CHEBI:133861 - desferricoprogen B

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ChEBI Name desferricoprogen B
ChEBI ID CHEBI:133861
Definition A member of the class of 2,5-diketopiperazines that is 2,5-diketopiperazine which is substituted at positions 3 and 6 by 3-(hydroxyamino)propyl groups in which the nitrogens have been acylated by (2E)-5-hydroxy-3-methylpent-2-enoyl groups. The substituent at position 3 has been further modified by having its terminal hydroxy group esterified by condensation with the carboxy group of N5-hydroxy-L-ornithine in which the N5 nitrogen has been acylated by a (2E)-5-hydroxy-3-methylpent-2-enoyl group.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Julian Brandl
Supplier Information
Download Molfile XML SDF
Formula C33H54N6O12
Net Charge 0
Average Mass 726.816
Monoisotopic Mass 726.37997
InChI InChI=1S/C33H54N6O12/c1-22(10-16-40)19-28(42)37(48)13-4-7-25(34)33(47)51-18-12-24(3)21-30(44)39(50)15-6-9-27-32(46)35-26(31(45)36-27)8-5-14-38(49)29(43)20-23(2)11-17-41/h19-21,25-27,40-41,48-50H,4-18,34H2,1-3H3,(H,35,46)(H,36,45)/b22-19+,23-20+,24-21+/t25-,26-,27-/m0/s1
InChIKey XRSRJBBRTCEBNS-CAGSISFISA-N
SMILES C(CN(C(/C=C(/CCO)\C)=O)O)C[C@@H](C(=O)OCC/C(/C)=C/C(=O)N(O)CCC[C@@]1(NC([C@](CCCN(C(/C=C(/CCO)\C)=O)O)(NC1=O)[H])=O)[H])N
Metabolite of Species Details
Aspergillus niger (NCBI:txid5061) of strain N402 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.
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing desferricoprogen B (CHEBI:133861) has role siderophore (CHEBI:26672)
desferricoprogen B (CHEBI:133861) is a 2,5-diketopiperazines (CHEBI:65061)
desferricoprogen B (CHEBI:133861) is a carboxylic ester (CHEBI:33308)
desferricoprogen B (CHEBI:133861) is a homoallylic alcohol (CHEBI:134362)
desferricoprogen B (CHEBI:133861) is a hydroxamic acid (CHEBI:24650)
desferricoprogen B (CHEBI:133861) is a primary alcohol (CHEBI:15734)
desferricoprogen B (CHEBI:133861) is a primary amino compound (CHEBI:50994)
desferricoprogen B (CHEBI:133861) is conjugate acid of desferricoprogen B(3−) (CHEBI:133862)
Incoming desferricoprogen B(3−) (CHEBI:133862) is conjugate base of desferricoprogen B (CHEBI:133861)
IUPAC Name
(3E)-5-(hydroxy{3-[(2S,5S)-5-(3-{hydroxy[(2E)-5-hydroxy-3-methylpent-2-enoyl]amino}propyl)-3,6-dioxopiperazin-2-yl]propyl}amino)-3-methyl-5-oxopent-3-en-1-yl N5-hydroxy-N5-[(2E)-5-hydroxy-3-methylpent-2-enoyl]-L-ornithinate
Citations Waiting for Citations Types Sources
20376388 PubMed citation SUBMITTER
2950205 PubMed citation Europe PMC
Last Modified
03 March 2017