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

Top
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

Top
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

Top
There are no found synonyms.

2D Structure

Top
2D Structure of 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

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
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

Top

Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
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

Top
Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Osmanthus heterophyllus

Cross-Links

Top
PubChem 102031348
LOTUS LTS0179264
wikiData Q105173758