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

Details

• Internal ID: 8de7e29b-53e3-4346-8a70-777563d2798a
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Coumarin glycosides
• IUPAC Name: methyl (2S,3R,4S)-3-ethenyl-4-[2-oxo-2-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(6-hydroxy-2-oxochromen-7-yl)oxyoxan-2-yl]methoxy]ethyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
• SMILES (Canonical): COC(=O)C1=COC(C(C1CC(=O)OCC2C(C(C(C(O2)OC3=C(C=C4C=CC(=O)OC4=C3)O)O)O)O)C=C)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@H]([C@@H]([C@@H]1CC(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(C=C4C=CC(=O)OC4=C3)O)O)O)O)C=C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)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)48-18-8-17-12(6-16(18)34)4-5-21(35)47-17/h3-6,8,10,13-14,19-20,23-28,30-34,37-42H,1,7,9,11H2,2H3/t13-,14+,19-,20-,23-,24-,25+,26+,27-,28-,30+,31-,32+/m1/s1
• InChI Key: YNOUJPHGTJKBFJ-BMHXGUHDSA-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: -1.90
• Atomic LogP (AlogP): -2.73
• H-Bond Acceptor: 19
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4822	48.22%
Caco-2	-	0.8858	88.58%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.5501	55.01%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.7717	77.17%
OATP1B3 inhibitior	+	0.9755	97.55%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5808	58.08%
P-glycoprotein inhibitior	+	0.6665	66.65%
P-glycoprotein substrate	+	0.5663	56.63%
CYP3A4 substrate	+	0.6777	67.77%
CYP2C9 substrate	+	0.5911	59.11%
CYP2D6 substrate	-	0.8673	86.73%
CYP3A4 inhibition	-	0.8333	83.33%
CYP2C9 inhibition	-	0.8454	84.54%
CYP2C19 inhibition	-	0.6962	69.62%
CYP2D6 inhibition	-	0.9067	90.67%
CYP1A2 inhibition	-	0.8577	85.77%
CYP2C8 inhibition	+	0.7165	71.65%
CYP inhibitory promiscuity	-	0.7743	77.43%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6763	67.63%
Eye corrosion	-	0.9868	98.68%
Eye irritation	-	0.9124	91.24%
Skin irritation	-	0.8057	80.57%
Skin corrosion	-	0.9399	93.99%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6493	64.93%
Micronuclear	+	0.5659	56.59%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.7985	79.85%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.4825	48.25%
Acute Oral Toxicity (c)	III	0.5512	55.12%
Estrogen receptor binding	+	0.7945	79.45%
Androgen receptor binding	+	0.6035	60.35%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6830	68.30%
Aromatase binding	+	0.5567	55.67%
PPAR gamma	+	0.7098	70.98%
Honey bee toxicity	-	0.7475	74.75%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9740	97.40%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL220	P22303	Acetylcholinesterase	98.92%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.59%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.53%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.89%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.94%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.93%	89.00%
CHEMBL2581	P07339	Cathepsin D	89.89%	98.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	89.40%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	89.11%	94.73%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	88.44%	95.83%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.85%	86.92%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.03%	94.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.15%	96.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	85.31%	95.64%
CHEMBL4208	P20618	Proteasome component C5	84.22%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.20%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.65%	99.23%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.99%	91.24%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	81.94%	83.57%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.31%	94.45%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.86%	96.90%

Plants that contains it

• Fraxinus chinensis

Cross-Links

• PubChem: 163056134
• LOTUS: LTS0134777
• wikiData: Q105351050