Showing Compound Card for Chorismate (CDB005144)

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Record Information
Version1.0
Created at2020-04-17 19:13:46 UTC
Updated at2020-11-18 16:39:26 UTC
CannabisDB IDCDB005144
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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. Chorismate is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight226.18
Monoisotopic Molecular Weight226.0477
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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSChorismate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-8920000000-c9c1de401e53d5259b37Spectrum
Predicted GC-MSChorismate, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-7439400000-61898d5da9dfc83487d0Spectrum
Predicted GC-MSChorismate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSChorismate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-0006-0900000000-b2b9deccbc523c6d0eab2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-0006-0900000000-c777d18079ce5f3f7cce2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-000f-9100000000-ce6e11131e810ac225a42020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 3V, negativesplash10-002r-0910000000-f6fbf6f220b47bb44d072020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 4V, negativesplash10-000i-0900000000-73859439e65b3b81c4192020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 5V, negativesplash10-000i-0900000000-a7d9ad79c08c938f641d2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 7V, negativesplash10-000i-0900000000-3b8ca1c03a2b18dcb3ee2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 10V, negativesplash10-000i-1900000000-7cb1f442b1b4017f231c2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, negativesplash10-000i-5900000000-ab5c560af44c3e1138902020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 17V, negativesplash10-000l-8900000000-188280d32d1c753f7e222020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 20V, negativesplash10-000l-9600000000-d42db1d206b7d8fe25552020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 23V, negativesplash10-000f-9200000000-e80c9b91e42c7ce5f07c2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 25V, negativesplash10-0006-9200000000-88dbca436a340239632c2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 27V, negativesplash10-0006-9100000000-9202017d9ac4e164e0df2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 30V, negativesplash10-0006-9000000000-50c145d43aba50ec736f2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0570-0940000000-573c1187a2d4556bd2c12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0570-0930000000-fb6a26ac0db1fa8e3a5f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004r-0920000000-5085342dabe01fc8bcab2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004r-0910000000-1ba87cb3a1e14ed46c1a2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1490000000-0c0be827ab9167718ec02015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-2920000000-70cd182f84cfcb7bcc5c2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-6900000000-4c4eaa55fb7ee94f57252015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1590000000-38a825366167edaea0802015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-2920000000-e4d23a3d35bdaecc1db42015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06rl-6900000000-c88f4ed01c10938fc50a2015-09-15View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0012199
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General ReferencesNot Available