Quercetin 3-gentiobioside

Details

• Internal ID: 4400ebba-6ff9-4e2e-964e-3500b3a1b6b0
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)COC5C(C(C(C(O5)CO)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)CO[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C27H30O17/c28-6-14-17(33)20(36)22(38)26(42-14)40-7-15-18(34)21(37)23(39)27(43-15)44-25-19(35)16-12(32)4-9(29)5-13(16)41-24(25)8-1-2-10(30)11(31)3-8/h1-5,14-15,17-18,20-23,26-34,36-39H,6-7H2/t14-,15-,17-,18-,20+,21+,22-,23-,26-,27+/m1/s1
• InChI Key: FDRQPMVGJOQVTL-DEFKTLOSSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₇
• Molecular Weight: 626.50 g/mol
• Exact Mass: 626.14829948 g/mol
• Topological Polar Surface Area (TPSA): 286.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -2.71
• H-Bond Acceptor: 17
• H-Bond Donor: 11
• Rotatable Bonds: 7

Synonyms

• 7431-83-6
• quercetin-3-gentiobioside
• 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• Quercetin 3-O-diglucoside
• Quercetin 3-O-gentiobioside
• quercetin 3-beta-gentiobioside
• CHEMBL1097317
• CHEBI:136778
• DTXSID701310649
• GLXC-14772
• HY-N4089
• MS-30825
• beta-D-glucosyl-(1->6)-beta-D-glucoside
• CS-0032092
• quercetin beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside
• 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
• 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one
• 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl 6-O-beta-D-glucopyranosyl-beta-D-glucopyranoside
• 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside
• 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl beta-D-glucosyl-(1->6)-beta-D-glucoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5736	57.36%
Caco-2	-	0.9284	92.84%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.5848	58.48%
OATP2B1 inhibitior	-	0.5578	55.78%
OATP1B1 inhibitior	+	0.9136	91.36%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5368	53.68%
P-glycoprotein inhibitior	-	0.5563	55.63%
P-glycoprotein substrate	-	0.6951	69.51%
CYP3A4 substrate	+	0.6360	63.60%
CYP2C9 substrate	-	0.6709	67.09%
CYP2D6 substrate	-	0.8582	85.82%
CYP3A4 inhibition	-	0.9390	93.90%
CYP2C9 inhibition	-	0.9315	93.15%
CYP2C19 inhibition	-	0.9047	90.47%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.9180	91.80%
CYP2C8 inhibition	+	0.8808	88.08%
CYP inhibitory promiscuity	-	0.7526	75.26%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6848	68.48%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8989	89.89%
Skin irritation	-	0.8255	82.55%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3629	36.29%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	+	0.5429	54.29%
skin sensitisation	-	0.9132	91.32%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.7635	76.35%
Acute Oral Toxicity (c)	IV	0.4763	47.63%
Estrogen receptor binding	+	0.8171	81.71%
Androgen receptor binding	+	0.6413	64.13%
Thyroid receptor binding	+	0.5486	54.86%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.6416	64.16%
PPAR gamma	+	0.7560	75.60%
Honey bee toxicity	-	0.7362	73.62%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6050	60.50%
Fish aquatic toxicity	+	0.7958	79.58%

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	99.63%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.65%	89.00%
CHEMBL2581	P07339	Cathepsin D	95.20%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.40%	99.15%
CHEMBL1951	P21397	Monoamine oxidase A	92.85%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.76%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	90.96%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.52%	86.33%
CHEMBL3194	P02766	Transthyretin	89.67%	90.71%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	89.34%	95.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.24%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.41%	86.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.02%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.20%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.37%	97.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.14%	95.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.78%	95.56%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	80.29%	80.78%

Plants that contains it

• Afrocarpus gracilior
• Agave xylonacantha
• Anthemis cretica
• Antiphiona pinnatisecta
• Calophyllum inophyllum
• Chenopodium album
• Dryopteris aitoniana
• Dysphania botrys
• Gossypium hirsutum
• Hedyosmum arborescens
• Lathyrus pratensis
• Lycopodium japonicum
• Maackia tashiroi
• Monoon cupulare
• Ochradenus baccatus
• Phyllanthus virgatus
• Primula spectabilis
• Prunus dulcis
• Psorospermum adamauense
• Ranunculus biternatus
• Rosa gallica
• Senegalia pennata
• Senna alexandrina
• Thelypteris esquirolii
• Tribulus terrestris
• Turnera diffusa
• Vachellia tortilis subsp. raddiana

Cross-Links

• PubChem: 5320834
• NPASS: NPC156869
• ChEMBL: CHEMBL1097317
• LOTUS: LTS0183115
• wikiData: Q104993730