IC202C

CHEBI:66067 EXACT REVIEWED antimicrobial unspecified

What these status tags mean

Curation status describes a workflow state. SEEDED means the record entered through the source-seeding workflow; it does not imply that no later curation occurred. PROPOSED marks an addition awaiting review; REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record. These are workflow decisions, not independently verified human review. Agent-assisted contributions may appear in the record history.

Grounding describes the identifier mapping: EXACT uses an ontology identity asserted by the source; MINTED keeps a local identifier when no defensible ontology identity is available; REVIEW_NEEDED flags an exact structure whose ontology identity needs adjudication. The grounding note retains any unresolved alternatives. These tags do not establish the strength of producer or activity evidence.

An aldoxime isolated from Streptoalloteichus sp.1454-19. It is a siderophore which exhibits immunosuppressive activity on a mixed lymphocyte culture reaction (MLCR).

Structure

Standard InChIKey	RPHCJSPQKSVBSH-UHFFFAOYSA-N
SMILES	[H]C(CCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCN)=NO
Stereochemistry	fully defined

Filing pathway

Fatty acids — computed by NPClassifier npclassifier.gnps2.org@2026-10-31, which is why it is pinned rather than recomputed.

Producer organisms 1

A claim that this taxon makes the compound. The basis says what the evidence addressed — a knockout and a database assertion are not the same claim.

Taxon	Basis	Cluster	Evidence
Streptoalloteichus Strain: 1454-19 NCBITaxon:44103	AXENIC_CULTURE		PMID:10726924 reference PMID:10726924 evidence type PRIMARY_EXPERIMENT notes Isolation, structural elucidation, and iron-chelating characterization of the linear N-hydroxycadaverine-succinyl dihydroxamate aldoxime siderophore congener IC202C from Streptoalloteichus sp. 1454-19.

Occurrences 1

Somebody found the compound in this organism and cited it. That is not a claim that the organism makes it, and nothing here promotes one to the other.

Taxon	Source	Reference
Streptoalloteichus NCBITaxon:44103	CHEBI	PMID:10726924

Biosynthesis curated

Written by a curator with claim-level evidence on each step; not derived from a source. This is what the rest of the record exists to support.

Step	Enzyme	Reaction	Substrate → product	Evidence
1	Streptoalloteichus NIS hydroxamate siderophore synthetase pathway		CHEBI:18127 + CHEBI:50440 + CHEBI:50443 → CHEBI:66067	PMID:10726924

Step 1: Assembly of the linear dihydroxamate backbone from two N-(3-carboxypropanoyl)-N-hydroxycadaverine units condensed with a terminal 5-(hydroxyimino)pentylamine (aldoxime) unit in Streptoalloteichus sp. 1454-19 to yield IC202C.

Mechanism & Biosynthesis Overview

Causal graph — bioactivity 7 nodes, 6 edges

Biosynthesis of the linear dihydroxamate aldoxime siderophore congener IC202C in Streptoalloteichus sp. 1454-19, chelation of Fe(III), and inhibition of T-cell proliferation.

Subject	Predicate	Object	Notes	Evidence
cadaverine	converted_to	N-hydroxycadaverine	N-hydroxylation of cadaverine.	PMID:10726924 reference PMID:10726924 evidence type PRIMARY_EXPERIMENT notes IC202C shares the N-hydroxycadaverine-succinyl core with IC202A and IC202B.
N-hydroxycadaverine	converted_to	N-(3-carboxypropanoyl)-N-hydroxycadaverine	Succinylation generates N-(3-carboxypropanoyl)-N-hydroxycadaverine.	PMID:10726924 reference PMID:10726924 evidence type PRIMARY_EXPERIMENT notes NMR elucidation of IC202C.
N-(3-carboxypropanoyl)-N-hydroxycadaverine	substrate_of	IC202 NIS siderophore synthetase	Condensed into the dihydroxamate scaffold capped by a terminal aldoxime group.	PMID:10726924 reference PMID:10726924 evidence type PRIMARY_EXPERIMENT notes Structure elucidation of IC202C.
IC202 NIS siderophore synthetase	synthesizes	IC202C	Produces IC202C in Streptoalloteichus sp. 1454-19.	PMID:10726924 reference PMID:10726924 evidence type PRIMARY_EXPERIMENT notes Isolation of IC202C from Streptoalloteichus sp. 1454-19.
IC202C	chelates	iron(3+)	Coordinates ferric iron(3+) via the hydroxamate and aldoxime donor groups.	PMID:10726924 reference PMID:10726924 evidence type PRIMARY_EXPERIMENT notes Siderophore iron-chelating activity of IC202C.
IC202C	inhibits	cell population proliferation	Inhibits mixed lymphocyte culture proliferation (IC50 = 1.6 ug/mL) via iron chelation.	PMID:10726924 reference PMID:10726924 evidence type PRIMARY_EXPERIMENT notes Biological activity of IC202C in mixed lymphocyte reaction.

Every edge carries its own citation; an uncited edge is refused by the corpus tests.

Molecular targets 1

Target	Target organism	Measurement	Evidence
iron(3+) OTHER BINDS Coordination of ferric iron(3+) via the two N-hydroxycadaverine-succinyl hydroxamate groups and terminal aldoxime moiety of IC202C.			PMID:10726924 reference PMID:10726924 evidence type PRIMARY_EXPERIMENT notes Isolation, structural elucidation, and ferric iron-binding / immunosuppressive characterization of the aldoxime-hydroxamate siderophore IC202C from Streptoalloteichus sp. 1454-19.

Elsewhere in the fleet

AntibioticMech — CHEBI:66067 (same structure, same inchikey)

Explore across X-Mech

AntibioticMech (IC202C) ↗ MediaIngredientMech (CHEBI:66067) ↗ TaxonMech: Streptoalloteichus (NCBITaxon:44103) ↗

Provenance

Source concept	Source	Version
CHEBI:66067	CHEBI	3-star

This page is generated from data/natural_products/fatty_acids/ic202c.yaml, which is generated from the committed inventories. Neither is edited by hand.