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

Details

• Internal ID: 0d513e62-fa06-4621-b469-0c7d92507e5a
• 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-(3,4-dihydroxyphenyl)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)O)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)O)O)O)O)CO)O)O
• InChI: InChI=1S/C32H38O18/c1-44-18-10-15(11-19(45-2)24(18)38)5-8-22(36)49-30-28(42)25(39)20(12-33)47-32(30)46-13-21-26(40)27(41)29(43)31(48-21)50-23(37)7-4-14-3-6-16(34)17(35)9-14/h3-11,20-21,25-35,38-43H,12-13H2,1-2H3/b7-4+,8-5+/t20-,21-,25-,26-,27+,28+,29-,30-,31+,32-/m1/s1
• InChI Key: FUETYOGYMBALQW-ORCPWHRNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₃₈O₁₈
• Molecular Weight: 710.60 g/mol
• Exact Mass: 710.20581436 g/mol
• Topological Polar Surface Area (TPSA): 281.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -1.73
• H-Bond Acceptor: 18
• H-Bond Donor: 9
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8077	80.77%
Caco-2	-	0.8914	89.14%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.5495	54.95%
OATP2B1 inhibitior	-	0.7207	72.07%
OATP1B1 inhibitior	+	0.8636	86.36%
OATP1B3 inhibitior	+	0.9689	96.89%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.4856	48.56%
P-glycoprotein inhibitior	+	0.6233	62.33%
P-glycoprotein substrate	-	0.7153	71.53%
CYP3A4 substrate	+	0.6119	61.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8577	85.77%
CYP3A4 inhibition	-	0.8476	84.76%
CYP2C9 inhibition	-	0.8781	87.81%
CYP2C19 inhibition	-	0.8885	88.85%
CYP2D6 inhibition	-	0.9241	92.41%
CYP1A2 inhibition	-	0.9361	93.61%
CYP2C8 inhibition	+	0.6992	69.92%
CYP inhibitory promiscuity	-	0.8248	82.48%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7132	71.32%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9132	91.32%
Skin irritation	-	0.8658	86.58%
Skin corrosion	-	0.9538	95.38%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6662	66.62%
Micronuclear	+	0.5233	52.33%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.8581	85.81%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.9531	95.31%
Acute Oral Toxicity (c)	III	0.7336	73.36%
Estrogen receptor binding	+	0.8079	80.79%
Androgen receptor binding	-	0.5274	52.74%
Thyroid receptor binding	+	0.5311	53.11%
Glucocorticoid receptor binding	+	0.5867	58.67%
Aromatase binding	+	0.5766	57.66%
PPAR gamma	+	0.7045	70.45%
Honey bee toxicity	-	0.7854	78.54%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6255	62.55%
Fish aquatic toxicity	+	0.8562	85.62%

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	99.77%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.68%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.24%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.07%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.82%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.90%	95.56%
CHEMBL3194	P02766	Transthyretin	93.29%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	91.22%	94.73%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	89.50%	80.78%
CHEMBL1951	P21397	Monoamine oxidase A	88.52%	91.49%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.75%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.98%	94.45%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.01%	89.62%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.26%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.70%	97.09%
CHEMBL2581	P07339	Cathepsin D	81.40%	98.95%
CHEMBL4208	P20618	Proteasome component C5	81.21%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.82%	97.36%

Plants that contains it

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

Cross-Links

• PubChem: 24827807
• NPASS: NPC806
• LOTUS: LTS0207036
• wikiData: Q105001655