bacitracin A   Click here for help

GtoPdb Ligand ID: 12812

Approved drug
bacitracin A is an approved drug (FDA (1948))
Compound class: Natural product or derivative
Comment: Bacitracin A is a polypeptide antibacterial with activity against Gram-positive bacteria. It is the major component of bacitracin [2], a mixture of at least nine closely-related cyclic polypeptides produced by Bacillus licheniformis and Bacillus subtilis.
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 CDK toolkit. 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 33
Hydrogen bond donors 17
Rotatable bonds 35
Topological polar surface area 551.88
Molecular weight 1422.7
XLogP 2.62
No. Lipinski's rules broken 4
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.

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Canonical SMILES CC[C@H](C)[C@@H](C1=N[C@@H](CS1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(=O)O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H]2CCCCNC(=O)[C@H](CC(=O)N)NC(=O)[C@@H](CC(=O)O)NC(=O)[C@H](CC3=CN=CN3)NC(=O)[C@@H](CC4=CC=CC=C4)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H](CCCN)NC2=O)N
Isomeric SMILES CC[C@H](C)[C@H]1C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)NCCCC[C@@H](C(=O)N[C@@H](C(=O)N1)CCCN)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]2CSC(=N2)[C@H]([C@@H](C)CC)N)CC(=O)N)CC(=O)O)CC3=CN=CN3)CC4=CC=CC=C4
InChI InChI=1S/C66H103N17O16S/c1-9-35(6)52(69)66-81-48(32-100-66)63(97)76-43(26-34(4)5)59(93)74-42(22-23-50(85)86)58(92)83-53(36(7)10-2)64(98)75-40-20-15-16-25-71-55(89)46(29-49(68)84)78-62(96)47(30-51(87)88)79-61(95)45(28-39-31-70-33-72-39)77-60(94)44(27-38-18-13-12-14-19-38)80-65(99)54(37(8)11-3)82-57(91)41(21-17-24-67)73-56(40)90/h12-14,18-19,31,33-37,40-48,52-54H,9-11,15-17,20-30,32,67,69H2,1-8H3,(H2,68,84)(H,70,72)(H,71,89)(H,73,90)(H,74,93)(H,75,98)(H,76,97)(H,77,94)(H,78,96)(H,79,95)(H,80,99)(H,82,91)(H,83,92)(H,85,86)(H,87,88)/t35-,36-,37-,40-,41+,42+,43-,44+,45-,46-,47+,48-,52-,53-,54-/m0/s1
InChI Key CLKOFPXJLQSYAH-ABRJDSQDSA-N
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes (FDA (1948))
IUPAC Name Click here for help
(4R)-4-[[(2S)-2-[[(4R)-2-[(1S,2S)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazole-4-carbonyl]amino]-4-methylpentanoyl]amino]-5-[[(2S,3S)-1-[[(3S,6R,9S,12R,15S,18R,21S)-3-(2-amino-2-oxoethyl)-18-(3-aminopropyl)-12-benzyl-15-[(2S)-butan-2-yl]-6-(carboxymethyl)-9-(1H-imidazol-5-ylmethyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclopentacos-21-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-5-oxopentanoic acid
International Nonproprietary Names Click here for help
INN number INN
1167 bacitracin
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Bacitracin
Other databases
BindingDB Ligand 50458054
CAS Registry No. 22601-59-8 (source: Scifinder)
ChEBI CHEBI:35862
ChEMBL Ligand CHEMBL1200558
DrugBank Ligand DB00626
DrugCentral Ligand 281
GtoPdb PubChem SID 483123360
PubChem CID 10909430
Search Google for chemical match using the InChIKey CLKOFPXJLQSYAH-ABRJDSQDSA-N
Search Google for chemicals with the same backbone CLKOFPXJLQSYAH
Search PubMed clinical trials bacitracin
Search PubMed titles bacitracin
Search PubMed titles/abstracts bacitracin
UniChem Compound Search for chemical match using the InChIKey CLKOFPXJLQSYAH-ABRJDSQDSA-N
UniChem Connectivity Search for chemical match using the InChIKey CLKOFPXJLQSYAH-ABRJDSQDSA-N
Wikipedia Bacitracin