Quercetin 3-(2G-xylosylrutinoside)

Details

• Internal ID: 4943fe35-0093-4914-bf51-d6b947b7d1e3
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)OC6C(C(C(CO6)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O[C@H]6[C@@H]([C@H]([C@@H](CO6)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C32H38O20/c1-9-19(38)23(42)26(45)30(48-9)47-8-17-21(40)24(43)29(52-31-25(44)20(39)15(37)7-46-31)32(50-17)51-28-22(41)18-14(36)5-11(33)6-16(18)49-27(28)10-2-3-12(34)13(35)4-10/h2-6,9,15,17,19-21,23-26,29-40,42-45H,7-8H2,1H3/t9-,15+,17+,19-,20-,21+,23+,24-,25+,26+,29+,30+,31-,32-/m0/s1
• InChI Key: RLTNQOUWXZXZCS-VMMUDTPISA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₃₈O₂₀
• Molecular Weight: 742.60 g/mol
• Exact Mass: 742.19564360 g/mol
• Topological Polar Surface Area (TPSA): 324.00 Ų
• XlogP: -2.80
• Atomic LogP (AlogP): -3.22
• H-Bond Acceptor: 20
• H-Bond Donor: 12
• Rotatable Bonds: 8

Synonyms

• Quercetin 3-(2G-xylosylrutinoside)
• 129235-39-8
• C10175
• Quercetin 3-O-beta-(2(G)-O-beta-xylopyranosyl-6(G)-O-alpha-rhamnopyranosyl)glucopyranoside
• AC1NQYWG
• 2-(3,4-dihydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxychromen-4-one
• CHEMBL4090909
• DTXSID80926350
• CPD-5781
• quercetin 3-O-{beta-L-rhamnosyl-(1->6)]-beta-D-glucoside}
• 2-(3,4-dihydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]-3-[(2S,3R,4S,5R)-3,4,5-trihydroxytetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-5,7-dihydroxy-chromen-4-one
• 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl 6-deoxyhexopyranosyl-(1->6)-[pentopyranosyl-(1->2)]hexopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5635	56.35%
Caco-2	-	0.9181	91.81%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6570	65.70%
OATP2B1 inhibitior	-	0.7125	71.25%
OATP1B1 inhibitior	+	0.8986	89.86%
OATP1B3 inhibitior	+	0.9190	91.90%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7029	70.29%
P-glycoprotein inhibitior	-	0.5466	54.66%
P-glycoprotein substrate	+	0.6565	65.65%
CYP3A4 substrate	+	0.6915	69.15%
CYP2C9 substrate	-	0.7038	70.38%
CYP2D6 substrate	-	0.8611	86.11%
CYP3A4 inhibition	-	0.9513	95.13%
CYP2C9 inhibition	-	0.9536	95.36%
CYP2C19 inhibition	-	0.9338	93.38%
CYP2D6 inhibition	-	0.9439	94.39%
CYP1A2 inhibition	-	0.9091	90.91%
CYP2C8 inhibition	+	0.8349	83.49%
CYP inhibitory promiscuity	-	0.8349	83.49%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6383	63.83%
Eye corrosion	-	0.9934	99.34%
Eye irritation	-	0.9119	91.19%
Skin irritation	-	0.8252	82.52%
Skin corrosion	-	0.9585	95.85%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7435	74.35%
Micronuclear	+	0.6933	69.33%
Hepatotoxicity	+	0.5826	58.26%
skin sensitisation	-	0.9218	92.18%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.9749	97.49%
Acute Oral Toxicity (c)	III	0.6372	63.72%
Estrogen receptor binding	+	0.8255	82.55%
Androgen receptor binding	+	0.6074	60.74%
Thyroid receptor binding	+	0.5310	53.10%
Glucocorticoid receptor binding	+	0.5410	54.10%
Aromatase binding	+	0.5934	59.34%
PPAR gamma	+	0.7244	72.44%
Honey bee toxicity	-	0.7119	71.19%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5350	53.50%
Fish aquatic toxicity	+	0.8359	83.59%

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	99.82%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.76%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.20%	89.00%
CHEMBL2581	P07339	Cathepsin D	97.91%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.63%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.74%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.27%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	92.36%	94.73%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	90.90%	95.64%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.89%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.57%	95.56%
CHEMBL4208	P20618	Proteasome component C5	86.79%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.68%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.78%	97.36%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	85.72%	80.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.49%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.75%	90.71%
CHEMBL226	P30542	Adenosine A1 receptor	83.25%	95.93%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.05%	95.78%
CHEMBL1937	Q92769	Histone deacetylase 2	81.88%	94.75%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.35%	80.78%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.86%	99.23%

Plants that contains it

• Acmella ciliata
• Actinidia arguta
• Delphinium grandiflorum var. fangshanense
• Harungana madagascariensis
• Orixa japonica
• Phaseolus vulgaris
• Sesamoides interrupta
• Uncaria tomentosa
• Vasconcellea pubescens

Cross-Links

• PubChem: 5281690
• NPASS: NPC168871
• LOTUS: LTS0232267
• wikiData: Q82900862