desferricoprogen

CHEBI:83125 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 N2-acetyl-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	AKLLFACZGZTMGS-FCRFISLRSA-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](CCCN(O)C(=O)/C=C(\C)CCO)NC(C)=O)NC1=O
Stereochemistry	fully defined

Filing pathway

Unclassified — 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: 74A NCBITaxon:5141	AXENIC_CULTURE		PMID:2951253 reference PMID:2951253 evidence type PRIMARY_EXPERIMENT notes Purification and Mossbauer/HPLC characterization of coprogen (desferricoprogen ferric complex) biosynthesized as the major extracellular siderophore of iron-deficient Neurospora crassa 74A.
Aspergillus niger Strain: N402 NCBITaxon:5061	BGC_CHARACTERIZED		PMID:25062661 reference PMID:25062661 evidence type PRIMARY_EXPERIMENT notes Targeted gene deletion of sidA (An16g01850) and sidD (An03g03560) and LC-MS metabolite profiling in Aspergillus niger N402 establish biosynthesis of coprogen (desferricoprogen) and coprogen B.

Occurrences 0

None cited.

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	L-ornithine N5-monooxygenase (SidA)		CHEBI:15729 → CHEBI:79095	PMID:25062661
2	Trans-anhydromevalonyl-CoA transferase (SidF), coprogen nonribosomal peptide synthetase (SidD), and N-acetyltransferase		CHEBI:79095 + CHEBI:17710 + CHEBI:15351 + CHEBI:15422 → CHEBI:133861 + CHEBI:83125	PMID:25062661

Step 1: FAD- and NADPH-dependent N5-hydroxylation of L-ornithine to N(5)-hydroxy-L-ornithine by SidA (An16g01850 in Aspergillus niger).

Step 2: N5-acylation of N(5)-hydroxy-L-ornithine with mevalonate-derived trans-anhydromevalonyl-CoA followed by SidD (An03g03560) NRPS-catalyzed condensation of three N5-trans-anhydromevalonyl-N5-hydroxy-L-ornithine units (forming a diketopiperazine ring linked via an ester bond to a third monomer) to produce desferricoprogen B, and subsequent Nalpha-acetylation to yield desferricoprogen.

Mechanism & Biosynthesis Overview

Causal graph — bioactivity 11 nodes, 10 edges

Fungal NRPS-directed biosynthesis of the ester-linked diketopiperazine trihydroxamate siderophore desferricoprogen in Neurospora crassa and Aspergillus niger, hexadentate chelation of Fe(III) and CMM trivalent cations Ga(III) and Cr(III), and bacterial xenosiderophore uptake via FhuE.

Subject	Predicate	Object	Notes	Evidence
L-ornithine	converted_to	N(5)-hydroxy-L-ornithine	N5-hydroxylation of L-ornithine by SidA generates N(5)-hydroxy-L-ornithine.	PMID:25062661 reference PMID:25062661 evidence type PRIMARY_EXPERIMENT notes sidA (An16g01850) encodes L-ornithine N5-monooxygenase initiating coprogen biosynthesis in Aspergillus niger.
(R)-mevalonic acid	substrate_of	Coprogen nonribosomal peptide synthetase SidD	Supplies the trans-anhydromevalonyl acyl groups of the three hydroxamate units.	PMID:25062661 reference PMID:25062661 evidence type PRIMARY_EXPERIMENT notes Mevalonate-derived trans-anhydromevalonyl-CoA acylates N5-hydroxyornithine.
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 monomers are condensed by SidD.	PMID:25062661 reference PMID:25062661 evidence type PRIMARY_EXPERIMENT notes SidD NRPS assembles the coprogen B / coprogen trihydroxamate scaffold.
Coprogen nonribosomal peptide synthetase SidD	synthesizes	desferricoprogen B	Releases the N-deacetylated precursor desferricoprogen B.	PMID:5484314 reference PMID:5484314 evidence type PRIMARY_EXPERIMENT notes Desferricoprogen B is the N-deacetylated derivative of desferricoprogen.
desferricoprogen B	precursor_of	desferricoprogen	Nalpha-acetylation converts desferricoprogen B into desferricoprogen.	PMID:25062661 reference PMID:25062661 evidence type PRIMARY_EXPERIMENT notes Aspergillus niger produces both coprogen B and N-acetylated coprogen via the SidD pathway.
desferricoprogen	chelates	iron(3+)	Hexadentate coordination of ferric iron(3+) to form coprogen.	PMID:2951253 reference PMID:2951253 evidence type PRIMARY_EXPERIMENT notes Mossbauer study of ferric coprogen in Neurospora crassa.
desferricoprogen	chelates	gallium(3+)	[CMM] Octahedral coordination of trivalent gallium(3+) to form [Ga(III)]-coprogen.	PMID:20351354 PMID:40099411 reference PMID:20351354 evidence type PRIMARY_EXPERIMENT notes 68Ga radiolabeling, stability, and fungal uptake of [68Ga]Ga-coprogen. reference PMID:40099411 evidence type PRIMARY_EXPERIMENT notes Radiochemical complexation, stability, and microbial uptake of [68Ga]Ga-coprogen.
desferricoprogen	chelates	chromium(3+)	[CMM] Octahedral coordination of chromium(3+) into cis and trans chromic desferricoprogen isomers.	PMID:2934378 reference PMID:2934378 evidence type PRIMARY_EXPERIMENT notes Chromic desferricoprogen isomers inhibit coprogen uptake in Neurospora crassa.
desferricoprogen	binds	Outer membrane receptor FhuE	In its ferric-complexed form (coprogen), desferricoprogen is recognized by the E. coli outer membrane receptor FhuE.	PMID:3032906 reference PMID:3032906 evidence type PRIMARY_EXPERIMENT notes FhuE is the outer membrane receptor for ferric-coprogen in E. coli.
Outer membrane receptor FhuE	enables	siderophore transport	TonB-dependent import of ferric-coprogen across the outer membrane.	PMID:3032906 reference PMID:3032906 evidence type PRIMARY_EXPERIMENT notes fhuE-mediated ferric-coprogen transport.

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

Molecular targets 3

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 (composed of a diketopiperazine dimer ester-linked to a third N-acetylated monomer) to form coprogen.			PMID:2951253 PMID:5484314 PMID:2934378 reference PMID:2951253 evidence type PRIMARY_EXPERIMENT notes Mossbauer spectroscopy and in vivo transport characterization of ferric coprogen (Fe(III)-desferricoprogen) in Neurospora crassa. reference PMID:5484314 evidence type PRIMARY_EXPERIMENT notes Isolation and structural characterization of ferric coprogen and coprogen B from filamentous fungi. reference PMID:2934378 evidence type PRIMARY_EXPERIMENT notes Characterization of ferric coprogen recognition and transport in Neurospora crassa.
gallium(3+) OTHER BINDS [Critical Mineral & Material (CMM)] Octahedral trihydroxamate coordination of trivalent gallium(3+) by desferricoprogen to form [Ga(III)]-coprogen, characterized by 68Ga radiolabeling, complex stability assays, and microbial uptake.			PMID:20351354 PMID:40099411 reference PMID:20351354 evidence type PRIMARY_EXPERIMENT notes Radiolabeling, in vitro stability, and Aspergillus fumigatus uptake evaluation of 68Ga-labeled fungal siderophores including [68Ga]Ga-coprogen. reference PMID:40099411 evidence type PRIMARY_EXPERIMENT notes Radiochemical complexation, stability, partition coefficient, and microbial uptake characterization of [68Ga]Ga-coprogen.
chromium(3+) OTHER BINDS [Critical Mineral & Material (CMM)] Octahedral coordination of chromium(3+) by desferricoprogen (cis-lambda and trans-delta coordination isomers resolved by reverse-phase HPLC) that competitively inhibit coprogen uptake in Neurospora crassa.			PMID:2934378 reference PMID:2934378 evidence type PRIMARY_EXPERIMENT notes Resolution and uptake-inhibition characterization of cis and trans coordination isomers of chromic desferricoprogen in Neurospora crassa.

Explore across X-Mech

AntibioticMech (desferricoprogen) ↗ MediaIngredientMech (CHEBI:83125) ↗ TaxonMech: Neurospora crassa (NCBITaxon:5141) ↗ TaxonMech: Aspergillus niger (NCBITaxon:5061) ↗

Provenance

Source concept	Source	Version
CHEBI:83125	CHEBI	3-star

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