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

Details

• Internal ID: 1df89b66-0dc6-4807-8faa-cd1ab4b64cc0
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: methyl 3-[4-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]phenyl]prop-2-enoate
• SMILES (Canonical): COC(=O)C=CC1=CC=C(C=C1)OC(=O)C=CC2=CC(=C(C=C2)O)O
• SMILES (Isomeric): COC(=O)C=CC1=CC=C(C=C1)OC(=O)C=CC2=CC(=C(C=C2)O)O
• InChI: InChI=1S/C19H16O6/c1-24-18(22)10-5-13-2-7-15(8-3-13)25-19(23)11-6-14-4-9-16(20)17(21)12-14/h2-12,20-21H,1H3
• InChI Key: XJNYOFXGMISJPS-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₆O₆
• Molecular Weight: 340.30 g/mol
• Exact Mass: 340.09468823 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 2.90
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9628	96.28%
Caco-2	-	0.5478	54.78%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8374	83.74%
OATP2B1 inhibitior	-	0.5778	57.78%
OATP1B1 inhibitior	+	0.9615	96.15%
OATP1B3 inhibitior	+	0.9532	95.32%
MATE1 inhibitior	+	0.6200	62.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8044	80.44%
P-glycoprotein inhibitior	-	0.6637	66.37%
P-glycoprotein substrate	-	0.9619	96.19%
CYP3A4 substrate	-	0.5520	55.20%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8590	85.90%
CYP3A4 inhibition	-	0.8790	87.90%
CYP2C9 inhibition	+	0.5667	56.67%
CYP2C19 inhibition	-	0.6973	69.73%
CYP2D6 inhibition	-	0.9236	92.36%
CYP1A2 inhibition	+	0.5509	55.09%
CYP2C8 inhibition	-	0.5586	55.86%
CYP inhibitory promiscuity	-	0.8028	80.28%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7189	71.89%
Carcinogenicity (trinary)	Non-required	0.5583	55.83%
Eye corrosion	-	0.9800	98.00%
Eye irritation	+	0.7374	73.74%
Skin irritation	-	0.6584	65.84%
Skin corrosion	-	0.9080	90.80%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4591	45.91%
Micronuclear	+	0.8100	81.00%
Hepatotoxicity	-	0.6105	61.05%
skin sensitisation	-	0.8385	83.85%
Respiratory toxicity	-	0.7222	72.22%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.6875	68.75%
Nephrotoxicity	+	0.4587	45.87%
Acute Oral Toxicity (c)	III	0.4943	49.43%
Estrogen receptor binding	+	0.9087	90.87%
Androgen receptor binding	+	0.8727	87.27%
Thyroid receptor binding	+	0.6572	65.72%
Glucocorticoid receptor binding	+	0.8620	86.20%
Aromatase binding	+	0.7353	73.53%
PPAR gamma	+	0.8267	82.67%
Honey bee toxicity	-	0.8197	81.97%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9948	99.48%

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	99.15%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.59%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.54%	86.33%
CHEMBL4208	P20618	Proteasome component C5	92.51%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.20%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.77%	96.09%
CHEMBL3194	P02766	Transthyretin	87.48%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.38%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	86.57%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.76%	99.15%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.61%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.42%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.35%	89.00%

Plants that contains it

• Ligularia vellerea

Cross-Links

• PubChem: 162937676
• LOTUS: LTS0067577
• wikiData: Q105329082