Cyclin-dependent kinase 6	Q00534
IC50	1900 nM	Glycogen synthase kinase-3 beta	P49841
IC50	38500 nM	Beta-secretase 1	P56817
IC50	12 nM	Acetylcholinesterase	P22303
Others	6.3	Peroxisome proliferator-activated receptor delta	Q03181
Others	3.9	Peroxisome proliferator-activated receptor delta	Q03181
IC50	1450 nM	Tyrosine-protein kinase receptor FLT3	P36888
IC50	100000 nM	Poly [ADP-ribose] polymerase-1	P09874
IC50	2951.21 nM	Tankyrase-2	Q9H2K2
IC50	2900 nM	Tankyrase-2	Q9H2K2
IC50	3162.28 nM	Tankyrase-1	O95271
IC50	3100 nM	Tankyrase-1	O95271
Others	50 %	Arachidonate 5-lipoxygenase	P09917
Ki	81000 nM	Cystic fibrosis transmembrane conductance regulator	P13569
EC50	9000 nM	Cystic fibrosis transmembrane conductance regulator	P13569
Ki	520 nM	Xanthine dehydrogenase	P47989
IC50	3200 nM	Xanthine dehydrogenase	P47989
IC50	18000 nM	Transthyretin	P02766
Kd	250 nM	Transthyretin	P02766
IC50	31000 nM	Death-associated protein kinase 1	P53355
IC50	1200 nM	Cytochrome P450 19A1	P11511
Others	84 %	Isocitrate dehydrogenase [NADP] cytoplasmic	O75874
Others	97.4 %	Isocitrate dehydrogenase [NADP] cytoplasmic	O75874
Others	34 %	Aldo-keto reductase family 1 member B10	O60218
Others	25 %	Aldo-keto reductase family 1 member B10	O60218
IC50	37100 nM	Aldo-keto reductase family 1 member B10	O60218
Ki	6000 nM	Aldo-keto reductase family 1 member B10	O60218
IC50	11900 nM	Aldose reductase	P15121
IC50	6600 nM	Aldo-keto reductase family 1 member B10	O60218
Others	10	Aldo-keto reductase family 1 member B10	O60218
Others	21.3 %	Insulin receptor	P06213
Others	19.9 %	Insulin receptor	P06213
Others	80.1 %	Insulin receptor	P06213
Others	10.7 %	Insulin receptor	P06213
Others	75.2 %	Glutaminyl-peptide cyclotransferase	Q16769

Apigenin

Representations & DB's id

Molecular propeties

Plant sources

In vitro data