Corallopyronin A   Click here for help

GtoPdb Ligand ID: 11029

Synonyms: CorA | LS-54950 | LS54950
Comment: Corallopyronin A is a polyketide-peptide antibiotic produced by myxobacterium Corallococcus coralloides B035 [1-2,5]. It has potent anti-filarial activity [3-4].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 16
Topological polar surface area 126.07
Molecular weight 527.29
XLogP 5.42
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES C/C=C/C/C=C(/C(CC/C(=C/C=C(/C(=O)c1c(O)cc(oc1=O)C(CC/C=C/NC(=O)OC)C)\C)/C)O)\C
Isomeric SMILES C/C=C/C/C=C(/C(CC/C(=C/C=C(/C(=O)c1c(O)cc(oc1=O)C(CC/C=C/NC(=O)OC)C)\C)/C)O)\C
InChI InChI=1S/C30H41NO7/c1-7-8-9-12-21(3)24(32)17-15-20(2)14-16-23(5)28(34)27-25(33)19-26(38-29(27)35)22(4)13-10-11-18-31-30(36)37-6/h7-8,11-12,14,16,18-19,22,24,32-33H,9-10,13,15,17H2,1-6H3,(H,31,36)/b8-7+,18-11+,20-14+,21-12+,23-16+
InChI Key FPBHSTHTCPCNBS-QXMYDWGFSA-N
References
1. Bouhired S, Rupp O, Blom J, Schäberle TF, Schiefer A, Kehraus S, Pfarr K, Goesmann A, Hoerauf A, König G. (2019)
Complete Genome Sequence of the Corallopyronin A-Producing Myxobacterium Corallococcus coralloides B035.
Microbiol Resour Announc, 8 (17). [PMID:31023790]
2. Charousová I, Steinmetz H, Medo J, Javoreková S, Wink J. (2017)
Soil myxobacteria as a potential source of polyketide-peptide substances.
Folia Microbiol (Praha), 62 (4): 305-315. [PMID:28161814]
3. Pogorevc D, Panter F, Schillinger C, Jansen R, Wenzel SC, Müller R. (2019)
Production optimization and biosynthesis revision of corallopyronin A, a potent anti-filarial antibiotic.
Metab Eng, 55: 201-211. [PMID:31340171]
4. Schiefer A, Schmitz A, Schäberle TF, Specht S, Lämmer C, Johnston KL, Vassylyev DG, König GM, Hoerauf A, Pfarr K. (2012)
Corallopyronin A specifically targets and depletes essential obligate Wolbachia endobacteria from filarial nematodes in vivo.
J Infect Dis, 206 (2): 249-57. [PMID:22586066]
5. Schmitz A, Kehraus S, Schäberle TF, Neu E, Almeida C, Roth M, König GM. (2014)
Corallorazines from the myxobacterium Corallococcus coralloides.
J Nat Prod, 77 (1): 159-63. [PMID:24422674]
6. Schäberle TF, Schmitz A, Zocher G, Schiefer A, Kehraus S, Neu E, Roth M, Vassylyev DG, Stehle T, Bierbaum G et al.. (2015)
Insights into Structure-Activity Relationships of Bacterial RNA Polymerase Inhibiting Corallopyronin Derivatives.
J Nat Prod, 78 (10): 2505-9. [PMID:26431157]