2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one

Details

• Internal ID: 3e6bf4bb-c1e2-4756-9f7e-cf549a1faab4
• 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-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1C(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)O)O)O)O)O)O
• SMILES (Isomeric): C1[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)O)O)O)O)O
• InChI: InChI=1S/C26H28O16/c27-9-4-12(30)16-14(5-9)40-23(8-1-2-10(28)11(29)3-8)24(19(16)34)42-26-22(37)20(35)18(33)15(41-26)7-39-25-21(36)17(32)13(31)6-38-25/h1-5,13,15,17-18,20-22,25-33,35-37H,6-7H2/t13-,15-,17+,18-,20+,21-,22-,25+,26+/m1/s1
• InChI Key: YNMFDPCLPIMRFD-PEXUZNNCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₁₆
• Molecular Weight: 596.50 g/mol
• Exact Mass: 596.13773480 g/mol
• Topological Polar Surface Area (TPSA): 266.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -2.08
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 6

Synonyms

• 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• 3',4',5,7-Tetrahydroxy-3-[(6-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy]flavone
• 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(6-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy]-
• Compound NP-004586
• CHEBI:139468
• DTXSID801108980
• AKOS040735837
• 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-[(6-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy]-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4617	46.17%
Caco-2	-	0.9302	93.02%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6348	63.48%
OATP2B1 inhibitior	-	0.5567	55.67%
OATP1B1 inhibitior	+	0.9176	91.76%
OATP1B3 inhibitior	+	0.8755	87.55%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.4820	48.20%
P-glycoprotein inhibitior	-	0.5868	58.68%
P-glycoprotein substrate	-	0.5741	57.41%
CYP3A4 substrate	+	0.6614	66.14%
CYP2C9 substrate	-	0.6831	68.31%
CYP2D6 substrate	-	0.8574	85.74%
CYP3A4 inhibition	-	0.9216	92.16%
CYP2C9 inhibition	-	0.9563	95.63%
CYP2C19 inhibition	-	0.9069	90.69%
CYP2D6 inhibition	-	0.9175	91.75%
CYP1A2 inhibition	-	0.9253	92.53%
CYP2C8 inhibition	+	0.8625	86.25%
CYP inhibitory promiscuity	-	0.8943	89.43%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6832	68.32%
Eye corrosion	-	0.9935	99.35%
Eye irritation	-	0.8822	88.22%
Skin irritation	-	0.8248	82.48%
Skin corrosion	-	0.9684	96.84%
Ames mutagenesis	+	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4231	42.31%
Micronuclear	+	0.6174	61.74%
Hepatotoxicity	+	0.5326	53.26%
skin sensitisation	-	0.9031	90.31%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.9465	94.65%
Acute Oral Toxicity (c)	III	0.4775	47.75%
Estrogen receptor binding	+	0.8204	82.04%
Androgen receptor binding	+	0.6887	68.87%
Thyroid receptor binding	+	0.5596	55.96%
Glucocorticoid receptor binding	+	0.5371	53.71%
Aromatase binding	+	0.6431	64.31%
PPAR gamma	+	0.7679	76.79%
Honey bee toxicity	-	0.7439	74.39%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5950	59.50%
Fish aquatic toxicity	+	0.8955	89.55%

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	99.76%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.23%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.91%	89.00%
CHEMBL2581	P07339	Cathepsin D	96.29%	98.95%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	94.10%	95.64%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.98%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.17%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.43%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.10%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.94%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.49%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	88.68%	94.73%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	87.68%	80.33%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.23%	95.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.90%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.15%	99.17%
CHEMBL4208	P20618	Proteasome component C5	83.19%	90.00%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	82.59%	95.53%
CHEMBL3194	P02766	Transthyretin	82.59%	90.71%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.27%	90.71%

Plants that contains it

• Amaranthus hypochondriacus
• Berberis repens
• Cistus ladanifer
• Croton laccifer
• Euphorbia myrsinites
• Helicteres angustifolia
• Hippeastrum papilio
• Limnocharis flava
• Lycopodium thyoides
• Millettia ferruginea
• Sedum litoreum
• Senecio viscosus
• Teucrium asiaticum
• Thermopsis dolichocarpa
• Vicia amurensis
• Wyethia mollis
• Zanthoxylum americanum

Cross-Links

• PubChem: 5315208
• NPASS: NPC111351
• LOTUS: LTS0274758
• wikiData: Q105350997