[(2S,3S,4R,5R)-2-[(2R,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-4-hydroxy-2,5-bis[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxolan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: 6a9f9bd8-b6df-4306-8c5f-b6e6fcf20171
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: [(2S,3S,4R,5R)-2-[(2R,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-4-hydroxy-2,5-bis[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxolan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC2(C(C(C(O2)COC(=O)C=CC3=CC(=C(C=C3)O)OC)O)OC(=O)C=CC4=CC=C(C=C4)O)COC(=O)C=CC5=CC(=C(C=C5)O)OC)O)O)O
• SMILES (Isomeric): CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)COC(=O)/C=C/C3=CC(=C(C=C3)O)OC)O)OC(=O)/C=C/C4=CC=C(C=C4)O)COC(=O)/C=C/C5=CC(=C(C=C5)O)OC)O)O)O
• InChI: InChI=1S/C43H46O20/c1-23(44)57-20-32-37(51)39(53)40(54)42(60-32)63-43(22-59-35(49)16-10-26-7-14-29(47)31(19-26)56-3)41(61-36(50)17-8-24-4-11-27(45)12-5-24)38(52)33(62-43)21-58-34(48)15-9-25-6-13-28(46)30(18-25)55-2/h4-19,32-33,37-42,45-47,51-54H,20-22H2,1-3H3/b15-9+,16-10+,17-8+/t32-,33-,37-,38-,39+,40-,41+,42-,43+/m1/s1
• InChI Key: YHQFVWGSNAWSJL-WWEJWWLMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₄₆O₂₀
• Molecular Weight: 882.80 g/mol
• Exact Mass: 882.25824385 g/mol
• Topological Polar Surface Area (TPSA): 293.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.10
• H-Bond Acceptor: 20
• H-Bond Donor: 7
• Rotatable Bonds: 17

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6261	62.61%
Caco-2	-	0.8773	87.73%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7254	72.54%
OATP2B1 inhibitior	-	0.5803	58.03%
OATP1B1 inhibitior	+	0.8556	85.56%
OATP1B3 inhibitior	+	0.9258	92.58%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9081	90.81%
P-glycoprotein inhibitior	+	0.7568	75.68%
P-glycoprotein substrate	-	0.5874	58.74%
CYP3A4 substrate	+	0.6750	67.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8707	87.07%
CYP3A4 inhibition	-	0.8689	86.89%
CYP2C9 inhibition	-	0.8237	82.37%
CYP2C19 inhibition	-	0.8268	82.68%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.8530	85.30%
CYP2C8 inhibition	+	0.8500	85.00%
CYP inhibitory promiscuity	-	0.7648	76.48%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6643	66.43%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9104	91.04%
Skin irritation	-	0.8400	84.00%
Skin corrosion	-	0.9507	95.07%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7681	76.81%
Micronuclear	-	0.5152	51.52%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8290	82.90%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.8701	87.01%
Acute Oral Toxicity (c)	III	0.6015	60.15%
Estrogen receptor binding	+	0.8390	83.90%
Androgen receptor binding	+	0.7166	71.66%
Thyroid receptor binding	+	0.6017	60.17%
Glucocorticoid receptor binding	+	0.6872	68.72%
Aromatase binding	+	0.5511	55.11%
PPAR gamma	+	0.7416	74.16%
Honey bee toxicity	-	0.6894	68.94%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9807	98.07%

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	99.65%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.24%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.69%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.17%	96.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.43%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.00%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	92.80%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.99%	95.56%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	91.62%	89.62%
CHEMBL3194	P02766	Transthyretin	91.11%	90.71%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.63%	95.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.58%	99.17%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	88.54%	97.21%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.26%	94.45%
CHEMBL4208	P20618	Proteasome component C5	86.68%	90.00%
CHEMBL1951	P21397	Monoamine oxidase A	84.72%	91.49%
CHEMBL340	P08684	Cytochrome P450 3A4	84.63%	91.19%
CHEMBL2535	P11166	Glucose transporter	84.19%	98.75%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.45%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.33%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.89%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.76%	97.36%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	81.22%	100.00%

Plants that contains it

• Ageratina adenophora
• Boehmeria nivea
• Crotalaria micans
• Croton poilanei
• Dasymaschalon sootepense
• Dictyoloma vandellianum
• Euonymus sachalinensis
• Felicia erigeroides
• Flueggea virosa subsp. melanthesoides
• Guatteria megalophylla
• Lupinus paniculatus
• Lycoris traubii
• Lygodium flexuosum
• Panax ginseng
• Saccharum spontaneum
• Smilax bracteata
• Strychnos staudtii
• Tsuga mertensiana

Cross-Links

• PubChem: 11593148
• NPASS: NPC98185
• LOTUS: LTS0220362
• wikiData: Q105348556