(E)-3,4-Dihydroxy-5-methoxycinnamoyl 6-O-[2-O-[(E)-3-methoxy-4-hydroxycinnamoyl]-beta-D-glucopyranosyl]-beta-D-glucopyranoside

Details

• Internal ID: 9f1537b1-4f5d-4b88-a206-c8f782332782
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Hydroxycinnamic acid glycosides
• IUPAC Name: [(2R,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6S)-6-[(E)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoyl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=CC(=CC(=C1O)O)C=CC(=O)OC2C(C(C(C(O2)COC3C(C(C(C(O3)CO)O)O)OC(=O)C=CC4=CC(=C(C=C4)O)OC)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)O)/C=C/C(=O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)OC(=O)/C=C/C4=CC(=C(C=C4)O)OC)O)O)O
• InChI: InChI=1S/C32H38O18/c1-44-18-10-14(3-6-16(18)34)4-7-22(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)8-5-15-9-17(35)24(38)19(11-15)45-2/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: SEVJYMQXYBHPLE-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	-	0.8934	89.34%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.5495	54.95%
OATP2B1 inhibitior	-	0.7205	72.05%
OATP1B1 inhibitior	+	0.8441	84.41%
OATP1B3 inhibitior	+	0.9689	96.89%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.4582	45.82%
P-glycoprotein inhibitior	+	0.6128	61.28%
P-glycoprotein substrate	-	0.7052	70.52%
CYP3A4 substrate	+	0.6088	60.88%
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	+	0.7359	73.59%
CYP inhibitory promiscuity	-	0.8248	82.48%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7132	71.32%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9139	91.39%
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	+	0.7120	71.20%
Micronuclear	+	0.5233	52.33%
Hepatotoxicity	-	0.8091	80.91%
skin sensitisation	-	0.8581	85.81%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.9514	95.14%
Acute Oral Toxicity (c)	III	0.7336	73.36%
Estrogen receptor binding	+	0.8069	80.69%
Androgen receptor binding	-	0.5294	52.94%
Thyroid receptor binding	+	0.5601	56.01%
Glucocorticoid receptor binding	+	0.5720	57.20%
Aromatase binding	+	0.5750	57.50%
PPAR gamma	+	0.6996	69.96%
Honey bee toxicity	-	0.8247	82.47%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
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	99.81%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	98.04%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.44%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.62%	86.33%
CHEMBL3194	P02766	Transthyretin	94.48%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.43%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.93%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	92.26%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.99%	99.17%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.00%	89.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.40%	94.45%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	85.89%	80.78%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.08%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.46%	97.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.94%	86.92%
CHEMBL4208	P20618	Proteasome component C5	80.44%	90.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.22%	92.62%

Plants that contains it

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

Cross-Links

• PubChem: 24827937
• NPASS: NPC111089
• LOTUS: LTS0264907
• wikiData: Q105251551