[(2R,3S,4S,5R,6S)-4,5-diacetyloxy-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-2-(hydroxymethyl)oxan-3-yl] acetate

Details

• Internal ID: 75d6f888-c1e7-4170-985e-3af47bf6fbb9
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-4,5-diacetyloxy-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-2-(hydroxymethyl)oxan-3-yl] acetate
• SMILES (Canonical): CC(=O)OC1C(OC(C(C1OC(=O)C)OC(=O)C)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)CO
• SMILES (Isomeric): CC(=O)O[C@H]1[C@H](O[C@H]([C@@H]([C@H]1OC(=O)C)OC(=O)C)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)CO
• InChI: InChI=1S/C27H26O15/c1-10(29)37-23-19(9-28)41-27(26(39-12(3)31)25(23)38-11(2)30)42-24-21(36)20-17(35)7-14(32)8-18(20)40-22(24)13-4-5-15(33)16(34)6-13/h4-8,19,23,25-28,32-35H,9H2,1-3H3/t19-,23+,25+,26-,27+/m1/s1
• InChI Key: AXCXJIKUZOEPMX-STVYCASWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₆O₁₅
• Molecular Weight: 590.50 g/mol
• Exact Mass: 590.12717012 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.17
• H-Bond Acceptor: 15
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6086	60.86%
Caco-2	-	0.8571	85.71%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6883	68.83%
OATP2B1 inhibitior	-	0.5708	57.08%
OATP1B1 inhibitior	+	0.8867	88.67%
OATP1B3 inhibitior	-	0.2150	21.50%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8334	83.34%
P-glycoprotein inhibitior	+	0.7902	79.02%
P-glycoprotein substrate	-	0.6996	69.96%
CYP3A4 substrate	+	0.6604	66.04%
CYP2C9 substrate	+	0.5662	56.62%
CYP2D6 substrate	-	0.8796	87.96%
CYP3A4 inhibition	-	0.9037	90.37%
CYP2C9 inhibition	-	0.9247	92.47%
CYP2C19 inhibition	-	0.9606	96.06%
CYP2D6 inhibition	-	0.9747	97.47%
CYP1A2 inhibition	-	0.9197	91.97%
CYP2C8 inhibition	+	0.8551	85.51%
CYP inhibitory promiscuity	-	0.8041	80.41%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7204	72.04%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.8814	88.14%
Skin irritation	-	0.8595	85.95%
Skin corrosion	-	0.9615	96.15%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7389	73.89%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	+	0.5429	54.29%
skin sensitisation	-	0.9152	91.52%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.7686	76.86%
Acute Oral Toxicity (c)	III	0.6327	63.27%
Estrogen receptor binding	+	0.8393	83.93%
Androgen receptor binding	+	0.8345	83.45%
Thyroid receptor binding	-	0.5210	52.10%
Glucocorticoid receptor binding	+	0.7259	72.59%
Aromatase binding	-	0.5774	57.74%
PPAR gamma	+	0.7134	71.34%
Honey bee toxicity	-	0.7706	77.06%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6350	63.50%
Fish aquatic toxicity	+	0.8853	88.53%

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	99.47%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.00%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.95%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.48%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.56%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	92.35%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.07%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.90%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.74%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.66%	99.17%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	90.12%	95.64%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.43%	85.14%
CHEMBL1951	P21397	Monoamine oxidase A	85.27%	91.49%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	82.89%	93.65%
CHEMBL3194	P02766	Transthyretin	82.36%	90.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.13%	86.92%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.09%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.99%	95.56%
CHEMBL4208	P20618	Proteasome component C5	80.71%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.56%	91.19%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.47%	95.78%

Plants that contains it

• Tagetes elliptica

Cross-Links

• PubChem: 163034981
• LOTUS: LTS0171836
• wikiData: Q104920447