Compound ID | 1775

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NOSO-502

Class: Protein synthesis inhibitor

Agent Type: Semisynthetic; Direct acting;
Spectrum of activity: Gram-negative
Mechanism of action: Protein synthesis inhibitor. Binds to bacterial ribosomes
Target Pathogen: Active against Enterobacteriaceae
Description: Semisynthetic, derived from Xenorhabdus; an odilorhabdin-type antibiotic
Institute where first reported: Nosopharm
Year first mentioned: 2015
Highest development stage: Phase 1
Development status: Active
Chemical structure(s):
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Molecular weight: 1078.25
Iso. SMILES: C1C[C@H](N(C1)C(=O)[C@@H](CCCN)NC(=O)CNC(=O)[C@H](CCN)NC(=O)[C@H]([C@H](CN)O)NC(=O)[C@H](CCCCN)N)C(=O)N[C@@H](CC2=CC=CC=C2F)C(=O)N[C@@H](CCCCN)C(=O)N/C(=C\CCN=C(N)N)/C(=O)O
InChI Key: JJUNUSUNICLAGV-URDXWPNVSA-N
Can. SMILES: C1=CC(=C(C=C1)F)C[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N/C(=C\CCN=C(N)N)/C(=O)O)NC(=O)[C@@H]2CCCN2C(=O)[C@@H](CCCN)NC(=O)CNC(=O)[C@H](CCN)NC(=O)[C@H]([C@H](CN)O)NC(=O)[C@H](CCCCN)N
InChI: InChI=1S/C47H80FN17O11/c48-28-11-2-1-10-27(28)24-34(42(71)60-30(13-4-6-19-50)41(70)62-33(46(75)76)15-8-22-57-47(55)56)63-43(72)35-16-9-23-65(35)45(74)32(14-7-20-51)59-37(67)26-58-40(69)31(17-21-52)61-44(73)38(36(66)25-53)64-39(68)29(54)12-3-5-18-49/h1-2,10-11,15,29-32,34-36,38,66H,3-9,12-14,16-26,49-54H2,(H,58,69)(H,59,67)(H,60,71)(H,61,73)(H,62,70)(H,63,72)(H,64,68)(H,75,76)(H4,55,56,57)/b33-15-/t29-,30-,31-,32+,34-,35-,36-,38-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/121246383
Guide to Pharmacology: NOSO-502
Citations:
  • https://eacademy.escmid.org/escmid/2021/eccmid-2021/328129/sanne.van.den.berg.pharmacokinetics.and.pharmacodynamics.of.the.odilorhabdin.html?f=menu%3D6%2Abrowseby%3D8%2Asortby%3D2%2Amedia%3D3%2Ace_id%3D2029%2Alabel%3D22174%2Amarker%3D1353
  • https://hal.archives-ouvertes.fr/hal-03245424
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6125496/
  • https://www.nature.com/articles/d43747-021-00152-5
    • Patent: US10626144B2

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