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.

Label unavailable CHEBI:15841
Label unavailable CHEBI:24613
nonribosomal peptide antibiotics 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

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Activity roles

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

antimicrobial agent CHEBI:33281
antibacterial agent 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 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

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 (YAML).

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