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CHEBI:4356 - desferrioxamine B

ChEBI IDCHEBI:4356
ChEBI Namedesferrioxamine B
Stars
DefinitionAn 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.
Last Modified27 May 2021
DownloadsMolfile
FormulaC25H48N6O8
Net Charge0
Average Mass560.693
Monoisotopic Mass560.35336
SMILESCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCN
InChIInChI=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)
InChIKeyUBQYURCVBFRUQT-UHFFFAOYSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Streptomyces sviceus (ncbitaxon:285530) - PubMed (33784308)
Streptomyces pilosus (ncbitaxon:28893) - PubMed (30701380)
Roles Classification
Chemical Roles:
siderophore  Any of low-molecular-mass iron(III)-chelating compounds produced by microorganisms for the purpose of the transport and sequestration of iron.
Biological Roles:
siderophore  Any of low-molecular-mass iron(III)-chelating compounds produced by microorganisms for the purpose of the transport and sequestration of iron.
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
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.
ChEBI Ontology
Outgoing Relation(s)
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)
desferrioxamine B (CHEBI:4356) is conjugate base of desferrioxamine B(1+) (CHEBI:195191)
Incoming Relation(s)
desferrioxamine B mesylate (CHEBI:31460) has part desferrioxamine B (CHEBI:4356)
desferrioxamine B(1+) (CHEBI:195191) is conjugate acid of 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  Source
deferoxaminumWHO MedNet
deferoxaminaWHO MedNet
deferoxamineWHO MedNet
déferoxamineWHO MedNet
Synonyms  Source
DeferrioxamineDrugBank
DeferoxaminDrugBank
DFODrugBank
DesferrioxamineDrugBank
deferrioxamine BChemIDplus
DFOBChEBI
Manual XrefsDatabases
C06940KEGG COMPOUND
D03670KEGG DRUG
DB00746DrugBank
BE609053Patent
DeferoxamineWikipedia
LSM-6541LINCS
792DrugCentral
HMDB0014884HMDB
LMFA08020169LIPID MAPS
2867ChemSpider
Registry NumbersSources
Beilstein:2514118Beilstein
CAS:70-51-9NIST Chemistry WebBook
CAS:70-51-9ChemIDplus
Citations