Metabolic Modeling Tutorial
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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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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

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 + NADPH + 2 oxygen + 2 H+ → 6-hydroxy-2-cyclohexen-one-carboxylate + NADP+ + H2O

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


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+


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-phenylpropionate → 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 alkanesulfonate + FMNH2 + oxygen → an aldehyde + sulfite + FMN + H2O + 2 H+


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


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


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+


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 electron acceptor + H2O = a carboxylate + a reduced electron acceptor + H+
an aldehyde + pyrroloquinoline quinone + H2O = a carboxylate + pyrroloquinoline quinol + H+
an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]
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 electron acceptor = an aldehyde + a reduced electron acceptor
a primary alcohol + 2 an oxidized cytochrome cL = an aldehyde + 2 a reduced cytochrome cL
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]


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


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 Fri Dec 19, 2014, BIOCYC13B.