Compound ID | 2617

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Methylenomycin

Class: Natural product antibiotic

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Active against Staphylococcus aureus, Alcaligenes faecalis, Escherichia coli, Proteus sp., Klebsiella pneumoniae, and Pseudomonas aeruginosa; likely cell wall synthesis inhibitor
Description: Natural product from Streptomyces violaceoruber (methylenomycin A; also by Streptomyces coelicolor) but chemically modified to improve biological activity; analogues with narrow-spectrum activity reported
Institute where first reported: Fermentation Research Laboratories, Sankyo Co., Ltd., Tokyo, Japan
Year first mentioned: 1974
Development status: Experimental
Chemical structure(s):
Methylenomycin A
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Molecular weight: 182.17
Iso. SMILES: C[C@]12[C@@H](C(=C)C(=O)[C@]1(O2)C)C(=O)O
InChI Key: HBECYYFDLZZMPL-WLGLDCGKSA-N
Can. SMILES: C=C1[C@@H](C(=O)O)[C@@]2(C)[C@@](C)(C1=O)O2
InChI: InChI=1S/C9H10O4/c1-4-5(7(11)12)8(2)9(3,13-8)6(4)10/h5H,1H2,2-3H3,(H,11,12)/t5-,8-,9+/m0/s1
Methylenomycin B
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Molecular weight: 122.16
Iso. SMILES: CC1=C(C(=O)C(=C)C1)C
InChI Key: YDXIEAHUYZKJOH-UHFFFAOYSA-N
Can. SMILES: CC1=C(C)C(=O)C(=C)C1
InChI: InChI=1S/C8H10O/c1-5-4-6(2)8(9)7(5)3/h2,4H2,1,3H3
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/10899285
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/3040648
Citations:
  • https://www.jstage.jst.go.jp/article/antibiotics1968/27/6/27_6_393/_pdf/-char/en
  • https://www.jstage.jst.go.jp/article/antibiotics1968/27/6/27_6_400/_pdf

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