[(2S,3S,4R,5S,6R)-4-acetyloxy-2-(acetyloxymethyl)-6-[[(3S,4S,4aS)-4-ethenyl-4a-hydroxy-8-oxo-3,4,5,6-tetrahydropyrano[3,4-c]pyran-3-yl]oxy]-5-(3,4-dihydroxybenzoyl)oxyoxan-3-yl] 2-hydroxy-3-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoate

Details

• Internal ID: 3be68f3f-a9c5-4735-ab22-aefa8288b0d5
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
• IUPAC Name: [(2S,3S,4R,5S,6R)-4-acetyloxy-2-(acetyloxymethyl)-6-[[(3S,4S,4aS)-4-ethenyl-4a-hydroxy-8-oxo-3,4,5,6-tetrahydropyrano[3,4-c]pyran-3-yl]oxy]-5-(3,4-dihydroxybenzoyl)oxyoxan-3-yl] 2-hydroxy-3-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC2C(C3(CCOC(=O)C3=CO2)O)C=C)OC(=O)C4=CC(=C(C=C4)O)O)OC(=O)C)OC(=O)C5=C(C(=CC=C5)OC6C(C(C(C(O6)CO)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@]3(CCOC(=O)C3=CO2)O)C=C)OC(=O)C4=CC(=C(C=C4)O)O)OC(=O)C)OC(=O)C5=C(C(=CC=C5)O[C@@H]6[C@H]([C@@H]([C@H]([C@@H](O6)CO)O)O)O)O
• InChI: InChI=1S/C40H44O23/c1-4-20-37(56-14-21-36(52)54-11-10-40(20,21)53)63-39-33(62-34(50)18-8-9-22(44)23(45)12-18)32(57-17(3)43)31(26(60-39)15-55-16(2)42)61-35(51)19-6-5-7-24(27(19)46)58-38-30(49)29(48)28(47)25(13-41)59-38/h4-9,12,14,20,25-26,28-33,37-39,41,44-49,53H,1,10-11,13,15H2,2-3H3/t20-,25+,26+,28+,29-,30+,31+,32-,33+,37+,38+,39-,40+/m1/s1
• InChI Key: VYCHTTCUSVZEJL-MIFSYRGISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₄₄O₂₃
• Molecular Weight: 892.80 g/mol
• Exact Mass: 892.22733765 g/mol
• Topological Polar Surface Area (TPSA): 340.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): -1.31
• H-Bond Acceptor: 23
• H-Bond Donor: 8
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7218	72.18%
Caco-2	-	0.8730	87.30%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6917	69.17%
OATP2B1 inhibitior	-	0.8604	86.04%
OATP1B1 inhibitior	+	0.7983	79.83%
OATP1B3 inhibitior	+	0.9129	91.29%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7846	78.46%
BSEP inhibitior	+	0.7736	77.36%
P-glycoprotein inhibitior	+	0.7426	74.26%
P-glycoprotein substrate	+	0.6260	62.60%
CYP3A4 substrate	+	0.7327	73.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8821	88.21%
CYP3A4 inhibition	-	0.8835	88.35%
CYP2C9 inhibition	-	0.7855	78.55%
CYP2C19 inhibition	-	0.7973	79.73%
CYP2D6 inhibition	-	0.8618	86.18%
CYP1A2 inhibition	-	0.7422	74.22%
CYP2C8 inhibition	+	0.8097	80.97%
CYP inhibitory promiscuity	-	0.8943	89.43%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6803	68.03%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.9051	90.51%
Skin irritation	-	0.7375	73.75%
Skin corrosion	-	0.9270	92.70%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6528	65.28%
Micronuclear	-	0.6167	61.67%
Hepatotoxicity	-	0.6351	63.51%
skin sensitisation	-	0.8209	82.09%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6252	62.52%
Acute Oral Toxicity (c)	III	0.5625	56.25%
Estrogen receptor binding	+	0.8087	80.87%
Androgen receptor binding	+	0.7015	70.15%
Thyroid receptor binding	+	0.5464	54.64%
Glucocorticoid receptor binding	+	0.6883	68.83%
Aromatase binding	+	0.5594	55.94%
PPAR gamma	+	0.7556	75.56%
Honey bee toxicity	-	0.6377	63.77%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9714	97.14%

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	99.25%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.57%	91.49%
CHEMBL220	P22303	Acetylcholinesterase	98.48%	94.45%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	98.13%	95.17%
CHEMBL2581	P07339	Cathepsin D	96.63%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.87%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.95%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.56%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.54%	95.89%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	93.00%	94.80%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	92.71%	83.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.26%	100.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.80%	96.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.10%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	89.36%	91.19%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.01%	96.61%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.54%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.39%	97.09%
CHEMBL4208	P20618	Proteasome component C5	86.50%	90.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.05%	91.24%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.96%	95.83%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	85.23%	82.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.38%	91.07%
CHEMBL3401	O75469	Pregnane X receptor	83.74%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.11%	94.00%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	82.85%	94.42%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.66%	92.62%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	81.95%	90.24%
CHEMBL3891	P07384	Calpain 1	81.88%	93.04%
CHEMBL5255	O00206	Toll-like receptor 4	81.57%	92.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.17%	99.17%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.70%	98.75%

Plants that contains it

• Gentiana macrophylla

Cross-Links

• PubChem: 163191329
• LOTUS: LTS0213688
• wikiData: Q105298882