2-(3,4-Dihydroxybenzoyloxy)-4,6-dihydroxyphenylacetic acid

Details

• Internal ID: 85a7827a-e1f7-4a84-8bd2-85eebea83c99
• Taxonomy: Phenylpropanoids and polyketides > Depsides and depsidones
• IUPAC Name: 2-[2-(3,4-dihydroxybenzoyl)oxy-4,6-dihydroxyphenyl]acetic acid
• SMILES (Canonical): C1=CC(=C(C=C1C(=O)OC2=CC(=CC(=C2CC(=O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C(=O)OC2=CC(=CC(=C2CC(=O)O)O)O)O)O
• InChI: InChI=1S/C15H12O8/c16-8-4-11(18)9(6-14(20)21)13(5-8)23-15(22)7-1-2-10(17)12(19)3-7/h1-5,16-19H,6H2,(H,20,21)
• InChI Key: YTJJRAWFHJBAMT-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₈
• Molecular Weight: 320.25 g/mol
• Exact Mass: 320.05321734 g/mol
• Topological Polar Surface Area (TPSA): 145.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.36
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• CHEMBL521876
• SCHEMBL1771466
• AKOS040740088
• 2-(3,4-Dihydroxybenzoyloxy)-4,6-dihydroxyphenylacetic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8157	81.57%
Caco-2	-	0.8684	86.84%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6582	65.82%
OATP2B1 inhibitior	+	0.5658	56.58%
OATP1B1 inhibitior	+	0.9243	92.43%
OATP1B3 inhibitior	+	0.8252	82.52%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8079	80.79%
P-glycoprotein inhibitior	-	0.9461	94.61%
P-glycoprotein substrate	-	0.9292	92.92%
CYP3A4 substrate	-	0.6085	60.85%
CYP2C9 substrate	-	0.6031	60.31%
CYP2D6 substrate	-	0.8600	86.00%
CYP3A4 inhibition	-	0.8916	89.16%
CYP2C9 inhibition	-	0.9622	96.22%
CYP2C19 inhibition	-	0.9764	97.64%
CYP2D6 inhibition	-	0.9521	95.21%
CYP1A2 inhibition	-	0.8909	89.09%
CYP2C8 inhibition	+	0.8492	84.92%
CYP inhibitory promiscuity	-	0.9543	95.43%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8732	87.32%
Carcinogenicity (trinary)	Non-required	0.7126	71.26%
Eye corrosion	-	0.9927	99.27%
Eye irritation	+	0.9228	92.28%
Skin irritation	-	0.6804	68.04%
Skin corrosion	-	0.9378	93.78%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7069	70.69%
Micronuclear	+	0.7518	75.18%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.6241	62.41%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.7328	73.28%
Acute Oral Toxicity (c)	III	0.8310	83.10%
Estrogen receptor binding	+	0.8134	81.34%
Androgen receptor binding	+	0.7120	71.20%
Thyroid receptor binding	-	0.5135	51.35%
Glucocorticoid receptor binding	+	0.7231	72.31%
Aromatase binding	+	0.7848	78.48%
PPAR gamma	+	0.7457	74.57%
Honey bee toxicity	-	0.8562	85.62%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6999	69.99%
Fish aquatic toxicity	+	0.9723	97.23%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3194	P02766	Transthyretin	96.69%	90.71%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.24%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	94.75%	91.49%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.11%	99.17%
CHEMBL4208	P20618	Proteasome component C5	91.38%	90.00%
CHEMBL2581	P07339	Cathepsin D	89.60%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.12%	86.33%
CHEMBL2535	P11166	Glucose transporter	87.36%	98.75%
CHEMBL2216739	Q92523	Carnitine O-palmitoyltransferase 1, muscle isoform	86.59%	88.33%
CHEMBL1255126	O15151	Protein Mdm4	86.42%	90.20%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.37%	96.95%

Plants that contains it

• Papaver rhoeas

Cross-Links

• PubChem: 44583925
• NPASS: NPC262282
• ChEMBL: CHEMBL521876