Naringenin chalcone

Details

• Internal ID: 0be404e5-6539-4229-9680-dd519f6aa3e5
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > 2-Hydroxychalcones
• IUPAC Name: (E)-3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
• SMILES (Canonical): C1=CC(=CC=C1C=CC(=O)C2=C(C=C(C=C2O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C(=O)C2=C(C=C(C=C2O)O)O)O
• InChI: InChI=1S/C15H12O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-8,16-17,19-20H/b6-3+
• InChI Key: YQHMWTPYORBCMF-ZZXKWVIFSA-N
• Popularity: 100 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₅
• Molecular Weight: 272.25 g/mol
• Exact Mass: 272.06847348 g/mol
• Topological Polar Surface Area (TPSA): 98.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.41
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• Chalconaringenin
• 73692-50-9
• Isosalipurpol
• 2',4,4',6'-Tetrahydroxychalcone
• 25515-46-2
• Chalcononaringenin
• (2E)-3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
• trans-2',4,4',6'-Tetrahydroxychalcone
• 2',4',6',4-tetrahydroxychalcone
• (E)-3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
• YCF6Z24AS2
• 2,4,4,6-tetrahydroxychalcone
• CHEMBL338066
• 4,2,4,6-Tetrahydroxychalcone
• CHEBI:15413
• Chalcone, 2,4,4,6-tetrahydroxy-
• 4,2',4',6'-TETRAHYDROXYCHALCONE
• 3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-2-propen-1-one
• (2E)- 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-2-Propen-1-one
• (2E)-3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-2-propen-1-one
• 2-Propen-1-one, 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-, (2E)-
• 2-Propen-1-one, 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-
• Naringenin chalcon
• UNII-YCF6Z24AS2
• MLS000863595
• 2'4'6'4-Tetrahydroxychalcone
• MEGxp0_001759
• ACon1_001222
• YQHMWTPYORBCMF-ZZXKWVIFSA-N
• DTXSID101043553
• HMS2269F17
• HY-N3007
• BDBM50042993
• LMPK12120264
• MFCD00016762
• trans-2'4'6'4-tetrahydroxychalcone
• AKOS037515150
• CCG-267176
• 2'',4,4'',6''-tetrahydroxychalcone
• NCGC00142554-01
• NCGC00142554-02
• AC-34933
• MS-23851
• SMR000440735
• CS-0022919
• S9440
• C06561
• Q25098661
• 3-(4-hydroxyphemyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
• 3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-2-propen-1-one, 9CI

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9856	98.56%
Caco-2	+	0.9451	94.51%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7711	77.11%
OATP2B1 inhibitior	-	0.5600	56.00%
OATP1B1 inhibitior	+	0.9395	93.95%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9838	98.38%
BSEP inhibitior	-	0.6120	61.20%
P-glycoprotein inhibitior	-	0.9130	91.30%
P-glycoprotein substrate	-	0.9609	96.09%
CYP3A4 substrate	-	0.6632	66.32%
CYP2C9 substrate	-	0.6211	62.11%
CYP2D6 substrate	-	0.8534	85.34%
CYP3A4 inhibition	+	0.7959	79.59%
CYP2C9 inhibition	+	0.8949	89.49%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.9350	93.50%
CYP2C8 inhibition	+	0.6042	60.42%
CYP inhibitory promiscuity	+	0.8559	85.59%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.7472	74.72%
Carcinogenicity (trinary)	Non-required	0.7048	70.48%
Eye corrosion	-	0.9801	98.01%
Eye irritation	+	0.9901	99.01%
Skin irritation	+	0.6928	69.28%
Skin corrosion	-	0.9313	93.13%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8149	81.49%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	-	0.7068	70.68%
skin sensitisation	+	0.8772	87.72%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.7000	70.00%
Nephrotoxicity	-	0.5751	57.51%
Acute Oral Toxicity (c)	III	0.7921	79.21%
Estrogen receptor binding	+	0.9018	90.18%
Androgen receptor binding	+	0.8771	87.71%
Thyroid receptor binding	+	0.6728	67.28%
Glucocorticoid receptor binding	+	0.8948	89.48%
Aromatase binding	+	0.9371	93.71%
PPAR gamma	+	0.9308	93.08%
Honey bee toxicity	-	0.9282	92.82%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9906	99.06%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL340	P08684	Cytochrome P450 3A4	7943.3 nM; 7943.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	1412.5 nM; 794.3 nM; 794.3 nM	Potency; Potency; Potency	via CMAUP; via Super-PRED; via CMAUP
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	4000 nM	EC50	PMID: 25232969

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.49%	91.11%
CHEMBL3194	P02766	Transthyretin	96.26%	90.71%
CHEMBL1929	P47989	Xanthine dehydrogenase	90.82%	96.12%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.87%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.04%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.64%	89.00%
CHEMBL4208	P20618	Proteasome component C5	87.33%	90.00%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	82.56%	90.93%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.02%	91.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.34%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.70%	99.17%
CHEMBL242	Q92731	Estrogen receptor beta	80.44%	98.35%

Plants that contains it

• Arabidopsis thaliana
• Ginkgo biloba
• Humulus lupulus
• Ipomoea nil
• Matthiola incana
• Populus cathayana
• Populus suaveolens
• Populus tremula
• Salvia leucantha
• Salvia xalapensis

Cross-Links

• PubChem: 5280960
• NPASS: NPC73532
• ChEMBL: CHEMBL338066
• LOTUS: LTS0209404
• wikiData: Q25098661