[(2R,3R,4S,5R,6S)-2-(acetyloxymethyl)-6-[[(3S,4R,4aS)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]-3,5-dihydroxyoxan-4-yl] 2-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoate

Details

• Internal ID: 23adf55e-353f-469b-8d6f-93f963cd60df
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: [(2R,3R,4S,5R,6S)-2-(acetyloxymethyl)-6-[[(3S,4R,4aS)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]-3,5-dihydroxyoxan-4-yl] 2-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC2C(C3CCOC(=O)C3=CO2)C=C)O)OC(=O)C4=C(C(=CC=C4)OC5C(C(C(C(O5)CO)O)O)O)O)O
• SMILES (Isomeric): CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2[C@@H]([C@@H]3CCOC(=O)C3=CO2)C=C)O)OC(=O)C4=C(C(=CC=C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O
• InChI: InChI=1S/C31H38O18/c1-3-13-14-7-8-42-27(40)16(14)10-44-29(13)49-31-25(39)26(22(36)19(47-31)11-43-12(2)33)48-28(41)15-5-4-6-17(20(15)34)45-30-24(38)23(37)21(35)18(9-32)46-30/h3-6,10,13-14,18-19,21-26,29-32,34-39H,1,7-9,11H2,2H3/t13-,14+,18-,19-,21-,22-,23+,24-,25-,26+,29+,30-,31+/m1/s1
• InChI Key: FQQYPXQSDFVHJX-XDLLGCQKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₃₈O₁₈
• Molecular Weight: 698.60 g/mol
• Exact Mass: 698.20581436 g/mol
• Topological Polar Surface Area (TPSA): 267.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -2.27
• H-Bond Acceptor: 18
• H-Bond Donor: 7
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6576	65.76%
Caco-2	-	0.8898	88.98%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7350	73.50%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.8096	80.96%
OATP1B3 inhibitior	+	0.9342	93.42%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.6496	64.96%
P-glycoprotein inhibitior	+	0.6513	65.13%
P-glycoprotein substrate	+	0.5153	51.53%
CYP3A4 substrate	+	0.7060	70.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8835	88.35%
CYP3A4 inhibition	-	0.9276	92.76%
CYP2C9 inhibition	-	0.7268	72.68%
CYP2C19 inhibition	-	0.7229	72.29%
CYP2D6 inhibition	-	0.8573	85.73%
CYP1A2 inhibition	-	0.6805	68.05%
CYP2C8 inhibition	+	0.7672	76.72%
CYP inhibitory promiscuity	-	0.7871	78.71%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6987	69.87%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.9133	91.33%
Skin irritation	-	0.7612	76.12%
Skin corrosion	-	0.9362	93.62%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4294	42.94%
Micronuclear	-	0.6567	65.67%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.8044	80.44%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.5530	55.30%
Acute Oral Toxicity (c)	III	0.5569	55.69%
Estrogen receptor binding	+	0.8010	80.10%
Androgen receptor binding	+	0.6212	62.12%
Thyroid receptor binding	-	0.5356	53.56%
Glucocorticoid receptor binding	+	0.5698	56.98%
Aromatase binding	+	0.5541	55.41%
PPAR gamma	+	0.6472	64.72%
Honey bee toxicity	-	0.7425	74.25%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9548	95.48%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL220	P22303	Acetylcholinesterase	98.99%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.08%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.99%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.48%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.29%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.99%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.35%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.62%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.70%	95.89%
CHEMBL1951	P21397	Monoamine oxidase A	89.03%	91.49%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	88.91%	94.80%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.99%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.42%	100.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	87.01%	95.17%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.09%	91.24%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.28%	96.21%
CHEMBL3401	O75469	Pregnane X receptor	83.93%	94.73%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	83.81%	82.50%
CHEMBL340	P08684	Cytochrome P450 3A4	83.57%	91.19%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.29%	96.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.47%	93.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.93%	94.33%

Plants that contains it

• Nitraria tangutorum

Cross-Links

• PubChem: 102580781
• NPASS: NPC185795