methyl (4R,5E,6S)-5-ethylidene-4-[2-oxo-2-[[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(7-hydroxy-2-oxochromen-6-yl)oxyoxan-2-yl]methoxy]ethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate

Details

• Internal ID: 6e99dad1-d8e7-4c8f-b2f0-89b64cd73c45
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Coumarin glycosides
• IUPAC Name: methyl (4R,5E,6S)-5-ethylidene-4-[2-oxo-2-[[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(7-hydroxy-2-oxochromen-6-yl)oxyoxan-2-yl]methoxy]ethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
• SMILES (Canonical): CC=C1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)OC)CC(=O)OCC3C(C(C(C(O3)OC4=C(C=C5C(=C4)C=CC(=O)O5)O)O)O)O
• SMILES (Isomeric): C/C=C/1\[C@H](C(=CO[C@H]1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)OC)CC(=O)OC[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)OC4=C(C=C5C(=C4)C=CC(=O)O5)O)O)O)O
• InChI: InChI=1S/C32H38O19/c1-3-13-14(15(29(43)44-2)10-46-30(13)51-32-28(42)25(39)23(37)19(9-33)49-32)7-22(36)45-11-20-24(38)26(40)27(41)31(50-20)48-18-6-12-4-5-21(35)47-17(12)8-16(18)34/h3-6,8,10,14,19-20,23-28,30-34,37-42H,7,9,11H2,1-2H3/b13-3+/t14-,19-,20+,23-,24+,25+,26-,27+,28-,30+,31+,32+/m1/s1
• InChI Key: XSXBQKATBVMPJH-XQKPHYTASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₃₈O₁₉
• Molecular Weight: 726.60 g/mol
• Exact Mass: 726.20072898 g/mol
• Topological Polar Surface Area (TPSA): 287.00 Ų
• XlogP: -2.40
• Atomic LogP (AlogP): -2.59
• H-Bond Acceptor: 19
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5078	50.78%
Caco-2	-	0.8852	88.52%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.5587	55.87%
OATP2B1 inhibitior	-	0.8600	86.00%
OATP1B1 inhibitior	+	0.7638	76.38%
OATP1B3 inhibitior	+	0.9664	96.64%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.5067	50.67%
P-glycoprotein inhibitior	+	0.6753	67.53%
P-glycoprotein substrate	+	0.6424	64.24%
CYP3A4 substrate	+	0.6774	67.74%
CYP2C9 substrate	-	0.6022	60.22%
CYP2D6 substrate	-	0.8738	87.38%
CYP3A4 inhibition	-	0.8029	80.29%
CYP2C9 inhibition	-	0.8378	83.78%
CYP2C19 inhibition	-	0.7455	74.55%
CYP2D6 inhibition	-	0.9033	90.33%
CYP1A2 inhibition	-	0.8335	83.35%
CYP2C8 inhibition	+	0.7635	76.35%
CYP inhibitory promiscuity	-	0.7445	74.45%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6628	66.28%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9161	91.61%
Skin irritation	-	0.8176	81.76%
Skin corrosion	-	0.9493	94.93%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4012	40.12%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8265	82.65%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.7134	71.34%
Acute Oral Toxicity (c)	III	0.5759	57.59%
Estrogen receptor binding	+	0.8100	81.00%
Androgen receptor binding	+	0.6125	61.25%
Thyroid receptor binding	-	0.5055	50.55%
Glucocorticoid receptor binding	+	0.7269	72.69%
Aromatase binding	+	0.5321	53.21%
PPAR gamma	+	0.7581	75.81%
Honey bee toxicity	-	0.7496	74.96%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9602	96.02%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL220	P22303	Acetylcholinesterase	99.68%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.39%	91.11%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	96.15%	95.64%
CHEMBL2581	P07339	Cathepsin D	92.95%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.95%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.11%	99.17%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	90.82%	95.83%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.45%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.12%	86.92%
CHEMBL1951	P21397	Monoamine oxidase A	89.71%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	89.00%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.84%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.19%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.57%	96.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.74%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.28%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.01%	94.45%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.04%	96.90%

Plants that contains it

• Fraxinus ornus

Cross-Links

• PubChem: 163190672
• LOTUS: LTS0248225
• wikiData: Q105341330