methyl (5E,6S)-4-[2-[2-[3-acetyloxy-4-[(3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyphenyl]ethoxy]-2-oxoethyl]-5-ethylidene-6-[(3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate

Details

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Internal ID 9944cad6-be60-4fe9-9b55-4eb567fdc27b
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
IUPAC Name methyl (5E,6S)-4-[2-[2-[3-acetyloxy-4-[(3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyphenyl]ethoxy]-2-oxoethyl]-5-ethylidene-6-[(3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
SMILES (Canonical) CC=C1C(C(=COC1OC2C(C(C(C(O2)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC)CC(=O)OCCC3=CC(=C(C=C3)OC4C(C(C(C(O4)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
SMILES (Isomeric) C/C=C\1/[C@@H](OC=C(C1CC(=O)OCCC2=CC(=C(C=C2)OC3[C@@H]([C@H]([C@@H]([C@H](O3)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC)OC4[C@@H]([C@H]([C@@H]([C@H](O4)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
InChI InChI=1S/C49H60O27/c1-12-32-33(34(46(60)61-11)19-65-47(32)76-49-45(72-30(10)58)43(70-28(8)56)41(68-26(6)54)38(75-49)21-64-23(3)51)18-39(59)62-16-15-31-13-14-35(36(17-31)66-24(4)52)73-48-44(71-29(9)57)42(69-27(7)55)40(67-25(5)53)37(74-48)20-63-22(2)50/h12-14,17,19,33,37-38,40-45,47-49H,15-16,18,20-21H2,1-11H3/b32-12+/t33?,37-,38-,40-,41-,42+,43+,44-,45-,47+,48?,49?/m1/s1
InChI Key WILIFRSPMCBMKB-RURJUHLQSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C49H60O27
Molecular Weight 1081.00 g/mol
Exact Mass 1080.33219663 g/mol
Topological Polar Surface Area (TPSA) 335.00 Ų
XlogP 1.30
Atomic LogP (AlogP) 1.63
H-Bond Acceptor 27
H-Bond Donor 0
Rotatable Bonds 21

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (5E,6S)-4-[2-[2-[3-acetyloxy-4-[(3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyphenyl]ethoxy]-2-oxoethyl]-5-ethylidene-6-[(3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9503 95.03%
Caco-2 - 0.8526 85.26%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability - 0.7571 75.71%
Subcellular localzation Mitochondria 0.8778 87.78%
OATP2B1 inhibitior + 0.5698 56.98%
OATP1B1 inhibitior + 0.7495 74.95%
OATP1B3 inhibitior + 0.9274 92.74%
MATE1 inhibitior - 0.8400 84.00%
OCT2 inhibitior - 0.7500 75.00%
BSEP inhibitior + 0.9934 99.34%
P-glycoprotein inhibitior + 0.7690 76.90%
P-glycoprotein substrate + 0.6614 66.14%
CYP3A4 substrate + 0.7111 71.11%
CYP2C9 substrate + 0.6064 60.64%
CYP2D6 substrate - 0.8867 88.67%
CYP3A4 inhibition - 0.6456 64.56%
CYP2C9 inhibition - 0.8852 88.52%
CYP2C19 inhibition + 0.6593 65.93%
CYP2D6 inhibition - 0.9191 91.91%
CYP1A2 inhibition - 0.5134 51.34%
CYP2C8 inhibition + 0.8676 86.76%
CYP inhibitory promiscuity - 0.5412 54.12%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9328 93.28%
Carcinogenicity (trinary) Non-required 0.7001 70.01%
Eye corrosion - 0.9871 98.71%
Eye irritation - 0.8995 89.95%
Skin irritation - 0.8516 85.16%
Skin corrosion - 0.9754 97.54%
Ames mutagenesis - 0.5300 53.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7756 77.56%
Micronuclear - 0.7600 76.00%
Hepatotoxicity - 0.7216 72.16%
skin sensitisation - 0.8278 82.78%
Respiratory toxicity + 0.5222 52.22%
Reproductive toxicity + 0.6889 68.89%
Mitochondrial toxicity - 0.6625 66.25%
Nephrotoxicity - 0.6929 69.29%
Acute Oral Toxicity (c) III 0.5178 51.78%
Estrogen receptor binding + 0.8052 80.52%
Androgen receptor binding + 0.7001 70.01%
Thyroid receptor binding + 0.5970 59.70%
Glucocorticoid receptor binding + 0.7628 76.28%
Aromatase binding + 0.6613 66.13%
PPAR gamma + 0.7519 75.19%
Honey bee toxicity - 0.6593 65.93%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5700 57.00%
Fish aquatic toxicity + 0.9815 98.15%

Targets

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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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.99% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.07% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 95.47% 86.33%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 95.25% 86.92%
CHEMBL2581 P07339 Cathepsin D 93.65% 98.95%
CHEMBL3060 Q9Y345 Glycine transporter 2 93.01% 99.17%
CHEMBL3401 O75469 Pregnane X receptor 92.73% 94.73%
CHEMBL1951 P21397 Monoamine oxidase A 91.86% 91.49%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 91.18% 95.17%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 89.18% 91.11%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 88.77% 96.90%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.64% 95.89%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 87.14% 94.00%
CHEMBL2815 P04629 Nerve growth factor receptor Trk-A 84.75% 87.16%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.02% 89.00%
CHEMBL340 P08684 Cytochrome P450 3A4 83.41% 91.19%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 83.11% 92.62%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 82.76% 95.89%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 82.27% 94.80%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 81.23% 94.33%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 80.19% 89.67%

Plants that contains it

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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.
Achillea clypeolata
Achillea crithmifolia
Artemisia gmelinii
Artemisia tripartita
Artemisia xerophytica
Fraxinus angustifolia
Schistostephium rotundifolium
Tanacetum santolina

Cross-Links

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PubChem 163010818
LOTUS LTS0265706
wikiData Q104914225