Compound ID | 785

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Sorangicin A

Class: Natural product antibiotic

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive, Gram-negative & Antimycobacterial
Mechanism of action: RNA synthesis inhibitor. RNA polymerase inhibitor
Target Pathogen: Broad spectrum activity including Mycobacterium sp.
Description: Natural product from Sorangium cellulosum
Institute where first reported: Ciba-Geigy (Novartis, Switzerland)
Year first mentioned: 1986
Development status: Experimental
Reason dropped: Demonstrates partial cross resistance with rifamycin's due to partial overlap in binding site but has 'potential promise as an antituberculosis agent effective against a subset of rifamycin-resistant bacterial infections'
Chemical structure(s):
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Molecular weight: 807.02
Iso. SMILES: C[C@H]1[C@H]2C/C=C/[C@H]3[C@@H]([C@H]4C[C@@H](O3)[C@H](O4)/C=C/C=C\C=C/C(=O)O[C@H]5C=C[C@H](C/C=C/CC/C=C/[C@@H]([C@@H]([C@H](O2)C[C@@H]1O)O)O)O[C@H]5/C(=C/[C@H](C)CCCCC(=O)O)/C)C
InChI Key: OTABDKFPJQZJRD-QLGZCQHWSA-N
Can. SMILES: C[C@H](CCCCC(=O)O)/C=C(\C)/[C@H]1[C@@H]2C=C[C@H](C/C=C/CC/C=C/[C@@H]([C@@H]([C@H]3C[C@@H]([C@@H](C)[C@@H](C/C=C/[C@H]4[C@H](C)[C@H]5C[C@H]([C@@H](/C=C/C=C\C=C/C(=O)O2)O5)O4)O3)O)O)O)O1
InChI: InChI=1S/C47H66O11/c1-30(17-14-15-23-44(50)51)27-31(2)47-40-26-25-34(54-47)18-10-6-5-7-11-19-35(48)46(53)43-28-36(49)32(3)37(56-43)21-16-22-38-33(4)41-29-42(55-38)39(57-41)20-12-8-9-13-24-45(52)58-40/h6,8-13,16,19-20,22,24-27,30,32-43,46-49,53H,5,7,14-15,17-18,21,23,28-29H2,1-4H3,(H,50,51)/b9-8-,10-6+,19-11+,20-12+,22-16+,24-13-,31-27+/t30-,32-,33+,34+,35+,36+,37-,38+,39-,40+,41-,42-,43-,46+,47+/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/657059
Guide to Pharmacology: sorangicin A
Citations:
  • http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2950656/
  • http://www.ncbi.nlm.nih.gov/pubmed/3104268
  • https://doi.org/10.1016/S0040-4039(00)95117-7

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