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MetaCyc Compound: hexanal

Synonyms: hexaldehyde

Superclasses: an aldehyde or ketonean aldehydean n-alkanal

Chemical Formula: C6H12O

Molecular Weight: 100.16 Daltons

Monoisotopic Molecular Weight: 100.0888150073 Daltons

hexanal compound structure

SMILES: CCCCC[CH]=O

InChI: InChI=1S/C6H12O/c1-2-3-4-5-6-7/h6H,2-5H2,1H3

InChIKey: InChIKey=JARKCYVAAOWBJS-UHFFFAOYSA-N

Unification Links: CAS:66-25-1, ChEBI:121338, ChemSpider:5949, HMDB:HMDB05994, PubChem:6184

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): 95.68345Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

pyruvate fermentation to hexanol :
1-hexanol + NAD+hexanal + NADH + H+

NAD/NADP-NADH/NADPH mitochondrial interconversion (yeast) :
an aldehyde + NAD+ + H2O → a carboxylate + NADH + 2 H+
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+

Not in pathways:
an aldehyde + oxygen + H2O → a carboxylate + hydrogen peroxide + H+

Reactions known to produce the compound:

pyruvate fermentation to hexanol :
hexanal + coenzyme A + NAD(P)+ ← hexanoyl-CoA + NAD(P)H + H+

traumatin and (Z)-3-hexen-1-yl acetate biosynthesis :
(13S)-HPODE → (9Z)-12-oxo-dodec-9-enoate + hexanal

8-amino-7-oxononanoate biosynthesis II :
a long-chain acyl-[acyl-carrier protein] + 2 a reduced flavodoxin + 3 oxygen → a pimeloyl-[acp] + an n-alkanal + 2 an oxidized flavodoxin + 3 H2O + H+

Not in pathways:
a 7,8-dihydroxy-long-chain acyl-[acp] + a reduced flavodoxin + oxygen → 7-oxoheptanoyl-[acyl-carrier-protein] + an n-alkanal + an oxidized flavodoxin + 2 H2O

ceramide degradation :
a sphingoid 1-phosphate → O-phosphoethanolamine + an aldehyde

two-component alkanesulfonate monooxygenase :
an alkylsulfonate + FMNH2 + oxygen → an aldehyde + sulfite + FMN + H2O + 2 H+

Not in pathways:
a primary amine[periplasm] + H2O[periplasm] + oxygen[periplasm]an aldehyde[periplasm] + ammonium[periplasm] + hydrogen peroxide[periplasm]
an aliphatic amine + H2O + oxygen → an aldehyde + ammonium + hydrogen peroxide
a monoamine + H2O + oxygen → an aldehyde + a primary amine + hydrogen peroxide
a primary alcohol + oxygen → hydrogen peroxide + an aldehyde

Not in pathways:
a nitroalkane + oxygen + H2O → an aldehyde or ketone + nitrite + hydrogen peroxide + H+

Reactions known to both consume and produce the compound:

Not in pathways:
a primary alcohol + NAD+an aldehyde + NADH + H+

In Reactions of unknown directionality:

Not in pathways:
an n-alkanal + NAD(P)+ = an alk-2-enal + NAD(P)H + H+
an n-alkanal + NADP+ = an alk-2-enal + NADPH + H+

Not in pathways:
an aldehyde + NAD(P)+ + H2O = a carboxylate + NAD(P)H + 2 H+
an aldehyde + 2 an oxidized ferredoxin [iron-sulfur] cluster + H2O = a carboxylate + 2 a reduced ferredoxin [iron-sulfur] cluster + 3 H+
an aldehyde + an oxidized unknown electron acceptor + H2O = a carboxylate + an reduced unknown electron acceptor + H+
an aldehyde[periplasm] + FAD[periplasm] + H2O[periplasm] = a carboxylate[periplasm] + FADH2[periplasm]
an aldehyde + an electron-transfer quinone + H2O = a carboxylate + an electron-transfer quinol + H+
a primary alcohol + 2 an oxidized cytochrome cL = an aldehyde + 2 a reduced cytochrome cL + 2 H+
an aliphatic amine + an oxidized cytochrome c550 + H2O = an aldehyde + ammonium + a reduced cytochrome c550
an alkylamine + 2 an oxidized cytochrome c550 + H2O = an aldehyde + ammonium + 2 a reduced cytochrome c550
a 2-oxo carboxylate + H+ = an aldehyde + CO2
an alcohol + NADP+ = an aldehyde + NADPH + H+
a primary alcohol + an oxidized unknown electron acceptor = an aldehyde + an reduced unknown electron acceptor
an alcohol + NAD(P)+ = an aldehyde + NAD(P)H + H+
a primary alcohol + an oxidized azurin = an aldehyde + a reduced azurin
a 1-O-(alk-1-enyl)glycero-3-phosphocholine + H2O = sn-glycero-3-phosphocholine + an aldehyde
a 1-alkenylglycerophosphoethanolamine + H2O = sn-glycero-3-phosphoethanolamine + an aldehyde
a primary alcohol + 2 an oxidized cytochrome c550 = an aldehyde + 2 a reduced cytochrome c550

Enzymes inhibited by hexanal, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: ethylnitronate monooxygenase [Francis09]

This compound has been characterized as an alternative substrate of the following enzymes: NADP+-dependent aldehyde reductase, 2-aminomucoate semialdehyde dehydrogenase, α-ketoglutaric semialdehyde dehydrogenase, γ-trimethylaminobutyraldehyde dehydrogenase, isobutyraldehyde reductase, aldehyde reductase, NAD+ L-lactaldehyde dehydrogenase


References

Francis09: Francis K, Gadda G (2009). "Kinetic evidence for an anion binding pocket in the active site of nitronate monooxygenase." Bioorg Chem 37(5);167-72. PMID: 19683782

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
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