Methyl 3-(3,4-dihydroxyphenyl)-2-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]propanoate

Details

• Internal ID: 6be158b0-09d3-4533-bc1c-2dad99791bc7
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: methyl 3-(3,4-dihydroxyphenyl)-2-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]propanoate
• SMILES (Canonical): COC(=O)C(CC1=CC(=C(C=C1)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O
• SMILES (Isomeric): COC(=O)C(CC1=CC(=C(C=C1)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O
• InChI: InChI=1S/C19H18O8/c1-26-19(25)17(10-12-3-6-14(21)16(23)9-12)27-18(24)7-4-11-2-5-13(20)15(22)8-11/h2-9,17,20-23H,10H2,1H3
• InChI Key: XHALVRQBZGZHFE-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₈O₈
• Molecular Weight: 374.30 g/mol
• Exact Mass: 374.10016753 g/mol
• Topological Polar Surface Area (TPSA): 134.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 1.85
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8813	88.13%
Caco-2	-	0.7677	76.77%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8484	84.84%
OATP2B1 inhibitior	-	0.5790	57.90%
OATP1B1 inhibitior	+	0.9402	94.02%
OATP1B3 inhibitior	+	0.9469	94.69%
MATE1 inhibitior	+	0.8200	82.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7388	73.88%
P-glycoprotein inhibitior	-	0.6801	68.01%
P-glycoprotein substrate	-	0.8193	81.93%
CYP3A4 substrate	+	0.5077	50.77%
CYP2C9 substrate	-	0.5898	58.98%
CYP2D6 substrate	-	0.8417	84.17%
CYP3A4 inhibition	-	0.7495	74.95%
CYP2C9 inhibition	+	0.5330	53.30%
CYP2C19 inhibition	-	0.6684	66.84%
CYP2D6 inhibition	-	0.8325	83.25%
CYP1A2 inhibition	+	0.5102	51.02%
CYP2C8 inhibition	+	0.5588	55.88%
CYP inhibitory promiscuity	-	0.6834	68.34%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7647	76.47%
Carcinogenicity (trinary)	Non-required	0.6210	62.10%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.7307	73.07%
Skin irritation	-	0.7645	76.45%
Skin corrosion	-	0.9343	93.43%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6833	68.33%
Micronuclear	+	0.6759	67.59%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.8289	82.89%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	-	0.8390	83.90%
Acute Oral Toxicity (c)	III	0.6939	69.39%
Estrogen receptor binding	+	0.9004	90.04%
Androgen receptor binding	+	0.8807	88.07%
Thyroid receptor binding	+	0.5870	58.70%
Glucocorticoid receptor binding	+	0.6871	68.71%
Aromatase binding	-	0.5480	54.80%
PPAR gamma	+	0.5314	53.14%
Honey bee toxicity	-	0.7563	75.63%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9898	98.98%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL321	P14780	Matrix metalloproteinase 9	610 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.23%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.69%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.58%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.48%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.22%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.89%	86.33%
CHEMBL2581	P07339	Cathepsin D	92.35%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.58%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.67%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.01%	95.50%
CHEMBL221	P23219	Cyclooxygenase-1	83.96%	90.17%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	83.88%	100.00%
CHEMBL4208	P20618	Proteasome component C5	82.07%	90.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.44%	95.17%
CHEMBL3194	P02766	Transthyretin	81.29%	90.71%
CHEMBL2535	P11166	Glucose transporter	80.05%	98.75%

Plants that contains it

• Bourreria pulchra
• Cordia sebestena
• Glechoma hederacea
• Melissa officinalis
• Origanum dictamnus
• Perilla frutescens
• Salvia miltiorrhiza
• Salvia prionitis

Cross-Links

• PubChem: 76511959
• LOTUS: LTS0047172
• wikiData: Q104888800