Compound ID | 2307

Update compound information

Phenelfamycin B

Class: Natural product antibiotic

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-negative
Mechanism of action: Protein synthesis inhibitor. Targets elongation factor Tu during translation in protein biosynthesis
Target Pathogen: Active against Neisseria gonorrhoeae
Description: Natural product from Streptomyces sulphureus ATCC 27468; elfamycin antibiotic
Year first mentioned: 1988
Development status: Experimental
Chemical structure(s):
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Molecular weight: 938.11
Iso. SMILES: C/C=C\C=C\[C@H]1C([C@H]([C@H]([C@](O1)([C@H](CO[C@H]2C[C@@H]([C@@H]([C@@H](O2)C)O)OC)C(=O)NC/C=C/C=C(\C)/[C@H]([C@@H](C)[C@H]3C[C@@H]([C@@H](O3)/C=C/C=C/C=C/C(=O)O)O)OC)O)O)OC(=O)CC4=CC=CC=C4)(C)C
InChI Key: VLBWFLKRBCOSGD-NMMXFFNGSA-N
Can. SMILES: C/C=C\C=C\[C@H]1C(C)(C)[C@H]([C@H]([C@]([C@H](CO[C@H]2C[C@@H]([C@@H]([C@H](C)O2)O)OC)C(=O)NC/C=C/C=C(\C)/[C@H]([C@@H](C)[C@H]3C[C@@H]([C@H](/C=C/C=C/C=C/C(=O)O)O3)O)OC)(O)O1)O)OC(=O)CC4=CC=CC=C4
InChI: InChI=1S/C51H71NO15/c1-9-10-14-25-41-50(5,6)48(66-43(56)28-35-22-15-13-16-23-35)47(58)51(60,67-41)36(31-63-44-30-40(61-7)45(57)34(4)64-44)49(59)52-27-20-19-21-32(2)46(62-8)33(3)39-29-37(53)38(65-39)24-17-11-12-18-26-42(54)55/h9-26,33-34,36-41,44-48,53,57-58,60H,27-31H2,1-8H3,(H,52,59)(H,54,55)/b10-9-,12-11+,20-19+,24-17+,25-14+,26-18+,32-21+/t33-,34-,36+,37-,38-,39+,40-,41-,44+,45+,46+,47+,48-,51+/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/119057393
Citations:
  • https://www.jstage.jst.go.jp/article/antibiotics1968/41/10/41_10_1300/_article
  • https://pubs.acs.org/doi/10.1021/acsinfecdis.0c00467

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