[4,5-Diacetyloxy-2-(acetyloxymethyl)-6-[(4-ethenyl-4a-hydroxy-8-oxo-3,4,5,6-tetrahydropyrano[3,4-c]pyran-3-yl)oxy]oxan-3-yl] 2-hydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoate

Details

• Internal ID: 359c41ee-4af6-4d6a-bf42-3942b36a55f4
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
• IUPAC Name: [4,5-diacetyloxy-2-(acetyloxymethyl)-6-[(4-ethenyl-4a-hydroxy-8-oxo-3,4,5,6-tetrahydropyrano[3,4-c]pyran-3-yl)oxy]oxan-3-yl] 2-hydroxy-3-[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)C)OC(=O)C)OC(=O)C4=C(C(=CC=C4)OC5C(C(C(C(O5)CO)O)O)O)O
• SMILES (Isomeric): CC(=O)OCC1C(C(C(C(O1)OC2C(C3(CCOC(=O)C3=CO2)O)C=C)OC(=O)C)OC(=O)C)OC(=O)C4=C(C(=CC=C4)OC5C(C(C(C(O5)CO)O)O)O)O
• InChI: InChI=1S/C35H42O21/c1-5-18-32(49-12-19-31(45)47-10-9-35(18,19)46)56-34-29(51-16(4)39)28(50-15(3)38)27(22(54-34)13-48-14(2)37)55-30(44)17-7-6-8-20(23(17)40)52-33-26(43)25(42)24(41)21(11-36)53-33/h5-8,12,18,21-22,24-29,32-34,36,40-43,46H,1,9-11,13H2,2-4H3
• InChI Key: XINNQYBYFFJBAM-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₂O₂₁
• Molecular Weight: 798.70 g/mol
• Exact Mass: 798.22185834 g/mol
• Topological Polar Surface Area (TPSA): 299.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -2.02
• H-Bond Acceptor: 21
• H-Bond Donor: 6
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7686	76.86%
Caco-2	-	0.8738	87.38%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6653	66.53%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.8056	80.56%
OATP1B3 inhibitior	+	0.8669	86.69%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7776	77.76%
BSEP inhibitior	+	0.7985	79.85%
P-glycoprotein inhibitior	+	0.7441	74.41%
P-glycoprotein substrate	+	0.5388	53.88%
CYP3A4 substrate	+	0.7237	72.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8856	88.56%
CYP3A4 inhibition	-	0.8979	89.79%
CYP2C9 inhibition	-	0.8003	80.03%
CYP2C19 inhibition	-	0.8183	81.83%
CYP2D6 inhibition	-	0.8909	89.09%
CYP1A2 inhibition	-	0.7458	74.58%
CYP2C8 inhibition	+	0.7510	75.10%
CYP inhibitory promiscuity	-	0.9064	90.64%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6665	66.65%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.9099	90.99%
Skin irritation	-	0.7062	70.62%
Skin corrosion	-	0.9302	93.02%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4105	41.05%
Micronuclear	-	0.6567	65.67%
Hepatotoxicity	-	0.6601	66.01%
skin sensitisation	-	0.8239	82.39%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.5614	56.14%
Acute Oral Toxicity (c)	III	0.5764	57.64%
Estrogen receptor binding	+	0.8255	82.55%
Androgen receptor binding	+	0.6548	65.48%
Thyroid receptor binding	+	0.5300	53.00%
Glucocorticoid receptor binding	+	0.7180	71.80%
Aromatase binding	+	0.5871	58.71%
PPAR gamma	+	0.7543	75.43%
Honey bee toxicity	-	0.6587	65.87%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9456	94.56%

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	97.68%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.58%	96.09%
CHEMBL220	P22303	Acetylcholinesterase	96.51%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.75%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.52%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.17%	86.33%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	93.91%	95.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.74%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.71%	95.89%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.65%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.15%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.87%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.84%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.62%	97.09%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.03%	91.24%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.14%	93.00%
CHEMBL3401	O75469	Pregnane X receptor	85.12%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.08%	94.00%
CHEMBL340	P08684	Cytochrome P450 3A4	84.52%	91.19%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.95%	96.61%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	83.93%	82.50%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	82.48%	83.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.70%	95.50%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.66%	96.21%
CHEMBL5028	O14672	ADAM10	80.34%	97.50%
CHEMBL1951	P21397	Monoamine oxidase A	80.28%	91.49%
CHEMBL3891	P07384	Calpain 1	80.25%	93.04%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.04%	94.33%

Plants that contains it

• Gentiana algida
• Gentiana gelida
• Gentiana macrophylla
• Gentiana septemfida
• Gentiana siphonantha
• Gentiana tibetica

Cross-Links

• PubChem: 75144806
• LOTUS: LTS0234700
• wikiData: Q104399575