Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C39H64N4O16 |
| Molecular Weight | 844.9427 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 15 / 15 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)CCCCCCCCCC\C=C\C(=O)N[C@H]1[C@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2NC(C)=O)O[C@H](C[C@@H](O)[C@H]3O[C@H]([C@H](O)[C@@H]3O)N4C=CC(=O)NC4=O)[C@H](O)[C@@H]1O
InChI
InChIKey=ZOCXUHJGZXXIGQ-NPXWYGMKSA-N
InChI=1S/C39H64N4O16/c1-20(2)14-12-10-8-6-4-5-7-9-11-13-15-25(47)41-28-32(52)29(49)23(56-38(28)59-37-27(40-21(3)45)31(51)30(50)24(19-44)57-37)18-22(46)35-33(53)34(54)36(58-35)43-17-16-26(48)42-39(43)55/h13,15-17,20,22-24,27-38,44,46,49-54H,4-12,14,18-19H2,1-3H3,(H,40,45)(H,41,47)(H,42,48,55)/b15-13+/t22-,23-,24-,27-,28-,29+,30-,31-,32-,33+,34-,35-,36-,37-,38+/m1/s1
| Molecular Formula | C39H64N4O16 |
| Molecular Weight | 844.9427 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 15 / 15 |
| E/Z Centers | 1 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/17827659Curator's Comment: he description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/28978108
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17827659
Curator's Comment: he description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/28978108
Tunicamycin VII is nucleotide sugar analogs produced by several Streptomyces species. In eukaryotes, Tunicamycin VII inhibit UDP-N-acetylglucosamine-dolichol phosphate GlcNAc-1-P transferase (GPT) that catalyzes the first step in protein glycosylation. In bacteria they inhibit UDP-N-acetylmuramoyl-pentapeptide: undecaprenol phosphate MurNAc-pentapeptide-1-P transtransferase (MraY) that catalyzes an early stage in peptidoglycan cell wall assembly. Tunicamycins are substrate analog of GPT and MraY, such that the alphabeta-1'',11'-linked GlcNAc residue of the tunicamycins mimics the transferred GlcNAc-1-phosphate. Tunicamycin VII impairs ALK phosphorylation and disrupts pro-survival signaling and cell viability in various neuroblastoma cell lines. A few studies suggest that tunicamycin may work as a therapeutic drug to cancer cells as it has been shown to sensitize human colon and prostate cancer cells to TRAIL-induced apoptosis.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL3559642 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17827659 |
|||
Target ID: Q9H3H5 Gene ID: 1798.0 Gene Symbol: DPAGT1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17827659 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28978108
PC-3 cells stably expressing LC3-GFP were plated onto 2 well chamber slides (BD) and subjected to treatment with tunicamycin (10 μg/ml) for 24, 48, 72, and 96 h. Cells were fixed in 3.7% formaldehyde (Sigma), examined by confocal microscopy (Olympus FV-1000) and digital images were obtained with CCD camera of the microscope software. More than 5 puncta per cell was considered autophagy. Cells were counted under in each field and 5 different fields were scored for statistical analysis.
| Substance Class |
Chemical
Created
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Edited
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6SE66719OT
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Validated (UNII)
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