[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Details

• Internal ID: 67c0c5b2-2aea-4a82-ad63-ab130f384826
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC2=CC(=C3C(=C2)OC(=CC3=O)C4=CC(=C(C=C4)O)O)O)O)O)O
• SMILES (Isomeric): CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC2=CC(=C3C(=C2)OC(=CC3=O)C4=CC(=C(C=C4)O)O)O)O)O)O
• InChI: InChI=1S/C23H22O12/c1-9(24)32-8-18-20(29)21(30)22(31)23(35-18)33-11-5-14(27)19-15(28)7-16(34-17(19)6-11)10-2-3-12(25)13(26)4-10/h2-7,18,20-23,25-27,29-31H,8H2,1H3/t18-,20-,21+,22-,23-/m1/s1
• InChI Key: BURUDCAXNNYPGK-DODNOZFWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₂O₁₂
• Molecular Weight: 490.40 g/mol
• Exact Mass: 490.11112613 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.33
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5759	57.59%
Caco-2	-	0.8955	89.55%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6926	69.26%
OATP2B1 inhibitior	-	0.5439	54.39%
OATP1B1 inhibitior	+	0.9495	94.95%
OATP1B3 inhibitior	+	0.9515	95.15%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.6932	69.32%
P-glycoprotein inhibitior	-	0.5303	53.03%
P-glycoprotein substrate	-	0.7085	70.85%
CYP3A4 substrate	+	0.5967	59.67%
CYP2C9 substrate	+	0.5334	53.34%
CYP2D6 substrate	-	0.8764	87.64%
CYP3A4 inhibition	-	0.9505	95.05%
CYP2C9 inhibition	-	0.9129	91.29%
CYP2C19 inhibition	-	0.9233	92.33%
CYP2D6 inhibition	-	0.9603	96.03%
CYP1A2 inhibition	-	0.8935	89.35%
CYP2C8 inhibition	+	0.7281	72.81%
CYP inhibitory promiscuity	-	0.8491	84.91%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7134	71.34%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.8887	88.87%
Skin irritation	-	0.8133	81.33%
Skin corrosion	-	0.9497	94.97%
Ames mutagenesis	+	0.5936	59.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.3789	37.89%
Micronuclear	+	0.5892	58.92%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.9339	93.39%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.8436	84.36%
Acute Oral Toxicity (c)	III	0.5815	58.15%
Estrogen receptor binding	+	0.7590	75.90%
Androgen receptor binding	+	0.6950	69.50%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6302	63.02%
Aromatase binding	-	0.5141	51.41%
PPAR gamma	+	0.7198	71.98%
Honey bee toxicity	-	0.7352	73.52%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6750	67.50%
Fish aquatic toxicity	+	0.9613	96.13%

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	99.50%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.99%	91.49%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.32%	85.14%
CHEMBL2581	P07339	Cathepsin D	96.83%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.20%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.99%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.37%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	93.12%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.95%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.97%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.67%	94.45%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.65%	95.78%
CHEMBL3194	P02766	Transthyretin	84.64%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.30%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.11%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.07%	90.71%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.17%	94.80%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.13%	95.89%

Plants that contains it

• Calicotome villosa
• Camchaya loloana
• Campanula patula
• Cynara cardunculus
• Dendrobium moniliforme
• Erysimum siliculosum
• Eschenbachia japonica
• Euphrasia stricta
• Kaempferia rotunda
• Platycodon grandiflorus
• Salix gilgiana

Cross-Links

• PubChem: 21721976
• NPASS: NPC43763
• LOTUS: LTS0204111
• wikiData: Q104946283