Apigenin

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	98d03858-bcbb-4e2b-acb5-02840c9009ca
Taxonomy	Phenylpropanoids and polyketides > Flavonoids > Flavones
IUPAC Name	5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
SMILES (Canonical)	C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O
SMILES (Isomeric)	C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O
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
InChI Key	KZNIFHPLKGYRTM-UHFFFAOYSA-N
Popularity	11,578 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₅H₁₀O₅
Molecular Weight	270.24 g/mol
Exact Mass	270.05282342 g/mol
Topological Polar Surface Area (TPSA)	87.00 Å²
XlogP	1.70
Atomic LogP (AlogP)	2.58
H-Bond Acceptor	5
H-Bond Donor	3
Rotatable Bonds	1

Synonyms

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520-36-5

5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Versulin

Apigenol

4',5,7-Trihydroxyflavone

Chamomile

Spigenin

Apigenine

C.I. Natural Yellow 1

Pelargidenon 1449

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9671	96.71%
Caco-2	+	0.9313	93.13%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6655	66.55%
OATP2B1 inhibitior	-	0.6489	64.89%
OATP1B1 inhibitior	+	0.9360	93.60%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	+	0.6600	66.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.6857	68.57%
P-glycoprotein inhibitior	-	0.8292	82.92%
P-glycoprotein substrate	-	0.9362	93.62%
CYP3A4 substrate	-	0.5417	54.17%
CYP2C9 substrate	-	0.6443	64.43%
CYP2D6 substrate	-	0.8503	85.03%
CYP3A4 inhibition	+	0.9580	95.80%
CYP2C9 inhibition	+	0.7746	77.46%
CYP2C19 inhibition	+	0.7043	70.43%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.9222	92.22%
CYP2C8 inhibition	+	0.7799	77.99%
CYP inhibitory promiscuity	+	0.7316	73.16%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6044	60.44%
Eye corrosion	-	0.9858	98.58%
Eye irritation	+	0.9629	96.29%
Skin irritation	+	0.5532	55.32%
Skin corrosion	-	0.9784	97.84%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8978	89.78%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.9060	90.60%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.6638	66.38%
Acute Oral Toxicity (c)	III	0.7012	70.12%
Estrogen receptor binding	+	0.9295	92.95%
Androgen receptor binding	+	0.9419	94.19%
Thyroid receptor binding	+	0.6360	63.60%
Glucocorticoid receptor binding	+	0.9518	95.18%
Aromatase binding	+	0.9277	92.77%
PPAR gamma	+	0.9395	93.95%
Honey bee toxicity	-	0.8485	84.85%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.8272	82.72%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	28183.8 nM 22387.2 nM 31622.8 nM	Potency Potency Potency	via CMAUP via CMAUP via CMAUP
CHEMBL220	P22303	Acetylcholinesterase	12 nM	IC50	DOI: 10.1007/s00044-012-0353-y
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	12589.3 nM 12589.3 nM 6309.6 nM 10000 nM	Potency Potency Potency Potency	via CMAUP via CMAUP via CMAUP via CMAUP
CHEMBL5983	O60218	Aldo-keto reductase family 1 member B10	37100 nM 6600 nM	IC50 IC50	PMID: 26529431 PMID: 26529431
CHEMBL1900	P15121	Aldose reductase	11900 nM	IC50	PMID: 26529431
CHEMBL1871	P10275	Androgen Receptor	5200 nM	IC50	PMID: 19592245
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	5011.9 nM	Potency	via CMAUP
CHEMBL5393	Q9UNQ0	ATP-binding cassette sub-family G member 2	3100 nM 5900 nM	IC50 IC50	PMID: 21354800 PMID: 21354800
CHEMBL4822	P56817	Beta-secretase 1	38500 nM 38500 nM	IC50 IC50	PMID: 22243648 DOI: 10.1007/s00044-012-0353-y
CHEMBL1914	P06276	Butyrylcholinesterase	37400 nM	Ki	PMID: 19879672
CHEMBL3629	P68400	Casein kinase II alpha	800 nM 740 nM	IC50 Ki	PMID: 19414254 via Super-PRED
CHEMBL4096	P04637	Cellular tumor antigen p53	3981.1 nM 5011.9 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL2508	Q00534	Cyclin-dependent kinase 6	1700 nM 1700 nM	IC50 IC50	PMID: 15689157 DOI: 10.1007/s00044-009-9233-5
CHEMBL230	P35354	Cyclooxygenase-2	8000 nM	IC50	PMID: 16038536
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	9000 nM	EC50	PMID: 25019478
CHEMBL1978	P11511	Cytochrome P450 19A1	1000 nM 900 nM 1200 nM 900 nM	IC50 IC50 IC50 IC50	PMID: 18778944 PMID: 20413308 PMID: 26301554 via Super-PRED
CHEMBL2231	P04798	Cytochrome P450 1A1	427 nM	IC50	PMID: 20696580
CHEMBL3356	P05177	Cytochrome P450 1A2	795 nM	IC50	PMID: 20696580
CHEMBL4878	Q16678	Cytochrome P450 1B1	25 nM 25 nM	IC50 IC50	PMID: 20696580 via Super-PRED
CHEMBL3622	P33261	Cytochrome P450 2C19	19952.6 nM 7943.3 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	5011.9 nM 31622.8 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	39810.7 nM 12589.3 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	7943.3 nM 1258.9 nM 3162.3 nM 7943.3 nM 1258.9 nM 3162.3 nM	Potency Potency Potency Potency Potency Potency	via CMAUP via CMAUP via CMAUP via CMAUP via CMAUP via CMAUP
CHEMBL2558	P53355	Death-associated protein kinase 1	31000 nM	IC50	PMID: 26322379
CHEMBL284	P27487	Dipeptidyl peptidase IV	140 nM	IC50	via Super-PRED
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	39810.7 nM	Potency	via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	31622.8 nM 31622.8 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL3181	P14061	Estradiol 17-beta-dehydrogenase 1	710 nM 710 nM	IC50 IC50	PMID: 18533708 via Super-PRED
CHEMBL206	P03372	Estrogen receptor alpha	1253 nM	IC50	PMID: 12824043
CHEMBL242	Q92731	Estrogen receptor beta	130 nM	IC50	PMID: 12824043
CHEMBL1293278	O75496	Geminin	12589.3 nM	Potency	via CMAUP
CHEMBL262	P49841	Glycogen synthase kinase-3 beta	1900 nM	IC50	DOI: 10.1007/s00044-012-0353-y
CHEMBL4331	P68871	Hemoglobin beta chain	31622.8 nM	Potency	via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	1995.3 nM 12589.3 nM 12589.3 nM 1995.3 nM	Potency Potency Potency Potency	via CMAUP via CMAUP via CMAUP via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	11220.2 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	19952.6 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	19952.6 nM 8912.5 nM 10000 nM 3162.3 nM 10000 nM 15848.9 nM 8912.5 nM	Potency Potency Potency Potency Potency Potency Potency	via CMAUP via CMAUP via CMAUP via CMAUP via CMAUP via CMAUP via CMAUP
CHEMBL1951	P21397	Monoamine oxidase A	1700 nM 640 nM	IC50 IC50	PMID: 20045650 via Super-PRED
CHEMBL2039	P27338	Monoamine oxidase B	12800 nM	IC50	PMID: 20045650
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	4900 nM 2400 nM	Ki Ki	PMID: 11306701 PMID: 19725578
CHEMBL1250375	Q9NPH5	NADPH oxidase 4	1130 nM	IC50	PMID: 20731357
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	25118.9 nM	Potency	via CMAUP
CHEMBL1293277	O15118	Niemann-Pick C1 protein	5804.8 nM	Potency	via CMAUP
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	19952.6 nM 19952.6 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	12589.3 nM 12589.3 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL1075189	P14618	Pyruvate kinase isozymes M1/M2	3162.3 nM 3162.3 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	22387.2 nM 35481.3 nM 14125.4 nM 14125.4 nM 25118.9 nM	Potency Potency Potency Potency Potency	via CMAUP via CMAUP via CMAUP via CMAUP via CMAUP
CHEMBL6164	O95271	Tankyrase-1	3162.28 nM 3100 nM	IC50 IC50	PMID: 23574272 PMID: 23574272
CHEMBL6154	Q9H2K2	Tankyrase-2	2951.21 nM 2900 nM	IC50 IC50	PMID: 23574272 PMID: 23574272
CHEMBL1293256	P40225	Thrombopoietin	501.2 nM 501.2 nM 501.2 nM	Potency Potency Potency	via CMAUP via CMAUP via Super-PRED
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	50118.7 nM 39810.7 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	3981.1 nM	Potency	via CMAUP
CHEMBL3194	P02766	Transthyretin	18000 nM 653 nM 250 nM	IC50 IC50 Kd	PMID: 26214366 via CMAUP via Super-PRED
CHEMBL1974	P36888	Tyrosine-protein kinase receptor FLT3	1450 nM	IC50	PMID: 23411073
CHEMBL2599	P43405	Tyrosine-protein kinase SYK	4200 nM	IC50	PMID: 22257213
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	8912.5 nM 1778.3 nM 7079.5 nM	Potency Potency Potency	via CMAUP via CMAUP via CMAUP
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	10000 nM	Potency	via CMAUP
CHEMBL1929	P47989	Xanthine dehydrogenase	700 nM 3200 nM 520 nM	IC50 IC50 Ki	PMID: 9461655 PMID: 26022844 via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.85%	91.11%
CHEMBL242	Q92731	Estrogen receptor beta	94.77%	98.35%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.20%	89.00%
CHEMBL2581	P07339	Cathepsin D	92.99%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.37%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.26%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.24%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.89%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	84.73%	94.73%
CHEMBL3038469	P24941	CDK2/Cyclin A	83.68%	91.38%
CHEMBL2208	P49137	MAP kinase-activated protein kinase 2	83.55%	95.20%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.09%	94.45%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	82.88%	89.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.85%	86.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.29%	93.99%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	80.96%	83.57%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

PubChem	5280443
NPASS	NPC50898
ChEMBL	CHEMBL28
LOTUS	LTS0104946
wikiData	Q424567

Apigenin

Table of Contents

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties (via admetSAR 2)

Targets

Proven Targets:

Predicted Targets (via Super-PRED):

Plants that contains it

Cross-Links