IC202A

CHEBI:66065 EXACT REVIEWED antimicrobial unspecified

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

Structure

Standard InChIKey	BVRULQCEMCYBAM-UHFFFAOYSA-N
SMILES	[H]C(CCCC)=[N+]([O-])CCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCN
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 2

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:10092192 reference PMID:10092192 evidence type PRIMARY_EXPERIMENT notes Taxonomy, fermentation, isolation, and biological characterization of the linear N-hydroxycadaverine-succinyl dihydroxamate-nitrone siderophore IC202A from Streptoalloteichus sp. 1454-19.
Streptoalloteichus Strain: 1454-19 NCBITaxon:44103	AXENIC_CULTURE		PMID:10092193 reference PMID:10092193 evidence type PRIMARY_EXPERIMENT notes Physico-chemical properties, NMR/MS structural elucidation, and ferric iron chelation analysis of IC202A isolated 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:66065	PMID:10092192

Step 1: N-hydroxylation and succinylation of cadaverine units followed by ATP-dependent NIS synthetase condensation of two N-(3-carboxypropanoyl)-N-hydroxycadaverine units with a terminal N-oxidized cadaverine-derived nitrone moiety in Streptoalloteichus sp. 1454-19 to yield IC202A.

Mechanism & Biosynthesis Overview

Causal graph — bioactivity 7 nodes, 6 edges

Biosynthesis of the linear N-hydroxycadaverine-succinyl dihydroxamate-nitrone siderophore IC202A in Streptoalloteichus sp. 1454-19, chelation of Fe(III), and iron-depletion-mediated inhibition of T-lymphocyte proliferation.

Subject	Predicate	Object	Notes	Evidence
cadaverine	converted_to	N-hydroxycadaverine	N-hydroxylation of cadaverine generates N-hydroxycadaverine.	PMID:10092193 reference PMID:10092193 evidence type PRIMARY_EXPERIMENT notes IC202A contains N-hydroxycadaverine-derived hydroxamate units.
N-hydroxycadaverine	converted_to	N-(3-carboxypropanoyl)-N-hydroxycadaverine	Succinylation produces N-(3-carboxypropanoyl)-N-hydroxycadaverine.	PMID:10092193 reference PMID:10092193 evidence type PRIMARY_EXPERIMENT notes Succinyl-linked N-hydroxycadaverine repeat in IC202A.
N-(3-carboxypropanoyl)-N-hydroxycadaverine	substrate_of	IC202 NIS siderophore synthetase	Two N-(3-carboxypropanoyl)-N-hydroxycadaverine units are condensed with the terminal nitrone-bearing diamine unit.	PMID:10092193 reference PMID:10092193 evidence type PRIMARY_EXPERIMENT notes 2D NMR and MS structure elucidation of IC202A.
IC202 NIS siderophore synthetase	synthesizes	IC202A	Produces IC202A in Streptoalloteichus sp. 1454-19.	PMID:10092192 reference PMID:10092192 evidence type PRIMARY_EXPERIMENT notes Fermentation and isolation of IC202A from Streptoalloteichus sp. 1454-19.
IC202A	chelates	iron(3+)	Coordinates ferric iron(3+) via the hydroxamate and N-oxide donor groups.	PMID:10092193 reference PMID:10092193 evidence type PRIMARY_EXPERIMENT notes Formation of the 1:1 ferric complex of IC202A.
IC202A	inhibits	cell population proliferation	Suppresses mixed lymphocyte reaction T-cell proliferation (IC50 = 3.6 ug/mL) via iron chelation.	PMID:10092192 reference PMID:10092192 evidence type PRIMARY_EXPERIMENT notes Immunosuppressive activity of IC202A in mixed lymphocyte culture assay.

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 internal N-hydroxycadaverine-succinyl hydroxamate groups and terminal N-oxide (nitrone) moiety of IC202A.			PMID:10092192 PMID:10092193 reference PMID:10092192 evidence type PRIMARY_EXPERIMENT notes Fermentation, isolation, and biological characterization of the immunosuppressive hydroxamate siderophore IC202A from Streptoalloteichus sp. 1454-19; iron(III) complexation modulates its T-cell activity. reference PMID:10092193 evidence type PRIMARY_EXPERIMENT notes Physico-chemical properties and NMR/MS structure elucidation of IC202A and its ferric complex.

Elsewhere in the fleet

AntibioticMech — CHEBI:66065 (same structure, same inchikey)

Explore across X-Mech

AntibioticMech (IC202A) ↗ MediaIngredientMech (CHEBI:66065) ↗ TaxonMech: Streptoalloteichus (NCBITaxon:44103) ↗ TaxonMech: Streptoalloteichus (NCBITaxon:44103) ↗

Provenance

Source concept	Source	Version
CHEBI:66065	CHEBI	3-star

This page is generated from data/natural_products/fatty_acids/ic202a.yaml, which is generated from the committed inventories. Neither is edited by hand.