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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: 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

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:

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

dimethylsulfoniopropionate 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:
an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
an L-1-phosphatidyl-inositol + H2O → 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+
a 1-lysophosphatidylcholine[periplasmic space] + H2O[periplasmic space]a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an aldehyde + FMNH2 + oxygen → hν + a carboxylate + FMN + H2O + 2 H+
an acylcholine + H2O → choline + a carboxylate + H+
a 1,2-diacyl-3-β-D-galactosyl-sn-glycerol + 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 , tryptophan biosynthesis :
chorismate + L-glutamine ↔ anthranilate + L-glutamate + pyruvate + H+

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

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

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

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

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


a monoamide of a dicarboxylate + H2O = ammonium + a dicarboxylate


eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a penicillin + H2O = 6-aminopenicillanate + a carboxylate
an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]
an aldehyde + pyrroloquinoline quinone + H2O = a carboxylate + pyrroloquinoline quinol + H+
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 electron acceptor + H2O = a carboxylate + a reduced 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 [Editors93, JENSEN65, Nester67, Llewellyn80, Huang74, Huang74a] , shikimate kinase [Huang75]

Inhibitor (Mechanism unknown) of: prephenate dehydratase [Duggleby78]


References

Duggleby78: 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

Editors93: Editors: Abraham L. Sonenshein, James A. Hoch, Richard Losick (1993). "Bacillus subtilis and Other Gram-Positive Bacteria: Biochemistry, Physiology, and Molecular Genetics." American Society For Microbiology, Washington, DC 20005.

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
Page generated by SRI International Pathway Tools version 18.5 on Thu Nov 27, 2014, biocyc14.