Compound ID | 2099

Update compound information

Streptolydigin

Synonym(s): Portamycin  |  afragilimycin

Class: RNA polymerase inhibitor

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: RNA synthesis inhibitor. DNA-dependent RNA polymerase inhibitor; inhibits translocation step, thus inhibiting bacterial RNA chain elongation; partial cross-resistance with rifampicin, microcin, CBR703, and sorangicin
Description: Natural compound produced by Streptomyces.
Year first mentioned: 1955
Development status: Experimental
Chemical structure(s):
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Molecular weight: 600.7
Iso. SMILES: C[C@H]1[C@H]2C=C[C@@]3(CO3)[C@](O2)(O[C@@H]1[C@H](C)/C=C(\C)/C=C/C(=C\4/C(=O)[C@@H](N(C4=O)[C@@H]5CC[C@@H]([C@@H](O5)C)O)[C@H](C)C(=O)NC)/O)C
InChI Key: KVTPRMVXYZKLIG-NCAOFHFGSA-N
Can. SMILES: C/C(=C\[C@@H](C)[C@@H]1[C@@H](C)[C@H]2C=C[C@@]3(CO3)[C@](C)(O2)O1)/C=C/C(=C\4/C(=O)[C@H]([C@H](C)C(=O)NC)N([C@@H]5CC[C@@H]([C@H](C)O5)O)C4=O)/O
InChI: InChI=1S/C32H44N2O9/c1-16(14-17(2)28-18(3)23-12-13-32(15-40-32)31(6,42-23)43-28)8-9-22(36)25-27(37)26(19(4)29(38)33-7)34(30(25)39)24-11-10-21(35)20(5)41-24/h8-9,12-14,17-21,23-24,26,28,35-36H,10-11,15H2,1-7H3,(H,33,38)/b9-8+,16-14+,25-22+/t17-,18+,19+,20+,21+,23-,24+,26+,28-,31-,32-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/54708748
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2754413/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3957892/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC249980/

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