Compound ID | 389

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Tirandalydigin

Class: Natural product antibiotic

Agent Type: Natural product; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: RNA synthesis inhibitor. Bacterial DNA-directed RNA polymerase inhibitor
Target Pathogen: Active against Streptococcus sp. and Enterococcus faecalis
Description: Natural product from Streptomyces tirandis subsp. umidus; tetramic acid-type antibiotic; structural hybrid of tirandamyicn and streptolydigin
Institute where first reported: Abbott Laboratories, USA
Year first mentioned: 1987
Development status: Experimental
Chemical structure(s):
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Molecular weight: 401.45
Iso. SMILES: C[C@H]1[C@H]2C=CC3(CO3)[C@](O2)(O[C@@H]1[C@H](C)/C=C(\C)/C=C/C(=C/4\C(=O)CNC4=O)/O)C
InChI Key: LTYHWFXVSQHTQH-BWPJEIAHSA-N
Can. SMILES: C/C(=C\[C@@H](C)[C@@H]1[C@@H](C)[C@H]2C=CC3(CO3)[C@](C)(O2)O1)/C=C/C(=C/4\C(=O)CNC4=O)/O
InChI: InChI=1S/C22H27NO6/c1-12(5-6-15(24)18-16(25)10-23-20(18)26)9-13(2)19-14(3)17-7-8-22(11-27-22)21(4,28-17)29-19/h5-9,13-14,17,19,24H,10-11H2,1-4H3,(H,23,26)/b6-5+,12-9+,18-15-/t13-,14+,17-,19-,21-,22?/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/54717174
Guide to Pharmacology: tirandalydigin
Citations:
  • https://doi.org/10.7164/antibiotics.41.36
  • http://www.ncbi.nlm.nih.gov/pubmed/1517158

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