desferrioxamine B
CHEBI:4356 EXACT SEEDED cytotoxicenzyme inhibitor
An acyclic desferrioxamine that is butanedioic acid in which one of the carboxy groups undergoes formal condensation with the primary amino group of N-(5-aminopentyl)-N-hydroxyacetamide and the second carboxy group undergoes formal condensation with the hydroxyamino group of N1-(5-aminopentyl)-N1-hydroxy-N4-[5-(hydroxyamino)pentyl]butanediamide. It is a siderophore native to Streptomyces pilosus biosynthesised by the DesABCD enzyme cluster as a high affinity Fe(III) chelator.
Structure
| Standard InChIKey | UBQYURCVBFRUQT-UHFFFAOYSA-N |
|---|---|
| SMILES | CC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCN |
| Stereochemistry | fully defined |
| Cross-references | npatlas:NPA09012, pubchem:2973, npatlas:NPA009012 |
Filing pathway
Fatty acids — computed by NPClassifier npclassifier.gnps2.org@2026-09-07, which is why it is pinned rather than recomputed. The gene cluster's asserted class is other, from MIBiG.
Producer organisms 4
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) NCBITaxon:100226 |
BGC_CHARACTERIZED | mibig:BGC0000940 | PMID:15600304 |
| Streptomyces griseus subsp. griseus NBRC 13350 NCBITaxon:455632 |
SOURCE_ASSERTION | mibig:BGC0000941 | PMID:18375553 |
| Streptomyces argillaceus NCBITaxon:41951 |
SOURCE_ASSERTION | mibig:BGC0001453 | PMID:29795673 |
| Streptomyces sp. NCBITaxon:1931 |
SOURCE_ASSERTION | mibig:BGC0002305 | DOI:10.1016/j.tetlet.2018.11.063 |
Occurrences 25
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 |
|---|---|---|
| Streptomyces xinghaiensis NCBITaxon:1038928 |
LOTUS | DOI:10.1007/S00253-018-9337-2 |
| Moorea producens NCBITaxon:1155739 |
LOTUS | DOI:10.1021/ACS.JNATPROD.6B00051 |
| Streptomyces wadayamensis NCBITaxon:141454 |
LOTUS | DOI:10.1128/GENOMEA.00625-14 |
| Streptomyces malaysiense NCBITaxon:1428626 |
LOTUS | DOI:10.1038/SREP24247 |
| Streptomyces albidoflavus NCBITaxon:1886 |
LOTUS | DOI:10.1021/JA045774K |
| Streptomyces albidoflavus NCBITaxon:1886 |
LOTUS | DOI:10.1099/MIC.0.000524 |
| Streptomyces albidoflavus NCBITaxon:1886 |
LOTUS | DOI:10.1111/J.1742-4658.2007.05662.X |
| Streptomyces albidoflavus NCBITaxon:1886 |
LOTUS | DOI:10.1111/J.1742-4658.2009.07182.X |
| Streptomyces albidoflavus NCBITaxon:1886 |
LOTUS | DOI:10.1111/J.1751-7915.2010.00232.X |
| Streptomyces albidoflavus NCBITaxon:1886 |
LOTUS | DOI:10.1128/MBIO.00459-13 |
| Streptomyces coelicolor NCBITaxon:1902 |
LOTUS | DOI:10.1021/JA045774K |
| Streptomyces coelicolor NCBITaxon:1902 |
LOTUS | DOI:10.1099/MIC.0.000524 |
| Streptomyces coelicolor NCBITaxon:1902 |
LOTUS | DOI:10.1111/J.1742-4658.2007.05662.X |
| Streptomyces coelicolor NCBITaxon:1902 |
LOTUS | DOI:10.1111/J.1742-4658.2009.07182.X |
| Streptomyces coelicolor NCBITaxon:1902 |
LOTUS | DOI:10.1111/J.1751-7915.2010.00232.X |
| Streptomyces coelicolor NCBITaxon:1902 |
LOTUS | DOI:10.1128/MBIO.00459-13 |
| Streptomyces griseus NCBITaxon:1911 |
LOTUS | DOI:10.1128/JB.00204-08 |
| Streptomyces chartreusis NCBITaxon:1969 |
LOTUS | DOI:10.1073/PNAS.1715713115 |
| Streptomyces sviceus NCBITaxon:285530 |
CHEBI | PMID:33784308 |
| Streptomyces pilosus NCBITaxon:28893 |
LOTUS | DOI:10.1128/JB.175.11.3295-3302.1993 |
| Streptomyces pilosus NCBITaxon:28893 |
LOTUS | DOI:10.1186/1475-2859-2-5 |
| Streptomyces pilosus NCBITaxon:28893 |
LOTUS | DOI:10.3923/PJBS.2010.1151.1155 |
| Streptomyces pilosus NCBITaxon:28893 |
LOTUS | DOI:10.3923/PJBS.2010.546.550 |
| Streptomyces pilosus NCBITaxon:28893 |
CHEBI | PMID:30701380 |
| Streptomyces lydicus NCBITaxon:47763 |
LOTUS | DOI:10.1038/SREP44786 |
Biosynthetic gene clusters 4
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000940 | Streptomyces coelicolor A3(2) NCBITaxon:100226 |
CLUSTER_DEMONSTRATED | genbank:AL645882.2 |
| mibig:BGC0000941 | Streptomyces griseus subsp. griseus NBRC 13350 NCBITaxon:455632 |
CLUSTER_UNSTATED | genbank:AP009493.1 |
| mibig:BGC0001453 | Streptomyces argillaceus NCBITaxon:41951 |
CLUSTER_UNSTATED | genbank:LT989883.1 |
| mibig:BGC0002305 | Streptomyces sp. NCBITaxon:1931 |
CLUSTER_UNSTATED | genbank:MN509302.1 |
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.
Bioactivities 25
| Assay | Result | Reference |
|---|---|---|
| A quantitative high throughput screen for small molecules that induce DNA re-replication in MCF 10a normal breast cells. | 0.1458 uM | pubchem.aid:624296 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: AML-191 cell line | 8.3275 uM | pubchem.aid:2202236 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: AML-194 cell line | 9.3436 uM | pubchem.aid:2202237 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: HNT-34 cell line | 9.3436 uM | pubchem.aid:2202234 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: MV-4-11 cell line | 11.7629 uM | pubchem.aid:2202233 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: OCI-AML3 cell line | 11.7629 uM | pubchem.aid:2202232 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: SET-2 cell line | 20.9177 uM | pubchem.aid:2202231 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: UCSD-AML1 cell line | 0.8327 uM | pubchem.aid:2202235 |
| Cellular viability qHTS for adrenocortical cancer (ACC) cell line SW-13 | 28.1838 uM | pubchem.aid:1963989 |
| Cellular viability qHTS for anaplastic thyroid cancer (ATC) cell line 8505C | 17.4111 uM | pubchem.aid:2202553 |
| Cellular viability qHTS for anaplastic thyroid cancer (ATC) cell line THJ-11T | 12.3261 uM | pubchem.aid:2202552 |
| Cellular viability qHTS for anaplastic thyroid cancer (ATC) cell line THJ-16T | 13.8302 uM | pubchem.aid:2202551 |
| Cytotoxicity counterscreen for inhibitors of SARS-CoV-2 cell entry | 25.1189 uM | pubchem.aid:1645845 |
| Nrf2 qHTS screen for inhibitors | 14.581 uM | pubchem.aid:504444 |
| Primary qHTS assay for inhibitors of human arachidonate 12S-lipoxygenase (ALOX12): Round 2 | 50.1187 uM | pubchem.aid:1671190 |
| Primary qHTS assay for inhibitors of human arachidonate 12S-lipoxygenase (ALOX12): Round 2 | 50.1187 uM | pubchem.aid:1671190 |
| Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an RCH-ACV wild type WT cells (2C) | 4.6829 uM | pubchem.aid:1645877 |
| Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an RCH-ACV wild type WT cells (2C) | 4.6829 uM | pubchem.aid:1645877 |
| Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an isogenic RCH-ACV NSD2 p.E1099K mutant (9B) | 5.2543 uM | pubchem.aid:1645876 |
| Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an isogenic RCH-ACV NSD2 p.E1099K mutant (9B) | 5.2543 uM | pubchem.aid:1645876 |
| Primary qHTS to identify anti-liver cancer compounds using libraries of approved drugs and bioactive compounds | 11.2202 uM | pubchem.aid:2202548 |
| Primary qHTS to identify inhibitors of SARS-CoV-2 cell entry | 17.7828 uM | pubchem.aid:1645846 |
| Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) drug resistant MV4-11 cells | 5.8954 uM | pubchem.aid:1963824 |
| Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) drug resistant MV4-11 cells | 5.8954 uM | pubchem.aid:1963824 |
| Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) naive MV4-11 cells | 6.6148 uM | pubchem.aid:1963823 |
Open questions 2
name-disagreement — ChEBI calls this structure 'desferrioxamine B' and MIBiG calls it 'desferrioxamin B'. They share a Standard InChIKey, so if the names denote different compounds then one upstream record has the wrong structure. Check which.
shared-structure — This structure is reported by more than one MIBiG entry: BGC0000940, BGC0000941, BGC0001453, BGC0002305. Confirm they describe the same compound rather than an upstream cross-reference error.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000940 | MIBIG | 5 |
| BGC0000941 | MIBIG | 3 |
| BGC0001453 | MIBIG | 5 |
| BGC0002305 | MIBIG | 2 |
| CHEBI:4356 | CHEBI | 3-star |
This page is generated from data/natural_products/fatty_acids/desferrioxamine-b.yaml, which is generated from the committed inventories. Neither is edited by hand.