desferrioxamine G

CHEBI:50439 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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.

Structure

Standard InChIKey	MIVGUYBAQIHKPJ-UHFFFAOYSA-N
SMILES	NCCCCCN(O)C(=O)CCC(=O)NCCCCCN(O)C(=O)CCC(=O)NCCCCCN(O)C(=O)CCC(=O)O
Stereochemistry	fully defined

Filing pathway

Fatty acids — computed by NPClassifier npclassifier.gnps2.org@2026-10-30, which is why it is pinned rather than recomputed. The gene cluster's asserted class is other, from MIBiG.

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
Streptomyces coelicolor A3(2) Strain: M145 NCBITaxon:100226	BGC_CHARACTERIZED	mibig:BGC0000940	PMID:15600304 reference PMID:15600304 evidence type PRIMARY_EXPERIMENT notes Genetic inactivation and LC-MS/MS characterization of the desABCD biosynthetic gene cluster (mibig:BGC0000940) in Streptomyces coelicolor M145 establish biosynthesis of linear desferrioxamine G (desferrioxamine G1) alongside desferrioxamines B and E.
Streptomyces coelicolor A3(2) Strain: A3(2) NCBITaxon:100226	BGC_CHARACTERIZED	mibig:BGC0000940	PMID:17704771 reference PMID:17704771 evidence type PRIMARY_EXPERIMENT notes In vitro enzymatic reconstitution of purified DesD (SCO2785) from the Streptomyces coelicolor A3(2) desABCD cluster (mibig:BGC0000940) demonstrates ATP-dependent condensation of N-hydroxy-N-succinylcadaverine into linear desferrioxamine G1 and cyclic desferrioxamine E.

Occurrences 0

None cited.

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000940	Streptomyces coelicolor A3(2) NCBITaxon:100226	CLUSTER_DEMONSTRATED	genbank:AL645882.2

A locus claim and a taxon claim are different questions. Heterologous expression settles the first and leaves the second where the isolation report left it.

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	Substrate → product	Evidence
1	DesA (lysine decarboxylase)	CHEBI:18019 → CHEBI:18127	PMID:15600304
2	DesB (cadaverine monooxygenase) and DesC (N-hydroxycadaverine acyltransferase)	CHEBI:18127 + CHEBI:15380 → ungrounded	PMID:15600304
3	DesD (NRPS-independent siderophore synthetase)	ungrounded → CHEBI:50439	PMID:17704771

Step 1: Pyridoxal 5'-phosphate-dependent decarboxylation of L-lysine to cadaverine; first committed step of the desABCD desferrioxamine biosynthetic pathway in Streptomyces coelicolor.

Step 2: FAD-dependent N-hydroxylation of cadaverine to N-hydroxycadaverine followed by DesC-catalyzed N-succinylation with succinyl-CoA to form N-hydroxy-N-succinylcadaverine (HSC) monomers.

Step 3: ATP-dependent iterative condensation of three N-hydroxy-N-succinylcadaverine units without macrocyclization to yield linear desferrioxamine G.

Mechanism & Biosynthesis Overview

Causal graph — bioactivity 11 nodes, 10 edges

DesABCD-mediated biosynthesis of linear tris-hydroxamate siderophore desferrioxamine G from L-lysine and succinyl-CoA and subsequent chelation of physiological Fe(III) as well as critical minerals Ga(III), Co(II), Ni(II), and La(III).

Subject	Predicate	Object	Notes	Evidence
L-lysine	converted_to	cadaverine	DesA decarboxylates L-lysine to cadaverine.	PMID:15600304 reference PMID:15600304 evidence type PRIMARY_EXPERIMENT notes DesA converts L-lysine to cadaverine in the desABCD pathway.
cadaverine	substrate_of	desABCD biosynthetic gene cluster (BGC0000940)	Cadaverine and succinyl-CoA are converted by DesB, DesC, and DesD.	PMID:15600304 reference PMID:15600304 evidence type PRIMARY_EXPERIMENT notes DesB, DesC, and DesD convert cadaverine and succinyl-CoA into desferrioxamine G1.
succinyl-CoA	substrate_of	desABCD biosynthetic gene cluster (BGC0000940)	Succinyl-CoA provides the succinyl linkers in N-hydroxy-N-succinylcadaverine.	PMID:29685972 reference PMID:29685972 evidence type PRIMARY_EXPERIMENT notes DesC uses succinyl-CoA to form N-hydroxy-N-succinylcadaverine.
desABCD biosynthetic gene cluster (BGC0000940)	synthesizes	desferrioxamine G	DesD trimerizes N-hydroxy-N-succinylcadaverine to release linear desferrioxamine G.	PMID:17704771 reference PMID:17704771 evidence type PRIMARY_EXPERIMENT notes DesD synthesizes linear desferrioxamine G1 from three N-hydroxy-N-succinylcadaverine units.
desferrioxamine G	chelates	iron(3+)	Forms 1:1 hexadentate ferrioxamine G1 complex (log beta110 ~ 30.6).	PMID:22641620 reference PMID:22641620 evidence type PRIMARY_EXPERIMENT notes Hexadentate tris-hydroxamate coordination of Fe(III) in aqueous solution.
iron(3+)	enables	siderophore transport	Ferrioxamine G1 delivers ferric iron to Streptomyces cells via ferrioxamine uptake ABC transporters.	PMID:15600304 reference PMID:15600304 evidence type PRIMARY_EXPERIMENT notes Desferrioxamine G1 serves as an extracellular ferric siderophore in Streptomyces coelicolor.
desferrioxamine G	chelates	gallium(3+)	[CMM] In vitro hexadentate coordination of trivalent gallium(3+) (log beta110 ~ 27.6).	PMID:25087170 reference PMID:25087170 evidence type PRIMARY_EXPERIMENT notes Linear tris-hydroxamate desferrioxamines form stable 1:1 Ga(III) complexes.
desferrioxamine G	chelates	cobalt(2+)	[CMM] Secondary in vitro coordination of divalent cobalt(2+).	PMID:22641620 reference PMID:22641620 evidence type PRIMARY_EXPERIMENT notes Chelation of Co(II) by linear tris-hydroxamate desferrioxamines.
desferrioxamine G	chelates	nickel(2+)	[CMM] Secondary in vitro coordination of divalent nickel(2+).	PMID:22641620 reference PMID:22641620 evidence type PRIMARY_EXPERIMENT notes Chelation of Ni(II) by linear tris-hydroxamate desferrioxamines.
desferrioxamine G	chelates	lanthanum(3+)	[CMM] Secondary in vitro coordination of trivalent rare earth lanthanum(3+).	PMID:38004684 reference PMID:38004684 evidence type PRIMARY_EXPERIMENT notes Hydroxamate metallophore coordination of rare earth elements including La(III).

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

Molecular targets 6

Target	Target organism	Measurement	Evidence
iron(3+) OTHER BINDS Primary physiological ferric ion chelation via hexadentate tris-hydroxamate coordination (ferrioxamine G1, 1:1 complex, log beta110 ~ 30.6) mediating high-affinity bacterial iron acquisition.			PMID:15600304 PMID:17704771 PMID:22641620 reference PMID:15600304 evidence type PRIMARY_EXPERIMENT notes Identification and genetic characterization of the desABCD desferrioxamine biosynthetic gene cluster in Streptomyces coelicolor M145 directing production of desferrioxamines G1 and E. reference PMID:17704771 evidence type PRIMARY_EXPERIMENT notes NIS synthetase DesD catalyzes the ATP-dependent condensation of N-hydroxy-N-succinylcadaverine to form both linear desferrioxamine G1 and macrocyclic desferrioxamine E for ferric iron acquisition. reference PMID:22641620 evidence type PRIMARY_EXPERIMENT notes Characterization of linear tris-hydroxamate desferrioxamine complexation with Fe(III) and divalent transition metals in aqueous solution.
gallium(3+) OTHER BINDS [Critical Mineral & Material (CMM)] Hexadentate tris-hydroxamate coordination of trivalent gallium(3+) (log beta110 ~ 27.6, measured in vitro as a redox-inactive Fe(III) surrogate; lower affinity than Fe(III) and not a physiological metabolic cofactor).			PMID:25087170 reference PMID:25087170 evidence type PRIMARY_EXPERIMENT notes Comparison of hexadentate tris-hydroxamate desferrioxamine complexation properties for trivalent Fe(III) and Ga(III) in aqueous solution.
cobalt(2+) OTHER BINDS [Critical Mineral & Material (CMM)] Coordination of divalent cobalt(2+) in aqueous solution (measured in vitro; ~15-20 orders of magnitude weaker than Fe(III), oxidation-prone to Co(III)-tris-hydroxamate in aerobic solution).			PMID:22641620 reference PMID:22641620 evidence type PRIMARY_EXPERIMENT notes Evaluation of linear tris-hydroxamate desferrioxamine chelation of divalent transition metal ions Co(II), Ni(II), Cu(II), and Zn(II) relative to Fe(III).
nickel(2+) OTHER BINDS [Critical Mineral & Material (CMM)] Coordination of divalent nickel(2+) in aqueous solution (log K ~ 10-11, measured in vitro only; secondary non-physiological binding relative to Fe(III)).			PMID:22641620 reference PMID:22641620 evidence type PRIMARY_EXPERIMENT notes Evaluation of linear tris-hydroxamate desferrioxamine chelation of Ni(II) and divalent transition metals in aqueous solution.
lanthanum(3+) OTHER BINDS [Critical Mineral & Material (CMM)] Coordination of trivalent rare earth element lanthanum(3+) in aqueous solution (log beta ~ 10-12, measured in vitro only; weaker than Fe(III) and Ga(III)).			PMID:38004684 reference PMID:38004684 evidence type PRIMARY_EXPERIMENT notes Bacterial hydroxamate siderophore and metallophore chelation activity toward rare earth elements including La(III).
copper(2+) OTHER BINDS In vitro coordination of divalent copper(2+) via hydroxamate oxygen donors (log beta ~ 14, secondary relative to Fe(III)).			PMID:22641620 reference PMID:22641620 evidence type PRIMARY_EXPERIMENT notes Evaluation of linear tris-hydroxamate desferrioxamine chelation of Cu(II) in aqueous solution.

Explore across X-Mech

AntibioticMech (desferrioxamine G) ↗ MediaIngredientMech (CHEBI:50439) ↗ TaxonMech: Streptomyces coelicolor A3(2) (NCBITaxon:100226) ↗ TaxonMech: Streptomyces coelicolor A3(2) (NCBITaxon:100226) ↗ PathwayMech (mibig:BGC0000940) ↗

Provenance

Source concept	Source	Version
CHEBI:50439	CHEBI	3-star

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