1-[3-[(2R,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-1,6-dimethoxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxynaphthalen-2-yl]ethanone

Details

• Internal ID: c38c7bd3-98f0-4325-b6ff-1b7c4b7bc1b4
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: 1-[3-[(2R,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-1,6-dimethoxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxynaphthalen-2-yl]ethanone
• SMILES (Canonical): CC(=O)C1=C(C2=C(C=C(C=C2C=C1OC3C(C(CO3)(CO)O)O)OC)OC4C(C(C(C(O4)CO)O)O)O)OC
• SMILES (Isomeric): CC(=O)C1=C(C2=C(C=C(C=C2C=C1O[C@@H]3[C@H]([C@@](CO3)(CO)O)O)OC)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC
• InChI: InChI=1S/C25H32O14/c1-10(28)16-13(38-24-22(32)25(33,8-27)9-36-24)5-11-4-12(34-2)6-14(17(11)21(16)35-3)37-23-20(31)19(30)18(29)15(7-26)39-23/h4-6,15,18-20,22-24,26-27,29-33H,7-9H2,1-3H3/t15-,18-,19+,20-,22-,23-,24-,25+/m1/s1
• InChI Key: PGDDDJBSORSPAG-NCAJNNROSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂O₁₄
• Molecular Weight: 556.50 g/mol
• Exact Mass: 556.17920569 g/mol
• Topological Polar Surface Area (TPSA): 214.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -1.94
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 9

Synonyms

• BDBM50133040

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5982	59.82%
Caco-2	-	0.8347	83.47%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5299	52.99%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.8973	89.73%
OATP1B3 inhibitior	+	0.9587	95.87%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8418	84.18%
P-glycoprotein inhibitior	-	0.4361	43.61%
P-glycoprotein substrate	-	0.6638	66.38%
CYP3A4 substrate	+	0.6434	64.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8474	84.74%
CYP3A4 inhibition	-	0.9154	91.54%
CYP2C9 inhibition	-	0.9347	93.47%
CYP2C19 inhibition	-	0.8946	89.46%
CYP2D6 inhibition	-	0.9209	92.09%
CYP1A2 inhibition	-	0.8515	85.15%
CYP2C8 inhibition	+	0.5224	52.24%
CYP inhibitory promiscuity	-	0.8218	82.18%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5581	55.81%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9287	92.87%
Skin irritation	-	0.8160	81.60%
Skin corrosion	-	0.9492	94.92%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7333	73.33%
Micronuclear	+	0.5833	58.33%
Hepatotoxicity	-	0.6802	68.02%
skin sensitisation	-	0.8631	86.31%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.5827	58.27%
Acute Oral Toxicity (c)	III	0.6713	67.13%
Estrogen receptor binding	+	0.6859	68.59%
Androgen receptor binding	-	0.4934	49.34%
Thyroid receptor binding	+	0.5269	52.69%
Glucocorticoid receptor binding	+	0.7709	77.09%
Aromatase binding	+	0.6051	60.51%
PPAR gamma	+	0.6352	63.52%
Honey bee toxicity	-	0.7966	79.66%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.6650	66.50%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2409	P34913	Epoxide hydratase	600 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.26%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.79%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.15%	96.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.46%	94.00%
CHEMBL226	P30542	Adenosine A1 receptor	91.31%	95.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.04%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.84%	97.09%
CHEMBL4208	P20618	Proteasome component C5	87.60%	90.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.54%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.93%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.90%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.72%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.07%	96.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.62%	95.89%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.55%	91.24%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.06%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	82.98%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.46%	92.62%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.42%	97.21%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.77%	86.92%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.70%	85.14%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.43%	95.83%

Plants that contains it

• Senna tora

Cross-Links

• PubChem: 122196301
• LOTUS: LTS0017297
• wikiData: Q105208323