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

Details

• Internal ID: ba06370e-8cc3-4ca4-bbdb-e20740026228
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
• IUPAC Name: [(2R,3R,4S,5R,6S)-4-acetyloxy-2-(acetyloxymethyl)-6-[[(3S,4R,4aR)-4-ethenyl-4a-hydroxy-8-oxo-3,4,5,6-tetrahydropyrano[3,4-c]pyran-3-yl]oxy]-5-(2,5-dihydroxybenzoyl)oxyoxan-3-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(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)O[C@H]2[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/c1-4-21-37(56-14-22-36(52)54-11-10-40(21,22)53)63-39-33(62-35(51)20-12-18(44)8-9-23(20)45)32(57-17(3)43)31(26(60-39)15-55-16(2)42)61-34(50)19-6-5-7-24(27(19)46)58-38-30(49)29(48)28(47)25(13-41)59-38/h4-9,12,14,21,25-26,28-33,37-39,41,44-49,53H,1,10-11,13,15H2,2-3H3/t21-,25+,26+,28+,29-,30+,31+,32-,33+,37-,38+,39-,40+/m0/s1
• InChI Key: UDMJOEXVFLSODB-ASQSGCACSA-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	-	0.8732	87.32%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6917	69.17%
OATP2B1 inhibitior	-	0.8601	86.01%
OATP1B1 inhibitior	+	0.8052	80.52%
OATP1B3 inhibitior	+	0.9129	91.29%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7846	78.46%
BSEP inhibitior	+	0.7903	79.03%
P-glycoprotein inhibitior	+	0.7373	73.73%
P-glycoprotein substrate	+	0.6360	63.60%
CYP3A4 substrate	+	0.7321	73.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8856	88.56%
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	+	0.8099	80.99%
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	-	0.9050	90.50%
Skin irritation	-	0.7375	73.75%
Skin corrosion	-	0.9270	92.70%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6969	69.69%
Micronuclear	-	0.6167	61.67%
Hepatotoxicity	-	0.7101	71.01%
skin sensitisation	-	0.8209	82.09%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6287	62.87%
Acute Oral Toxicity (c)	III	0.5625	56.25%
Estrogen receptor binding	+	0.8341	83.41%
Androgen receptor binding	+	0.7030	70.30%
Thyroid receptor binding	+	0.5537	55.37%
Glucocorticoid receptor binding	+	0.6928	69.28%
Aromatase binding	+	0.5647	56.47%
PPAR gamma	+	0.7680	76.80%
Honey bee toxicity	-	0.6367	63.67%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
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	99.28%	91.11%
CHEMBL220	P22303	Acetylcholinesterase	98.93%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.15%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.87%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.97%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.18%	89.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	94.00%	94.80%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	93.13%	95.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.83%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.87%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	89.98%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.73%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	89.37%	91.49%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.16%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.43%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.23%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	87.16%	94.73%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.65%	97.25%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	85.39%	82.50%
CHEMBL3891	P07384	Calpain 1	85.11%	93.04%
CHEMBL4208	P20618	Proteasome component C5	84.28%	90.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.15%	91.07%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.09%	95.89%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	81.56%	83.00%
CHEMBL5255	O00206	Toll-like receptor 4	81.01%	92.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.64%	92.62%
CHEMBL1937	Q92769	Histone deacetylase 2	80.63%	94.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.30%	99.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.19%	95.50%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.17%	96.61%

Plants that contains it

• Acmella ciliata
• Gentiana siphonantha

Cross-Links

• PubChem: 101937469
• LOTUS: LTS0217460
• wikiData: Q105222885