Compound ID | 2782

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Xanthomycin A

Synonym(s): Guamecycline

Class: Tetracycline

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Active against Staphylococcus aureus, Corynebacterium xerosis, Escherichia coli, Enterobacter cloacae, Enterobacter aerogenes, Klebsiella pneumoniae, and Salmonella enteritidis ; likely acts as protein synthesis inhibitor
Description: Natural product from Streptomyces sp.; also shows anti-tumour activity
Year first mentioned: 1981
Development status: Experimental
Chemical structure(s):
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Molecular weight: 626.66
Iso. SMILES: C[C@@]1([C@H]2C[C@H]3[C@@H](C(=O)C(=C([C@]3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)NCN5CCN(CC5)C(=N)N=C(N)N)N(C)C)O
InChI Key: FAMUIRDLAWWMCQ-AQFAATAFSA-N
Can. SMILES: C[C@]1(C2=CC=CC(=C2C(=C3[C@@H]1C[C@H]4[C@@H](C(=O)C(=C([C@]4(C3=O)O)O)C(=O)NCN5CCN(CC5)C(=N)N=C(N)N)N(C)C)O)O)O
InChI: InChI=1S/C29H38N8O8/c1-28(44)13-5-4-6-16(38)17(13)21(39)18-14(28)11-15-20(35(2)3)22(40)19(24(42)29(15,45)23(18)41)25(43)33-12-36-7-9-37(10-8-36)27(32)34-26(30)31/h4-6,14-15,20,38-39,42,44-45H,7-12H2,1-3H3,(H,33,43)(H5,30,31,32,34)/t14-,15-,20-,28+,29-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/54688683
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/14186843/
  • https://www.jstage.jst.go.jp/article/antibiotics1968/34/7/34_7_856/_pdf/-char/en

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