Compound ID | 1818

Update compound information

Darobactin

Class: BamA inhibitor (bicyclic heptapeptide antibiotic)

Spectrum of activity: Gram-negative
Details of activity: Binds to the main component (BamA) of the β-barrel folding complex (BAM) that is required for the folding and insertion of β-barrel proteins into the outer membrane of Gram-negative bacteria.
Description: Photorhabdus natural compound
Institute where first reported: Northeastern University, Boston, MA, USA
Year first mentioned: 2019
Highest developmental phase: Preclinical
Development status: Experimental
Chemical structure(s):
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Molecular weight: 966.01
Iso. SMILES: C1[C@@H](C(=O)N[C@H](C(=O)NC2[C@@H](C3=CNC4=C3C=CC(=C4)[C@@H]([C@H](NC(=O)[C@@H](NC2=O)CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC5=CC=CC=C5)C(=O)O)CCCN)OC6=CC=CC7=C6NC=C71)CC(=O)N)N
InChI Key: HRMCRRLPTVSYHJ-CPGNCTABSA-N
Can. SMILES: C1=CC=C(C=C1)C[C@@H](C(=O)O)NC(=O)[C@H](CO)NC(=O)[C@@H]2[C@@H](CCCN)C3=CC4=C(C=C3)C(=CN4)[C@@H]5C(C(=O)N[C@@H](CO)C(=O)N2)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CC6=CNC7=C6C=CC=C7O5)N
InChI: InChI=1S/C47H55N11O12/c48-13-5-9-25-23-11-12-27-28(19-51-30(27)16-23)40-39(58-42(63)31(17-36(50)61)53-41(62)29(49)15-24-18-52-37-26(24)8-4-10-35(37)70-40)46(67)56-34(21-60)44(65)57-38(25)45(66)55-33(20-59)43(64)54-32(47(68)69)14-22-6-2-1-3-7-22/h1-4,6-8,10-12,16,18-19,25,29,31-34,38-40,51-52,59-60H,5,9,13-15,17,20-21,48-49H2,(H2,50,61)(H,53,62)(H,54,64)(H,55,66)(H,56,67)(H,57,65)(H,58,63)(H,68,69)/t25-,29-,31-,32-,33-,34-,38-,39?,40+/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/154586077
Citations:
  • https://pubs.rsc.org/en/content/articlelanding/2021/sc/d1sc02725e
  • https://www.nature.com/articles/s41586-021-03455-w
  • https://www.nature.com/articles/s41586-019-1791-1

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