Showing Compound Card for Shikimic acid (CDB005162)

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Record Information
Version1.0
Created at2020-04-17 19:15:34 UTC
Updated at2022-12-13 23:36:26 UTC
CannabisDB IDCDB005162
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameShikimic acid
DescriptionShikimic acid, also known as shikimate or acid, shikimic, 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. A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3R,4S,5R stereoisomer). Shikimic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Shikimic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, Shikimic acid has been detected, but not quantified in, several different foods, such as barley, macadamia nuts, nutmegs, winter squash, and borages. This could make shikimic acid a potential biomarker for the consumption of these foods. Shikimic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3,4,5-Trihydroxy-1-cyclohexenecarboxylic acidChEBI
3alpha,4alpha,5beta-Trihydroxy-1-cyclohexene-1-carboxylic acidChEBI
[3R-(3alpha,4alpha,5beta)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acidChEBI
L-Shikimic acidChEBI
ShikimateChEBI
3,4,5-Trihydroxy-1-cyclohexenecarboxylateGenerator
3a,4a,5b-Trihydroxy-1-cyclohexene-1-carboxylateGenerator
3a,4a,5b-Trihydroxy-1-cyclohexene-1-carboxylic acidGenerator
3alpha,4alpha,5beta-Trihydroxy-1-cyclohexene-1-carboxylateGenerator
3Α,4α,5β-trihydroxy-1-cyclohexene-1-carboxylateGenerator
3Α,4α,5β-trihydroxy-1-cyclohexene-1-carboxylic acidGenerator
[3R-(3a,4a,5b)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylateGenerator
[3R-(3a,4a,5b)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acidGenerator
[3R-(3alpha,4alpha,5beta)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylateGenerator
[3R-(3Α,4α,5β)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylateGenerator
[3R-(3Α,4α,5β)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylic acidGenerator
L-ShikimateGenerator
Acid, shikimicMeSH
(-)-ShikimateHMDB
(-)-Shikimic acidHMDB
SkikimateHMDB
Skikimic acidHMDB
(3R,4S,5R)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acidPhytoBank
(-)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acidPhytoBank
Shikimic acidPhytoBank
Chemical FormulaC7H10O5
Average Molecular Weight174.15
Monoisotopic Molecular Weight174.0528
IUPAC Name(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
Traditional Name(-)-shikimate
CAS Registry Number138-59-0
SMILES
O[C@@H]1CC(=C[C@@H](O)[C@H]1O)C(O)=O
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point186 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility150 mg/mL at 21 °CNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.00171 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.00145 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.00145 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.000982 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.00212 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.00171 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0003070
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003991
KNApSAcK IDC00001203
Chemspider ID8412
KEGG Compound IDC00493
BioCyc IDSHIKIMATE
BiGG IDNot Available
Wikipedia LinkShikimic_acid
METLIN ID338
PubChem Compound8742
PDB IDNot Available
ChEBI ID16119
References
General ReferencesNot Available