Naringenin

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	951d9fb7-bc50-4be3-974d-1da583063cf5
Taxonomy	Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavanones
IUPAC Name	(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
SMILES (Canonical)	C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O
SMILES (Isomeric)	C1[C@H](OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O
InChI	InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2/t13-/m0/s1
InChI Key	FTVWIRXFELQLPI-ZDUSSCGKSA-N
Popularity	2,371 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₅H₁₂O₅
Molecular Weight	272.25 g/mol
Exact Mass	272.06847348 g/mol
Topological Polar Surface Area (TPSA)	87.00 Å²
XlogP	2.40
Atomic LogP (AlogP)	2.51
H-Bond Acceptor	5
H-Bond Donor	3
Rotatable Bonds	1

Synonyms

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480-41-1

Salipurol

(S)-Naringenin

(S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one

pelargidanon

naringetol

(2S)-Naringenin

salipurpol

Naringenine

Asahina

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	+	0.9450	94.50%
Caco-2	+	0.5424	54.24%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7583	75.83%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8076	80.76%
P-glycoprotein inhibitior	-	0.8953	89.53%
P-glycoprotein substrate	-	0.9501	95.01%
CYP3A4 substrate	-	0.5390	53.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7429	74.29%
CYP3A4 inhibition	+	0.8988	89.88%
CYP2C9 inhibition	+	0.8949	89.49%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	-	0.7463	74.63%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	-	0.6645	66.45%
CYP inhibitory promiscuity	+	0.7121	71.21%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6152	61.52%
Eye corrosion	-	0.9920	99.20%
Eye irritation	+	0.9751	97.51%
Skin irritation	-	0.5127	51.27%
Skin corrosion	-	0.9616	96.16%
Ames mutagenesis	-	0.5254	52.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.8099	80.99%
Micronuclear	+	0.8059	80.59%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.8697	86.97%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.6478	64.78%
Acute Oral Toxicity (c)	II	0.3682	36.82%
Estrogen receptor binding	+	0.6700	67.00%
Androgen receptor binding	+	0.7721	77.21%
Thyroid receptor binding	+	0.6578	65.78%
Glucocorticoid receptor binding	+	0.7525	75.25%
Aromatase binding	+	0.7256	72.56%
PPAR gamma	+	0.7947	79.47%
Honey bee toxicity	-	0.8458	84.58%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.7714	77.14%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1900	P15121	Aldose reductase	28870 nM	IC50	PMID: 22261024
CHEMBL3729	P22748	Carbonic anhydrase IV	79.5 nM 79.5 nM	Ki Ki	via Super-PRED PMID: 26498393
CHEMBL2326	P43166	Carbonic anhydrase VII	4.3 nM 4.3 nM	Ki Ki	via Super-PRED PMID: 26498393
CHEMBL3242	O43570	Carbonic anhydrase XII	44.3 nM 44.3 nM	Ki Ki	via Super-PRED PMID: 26498393
CHEMBL5586	P16152	Carbonyl reductase [NADPH] 1	21480 nM	IC50	PMID: 19097799
CHEMBL1978	P11511	Cytochrome P450 19A1	3300 nM 2.9 nM 1000 nM 1200 nM 1200 nM 230 nM 230 nM 230 nM 2.9 nM	IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50	PMID: 24074257 via Super-PRED PMID: 27155469 PMID: 24992702 PMID: 23994869 PMID: 23142320 PMID: 22115839 PMID: 21978950 PMID: 20413308
CHEMBL2231	P04798	Cytochrome P450 1A1	15167 nM	IC50	PMID: 20696580
CHEMBL3356	P05177	Cytochrome P450 1A2	26339 nM	IC50	PMID: 20696580
CHEMBL4878	Q16678	Cytochrome P450 1B1	3656 nM	IC50	PMID: 20696580
CHEMBL3622	P33261	Cytochrome P450 2C19	7943.3 nM 3981.1 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	12589.3 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	5011.9 nM 5011.9 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL284	P27487	Dipeptidyl peptidase IV	240 nM	IC50	via Super-PRED
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	19952.6 nM	Potency	via CMAUP
CHEMBL3181	P14061	Estradiol 17-beta-dehydrogenase 1	4960 nM	IC50	PMID: 18533708
CHEMBL2789	P37059	Estradiol 17-beta-dehydrogenase 2	14400 nM	IC50	PMID: 18533708
CHEMBL242	Q92731	Estrogen receptor beta	13473 nM	IC50	PMID: 17149865
CHEMBL262	P49841	Glycogen synthase kinase-3 beta	45700 nM	IC50	DOI: 10.1007/s00044-012-0353-y
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	2400 nM 20800 nM	Ki Ki	PMID: 19725578 PMID: 11306701
CHEMBL3305	P04278	Testis-specific androgen-binding protein	954.99 nM	Kd	via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	7079.5 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.47%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.91%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.59%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.54%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.09%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.57%	99.23%
CHEMBL2581	P07339	Cathepsin D	88.51%	98.95%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	88.10%	85.11%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	87.29%	93.40%
CHEMBL3194	P02766	Transthyretin	85.59%	90.71%
CHEMBL1929	P47989	Xanthine dehydrogenase	85.57%	96.12%
CHEMBL4208	P20618	Proteasome component C5	84.95%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.27%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.95%	96.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.67%	90.71%

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.

Acer pictum subsp. mono

Anastatica hierochuntica