Phyto4Health

Naringenin

Representations & DB's id

ChEBI: CHEBI:17846
ChEMBL: CHEMBL9352
PubChem: 439246
IUPAC: (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
Standard 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
Standard InChI Key: FTVWIRXFELQLPI-ZDUSSCGKSA-N
SMILES: Oc1ccc(cc1)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O

Molecular propeties

AlogP: 2.51
Hydrogen bonds acceptors: 5
Hydrogen bonds donors: 3
Rotatable bonds: 1
Number of rings: 3
Molecular Weight: 272.07
Topological polar surface area: 87
Number of aromatic rings: 2
Fsp3: 0.133
Number of carbons: 15

Plant sources

Part of plant Plant name Ref.
PlantOrthosiphon stamineus
PlantOrthosiphon stamineus
PlantTrigonella foenum-graecum
PlantOryza sativa
ShootGlycyrrhiza glabra
RootGlycyrrhiza uralensis
RootGlycyrrhiza uralensis
PlantThymus vulgaris
PlantFoeniculum vulgare
PlantFerula assa-foetida
PlantHumulus lupulus
PlantMarrubium vulgare
PlantCrocus sativus

In vitro data

Activity Type Activity Value Target Name UniProt ID Ref.
IC5075302 nMEstrogen receptor alphaP03372
IC5013473 nMEstrogen receptor betaQ92731
Kd954.99 nMTestis-specific androgen-binding proteinP04278
Kd28183.83 nMTestis-specific androgen-binding proteinP04278
Others50 %Glyoxalase IQ04760
IC5017000 nMCytochrome P450 19A1P11511
Others6 %Phosphodiesterase 5AO76074
Others26.8 %Salivary alpha-amylaseP04745
Others207 %Canalicular multispecific organic anion transporter 1Q92887
Others4.7 %Carbonyl reductase [NADPH] 1P16152
IC5021480 nMCarbonyl reductase [NADPH] 1P16152
Ki3430 nMCarbonyl reductase [NADPH] 1P16152
Others17.2 %Estradiol 17-beta-dehydrogenase 1P14061
IC504960 nMEstradiol 17-beta-dehydrogenase 1P14061
Others12.6 %Estradiol 17-beta-dehydrogenase 2P37059
IC5014400 nMEstradiol 17-beta-dehydrogenase 2P37059
Others1 Peroxisome proliferator-activated receptor gammaP37231
Others1.7 Peroxisome proliferator-activated receptor gammaP37231
Others1.2 Peroxisome proliferator-activated receptor alphaQ07869
Others1.7 Peroxisome proliferator-activated receptor alphaQ07869
IC502.9 nMCytochrome P450 19A1P11511
IC503656 nMCytochrome P450 1B1Q16678
IC5015167 nMCytochrome P450 1A1P04798
IC5026339 nMCytochrome P450 1A2P05177
Potency7079.5 nMTyrosyl-DNA phosphodiesterase 1Q9NUW8
Potency7943.3 nMCytochrome P450 2C19P33261
Potency3981.1 nMCytochrome P450 2C19P33261
Potency19952.6 nMEndoplasmic reticulum-associated amyloid beta-peptide-binding proteinQ99714
Potency5011.9 nMCytochrome P450 3A4P08684
Potency5011.9 nMCytochrome P450 3A4P08684
Potency12589.3 nMCytochrome P450 2C9P11712
IC5022010 nMCalmodulinP62158
Others0.91 CalmodulinP62158
Others510 pm/min/mgUDP-glucuronosyltransferase 1-1P22309
Others95 pm/min/mgUDP-glucuronosyltransferase 1-1P22309
Others55 pm/min/mgUDP-glucuronosyltransferase 1-10Q9HAW8
Others612 pm/min/mgUDP-glucuronosyltransferase 1-3P35503
Others0 pm/min/mgUDP-glucuronosyltransferase 1A4P22310
Others1534 pm/min/mgUDP-glucuronosyltransferase 1-8Q9HAW9
Others1860 pm/min/mgUDP-glucuronosyltransferase 1-8Q9HAW9
Others103 pm/min/mgUDP-glucuronosyltransferase 2B15P54855
IC50230 nMCytochrome P450 19A1P11511
IC5028870 nMAldose reductaseP15121
IC502045000 nMAcetylcholinesteraseP22303
Potency4.6 nMGemininO75496
Others32.4 %Solute carrier organic anion transporter family member 2B1O94956
Others-57.2 %Solute carrier organic anion transporter family member 1B3Q9NPD5
Others34.8 %Solute carrier organic anion transporter family member 1B1Q9Y6L6
IC50230 nMCytochrome P450 19A1P11511
IC5045700 nMGlycogen synthase kinase-3 betaP49841
Others1.3 Peroxisome proliferator-activated receptor deltaQ03181
Others1.1 Peroxisome proliferator-activated receptor deltaQ03181
IC5010000 nMTyrosine-protein kinase receptor FLT3P36888
IC501200 nMCytochrome P450 19A1P11511
IC503300 nMCytochrome P450 19A1P11511
IC501200 nMCytochrome P450 19A1P11511
Ki10000 nMCarbonic anhydrase IIP00918
Ki10000 nMCarbonic anhydrase IP00915
Ki79.5 nMCarbonic anhydrase IVP22748
Ki4.3 nMCarbonic anhydrase VIIP43166
Ki44.3 nMCarbonic anhydrase XIIO43570
Others109.3 %Isocitrate dehydrogenase [NADP] cytoplasmicO75874
Others101.8 %Isocitrate dehydrogenase [NADP] cytoplasmicO75874
IC505100 nMCytochrome P450 19A1P11511
IC501000 nMCytochrome P450 19A1P11511