Compound ID | 53

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Tripropeptin C

Class: Antimicrobial peptide

Agent Type: Natural product; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Cell wall synthesis inhibitor. Likely inhibits flippase activity or transglycosylation step also resulting in the inhibition of C55-PP dephosphorylation
Target Pathogen: Active against methicillin resistant Staphylococcus aureus and vancomycin resistant Enterococcus sp.
Description: Natural product from soil bacterium Lysobacter sp. strain BMK333-48F3; a tripropeptin lipodepsipeptide
Institute where first reported: Laboratory of Disease Biology, Institute of Microbial Chemistry, Tokyo, Japan
Year first mentioned: 2001
Development status: Experimental
Chemical structure(s):
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Molecular weight: 1154.27
Iso. SMILES: CC(C)CCCCCCCCCC1CC(=O)NC(C(=O)N2CCCC2C(=O)N3CCCC3C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N4CCC(C4C(=O)NC(C(=O)O1)C(C(=O)O)O)O)CO)C(C(=O)O)O)CCCN=C(N)N)C(C)O
InChI Key: ZRHHHIZQDIARCA-UHFFFAOYSA-N
Can. SMILES: CC(C)CCCCCCCCCC1CC(=O)NC(C(C)O)C(=O)N2CCCC2C(=O)N3CCCC3C(=O)NC(CCCN=C(N)N)C(=O)NC(C(C(=O)O)O)C(=O)NC(CO)C(=O)N4CCC(C4C(=O)NC(C(C(=O)O)O)C(=O)O1)O
InChI: InChI=1S/C51H83N11O19/c1-26(2)14-9-7-5-4-6-8-10-15-28-24-34(66)57-35(27(3)64)47(75)61-22-13-18-32(61)46(74)60-21-12-17-31(60)42(70)55-29(16-11-20-54-51(52)53)41(69)58-36(39(67)48(76)77)43(71)56-30(25-63)45(73)62-23-19-33(65)38(62)44(72)59-37(50(80)81-28)40(68)49(78)79/h26-33,35-40,63-65,67-68H,4-25H2,1-3H3,(H,55,70)(H,56,71)(H,57,66)(H,58,69)(H,59,72)(H,76,77)(H,78,79)(H4,52,53,54)
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/58960776
Citations:
  • https://www.jstage.jst.go.jp/article/antibiotics1968/54/12/54_12_1054/_pdf
  • http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3147643/pdf/zac3821.pdf
  • https://journals.asm.org/doi/10.1128/aac.00443-11
  • https://www.nature.com/articles/s41429-024-00703-9#Sec7

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