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 Number	1405-89-6
PubChem CID	70687193
IUPAC Name	zinc (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 Formula	C66H101N17O16SZn
Molecular Weight	1486.1
Topological Polar Surface Area	562
Hydrogen Bond Donor Count	15
Hydrogen Bond Acceptor Count	21
Rotatable Bond Count	29
Heavy Atom Count	101
Formal Charge	0
Complexity	2840

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

CAS: 1405-89-6

CID: 70687193

Formula: C66H101N17O16SZn

MW: 1486.1

Interactive 3D Structure

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View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	1486.1
Hydrogen Bond Donor Count	15
Hydrogen Bond Acceptor Count	21
Rotatable Bond Count	29
Exact Mass	1483.662433
Monoisotopic Mass	1483.662433
Topological Polar Surface Area	562 Å²
Heavy Atom Count	101
Formal Charge	0
Complexity	2840
Isotope Atom Count	0
Defined Atom Stereocenter Count	15
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	2
Compound Is Canonicalized	Yes

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