Compound ID | 2767

Update compound information

Tirandamycin

Synonym(s): 3-acyltetramic acid

Class: Natural product antibiotic

Spectrum of activity: Gram-positive
Details of activity: Active against Lactobacillus casei, and Clostridium pasteurianum; RNA synthesis inhibitor, additionally inhibits futalosine pathway
Description: Natural product from Streptomyces tirandis; structurally related to streptolydigin but less potent in vitro; shows cross-resistance to ansamycin resistant Staphylococcus aureus
Institute where first reported: Research Laboratories, The Upjohn Company, Kalamazoo, Michigan 49001 USA
Year first mentioned: 1971
Development status: Experimental
Chemical structure(s):
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Molecular weight: 417.45
Iso. SMILES: C[C@H]1[C@@H]2C(=O)[C@H]3[C@](O3)([C@@](O2)(O[C@@H]1[C@H](C)/C=C(\C)/C=C/C(=C\4/C(=O)CNC4=O)/O)C)C
InChI Key: URGUBECARCAPRI-UYXUTHQNSA-N
Can. SMILES: C/C(=C\[C@@H](C)[C@@H]1[C@@H](C)[C@@H]2C(=O)[C@H]3[C@@](C)([C@](C)(O1)O2)O3)/C=C/C(=C\4/C(=O)CNC4=O)/O
InChI: InChI=1S/C22H27NO7/c1-10(6-7-13(24)15-14(25)9-23-20(15)27)8-11(2)17-12(3)18-16(26)19-21(4,30-19)22(5,28-17)29-18/h6-8,11-12,17-19,24H,9H2,1-5H3,(H,23,27)/b7-6+,10-8+,15-13+/t11-,12-,17-,18-,19+,21+,22-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/54706137
Citations:
  • https://www.nature.com/articles/ja201722
  • https://journals.asm.org/doi/epdf/10.1128/aac.10.4.618

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