Compound ID | 2747

Update compound information

Streptothricin

Class: Streptothricin

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Protein synthesis inhibitor
Target Pathogen: Broad-spectrum activity including Mycobacterium tuberculosis
Description: Natural product from soil Actinomyces; shows delayed nephrotoxicity (~48 h after administration in mouse); small clinical trial in humans performed by Merck showed nephrotoxicity is reversible
Year first mentioned: 1942
Development status: Inactive
Reason dropped: Showed nephrotoxicity in human trials
Chemical structure(s):
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Molecular weight: 502.52
Iso. SMILES: C1[C@H]([C@@H]2[C@@H](C(=O)N1)N=C(N2)NC3C(C(C(C(O3)CO)OC(=O)N)O)NC(=O)CC(CCCN)N)O
InChI Key: NRAUADCLPJTGSF-WJPMJIHPSA-N
Can. SMILES: C(CC(CC(=O)NC1C(C(C(CO)OC1NC2=N[C@H]3[C@@H]([C@@H](CNC3=O)O)N2)OC(=O)N)O)N)CN
InChI: InChI=1S/C19H34N8O8/c20-3-1-2-7(21)4-10(30)24-13-14(31)15(35-18(22)33)9(6-28)34-17(13)27-19-25-11-8(29)5-23-16(32)12(11)26-19/h7-9,11-15,17,28-29,31H,1-6,20-21H2,(H2,22,33)(H,23,32)(H,24,30)(H2,25,26,27)/t7?,8-,9?,11-,12+,13?,14?,15?,17?/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/475825
Citations:
  • https://doi.org/10.3181/00379727-49-13515
  • https://journals.asm.org/doi/10.1128/jb.52.3.399-404.1946
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10187937/

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