2-(4-Hydroxyphenyl)-5-hydroxy-6-[6-O-[2-O-(3,5-dimethoxy-4-hydroxycinnamoyl)-beta-D-glucopyranosyl]-beta-D-glucopyranosyl]-7-(3,5-dimethoxy-4-hydroxycinnamoyloxy)-4H-1-benzopyran-4-one

Details

• Internal ID: 670e7d81-3330-45ac-a02e-aae22eaf1dda
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides
• IUPAC Name: [(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-7-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy-2-(4-hydroxyphenyl)-4-oxochromen-6-yl]oxan-2-yl]methoxy]oxan-3-yl] (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C=CC(=O)OC2C(C(C(OC2OCC3C(C(C(C(O3)C4=C(C=C5C(=C4O)C(=O)C=C(O5)C6=CC=C(C=C6)O)OC(=O)C=CC7=CC(=C(C(=C7)OC)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)C4=C(C=C5C(=C4O)C(=O)C=C(O5)C6=CC=C(C=C6)O)OC(=O)/C=C/C7=CC(=C(C(=C7)OC)O)OC)O)O)O)CO)O)O
• InChI: InChI=1S/C49H50O23/c1-63-29-13-21(14-30(64-2)39(29)55)5-11-35(53)69-28-18-27-37(25(52)17-26(68-27)23-7-9-24(51)10-8-23)43(59)38(28)47-46(62)44(60)42(58)34(70-47)20-67-49-48(45(61)41(57)33(19-50)71-49)72-36(54)12-6-22-15-31(65-3)40(56)32(16-22)66-4/h5-18,33-34,41-42,44-51,55-62H,19-20H2,1-4H3/b11-5+,12-6+/t33-,34-,41-,42-,44+,45+,46-,47+,48-,49-/m1/s1
• InChI Key: PCNQRAQGLJYIGH-UCQAEWAZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₉H₅₀O₂₃
• Molecular Weight: 1006.90 g/mol
• Exact Mass: 1006.27428784 g/mol
• Topological Polar Surface Area (TPSA): 346.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.54
• H-Bond Acceptor: 23
• H-Bond Donor: 10
• Rotatable Bonds: 16

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5284	52.84%
Caco-2	-	0.8659	86.59%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.4963	49.63%
OATP2B1 inhibitior	-	0.5750	57.50%
OATP1B1 inhibitior	+	0.7587	75.87%
OATP1B3 inhibitior	+	0.9721	97.21%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6905	69.05%
P-glycoprotein inhibitior	+	0.7380	73.80%
P-glycoprotein substrate	+	0.6548	65.48%
CYP3A4 substrate	+	0.6934	69.34%
CYP2C9 substrate	-	0.8152	81.52%
CYP2D6 substrate	-	0.8655	86.55%
CYP3A4 inhibition	-	0.9320	93.20%
CYP2C9 inhibition	-	0.8977	89.77%
CYP2C19 inhibition	-	0.9209	92.09%
CYP2D6 inhibition	-	0.9517	95.17%
CYP1A2 inhibition	-	0.9398	93.98%
CYP2C8 inhibition	+	0.8573	85.73%
CYP inhibitory promiscuity	-	0.7831	78.31%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6541	65.41%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.8999	89.99%
Skin irritation	-	0.8479	84.79%
Skin corrosion	-	0.9548	95.48%
Ames mutagenesis	-	0.6001	60.01%
Human Ether-a-go-go-Related Gene inhibition	+	0.7043	70.43%
Micronuclear	+	0.6333	63.33%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.8995	89.95%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.9570	95.70%
Acute Oral Toxicity (c)	III	0.6211	62.11%
Estrogen receptor binding	+	0.7464	74.64%
Androgen receptor binding	+	0.7296	72.96%
Thyroid receptor binding	+	0.5712	57.12%
Glucocorticoid receptor binding	+	0.6566	65.66%
Aromatase binding	+	0.6300	63.00%
PPAR gamma	+	0.7449	74.49%
Honey bee toxicity	-	0.6303	63.03%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9012	90.12%

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	99.67%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.30%	89.00%
CHEMBL2581	P07339	Cathepsin D	97.52%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.80%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.67%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.06%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.04%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.90%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.59%	96.09%
CHEMBL3194	P02766	Transthyretin	91.55%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.29%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	89.17%	94.73%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.96%	96.21%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.66%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.09%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.39%	99.17%
CHEMBL5255	O00206	Toll-like receptor 4	85.15%	92.50%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.60%	91.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.58%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.12%	97.14%

Plants that contains it

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

Cross-Links

• PubChem: 11787982
• NPASS: NPC165114
• LOTUS: LTS0010194
• wikiData: Q105205897