You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB00148
NameChorismate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionChorismate, also known as chorismic acid or acid, chorismic, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Chorismate is an extremely weak basic (essentially neutral) compound (based on its pKa). Chorismate exists in all living species, ranging from bacteria to humans. chorismate can be converted into prephenate; which is catalyzed by the enzyme chorismate mutase. In yeast, chorismate is involved in the metabolic pathway called the tyrosine metabolism pathway.
Structure
Thumb
Synonyms
  • Chorismic acid
  • (3R,4R)-3-[(1-Carboxyvinyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid
  • (3R-trans)-3-((1-Carboxyethenyl)oxy)-4-hydroxy-1,5-cyclohexadiene-1-carboxylic acid
  • (3R,4R)-3-[(1-Carboxyethenyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylate
  • (3R,4R)-3-[(1-Carboxyvinyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylate
  • (3R-trans)-3-((1-Carboxyethenyl)oxy)-4-hydroxy-1,5-cyclohexadiene-1-carboxylate
  • (3R,4R)-3-[(1-Carboxyethenyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid
  • Acid, chorismic
CAS number55508-12-8
WeightAverage: 226.1828
Monoisotopic: 226.047738052
InChI KeyWTFXTQVDAKGDEY-HTQZYQBOSA-N
InChIInChI=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)/t7-,8-/m1/s1
IUPAC Name(3R,4R)-3-[(1-carboxyeth-1-en-1-yl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid
Traditional IUPAC Namechorismic acid
Chemical FormulaC10H10O6
SMILES[H]OC(=O)C(O[C@]1([H])C([H])=C(C([H])=C([H])[C@@]1([H])O[H])C(=O)O[H])=C([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
Substituents
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
  • 5-[(1-carboxyethenyl)oxy]-6-hydroxycyclohexa-1,3-diene-1-carboxylic acid (CHEBI:17333 )
Physical Properties
StateSolid
Charge0
Melting point140 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility8.8 g/LALOGPS
logP0.52ALOGPS
logP-0.13ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)3.39ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.31 m³·mol⁻¹ChemAxon
Polarizability20.49 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
  • Nucleus
Organoleptic PropertiesNot Available
SMPDB Pathways
Phenylalanine metabolismPW002437 ThumbThumb?image type=greyscaleThumb?image type=simple
Tryptophan metabolismPW002442 ThumbThumb?image type=greyscaleThumb?image type=simple
Tyrosine metabolismPW002441 ThumbThumb?image type=greyscaleThumb?image type=simple
tetrahydrofolate biosynthesisPW002417 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Folate biosynthesisec00790 Map00790
Phenylalanine metabolismec00360 Map00360
Phenylalanine, tyrosine and tryptophan biosynthesisec00400 Map00400
Tryptophan metabolismec00380 Map00380
Tyrosine metabolismec00350 Map00350
SMPDB Reactions
Chorismate + L-GlutamineL-Glutamic acid + 4-amino-4-deoxychorismate
ChorismatePrephenate
Chorismate + L-GlutaminePyruvic acid + L-Glutamic acid + hydron + 2-Aminobenzoic acid
KEGG Reactions
Chorismate + L-Glutamine4-amino-4-deoxychorismic acid + L-Glutamic acid
Chorismate + L-Glutamine2-Aminobenzoic acid + Pyruvic acid + L-Glutamic acid + hydron
ChorismatePrephenate
ChorismatePyruvic acid + 4-Hydroxybenzoic acid
5-O-(1-carboxyvinyl)-3-phosphoshikimic acidChorismate + phosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Miozzari, G., Niederberger, P., Hutter, R. (1978). "Tryptophan biosynthesis in Saccharomyces cerevisiae: control of the flux through the pathway." J Bacteriol 134:48-59.348687
  • Braus, G. H. (1991). "Aromatic amino acid biosynthesis in the yeast Saccharomyces cerevisiae: a model system for the regulation of a eukaryotic biosynthetic pathway." Microbiol Rev 55:349-370.1943992
  • Henstrand, J. M., Schaller, A., Braun, M., Amrhein, N., Schmid, J. (1996). "Saccharomyces cerevisiae chorismate synthase has a flavin reductase activity." Mol Microbiol 22:859-866.8971708
  • Crombie, T., Boyle, J. P., Coggins, J. R., Brown, A. J. (1994). "The folding of the bifunctional TRP3 protein in yeast is influenced by a translational pause which lies in a region of structural divergence with Escherichia coli indoleglycerol-phosphate synthase." Eur J Biochem 226:657-664.8001582
  • Ball, S. G., Wickner, R. B., Cottarel, G., Schaus, M., Tirtiaux, C. (1986). "Molecular cloning and characterization of ARO7-OSM2, a single yeast gene necessary for chorismate mutase activity and growth in hypertonic medium." Mol Gen Genet 205:326-330.3027508
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17333
HMDB IDHMDB12199
Pubchem Compound ID12039
Kegg IDC00251
ChemSpider ID11542
FOODB IDFDB028846
WikipediaChorismic_acid
BioCyc IDCPD-9517

Enzymes

General function:
Involved in catalytic activity
Specific function:
Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate
Gene Name:
TRP3
Uniprot ID:
P00937
Molecular weight:
53488.89844
Reactions
Chorismate + L-glutamine → anthranilate + pyruvate + L-glutamate.
1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate → 1-C-(3-indolyl)-glycerol 3-phosphate + CO(2) + H(2)O.
General function:
Involved in biosynthetic process
Specific function:
Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate
Gene Name:
TRP2
Uniprot ID:
P00899
Molecular weight:
56767.0
Reactions
Chorismate + L-glutamine → anthranilate + pyruvate + L-glutamate.
General function:
Involved in biosynthetic process
Specific function:
Catalyzes the biosynthesis of 4-amino-4-deoxychorismate (ADC) from chorismate and glutamine. Required for the synthesis of 4-aminobenzoate (PABA), an important component in tetrahydrofolate biosynthesis
Gene Name:
ABZ1
Uniprot ID:
P37254
Molecular weight:
88543.5
Reactions
Chorismate + L-glutamine → 4-amino-4-deoxychorismate + L-glutamate.
General function:
Involved in chorismate synthase activity
Specific function:
5-O-(1-carboxyvinyl)-3-phosphoshikimate = chorismate + phosphate
Gene Name:
ARO2
Uniprot ID:
P28777
Molecular weight:
40838.0
Reactions
5-O-(1-carboxyvinyl)-3-phosphoshikimate → chorismate + phosphate.
General function:
Involved in chorismate mutase activity
Specific function:
Chorismate = prephenate
Gene Name:
ARO7
Uniprot ID:
P32178
Molecular weight:
29746.80078
Reactions
Chorismate → prephenate.