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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:20:53 UTC
Update Date2020-05-13 02:11:20 UTC
HMDB IDHMDB0012199
Secondary Accession Numbers
  • HMDB12199
Metabolite Identification
Common NameChorismate
DescriptionChorismic acid, more commonly known as its anionic form chorismate, is an important biochemical intermediate in plants and microorganisms. It is a precursor for the aromatic amino acids phenylalanine and tyrosine,indole, indole derivatives and tryptophan,2,3-dihydroxybenzoic acid (DHB) used for enterobactin biosynthesis,the plant hormone salicylic acid and many alkaloids and other aromatic metabolites. -- Wikipedia .
Structure
Data?1589335880
Synonyms
ValueSource
(3R,4R)-3-[(1-Carboxyvinyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acidChEBI
(3R-trans)-3-((1-Carboxyethenyl)oxy)-4-hydroxy-1,5-cyclohexadiene-1-carboxylic acidChEBI
Chorismic acidKegg
(3R,4R)-3-[(1-Carboxyethenyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylateKegg
(3R,4R)-3-[(1-Carboxyvinyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylateGenerator
(3R-trans)-3-((1-Carboxyethenyl)oxy)-4-hydroxy-1,5-cyclohexadiene-1-carboxylateGenerator
(3R,4R)-3-[(1-Carboxyethenyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acidGenerator
Acid, chorismicHMDB
(-)-Chorismic acidHMDB
(3R,4R)-3-[(1-Carboxyethenyl)oxy]-4-hydroxy-1,5-cyclohexadiene-1-carboxylic acidHMDB
(3R-trans)-3-(1-Carboxyvinyloxy)-4-hydroxy-1,5-cyclohexadiene-1-carboxylic acidHMDB
Chemical FormulaC10H10O6
Average Molecular Weight226.1828
Monoisotopic Molecular Weight226.047738052
IUPAC Name(3R,4R)-3-[(1-carboxyeth-1-en-1-yl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid
Traditional Namechorismic acid
CAS Registry Number617-12-9
SMILES
O[C@@H]1C=CC(=C[C@H]1OC(=C)C(O)=O)C(O)=O
InChI Identifier
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)/t7-,8-/m1/s1
InChI KeyWTFXTQVDAKGDEY-HTQZYQBOSA-N
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 )
Ontology
Disposition

Route of exposure:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point140 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-8920000000-c9c1de401e53d5259b37Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-004i-7439400000-61898d5da9dfc83487d0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-0006-0900000000-b2b9deccbc523c6d0eabSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-0006-0900000000-c777d18079ce5f3f7cceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-000f-9100000000-ce6e11131e810ac225a4Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 3V, negativesplash10-002r-0910000000-f6fbf6f220b47bb44d07Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 4V, negativesplash10-000i-0900000000-73859439e65b3b81c419Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 5V, negativesplash10-000i-0900000000-a7d9ad79c08c938f641dSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 7V, negativesplash10-000i-0900000000-3b8ca1c03a2b18dcb3eeSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 10V, negativesplash10-000i-1900000000-7cb1f442b1b4017f231cSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, negativesplash10-000i-5900000000-ab5c560af44c3e113890Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 17V, negativesplash10-000l-8900000000-188280d32d1c753f7e22Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 20V, negativesplash10-000l-9600000000-d42db1d206b7d8fe2555Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 23V, negativesplash10-000f-9200000000-e80c9b91e42c7ce5f07cSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 25V, negativesplash10-0006-9200000000-88dbca436a340239632cSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 27V, negativesplash10-0006-9100000000-9202017d9ac4e164e0dfSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, negativesplash10-0006-9000000000-50c145d43aba50ec736fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0570-0940000000-573c1187a2d4556bd2c1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0570-0930000000-fb6a26ac0db1fa8e3a5fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004r-0920000000-5085342dabe01fc8bcabSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004r-0910000000-1ba87cb3a1e14ed46c1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1490000000-0c0be827ab9167718ec0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-2920000000-70cd182f84cfcb7bcc5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-6900000000-4c4eaa55fb7ee94f5725Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1590000000-38a825366167edaea080Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-2920000000-e4d23a3d35bdaecc1db4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06rl-6900000000-c88f4ed01c10938fc50aSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028846
KNApSAcK IDC00000733
Chemspider ID11542
KEGG Compound IDC00251
BioCyc IDCHORISMATE
BiGG IDNot Available
Wikipedia LinkChorismic_acid
METLIN IDNot Available
PubChem Compound12039
PDB IDISJ
ChEBI ID17333
Food Biomarker OntologyNot Available
VMH IDCHOR
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available