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

Details

• Internal ID: a5ae00d2-075e-40bb-896b-fb944d88a3ff
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2S,3S,4R,5R)-4-hydroxy-3-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C=CC(=O)OC2C(C(OC2(CO)OC3C(C(C(C(O3)COC(=O)C=CC4=CC(=C(C=C4)O)OC)O)O)O)CO)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)/C=C/C(=O)O[C@H]2[C@@H]([C@H](O[C@@]2(CO)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COC(=O)/C=C/C4=CC(=C(C=C4)O)OC)O)O)O)CO)O
• InChI: InChI=1S/C33H40O18/c1-44-19-10-16(4-7-18(19)36)5-8-24(37)47-14-23-27(40)29(42)30(43)32(48-23)51-33(15-35)31(28(41)22(13-34)50-33)49-25(38)9-6-17-11-20(45-2)26(39)21(12-17)46-3/h4-12,22-23,27-32,34-36,39-43H,13-15H2,1-3H3/b8-5+,9-6+/t22-,23-,27-,28-,29+,30-,31+,32-,33+/m1/s1
• InChI Key: WERMVJDMIWCEOV-PIEWPOMKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀O₁₈
• Molecular Weight: 724.70 g/mol
• Exact Mass: 724.22146442 g/mol
• Topological Polar Surface Area (TPSA): 270.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -1.43
• H-Bond Acceptor: 18
• H-Bond Donor: 8
• Rotatable Bonds: 14

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	-	0.8859	88.59%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7023	70.23%
OATP2B1 inhibitior	-	0.7227	72.27%
OATP1B1 inhibitior	+	0.8471	84.71%
OATP1B3 inhibitior	+	0.9459	94.59%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8778	87.78%
P-glycoprotein inhibitior	+	0.6790	67.90%
P-glycoprotein substrate	-	0.6217	62.17%
CYP3A4 substrate	+	0.6568	65.68%
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	+	0.7718	77.18%
CYP inhibitory promiscuity	-	0.7421	74.21%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6433	64.33%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9164	91.64%
Skin irritation	-	0.8527	85.27%
Skin corrosion	-	0.9546	95.46%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7131	71.31%
Micronuclear	-	0.5426	54.26%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8251	82.51%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.9403	94.03%
Acute Oral Toxicity (c)	III	0.6316	63.16%
Estrogen receptor binding	+	0.8393	83.93%
Androgen receptor binding	+	0.6204	62.04%
Thyroid receptor binding	+	0.5569	55.69%
Glucocorticoid receptor binding	+	0.6509	65.09%
Aromatase binding	+	0.5818	58.18%
PPAR gamma	+	0.7377	73.77%
Honey bee toxicity	-	0.7244	72.44%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
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	99.69%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	98.26%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.58%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.84%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.69%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.17%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.90%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	92.01%	94.73%
CHEMBL3194	P02766	Transthyretin	91.13%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.00%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	87.20%	91.49%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.08%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.88%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.56%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.90%	92.94%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.53%	89.62%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.20%	95.83%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.26%	94.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.09%	86.92%
CHEMBL340	P08684	Cytochrome P450 3A4	80.47%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.46%	92.62%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.41%	96.90%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.26%	97.36%

Plants that contains it

• Polygala wattersii
• Ruta graveolens

Cross-Links

• PubChem: 11115260
• LOTUS: LTS0232648
• wikiData: Q105303417