dimethyl (2S)-2-hydroxy-2-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]butanedioate

Details

• Internal ID: 77741641-5911-4761-9ad6-9aaf11e404c4
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: dimethyl (2S)-2-hydroxy-2-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]butanedioate
• InChI: InChI=1S/C16H18O8/c1-22-14(19)9-16(21,15(20)23-2)10-24-13(18)8-5-11-3-6-12(17)7-4-11/h3-8,17,21H,9-10H2,1-2H3/b8-5+/t16-/m0/s1
• InChI Key: AWXSGILAPNUJPW-WHWKNOJMSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₈O₈
• Molecular Weight: 338.31 g/mol
• Exact Mass: 338.10016753 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.42
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9819	98.19%
Caco-2	+	0.5394	53.94%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.8434	84.34%
OATP2B1 inhibitior	-	0.8589	85.89%
OATP1B1 inhibitior	+	0.8754	87.54%
OATP1B3 inhibitior	+	0.9250	92.50%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6663	66.63%
P-glycoprotein inhibitior	-	0.6876	68.76%
P-glycoprotein substrate	-	0.7905	79.05%
CYP3A4 substrate	+	0.5393	53.93%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8502	85.02%
CYP3A4 inhibition	-	0.8612	86.12%
CYP2C9 inhibition	-	0.8862	88.62%
CYP2C19 inhibition	-	0.9186	91.86%
CYP2D6 inhibition	-	0.9184	91.84%
CYP1A2 inhibition	-	0.8883	88.83%
CYP2C8 inhibition	+	0.7521	75.21%
CYP inhibitory promiscuity	-	0.9622	96.22%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7628	76.28%
Carcinogenicity (trinary)	Non-required	0.6952	69.52%
Eye corrosion	-	0.9839	98.39%
Eye irritation	-	0.6898	68.98%
Skin irritation	-	0.7400	74.00%
Skin corrosion	-	0.9657	96.57%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6715	67.15%
Micronuclear	-	0.6227	62.27%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.5604	56.04%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.6143	61.43%
Acute Oral Toxicity (c)	III	0.6321	63.21%
Estrogen receptor binding	+	0.8843	88.43%
Androgen receptor binding	+	0.8262	82.62%
Thyroid receptor binding	-	0.5946	59.46%
Glucocorticoid receptor binding	+	0.7321	73.21%
Aromatase binding	+	0.6052	60.52%
PPAR gamma	-	0.5269	52.69%
Honey bee toxicity	-	0.8636	86.36%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6417	64.17%
Fish aquatic toxicity	+	0.8900	89.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.27%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.80%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.10%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.06%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.39%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	87.29%	94.73%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	87.28%	89.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.02%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	84.75%	83.82%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.19%	85.14%

Plants that contains it

• Lilium longiflorum

Cross-Links

• PubChem: 163185200
• LOTUS: LTS0161828
• wikiData: Q104920361