CHEBI:4356 - desferrioxamine B

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ChEBI Name desferrioxamine B
ChEBI ID CHEBI:4356
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C25H48N6O8
Net Charge 0
Average Mass 560.693
Monoisotopic Mass 560.35336
InChI InChI=1S/C25H48N6O8/c1-21(32)29(37)18-9-3-6-16-27-22(33)12-14-25(36)31(39)20-10-4-7-17-28-23(34)11-13-24(35)30(38)19-8-2-5-15-26/h37-39H,2-20,26H2,1H3,(H,27,33)(H,28,34)
InChIKey UBQYURCVBFRUQT-UHFFFAOYSA-N
SMILES CC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCN
Metabolite of Species Details
Streptomyces sviceus (NCBI:txid285530) See: PubMed
Streptomyces pilosus (NCBI:txid28893) See: PubMed
Roles Classification
Chemical Role(s): siderophore
Any of low-molecular-mass iron(3)-chelating compounds produced by microorganisms for the purpose of the transport and sequestration of iron.
iron chelator

Biological Role(s): siderophore
Any of low-molecular-mass iron(3)-chelating compounds produced by microorganisms for the purpose of the transport and sequestration of iron.
ferroptosis inhibitor
Any substance that inhibits the process of ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
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ChEBI Ontology
Outgoing desferrioxamine B (CHEBI:4356) has role bacterial metabolite (CHEBI:76969)
desferrioxamine B (CHEBI:4356) has role ferroptosis inhibitor (CHEBI:173084)
desferrioxamine B (CHEBI:4356) has role iron chelator (CHEBI:38157)
desferrioxamine B (CHEBI:4356) has role siderophore (CHEBI:26672)
desferrioxamine B (CHEBI:4356) is a acyclic desferrioxamine (CHEBI:50454)
desferrioxamine B (CHEBI:4356) is conjugate acid of desferrioxamine B(3−) (CHEBI:84700)
Incoming desferrioxamine B mesylate (CHEBI:31460) has part desferrioxamine B (CHEBI:4356)
desferrioxamine B(3−) (CHEBI:84700) is conjugate base of desferrioxamine B (CHEBI:4356)
IUPAC Name
N'-{5-[acetyl(hydroxy)amino]pentyl}-N-(5-{4-[(5-aminopentyl)(hydroxy)amino]-4-oxobutanamido}pentyl)-N-hydroxybutanediamide
INNs Sources
deferoxamina WHO MedNet
déferoxamine WHO MedNet
deferoxamine WHO MedNet
deferoxaminum WHO MedNet
Synonyms Sources
Deferoxamin DrugBank
Deferrioxamine DrugBank
deferrioxamine B ChemIDplus
Desferrioxamine DrugBank
desferrioxamine-B ChEBI
DFO DrugBank
DFOB ChEBI
N4-{5-[acetyl(hydroxy)amino]pentyl}-N1-(5-{4-[(5-aminopentyl)(hydroxy)amino]-4-oxobutanamido}pentyl)-N1-hydroxybutanediamide IUPAC
Manual Xrefs Databases
2867 ChemSpider
792 DrugCentral
BE609053 Patent
C06940 KEGG COMPOUND
D03670 KEGG DRUG
DB00746 DrugBank
Deferoxamine Wikipedia
HMDB0014884 HMDB
LMFA08020169 LIPID MAPS
LSM-6541 LINCS
View more database links
Registry Numbers Types Sources
2514118 Beilstein Registry Number Beilstein
70-51-9 CAS Registry Number NIST Chemistry WebBook
70-51-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11239825 PubMed citation Europe PMC
18536609 PubMed citation Europe PMC
28156129 PubMed citation Europe PMC
28285915 PubMed citation Europe PMC
28318697 PubMed citation Europe PMC
28455567 PubMed citation Europe PMC
29182270 PubMed citation Europe PMC
30701380 PubMed citation Europe PMC
31035197 PubMed citation Europe PMC
31229836 PubMed citation Europe PMC
31846315 PubMed citation Europe PMC
32039778 PubMed citation Europe PMC
32572744 PubMed citation Europe PMC
32734456 PubMed citation Europe PMC
32856363 PubMed citation Europe PMC
33784308 PubMed citation Europe PMC
Last Modified
27 May 2021