[(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Details

• Internal ID: b2afaaa2-ce38-4a1e-ba50-a2a51eb2145c
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OCC2C(C(C(C(O2)OCCC3=CC(=C(C=C3)O)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OCCC3=CC(=C(C=C3)O)O)O)O)O)O
• InChI: InChI=1S/C24H28O11/c1-32-18-11-13(3-6-16(18)26)4-7-20(28)34-12-19-21(29)22(30)23(31)24(35-19)33-9-8-14-2-5-15(25)17(27)10-14/h2-7,10-11,19,21-27,29-31H,8-9,12H2,1H3/b7-4+/t19-,21-,22+,23-,24-/m1/s1
• InChI Key: VZFVTZAODLQTMX-STMWSHLUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₈O₁₁
• Molecular Weight: 492.50 g/mol
• Exact Mass: 492.16316171 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.44
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6664	66.64%
Caco-2	-	0.8891	88.91%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7819	78.19%
OATP2B1 inhibitior	-	0.8523	85.23%
OATP1B1 inhibitior	+	0.8845	88.45%
OATP1B3 inhibitior	+	0.9578	95.78%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6242	62.42%
P-glycoprotein inhibitior	-	0.5203	52.03%
P-glycoprotein substrate	-	0.7714	77.14%
CYP3A4 substrate	+	0.6275	62.75%
CYP2C9 substrate	-	0.8024	80.24%
CYP2D6 substrate	-	0.8502	85.02%
CYP3A4 inhibition	-	0.8743	87.43%
CYP2C9 inhibition	-	0.6498	64.98%
CYP2C19 inhibition	-	0.7131	71.31%
CYP2D6 inhibition	-	0.8798	87.98%
CYP1A2 inhibition	-	0.7276	72.76%
CYP2C8 inhibition	+	0.8078	80.78%
CYP inhibitory promiscuity	-	0.6367	63.67%
UGT catelyzed	+	0.6362	63.62%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6706	67.06%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9216	92.16%
Skin irritation	-	0.8324	83.24%
Skin corrosion	-	0.9479	94.79%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3956	39.56%
Micronuclear	-	0.5967	59.67%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8545	85.45%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.9451	94.51%
Acute Oral Toxicity (c)	III	0.7783	77.83%
Estrogen receptor binding	+	0.7656	76.56%
Androgen receptor binding	+	0.5508	55.08%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6546	65.46%
Aromatase binding	-	0.5481	54.81%
PPAR gamma	+	0.5552	55.52%
Honey bee toxicity	-	0.7662	76.62%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.8190	81.90%

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	99.34%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.09%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.49%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.24%	96.00%
CHEMBL3194	P02766	Transthyretin	95.21%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.11%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.99%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	89.89%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	88.83%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.34%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.42%	96.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.51%	95.56%
CHEMBL4208	P20618	Proteasome component C5	83.74%	90.00%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.71%	80.78%
CHEMBL2581	P07339	Cathepsin D	82.92%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.84%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.77%	86.92%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.72%	92.62%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.56%	90.71%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.51%	95.50%
CHEMBL2179	P04062	Beta-glucocerebrosidase	81.05%	85.31%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.00%	95.89%

Plants that contains it

• Akebia trifoliata
• Prunus grayana

Cross-Links

• PubChem: 13845929
• LOTUS: LTS0153592
• wikiData: Q105299751