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

Details

• Internal ID: 9c7cd44c-4645-48f5-a249-d4bf4a4912fc
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
• IUPAC Name: [(2R,3S,4R,5S,6S)-4-acetyloxy-6-(acetyloxymethyl)-2-[[(3R,4S,4aS)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]-5-[3-hydroxy-2-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoyl]oxyoxan-3-yl] 2,3-dihydroxybenzoate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC2C(C3CCOC(=O)C3=CO2)C=C)OC(=O)C4=C(C(=CC=C4)O)O)OC(=O)C)OC(=O)C5=C(C(=CC=C5)O)OC6C(C(C(C(O6)CO)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)OC(=O)C4=C(C(=CC=C4)O)O)OC(=O)C)OC(=O)C5=C(C(=CC=C5)O)O[C@@H]6[C@H]([C@@H]([C@H]([C@@H](O6)CO)O)O)O
• InChI: InChI=1S/C40H44O22/c1-4-18-19-11-12-53-35(50)22(19)14-55-38(18)62-40-34(60-36(51)20-7-5-9-23(44)27(20)46)33(56-17(3)43)32(26(58-40)15-54-16(2)42)59-37(52)21-8-6-10-24(45)31(21)61-39-30(49)29(48)28(47)25(13-41)57-39/h4-10,14,18-19,25-26,28-30,32-34,38-41,44-49H,1,11-13,15H2,2-3H3/t18-,19-,25-,26-,28-,29+,30-,32-,33+,34-,38+,39+,40+/m0/s1
• InChI Key: PCQHAARAQYTSDQ-OPCCJVHKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₄₄O₂₂
• Molecular Weight: 876.80 g/mol
• Exact Mass: 876.23242303 g/mol
• Topological Polar Surface Area (TPSA): 319.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): -0.43
• H-Bond Acceptor: 22
• H-Bond Donor: 7
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6165	61.65%
Caco-2	-	0.8783	87.83%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7257	72.57%
OATP2B1 inhibitior	-	0.7212	72.12%
OATP1B1 inhibitior	+	0.7952	79.52%
OATP1B3 inhibitior	+	0.9297	92.97%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.6907	69.07%
P-glycoprotein inhibitior	+	0.7247	72.47%
P-glycoprotein substrate	+	0.5177	51.77%
CYP3A4 substrate	+	0.7172	71.72%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8802	88.02%
CYP3A4 inhibition	-	0.8873	88.73%
CYP2C9 inhibition	-	0.7449	74.49%
CYP2C19 inhibition	-	0.7465	74.65%
CYP2D6 inhibition	-	0.8573	85.73%
CYP1A2 inhibition	-	0.6854	68.54%
CYP2C8 inhibition	+	0.7643	76.43%
CYP inhibitory promiscuity	-	0.7967	79.67%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7319	73.19%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.9072	90.72%
Skin irritation	-	0.7733	77.33%
Skin corrosion	-	0.9357	93.57%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4110	41.10%
Micronuclear	-	0.6267	62.67%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8240	82.40%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.4691	46.91%
Acute Oral Toxicity (c)	III	0.5726	57.26%
Estrogen receptor binding	+	0.8486	84.86%
Androgen receptor binding	+	0.6897	68.97%
Thyroid receptor binding	+	0.5386	53.86%
Glucocorticoid receptor binding	+	0.6668	66.68%
Aromatase binding	+	0.5550	55.50%
PPAR gamma	+	0.7400	74.00%
Honey bee toxicity	-	0.7283	72.83%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.9809	98.09%

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	97.98%	91.11%
CHEMBL220	P22303	Acetylcholinesterase	97.96%	94.45%
CHEMBL2581	P07339	Cathepsin D	97.22%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.00%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.25%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.56%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.26%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.57%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	90.52%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.28%	94.45%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.70%	94.80%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	89.36%	95.17%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	88.93%	91.24%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.38%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.92%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	87.68%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.38%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.67%	97.25%
CHEMBL1951	P21397	Monoamine oxidase A	86.65%	91.49%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	84.57%	83.00%
CHEMBL1937	Q92769	Histone deacetylase 2	84.43%	94.75%
CHEMBL5255	O00206	Toll-like receptor 4	83.82%	92.50%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.54%	95.83%
CHEMBL340	P08684	Cytochrome P450 3A4	82.15%	91.19%

Plants that contains it

• Gentiana tibetica

Cross-Links

• PubChem: 163195362
• LOTUS: LTS0226257
• wikiData: Q105205926