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MetaCyc Compound: acetate

Synonyms: acetic acid, ethanoic acid

Superclasses: an acid all carboxy acids a carboxylate a monocarboxylate

Component of: sodium acetate

Chemical Formula: C2H3O2

Molecular Weight: 59.044 Daltons

Monoisotopic Molecular Weight: 60.0211293726 Daltons

acetate compound structure

SMILES: CC([O-])=O

InChI: InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4)/p-1

InChIKey: InChIKey=QTBSBXVTEAMEQO-UHFFFAOYSA-M

Unification Links: CAS:64-19-7 , CAS:71-50-1 , ChEBI:30089 , ChemSpider:170 , DrugBank:DB03166 , HMDB:HMDB00042 , IAF1260:33590 , KEGG:C00033 , MetaboLights:MTBLC30089 , PubChem:175

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -57.768696 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

acetate conversion to acetyl-CoA , chitin degradation to ethanol , cis-genanyl-CoA degradation , ethanol degradation II , ethanol degradation IV , oxidative ethanol degradation III :
acetate + ATP + coenzyme A → acetyl-CoA + AMP + diphosphate

citrate lyase activation :
[a holo citrate lyase acyl-carrier protein] + acetate + ATP → an acetyl-[holo citrate lyase acyl-carrier protein] + AMP + diphosphate

malonate degradation II (biotin-dependent) :
[a holo malonate decarboxylase acyl-carrier-protein] + ATP + acetate → an acetyl-[holo malonate decarboxylase acyl-carrier protein] + AMP + diphosphate

methyl ketone biosynthesis :
a carboxylate + ATP + coenzyme A → an acyl-CoA + AMP + diphosphate

Not in pathways:
an acyl-protein synthetase + a carboxylate + ATP → an acyl-protein thioester + AMP + diphosphate
a carboxylate + GTP + coenzyme A → an acyl-CoA + GDP + phosphate

Reactions known to produce the compound:

2,6-dinitrotoluene degradation :
2-hydroxy-5-nitro-6-oxohepta-2,4-dienoate + H2O → 2-hydroxy-5-nitropenta-2,4-dienoate + acetate + H+

2-nitrotoluene degradation , toluene degradation to 2-oxopent-4-enoate (via 4-methylcatechol) , toluene degradation to 2-oxopent-4-enoate (via toluene-cis-diol) , toluene degradation to 2-oxopent-4-enoate I (via o-cresol) :
cis,cis-2-hydroxy-6-oxohepta-2,4-dienoate + H2O → 2-oxopent-4-enoate + acetate + H+

3-(4-sulfophenyl)butyrate degradation :
4-sulfophenyl acetate + H2O → 4-sulfophenol + acetate + H+

4-aminobutyrate degradation V , succinate fermentation to butyrate :
4-hydroxybutanoate + acetyl-CoA → 4-hydroxybutanoyl-CoA + acetate

4-hydroxyacetophenone degradation :
4-hydroxyphenylacetate + H2O → benzene-1,4-diol + acetate

4-hydroxybenzoate biosynthesis IV , vanillin biosynthesis I :
4-coumarate + H2O → 4-hydroxybenzaldehyde + acetate

ajmaline and sarpagine biosynthesis :
17-O-acetylnorajmaline + H2O → norajmaline + acetate + H+
17-O-acetylajmaline + H2O → ajmaline + acetate + H+

anditomin biosynthesis :
acetyl-andilesin A → andilesin B + acetate + H+

anhydromuropeptides recycling , chitin derivatives degradation , N-acetylglucosamine degradation I :
N-acetyl-D-glucosamine 6-phosphate + H2O → D-glucosamine 6-phosphate + acetate

arsonoacetate degradation :
arsonoacetate + an unknown reduced electron acceptor → arsenite + acetate + an unknown oxidized electron acceptor

bacillithiol biosynthesis :
malyl-N-acetyl-D-glucosamine + H2O → malyl-D-glucosamine + acetate

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

β-pyrazole-1-ylalanine biosynthesis :
O-acetyl-L-serine + pyrazole → 3-(pyrazol-1-yl)-L-alanine + acetate + H+

chitin degradation I (archaea) :
N,N'-diacetylchitobiose + H2O → 2-acetamido-4-O-(2-amino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-D-glucose + acetate

chitin degradation to ethanol :
chitin + n H2O → chitosan + n acetate

chitobiose degradation :
N,N'-diacetylchitobiose 6'-phosphate + H2O → N-monoacetylchitobiose 6'-phosphate + acetate

cis-genanyl-CoA degradation :
3-hydroxy-3-(4-methylpent-3-en-1-yl)glutaryl-CoA → 7-methyl-3-oxooct-6-enoyl-CoA + acetate

citrate degradation :
citrate + an acetyl-[holo citrate lyase acyl-carrier protein] + H+ → a citryl-[holo citrate lyase acyl-carrier protein] + acetate

citrate lyase activation :
an acetyl-[holo citrate lyase acyl-carrier protein] + H2O → [a holo citrate lyase acyl-carrier protein] + acetate + H+

cob(II)yrinate a,c-diamide biosynthesis II (late cobalt incorporation) :
precorrin-5 + S-adenosyl-L-methionine + H2O → precorrin-6A + S-adenosyl-L-homocysteine + acetate + 2 H+

creatinine degradation III :
creatinine + an unknown reduced electron acceptor + H2O → methylguanidine + acetate + an unknown oxidized electron acceptor

crotonate fermentation (to acetate and cyclohexane carboxylate) :
crotonate + acetyl-CoA → crotonyl-CoA + acetate

D-cycloserine biosynthesis :
O-acetyl-L-serine + hydroxyurea → O-ureido-L-serine + acetate + H+

D-galactosamine and N-acetyl-D-galactosamine degradation , N-acetyl-D-galactosamine degradation :
N-acetyl-D-galactosamine 6-phosphate + H2O → acetate + D-galactosamine 6-phosphate

Reactions known to both consume and produce the compound:

1,2-propanediol biosynthesis from lactate (engineered) :
acetyl-CoA + (S)-lactate ↔ acetate + (S)-lactoyl-CoA
acetyl-CoA + (R)-lactate ↔ acetate + (R)-lactoyl-CoA

2-methylbutyrate biosynthesis , pyruvate fermentation to propanoate II (acrylate pathway) :
acetyl-CoA + propanoate ↔ acetate + propanoyl-CoA

4-aminobutyrate degradation V , acetyl-CoA fermentation to butyrate II , L-glutamate degradation V (via hydroxyglutarate) :
butanoyl-CoA + acetate ↔ butanoate + acetyl-CoA

acetate formation from acetyl-CoA I , acetylene degradation , Bifidobacterium shunt , L-lysine fermentation to acetate and butyrate , methanogenesis from acetate , mixed acid fermentation , purine nucleobases degradation I (anaerobic) , purine nucleobases degradation II (anaerobic) , pyruvate fermentation to acetate II , pyruvate fermentation to acetate IV , superpathway of fermentation (Chlamydomonas reinhardtii) :
ATP + acetate ↔ ADP + acetyl phosphate

acetate formation from acetyl-CoA II , pyruvate fermentation to acetate III :
acetate + ATP + coenzyme A ↔ acetyl-CoA + ADP + phosphate

acetate formation from acetyl-CoA III (succinate) , anaerobic energy metabolism (invertebrates, mitochondrial) , TCA cycle VII (acetate-producers) :
acetate + succinyl-CoA ↔ acetyl-CoA + succinate

acetoacetate degradation (to acetyl CoA) , pyruvate fermentation to acetone :
acetyl-CoA + acetoacetate ↔ acetate + acetoacetyl-CoA

chitin degradation I (archaea) :
N-acetyl-D-glucosamine + H2O ↔ D-glucosamine + acetate

gallate degradation III (anaerobic) :
3-hydroxy-5-oxohexanoate + acetyl-CoA ↔ 3-hydroxy-5- oxohexanoyl-CoA + acetate
ATP + acetate ↔ ADP + acetyl phosphate
butanoyl-CoA + acetate ↔ butanoate + acetyl-CoA

L-cysteine biosynthesis I :
O-acetyl-L-serine + hydrogen sulfide ↔ L-cysteine + acetate + H+

L-glutamate degradation VI (to pyruvate) :
(S)-citramalate ↔ pyruvate + acetate

L-homocysteine and L-cysteine interconversion :
O-acetyl-L-homoserine + L-cysteine ↔ L-cystathionine + acetate + H+

L-homocysteine biosynthesis :
O-acetyl-L-homoserine + hydrogen sulfide ↔ L-homocysteine + acetate + H+

L-ornithine biosynthesis :
N-acetyl-L-ornithine + H2O ↔ L-ornithine + acetate

succinate fermentation to butyrate :
butanoyl-CoA + acetate ↔ butanoate + acetyl-CoA
acetate + succinyl-CoA ↔ acetyl-CoA + succinate

Not in pathways:
5-acetamidovalerate + 2-oxoglutarate + H2O ↔ L-glutamate + glutarate semialdehyde + acetate
glutaconate + acetyl-CoA ↔ (E)-glutaconyl-CoA + acetate
a 2,3,4-saturated fatty acyl CoA + acetate ↔ a 2,3,4-saturated fatty acid + acetyl-CoA

sphingolipid recycling and degradation (yeast) :
a dihydroceramide + H2O ↔ sphinganine + a carboxylate

In Reactions of unknown directionality:

glycolate degradation II :
6 glycolate + H+ = acetate + 2 succinate + 2 CO2 + 4 H2O

phosphonoacetate degradation :
phosphonoacetate + H2O = acetate + phosphate + H+

Not in pathways:
N-Acetyl-β-alanine + H2O = β-alanine + acetate
N-acetylputrescine + H2O = putrescine + acetate
N8-acetylspermidine + H2O = spermidine + acetate
(S)-citramalate + acetyl-CoA = (3S)-citramalyl-CoA + acetate
malonate + acetyl-CoA = malonyl-CoA + acetate
L-ascorbate + acetyl phosphate = 2-phospho-L-ascorbate + acetate + H+
O-acetyl-L-serine + thiosulfate = S-sulfo-L-cysteine + acetate + H+
3-oxo-2-(cis-2'-pentenyl)-cyclopentane-1-octanoate + 3 oxygen = (+)-7-iso-jasmonate + 3 acetate + 3 H+
4-acetamidobutanoyl-CoA + H2O = 4-aminobutanoyl-coA + acetate
N-acetylphenylethylamine + H2O = acetate + 2-phenylethylamine
5-hydroxypentanoate + acetyl-CoA = 5-hydroxypentanoyl-CoA + acetate
acetol + NADPH + oxygen = acetate + formaldehyde + NADP+ + H2O
poly-β-1,6-N-acetyl-D-glucosamine + H2O = partially N-deacetylated poly-β-1,6-N-acetyl-D-glucosamine + acetate + H+
an N-acetylarylalkylamine + H2O = acetate + an arylalkylamine + H+
N,N'-diacetylchitobiose + H2O = N-monoacetylchitobiose + acetate
N-monoacetylchitobiose + H2O = chitobiose + acetate
chitotriose + H2O = N,N''-diacetylchitotriose + acetate
4-hydroxy-2-nonenal-N-acetyl-L-cysteine + H2O = 4-hydroxy-2-nonenal-[L-Cys] conjugate + acetate
N-acetyl-L-aspartate + H2O = L-aspartate + acetate
an O-acetyl-ADP-ribose + H2O = ADP-D-ribose + acetate
acetyl-CoA + citrate = acetate + (3S)-citryl-CoA
malonate + H+ = acetate + CO2
acetyl-CoA + oxalate = oxalyl-CoA + acetate

In Transport reactions:
acetate[cytosol]acetate[periplasmic space] ,
acetate[periplasmic space]acetate[cytosol] ,
acetate[periplasmic space] + H+[periplasmic space]acetate[cytosol] + H+[cytosol]

In Redox half-reactions:
acetate[in] + CO2[in] + 2 H+[in] + 2 e-[membrane] → pyruvate[in] + H2O[in]

Enzymes activated by acetate, sorted by the type of activation, are:

Activator (Mechanism unknown) of: chondro-6-sulfatase [Yamagata68]

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

Inhibitor (Competitive) of: 3-dehydroquinate dehydratase [Chaudhuri86] , acetylornithine deacetylase [Comment 1] , N-acetylglucosamine-6-phosphate deacetylase [Souza97] , cyanase [Little87, Comment 2] , protocatechuate:oxygen 3,4-oxidoreductase [Bull81]

Inhibitor (Mechanism unknown) of: α-dehydro-β-deoxy-D-glucarate aldolase [Fish66] , thiosulfate sulfurtransferase [Alexander87] , glycine-sarcosine methyltransferase [Waditee03] , sarcosine-dimethylglycine methyltransferase [Waditee03]

This compound has been characterized as an alternative substrate of the following enzymes: propionate-CoA ligase , succinyl-CoA:acetate CoA-transferase , propionyl-CoA:succinate CoA transferase , butyrate kinase , 4-hydroxybutyryl-CoA synthetase , 3-hydroxypropionyl-CoA synthetase , propionate kinase


References

Alexander87: Alexander K, Volini M (1987). "Properties of an Escherichia coli rhodanese." J Biol Chem 262(14);6595-604. PMID: 3553189

Bull81: Bull C, Ballou DP (1981). "Purification and properties of protocatechuate 3,4-dioxygenase from Pseudomonas putida. A new iron to subunit stoichiometry." J Biol Chem 256(24);12673-80. PMID: 6273403

Chaudhuri86: Chaudhuri S, Lambert JM, McColl LA, Coggins JR (1986). "Purification and characterization of 3-dehydroquinase from Escherichia coli." Biochem J 1986;239(3);699-704. PMID: 2950851

Fish66: Fish D, Blumenthal H "2-keto-3-deoxy-D-glucarate aldolase." Meth Enz 1966;9:529-534.

JavidMajd00: Javid-Majd F, Blanchard JS (2000). "Mechanistic analysis of the argE-encoded N-acetylornithine deacetylase." Biochemistry 2000;39(6);1285-93. PMID: 10684608

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

Little87: Little RM, Anderson PM (1987). "Structural properties of cyanase. Denaturation, renaturation, and role of sulfhydryls and oligomeric structure in catalytic activity." J Biol Chem 1987;262(21);10120-6. PMID: 3301828

Souza97: Souza JM, Plumbridge JA, Calcagno ML (1997). "N-acetylglucosamine-6-phosphate deacetylase from Escherichia coli: purification and molecular and kinetic characterization." Arch Biochem Biophys 1997;340(2);338-46. PMID: 9143339

Waditee03: Waditee R, Tanaka Y, Aoki K, Hibino T, Jikuya H, Takano J, Takabe T, Takabe T (2003). "Isolation and functional characterization of N-methyltransferases that catalyze betaine synthesis from glycine in a halotolerant photosynthetic organism Aphanothece halophytica." J Biol Chem 278(7);4932-42. PMID: 12466265

Yamagata68: Yamagata T, Saito H, Habuchi O, Suzuki S (1968). "Purification and properties of bacterial chondroitinases and chondrosulfatases." J Biol Chem 243(7);1523-35. PMID: 5647268


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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
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