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discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound: petrobactin

Superclasses: a secondary metabolite a siderophore a catecholate siderophore
an alcohol a diol a benzenediol a catechol a catecholate siderophore
an aromatic compound a benzenediol a catechol a catecholate siderophore

Citations: [Wilson06]

Chemical Formula: C34H51N6O11

Molecular Weight: 719.81 Daltons

Monoisotopic Molecular Weight: 718.3537564793 Daltons

SMILES: C([N+]CCCCNC(=O)CC(C(=O)[O-])(O)CC(=O)NCCCC[N+]CCCNC(C1(C=CC(O)=C(O)C=1))=O)CCNC(C2(C=CC(O)=C(O)C=2))=O

InChI: InChI=1S/C34H50N6O11/c41-25-9-7-23(19-27(25)43)31(47)39-17-5-13-35-11-1-3-15-37-29(45)21-34(51,33(49)50)22-30(46)38-16-4-2-12-36-14-6-18-40-32(48)24-8-10-26(42)28(44)20-24/h7-10,19-20,35-36,41-44,51H,1-6,11-18,21-22H2,(H,37,45)(H,38,46)(H,39,47)(H,40,48)(H,49,50)/p+1

InChIKey: InChIKey=GKIMOVAPSAVJHZ-UHFFFAOYSA-O

Unification Links: PubChem:44229176

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 217.23509 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

Not in pathways:
a catechol + S-adenosyl-L-methionine → a guaiacol + S-adenosyl-L-homocysteine + H+


4 a benzenediol + oxygen → 4 a benzosemiquinone + 2 H2O

Reactions known to produce the compound:

petrobactin biosynthesis :
N1-(3,4-dihydroxybenzoyl)-N8,N'8-citryl-bis(spermidine) + a 3,4-DHB-AsbD protein → petrobactin + H2O

ethylene biosynthesis III (microbes) , iron reduction and absorption :
an Fe(II)-siderophore + H+a siderophore + Fe2+

Not in pathways:
2 Fe2+ + 2 a siderophore + NADP+ + H+ ← 2 an Fe(III)-siderophore + NADPH

β-D-glucuronide and D-glucuronate degradation :
a β-D-glucuronoside + H2O → D-glucopyranuronate + an alcohol

glycerophosphodiester degradation :
a glycerophosphodiester + H2O → an alcohol + sn-glycerol 3-phosphate + H+

phosphate acquisition , phosphate utilization in cell wall regeneration :
a phosphate monoester + H2O ↔ an alcohol + phosphate


an alcohol + NAD+ + H2O ← an organic hydroperoxide + NADH + H+
an α-D-glucuronoside + H2O → D-glucopyranuronate + an alcohol
an α amino acid ester + H2O → an alcohol + an α amino acid + H+
a phosphate monoester + H2O → an alcohol + phosphate
RH + a reduced [NADPH-hemoprotein reductase] + oxygen → ROH + an oxidized [NADPH-hemoprotein reductase] + H2O
an oligosaccharide with β-L-arabinopyranose at the non-reducing end + H2O → β-L-arabinopyranose + an alcohol
an N-acetyl-β-D-hexosaminide + H2O → an N-acetyl-β-D-hexosamine + an alcohol
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an acetic ester + H2O → an alcohol + acetate + H+
a reduced thioredoxin + an organic hydroperoxide → an oxidized thioredoxin + an alcohol + H2O
a 6-O-(β-D-xylopyranosyl)-β-D-glucopyranoside + H2O → β-primeverose + an alcohol
an organic molecule + H2O + 2 oxygen → an alcohol + 2 superoxide + 2 H+
an N5-acyl-L-ornithine-ester + H2O → an N5-acyl-L-ornithine + an alcohol
α-L-fucoside + H2O → L-fucopyranose + an alcohol
a 2-deoxy-α-D-glucoside + H2O → 2-deoxy-D-glucose + an alcohol
a 6-phospho-β-D-galactoside + H2O → α-D-galactose 6-phosphate + an alcohol

In Reactions of unknown directionality:

Not in pathways:
an alcohol + 3'-phosphoadenylyl-sulfate = adenosine 3',5'-bisphosphate + an organosulfate + H+
an alcohol + NAD(P)+ = an aldehyde + NAD(P)H + H+
an alcohol + NADP+ = an aldehyde + NADPH + H+
trans-cinnamoyl-β-D-glucoside + an alcohol = β-D-glucose + alkyl cinnamate
an alcohol + acetyl-CoA = an acetic ester + coenzyme A
2 protein cysteines + an organic hydroperoxide = a protein disulfide + an alcohol + H2O
an organic molecule + an organic hydroperoxide = 2 an alcohol
an organic molecule + hydrogen peroxide = an alcohol + H2O

Enzymes activated by petrobactin, sorted by the type of activation, are:

Activator (Mechanism unknown) of: phosphoenolpyruvate carboxylase [Izui83]


References

Izui83: Izui K, Matsuda Y, Kameshita I, Katsuki H, Woods AE (1983). "Phosphoenolpyruvate carboxylase of Escherichia coli. Inhibition by various analogs and homologs of phosphoenolpyruvate." J Biochem (Tokyo) 1983;94(6);1789-95. PMID: 6368527

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Wilson06: Wilson MK, Abergel RJ, Raymond KN, Arceneaux JE, Byers BR (2006). "Siderophores of Bacillus anthracis, Bacillus cereus, and Bacillus thuringiensis." Biochem Biophys Res Commun 348(1);320-5. PMID: 16875672


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Wed Nov 26, 2014, biocyc13.