QUERCETIN 3-O-beta-D-GLUCURONIDE METHYL ESTER

Details

• Internal ID: 456f8dff-73ae-4190-9c1c-b2b8762ecc51
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glucuronides > Flavonoid-3-O-glucuronides
• IUPAC Name: methyl (2S,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylate
• SMILES (Canonical): COC(=O)C1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
• SMILES (Isomeric): COC(=O)[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
• InChI: InChI=1S/C22H20O13/c1-32-21(31)20-16(29)15(28)17(30)22(35-20)34-19-14(27)13-11(26)5-8(23)6-12(13)33-18(19)7-2-3-9(24)10(25)4-7/h2-6,15-17,20,22-26,28-30H,1H3/t15-,16-,17+,20-,22+/m0/s1
• InChI Key: DAKHAONGVOPWRO-NTKSAMNMSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₀O₁₃
• Molecular Weight: 492.40 g/mol
• Exact Mass: 492.09039069 g/mol
• Topological Polar Surface Area (TPSA): 213.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): -0.36
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

• NR6BBU6Z38
• Quercetin 3-(6-methylglucuronide)
• Quercetin 3-o-beta-D-glucuronide methyl ester
• 79543-28-5
• Methyl (2S,3S,4S,5R,6S)-6-((2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl)oxy)-3,4,5-trihydroxyoxane-2-carboxylate
• Quercetin 3-O-beta-D-glucuronide 6''-methyl ester
• beta-D-Glucopyranosiduronic acid, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl, methyl ester
• UNII-NR6BBU6Z38
• CHEMBL468872
• Quercetin 3-O-glucuronide methyl ester
• QUERCETIN 3-O-.BETA.-D-GLUCURONIDE METHYL ESTER
• QUERCETIN 3-O-.BETA.-D-GLUCURONIDE 6''-METHYL ESTER
• .BETA.-D-GLUCOPYRANOSIDURONIC ACID, 2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-4-OXO-4H-1-BENZOPYRAN-3-YL, METHYL ESTER

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7483	74.83%
Caco-2	-	0.8761	87.61%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6619	66.19%
OATP2B1 inhibitior	+	0.5907	59.07%
OATP1B1 inhibitior	+	0.9307	93.07%
OATP1B3 inhibitior	+	0.9857	98.57%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5433	54.33%
P-glycoprotein inhibitior	-	0.4419	44.19%
P-glycoprotein substrate	-	0.6533	65.33%
CYP3A4 substrate	+	0.6567	65.67%
CYP2C9 substrate	-	0.6438	64.38%
CYP2D6 substrate	-	0.8738	87.38%
CYP3A4 inhibition	-	0.7674	76.74%
CYP2C9 inhibition	-	0.8642	86.42%
CYP2C19 inhibition	-	0.8511	85.11%
CYP2D6 inhibition	-	0.9471	94.71%
CYP1A2 inhibition	-	0.6411	64.11%
CYP2C8 inhibition	+	0.9319	93.19%
CYP inhibitory promiscuity	-	0.7677	76.77%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5903	59.03%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.8629	86.29%
Skin irritation	-	0.6835	68.35%
Skin corrosion	-	0.9231	92.31%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	+	0.5718	57.18%
skin sensitisation	-	0.9291	92.91%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.6619	66.19%
Acute Oral Toxicity (c)	III	0.5786	57.86%
Estrogen receptor binding	+	0.7212	72.12%
Androgen receptor binding	+	0.7966	79.66%
Thyroid receptor binding	-	0.5102	51.02%
Glucocorticoid receptor binding	+	0.6433	64.33%
Aromatase binding	-	0.5871	58.71%
PPAR gamma	+	0.6066	60.66%
Honey bee toxicity	-	0.7728	77.28%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9235	92.35%

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	99.35%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.43%	89.00%
CHEMBL2581	P07339	Cathepsin D	95.44%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	93.60%	91.49%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	93.26%	95.64%
CHEMBL3401	O75469	Pregnane X receptor	92.46%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.43%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.81%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.58%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.44%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.00%	99.15%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.63%	90.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.67%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.38%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.58%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.56%	99.23%
CHEMBL4208	P20618	Proteasome component C5	82.40%	90.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.69%	93.65%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.98%	94.33%
CHEMBL3194	P02766	Transthyretin	80.38%	90.71%

Plants that contains it

• Artemisia afra
• Cosmos sulphureus
• Epipactis palustris
• Ophiopogon japonicus
• Periploca sepium
• Pimenta dioica
• Potentilla anserina
• Roemeria hispida
• Rumex obtusifolius
• Tanacetum argenteum
• Thamnosma rhodesica
• Theobroma grandiflorum

Cross-Links

• PubChem: 21722016
• NPASS: NPC175107
• ChEMBL: CHEMBL468872
• LOTUS: LTS0126234
• wikiData: Q104973648