Compound ID | 2001

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Rokitamycin

Synonym(s): Rikamycin

Class: Macrolide

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Protein synthesis inhibitor. Binds to the peptidyl transferase component of the bacterial 50S ribosomal subunit, thus inhibiting peptide bond formation
Description: Semisynthetic 16-membered macrolide
Year first mentioned: 1981
Highest development stage: Approved
Development status: Approved
Chemical structure(s):
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Molecular weight: 828
Iso. SMILES: CCCC(=O)O[C@H]1[C@@H](O[C@H](C[C@@]1(C)OC(=O)CC)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2N(C)C)O)O[C@H]3[C@H](C[C@H]([C@H](/C=C/C=C/C[C@H](OC(=O)C[C@H]([C@@H]3OC)O)C)O)C)CC=O)C)C
InChI Key: VYWWNRMSAPEJLS-MDWYKHENSA-N
Can. SMILES: CCCC(=O)O[C@H]1[C@H](C)O[C@H](C[C@@]1(C)OC(=O)CC)O[C@@H]2[C@@H](C)O[C@H]([C@@H]([C@H]2N(C)C)O)O[C@H]3[C@@H](CC=O)C[C@@H](C)[C@H](/C=C/C=C/C[C@@H](C)OC(=O)C[C@H]([C@@H]3OC)O)O
InChI: InChI=1S/C42H69NO15/c1-11-16-32(48)55-40-27(6)53-34(23-42(40,7)58-31(47)12-2)56-37-26(5)54-41(36(50)35(37)43(8)9)57-38-28(19-20-44)21-24(3)29(45)18-15-13-14-17-25(4)52-33(49)22-30(46)39(38)51-10/h13-15,18,20,24-30,34-41,45-46,50H,11-12,16-17,19,21-23H2,1-10H3/b14-13+,18-15+/t24-,25-,26-,27+,28+,29+,30-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5282211
Guide to Pharmacology: rokitamycin
Citations:
  • https://journals.asm.org/doi/10.1128/AAC.39.5.1185
  • https://www.tandfonline.com/doi/abs/10.1080/1120009X.1992.11739129
  • https://www.tandfonline.com/doi/abs/10.1179/joc.2002.14.2.115

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