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

Details

• Internal ID: a60c7a3d-fc0d-4309-8654-72a68bed52ee
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: dimethyl (2S)-2-hydroxy-2-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]butanedioate
• InChI: InChI=1S/C17H20O9/c1-23-13-8-11(4-6-12(13)18)5-7-14(19)26-10-17(22,16(21)25-3)9-15(20)24-2/h4-8,18,22H,9-10H2,1-3H3/b7-5+/t17-/m0/s1
• InChI Key: JINNYRORWXGFBA-UABRLCRWSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₀O₉
• Molecular Weight: 368.30 g/mol
• Exact Mass: 368.11073221 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 0.42
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9827	98.27%
Caco-2	+	0.5279	52.79%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8059	80.59%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9134	91.34%
OATP1B3 inhibitior	+	0.9092	90.92%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8244	82.44%
P-glycoprotein inhibitior	-	0.4937	49.37%
P-glycoprotein substrate	-	0.7763	77.63%
CYP3A4 substrate	+	0.5400	54.00%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8314	83.14%
CYP3A4 inhibition	-	0.8147	81.47%
CYP2C9 inhibition	-	0.8714	87.14%
CYP2C19 inhibition	-	0.9010	90.10%
CYP2D6 inhibition	-	0.9137	91.37%
CYP1A2 inhibition	-	0.7647	76.47%
CYP2C8 inhibition	+	0.7781	77.81%
CYP inhibitory promiscuity	-	0.9527	95.27%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8128	81.28%
Carcinogenicity (trinary)	Non-required	0.6983	69.83%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.8940	89.40%
Skin irritation	-	0.7456	74.56%
Skin corrosion	-	0.9632	96.32%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4654	46.54%
Micronuclear	-	0.5827	58.27%
Hepatotoxicity	-	0.7176	71.76%
skin sensitisation	-	0.5678	56.78%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.8536	85.36%
Acute Oral Toxicity (c)	III	0.6035	60.35%
Estrogen receptor binding	+	0.9295	92.95%
Androgen receptor binding	+	0.8010	80.10%
Thyroid receptor binding	+	0.5300	53.00%
Glucocorticoid receptor binding	+	0.6872	68.72%
Aromatase binding	+	0.7210	72.10%
PPAR gamma	+	0.5287	52.87%
Honey bee toxicity	-	0.8849	88.49%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5561	55.61%
Fish aquatic toxicity	+	0.9512	95.12%

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	98.72%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.62%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.54%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.78%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.94%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.80%	95.56%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.15%	89.62%
CHEMBL3401	O75469	Pregnane X receptor	85.76%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.73%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	85.60%	91.49%
CHEMBL4208	P20618	Proteasome component C5	84.26%	90.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.91%	85.14%
CHEMBL3194	P02766	Transthyretin	82.04%	90.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.07%	92.62%

Plants that contains it

• Lilium longiflorum

Cross-Links

• PubChem: 163190410
• LOTUS: LTS0258702
• wikiData: Q105129207