Compound ID | 3122

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Cinodine

Synonym(s): LL-BM123

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. Targets DNA gyrase
Target Pathogen: Active against Staphylococcus aureus, Escherichia coli, Proteus sp., Salmonella sp., Serratia , and Klebsiella pneumoniae
Description: Natural product from Nocardia; glycocinnamoylspermidine
Institute where first reported: Lederle Laboratories A Division of American Cyanamid Company
Year first mentioned: 1977
Development status: Experimental
Chemical structure(s):
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Molecular weight: 893.95
Iso. SMILES: C[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OC2=CC=C(C=C2)/C=C/C(=O)NCCCNCCCCN)N=C(N)N)O)NC(=O)N[C@@H]3[C@@H]([C@H]([C@@H](CO3)O[C@H]4[C@H]5[C@H]([C@@H](CO4)O)NC(=O)N5C(=O)N)O)NC(=O)N
InChI Key: DNVZVPOGAWMZMI-FWDCAGJFSA-N
Can. SMILES: C[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OC2=CC=C(C=C2)/C=C/C(=O)NCCCNCCCCN)N=C(N)N)O)NC(=O)N[C@@H]3[C@@H]([C@H]([C@@H](CO3)O[C@H]4[C@H]5[C@H]([C@@H](CO4)O)NC(=O)N5C(=O)N)O)NC(=O)N
InChI: InChI=1S/C37H59N13O13/c1-17-23(29(54)26(45-33(39)40)31(61-17)62-19-8-5-18(6-9-19)7-10-22(52)44-14-4-13-43-12-3-2-11-38)47-36(57)49-30-25(46-34(41)55)28(53)21(16-59-30)63-32-27-24(20(51)15-60-32)48-37(58)50(27)35(42)56/h5-10,17,20-21,23-32,43,51,53-54H,2-4,11-16,38H2,1H3,(H2,42,56)(H,44,52)(H,48,58)(H4,39,40,45)(H3,41,46,55)(H2,47,49,57)/b10-7+/t17-,20-,21-,23-,24+,25-,26-,27-,28+,29+,30+,31-,32+/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/Cinodine-I
Citations:
  • https://journals.asm.org/doi/pdf/10.1128/aac.20.4.425
  • https://www.jstage.jst.go.jp/article/antibiotics1968/31/5/31_5_398/_article
  • https://www.jstage.jst.go.jp/article/antibiotics1968/30/8/30_8_678/_article/-char/en

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