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Bacitracin Zinc

CAT: 1568-C08057Size: 50 mgDry Ice: YesHazardous: No
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CAT#:1568-C08057Size:50 mg
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CAS Number
1405-89-6
Synonyms
Zinc Bacitracin
SKU
C08057-50mg
Target
Bacterial
Applications
Microbiology
Smiles
[Zn++].CCC (C) C (N) C1=NCC (S1) C (=O) NC (CC (C) C) C (=O) NC (CCC ([O-]) =O) C (=O) NC (C (C) CC) C (=O) NC2CCCCNC (=O) C (CC (N) =O) NC (=O) C (CC ([O-]) =O) NC (=O) C (CC3=C[NH]C=N3) NC (=O) C (CC4=CC=CC=C4) NC (=O) C (NC (=O) C (CCCN) NC2=O) C (C) CC
Molecular Formula
C66H101N17O16SZn
Additionnal Information
Bacitracin (Zinc Bacitracin) is an antibiotic that interferes with the dephosphorylation of C55-isoprenyl pyrophosphate, a membrane carrier molecule that transports the building-blocks of the peptidoglycan bacterial cell wall outside of the inner membrane. It inhibits cleavage of Tyr from Met-enkephalin with IC50 of 10 μM.
Storage Conditions
2 years -80 in solvent

Chemical Information

Bacitracin Zinc

Bacitracin Zinc is the zinc salt form of bacitracin, a complex of cyclic polypeptide antibiotics, mainly bacitracin A, produced by spore-forming organisms belonging to the licheniformin group of the Bacillus subtilis with antibacterial activity. Bacitracin zinc binds to C55-isoprenyl pyrophosphate, a biphosphate lipid transport molecule that carries the building blocks of the peptidoglycan bacterial cell wall, thereby interfering with the enzymatic dephosphorylation of the C55-isoprenyl pyrophosphate and preventing peptidoglycan synthesis which leads to cell lysis.

CAS Number1405-89-6
PubChem CID70687193
IUPAC Namezinc (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-(carboxylatomethyl)-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-oxopentanoate
Molecular FormulaC66H101N17O16SZn
Molecular Weight1486.1
Topological Polar Surface Area562
Hydrogen Bond Donor Count15
Hydrogen Bond Acceptor Count21
Rotatable Bond Count29
Heavy Atom Count101
Formal Charge0
Complexity2840
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.[Zn+2]
InChI
InChI=1S/C66H103N17O16S.Zn/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);/q;+2/p-2/t35-,36-,37-,40-,41+,42+,43-,44+,45-,46-,47+,48-,52-,53-,54-;/m0./s1
InChIKey
UCRLQOPRDMGYOA-DFTDUNEMSA-L
Chemical Structure
2D Structure
2D structure of Bacitracin Zinc
CAS: 1405-89-6
CID: 70687193
Formula: C66H101N17O16SZn
MW: 1486.1
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight1486.1
Hydrogen Bond Donor Count15
Hydrogen Bond Acceptor Count21
Rotatable Bond Count29
Exact Mass1483.662433
Monoisotopic Mass1483.662433
Topological Polar Surface Area562 Ų
Heavy Atom Count101
Formal Charge0
Complexity2840
Isotope Atom Count0
Defined Atom Stereocenter Count15
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes

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