Compound ID | 1063

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Indanomycin

Synonym(s): X-14547A

Class: Membrane-active agent

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Membrane-active agent
Target Pathogen: Active against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus
Institute where first reported: Hoffman-La Roche Inc
Year first mentioned: 1978
Development status: Experimental
Reason dropped: No clinical activity, however some recent work on optimisation of the antibiotic backbone
Chemical structure(s):
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Molecular weight: 493.68
Iso. SMILES: CC[C@H]1CC[C@@H]2[C@@H]1C=C[C@H]([C@H]2C(=O)C3=CC=CN3)/C=C/C=C(\CC)/[C@H]4[C@H](CC[C@@H](O4)[C@@H](C)C(=O)O)C
InChI Key: BAIPOTOKPGDCHA-MWBHXQFBSA-N
Can. SMILES: CC[C@H]1CC[C@@H]2[C@@H]1C=C[C@@H](/C=C/C=C(\CC)/[C@H]3[C@@H](C)CC[C@H]([C@@H](C)C(=O)O)O3)[C@H]2C(=O)C4=CC=CN4
InChI: InChI=1S/C31H43NO4/c1-5-21-13-16-25-24(21)15-14-23(28(25)29(33)26-11-8-18-32-26)10-7-9-22(6-2)30-19(3)12-17-27(36-30)20(4)31(34)35/h7-11,14-15,18-21,23-25,27-28,30,32H,5-6,12-13,16-17H2,1-4H3,(H,34,35)/b10-7+,22-9+/t19-,20+,21-,23+,24+,25+,27+,28+,30+/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/10345604
Guide to Pharmacology: indanomycin
Citations:
  • http://pubs.acs.org/doi/abs/10.1021/jo00193a014
  • https://doi.org/10.1021/ol802422n

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