Compound ID | 2102

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Tunicamycin

Synonym(s): Tunicamycin A  |  Tunicamycin B2

Class: Natural product antibiotic

Spectrum of activity: Gram-positive
Details of activity: Interferes with cell-wall synthesis by inhibiting transfer of the peptidoglycan precursor moiety (MurNAc-pentapeptide) to the membrane lipid carrier, undecaprenyl phosphate. Tunicamycin inhibits both MraY and its eukaryotic paralog GlcNAc-1-P-transferase (GPT)
Description: Natural compound produced by Streptomyces; antitumor activities in various cancers are explored; a nucleoside antibiotic
Year first mentioned: 1971
Development status: Experimental
Reason Dropped: Cytotoxic, causes premature ovarian failure by producing endoplasmic reticulum stress
Chemical structure(s):
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Molecular weight: 830.92
Iso. SMILES: CC(C)CCCCCCCCC/C=C/C(=O)N[C@@H]1[C@H]([C@H]([C@H](O[C@H]1O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)NC(=O)C)C[C@H]([C@@H]3[C@H]([C@H]([C@@H](O3)N4C=CC(=O)NC4=O)O)O)O)O)O
InChI Key: MEYZYGMYMLNUHJ-DIRMKAHISA-N
Can. SMILES: CC(C)CCCCCCCCC/C=C/C(=O)N[C@@H]1[C@H]([C@H]([C@@H](C[C@H]([C@@H]2[C@H]([C@H]([C@H](N3C=CC(=O)NC3=O)O2)O)O)O)O[C@H]1O[C@@H]4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)NC(=O)C)O)O
InChI: 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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/11104835
Guide to Pharmacology: tunicamycin
Citations:
  • https://jeccr.biomedcentral.com/articles/10.1186/s13046-018-0935-8
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9917250/
  • https://journals.asm.org/doi/epdf/10.1128/AAC.40.7.1640?src=getftr

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