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MetaCyc Compound: benzaldehyde

Synonyms: benzanoaldehyde

Superclasses: an aldehyde or ketone an aldehyde an aryl aldehyde
an aromatic compound an aryl aldehyde

Chemical Formula: C7H6O

Molecular Weight: 106.12 Daltons

Monoisotopic Molecular Weight: 106.04186481469999 Daltons

benzaldehyde compound structure

SMILES: C(=O)C1(=CC=CC=C1)

InChI: InChI=1S/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H

InChIKey: InChIKey=HUMNYLRZRPPJDN-UHFFFAOYSA-N

Unification Links: CAS:100-52-7 , ChEBI:17169 , ChemSpider:235 , HMDB:HMDB06115 , KEGG:C00261 , MetaboLights:MTBLC17169 , PubChem:240

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 61.276726 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

mandelate degradation I :
benzaldehyde + NADP+ + H2O → benzoate + NADPH + 2 H+

salicin biosynthesis :
benzaldehyde → salicylaldehyde

salicortin biosynthesis :
benzaldehyde + 2 NADPH + 2 oxygen + H+ → 6-hydroxy-2-cyclohexen-one-carboxylate + 2 NADP+ + H2O

Not in pathways:
benzaldehyde + oxygen + H2O → benzoate + hydrogen peroxide + H+

Not in pathways:
an aryl aldehyde + oxygen + H2O → an aromatic carboxylate + hydrogen peroxide

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:

amygdalin and prunasin degradation , vicianin bioactivation :
(R)-mandelonitrile → hydrogen cyanide + benzaldehyde

benzoate biosynthesis II (CoA-independent, non-β-oxidative) :
3-hydroxy-3-phenylpropanoate → benzaldehyde + acetate

benzoate biosynthesis III (CoA-dependent, non-β-oxidative) :
3-hydroxy-3-phenylpropanoyl-CoA → benzaldehyde + acetyl-CoA

mandelate degradation I :
phenylglyoxylate + H+ → CO2 + benzaldehyde

Not in pathways:
an aromatic primary alcohol + oxygen → hydrogen peroxide + an aryl aldehyde

ceramide degradation :
a sphingoid 1-phosphate → phosphoryl-ethanolamine + 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:

benzoate biosynthesis II (CoA-independent, non-β-oxidative) , benzoate biosynthesis III (CoA-dependent, non-β-oxidative) , mandelate degradation I :
benzaldehyde + NAD+ + H2O ↔ benzoate + NADH + 2 H+

salicin biosynthesis :
benzyl alcohol + NAD+benzaldehyde + NADH + H+
benzaldehyde + NAD+ + H2O ↔ benzoate + NADH + 2 H+

salicortin biosynthesis :
benzyl alcohol + NAD+benzaldehyde + NADH + H+
benzaldehyde + NAD+ + H2O ↔ benzoate + NADH + 2 H+

toluene degradation to benzoate :
benzyl alcohol + NAD+benzaldehyde + NADH + H+
benzaldehyde + NAD+ + H2O ↔ benzoate + NADH + 2 H+

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

In Reactions of unknown directionality:

Not in pathways:
L-threo-3-phenylserine = benzaldehyde + glycine
benzoin = 2 benzaldehyde

Not in pathways:
an aryl aldehyde + NAD+ + H2O = an aromatic carboxylate + NADH + H+
AMP + an aryl aldehyde + NADP+ + diphosphate = ATP + an aromatic carboxylate + NADPH
an arylkylamine + 2 an oxidized azurin + H2O = an aryl aldehyde + ammonium + 2 a reduced azurin
a phenol + NAD+ = an aryl aldehyde + NADH + H+
an aromatic (S)-hydroxynitrile = hydrogen cyanide + an aryl aldehyde
a phenol + NADP+ = an aryl aldehyde + NADPH + H+

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 unknown oxidized electron acceptor + H2O = a carboxylate + an unknown reduced 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 unknown oxidized electron acceptor = an aldehyde + an unknown reduced 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 benzaldehyde, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: betaine aldehyde dehydrogenase [Falkenberg90] , acetaldehyde dehydrogenase [Shone81, Comment 1]

Inhibitor (Mechanism unknown) of: benzylsuccinate synthase [Biegert96]

Inhibitor (Other types) of: benzaldehyde dehydrogenase [Long09]

This compound has been characterized as an alternative substrate of the following enzymes: 4-nitrobenzaldehyde dehydrogenase (NAD+-linked) , vanillin dehydrogenase , 3-hydroxypropionaldehyde dehydrogenase , (3-methylbenzyl)succinate synthase , benzylsuccinate synthase , D-glucuronate reductase , NAD+ L-lactaldehyde dehydrogenase , 4-sulfoacetophenone monooxygenase , 2-aminomucoate semialdehyde dehydrogenase , NADP+-benzaldehyde dehydrogenase , α-ketoglutaric semialdehyde dehydrogenase , 2-hydroxymuconate 6-semialdehyde dehydrogenase , NADP+-dependent succinate-semialdehyde dehydrogenase , indole-3-acetaldehyde oxidase , perillyl aldehyde monooxygenase , vanillin dehydrogenase


References

Biegert96: Biegert T, Fuchs G, Heider J (1996). "Evidence that anaerobic oxidation of toluene in the denitrifying bacterium Thauera aromatica is initiated by formation of benzylsuccinate from toluene and fumarate." Eur J Biochem 1996;238(3);661-8. PMID: 8706665

Falkenberg90: Falkenberg P, Strom AR (1990). "Purification and characterization of osmoregulatory betaine aldehyde dehydrogenase of Escherichia coli." Biochim Biophys Acta 1990;1034(3);253-9. PMID: 2194570

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

Long09: Long MC, Nagegowda DA, Kaminaga Y, Ho KK, Kish CM, Schnepp J, Sherman D, Weiner H, Rhodes D, Dudareva N (2009). "Involvement of snapdragon benzaldehyde dehydrogenase in benzoic acid biosynthesis." Plant J 59(2);256-65. PMID: 19292760

Shone81: Shone CC, Fromm HJ (1981). "Steady-state and pre-steady-state kinetics of coenzyme A linked aldehyde dehydrogenase from Escherichia coli." Biochemistry 1981;20(26);7494-501. PMID: 7034777


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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 Thu Mar 26, 2015, biocyc13.