desferricoprogen B

CHEBI:133861 EXACT REVIEWED

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 member of the class of 2,5-diketopiperazines that is 2,5-diketopiperazine which is substituted at positions 3 and 6 by 3-(hydroxyamino)propyl groups in which the nitrogens have been acylated by (2E)-5-hydroxy-3-methylpent-2-enoyl groups. The substituent at position 3 has been further modified by having its terminal hydroxy group esterified by condensation with the carboxy group of N5-hydroxy-L-ornithine in which the N5 nitrogen has been acylated by a (2E)-5-hydroxy-3-methylpent-2-enoyl group.

Structure

Standard InChIKey	XRSRJBBRTCEBNS-CAGSISFISA-N
SMILES	[H][C@@]1(CCCN(O)C(=O)/C=C(\C)CCO)NC(=O)[C@]([H])(CCCN(O)C(=O)/C=C(\C)CCOC(=O)[C@@H](N)CCCN(O)C(=O)/C=C(\C)CCO)NC1=O
Stereochemistry	fully defined

Filing pathway

Amino acids and peptides — 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
Neurospora crassa Strain: ATCC 10816 NCBITaxon:5141	AXENIC_CULTURE		PMID:5484314 reference PMID:5484314 evidence type PRIMARY_EXPERIMENT notes Isolation and structural elucidation of desferricoprogen B (deacetyl-desferricoprogen) secreted by iron-deficient axenic cultures of Neurospora crassa and Fusarium dimerum.
Aspergillus niger Strain: N402 NCBITaxon:5061	BGC_CHARACTERIZED		PMID:25062661 reference PMID:25062661 evidence type PRIMARY_EXPERIMENT notes Targeted gene deletion of sidA (An16g01850, L-ornithine N5-monooxygenase) and sidD (An03g03560, nonribosomal peptide synthetase) in Aspergillus niger N402 completely abolishes coprogen B (desferricoprogen B) biosynthesis.

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
Aspergillus niger NCBITaxon:5061	CHEBI	PMID:25062661

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	Coprogen nonribosomal peptide synthetase (SidD)		CHEBI:15729 + CHEBI:17710 + CHEBI:79095 + CHEBI:15422 → CHEBI:133861	PMID:25062661

Step 1: Iterative condensation of three N5-trans-anhydromevalonyl-N5-hydroxy-L-ornithine units (forming a 2,5-diketopiperazine dimer esterified to a third monomer bearing a free alpha-amino group) to release desferricoprogen B.

Mechanism & Biosynthesis Overview

Causal graph — bioactivity 7 nodes, 6 edges

SidD NRPS-catalyzed biosynthesis of the trihydroxamate siderophore desferricoprogen B in filamentous fungi (Neurospora crassa, Aspergillus niger) and octahedral chelation of ferric iron(3+) to form coprogen B.

Subject	Predicate	Object	Notes	Evidence
L-ornithine	converted_to	N(5)-hydroxy-L-ornithine	L-ornithine is N5-hydroxylated by SidA to N(5)-hydroxy-L-ornithine.	PMID:25062661 reference PMID:25062661 evidence type PRIMARY_EXPERIMENT notes SidA (An16g01850) catalyzes the first committed step of fungal hydroxamate siderophore synthesis in Aspergillus niger.
(R)-mevalonic acid	substrate_of	Coprogen nonribosomal peptide synthetase SidD	Provides the trans-anhydromevalonyl acyl groups.	PMID:5484314 reference PMID:5484314 evidence type PRIMARY_EXPERIMENT notes Coprogen B contains three trans-anhydromevalonic acid residues.
N(5)-hydroxy-L-ornithine	substrate_of	Coprogen nonribosomal peptide synthetase SidD	Following N5-acylation with trans-anhydromevalonyl-CoA, three N(5)-hydroxy-L-ornithine-derived units are condensed by SidD.	PMID:25062661 reference PMID:25062661 evidence type PRIMARY_EXPERIMENT notes SidD NRPS catalyzes assembly of the trimeric ester-linked diketopiperazine scaffold.
Coprogen nonribosomal peptide synthetase SidD	synthesizes	desferricoprogen B	Releases desferricoprogen B.	PMID:25062661 reference PMID:25062661 evidence type PRIMARY_EXPERIMENT notes Deletion of sidD abolishes coprogen B production in Aspergillus niger.
desferricoprogen B	chelates	iron(3+)	Hexadentate coordination of ferric iron(3+) to form coprogen B.	PMID:5484314 reference PMID:5484314 evidence type PRIMARY_EXPERIMENT notes Characterization of the ferric complex coprogen B.
desferricoprogen B	enables	iron ion transport	In its ferric-complexed form (coprogen B), desferricoprogen B mediates fungal extracellular ferric iron acquisition under iron starvation.	PMID:5484314 PMID:25062661 reference PMID:5484314 evidence type PRIMARY_EXPERIMENT notes Coprogen B is secreted as an extracellular ferric siderophore under iron-limiting growth. reference PMID:25062661 evidence type PRIMARY_EXPERIMENT notes Extracellular coprogen B biosynthesis under iron starvation in Aspergillus niger.

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 Hexadentate octahedral coordination of ferric iron(3+) via three trans-anhydromevalonyl-N5-hydroxy-L-ornithine hydroxamate groups to form coprogen B (deacetylcoprogen).			PMID:5484314 PMID:25062661 reference PMID:5484314 evidence type PRIMARY_EXPERIMENT notes Isolation and structural elucidation of coprogen B (the ferric complex of desferricoprogen B) from Penicillium, Fusarium, and Neurospora crassa. reference PMID:25062661 evidence type PRIMARY_EXPERIMENT notes Genetic deletion of sidD in Aspergillus niger N402 abolishes biosynthesis of coprogen B.

Explore across X-Mech

AntibioticMech (desferricoprogen B) ↗ MediaIngredientMech (CHEBI:133861) ↗ TaxonMech: Neurospora crassa (NCBITaxon:5141) ↗ TaxonMech: Aspergillus niger (NCBITaxon:5061) ↗

Provenance

Source concept	Source	Version
CHEBI:133861	CHEBI	3-star

This page is generated from data/natural_products/amino_acids_and_peptides/desferricoprogen-b.yaml, which is generated from the committed inventories. Neither is edited by hand.