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

Details

• Internal ID: 374ca9ca-9133-428a-948b-14041f02415e
• 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-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=CC(=CC(=C1O)O)C=CC(=O)OC2C(C(C(OC2OCC3C(C(C(C(O3)OC(=O)C=CC4=CC(=C(C(=C4)OC)O)O)O)O)O)CO)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)O)/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)OC)O)O)O)O)O)CO)O)O
• InChI: InChI=1S/C32H38O19/c1-45-17-9-13(7-15(34)23(17)38)3-5-21(36)50-30-28(43)25(40)19(11-33)48-32(30)47-12-20-26(41)27(42)29(44)31(49-20)51-22(37)6-4-14-8-16(35)24(39)18(10-14)46-2/h3-10,19-20,25-35,38-44H,11-12H2,1-2H3/b5-3+,6-4+/t19-,20-,25-,26-,27+,28+,29-,30-,31+,32-/m1/s1
• InChI Key: HHPKRDZARJAVJF-RQECULSDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₃₈O₁₉
• Molecular Weight: 726.60 g/mol
• Exact Mass: 726.20072898 g/mol
• Topological Polar Surface Area (TPSA): 301.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -2.03
• H-Bond Acceptor: 19
• H-Bond Donor: 10
• 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	-	0.8898	88.98%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.5495	54.95%
OATP2B1 inhibitior	-	0.5836	58.36%
OATP1B1 inhibitior	+	0.8197	81.97%
OATP1B3 inhibitior	+	0.9689	96.89%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	+	0.6409	64.09%
P-glycoprotein substrate	-	0.7329	73.29%
CYP3A4 substrate	+	0.5873	58.73%
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	+	0.6187	61.87%
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	-	0.9075	90.75%
Skin irritation	-	0.8658	86.58%
Skin corrosion	-	0.9538	95.38%
Ames mutagenesis	-	0.7178	71.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7404	74.04%
Micronuclear	+	0.5233	52.33%
Hepatotoxicity	-	0.8216	82.16%
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	-	0.9263	92.63%
Acute Oral Toxicity (c)	III	0.7336	73.36%
Estrogen receptor binding	+	0.7807	78.07%
Androgen receptor binding	-	0.5221	52.21%
Thyroid receptor binding	+	0.5440	54.40%
Glucocorticoid receptor binding	+	0.5431	54.31%
Aromatase binding	+	0.5909	59.09%
PPAR gamma	+	0.6983	69.83%
Honey bee toxicity	-	0.8242	82.42%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
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	99.66%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.60%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.85%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.46%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.49%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.48%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	92.44%	94.73%
CHEMBL3194	P02766	Transthyretin	91.33%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.56%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.05%	86.92%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.79%	97.36%
CHEMBL5255	O00206	Toll-like receptor 4	84.73%	92.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.62%	96.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.10%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.99%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.12%	95.89%
CHEMBL4581	P52732	Kinesin-like protein 1	80.68%	93.18%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.01%	92.62%

Plants that contains it

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

Cross-Links

• PubChem: 24827808
• NPASS: NPC310816
• LOTUS: LTS0119727
• wikiData: Q105028443