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

Details

• Internal ID: 86108c4a-9759-4902-bc3c-a77ae4070093
• 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-dihydroxy-5-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)OC)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)OC)O)OC)O)O)O
• InChI: InChI=1S/C33H40O19/c1-45-17-9-14(8-16(35)24(17)38)4-7-23(37)52-32-30(44)28(42)27(41)21(50-32)13-48-33-31(29(43)26(40)20(12-34)49-33)51-22(36)6-5-15-10-18(46-2)25(39)19(11-15)47-3/h4-11,20-21,26-35,38-44H,12-13H2,1-3H3/b6-5+,7-4+/t20-,21-,26-,27-,28+,29+,30-,31-,32+,33-/m1/s1
• InChI Key: GKSONHGXTXBVHW-MTOMAFSRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀O₁₉
• Molecular Weight: 740.70 g/mol
• Exact Mass: 740.21637904 g/mol
• Topological Polar Surface Area (TPSA): 290.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -1.73
• H-Bond Acceptor: 19
• H-Bond Donor: 9
• 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	-	0.8879	88.79%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.5365	53.65%
OATP2B1 inhibitior	-	0.5847	58.47%
OATP1B1 inhibitior	+	0.8197	81.97%
OATP1B3 inhibitior	+	0.9551	95.51%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.5526	55.26%
P-glycoprotein inhibitior	+	0.6404	64.04%
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	-	0.8546	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	+	0.6187	61.87%
CYP inhibitory promiscuity	-	0.8424	84.24%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6806	68.06%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9094	90.94%
Skin irritation	-	0.8705	87.05%
Skin corrosion	-	0.9584	95.84%
Ames mutagenesis	-	0.7178	71.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.6937	69.37%
Micronuclear	+	0.5033	50.33%
Hepatotoxicity	-	0.8216	82.16%
skin sensitisation	-	0.8711	87.11%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.9263	92.63%
Acute Oral Toxicity (c)	III	0.7158	71.58%
Estrogen receptor binding	+	0.7996	79.96%
Androgen receptor binding	-	0.5595	55.95%
Thyroid receptor binding	+	0.5446	54.46%
Glucocorticoid receptor binding	+	0.5854	58.54%
Aromatase binding	+	0.5914	59.14%
PPAR gamma	+	0.7021	70.21%
Honey bee toxicity	-	0.8242	82.42%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
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	99.66%	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: 24827679
• NPASS: NPC292129
• LOTUS: LTS0072196
• wikiData: Q105010251