Compound ID | 2018

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Bacitracin

Class: Antimicrobial peptide

Agent Type: Natural product; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Cell wall synthesis inhibitor. Inhibits the formation of late-stage peptidoglycan intermediates (lipid intermediates) by inhibiting lipid phosphorylase
Description: Natural product produced by Bacillus licheniformis, composed of a mixture of related compounds. Used for minor skin wounds and eye infections often in combination with other antibiotics.
Year first mentioned: 1943
Highest development stage: Approved by FDA in 1948
Development status: Approved
Chemical structure(s):
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Molecular weight: 1422.7
Iso. SMILES: CCC(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(C)CC)NC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)C2CN=C(S2)[C@H](C(C)CC)N)CC(=O)N)CC(=O)O)CC3=CN=CN3)CC4=CC=CC=C4
InChI Key: MNJKVJAYSVAQLU-YOJCIBLDSA-N
Can. SMILES: CCC(C)[C@@H](C1=NCC(C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(=O)O)C(=O)N[C@@H](C(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(C)CC)NC(=O)[C@@H](CCCN)NC2=O)S1)N
InChI: InChI=1S/C66H103N17O16S/c1-9-35(6)52(69)66-72-32-48(100-66)63(97)80-43(26-34(4)5)59(93)75-42(22-23-50(85)86)58(92)83-53(36(7)10-2)64(98)76-40-20-15-16-25-71-55(89)46(29-49(68)84)78-62(96)47(30-51(87)88)79-61(95)45(28-39-31-70-33-73-39)77-60(94)44(27-38-18-13-12-14-19-38)81-65(99)54(37(8)11-3)82-57(91)41(21-17-24-67)74-56(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,70,73)(H,71,89)(H,74,90)(H,75,93)(H,76,98)(H,77,94)(H,78,96)(H,79,95)(H,80,97)(H,81,99)(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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/439542
Guide to Pharmacology: bacitracin A
Citation: https://www.nature.com/articles/s41598-017-01267-5

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