Compound ID | 2781

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Xanthocillin X

Class: Natural product antibiotic

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Binds to regulatory heme disrupting their binding to essential hemoproteins
Target Pathogen: Broad-spectrum activity except enterococci; most active against Acinetobacter baumannii; active against methicillin-resistant and -susceptible Staphylococcus aureus
Description: Natural product from Penicillium notatum; shows synergistic effect with gentamicin; has an isocyanide core
Year first mentioned: 1954
Development status: Experimental
Chemical structure(s):
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Molecular weight: 288.3
Iso. SMILES: [C-]#[N+]/C(=C\C1=CC=C(C=C1)O)/C(=C/C2=CC=C(C=C2)O)/[N+]#[C-]
InChI Key: YBMVKDUTYAGKEW-WHYMJUELSA-N
Can. SMILES: [C-]#[N+]/C(=C\C1=CC=C(C=C1)O)/C(=C/C2=CC=C(C=C2)O)/[N+]#[C-]
InChI: InChI=1S/C18H12N2O2/c1-19-17(11-13-3-7-15(21)8-4-13)18(20-2)12-14-5-9-16(22)10-6-14/h3-12,21-22H/b17-11-,18-12-
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5378293
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1993407/?page=1
  • https://pubs.acs.org/doi/10.1021/acscentsci.0c01621

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