Compound ID | 2734

Update compound information

Showdomycin

Synonym(s): MSD-125A

Class: Nucleoside analogue

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: DNA synthesis inhibitor
Target Pathogen: Active against Streptococcus haemolyticus and Streptococcus pyogenes
Description: Natural product from Streptomyces showdoensis; nucleoside derivative of maleimide
Institute where first reported: Shionogi Research Laboratory, Shionogi & Co., Ltd. Osaka Japan; Merck, Sharp and Dohme Research Laboratories
Year first mentioned: 1964
Development status: Experimental
Chemical structure(s):
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Molecular weight: 229.19
Iso. SMILES: C1=C(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
InChI Key: FFLUMYXAPXARJP-JBBNEOJLSA-N
Can. SMILES: C1=C([C@H]2[C@@H]([C@@H]([C@@H](CO)O2)O)O)C(=O)NC1=O
InChI: InChI=1S/C9H11NO6/c11-2-4-6(13)7(14)8(16-4)3-1-5(12)10-9(3)15/h1,4,6-8,11,13-14H,2H2,(H,10,12,15)/t4-,6-,7-,8+/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/28032
Citations:
  • https://academic.oup.com/bbb/article-abstract/32/8/1021/5977715
  • https://www.jstage.jst.go.jp/article/antibiotics1968/21/4/21_4_250/_pdf/-char/en
  • https://www.jstage.jst.go.jp/article/bbb1961/35/9/35_9_1328/_pdf
  • https://www.pnas.org/doi/epdf/10.1073/pnas.57.3.548

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