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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
Tunicamycin induced endoplasmic reticulum stress promotes apoptosis of prostate cancer cells by activating mTORC1.
2017 Sep 15
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
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ACTIVE MOIETY