Record Information
Version1.0
Creation date2015-05-07 21:13:00 UTC
Update date2019-11-26 03:22:10 UTC
Primary IDFDB031172
Secondary Accession Numbers
  • FDB003991
Chemical Information
FooDB Nameshikimate
DescriptionShikimic acid, also known as shikimate or 3,4,5-trihydroxy-1-cyclohexenecarboxylic acid, is a member of the class of compounds known as shikimic acids and derivatves. Shikimic acids and derivatves are cyclitols containing a cyclohexanecarboxylic acid substituted with three hydroxyl groups at positions 3, 4, and 5. Shikimic acid is soluble (in water) and a weakly acidic compound (based on its pKa). Shikimic acid can be found in a number of food items such as date, rocket salad, redcurrant, and poppy, which makes shikimic acid a potential biomarker for the consumption of these food products. Shikimic acid can be found primarily in blood and urine. Shikimic acid exists in all living species, ranging from bacteria to humans. Shikimic acid, more commonly known as its anionic form shikimate, is a cyclohexene, a cyclitol and a cyclohexanecarboxylic acid. It is an important biochemical metabolite in plants and microorganisms. Its name comes from the Japanese flower shikimi (シキミ, the Japanese star anise, Illicium anisatum), from which it was first isolated in 1885 by Johan Fredrik Eykman. The elucidation of its structure was made nearly 50 years later .
CAS Number138-59-0
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility206 g/LALOGPS
logP-1.7ALOGPS
logP-1.6ChemAxon
logS0.07ALOGPS
pKa (Strongest Acidic)4.1ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.96 m³·mol⁻¹ChemAxon
Polarizability15.75 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H10O5
IUPAC name(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
InChI IdentifierInChI=1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1
InChI KeyJXOHGGNKMLTUBP-HSUXUTPPSA-N
Isomeric SMILESO[C@@H]1CC(=C[C@@H](O)[C@H]1O)C(O)=O
Average Molecular Weight174.1513
Monoisotopic Molecular Weight174.05282343
Classification
Description Belongs to the class of organic compounds known as shikimic acids and derivatves. These are cyclitols containing a cyclohexanecarboxylic acid substituted with three hydroxyl groups at positions 3, 4, and 5.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentShikimic acids and derivatves
Alternative Parents
Substituents
  • Shikimic acid or derivatives
  • Secondary alcohol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSShikimic acid, 4 TMS, GC-MS Spectrumsplash10-0udj-0970000000-42465cd3f3e138b0bc12Spectrum
GC-MSShikimic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-0790000000-1100443abb8605953f58Spectrum
GC-MSShikimic acid, 4 TMS, GC-MS Spectrumsplash10-00di-9450000000-e6ca954dc1a9c1cc4285Spectrum
GC-MSShikimic acid, 4 TMS, GC-MS Spectrumsplash10-0udi-0491000000-49993b9b18e12b9461fcSpectrum
GC-MSShikimic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-0391000000-ddb2c574233062a911faSpectrum
GC-MSShikimic acid, non-derivatized, GC-MS Spectrumsplash10-0udj-0970000000-42465cd3f3e138b0bc12Spectrum
GC-MSShikimic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-0790000000-1100443abb8605953f58Spectrum
GC-MSShikimic acid, non-derivatized, GC-MS Spectrumsplash10-00di-9450000000-e6ca954dc1a9c1cc4285Spectrum
GC-MSShikimic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-0491000000-49993b9b18e12b9461fcSpectrum
Predicted GC-MSShikimic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-4900000000-817f1ed3feb4c763285fSpectrum
Predicted GC-MSShikimic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0092-7119400000-67b0989b5019a72e1016Spectrum
Predicted GC-MSShikimic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-01b9-1900000000-fd80f5e7f51d927e8e152012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-9300000000-cf8a3148fd132540bf972012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-ed28bc20ae43473043c92012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9000000000-65249fc24f2de4acf2c72012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-26dfc876ae35c2cdb8452012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-006x-9600000000-3a5ab91754d9d837d8b42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-01b9-1900000000-6cba5b9b7c48915220452017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9300000000-12d15a049b141a37f34e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-ed28bc20ae43473043c92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-9864f7359ffed65d6ef02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-26dfc876ae35c2cdb8452017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-006x-9600000000-3a5ab91754d9d837d8b42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-7900000000-d77a830354efe8731a422021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-01vx-9700000000-d2060c544171987e3dcd2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-01vx-9500000000-baa64c3938f3d039c6e42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-d5821372fd8a830dc9622021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00dl-9000000000-cb13aba83ba37150b9312021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-01vo-9600000000-3433190ea61f16d92efd2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-022l-9600000000-60e85b9b59edb135e4c42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-58e1775d1e013c4162012021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-1f370d2806fd8245ebfb2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-01vx-9600000000-d502f575cada8c0b5aea2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00dl-9400000000-d0ff38d5a290b8e8248d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0900000000-e6ca4ce5acb44dc23a742012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004r-9700000000-18afe769b0ef5ba3fbdb2012-07-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
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
Processing...
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