bacitracin A

CHEBI:35862 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

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. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

nonribosomal peptide antibioticsARO:3009657

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:15841 CHEBI:15841
CHEBI:24613 CHEBI:24613
ARO:3009657 ARO:3009657

Chemical structure

Computed structure properties
Molecular formula	C66H103N17O16S
Charge	0
Average mass	1422.72 Da
Monoisotopic mass	1421.74894 Da
Source	ChEBI
InChIKey	CLKOFPXJLQSYAH-ABRJDSQDSA-N

SMILES

CC[C@H](C)[C@H](N)C1=N[C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(=O)O)C(=O)N[C@H](C(=O)N[C@H]2CCCCNC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](CC(=O)O)NC(=O)[C@H](Cc3cncn3)NC(=O)[C@@H](Cc3ccccc3)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H](CCCN)NC2=O)[C@@H](C)CC)CS1

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

Also called

N-({(4R)-2-[(1S,2S)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazol-4-yl}carbonyl)-L-leucyl-D-α-glutamyl-N-[(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-4-ylmethyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptaazacyclopentacosan-21-yl]-L-isoleucinamide (EXACT_SYNONYM)— chebi
Bacitracin A2a (EXACT_SYNONYM)— chebi
Bacitracin F, 1-(N-((2-(1-amino-2-methylbutyl)-4,5-dihydro-4-thiazolyl)carbonyl)-l-leucine)- (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:33281 CHEBI:33281
CHEBI:33282 CHEBI:33282

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
ARO	`ARO:3000629`	bacitracin A	`antibioticmech:aro-a443732110`	2026-08-30
CHEBI	`CHEBI:35862`	bacitracin A	`antibioticmech:chebi-7b971bf204`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

bacitracin sensitive isoprenyl pyrophosphate CELL_WALL_COMPONENT ATTACKED_COMPONENT

ARO:3000719

CARD/ARO database assertion; target organism, strain, and assay are not specified. Isoprenyl pyrophosphate is a cell-wall carrier intermediate rather than a protein. Evidence status: DATABASE_ASSERTION_ONLY. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000719 (CARD/ARO asserts targeted_by_antibiotic ARO:3000629 (bacitracin A); database assertion, not a primary citation.)

undecaprenyl pyrophosphate CELL_WALL_COMPONENT ATTACKED_COMPONENT

ARO:3003251

CARD/ARO database assertion; target organism, strain, and assay are not specified. Undecaprenyl pyrophosphate is a cell-wall carrier intermediate. Evidence status: DATABASE_ASSERTION_ONLY. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3003251 (CARD/ARO asserts targeted_by_antibiotic ARO:3000629 (bacitracin A); database assertion, not a primary citation.)

Resistance mechanisms

4 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

ANTIBIOTIC_EFFLUX 2

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
bcrA	ARO:3002987	not organism-specific	—	ARO:3002987 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000629 (bacitracin A); database assertion, not a primary citation.)
bcrB	ARO:3002988	not organism-specific	—	ARO:3002988 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000629 (bacitracin A); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_ALTERATION 2

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
bacA	ARO:3002986	not organism-specific	—	ARO:3002986 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000629 (bacitracin A); database assertion, not a primary citation.)
bcrC	ARO:3003250	not organism-specific	—	ARO:3003250 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000629 (bacitracin A); database assertion, not a primary citation.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.