Compound ID | 2706

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Quinaldopeptin

Class: Natural product antibiotic

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: DNA synthesis inhibitor. Binds and intercalates into DNA
Target Pathogen: Active against Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus faecalis, Clostridium difficile, Clostridium perfringes, Propionibacterium acnes, Escherichia coli, and Klebsiella pneumoniae
Description: Natural product from Streptoverticillium album strain Q132-6; a cyclic chromopeptide/ quinomycin-type antibiotic; shows antitumor activity towards P338 leukemia
Institute where first reported: Bristol-Myers Research Institute, Ltd., Tokyo Research Center, Japan
Year first mentioned: 1990
Development status: Experimental
Chemical structure(s):
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Molecular weight: 1243.37
Iso. SMILES: C[C@@H]1[C@@H](C(=O)N2CCCCC2C(=O)NCC(=O)N(CC(=O)N3CCCCC3C(=O)N[C@@H](C(C(=O)N4CCCC[C@H]4C(=O)NCC(=O)N(CC(=O)N5CCCCC5C(=O)N1)C)NC(=O)C6=NC7=CC=CC=C7C=C6O)C)C)NC(=O)C8=NC9=CC=CC=C9C=C8O
InChI Key: KIPSHYPQCJYONU-GVPFWXHKSA-N
Can. SMILES: C[C@@H]1C(C(=O)N2CCCC[C@H]2C(=O)NCC(=O)N(C)CC(=O)N3CCCCC3C(=O)N[C@H](C)[C@@H](C(=O)N4CCCCC4C(=O)NCC(=O)N(C)CC(=O)N5CCCCC5C(=O)N1)NC(=O)C6=NC7=C(C=CC=C7)C=C6O)NC(=O)C8=NC9=C(C=CC=C9)C=C8O
InChI: InChI=1S/C62H78N14O14/c1-35-51(69-59(87)53-45(77)29-37-17-5-7-19-39(37)67-53)61(89)75-27-15-11-21-41(75)55(83)63-31-47(79)72(4)34-50(82)74-26-14-10-24-44(74)58(86)66-36(2)52(70-60(88)54-46(78)30-38-18-6-8-20-40(38)68-54)62(90)76-28-16-12-22-42(76)56(84)64-32-48(80)71(3)33-49(81)73-25-13-9-23-43(73)57(85)65-35/h5-8,17-20,29-30,35-36,41-44,51-52,77-78H,9-16,21-28,31-34H2,1-4H3,(H,63,83)(H,64,84)(H,65,85)(H,66,86)(H,69,87)(H,70,88)/t35-,36-,41+,42?,43?,44?,51?,52+/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5466698
Citations:
  • https://www.nature.com/articles/s41598-023-34437-9#Sec7
  • https://www.jstage.jst.go.jp/article/antibiotics1968/43/7/43_7_796/_pdf/-char/en

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