methyl (4S,5E,6S)-5-(2-acetyloxyethylidene)-6-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-4H-pyran-3-carboxylate

Details

• Internal ID: d2164be5-defe-4d2f-bedd-57ecf218fb62
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (4S,5E,6S)-5-(2-acetyloxyethylidene)-6-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-4H-pyran-3-carboxylate
• SMILES (Canonical): CC(=O)OCC=C1C(C(=COC1OC2C(C(C(C(O2)CO)O)OC3C(C(C(C(O3)CO)O)O)O)O)C(=O)OC)CC(=O)OCCC4=CC(=C(C=C4)O)O
• SMILES (Isomeric): CC(=O)OC/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[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)C(=O)OC)CC(=O)OCCC4=CC(=C(C=C4)O)O
• InChI: InChI=1S/C33H44O20/c1-14(36)47-8-6-16-17(10-23(39)48-7-5-15-3-4-19(37)20(38)9-15)18(30(45)46-2)13-49-31(16)53-33-28(44)29(25(41)22(12-35)51-33)52-32-27(43)26(42)24(40)21(11-34)50-32/h3-4,6,9,13,17,21-22,24-29,31-35,37-38,40-44H,5,7-8,10-12H2,1-2H3/b16-6+/t17-,21+,22+,24+,25+,26-,27+,28+,29-,31-,32-,33-/m0/s1
• InChI Key: MWSTWRUGKQUDPT-MEWUBMMGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₄O₂₀
• Molecular Weight: 760.70 g/mol
• Exact Mass: 760.24259379 g/mol
• Topological Polar Surface Area (TPSA): 307.00 Ų
• XlogP: -2.70
• Atomic LogP (AlogP): -3.27
• H-Bond Acceptor: 20
• H-Bond Donor: 9
• Rotatable Bonds: 14

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5390	53.90%
Caco-2	-	0.8863	88.63%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7978	79.78%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7770	77.70%
OATP1B3 inhibitior	+	0.9321	93.21%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.8376	83.76%
P-glycoprotein inhibitior	+	0.6681	66.81%
P-glycoprotein substrate	+	0.5976	59.76%
CYP3A4 substrate	+	0.6990	69.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8751	87.51%
CYP3A4 inhibition	-	0.8861	88.61%
CYP2C9 inhibition	-	0.8492	84.92%
CYP2C19 inhibition	-	0.7508	75.08%
CYP2D6 inhibition	-	0.8754	87.54%
CYP1A2 inhibition	-	0.7133	71.33%
CYP2C8 inhibition	+	0.7968	79.68%
CYP inhibitory promiscuity	-	0.8849	88.49%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7732	77.32%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9123	91.23%
Skin irritation	-	0.8233	82.33%
Skin corrosion	-	0.9576	95.76%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6633	66.33%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.8453	84.53%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.6167	61.67%
Acute Oral Toxicity (c)	III	0.5941	59.41%
Estrogen receptor binding	+	0.7898	78.98%
Androgen receptor binding	+	0.6951	69.51%
Thyroid receptor binding	-	0.5312	53.12%
Glucocorticoid receptor binding	+	0.6159	61.59%
Aromatase binding	+	0.5505	55.05%
PPAR gamma	+	0.7237	72.37%
Honey bee toxicity	-	0.6665	66.65%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9560	95.60%

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	99.40%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.84%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.87%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.47%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.19%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	93.35%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.35%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.65%	86.92%
CHEMBL2581	P07339	Cathepsin D	89.79%	98.95%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	87.86%	96.90%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.57%	96.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	85.32%	95.64%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.10%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.06%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	83.30%	91.19%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.16%	94.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.11%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.28%	94.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.13%	94.80%

Plants that contains it

• Osmanthus heterophyllus

Cross-Links

• PubChem: 102031348
• LOTUS: LTS0179264
• wikiData: Q105173758