2-[4-(beta-D-Glucopyranosyloxy)phenyl]-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: 6e0df34b-6064-4425-a56e-912a87d842fe
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-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-4-oxo-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-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)OC7C(C(C(C(O7)CO)O)O)O)OC(=O)C=CC8=CC(=C(C(=C8)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[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)OC(=O)/C=C/C8=CC(=C(C(=C8)OC)O)OC)O)O)O)CO)O)O
• InChI: InChI=1S/C55H60O28/c1-72-30-13-22(14-31(73-2)41(30)61)5-11-37(59)79-29-18-28-39(26(58)17-27(78-28)24-7-9-25(10-8-24)77-54-51(71)48(68)43(63)34(19-56)81-54)46(66)40(29)52-50(70)47(67)45(65)36(80-52)21-76-55-53(49(69)44(64)35(20-57)82-55)83-38(60)12-6-23-15-32(74-3)42(62)33(16-23)75-4/h5-18,34-36,43-45,47-57,61-71H,19-21H2,1-4H3/b11-5+,12-6+/t34-,35-,36-,43-,44-,45-,47+,48+,49+,50-,51-,52+,53-,54-,55-/m1/s1
• InChI Key: JQQUFQDXUKPOLZ-ABQZIVPASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₅H₆₀O₂₈
• Molecular Weight: 1169.00 g/mol
• Exact Mass: 1168.32711125 g/mol
• Topological Polar Surface Area (TPSA): 425.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): -0.99
• H-Bond Acceptor: 28
• H-Bond Donor: 13
• Rotatable Bonds: 19

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	-	0.8589	85.89%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.4963	49.63%
OATP2B1 inhibitior	-	0.7203	72.03%
OATP1B1 inhibitior	+	0.7781	77.81%
OATP1B3 inhibitior	+	0.9721	97.21%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8048	80.48%
P-glycoprotein inhibitior	+	0.7409	74.09%
P-glycoprotein substrate	+	0.6569	65.69%
CYP3A4 substrate	+	0.6980	69.80%
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	+	0.8360	83.60%
CYP inhibitory promiscuity	-	0.7831	78.31%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6541	65.41%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.8973	89.73%
Skin irritation	-	0.8479	84.79%
Skin corrosion	-	0.9548	95.48%
Ames mutagenesis	-	0.5901	59.01%
Human Ether-a-go-go-Related Gene inhibition	+	0.7638	76.38%
Micronuclear	+	0.6333	63.33%
Hepatotoxicity	-	0.8625	86.25%
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	-	0.9660	96.60%
Acute Oral Toxicity (c)	III	0.6211	62.11%
Estrogen receptor binding	+	0.7339	73.39%
Androgen receptor binding	+	0.7232	72.32%
Thyroid receptor binding	+	0.6037	60.37%
Glucocorticoid receptor binding	+	0.7122	71.22%
Aromatase binding	+	0.6253	62.53%
PPAR gamma	+	0.7834	78.34%
Honey bee toxicity	-	0.6341	63.41%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
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	99.79%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.18%	89.00%
CHEMBL2581	P07339	Cathepsin D	96.76%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.27%	96.00%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	95.77%	83.57%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.50%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.36%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	94.00%	86.92%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.39%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.39%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.81%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.98%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	88.80%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.47%	99.17%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.79%	96.21%
CHEMBL3194	P02766	Transthyretin	84.90%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.44%	94.45%
CHEMBL1907	P15144	Aminopeptidase N	82.46%	93.31%
CHEMBL5255	O00206	Toll-like receptor 4	82.08%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.42%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.50%	92.62%

Plants that contains it

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

Cross-Links

• PubChem: 11228635
• NPASS: NPC73288
• LOTUS: LTS0076529
• wikiData: Q105133615