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CHEBI:133861 - desferricoprogen B

ChEBI IDCHEBI:133861
ChEBI Namedesferricoprogen B
Stars
DefinitionA 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.
Last Modified3 March 2017
SubmitterJubra
DownloadsMolfile
FormulaC33H54N6O12
Net Charge0
Average Mass726.825
Monoisotopic Mass726.37997
SMILES[H][C@@]1(CCCN(O)C(=O)/C=C(\C)CCO)NC(=O)[C@]([H])(CCCN(O)C(=O)/C=C(\C)CCOC(=O)[C@@H](N)CCCN(O)C(=O)/C=C(\C)CCO)NC1=O
InChIInChI=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
InChIKeyXRSRJBBRTCEBNS-CAGSISFISA-N
Species of MetaboliteComponentSourceComments
Aspergillus niger (ncbitaxon:5061) - PubMed (25062661) Strain: N402
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.
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
siderophore  Any of low-molecular-mass iron(III)-chelating compounds produced by microorganisms for the purpose of the transport and sequestration of iron.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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