Compound ID | 3112

Update compound information

Efrotomycin

Synonym(s): FR-02A

Class: Protein synthesis inhibitor

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Protein synthesis inhibitor
Target Pathogen: Active against Streptococcus pyogenes, Corynebacterium diphtheriae, and Yersinia pseudotuberculosis
Description: Natural product from Streptomyces lactamdurans
Institute where first reported: Merck Sharp & Dohme Research Laboratories
Year first mentioned: 1976
Development status: Experimental
Chemical structure(s):
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Molecular weight: 1145.33
Iso. SMILES: CC[C@H](C(=O)NC/C=C/C=C(\C)/[C@H]([C@@H](C)[C@H]1[C@H]([C@H]([C@H](O1)/C=C/C=C/C=C(\C)/C(=O)C2=C(C=CN(C2=O)C)O)O)O)OC)[C@@]3([C@@H]([C@@H](C([C@@H](O3)/C=C/C=C\C)(C)C)O[C@H]4[C@@H]([C@@H]([C@@H]([C@H](O4)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)O)OC)OC)O)O)O
InChI Key: ASOJLQIBBYOFDE-SBHXXGSWSA-N
Can. SMILES: C/C=C\C=C\[C@H]1C(C)(C)[C@H]([C@H]([C@]([C@H](CC)C(=O)NC/C=C/C=C(\C)/[C@H]([C@@H](C)[C@H]2[C@H]([C@H]([C@@H](/C=C/C=C/C=C(\C)/C(=O)C3=C(C=CN(C)C3=O)O)O2)O)O)OC)(O)O1)O)O[C@H]4[C@@H]([C@@H]([C@@H]([C@@H](C)O4)O[C@H]5[C@@H]([C@@H]([C@H]([C@H](C)O5)OC)O)OC)OC)O
InChI: InChI=1S/C59H88N2O20/c1-15-17-19-27-39-58(8,9)53(80-56-45(67)50(74-13)49(35(7)76-56)79-57-51(75-14)44(66)48(73-12)34(6)77-57)52(68)59(71,81-39)36(16-2)54(69)60-29-23-22-25-32(4)46(72-11)33(5)47-43(65)42(64)38(78-47)26-21-18-20-24-31(3)41(63)40-37(62)28-30-61(10)55(40)70/h15,17-28,30,33-36,38-39,42-53,56-57,62,64-68,71H,16,29H2,1-14H3,(H,60,69)/b17-15-,20-18+,23-22+,26-21+,27-19+,31-24+,32-25+/t33-,34+,35-,36-,38-,39+,42+,43+,44-,45-,46-,47+,48+,49-,50+,51-,52-,53+,56+,57+,59-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/135564847
Citations:
  • https://www.jstage.jst.go.jp/article/antibiotics1968/29/10/29_10_1083/_article
  • https://www.jstage.jst.go.jp/article/antibiotics1968/29/10/29_10_1083/_pdf/-char/en
  • https://www.jstage.jst.go.jp/article/antibiotics1968/29/6/29_6_670/_article/-char/en

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