Compound ID | 784

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Oxydifficidin

Class: Protein synthesis inhibitor

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Broad Spectrum against Aerobic and Anaerobic bacteria (2)
Description: macrocyclic polyene lactone phosphate ester
Institute where first reported: Merck & Co., USA
Year first mentioned: 1986
Highest developmental phase: Preclinical
Development status: Inactive
Reason Dropped: Un-unstable at different pH's and easily oxidated (1). Additionally, little in vivo activity in mice model when administered subcutaneously but was effective through intraperitoneal injection suggesting metabolism of compound and hence preventing its transloction to site of infection (2).
Chemical structure(s):
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Molecular weight: 560.66
Iso. SMILES: CC1C(/C=C\C=C/C=C\CCCC(/C(=C\C=C/CC(OC(=O)CC1=C)CC/C(=C/C=C)/C)/C)OP(=O)(O)O)O
InChI Key: DRXGPYFQEKBQBQ-MUPVVFKXSA-N
Can. SMILES: C=C/C=C(\C)/CCC1C/C=C\C=C(\C)/C(CCC/C=C\C=C/C=C\C(C(C)C(=C)CC(=O)O1)O)OP(=O)(O)O
InChI: InChI=1S/C31H45O7P/c1-6-16-24(2)21-22-28-18-15-14-17-25(3)30(38-39(34,35)36)20-13-11-9-7-8-10-12-19-29(32)27(5)26(4)23-31(33)37-28/h6-10,12,14-17,19,27-30,32H,1,4,11,13,18,20-23H2,2-3,5H3,(H2,34,35,36)/b9-7-,10-8-,15-14-,19-12-,24-16+,25-17-
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/6444091
Citations:
  • https://www.jstage.jst.go.jp/article/antibiotics1968/40/12/40_12_1682/_pdf
  • http://www.ncbi.nlm.nih.gov/pubmed/3123448

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