boromycin   Click here for help

GtoPdb Ligand ID: 13447

Antimalarial Ligand
Compound class: Natural product
Comment: Boromycin is a polyether macrolide, initially isolated from a new strain of Streptomyces antibioticus (ETH 28 829), and reported as the first boron-containing natural product to be identified [3-4]. It is a broad-spectrum antimicrobial compound, with potent activity against a number of Gram-positive bacteria, viruses, and protozoan parasites [1-2,4-5].

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 16
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 209.99
Molecular weight 878.87
XLogP 5.74
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES CC(C)[C@H](C(=O)O[C@H](C)[C@@H]1C/C=C/CC[C@@H](C(C)(C)[C@@H]2CC[C@@H](C)[C@]3(C4C(=O)O[C@H]5C[C@@H](CCC[C@H](C(C)(C)[C@@H]6CC[C@@H](C)[C@]7(C(C(=O)O1)O[B-](O4)(O7)O3)O6)O)O[C@@H]5C)O2)O)N
Isomeric SMILES [B-]123OC4C(=O)O[C@@H](C/C=C/CC[C@@H](C([C@@H]5CC[C@H]([C@@](O1)(O5)C(O2)C(=O)O[C@H]6C[C@@H](CCC[C@H](C([C@@H]7CC[C@H]([C@@]4(O3)O7)C)(C)C)O)O[C@@H]6C)C)(C)C)O)[C@@H](C)OC(=O)[C@@H](C(C)C)N
InChI InChI=1S/C45H73BNO15/c1-24(2)36(47)39(50)54-27(5)30-16-12-11-13-17-32(48)42(7,8)34-21-19-26(4)45(57-34)38-41(52)56-31-23-29(53-28(31)6)15-14-18-33(49)43(9,10)35-22-20-25(3)44(58-35)37(40(51)55-30)59-46(60-38,61-44)62-45/h11-12,24-38,48-49H,13-23,47H2,1-10H3/q-1/b12-11+/t25-,26-,27-,28-,29-,30+,31+,32+,33-,34+,35+,36-,37?,38?,44+,45+,46?/m1/s1
InChI Key OOBFYEMEQCZLJL-XURNZCJASA-N
Guide to Malaria Pharmacology Comments
Boromycin is a promising antimalarial candidate with activity against multiple lifecycle stages of the Plasmodium parasite [2].

Potential Target/Mechanism Of Action: As the precise mechanism of action in the malaria parasite is not yet known, we have not tagged a Plasmodium molecular target for this compound. Further information about possible mechanistic insights is provided under the Clinical data tab.