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CHEBI:83125 - desferricoprogen

ChEBI IDCHEBI:83125
ChEBI Namedesferricoprogen
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 N2-acetyl-N5-hydroxy-L-ornithine in which the N5 nitrogen has been acylated by a (2E)-5-hydroxy-3-methylpent-2-enoyl group.
Last Modified1 March 2017
SubmitterGareth Owen
DownloadsMolfile
FormulaC35H56N6O13
Net Charge0
Average Mass768.862
Monoisotopic Mass768.39054
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](CCCN(O)C(=O)/C=C(\C)CCO)NC(C)=O)NC1=O
InChIInChI=1S/C35H56N6O13/c1-23(11-17-42)20-30(45)39(51)14-5-8-27-33(48)38-28(34(49)37-27)9-6-15-40(52)32(47)22-25(3)13-19-54-35(50)29(36-26(4)44)10-7-16-41(53)31(46)21-24(2)12-18-43/h20-22,27-29,42-43,51-53H,5-19H2,1-4H3,(H,36,44)(H,37,49)(H,38,48)/b23-20+,24-21+,25-22+/t27-,28-,29-/m0/s1
InChIKeyAKLLFACZGZTMGS-FCRFISLRSA-N
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 (CHEBI:83125) has role siderophore (CHEBI:26672)
desferricoprogen (CHEBI:83125) is a 2,5-diketopiperazines (CHEBI:65061)
desferricoprogen (CHEBI:83125) is a acetamides (CHEBI:22160)
desferricoprogen (CHEBI:83125) is a carboxylic ester (CHEBI:33308)
desferricoprogen (CHEBI:83125) is a homoallylic alcohol (CHEBI:134362)
desferricoprogen (CHEBI:83125) is a hydroxamic acid (CHEBI:24650)
desferricoprogen (CHEBI:83125) is a primary alcohol (CHEBI:15734)
desferricoprogen (CHEBI:83125) is conjugate acid of desferricoprogen(3−) (CHEBI:83127)
Incoming Relation(s)
desferricoprogen(3−) (CHEBI:83127) is conjugate base of desferricoprogen (CHEBI:83125)
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 N2-acetyl-N5-hydroxy-N5-[(2E)-5-hydroxy-3-methylpent-2-enoyl]-L-ornithinate
Registry NumbersSources
Reaxys:21959939Reaxys