U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C38H62N4O16
Molecular Weight 830.9161
Optical Activity UNSPECIFIED
Defined Stereocenters 15 / 15
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of TUNICAMYCIN V

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\CCCCCCCCCC(C)C)[C@@H](O)[C@H]3O

InChI

InChIKey=MEYZYGMYMLNUHJ-DIRMKAHISA-N
InChI=1S/C38H62N4O16/c1-19(2)13-11-9-7-5-4-6-8-10-12-14-24(46)40-27-31(51)28(48)22(55-37(27)58-36-26(39-20(3)44)30(50)29(49)23(18-43)56-36)17-21(45)34-32(52)33(53)35(57-34)42-16-15-25(47)41-38(42)54/h12,14-16,19,21-23,26-37,43,45,48-53H,4-11,13,17-18H2,1-3H3,(H,39,44)(H,40,46)(H,41,47,54)/b14-12+/t21-,22-,23-,26-,27-,28+,29-,30-,31-,32+,33-,34-,35-,36-,37+/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/6293705

Tunicamycin V is nucleotide sugar analogs, with a modified fatty acid side-chain, produced by several Streptomyces species. In eukaryotes, Tunicamycin V inhibit transfer of N-acetylglucosamine to a lipid intermediate. 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: transfer of N-acetylglucosamine to a lipid intermediate
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Antifungal activity of microbial secondary metabolites.
2011
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
The selective cytotoxicity of tunicamycin homologues against SV40-transformed 3T3 cells (SV40-3T3) was examined. Incubation of 3T3 or virally transformed 3T3 cells with four different homologues (A1, A2, B1, and B2 at 0.1 to 0.25 microgram/ml) caused detachment and death of transformed cells after 1 to 3 days, while the nontransformed cells were almost unaffected.
Name Type Language
TUNICAMYCIN V
Common Name English
TUNICAMYCIN B1
Common Name English
TUNICAMYCIN A
Common Name English
(+)-TUNICAMYCIN V
Common Name English
Code System Code Type Description
CAS
66054-36-2
Created by admin on Sat Dec 16 08:33:52 GMT 2023 , Edited by admin on Sat Dec 16 08:33:52 GMT 2023
PRIMARY
PUBCHEM
11104835
Created by admin on Sat Dec 16 08:33:52 GMT 2023 , Edited by admin on Sat Dec 16 08:33:52 GMT 2023
PRIMARY
FDA UNII
17RV2Q5O9O
Created by admin on Sat Dec 16 08:33:52 GMT 2023 , Edited by admin on Sat Dec 16 08:33:52 GMT 2023
PRIMARY
CHEBI
64250
Created by admin on Sat Dec 16 08:33:52 GMT 2023 , Edited by admin on Sat Dec 16 08:33:52 GMT 2023
PRIMARY