Compound ID | 3142

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Heneicomycin

Synonym(s): Antibiotic A21A

Class: Protein synthesis inhibitor

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Active against Staphylococcus aureus, Corynebacterium pseudodiphtheriaticum, Streptococcus pyogenes, Streptococcus faecium, Klebsiella pneumoniae, Escherichia coli, and Haemophilus influenzae; inhibits elongation factor (EF) Tu
Description: Natural product from Streptomyces filipinensis; fails to maintain in sufficient inhibitory concentration as it is rapidly absorbed and eliminated in mice
Institute where first reported: Merck Sharp and Dohme Research Laboratories
Year first mentioned: 1979
Development status: Experimental
Chemical structure(s):
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Molecular weight: 794.97
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[C@@H](C([C@@H](O3)/C=C/C=C/C)(C)C)O)O
InChI Key: VKGDSUWMXCVJEA-ZODLGNRVSA-N
Can. SMILES: C/C=C/C=C/[C@H]1C(C)(C)[C@H](C[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
InChI: InChI=1S/C44H62N2O11/c1-10-12-14-22-34-43(6,7)33(48)26-44(54,57-34)30(11-2)41(52)45-24-18-17-20-28(4)39(55-9)29(5)40-38(51)37(50)32(56-40)21-16-13-15-19-27(3)36(49)35-31(47)23-25-46(8)42(35)53/h10,12-23,25,29-30,32-34,37-40,47-48,50-51,54H,11,24,26H2,1-9H3,(H,45,52)/b12-10+,15-13+,18-17+,21-16+,22-14+,27-19+,28-20+/t29-,30-,32-,33+,34+,37+,38+,39-,40+,44+/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/135612719
Citations:
  • https://www.jstage.jst.go.jp/article/antibiotics1968/32/6/32_6_626/_pdf/-char/en
  • https://link.springer.com/chapter/10.1007/978-3-642-68946-8_5
  • https://www.jstage.jst.go.jp/article/antibiotics1968/32/6/32_6_665/_article/-char/en

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