Quercetin 3-O-(6''-galloyl)-beta-D-glucopyranoside

Details

• Internal ID: b0164a10-f923-4031-852d-0ce671c67718
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate
• SMILES (Canonical): C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)COC(=O)C5=CC(=C(C(=C5)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)COC(=O)C5=CC(=C(C(=C5)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C28H24O16/c29-11-6-14(32)19-17(7-11)42-25(9-1-2-12(30)13(31)3-9)26(22(19)37)44-28-24(39)23(38)21(36)18(43-28)8-41-27(40)10-4-15(33)20(35)16(34)5-10/h1-7,18,21,23-24,28-36,38-39H,8H2/t18-,21-,23+,24-,28+/m1/s1
• InChI Key: FMQQLXJREAGPHS-OAYLZIFXSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₄O₁₆
• Molecular Weight: 616.50 g/mol
• Exact Mass: 616.10643467 g/mol
• Topological Polar Surface Area (TPSA): 273.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 0.44
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 6

Synonyms

• Quercetin 3-O-(6''-galloyl)-beta-D-glucopyranoside
• Quercetin 3-O-(6''-O-galloyl)-|A-D-glucoside
• ((2R,3S,4S,5R,6S)-6-((2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl 3,4,5-trihydroxybenzoate
• Tellimoside
• CHEMBL499432
• HY-N7989
• AKOS040760658
• CS-0138931
• Quercetin 3-O-(6''-O-galloyl)-??-D-glucoside
• Quercetin 3-O-(6''-O-galloyl)-beta-D-glucoside
• [(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6055	60.55%
Caco-2	-	0.9077	90.77%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6349	63.49%
OATP2B1 inhibitior	-	0.5506	55.06%
OATP1B1 inhibitior	+	0.8089	80.89%
OATP1B3 inhibitior	+	0.9474	94.74%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.5720	57.20%
P-glycoprotein inhibitior	+	0.6434	64.34%
P-glycoprotein substrate	-	0.6358	63.58%
CYP3A4 substrate	+	0.6642	66.42%
CYP2C9 substrate	-	0.6458	64.58%
CYP2D6 substrate	-	0.8669	86.69%
CYP3A4 inhibition	-	0.9135	91.35%
CYP2C9 inhibition	-	0.8848	88.48%
CYP2C19 inhibition	-	0.9087	90.87%
CYP2D6 inhibition	-	0.9593	95.93%
CYP1A2 inhibition	-	0.9330	93.30%
CYP2C8 inhibition	+	0.9374	93.74%
CYP inhibitory promiscuity	-	0.8642	86.42%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6994	69.94%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.8665	86.65%
Skin irritation	-	0.8191	81.91%
Skin corrosion	-	0.9613	96.13%
Ames mutagenesis	+	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3975	39.75%
Micronuclear	+	0.7292	72.92%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.9218	92.18%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.9683	96.83%
Acute Oral Toxicity (c)	III	0.4217	42.17%
Estrogen receptor binding	+	0.7358	73.58%
Androgen receptor binding	+	0.7780	77.80%
Thyroid receptor binding	-	0.5194	51.94%
Glucocorticoid receptor binding	+	0.6182	61.82%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6645	66.45%
Honey bee toxicity	-	0.7906	79.06%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6050	60.50%
Fish aquatic toxicity	+	0.9242	92.42%

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	99.65%	91.11%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	98.82%	95.64%
CHEMBL1951	P21397	Monoamine oxidase A	97.69%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.80%	89.00%
CHEMBL3194	P02766	Transthyretin	95.48%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.70%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.19%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.96%	99.17%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	92.80%	83.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	92.12%	95.17%
CHEMBL2581	P07339	Cathepsin D	91.10%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	90.83%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.45%	99.15%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	87.23%	95.78%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.07%	90.71%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	84.64%	94.42%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.50%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.98%	94.45%
CHEMBL220	P22303	Acetylcholinesterase	83.36%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.35%	97.09%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	83.01%	80.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.68%	99.23%
CHEMBL4208	P20618	Proteasome component C5	81.54%	90.00%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	80.79%	80.78%
CHEMBL1900	P15121	Aldose reductase	80.35%	92.38%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.25%	94.33%

Plants that contains it

• Actiniopteris radiata
• Aglaia laxiflora
• Artemisia carvifolia
• Callicarpa maingayi
• Cephalaria uralensis
• Crotalaria aegyptiaca
• Dicoma capensis
• Digitalis isabelliana
• Ericameria parryi
• Eugenia selloi
• Euphorbia turczaninowii
• Excoecaria agallocha
• Geranium sylvaticum
• Geranium tuberosum
• Haplophyllum ferganicum
• Melastoma malabathricum
• Pemphis acidula
• Quercus ilex
• Quercus laurifolia
• Sclerocarya birrea
• Scopolia carniolica
• Sonchus ortunoi
• Styrax ferrugineus
• Triplaris cumingiana
• Vincetoxicum hirundinaria

Cross-Links

• PubChem: 9830456
• NPASS: NPC37668
• LOTUS: LTS0122425
• wikiData: Q104997981