[(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-chromen-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl] 3,4,5-trihydroxybenzoate

Details

• Internal ID: e539ca3d-168f-4ae9-ac2e-820f41b8b4d4
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: [(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 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)CO)O)O)OC(=O)C5=CC(=C(C(=C5)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)O)O)OC(=O)C5=CC(=C(C(=C5)O)O)O)O)O
• InChI: InChI=1S/C28H24O16/c29-8-18-21(37)23(39)26(43-27(40)10-4-15(34)20(36)16(35)5-10)28(42-18)44-25-22(38)19-14(33)6-11(30)7-17(19)41-24(25)9-1-2-12(31)13(32)3-9/h1-7,18,21,23,26,28-37,39H,8H2/t18-,21-,23+,26-,28+/m1/s1
• InChI Key: PXGWEUQZDRUMRE-KQOASZHBSA-N
• Popularity: 6 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: 1.50
• Atomic LogP (AlogP): 0.44
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 6

Synonyms

• [(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-chromen-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl] 3,4,5-trihydroxybenzoate
• 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[[2-O-(3,4,5-trihydroxybenzoyl)-beta-D-glucopyranosyl]oxy]-
• Quercetin-3-O-(2 inverted exclamation marka inverted exclamation marka-O-galloyl)-|A-D-glucopyranoside
• 69624-79-9
• [(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 3,4,5-trihydroxybenzoate
• Quercetin 3-glucoside2''-gallate
• DTXSID901232099
• BDBM50004200
• HY-N11538
• AKOS037514525
• CS-0649309
• Quercetin-3-O-(2-O-galloyl)-beta-D-glucopyranoside
• Quercetin-3-O-(2''-O-galloyl)-beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6249	62.49%
Caco-2	-	0.9099	90.99%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5589	55.89%
OATP2B1 inhibitior	-	0.5486	54.86%
OATP1B1 inhibitior	+	0.7529	75.29%
OATP1B3 inhibitior	+	0.9680	96.80%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.7286	72.86%
P-glycoprotein inhibitior	+	0.6809	68.09%
P-glycoprotein substrate	-	0.5895	58.95%
CYP3A4 substrate	+	0.6731	67.31%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8662	86.62%
CYP3A4 inhibition	-	0.9184	91.84%
CYP2C9 inhibition	-	0.9174	91.74%
CYP2C19 inhibition	-	0.9299	92.99%
CYP2D6 inhibition	-	0.9641	96.41%
CYP1A2 inhibition	-	0.9320	93.20%
CYP2C8 inhibition	+	0.9184	91.84%
CYP inhibitory promiscuity	-	0.8782	87.82%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7263	72.63%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.8679	86.79%
Skin irritation	-	0.8274	82.74%
Skin corrosion	-	0.9638	96.38%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8295	82.95%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	+	0.5929	59.29%
skin sensitisation	-	0.9201	92.01%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.9586	95.86%
Acute Oral Toxicity (c)	IV	0.4205	42.05%
Estrogen receptor binding	+	0.7852	78.52%
Androgen receptor binding	+	0.7724	77.24%
Thyroid receptor binding	+	0.5193	51.93%
Glucocorticoid receptor binding	+	0.6010	60.10%
Aromatase binding	-	0.5218	52.18%
PPAR gamma	+	0.6928	69.28%
Honey bee toxicity	-	0.7570	75.70%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5950	59.50%
Fish aquatic toxicity	+	0.8695	86.95%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2409	P34913	Epoxide hydratase	18050 nM	IC50	PMID: 24679441

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.72%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.90%	91.49%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	98.87%	95.64%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.38%	89.00%
CHEMBL3194	P02766	Transthyretin	96.76%	90.71%
CHEMBL2581	P07339	Cathepsin D	94.90%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.19%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.38%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.83%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.03%	99.15%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	89.78%	95.78%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	88.93%	83.00%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	87.71%	80.78%
CHEMBL3401	O75469	Pregnane X receptor	87.35%	94.73%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	86.52%	97.53%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.87%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.47%	96.09%
CHEMBL4208	P20618	Proteasome component C5	84.11%	90.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.09%	86.92%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	83.80%	94.42%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.90%	96.21%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.79%	95.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.14%	99.23%

Plants that contains it

• Acridocarpus vivy
• Artemisia afra
• Bupleurum chinense
• Carphephorus odoratissimus
• Carya tonkinensis
• Commiphora kua
• Epipactis palustris
• Eucalyptus staigeriana
• Euphorbia humifusa
• Heliotropium arboreum
• Holocarpha obconica
• Ipomopsis polycladon
• Leonurus sibiricus
• Merwilla dracomontana
• Mitrephora diversifolia
• Plantago indica
• Plectranthus fruticosus
• Pyrola japonica
• Rumex obtusifolius
• Selenicereus ocamponis
• Syneilesis palmata
• Tamarix aphylla
• Uncaria donisii
• Xanthosoma sagittifolium
• Zanthoxylum americanum

Cross-Links

• PubChem: 5480249
• NPASS: NPC113836
• ChEMBL: CHEMBL459260