Compound ID | 783

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Difficidin

Class: Natural product antibiotic

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Protein synthesis inhibitor
Target Pathogen: Broad spectrum activity including anaerobes
Description: Natural product from Bacillus subtilis ATCC 39320; a macrocyclic polyene lactone phosphate ester
Institute where first reported: Merck & Co., USA
Year first mentioned: 1986
Development status: Experimental
Reason dropped: Shows to be unstable at different pH's and easily oxidated; little in vivo activity in mice model when administered subcutaneously but was effective through intraperitoneal injection suggesting metabolism of compound and hence preventing its translocation to site of infection
Chemical structure(s):
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Molecular weight: 544.66
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
InChI Key: ZUWUQYGHRURWCL-XUIVTPDHSA-N
Can. SMILES: C=C/C=C(\C)/CCC1C/C=C/C=C(\C)/C(CCC/C=C\C=C/C=C/CC(C)C(=C)CC(=O)O1)OP(=O)(O)O
InChI: InChI=1S/C31H45O6P/c1-6-17-25(2)22-23-29-20-16-15-19-27(4)30(37-38(33,34)35)21-14-12-10-8-7-9-11-13-18-26(3)28(5)24-31(32)36-29/h6-11,13,15-17,19,26,29-30H,1,5,12,14,18,20-24H2,2-4H3,(H2,33,34,35)/b9-7-,10-8-,13-11+,16-15+,25-17+,27-19+
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/6438594
Guide to Pharmacology: difficidin
Citations:
  • https://doi.org/10.7164/antibiotics.40.1692
  • https://doi.org/10.7164/antibiotics.40.1682
  • https://doi.org/10.7164/antibiotics.40.1677

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