1-[4-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-2-hydroxy-6-methoxyphenyl]ethanone

Details

• Internal ID: d85bb0f6-834d-40f1-b002-c692ada0e264
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: 1-[4-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-2-hydroxy-6-methoxyphenyl]ethanone
• SMILES (Canonical): CC(=O)C1=C(C=C(C=C1OC)OC2C(C(C(C(O2)COC3C(C(CO3)(CO)O)O)O)O)O)O
• SMILES (Isomeric): CC(=O)C1=C(C=C(C=C1OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO[C@H]3[C@@H]([C@](CO3)(CO)O)O)O)O)O)O
• InChI: InChI=1S/C20H28O13/c1-8(22)13-10(23)3-9(4-11(13)29-2)32-18-16(26)15(25)14(24)12(33-18)5-30-19-17(27)20(28,6-21)7-31-19/h3-4,12,14-19,21,23-28H,5-7H2,1-2H3/t12-,14-,15+,16-,17+,18-,19-,20-/m1/s1
• InChI Key: CDQFXFHWSXNKKO-ZITSYKRSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₁₃
• Molecular Weight: 476.40 g/mol
• Exact Mass: 476.15299094 g/mol
• Topological Polar Surface Area (TPSA): 205.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -2.75
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6373	63.73%
Caco-2	-	0.8577	85.77%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7185	71.85%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.9246	92.46%
OATP1B3 inhibitior	+	0.9529	95.29%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.5876	58.76%
P-glycoprotein inhibitior	-	0.7122	71.22%
P-glycoprotein substrate	-	0.6152	61.52%
CYP3A4 substrate	+	0.6409	64.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8636	86.36%
CYP3A4 inhibition	-	0.8643	86.43%
CYP2C9 inhibition	-	0.8995	89.95%
CYP2C19 inhibition	-	0.8725	87.25%
CYP2D6 inhibition	-	0.9146	91.46%
CYP1A2 inhibition	-	0.8826	88.26%
CYP2C8 inhibition	+	0.5395	53.95%
CYP inhibitory promiscuity	-	0.8401	84.01%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6440	64.40%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.9461	94.61%
Skin irritation	-	0.8288	82.88%
Skin corrosion	-	0.9542	95.42%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6449	64.49%
Micronuclear	-	0.6126	61.26%
Hepatotoxicity	-	0.7708	77.08%
skin sensitisation	-	0.8353	83.53%
Respiratory toxicity	-	0.6778	67.78%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	+	0.4948	49.48%
Acute Oral Toxicity (c)	III	0.6940	69.40%
Estrogen receptor binding	+	0.7416	74.16%
Androgen receptor binding	-	0.6562	65.62%
Thyroid receptor binding	+	0.5294	52.94%
Glucocorticoid receptor binding	-	0.5053	50.53%
Aromatase binding	+	0.7173	71.73%
PPAR gamma	+	0.6837	68.37%
Honey bee toxicity	-	0.7910	79.10%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	-	0.4321	43.21%

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	99.51%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.46%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	95.23%	92.94%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.07%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.58%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	90.18%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.04%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.92%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.59%	86.33%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	88.15%	97.21%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.44%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.31%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.07%	94.45%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.54%	91.07%
CHEMBL4208	P20618	Proteasome component C5	86.02%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.31%	95.89%
CHEMBL2243	O00519	Anandamide amidohydrolase	85.17%	97.53%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.87%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.53%	96.95%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.28%	97.36%
CHEMBL2581	P07339	Cathepsin D	83.03%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	82.33%	91.19%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.21%	94.33%
CHEMBL3401	O75469	Pregnane X receptor	81.14%	94.73%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.06%	97.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.88%	99.15%

Plants that contains it

• Erythroxylum cambodianum

Cross-Links

• PubChem: 11784824
• LOTUS: LTS0093325
• wikiData: Q104955010