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MetaCyc Compound: chorismate

Synonyms: chorismic acid

Superclasses: an acid all carboxy acids a carboxylate a dicarboxylate

Chemical Formula: C10H8O6

Molecular Weight: 224.17 Daltons

Monoisotopic Molecular Weight: 226.04773805359997 Daltons

chorismate compound structure

SMILES: C=C(C(=O)[O-])OC1(C(O)C=CC(C([O-])=O)=C1)

InChI: InChI=1S/C10H10O6/c1-5(9(12)13)16-8-4-6(10(14)15)2-3-7(8)11/h2-4,7-8,11H,1H2,(H,12,13)(H,14,15)/p-2/t7-,8-/m1/s1

InChIKey: InChIKey=WTFXTQVDAKGDEY-HTQZYQBOSA-L

Unification Links: CAS:55508-12-8 , ChEBI:29748 , ChemSpider:4573889 , HMDB:HMDB12199 , IAF1260:34395 , KEGG:C00251 , PubChem:5460312

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -95.44927 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

1,4-dihydroxy-6-naphthoate biosynthesis I , 1,4-dihydroxy-6-naphthoate biosynthesis II :
chorismate → 3-[(1-carboxyvinyl)oxy]benzoate + H2O

4-hydroxybenzoate biosynthesis II (microbes) , tetrahydromethanopterin biosynthesis , ubiquinol-8 biosynthesis (eukaryotic) :
chorismate → 4-hydroxybenzoate + pyruvate

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:

chorismate biosynthesis from 3-dehydroquinate :
5-enolpyruvyl-shikimate 3-phosphate → chorismate + phosphate

3,3'-thiodipropanoate degradation :
3-sulfinopropionate + an acyl-CoA → 3-sulfinopropanoyl-CoA + a carboxylate

dimethylsulfoniopropanoate degradation II (cleavage) :
dimethylsulfoniopropanoate + an acyl-CoA → dimethylsulfoniopropioyl-CoA + a carboxylate

NAD/NADP-NADH/NADPH mitochondrial interconversion (yeast) :
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+
an aldehyde + NAD+ + H2O → a carboxylate + NADH + 2 H+

phosphatidylcholine resynthesis via glycerophosphocholine :
a phosphatidylcholine + 2 H2O → sn-glycero-3-phosphocholine + 2 a carboxylate + 2 H+

Not in pathways:
a 1-acyl 2-lyso-phosphatidylcholine[periplasmic space] + H2O[periplasmic space]a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
an L-1-phosphatidyl-inositol + H2O → a 1-acyl-sn-glycero-3-phospho-D-myo-inositol + a carboxylate + H+
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an aldehyde + oxygen + H2O → a carboxylate + hydrogen peroxide + H+
an aldehyde + FMNH2 + oxygen → hν + a carboxylate + FMN + H2O + 2 H+
an acylcholine + H2O → choline + a carboxylate + H+
a β-monogalactosyldiacylglycerol + 2 H2O → 2 a carboxylate + 3-β-D-galactosyl-sn-glycerol + 2 H+
an acyl phosphate + H2O → a carboxylate + phosphate + H+
an S-acylglutathione + H2O → a carboxylate + glutathione
an N-acyl-L-aspartate + H2O → L-aspartate + a carboxylate

Reactions known to both consume and produce the compound:

1,4-dihydroxy-2-naphthoate biosynthesis I , 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) , 2,3-dihydroxybenzoate biosynthesis , salicylate biosynthesis I :
chorismate ↔ isochorismate

2-heptyl-3-hydroxy-4(1H)-quinolone biosynthesis , 4-hydroxy-2(1H)-quinolone biosynthesis , acridone alkaloid biosynthesis , L-tryptophan biosynthesis :
chorismate + L-glutamine ↔ anthranilate + L-glutamate + pyruvate + H+

4-aminobenzoate biosynthesis :
chorismate + L-glutamine ↔ 4-amino-4-deoxychorismate + L-glutamate

bacilysin biosynthesis , L-phenylalanine biosynthesis I , L-phenylalanine biosynthesis II , L-tyrosine biosynthesis I , L-tyrosine biosynthesis II , L-tyrosine biosynthesis III , salinosporamide A biosynthesis :
chorismate ↔ prephenate

phenazine-1-carboxylate biosynthesis :
chorismate + L-glutamine ↔ 2-amino-4-deoxy-chorismate + L-glutamate

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

In Reactions of unknown directionality:

Not in pathways:
chorismate = 3-hydroxybenzoate + pyruvate
chorismate + H2O = (3R,4R)-3,4-dihydroxy-3,4-dihydrobenzoate + pyruvate

Not in pathways:
a monoamide of a dicarboxylate + H2O = a dicarboxylate + ammonium

Not in pathways:
eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a 2-acyl 1-lyso-phosphatidylcholine[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an aldehyde + an electron-transfer quinone + H2O = a carboxylate + an electron-transfer quinol + H+
a triacyl-sn-glycerol + H2O = a 1,2-diacyl-sn-glycerol + a carboxylate + H+
a penicillin + H2O = 6-aminopenicillanate + a carboxylate
an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]
a nitrile + 2 H2O = a carboxylate + ammonium
an aliphatic nitrile + 2 H2O = a carboxylate + ammonium
an N-acyl-L-homoserine lactone + H2O = L-homoserine lactone + a carboxylate
an aldehyde + an oxidized unknown electron acceptor + H2O = a carboxylate + an reduced unknown electron acceptor + H+
an N-acylated aromatic-L-amino acid + H2O = a carboxylate + an aromatic L-amino acid
an N-acylated-D-amino acid + H2O = a D-amino acid + a carboxylate
an N-acylated aliphatic-L-amino acid + H2O = a carboxylate + an aliphatic L-amino acid
a D-hexose + an acyl phosphate = a D-hexose-phosphate + a carboxylate
an aldehyde + 2 an oxidized ferredoxin + H2O = a carboxylate + 2 a reduced ferredoxin + 3 H+
an aldehyde + NAD(P)+ + H2O = a carboxylate + NAD(P)H + 2 H+
an N-acyl-D-glutamate + H2O = a carboxylate + D-glutamate
an anilide + H2O = aniline + a carboxylate + H+
a 5'-acylphosphoadenosine + H2O = a carboxylate + AMP + 2 H+
a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H+
an N6acyl-L-lysine + H2O = a carboxylate + L-lysine
an N-acyl-D-aspartate + H2O = a carboxylate + D-aspartate

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

Inhibitor (Allosteric) of: DAHP synthase [BSUB93, Jensen65, Nester67, Llewellyn80, Huang74, Huang74a] , shikimate kinase [Huang75]

Inhibitor (Mechanism unknown) of: prephenate dehydratase [Duggleby et al., 1978]

This compound has been characterized as an alternative substrate of the following enzymes: 2-amino-4-deoxychorismate hydrolase


References

BSUB93: "Bacillus subtilis and Other Gram-Positive Bacteria: Biochemistry, Physiology, and Molecular Genetics." (1993). Editors: Sonenshein, A.L., Hoch, J.A., Losick, R. American Society For Microbiology, Washington, DC.

Duggleby et al., 1978: Duggleby RG, Sneddon MK, Morrison JF (1978). "Chorismate mutase-prephenate dehydratase from Escherichia coli: active sites of a bifunctional enzyme." Biochemistry 1978;17(8);1548-54. PMID: 348236

Huang74: Huang L, Nakatsukasa M, Nester E (1974). "Regulation of aromatic amino acid biosynthesis in Bacillus subtilis 168. Purification, characterization, and subunit structure of the bifunctional enzyme 3-deoxy-D-arabinoheptulosonate 7-phosphate synthetase-chorismate mutase." J Biol Chem 1974;249(14);4467-72. PMID: 4211044

Huang74a: Huang L, Montoya AL, Nester EW (1974). "Characterization of the functional activities of the subunits of 3-deoxy-D-arabinoheptulosonate 7-phosphate synthetase-chorismate mutase from Bacillus subtilis 168." J Biol Chem 1974;249(14);4473-0. PMID: 4210506

Huang75: Huang L, Montoya AL, Nester EW (1975). "Purification and characterization of shikimate kinase enzyme activity in Bacillus subtilis." J Biol Chem 1975;250(19);7675-81. PMID: 170268

Jensen65: Jensen RA, Nester EW (1965). "The regulatory significance of intermediary metabolites: control of aromatic acid biosynthesis by feedback inhibition in Bacillus subtilis." J Mol Biol 12;468-81. PMID: 14337509

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

Llewellyn80: Llewellyn DJ, Daday A, Smith GD (1980). "Evidence for an artificially evolved bifunctional 3-deoxy-D-arabinoheptulosonate-7-phosphate synthase-chorismate mutase in Bacillus subtilis." J Biol Chem 1980;255(5);2077-84. PMID: 6101597

Nester67: Nester EW, Lorence JH, Nasser DS (1967). "An enzyme aggregate involved in the biosynthesis of aromatic amino acids in Bacillus subtilis. Its possible function in feedback regulation." Biochemistry 1967;6(5);1553-63. PMID: 4962501


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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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