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Escherichia coli K-12 substr. MG1655 Compound: acetyl-CoA

Synonyms: acetyl coenzyme-A, ac-CoA, acetylcoenzyme-A, acetyl-S-CoA, ac-S-CoA

Superclasses: an ester a thioester a coenzyme A-activated compound

Chemical Formula: C23H34N7O17P3S

Molecular Weight: 805.54 Daltons

Monoisotopic Molecular Weight: 809.1257730519 Daltons

SMILES: CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-]

InChI: InChI=1S/C23H38N7O17P3S/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/p-4/t13-,16-,17-,18+,22-/m1/s1

InChIKey: InChIKey=ZSLZBFCDCINBPY-ZSJPKINUSA-J

Unification Links: CAS:72-89-9 , ChEBI:57288 , HMDB:HMDB01206 , IAF1260:33558 , KEGG:C00024 , KNApSAcK:C00007259 , MetaboLights:MTBLC57288 , PubChem:45266541 , UMBBD-Compounds:c0031

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -851.089

Reactions known to consume the compound:

anhydromuropeptides recycling , UDP-N-acetyl-D-glucosamine biosynthesis I :
D-glucosamine 1-phosphate + acetyl-CoAN-acetyl-α-D-glucosamine 1-phosphate + coenzyme A + H+

biotin-carboxyl carrier protein assembly :
ATP + acetyl-CoA + a carboxylated-biotinylated [BCCP dimer] + H2O → malonyl-CoA + a biotinylated [BCCP dimer] + ADP + phosphate + H+

cysteine biosynthesis I :
L-serine + acetyl-CoAO-acetyl-L-serine + coenzyme A

dTDP-N-acetylthomosamine biosynthesis :
dTDP-thomosamine + acetyl-CoA → dTDP-N-acetylthomosamine + coenzyme A + H+

fatty acid biosynthesis initiation I :
acetyl-CoA + a malonyl-[acp] + H+ → an acetoacetyl-[acp] + CO2 + coenzyme A
ATP + acetyl-CoA + hydrogen carbonate → malonyl-CoA + ADP + phosphate + H+

glycolate and glyoxylate degradation II :
acetyl-CoA + glyoxylate + H2O → (S)-malate + coenzyme A + H+

glyoxylate cycle :
oxaloacetate + acetyl-CoA + H2O → citrate + coenzyme A + H+
acetyl-CoA + glyoxylate + H2O → (S)-malate + coenzyme A + H+

leucine biosynthesis :
3-methyl-2-oxobutanoate + acetyl-CoA + H2O → (2S)-2-isopropylmalate + coenzyme A + H+

mixed acid fermentation , TCA cycle I (prokaryotic) :
oxaloacetate + acetyl-CoA + H2O → citrate + coenzyme A + H+

Not in pathways:
a cytidine34 in tRNAmet + ATP + acetyl-CoA + H2O → [elongator tRNAmet]-N4-acetylcytidine34 + ADP + coenzyme A + phosphate + H+
50S ribosomal subunit protein L12 + acetyl-CoA → 50S ribosomal subunit protein L7 + coenzyme A
acetyl-CoA + spermidine → N1-acetylspermidine + coenzyme A + H+
a ribosomal protein-L-alanine + acetyl-CoA → a ribosomal protein-N-acetyl-L-alanine + coenzyme A

Reactions known to produce the compound:

acetate conversion to acetyl-CoA :
acetate + ATP + coenzyme A → acetyl-CoA + AMP + diphosphate

fatty acid β-oxidation I :
a 2,3,4-saturated fatty acyl CoA + acetyl-CoA ↔ a 3-oxoacyl-CoA + coenzyme A

mixed acid fermentation :
formate + acetyl-CoA ← pyruvate + coenzyme A

phenylacetate degradation I (aerobic) :
2,3-didehydroadipyl-CoA + acetyl-CoA ← 3-oxo-5,6-didehydrosuberyl-CoA + coenzyme A
succinyl-CoA + acetyl-CoA ← 3-oxoadipyl-CoA + coenzyme A

pyruvate decarboxylation to acetyl CoA :
acetyl-CoA + a [pyruvate dehydrogenase E2 protein] N6-dihydrolipoyl-L-lysine ← a [pyruvate dehydrogenase E2 protein] N6-S-acetyldihydrolipoyl-L-lysine + coenzyme A

superpathway of glycolysis, pyruvate dehydrogenase, TCA, and glyoxylate bypass :
pyruvate + coenzyme A + NAD+acetyl-CoA + CO2 + NADH

Reactions known to both consume and produce the compound:

2'-deoxy-α-D-ribose 1-phosphate degradation , 2-oxopentenoate degradation , ethanol degradation I , threonine degradation IV :
acetaldehyde + coenzyme A + NAD+acetyl-CoA + NADH + H+

acetate formation from acetyl-CoA I :
acetyl-CoA + phosphate ↔ acetyl phosphate + coenzyme A

acetoacetate degradation (to acetyl CoA) :
2 acetyl-CoA ↔ acetoacetyl-CoA + coenzyme A
acetoacetate + acetyl-CoA ↔ acetoacetyl-CoA + acetate

fatty acid biosynthesis initiation II , superpathway of fatty acid biosynthesis initiation (E. coli) :
a holo-[acyl-carrier protein] + acetyl-CoA ↔ an acetyl-[acp] + coenzyme A

mixed acid fermentation :
acetaldehyde + coenzyme A + NAD+acetyl-CoA + NADH + H+
acetyl-CoA + phosphate ↔ acetyl phosphate + coenzyme A

ornithine biosynthesis :
L-glutamate + acetyl-CoAN-acetyl-L-glutamate + coenzyme A + H+

threonine degradation II :
glycine + acetyl-CoA ↔ 2-amino-3-oxobutanoate + coenzyme A + H+

Not in pathways:
pyruvate + 2 an oxidized ferredoxin + coenzyme A ↔ acetyl-CoA + CO2 + 2 a reduced ferredoxin + H+
a 2,3,4-saturated fatty acyl CoA + acetate ↔ a 2,3,4-saturated fatty acid + acetyl-CoA
pyruvate + an oxidized flavodoxin + coenzyme A + H+acetyl-CoA + CO2 + a reduced flavodoxin
maltose + acetyl-CoA ↔ acetylmaltose + coenzyme A
a β-D-galactoside + acetyl-CoA ↔ a 6-acetyl-β-D-galactoside + coenzyme A

In Reactions of unknown directionality:

Not in pathways:
acetyl-CoA + oxalate = oxalyl-CoA + acetate
3-cis-dodecenoyl-CoA + acetyl-CoA = 3-keto-5-cis-tetradecenoyl-CoA + coenzyme A
an arylamine + acetyl-CoA = an N-acetylarylamine + coenzyme A
acetyl-CoA + dihydrolipoamide = S-acetyldihydrolipoamide + coenzyme A
aminomethylphosphonate + acetyl-CoA = 2-N-acetamidomethylphosphonate + coenzyme A
L-methionine + acetyl-CoA = N-α-acetyl-L-methionine + coenzyme A + H+
an N-hydroxy-arylamine + acetyl-CoA = an N-acetoxyarylamine + coenzyme A
an aliphatic α,ω-diamine + acetyl-CoA = an aliphatic N-acetyl-diamine + coenzyme A + H+

Enzymes activated by acetyl-CoA, sorted by the type of activation, are:

Activator (Allosteric) of: phosphoenolpyruvate carboxylase [Izui81] , citrate synthase

Enzymes inhibited by acetyl-CoA, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: acetoacetyl-CoA transferase , malonyl-CoA-ACP transacylase [Joshi71, Comment 1]

Inhibitor (Uncompetitive) of: formyl-CoA transferase [Toyota08]

Inhibitor (Noncompetitive) of: phosphoglucomutase [Duckworth73, Sanwal72]

Inhibitor (Allosteric) of: malate dehydrogenase, NAD-requiring [Takeo67, Sanwal70a] , malate dehydrogenase [Sanwal68, Bologna07]


References

Bologna07: Bologna FP, Andreo CS, Drincovich MF (2007). "Escherichia coli malic enzymes: two isoforms with substantial differences in kinetic properties, metabolic regulation, and structure." J Bacteriol 189(16);5937-46. PMID: 17557829

Duckworth73: Duckworth HW, Barber BH, Sanwal BD (1973). "The interaction of phosphoglucomutase with nucleotide inhibitors." J Biol Chem 248(4);1431-5. PMID: 4568817

Izui81: Izui K, Taguchi M, Morikawa M, Katsuki H (1981). "Regulation of Escherichia coli phosphoenolpyruvate carboxylase by multiple effectors in vivo. II. Kinetic studies with a reaction system containing physiological concentrations of ligands." J Biochem 90(5);1321-31. PMID: 7040354

Joshi71: Joshi VC, Wakil SJ (1971). "Studies on the mechanism of fatty acid synthesis. XXVI. Purification and properties of malonyl-coenzyme A--acyl carrier protein transacylase of Escherichia coli." Arch Biochem Biophys 1971;143(2);493-505. PMID: 4934182

Sanwal68: Sanwal BD, Wright JA, Smando R (1968). "Allosteric control of the activity of malic enzyme in Escherichia coli." Biochem Biophys Res Commun 31(4);623-7. PMID: 4385340

Sanwal70a: Sanwal BD (1970). "Regulatory characteristics of the diphosphopyridine nucleotide-specific malic enzyme of Escherichia coli." J Biol Chem 1970;245(5);1212-6. PMID: 4313705

Sanwal72: Sanwal BD, Duckworth HW, Hollier ML (1972). "Regulation of phosphoglucomutase." Biochem J 128(1);26P-27P. PMID: 4563765

Takeo67: Takeo K, Murai T, Nagai J, Katsuki H (1967). "Allosteric activation of DPN-linked malic enzyme from Escherichia coli by aspartate." Biochem Biophys Res Commun 1967;29(5);717-22. PMID: 4294855

Toyota08: Toyota CG, Berthold CL, Gruez A, Jonsson S, Lindqvist Y, Cambillau C, Richards NG (2008). "Differential substrate specificity and kinetic behavior of Escherichia coli YfdW and Oxalobacter formigenes formyl coenzyme A transferase." J Bacteriol 190(7):2556-64. PMID: 18245280


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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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