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

Details

• Internal ID: 669e9e57-f184-40fc-8ffa-335214c6307f
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: 1-[4-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxy-6-methoxyphenyl]ethanone
• SMILES (Canonical): CC(=O)C1=C(C=C(C=C1OC)OC2C(C(C(C(O2)CO)O)O)OC3C(C(CO3)(CO)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)O)O)O[C@H]3[C@@H]([C@](CO3)(CO)O)O)O
• InChI: InChI=1S/C20H28O13/c1-8(23)13-10(24)3-9(4-11(13)29-2)31-18-16(15(26)14(25)12(5-21)32-18)33-19-17(27)20(28,6-22)7-30-19/h3-4,12,14-19,21-22,24-28H,5-7H2,1-2H3/t12-,14-,15+,16-,17+,18-,19+,20-/m1/s1
• InChI Key: UBVHHYRXHFBYIZ-XIUQVGCESA-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: -1.60
• 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	-	0.6657	66.57%
Caco-2	-	0.8475	84.75%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6772	67.72%
OATP2B1 inhibitior	-	0.8575	85.75%
OATP1B1 inhibitior	+	0.9163	91.63%
OATP1B3 inhibitior	+	0.9567	95.67%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5745	57.45%
P-glycoprotein inhibitior	-	0.7214	72.14%
P-glycoprotein substrate	-	0.6446	64.46%
CYP3A4 substrate	+	0.6523	65.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8636	86.36%
CYP3A4 inhibition	-	0.8421	84.21%
CYP2C9 inhibition	-	0.8980	89.80%
CYP2C19 inhibition	-	0.8811	88.11%
CYP2D6 inhibition	-	0.9139	91.39%
CYP1A2 inhibition	-	0.8806	88.06%
CYP2C8 inhibition	+	0.4569	45.69%
CYP inhibitory promiscuity	-	0.7761	77.61%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6114	61.14%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9381	93.81%
Skin irritation	-	0.8235	82.35%
Skin corrosion	-	0.9483	94.83%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4043	40.43%
Micronuclear	-	0.5467	54.67%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8272	82.72%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	+	0.4732	47.32%
Acute Oral Toxicity (c)	III	0.7539	75.39%
Estrogen receptor binding	+	0.7726	77.26%
Androgen receptor binding	-	0.6101	61.01%
Thyroid receptor binding	+	0.5643	56.43%
Glucocorticoid receptor binding	-	0.4886	48.86%
Aromatase binding	+	0.7380	73.80%
PPAR gamma	+	0.6979	69.79%
Honey bee toxicity	-	0.7305	73.05%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	-	0.5748	57.48%

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%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.11%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	95.66%	92.94%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.77%	94.00%
CHEMBL226	P30542	Adenosine A1 receptor	92.12%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.27%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	90.66%	91.07%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.50%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.68%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.31%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.56%	97.09%
CHEMBL4208	P20618	Proteasome component C5	88.47%	90.00%
CHEMBL2243	O00519	Anandamide amidohydrolase	88.27%	97.53%
CHEMBL340	P08684	Cytochrome P450 3A4	86.75%	91.19%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.36%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.93%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.71%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.57%	94.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.14%	99.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.20%	97.36%
CHEMBL2581	P07339	Cathepsin D	82.91%	98.95%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.79%	97.21%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.56%	97.14%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.28%	97.28%
CHEMBL3401	O75469	Pregnane X receptor	80.56%	94.73%

Plants that contains it

• Celosia argentea

Cross-Links

• PubChem: 46930233
• LOTUS: LTS0231926
• wikiData: Q105269684