Record Information
Version1.0
Creation date2011-09-21 01:46:02 UTC
Update date2020-09-17 15:40:40 UTC
Primary IDFDB028846
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameChorismate
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. The (3R,4R)-stereoisomer of 5--6-hydroxycyclohexa-1,3-diene-1-carboxylic acid. Chorismate is an extremely weak basic (essentially neutral) compound (based on its pKa). Chorismate exists in all living species, ranging from bacteria to humans. Outside of the human body, Chorismate has been detected, but not quantified in, several different foods, such as grass pea, beans, globe artichokes, pummelo, and citrus. This could make chorismate a potential biomarker for the consumption of these foods.
CAS Number55508-12-8
Structure
Thumb
Synonyms
SynonymSource
(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
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H10O6
IUPAC name(3R,4R)-3-[(1-carboxyeth-1-en-1-yl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid
InChI IdentifierInChI=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
Isomeric SMILESO[C@@H]1C=CC(=C[C@H]1OC(=C)C(O)=O)C(O)=O
Average Molecular Weight226.1828
Monoisotopic Molecular Weight226.047738052
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-8920000000-c9c1de401e53d5259b37JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-004i-7439400000-61898d5da9dfc83487d0JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-0006-0900000000-b2b9deccbc523c6d0eabJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-0006-0900000000-c777d18079ce5f3f7cceJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-000f-9100000000-ce6e11131e810ac225a4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 3V, negativesplash10-002r-0910000000-f6fbf6f220b47bb44d07JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 4V, negativesplash10-000i-0900000000-73859439e65b3b81c419JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 5V, negativesplash10-000i-0900000000-a7d9ad79c08c938f641dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 7V, negativesplash10-000i-0900000000-3b8ca1c03a2b18dcb3eeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 10V, negativesplash10-000i-1900000000-7cb1f442b1b4017f231cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, negativesplash10-000i-5900000000-ab5c560af44c3e113890JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 17V, negativesplash10-000l-8900000000-188280d32d1c753f7e22JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 20V, negativesplash10-000l-9600000000-d42db1d206b7d8fe2555JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 23V, negativesplash10-000f-9200000000-e80c9b91e42c7ce5f07cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 25V, negativesplash10-0006-9200000000-88dbca436a340239632cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 27V, negativesplash10-0006-9100000000-9202017d9ac4e164e0dfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, negativesplash10-0006-9000000000-50c145d43aba50ec736fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0570-0940000000-573c1187a2d4556bd2c1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0570-0930000000-fb6a26ac0db1fa8e3a5fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004r-0920000000-5085342dabe01fc8bcabJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004r-0910000000-1ba87cb3a1e14ed46c1aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1490000000-0c0be827ab9167718ec0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-2920000000-70cd182f84cfcb7bcc5cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-6900000000-4c4eaa55fb7ee94f5725JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1590000000-38a825366167edaea080JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-2920000000-e4d23a3d35bdaecc1db4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06rl-6900000000-c88f4ed01c10938fc50aJSpectraViewer
ChemSpider ID11542
ChEMBL IDNot Available
KEGG Compound IDC00251
Pubchem Compound ID12039
Pubchem Substance IDNot Available
ChEBI ID17333
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12199
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDISJ
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference