IC202B

CHEBI:66066 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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.

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

Structure

Standard InChIKey	BHNYEXHOBOECJW-UHFFFAOYSA-N
SMILES	NCCCCCN(O)C(=O)CCC(=O)NCCCCCN(O)C(=O)CCC(=O)NCCCCC[N+](=O)[O-]
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 C-nitro siderophore congener IC202B 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:66066	PMID:10726924

Step 1: Assembly of the linear dihydroxamate backbone from two N-(3-carboxypropanoyl)-N-hydroxycadaverine units condensed with a C-terminal 5-nitropentylamine (N-oxidized cadaverine) unit in Streptoalloteichus sp. 1454-19 to yield IC202B.

Mechanism & Biosynthesis Overview

Causal graph — bioactivity 7 nodes, 6 edges

Biosynthesis of the linear dihydroxamate C-nitro siderophore congener IC202B 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 IC202B shares the N-hydroxycadaverine-succinyl core with IC202A.
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 IC202B.
N-(3-carboxypropanoyl)-N-hydroxycadaverine	substrate_of	IC202 NIS siderophore synthetase	Condensed into the dihydroxamate scaffold capped by a terminal 5-nitropentyl group.	PMID:10726924 reference PMID:10726924 evidence type PRIMARY_EXPERIMENT notes Structure elucidation of IC202B.
IC202 NIS siderophore synthetase	synthesizes	IC202B	Produces IC202B in Streptoalloteichus sp. 1454-19.	PMID:10726924 reference PMID:10726924 evidence type PRIMARY_EXPERIMENT notes Isolation of IC202B from Streptoalloteichus sp. 1454-19.
IC202B	chelates	iron(3+)	Coordinates ferric iron(3+) via the hydroxamate donor groups.	PMID:10726924 reference PMID:10726924 evidence type PRIMARY_EXPERIMENT notes Siderophore iron-chelating activity of IC202B.
IC202B	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 IC202B 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 of IC202B (the terminal 5-nitropentyl C-nitro congener of IC202A).			PMID:10726924 reference PMID:10726924 evidence type PRIMARY_EXPERIMENT notes Isolation, structural elucidation, and ferric iron-binding / immunosuppressive characterization of the hydroxamate siderophores IC202B and IC202C from Streptoalloteichus sp. 1454-19.

Elsewhere in the fleet

AntibioticMech — CHEBI:66066 (same structure, same inchikey)

Explore across X-Mech

AntibioticMech (IC202B) ↗ MediaIngredientMech (CHEBI:66066) ↗ TaxonMech: Streptoalloteichus (NCBITaxon:44103) ↗

Provenance

Source concept	Source	Version
CHEBI:66066	CHEBI	3-star

This page is generated from data/natural_products/fatty_acids/ic202b.yaml, which is generated from the committed inventories. Neither is edited by hand.