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Bacitracin (Standard)

CAT: 0804-HY-107193RSize: InquireDry Ice: NoHazardous: No
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CAS Number
1405-87-4
UNSPSC Description
Bacitracin (Standard) is the analytical standard of Bacitracin. This product is intended for research and analytical applications. Bacitracin is a polypeptide antibiotic against staphylococcal and pathogenic protozoa infections. Bacitracin inhibits cell wall biosynthesis and permeability through binding to the undecaprenyl pyrophosphate. Bacitracin inhibits macromolecular synthesis. Bacitracin is also a protein disulfide isomerase (PDI) inhibitor[1][2][3].
Target Antigen
Antibiotic; Bacterial; PDI
Type
Reference Standards
Related Pathways
Anti-infection;Cell Cycle/DNA Damage;Metabolic Enzyme/Protease
Field of Research
Infection; Cancer
Assay Protocol
https://www.medchemexpress.com/bacitracin-standard.html
Smiles
[Bacitracin]
Molecular Weight
1422.69
References & Citations
[1]Si W, et al. Colistin Induces S. aureus Susceptibility to Bacitracin. Front Microbiol. 2018 Nov 20;9:2805.|[2]Mohamed Faisal, et al. Bacitracin Inhibits the Oyster Pathogen Perkinsus marinus in Vitro and in Vivo. Journal of Aquatic Animal Health. Volume 11, 1999 - Issue 2. |[3]Yu SJ, et al. Enhancement of hexokinase II inhibitor-induced apoptosis in hepatocellular carcinoma cells via augmenting ER stress and anti-angiogenesis by protein disulfide isomerase inhibition. J Bioenerg Biomembr. 2012 Feb;44(1):101-15.
Shipping Conditions
Room temperature

Chemical Information

Bacitracin

Bacitracin A is a homodetic cyclic peptide consisting of (4R)-2-[(1S,2S)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazole-4-carboxylic acid attached head-to-tail to L-leucyl,D-glutamyl, L-lysyl, D-ornityl, L-isoleucyl, D-phenylalanyl, L-histidyl. D-aspartyl and L-asparaginyl residues coupled in sequence and cyclised by condensation of the side-chain amino group of the L-lysyl residue with the C-terminal carboxylic acid group. It is the major component of bacitracin. It has a role as an antimicrobial agent and an antibacterial agent. It is a polypeptide and a homodetic cyclic peptide.

CAS Number1405-87-4
PubChem CID10909430
IUPAC Name(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
Molecular FormulaC66H103N17O16S
Molecular Weight1422.7
XLogP-4.1
Topological Polar Surface Area556
Hydrogen Bond Donor Count17
Hydrogen Bond Acceptor Count21
Rotatable Bond Count31
Heavy Atom Count100
Formal Charge0
Complexity2850
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
InChIKey
CLKOFPXJLQSYAH-ABRJDSQDSA-N
Chemical Structure
2D Structure
2D structure of Bacitracin
CAS: 1405-87-4
CID: 10909430
Formula: C66H103N17O16S
MW: 1422.7
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight1422.7
XLogP3-4.1
Hydrogen Bond Donor Count17
Hydrogen Bond Acceptor Count21
Rotatable Bond Count31
Exact Mass1421.74894144
Monoisotopic Mass1421.74894144
Topological Polar Surface Area556 Ų
Heavy Atom Count100
Formal Charge0
Complexity2850
Isotope Atom Count0
Defined Atom Stereocenter Count15
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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