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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
Structure of TUNICAMYCIN VII

SMILES

[H][C@@]1(O[C@H]([C@H](O)[C@@H]1O)N2C=CC(=O)NC2=O)[C@H](O)C[C@H]3O[C@@H](O[C@@]4([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4NC(C)=O)[C@H](NC(=O)\C=C\CCCCCCCCCCC(C)C)[C@@H](O)[C@H]3O

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

HIDE SMILES / InChI

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

Description
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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q9H3H5
Gene ID: 1798.0
Gene Symbol: DPAGT1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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
by admin
on Sat Dec 16 09:32:20 GMT 2023
Edited
by admin
on Sat Dec 16 09:32:20 GMT 2023
Record UNII
6SE66719OT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TUNICAMYCIN VII
Common Name English
TUNICAMYCIN B
Common Name English
CORYNETOXIN U-16I
Common Name English
TUNICAMYCIN C1
Common Name English
Code System Code Type Description
CHEBI
64256
Created by admin on Sat Dec 16 09:32:20 GMT 2023 , Edited by admin on Sat Dec 16 09:32:20 GMT 2023
PRIMARY
CAS
66081-36-5
Created by admin on Sat Dec 16 09:32:20 GMT 2023 , Edited by admin on Sat Dec 16 09:32:20 GMT 2023
PRIMARY
FDA UNII
6SE66719OT
Created by admin on Sat Dec 16 09:32:20 GMT 2023 , Edited by admin on Sat Dec 16 09:32:20 GMT 2023
PRIMARY
PUBCHEM
56927836
Created by admin on Sat Dec 16 09:32:20 GMT 2023 , Edited by admin on Sat Dec 16 09:32:20 GMT 2023
PRIMARY
EPA CompTox
DTXSID80511442
Created by admin on Sat Dec 16 09:32:20 GMT 2023 , Edited by admin on Sat Dec 16 09:32:20 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY