microcin c

CHEBI:82754 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT SEEDED

A member of the family of microcins comprising a heptapeptide covalently liinked to 3-aminopropyl-AMP via an acylphosphoramide linkage. A potent inhibitor of aspartyl-tRNA synthetase. — 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

Strictly broader compounds or drug classes this molecule belongs to.

microcin CHEBI:64627

Chemical structure

Computed structure properties
Molecular formula	C42H69N18O18PS
Charge	0
Average mass	1177.163 Da
Monoisotopic mass	1176.44955 Da
Source	ChEBI
InChIKey	PQZVLCSYKIYYRQ-CRNXWWIHSA-N

SMILES

[H]C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(=O)O)C(=O)NP(=O)(OCCCN)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O)[C@@H](C)O

InChI

InChI=1S/C42H69N18O18PS/c1-19(35(69)57-24(13-28(65)66)39(73)59-79(75,76-10-5-8-43)77-15-25-31(67)32(68)41(78-25)60-17-52-30-33(45)50-16-51-34(30)60)54-38(72)23(12-26(44)63)55-27(64)14-49-40(74)29(20(2)62)58-37(71)22(6-4-9-48-42(46)47)56-36(70)21(53-18-61)7-11-80-3/h16-25,29,31-32,41,62,67-68H,4-15,43H2,1-3H3,(H2,44,63)(H,49,74)(H,53,61)(H,54,72)(H,55,64)(H,56,70)(H,57,69)(H,58,71)(H,65,66)(H2,45,50,51)(H4,46,47,48)(H,59,73,75)/t19-,20+,21-,22-,23-,24-,25+,29-,31+,32+,41+,79?/m0/s1

Also called

5'-O-{(3-aminopropoxy)[(N-formyl-L-methionyl-L-arginyl-L-threonylglycyl-L-asparaginyl-L-alanyl-L-α-aspartyl)amino]phosphoryl}adenosine (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.

metacyc.compound:CPD0-1129

Activity roles

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

antimicrobial agent CHEBI:33281

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
CHEBI	`CHEBI:82754`	microcin c	`antibioticmech:chebi-ef3b192c53`	2026-08-30

Resistance mechanisms

2 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

ANTIBIOTIC_INACTIVATION 2

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
MccE-associated inactivation after microcin C processing The mechanism concerns processed intracellular material, not direct acetylation of intact microcin C. Native material and synthetic analogues are distinct. The paper corrects the gene-start annotation; a gene-name match does not resolve the experimental protein. Reference candidates remain separate from the experimental proteins. NCBITaxon:562 denotes the E. coli reference species, not a strain or genome. BL21(DE3) is a reported host background, not an exact derivative assignment. No clinical category or numerical AST is inferred.	—	not organism-specific	mccE	PMID:20159968 (Author-uploaded primary text: Results, Table 1 and Discussion. The route follows the authors' interpretation. Figures and supplement were not visually inspected.) Source-reported biochemical and laboratory-cell comparisons; qualitative result only
MccF-associated enzymatic inactivation of microcin C Primary product analysis supports cleavage of intact microcin C. Deformylated material was also present and separately discussed; this is not a pure-compound organismal AST claim. The paper distinguishes intact, processed and analogue substrates. Reference candidates remain separate from the experimental proteins. NCBITaxon:562 denotes the E. coli reference species, not a strain or genome. BL21(DE3) is a reported host background, not an exact derivative assignment. No clinical category or numerical AST is inferred.	—	not organism-specific	mccF	PMID:20876530 (Author-uploaded primary text: Results on in vitro rescue, loss of activity and product analysis; Figures 3-5 captions. Figures and supplements were not visually inspected.) Source-reported biochemical inactivation and product analysis; qualitative result only

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (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
CURATED_RESISTANCE_EVIDENCE 2026-10-09 · codex · LLM-assisted
Added qualitative primary-backed resistance evidence with donor, host and substrate distinctions. Reference proteins are not assigned as exact experimental alleles. Existing chemical and source evidence preserved; whole-record review remains open.

Provenance

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

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