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Bacitracin Zinc

CAT: 1330-1405-89-6Size: EachDry Ice: NoHazardous: No
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CAS Number
1405-89-6

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
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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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