2-[(E)-3-(3,4-Dimethoxyphenyl)prop-2-enoyl]oxybutanedioic acid

Details

• Internal ID: d5c1fc5a-13c0-413c-97ad-161f2d346e58
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: 2-[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxybutanedioic acid
• SMILES (Canonical): COC1=C(C=C(C=C1)C=CC(=O)OC(CC(=O)O)C(=O)O)OC
• SMILES (Isomeric): COC1=C(C=C(C=C1)/C=C/C(=O)OC(CC(=O)O)C(=O)O)OC
• InChI: InChI=1S/C15H16O8/c1-21-10-5-3-9(7-11(10)22-2)4-6-14(18)23-12(15(19)20)8-13(16)17/h3-7,12H,8H2,1-2H3,(H,16,17)(H,19,20)/b6-4+
• InChI Key: FZQDBBBREHNBJN-GQCTYLIASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₈
• Molecular Weight: 324.28 g/mol
• Exact Mass: 324.08451746 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.19
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

• (E)-2-(3-(3,4-dimethoxyphenyl)acryloyloxy)succinic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9720	97.20%
Caco-2	-	0.6202	62.02%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7395	73.95%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.9211	92.11%
OATP1B3 inhibitior	+	0.9417	94.17%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6254	62.54%
P-glycoprotein inhibitior	-	0.9110	91.10%
P-glycoprotein substrate	-	0.8173	81.73%
CYP3A4 substrate	-	0.5300	53.00%
CYP2C9 substrate	-	0.5976	59.76%
CYP2D6 substrate	-	0.8492	84.92%
CYP3A4 inhibition	-	0.9061	90.61%
CYP2C9 inhibition	-	0.9121	91.21%
CYP2C19 inhibition	-	0.8922	89.22%
CYP2D6 inhibition	-	0.8534	85.34%
CYP1A2 inhibition	-	0.8383	83.83%
CYP2C8 inhibition	+	0.5825	58.25%
CYP inhibitory promiscuity	-	0.9524	95.24%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8018	80.18%
Carcinogenicity (trinary)	Non-required	0.7387	73.87%
Eye corrosion	-	0.9337	93.37%
Eye irritation	-	0.8568	85.68%
Skin irritation	-	0.6362	63.62%
Skin corrosion	-	0.9215	92.15%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5624	56.24%
Micronuclear	+	0.6794	67.94%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.6835	68.35%
Respiratory toxicity	-	0.7000	70.00%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.8469	84.69%
Acute Oral Toxicity (c)	III	0.5632	56.32%
Estrogen receptor binding	+	0.6233	62.33%
Androgen receptor binding	+	0.6774	67.74%
Thyroid receptor binding	-	0.7089	70.89%
Glucocorticoid receptor binding	+	0.6017	60.17%
Aromatase binding	-	0.5696	56.96%
PPAR gamma	-	0.7937	79.37%
Honey bee toxicity	-	0.9118	91.18%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6255	62.55%
Fish aquatic toxicity	+	0.9310	93.10%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	98.62%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.61%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.23%	86.33%
CHEMBL1255126	O15151	Protein Mdm4	94.15%	90.20%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.10%	99.17%
CHEMBL4040	P28482	MAP kinase ERK2	92.50%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.76%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.32%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.84%	95.56%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.40%	89.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.50%	89.00%

Plants that contains it

• Isodon rubescens

Cross-Links

• PubChem: 90471964
• NPASS: NPC68932