borrelidin   Click here for help

GtoPdb Ligand ID: 11306

Synonyms: (-)-borrelidin
Antimalarial Ligand
Comment: Borrelidin is a macrolide antibiotic originally isolated from Streptomyces. It is a noncompetitive inhibitor of both bacterial and eukaryotic threonyl-tRNA synthetases (also known as threonine--tRNA ligase), exhibiting antibacterial, antimalarial and antiangiogenic activities.

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 127.85
Molecular weight 489.31
XLogP 4.67
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES N#C/C/1=C/C=C/C[C@H](OC(=O)C[C@@H]([C@H](C[C@H](C[C@H](C[C@@H]([C@H]1O)C)C)C)C)O)[C@@H]1CCC[C@H]1C(=O)O
Isomeric SMILES N#C/C/1=C/C=C/C[C@H](OC(=O)C[C@@H]([C@H](C[C@H](C[C@H](C[C@@H]([C@H]1O)C)C)C)C)O)[C@@H]1CCC[C@H]1C(=O)O
InChI InChI=1S/C28H43NO6/c1-17-12-18(2)14-20(4)27(32)21(16-29)8-5-6-11-25(22-9-7-10-23(22)28(33)34)35-26(31)15-24(30)19(3)13-17/h5-6,8,17-20,22-25,27,30,32H,7,9-15H2,1-4H3,(H,33,34)/b6-5+,21-8-/t17-,18+,19-,20-,22+,23+,24-,25-,27+/m0/s1
InChI Key OJCKRNPLOZHAOU-UGKRXNSESA-N
References
1. Novoa EM, Camacho N, Tor A, Wilkinson B, Moss S, Marín-García P, Azcárate IG, Bautista JM, Mirando AC, Francklyn CS et al.. (2014)
Analogs of natural aminoacyl-tRNA synthetase inhibitors clear malaria in vivo.
Proc Natl Acad Sci U S A, 111 (51): E5508-17. [PMID:25489076]
2. Otoguro K, Ui H, Ishiyama A, Kobayashi M, Togashi H, Takahashi Y, Masuma R, Tanaka H, Tomoda H, Yamada H et al.. (2003)
In vitro and in vivo antimalarial activities of a non-glycosidic 18-membered macrolide antibiotic, borrelidin, against drug-resistant strains of Plasmodia.
J Antibiot (Tokyo), 56 (8): 727-9. [PMID:14563165]
3. Sugawara A, Tanaka T, Hirose T, Ishiyama A, Iwatsuki M, Takahashi Y, Otoguro K, Ōmura S, Sunazuka T. (2013)
Borrelidin analogues with antimalarial activity: design, synthesis and biological evaluation against Plasmodium falciparum parasites.
Bioorg Med Chem Lett, 23 (8): 2302-5. [PMID:23499502]