N-(2,3-dihydroxybenzoyl)-L-serine

CHEBI:17455 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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	VDTYHTVHFIIEIL-LURJTMIESA-N
SMILES	O=C(N[C@@H](CO)C(=O)O)c1cccc(O)c1O
Stereochemistry	fully defined

Filing pathway

Amino acids and peptides — 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 nrps, 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
Escherichia coli str. K-12 substr. MG1655 Strain: K-12 MG1655 NCBITaxon:511145	BGC_CHARACTERIZED	mibig:BGC0002476	PMID:4926450 reference PMID:4926450 evidence type PRIMARY_EXPERIMENT notes Isolation and structural elucidation of N-(2,3-dihydroxybenzoyl)-L-serine (DHBS) and related enterochelin conjugates produced via the entABCDEF/fes locus (mibig:BGC0002476) in Escherichia coli K-12.
Salmonella enterica Strain: LT2 NCBITaxon:28901	AXENIC_CULTURE		PMID:4905647 reference PMID:4905647 evidence type PRIMARY_EXPERIMENT notes Isolation and characterization of 2,3-dihydroxybenzoylserine secreted by iron-restricted cultures of Salmonella typhimurium and its activity in stimulating bacterial growth in serum.

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
Escherichia coli NCBITaxon:562	CHEBI	PMID:21988831

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0002476	Escherichia coli str. K-12 substr. MG1655 NCBITaxon:511145	CLUSTER_DEMONSTRATED	genbank:U00096.3

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	Reaction	Substrate → product	Evidence
1	EntB, EntE, EntF (enterobactin NRPS) and Fes / IroE (enterobactin esterases)		CHEBI:18026 + CHEBI:17115 + CHEBI:28855 → CHEBI:17455	PMID:4926450

Step 1: NRPS-catalyzed condensation of 2,3-dihydroxybenzoic acid and L-serine to form enterobactin, followed by Fes- or IroD/IroE-catalyzed trilactone ester hydrolysis (or premature thioesterase release) to yield monomeric N-(2,3-dihydroxybenzoyl)-L-serine.

Mechanism & Biosynthesis Overview

Causal graph — bioactivity 10 nodes, 9 edges

Generation of monomeric catecholate siderophore N-(2,3-dihydroxybenzoyl)-L-serine via the entABCDEF-fes gene cluster (BGC0002476) in Escherichia coli and Salmonella enterica and bidentate catecholate coordination of Fe(III), Mo(VI), and CMM cations Ga(III) and VO(2+).

Subject	Predicate	Object	Notes	Evidence
2,3-dihydroxybenzoic acid	substrate_of	entABCDEF-fes biosynthetic gene cluster (BGC0002476)	EntE activates 2,3-dihydroxybenzoic acid as 2,3-DHB-AMP.	PMID:4926450 reference PMID:4926450 evidence type PRIMARY_EXPERIMENT notes The enterobactin pathway condenses 2,3-dihydroxybenzoate with L-serine.
L-serine	substrate_of	entABCDEF-fes biosynthetic gene cluster (BGC0002476)	EntF activates L-serine and forms the amide bond with 2,3-dihydroxybenzoate.	PMID:4926450 reference PMID:4926450 evidence type PRIMARY_EXPERIMENT notes L-serine and 2,3-dihydroxybenzoate form the 2,3-dihydroxybenzoyl-L-serine monomer.
entABCDEF-fes biosynthetic gene cluster (BGC0002476)	synthesizes	enterobactin	EntB, EntE, and EntF trimerize 2,3-dihydroxybenzoyl-L-serine into cyclic enterobactin.	PMID:4926450 reference PMID:4926450 evidence type PRIMARY_EXPERIMENT notes Enterobactin is the cyclic trimer of 2,3-dihydroxybenzoyl-L-serine.
enterobactin	hydrolyzed_to	N-(2,3-dihydroxybenzoyl)-L-serine	Fes and IroE esterases hydrolyze the trilactone ring to release monomeric N-(2,3-dihydroxybenzoyl)-L-serine.	PMID:19673474 reference PMID:19673474 evidence type PRIMARY_EXPERIMENT notes Esterase cleavage of enterobactin yields linear dimers and monomeric 2,3-dihydroxybenzoyl-L-serine.
N-(2,3-dihydroxybenzoyl)-L-serine	chelates	iron(3+)	Bidentate catecholate coordination of Fe(III) in 2:1 and 3:1 complexes.	PMID:4926450 reference PMID:4926450 evidence type PRIMARY_EXPERIMENT notes Ferric complexation by N-(2,3-dihydroxybenzoyl)-L-serine.
iron(3+)	enables	siderophore transport	Ferric-DHBS complexes are imported across the outer membrane via Fiu and CirA receptors.	PMID:2139424 reference PMID:2139424 evidence type PRIMARY_EXPERIMENT notes Fiu and Cir outer membrane proteins mediate uptake of ferric 2,3-dihydroxybenzoyl-L-serine in E. coli.
N-(2,3-dihydroxybenzoyl)-L-serine	chelates	gallium(3+)	[CMM] Bidentate catecholate coordination of trivalent gallium(3+) in solution.	PMID:2942532 reference PMID:2942532 evidence type PRIMARY_EXPERIMENT notes Catecholate complexation of Ga(III) by 2,3-dihydroxybenzoylserine siderophores.
N-(2,3-dihydroxybenzoyl)-L-serine	chelates	molybdenum(6+)	Forms cis-dioxomolybdenum(VI) bis-catecholate complexes in aqueous solution.	PMID:19277875 reference PMID:19277875 evidence type PRIMARY_EXPERIMENT notes Molybdate Mo(VI) complexation by catecholate siderophores.
N-(2,3-dihydroxybenzoyl)-L-serine	chelates	oxidovanadium(2+)	[CMM] In vitro catecholate coordination of oxidovanadium(2+).	PMID:2942532 reference PMID:2942532 evidence type PRIMARY_EXPERIMENT notes Vanadyl V(IV) complexation by catecholate siderophores.

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

Molecular targets 4

Target	Target organism	Measurement	Evidence
iron(3+) OTHER BINDS Physiological ferric ion chelation via bidentate 2,3-catecholate coordination (forming 3:1 [Fe(DHBS)3]3- and 2:1 complexes in solution); imported directly via the Fiu, CirA, and FepA TonB-dependent outer-membrane receptors in Escherichia coli and Salmonella enterica.			PMID:2139424 PMID:4926450 reference PMID:2139424 evidence type PRIMARY_EXPERIMENT notes Monomeric N-(2,3-dihydroxybenzoyl)-L-serine functions as an active catecholate siderophore transported across the Escherichia coli outer membrane primarily by the Fiu and Cir receptors. reference PMID:4926450 evidence type PRIMARY_EXPERIMENT notes Isolation and structural characterization of enterochelin and N-(2,3-dihydroxybenzoyl)-L-serine conjugates from Escherichia coli and their ferric complexes.
gallium(3+) OTHER BINDS [Critical Mineral & Material (CMM)] Bidentate catecholate coordination of trivalent gallium(3+) in 3:1 [Ga(DHBS)3]3- stoichiometry (measured in vitro in aqueous solution as a diamagnetic Fe(III) analog).			PMID:2942532 reference PMID:2942532 evidence type PRIMARY_EXPERIMENT notes Characterization of catecholate coordination and bacterial transport of trivalent Ga(III) enterobactin and 2,3-dihydroxybenzoylserine complexes in Escherichia coli.
molybdenum(6+) OTHER BINDS Catecholate cis-dioxo coordination of molybdenum(6+) (molybdate, [MoO2(DHBS)2]2-, measured in vitro and in catecholate-mediated molybdate scavenging).			PMID:19277875 reference PMID:19277875 evidence type PRIMARY_EXPERIMENT notes Catecholate siderophores coordinate molybdate Mo(VI) and vanadate alongside Fe(III) via bidentate catecholate oxygen donors.
oxidovanadium(2+) OTHER BINDS [Critical Mineral & Material (CMM)] Catecholate coordination of vanadyl / oxidovanadium(2+) in aqueous solution (measured in vitro).			PMID:2942532 reference PMID:2942532 evidence type PRIMARY_EXPERIMENT notes Catecholate coordination of vanadyl V(IV) and trivalent metal ions by 2,3-dihydroxybenzoylserine-based siderophores.

Explore across X-Mech

AntibioticMech (N-(2,3-dihydroxybenzoyl)-L-serine) ↗ MediaIngredientMech (CHEBI:17455) ↗ TaxonMech: Escherichia coli str. K-12 substr. MG1655 (NCBITaxon:511145) ↗ TaxonMech: Salmonella enterica (NCBITaxon:28901) ↗ PathwayMech (mibig:BGC0002476) ↗

Provenance

Source concept	Source	Version
CHEBI:17455	CHEBI	3-star

This page is generated from data/natural_products/amino_acids_and_peptides/n-2-3-dihydroxybenzoyl-l-serine.yaml, which is generated from the committed inventories. Neither is edited by hand.