2-(3,4-Dihydroxyphenyl)-3-[(O-beta-D-glucopyranosyl-(1-->2)-O-[beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranosyl)oxy]-5,7-dihydroxy-4H-1-benzopyran-4-one

Details

• Internal ID: a00b44fb-0731-472e-a9fc-e37ea2f45d2d
• 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-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-5,7-dihydroxychromen-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)OC6C(C(C(C(O6)CO)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[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)O
• InChI: InChI=1S/C33H40O22/c34-6-15-19(40)23(44)26(47)31(51-15)49-8-17-21(42)25(46)30(55-32-27(48)24(45)20(41)16(7-35)52-32)33(53-17)54-29-22(43)18-13(39)4-10(36)5-14(18)50-28(29)9-1-2-11(37)12(38)3-9/h1-5,15-17,19-21,23-27,30-42,44-48H,6-8H2/t15-,16-,17-,19-,20-,21-,23+,24+,25+,26-,27-,30-,31-,32+,33+/m1/s1
• InChI Key: QSUCYXFFQLQGKE-JGPRCQAHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀O₂₂
• Molecular Weight: 788.70 g/mol
• Exact Mass: 788.20112290 g/mol
• Topological Polar Surface Area (TPSA): 365.00 Ų
• XlogP: -3.40
• Atomic LogP (AlogP): -4.89
• H-Bond Acceptor: 22
• H-Bond Donor: 14
• Rotatable Bonds: 10

Synonyms

• 2-(3,4-Dihydroxyphenyl)-3-[(O-beta-D-glucopyranosyl-(1-->2)-O-[beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranosyl)oxy]-5,7-dihydroxy-4H-1-benzopyran-4-one
• 55696-56-5

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5736	57.36%
Caco-2	-	0.9139	91.39%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5848	58.48%
OATP2B1 inhibitior	-	0.5692	56.92%
OATP1B1 inhibitior	+	0.9074	90.74%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.5927	59.27%
P-glycoprotein inhibitior	-	0.4732	47.32%
P-glycoprotein substrate	-	0.6066	60.66%
CYP3A4 substrate	+	0.6638	66.38%
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	+	0.8646	86.46%
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	-	0.9039	90.39%
Skin irritation	-	0.8255	82.55%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6551	65.51%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	+	0.5054	50.54%
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	-	0.8201	82.01%
Acute Oral Toxicity (c)	IV	0.4763	47.63%
Estrogen receptor binding	+	0.8112	81.12%
Androgen receptor binding	+	0.6614	66.14%
Thyroid receptor binding	-	0.4871	48.71%
Glucocorticoid receptor binding	-	0.6088	60.88%
Aromatase binding	+	0.5854	58.54%
PPAR gamma	+	0.7459	74.59%
Honey bee toxicity	-	0.6833	68.33%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5550	55.50%
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	99.70%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.06%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	96.66%	91.49%
CHEMBL2581	P07339	Cathepsin D	94.43%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.55%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.11%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	91.18%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.91%	86.33%
CHEMBL3194	P02766	Transthyretin	89.85%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.35%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.12%	94.45%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	87.66%	95.64%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.42%	86.92%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.84%	95.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.78%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.41%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.46%	97.09%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	80.20%	80.78%

Plants that contains it

• Primula auricula

Cross-Links

• PubChem: 162849558
• LOTUS: LTS0017000
• wikiData: Q105227368