2',4,4',6-Tetrahydroxychalcone

Details

• Internal ID: 5b3ba8e3-b05c-4242-9a69-07017c01f74e
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > 2-Hydroxychalcones
• IUPAC Name: 1,3-bis(2,4-dihydroxyphenyl)prop-2-en-1-one
• SMILES (Canonical): C1=CC(=C(C=C1O)O)C=CC(=O)C2=C(C=C(C=C2)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1O)O)C=CC(=O)C2=C(C=C(C=C2)O)O
• InChI: InChI=1S/C15H12O5/c16-10-3-1-9(14(19)7-10)2-6-13(18)12-5-4-11(17)8-15(12)20/h1-8,16-17,19-20H
• InChI Key: ZWTDXYUDJYDHJR-UHFFFAOYSA-N
• Popularity: 5 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

• 2',4,4',6-tetrahydroxychalcone
• 2,4,2',4'- tetrahydroxychalcone
• PD150341

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9856	98.56%
Caco-2	+	0.9131	91.31%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7711	77.11%
OATP2B1 inhibitior	-	0.5537	55.37%
OATP1B1 inhibitior	+	0.9064	90.64%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9838	98.38%
BSEP inhibitior	-	0.7525	75.25%
P-glycoprotein inhibitior	-	0.9383	93.83%
P-glycoprotein substrate	-	0.9376	93.76%
CYP3A4 substrate	-	0.6524	65.24%
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	+	0.5416	54.16%
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	+	0.9848	98.48%
Skin irritation	+	0.6928	69.28%
Skin corrosion	-	0.9313	93.13%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8429	84.29%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	-	0.5697	56.97%
skin sensitisation	+	0.8772	87.72%
Respiratory toxicity	-	0.7000	70.00%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.7000	70.00%
Nephrotoxicity	-	0.6013	60.13%
Acute Oral Toxicity (c)	III	0.7921	79.21%
Estrogen receptor binding	+	0.8506	85.06%
Androgen receptor binding	+	0.8888	88.88%
Thyroid receptor binding	+	0.6598	65.98%
Glucocorticoid receptor binding	+	0.8713	87.13%
Aromatase binding	+	0.8657	86.57%
PPAR gamma	+	0.8657	86.57%
Honey bee toxicity	-	0.9176	91.76%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9906	99.06%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1973	P14679	Tyrosinase	70 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.21%	91.11%
CHEMBL3194	P02766	Transthyretin	95.57%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.59%	95.56%
CHEMBL2581	P07339	Cathepsin D	87.17%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.32%	86.33%
CHEMBL4208	P20618	Proteasome component C5	85.79%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.78%	89.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	82.11%	93.40%
CHEMBL2535	P11166	Glucose transporter	81.43%	98.75%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.26%	91.71%
CHEMBL3401	O75469	Pregnane X receptor	80.02%	94.73%

Plants that contains it

• Broussonetia papyrifera
• Buddleja globosa
• Morus nigra

Cross-Links

• PubChem: 54570259
• LOTUS: LTS0253447
• wikiData: Q104983707