(3S)-3-hydroxy-4-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy-4-oxobutanoic acid

Details

• Internal ID: 5115d4a6-87be-455e-b372-0fd187c1f0f6
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: (3S)-3-hydroxy-4-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy-4-oxobutanoic acid
• InChI: InChI=1S/C15H16O9/c1-22-10-5-8(6-11(23-2)14(10)20)3-4-13(19)24-15(21)9(16)7-12(17)18/h3-6,9,16,20H,7H2,1-2H3,(H,17,18)/b4-3+/t9-/m0/s1
• InChI Key: UKFVKXGKUQLPDS-NWALNABHSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₉
• Molecular Weight: 340.28 g/mol
• Exact Mass: 340.07943208 g/mol
• Topological Polar Surface Area (TPSA): 140.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 0.33
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9256	92.56%
Caco-2	-	0.7191	71.91%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6453	64.53%
OATP2B1 inhibitior	-	0.8604	86.04%
OATP1B1 inhibitior	+	0.8555	85.55%
OATP1B3 inhibitior	+	0.9344	93.44%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9088	90.88%
BSEP inhibitior	+	0.6996	69.96%
P-glycoprotein inhibitior	-	0.7561	75.61%
P-glycoprotein substrate	-	0.8004	80.04%
CYP3A4 substrate	-	0.5151	51.51%
CYP2C9 substrate	+	0.6016	60.16%
CYP2D6 substrate	-	0.8238	82.38%
CYP3A4 inhibition	-	0.7605	76.05%
CYP2C9 inhibition	-	0.7631	76.31%
CYP2C19 inhibition	-	0.7945	79.45%
CYP2D6 inhibition	-	0.7957	79.57%
CYP1A2 inhibition	-	0.8664	86.64%
CYP2C8 inhibition	+	0.5559	55.59%
CYP inhibitory promiscuity	-	0.9024	90.24%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8014	80.14%
Carcinogenicity (trinary)	Non-required	0.7726	77.26%
Eye corrosion	-	0.9423	94.23%
Eye irritation	-	0.6315	63.15%
Skin irritation	-	0.6322	63.22%
Skin corrosion	-	0.9203	92.03%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8075	80.75%
Micronuclear	+	0.6894	68.94%
Hepatotoxicity	-	0.6415	64.15%
skin sensitisation	-	0.6428	64.28%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.8502	85.02%
Acute Oral Toxicity (c)	III	0.6440	64.40%
Estrogen receptor binding	+	0.8319	83.19%
Androgen receptor binding	+	0.6853	68.53%
Thyroid receptor binding	+	0.5523	55.23%
Glucocorticoid receptor binding	+	0.7539	75.39%
Aromatase binding	+	0.5489	54.89%
PPAR gamma	+	0.5395	53.95%
Honey bee toxicity	-	0.8715	87.15%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9056	90.56%

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	97.85%	96.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.81%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.83%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.47%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.74%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.98%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.54%	99.17%
CHEMBL1255126	O15151	Protein Mdm4	86.37%	90.20%
CHEMBL3194	P02766	Transthyretin	85.50%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.37%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.71%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	82.41%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.37%	85.14%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.80%	89.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.33%	95.89%

Plants that contains it

• Arabidopsis thaliana

Cross-Links

• PubChem: 163191433
• LOTUS: LTS0200693
• wikiData: Q105274510