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

Details

• Internal ID: fbab9688-96f8-4386-bd4d-cd0d1d22037f
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: [(2S,3R,4S,5R,6R)-3-acetyloxy-2-[5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4-oxochromen-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl] acetate
• SMILES (Canonical): CC(=O)OC1C(C(OC(C1OC(=O)C)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C(=C4)OC)O)OC)CO)O
• SMILES (Isomeric): CC(=O)O[C@H]1[C@@H]([C@H](O[C@H]([C@@H]1OC(=O)C)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C(=C4)OC)O)OC)CO)O
• InChI: InChI=1S/C27H28O15/c1-10(29)38-24-21(34)18(9-28)41-27(26(24)39-11(2)30)42-25-22(35)19-14(32)7-13(31)8-15(19)40-23(25)12-5-16(36-3)20(33)17(6-12)37-4/h5-8,18,21,24,26-28,31-34H,9H2,1-4H3/t18-,21-,24+,26-,27+/m1/s1
• InChI Key: ABOCRUNJMFWRRX-FGZZQOONSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₈O₁₅
• Molecular Weight: 592.50 g/mol
• Exact Mass: 592.14282018 g/mol
• Topological Polar Surface Area (TPSA): 217.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 0.91
• H-Bond Acceptor: 15
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7675	76.75%
Caco-2	-	0.8525	85.25%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5738	57.38%
OATP2B1 inhibitior	-	0.7143	71.43%
OATP1B1 inhibitior	+	0.8296	82.96%
OATP1B3 inhibitior	-	0.2286	22.86%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7057	70.57%
P-glycoprotein inhibitior	+	0.7669	76.69%
P-glycoprotein substrate	-	0.5113	51.13%
CYP3A4 substrate	+	0.6572	65.72%
CYP2C9 substrate	-	0.8180	81.80%
CYP2D6 substrate	-	0.8715	87.15%
CYP3A4 inhibition	-	0.8997	89.97%
CYP2C9 inhibition	-	0.8277	82.77%
CYP2C19 inhibition	-	0.9370	93.70%
CYP2D6 inhibition	-	0.9657	96.57%
CYP1A2 inhibition	-	0.9420	94.20%
CYP2C8 inhibition	+	0.7626	76.26%
CYP inhibitory promiscuity	-	0.7524	75.24%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7088	70.88%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.8998	89.98%
Skin irritation	-	0.8575	85.75%
Skin corrosion	-	0.9642	96.42%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4433	44.33%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.9279	92.79%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.7580	75.80%
Acute Oral Toxicity (c)	III	0.6308	63.08%
Estrogen receptor binding	+	0.8067	80.67%
Androgen receptor binding	+	0.6846	68.46%
Thyroid receptor binding	-	0.5233	52.33%
Glucocorticoid receptor binding	+	0.7826	78.26%
Aromatase binding	-	0.5149	51.49%
PPAR gamma	+	0.6132	61.32%
Honey bee toxicity	-	0.7490	74.90%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6549	65.49%
Fish aquatic toxicity	+	0.7821	78.21%

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	99.45%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.60%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.97%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.79%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.38%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.74%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.96%	99.17%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	89.58%	95.64%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.18%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.01%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	88.34%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.09%	95.56%
CHEMBL3194	P02766	Transthyretin	84.86%	90.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.40%	92.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.27%	95.89%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	82.46%	94.42%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.62%	86.92%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.89%	99.15%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.57%	96.00%
CHEMBL4208	P20618	Proteasome component C5	80.57%	90.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.50%	94.33%

Plants that contains it

• Warburgia stuhlmannii

Cross-Links

• PubChem: 12096314
• LOTUS: LTS0115805
• wikiData: Q104908723