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MetaCyc Compound: acrolein

Synonyms: prop-2-enal, acrylaldehyde, 2-propenal

Superclasses: an aldehyde or ketone an aldehyde an alpha,beta-unsaturated aldehyde
an aldehyde or ketone an alpha,beta-unsaturated carbonyl compound an alpha,beta-unsaturated aldehyde

Chemical Formula: C3H4O

Molecular Weight: 56.064 Daltons

Monoisotopic Molecular Weight: 56.026214750499996 Daltons

acrolein compound structure

SMILES: C=C[CH]=O

InChI: InChI=1S/C3H4O/c1-2-3-4/h2-3H,1H2

InChIKey: InChIKey=HGINCPLSRVDWNT-UHFFFAOYSA-N

Unification Links: CAS:107-02-8 , ChEBI:15368 , ChemSpider:7559 , HMDB:HMDB41822 , KEGG:C01471 , NCI:8819 , PubChem:7847

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 28.804485 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

detoxification of reactive carbonyls in chloroplasts :
allyl alcohol + NADP+acrolein + NADPH + H+
acrolein + NADPH + H+ → propanal + NADP+

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 + FMNH2 + oxygen → hν + a carboxylate + FMN + H2O + 2 H+
an aldehyde + oxygen + H2O → a carboxylate + hydrogen peroxide + H+

Reactions known to produce the compound:

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[periplasmic space] + H2O[periplasmic space] + oxygen[periplasmic space]an aldehyde[periplasmic space] + ammonium[periplasmic space] + hydrogen peroxide[periplasmic space]
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:
pyruvate + an α,β-unsaturated aldehyde + H+ = a (3R,4E)-3-hydroxy-2-keto-alk-4-ene + CO2

Not in pathways:
pyruvate + an α,β-unsaturated carbonyl compound + H+ = CO2 + an n-acetyl-(n-2)-oxo-compound

Not in pathways:
an aldehyde + NAD(P)+ + H2O = a carboxylate + NAD(P)H + 2 H+
an aldehyde + 2 an oxidized ferredoxin + H2O = a carboxylate + 2 a reduced ferredoxin + 3 H+
an aldehyde + an oxidized unknown electron acceptor + H2O = a carboxylate + an reduced unknown electron acceptor + H+
an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]
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

This compound has been characterized as an alternative substrate of the following enzymes: fuculose-1-phosphate aldolase , lactaldehyde dehydrogenase


References

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 19.0 on Wed Aug 5, 2015, BIOCYC13A.