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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:20:53 UTC
Update Date2021-09-14 15:19:55 UTC
HMDB IDHMDB0012199
Secondary Accession Numbers
  • HMDB12199
Metabolite Identification
Common NameChorismate
DescriptionChorismate, also known as chorismic acid, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Chorismate exists in all living species, ranging from bacteria to plants to humans. Chorismate has been detected, but not quantified in, several different foods, such as tamarinds (Tamarindus indica), breadfruits (Artocarpus altilis), raisin bread, sesbania flowers (Sesbania bispinosa), and japanese walnuts (Juglans ailanthifolia). This could make chorismate a potential biomarker for the consumption of these foods. Chorismate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Chorismate.
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, chorismicMeSH, HMDB
(-)-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

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point140 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+154.031661259
DarkChem[M-H]-145.9831661259
DeepCCS[M+H]+149.12430932474
DeepCCS[M-H]-146.72830932474
DeepCCS[M-2H]-179.98630932474
DeepCCS[M+Na]+155.03630932474
AllCCS[M+H]+150.832859911
AllCCS[M+H-H2O]+147.032859911
AllCCS[M+NH4]+154.332859911
AllCCS[M+Na]+155.332859911
AllCCS[M-H]-146.232859911
AllCCS[M+Na-2H]-146.532859911
AllCCS[M+HCOO]-146.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ChorismateO[C@@H]1C=CC(=C[C@H]1OC(=C)C(O)=O)C(O)=O3640.8Standard polar33892256
ChorismateO[C@@H]1C=CC(=C[C@H]1OC(=C)C(O)=O)C(O)=O1804.0Standard non polar33892256
ChorismateO[C@@H]1C=CC(=C[C@H]1OC(=C)C(O)=O)C(O)=O2018.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Chorismate,1TMS,isomer #1C=C(O[C@@H]1C=C(C(=O)O)C=C[C@H]1O[Si](C)(C)C)C(=O)O1984.8Semi standard non polar33892256
Chorismate,1TMS,isomer #2C=C(O[C@@H]1C=C(C(=O)O)C=C[C@H]1O)C(=O)O[Si](C)(C)C1992.8Semi standard non polar33892256
Chorismate,1TMS,isomer #3C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C)C=C[C@H]1O)C(=O)O1977.1Semi standard non polar33892256
Chorismate,2TMS,isomer #1C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C)C=C[C@H]1O[Si](C)(C)C)C(=O)O1988.7Semi standard non polar33892256
Chorismate,2TMS,isomer #2C=C(O[C@@H]1C=C(C(=O)O)C=C[C@H]1O[Si](C)(C)C)C(=O)O[Si](C)(C)C1996.2Semi standard non polar33892256
Chorismate,2TMS,isomer #3C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C)C=C[C@H]1O)C(=O)O[Si](C)(C)C1975.1Semi standard non polar33892256
Chorismate,3TMS,isomer #1C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C)C=C[C@H]1O[Si](C)(C)C)C(=O)O[Si](C)(C)C1989.0Semi standard non polar33892256
Chorismate,1TBDMS,isomer #1C=C(O[C@@H]1C=C(C(=O)O)C=C[C@H]1O[Si](C)(C)C(C)(C)C)C(=O)O2184.3Semi standard non polar33892256
Chorismate,1TBDMS,isomer #2C=C(O[C@@H]1C=C(C(=O)O)C=C[C@H]1O)C(=O)O[Si](C)(C)C(C)(C)C2208.7Semi standard non polar33892256
Chorismate,1TBDMS,isomer #3C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C[C@H]1O)C(=O)O2198.8Semi standard non polar33892256
Chorismate,2TBDMS,isomer #1C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C[C@H]1O[Si](C)(C)C(C)(C)C)C(=O)O2432.9Semi standard non polar33892256
Chorismate,2TBDMS,isomer #2C=C(O[C@@H]1C=C(C(=O)O)C=C[C@H]1O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2424.3Semi standard non polar33892256
Chorismate,2TBDMS,isomer #3C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C[C@H]1O)C(=O)O[Si](C)(C)C(C)(C)C2415.0Semi standard non polar33892256
Chorismate,3TBDMS,isomer #1C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C[C@H]1O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2649.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Chorismate GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-8920000000-c9c1de401e53d5259b372016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chorismate GC-MS (3 TMS) - 70eV, Positivesplash10-004i-7439400000-61898d5da9dfc83487d02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chorismate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chorismate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Chorismate LC-ESI-QTOF 10V, positive-QTOFsplash10-0006-0900000000-b2b9deccbc523c6d0eab2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chorismate LC-ESI-QTOF 20V, positive-QTOFsplash10-0006-0900000000-c777d18079ce5f3f7cce2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chorismate LC-ESI-QTOF 40V, positive-QTOFsplash10-000f-9100000000-ce6e11131e810ac225a42020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chorismate QTOF 3V, negative-QTOFsplash10-002r-0910000000-f6fbf6f220b47bb44d072020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chorismate QTOF 4V, negative-QTOFsplash10-000i-0900000000-73859439e65b3b81c4192020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chorismate QTOF 5V, negative-QTOFsplash10-000i-0900000000-a7d9ad79c08c938f641d2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chorismate QTOF 7V, negative-QTOFsplash10-000i-0900000000-3b8ca1c03a2b18dcb3ee2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chorismate QTOF 10V, negative-QTOFsplash10-000i-1900000000-7cb1f442b1b4017f231c2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chorismate QTOF 15V, negative-QTOFsplash10-000i-5900000000-ab5c560af44c3e1138902020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chorismate QTOF 17V, negative-QTOFsplash10-000l-8900000000-188280d32d1c753f7e222020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chorismate QTOF 20V, negative-QTOFsplash10-000l-9600000000-d42db1d206b7d8fe25552020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chorismate QTOF 23V, negative-QTOFsplash10-000f-9200000000-e80c9b91e42c7ce5f07c2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chorismate QTOF 25V, negative-QTOFsplash10-0006-9200000000-88dbca436a340239632c2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chorismate QTOF 27V, negative-QTOFsplash10-0006-9100000000-9202017d9ac4e164e0df2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chorismate QTOF 30V, negative-QTOFsplash10-0006-9000000000-50c145d43aba50ec736f2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chorismate Orbitrap 1V, negative-QTOFsplash10-0570-0940000000-573c1187a2d4556bd2c12020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chorismate Orbitrap 1V, negative-QTOFsplash10-0570-0930000000-fb6a26ac0db1fa8e3a5f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chorismate Orbitrap 2V, negative-QTOFsplash10-004r-0920000000-5085342dabe01fc8bcab2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chorismate Orbitrap 2V, negative-QTOFsplash10-004r-0910000000-1ba87cb3a1e14ed46c1a2020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chorismate 10V, Positive-QTOFsplash10-0a4i-1490000000-0c0be827ab9167718ec02015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chorismate 20V, Positive-QTOFsplash10-0a4r-2920000000-70cd182f84cfcb7bcc5c2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chorismate 40V, Positive-QTOFsplash10-052r-6900000000-4c4eaa55fb7ee94f57252015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chorismate 10V, Negative-QTOFsplash10-004i-1590000000-38a825366167edaea0802015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chorismate 20V, Negative-QTOFsplash10-0a4r-2920000000-e4d23a3d35bdaecc1db42015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chorismate 40V, Negative-QTOFsplash10-06rl-6900000000-c88f4ed01c10938fc50a2015-09-15Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
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 IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available