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

Details

• Internal ID: e569b97b-9f3a-4d14-8dbf-2faf2b25337a
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
• IUPAC Name: [(2S,3R,4R,5S,6S)-4-acetyloxy-2-(acetyloxymethyl)-6-[[(3S,4R,4aS)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]-5-benzoyloxyoxan-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(C3CCOC(=O)C3=CO2)C=C)OC(=O)C4=CC=CC=C4)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@@H]3CCOC(=O)C3=CO2)C=C)OC(=O)C4=CC=CC=C4)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/C40H44O20/c1-4-21-22-13-14-51-36(49)24(22)16-53-38(21)60-40-34(59-35(48)20-9-6-5-7-10-20)33(54-19(3)43)32(27(57-40)17-52-18(2)42)58-37(50)23-11-8-12-25(28(23)44)55-39-31(47)30(46)29(45)26(15-41)56-39/h4-12,16,21-22,26-27,29-34,38-41,44-47H,1,13-15,17H2,2-3H3/t21-,22+,26-,27+,29-,30+,31-,32-,33-,34+,38+,39-,40+/m1/s1
• InChI Key: SABFJVXXJPRXKP-BMAMPQLPSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₄₄O₂₀
• Molecular Weight: 844.80 g/mol
• Exact Mass: 844.24259379 g/mol
• Topological Polar Surface Area (TPSA): 279.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 0.16
• H-Bond Acceptor: 20
• H-Bond Donor: 5
• 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	-	0.8737	87.37%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7257	72.57%
OATP2B1 inhibitior	-	0.5829	58.29%
OATP1B1 inhibitior	+	0.7942	79.42%
OATP1B3 inhibitior	+	0.9297	92.97%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8388	83.88%
P-glycoprotein inhibitior	+	0.7377	73.77%
P-glycoprotein substrate	+	0.5552	55.52%
CYP3A4 substrate	+	0.7163	71.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8835	88.35%
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	+	0.8309	83.09%
CYP inhibitory promiscuity	-	0.7967	79.67%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7319	73.19%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.9077	90.77%
Skin irritation	-	0.7733	77.33%
Skin corrosion	-	0.9357	93.57%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6648	66.48%
Micronuclear	-	0.6267	62.67%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.8240	82.40%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.6060	60.60%
Acute Oral Toxicity (c)	III	0.5726	57.26%
Estrogen receptor binding	+	0.8375	83.75%
Androgen receptor binding	+	0.6673	66.73%
Thyroid receptor binding	+	0.5280	52.80%
Glucocorticoid receptor binding	+	0.6813	68.13%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7364	73.64%
Honey bee toxicity	-	0.7248	72.48%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
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
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.65%	86.33%
CHEMBL2581	P07339	Cathepsin D	97.41%	98.95%
CHEMBL220	P22303	Acetylcholinesterase	95.05%	94.45%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	94.46%	95.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.85%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.78%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.51%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.37%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.40%	91.11%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	90.69%	83.00%
CHEMBL1951	P21397	Monoamine oxidase A	89.67%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.53%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.67%	100.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.62%	96.21%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.44%	93.00%
CHEMBL340	P08684	Cytochrome P450 3A4	86.23%	91.19%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.43%	95.83%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.14%	94.80%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.45%	99.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.15%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.51%	99.17%
CHEMBL5255	O00206	Toll-like receptor 4	82.45%	92.50%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.05%	95.50%
CHEMBL3891	P07384	Calpain 1	81.58%	93.04%

Plants that contains it

• Gentiana scabra
• Patrinia scabiosifolia

Cross-Links

• PubChem: 6325983
• NPASS: NPC219146