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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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Natural product
Ligand families/groups Antimalarial ligands
IUPAC Name Click here for help
[(1R)-1-[(1R,5S,7E,11S,13S,16R,17R,24S,25R,27R,31R,33S,36R)-11,31-dihydroxy-12,12,16,25,32,32,36-heptamethyl-3,22-dioxo-4,18,20,23,26,37,38,40,41-nonaoxa-19-boranuidaheptacyclo[17.17.1.11,33.12,19.113,17.124,27.017,21]hentetracont-7-en-5-yl]ethyl] (2R)-2-amino-3-methylbutanoate
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Boromycin
Other databases
CAS Registry No. 34524-20-4 (source: Scifinder)
GtoPdb PubChem SID 500839857
PubChem CID 6436027
Search Google for chemical match using the InChIKey OOBFYEMEQCZLJL-XURNZCJASA-N
Search Google for chemicals with the same backbone OOBFYEMEQCZLJL
UniChem Compound Search for chemical match using the InChIKey OOBFYEMEQCZLJL-XURNZCJASA-N
UniChem Connectivity Search for chemical match using the InChIKey OOBFYEMEQCZLJL-XURNZCJASA-N