[(2R,3S,4S,5R,6R)-3,4-dihydroxy-6-[(2S,3S,4R,5R)-4-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy-2,5-bis(hydroxymethyl)-3-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxyoxolan-2-yl]oxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

Details

• Internal ID: 8e6b3d28-663a-4a5b-b717-4173eb45a677
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3S,4S,5R,6R)-3,4-dihydroxy-6-[(2S,3S,4R,5R)-4-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy-2,5-bis(hydroxymethyl)-3-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxyoxolan-2-yl]oxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C=CC(=O)OCC2C(C(C(C(O2)OC3(C(C(C(O3)CO)OC(=O)C=CC4=CC(=C(C(=C4)OC)O)OC)OC(=O)C=CC5=CC(=C(C(=C5)OC)OC)OC)CO)OC6C(C(C(C(O6)CO)O)O)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](O2)O[C@]3([C@H]([C@@H]([C@H](O3)CO)OC(=O)/C=C/C4=CC(=C(C(=C4)OC)O)OC)OC(=O)/C=C/C5=CC(=C(C(=C5)OC)OC)OC)CO)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)O
• InChI: InChI=1S/C52H64O28/c1-66-27-14-24(15-28(67-2)39(27)59)8-11-36(56)73-22-35-42(62)44(64)48(78-50-45(65)43(63)41(61)33(20-53)74-50)51(75-35)80-52(23-55)49(77-38(58)13-10-26-18-31(70-5)46(72-7)32(19-26)71-6)47(34(21-54)79-52)76-37(57)12-9-25-16-29(68-3)40(60)30(17-25)69-4/h8-19,33-35,41-45,47-51,53-55,59-65H,20-23H2,1-7H3/b11-8+,12-9+,13-10+/t33-,34-,35-,41-,42-,43+,44+,45-,47-,48-,49+,50+,51-,52+/m1/s1
• InChI Key: VIHUUPZJXFEYBP-OMSLKRBVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₂H₆₄O₂₈
• Molecular Weight: 1137.00 g/mol
• Exact Mass: 1136.35841138 g/mol
• Topological Polar Surface Area (TPSA): 392.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -1.31
• H-Bond Acceptor: 28
• H-Bond Donor: 10
• Rotatable Bonds: 24

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7827	78.27%
Caco-2	-	0.8633	86.33%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7023	70.23%
OATP2B1 inhibitior	-	0.8637	86.37%
OATP1B1 inhibitior	+	0.8167	81.67%
OATP1B3 inhibitior	+	0.9459	94.59%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8199	81.99%
P-glycoprotein inhibitior	+	0.7481	74.81%
P-glycoprotein substrate	-	0.5714	57.14%
CYP3A4 substrate	+	0.6942	69.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8593	85.93%
CYP3A4 inhibition	-	0.7802	78.02%
CYP2C9 inhibition	-	0.8269	82.69%
CYP2C19 inhibition	-	0.8158	81.58%
CYP2D6 inhibition	-	0.9296	92.96%
CYP1A2 inhibition	-	0.8796	87.96%
CYP2C8 inhibition	+	0.8058	80.58%
CYP inhibitory promiscuity	-	0.7421	74.21%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6433	64.33%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.8998	89.98%
Skin irritation	-	0.8527	85.27%
Skin corrosion	-	0.9546	95.46%
Ames mutagenesis	-	0.6678	66.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7403	74.03%
Micronuclear	-	0.5426	54.26%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.8251	82.51%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.9127	91.27%
Acute Oral Toxicity (c)	III	0.6316	63.16%
Estrogen receptor binding	+	0.7803	78.03%
Androgen receptor binding	+	0.6548	65.48%
Thyroid receptor binding	+	0.6257	62.57%
Glucocorticoid receptor binding	+	0.7095	70.95%
Aromatase binding	+	0.6468	64.68%
PPAR gamma	+	0.7659	76.59%
Honey bee toxicity	-	0.6438	64.38%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9374	93.74%

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	99.49%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.44%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.45%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.26%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.31%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.16%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	92.00%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.31%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	88.23%	92.50%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.01%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.21%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.39%	94.45%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.35%	96.90%
CHEMBL3194	P02766	Transthyretin	83.77%	90.71%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.69%	94.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.42%	86.92%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.16%	92.62%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.66%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.51%	97.09%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	80.63%	92.68%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.61%	94.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.31%	91.19%

Plants that contains it

• Polygala karensium

Cross-Links

• PubChem: 11332262
• LOTUS: LTS0029889
• wikiData: Q105286838