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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
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MetaCyc Compound: neral

Synonyms: cis-citral, neroli aldehyde

Superclasses: a lipid an isoprenoid a terpenoid a terpenoid derivative a monoterpenoid derivative a monoterpenol
a secondary metabolite a terpenoid a terpenoid derivative a monoterpenoid derivative a monoterpenol
an alcohol a monoterpenol

Citations: [Iijima06]

Chemical Formula: C10H16O

Molecular Weight: 152.24 Daltons

Monoisotopic Molecular Weight: 152.1201151357 Daltons

SMILES: CC(C)=CCCC(C)=CC=O

InChI: InChI=1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7-

InChIKey: InChIKey=WTEVQBCEXWBHNA-YFHOEESVSA-N

Unification Links: ChEBI:29020 , ChemSpider:558878 , HMDB:HMDB35092 , KEGG:C09847 , LIPID MAPS:LMPR0102010006 , MetaboLights:MTBLC29020 , PubChem:643779

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 181.67793 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

geraniol and nerol degradation :
neral + H2O → sulcatone + acetaldehyde

linoleate biosynthesis I (plants) :
oleoyl-CoA + a lipid + H+ → a lipid oleoyl-group + coenzyme A

Reactions known to produce the compound:

Not in pathways:
a monoterpenyl diphosphate + H2O → a monoterpenol + diphosphate + H+

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

glutathione redox reactions I :
a lipid hydroperoxide + 2 glutathione + H+a lipid + glutathione disulfide + 2 H2O

Reactions known to both consume and produce the compound:

geraniol and geranial biosynthesis :
geranial ↔ neral

geraniol and nerol degradation :
geranial ↔ neral
nerol + NAD+neral + NADH + H+

In Reactions of unknown directionality:

Not in pathways:
a monoterpenol + acetyl-CoA + H+ = a monoterpenol acetate ester + coenzyme A


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 neral, sorted by the type of activation, are:

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


References

Iijima06: Iijima Y, Wang G, Fridman E, Pichersky E (2006). "Analysis of the enzymatic formation of citral in the glands of sweet basil." Arch Biochem Biophys 448(1-2);141-9. PMID: 16150417

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."


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 Mon Dec 22, 2014, biocyc13.