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

Details

• Internal ID: 47c51bd9-3a89-4874-9b31-5b7032524676
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
• IUPAC Name: [(2S,3R,4S,5R,6R)-4-acetyloxy-6-(acetyloxymethyl)-2-[[(4R,4aR)-4-ethenyl-4a-hydroxy-8-oxo-3,4,5,6-tetrahydropyrano[3,4-c]pyran-3-yl]oxy]-5-[2-hydroxy-3-[(2S,3R,4S,5S,6R)-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(C3(CCOC(=O)C3=CO2)O)C=C)OC(=O)C4=C(C(=CC=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)OC2[C@@H]([C@@]3(CCOC(=O)C3=CO2)O)C=C)OC(=O)C4=C(C(=CC=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)54-12-11-40(20,21)53)63-39-33(62-34(50)18-7-5-9-22(44)26(18)45)32(57-17(3)43)31(25(60-39)15-55-16(2)42)61-35(51)19-8-6-10-23(27(19)46)58-38-30(49)29(48)28(47)24(13-41)59-38/h4-10,14,20,24-25,28-33,37-39,41,44-49,53H,1,11-13,15H2,2-3H3/t20-,24+,25+,28+,29-,30+,31+,32-,33+,37?,38+,39-,40+/m0/s1
• InChI Key: RMXNEIZTRAIXJT-BZZULXKDSA-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: 0.90
• 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	-	0.8731	87.31%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6917	69.17%
OATP2B1 inhibitior	-	0.8603	86.03%
OATP1B1 inhibitior	+	0.8114	81.14%
OATP1B3 inhibitior	+	0.9129	91.29%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7846	78.46%
BSEP inhibitior	+	0.8024	80.24%
P-glycoprotein inhibitior	+	0.7377	73.77%
P-glycoprotein substrate	+	0.5931	59.31%
CYP3A4 substrate	+	0.7276	72.76%
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	+	0.7674	76.74%
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	-	0.9052	90.52%
Skin irritation	-	0.7375	73.75%
Skin corrosion	-	0.9270	92.70%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7042	70.42%
Micronuclear	-	0.6167	61.67%
Hepatotoxicity	-	0.6851	68.51%
skin sensitisation	-	0.8209	82.09%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.5946	59.46%
Acute Oral Toxicity (c)	III	0.5625	56.25%
Estrogen receptor binding	+	0.8309	83.09%
Androgen receptor binding	+	0.6819	68.19%
Thyroid receptor binding	+	0.5527	55.27%
Glucocorticoid receptor binding	+	0.6927	69.27%
Aromatase binding	+	0.5631	56.31%
PPAR gamma	+	0.7699	76.99%
Honey bee toxicity	-	0.6540	65.40%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
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	98.27%	91.11%
CHEMBL220	P22303	Acetylcholinesterase	97.01%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.41%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.34%	98.95%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	95.07%	95.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.30%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.71%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.29%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.78%	97.25%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.56%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.25%	95.56%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	89.37%	91.24%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.31%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.26%	100.00%
CHEMBL1951	P21397	Monoamine oxidase A	89.26%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.91%	94.45%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.73%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.73%	97.09%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	87.01%	82.50%
CHEMBL1937	Q92769	Histone deacetylase 2	86.98%	94.75%
CHEMBL3401	O75469	Pregnane X receptor	85.48%	94.73%
CHEMBL340	P08684	Cytochrome P450 3A4	85.43%	91.19%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	85.13%	83.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.93%	95.83%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.72%	95.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.42%	92.62%
CHEMBL5028	O14672	ADAM10	80.34%	97.50%

Plants that contains it

• Gentiana macrophylla

Cross-Links

• PubChem: 10629539
• NPASS: NPC29063