(E)-3-(3-hydroxyphenyl)-1-(2,3,4-trihydroxyphenyl)prop-2-en-1-one

Details

• Internal ID: c820a8be-685e-464f-925b-6d959ce7fd1d
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > 2-Hydroxychalcones
• IUPAC Name: (E)-3-(3-hydroxyphenyl)-1-(2,3,4-trihydroxyphenyl)prop-2-en-1-one
• SMILES (Canonical): C1=CC(=CC(=C1)O)C=CC(=O)C2=C(C(=C(C=C2)O)O)O
• SMILES (Isomeric): C1=CC(=CC(=C1)O)/C=C/C(=O)C2=C(C(=C(C=C2)O)O)O
• InChI: InChI=1S/C15H12O5/c16-10-3-1-2-9(8-10)4-6-12(17)11-5-7-13(18)15(20)14(11)19/h1-8,16,18-20H/b6-4+
• InChI Key: GADGMUTUOCVUJQ-GQCTYLIASA-N
• Popularity: 1 reference 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

• CHEMBL1082538

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9623	96.23%
Caco-2	+	0.6283	62.83%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5982	59.82%
OATP2B1 inhibitior	-	0.5619	56.19%
OATP1B1 inhibitior	+	0.9479	94.79%
OATP1B3 inhibitior	+	0.9757	97.57%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.9588	95.88%
BSEP inhibitior	-	0.6515	65.15%
P-glycoprotein inhibitior	-	0.9416	94.16%
P-glycoprotein substrate	-	0.9437	94.37%
CYP3A4 substrate	-	0.6064	60.64%
CYP2C9 substrate	-	0.8069	80.69%
CYP2D6 substrate	-	0.8554	85.54%
CYP3A4 inhibition	+	0.6787	67.87%
CYP2C9 inhibition	+	0.5111	51.11%
CYP2C19 inhibition	-	0.8768	87.68%
CYP2D6 inhibition	-	0.9263	92.63%
CYP1A2 inhibition	+	0.8928	89.28%
CYP2C8 inhibition	+	0.7074	70.74%
CYP inhibitory promiscuity	+	0.6625	66.25%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8023	80.23%
Carcinogenicity (trinary)	Non-required	0.6207	62.07%
Eye corrosion	-	0.9801	98.01%
Eye irritation	+	0.9168	91.68%
Skin irritation	+	0.6631	66.31%
Skin corrosion	-	0.8127	81.27%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8553	85.53%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	-	0.5976	59.76%
skin sensitisation	+	0.9334	93.34%
Respiratory toxicity	-	0.7333	73.33%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.7000	70.00%
Nephrotoxicity	-	0.8326	83.26%
Acute Oral Toxicity (c)	III	0.7755	77.55%
Estrogen receptor binding	+	0.9464	94.64%
Androgen receptor binding	+	0.8896	88.96%
Thyroid receptor binding	+	0.6647	66.47%
Glucocorticoid receptor binding	+	0.9578	95.78%
Aromatase binding	+	0.9108	91.08%
PPAR gamma	+	0.8962	89.62%
Honey bee toxicity	-	0.9074	90.74%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.7755	77.55%
Fish aquatic toxicity	+	0.9889	98.89%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.72%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.21%	86.33%
CHEMBL3194	P02766	Transthyretin	94.84%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.43%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.28%	99.15%
CHEMBL1951	P21397	Monoamine oxidase A	87.74%	91.49%
CHEMBL2581	P07339	Cathepsin D	87.62%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.51%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	86.53%	94.73%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	86.05%	91.71%
CHEMBL2535	P11166	Glucose transporter	85.29%	98.75%
CHEMBL1929	P47989	Xanthine dehydrogenase	83.02%	96.12%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.93%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.83%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.53%	89.00%

Plants that contains it

• Aizoon africanum

Cross-Links

• PubChem: 45279391
• LOTUS: LTS0061747
• wikiData: Q105005316