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 (ThrRS), exhibiting antibacterial, antimalarial and antiangiogenic activities.
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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
Classification Click here for help
Compound class Natural product or derivative
Ligand families/groups Antimalarial ligands
IUPAC Name Click here for help
(1R,2R)-2-[(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid
Synonyms Click here for help
(-)-borrelidin
Database Links Click here for help
CAS Registry No. 7184-60-3 (source: Scifinder)
ChEMBL Ligand CHEMBL70590
GtoPdb PubChem SID 434321741
PubChem CID 6436801
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