Compound ID | 2748

Update compound information

Streptovaricin

Class: Natural product antibiotic

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Active against methicillin-resistant and -susceptible Staphylococcus aureus, and Mycobacterium tuberculosis; targets DNA-dependent RNA polymerase (RNA synthesis inhibitor)
Propensity to select resistant mutants: Yes, at 2x10^-8 mutation frequency
Description: Natural product from Streptomyces spectabilis; chemically related to rifamycin (ansamycin-type); derivatives reported; when clinically tested against Mycobacterium tuberculosis, it showed better efficacy when in combination with isoniazid than on its own
Year first mentioned: 1957
Development status: Experimental
Chemical structure(s):
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Molecular weight: 769.83
Iso. SMILES: C[C@@H]1/C=C\C=C(\C(=O)NC2=C(C(=C3C(=C2O)C(=O)C(=C4C3=C(/C(=C/[C@@]([C@@H]([C@@H]([C@H]([C@@H]([C@@H]([C@@H](C1O)C)O)C(=O)OC)O)C)O)(C)O)/C)OCO4)C)OC(=O)C)C)/C
InChI Key: JDECNKBYILMOLE-UTNWNAHBSA-N
Can. SMILES: C[C@@H]1/C=C\C=C(/C)\C(=O)NC2=C(C3=C(C4=C(/C(=C/[C@](C)([C@@H]([C@H](C)[C@H]([C@@H]([C@@H]([C@H](C)C1O)O)C(=O)OC)O)O)O)/C)OCOC4=C(C)C3=O)C(=C2C)OC(=O)C)O
InChI: InChI=1S/C40H51NO14/c1-16-12-11-13-17(2)38(49)41-28-19(4)36(55-23(8)42)24-25(33(28)47)31(45)21(6)35-26(24)34(53-15-54-35)18(3)14-40(9,51)37(48)22(7)32(46)27(39(50)52-10)30(44)20(5)29(16)43/h11-14,16,20,22,27,29-30,32,37,43-44,46-48,51H,15H2,1-10H3,(H,41,49)/b12-11-,17-13+,18-14+/t16-,20-,22-,27-,29?,30-,32-,37-,40-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/135538643
Citations:
  • https://www.sciencedirect.com/science/article/pii/0362547877900195?via%3Dihub
  • https://pubmed.ncbi.nlm.nih.gov/28858479/#:~:text=The%20streptovaricins%2C%20chemically%20related%20to,antibacterial%20agents%2C%20particularly%20against%20mycobacteria.

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