(E)-3-Methoxy-4-hydroxycinnamoyl 6-O-[2-O-[(E)-3,5-dimethoxy-4-hydroxycinnamoyl]-beta-D-glucopyranosyl]-beta-D-glucopyranoside

Details

• Internal ID: 3c33a376-8213-4d4d-af7f-79a43549b5a3
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Hydroxycinnamic acid glycosides
• IUPAC Name: [(2S,3R,4S,5S,6R)-6-[[(2R,3R,4S,5S,6R)-4,5-dihydroxy-3-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C=CC(=O)OC2C(C(C(OC2OCC3C(C(C(C(O3)OC(=O)C=CC4=CC(=C(C=C4)O)OC)O)O)O)CO)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)/C=C/C(=O)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC[C@@H]3[C@H]([C@@H]([C@H]([C@@H](O3)OC(=O)/C=C/C4=CC(=C(C=C4)O)OC)O)O)O)CO)O)O
• InChI: InChI=1S/C33H40O18/c1-44-18-10-15(4-7-17(18)35)5-8-24(37)51-32-30(43)28(41)27(40)22(49-32)14-47-33-31(29(42)26(39)21(13-34)48-33)50-23(36)9-6-16-11-19(45-2)25(38)20(12-16)46-3/h4-12,21-22,26-35,38-43H,13-14H2,1-3H3/b8-5+,9-6+/t21-,22-,26-,27-,28+,29+,30-,31-,32+,33-/m1/s1
• InChI Key: WYDJOXFUJHZWDE-QMLZWPFGSA-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: -0.20
• Atomic LogP (AlogP): -1.43
• H-Bond Acceptor: 18
• H-Bond Donor: 8
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7974	79.74%
Caco-2	-	0.8885	88.85%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.5365	53.65%
OATP2B1 inhibitior	-	0.5840	58.40%
OATP1B1 inhibitior	+	0.8500	85.00%
OATP1B3 inhibitior	+	0.9551	95.51%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.5286	52.86%
P-glycoprotein inhibitior	+	0.6329	63.29%
P-glycoprotein substrate	-	0.7367	73.67%
CYP3A4 substrate	+	0.6021	60.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8583	85.83%
CYP3A4 inhibition	-	0.8546	85.46%
CYP2C9 inhibition	-	0.8867	88.67%
CYP2C19 inhibition	-	0.9090	90.90%
CYP2D6 inhibition	-	0.9222	92.22%
CYP1A2 inhibition	-	0.9369	93.69%
CYP2C8 inhibition	+	0.7035	70.35%
CYP inhibitory promiscuity	-	0.8424	84.24%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6806	68.06%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9152	91.52%
Skin irritation	-	0.8705	87.05%
Skin corrosion	-	0.9584	95.84%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6890	68.90%
Micronuclear	+	0.5033	50.33%
Hepatotoxicity	-	0.8341	83.41%
skin sensitisation	-	0.8711	87.11%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.9543	95.43%
Acute Oral Toxicity (c)	III	0.7158	71.58%
Estrogen receptor binding	+	0.8135	81.35%
Androgen receptor binding	-	0.5378	53.78%
Thyroid receptor binding	+	0.5581	55.81%
Glucocorticoid receptor binding	+	0.5868	58.68%
Aromatase binding	+	0.5482	54.82%
PPAR gamma	+	0.6933	69.33%
Honey bee toxicity	-	0.8141	81.41%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6455	64.55%
Fish aquatic toxicity	+	0.8602	86.02%

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	99.70%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.79%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.30%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.35%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.49%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.23%	95.56%
CHEMBL3194	P02766	Transthyretin	93.05%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	91.22%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.10%	99.17%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.42%	89.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.92%	94.45%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	85.12%	80.78%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.94%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.84%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.06%	97.36%
CHEMBL4208	P20618	Proteasome component C5	80.31%	90.00%

Plants that contains it

• Chrysosplenium americanum
• Eriocapitella tomentosa
• Eritrichium sericeum
• Olea europaea
• Phlogacanthus tubiflorus
• Sabia japonica
• Woodsia manchuriensis

Cross-Links

• PubChem: 24827806
• NPASS: NPC248996
• LOTUS: LTS0213946
• wikiData: Q105322081