desferrimycobactin T
CHEBI:61168 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 cyclic hydroxamic acid secreted by Mycobacterium tuberculosis which is lipid-soluble and acts as a siderophore.
Structure
| Standard InChIKey | FLJNVPAGIYBTDU-XWINOZFQSA-N |
|---|---|
| SMILES | CCCCCCCCCCCCCCCCCCCC(=O)N(O)CCCC[C@H](NC(=O)[C@@H]1COC(c2ccccc2O)=N1)C(=O)O[C@H](C)CC(=O)N[C@H]1CCCCN(O)C1=O |
| Stereochemistry | fully defined |
Filing pathway
Unclassified — 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, pks, 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 |
|---|---|---|---|
| Mycobacterium tuberculosis H37Rv Strain: H37Rv NCBITaxon:83332 |
BGC_CHARACTERIZED | mibig:BGC0001021 | PMID:9831524
|
| Mycobacterium tuberculosis H37Rv Strain: H37Rv NCBITaxon:83332 |
BGC_CHARACTERIZED | mibig:BGC0001021 | PMID:10655517
|
Occurrences 0
None cited.
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0001021 | Mycobacterium tuberculosis H37Rv NCBITaxon:83332 |
CLUSTER_DEMONSTRATED | genbank:AL123456.3 |
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 | MbtI (salicylate synthase) and MbtA (salicyl-AMP ligase) | CHEBI:17333 → CHEBI:16914 | PMID:9831524 | |
| 2 | MbtB, MbtE, MbtF (NRPS), MbtC, MbtD (PKS), MbtG (lysine N6-monooxygenase), and MbtK (acyltransferase) | CHEBI:16914 + CHEBI:17115 + CHEBI:18019 → CHEBI:61168 | PMID:9831524 |
Step 1: Conversion of chorismic acid to salicylic acid by MbtI and ATP-dependent adenylation to salicyl-AMP by MbtA for loading onto the aryl carrier domain of MbtB.
Step 2: Hybrid NRPS-PKS assembly of the phenyloxazoline-peptidyl-polyketide core and N6-hydroxylation/acylation of L-lysine residues to yield cell-envelope-associated lipophilic desferrimycobactin T.
Mechanism & Biosynthesis Overview
Causal graph — bioactivity 8 nodes, 7 edges
Hybrid NRPS-PKS biosynthesis of desferrimycobactin T by the mbtA-J locus (BGC0001021) in Mycobacterium tuberculosis and hexadentate chelation of Fe(III) and CMM cations Ga(III) and VO(2+).
| Subject | Predicate | Object | Notes | Evidence |
|---|---|---|---|---|
| salicylic acid | substrate_of | mbtA-J biosynthetic gene cluster (BGC0001021) | MbtA activates salicylic acid as salicyl-AMP to initiate mycobactin T assembly. | PMID:9831524
|
| L-lysine | substrate_of | mbtA-J biosynthetic gene cluster (BGC0001021) | Two L-lysine residues are N6-hydroxylated by MbtG to form the internal linear and cyclic hydroxamate ligands. | PMID:9831524
|
| mbtA-J biosynthetic gene cluster (BGC0001021) | synthesizes | desferrimycobactin T | MbtA-J NRPS-PKS assembly line produces desferrimycobactin T. | PMID:9831524
|
| desferrimycobactin T | chelates | iron(3+) | Hexadentate coordination of Fe(III) by phenolate, oxazoline N, and two hydroxamates. | PMID:8666910
|
| iron(3+) | enables | iron ion transport | Delivers host iron across the mycobacterial cell envelope during intracellular infection. | PMID:10655517
|
| desferrimycobactin T | chelates | gallium(3+) | [CMM] Coordinates trivalent gallium(3+) as a redox-inactive ferric surrogate. | PMID:10992462
|
| desferrimycobactin T | chelates | oxidovanadium(2+) | [CMM] In vitro coordination of oxidovanadium(2+). | PMID:9831524
|
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 Primary physiological ferric ion chelation via hexadentate 2-hydroxyphenyloxazoline + bis-hydroxamate coordination (mycobactin T, 1:1 complex, Ka ~ 10^30 M^-1) essential for Mycobacterium tuberculosis iron acquisition in macrophages. |
PMID:9831524 |
||
| gallium(3+) OTHER BINDS [Critical Mineral & Material (CMM)] Hexadentate coordination of trivalent gallium(3+) forming Ga(III)-mycobactin T; exploited as a redox-inactive Fe(III) mimic that disrupts Mycobacterium tuberculosis iron-dependent enzymes. |
PMID:10992462 |
||
| oxidovanadium(2+) OTHER BINDS [Critical Mineral & Material (CMM)] In vitro coordination of vanadyl / oxidovanadium(2+) by the phenolate-oxazoline-hydroxamate donor set of mycobactin (non-physiological coordination complex). |
PMID:9831524
|
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Provenance
| Source concept | Source | Version |
|---|---|---|
| CHEBI:61168 | CHEBI | 3-star |
This page is generated from data/natural_products/unclassified/desferrimycobactin-t.yaml, which is generated from the committed inventories. Neither is edited by hand.