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Shikimic acid (FDB003991)

Record Information
Version1.0
Creation date2010-04-08 22:06:02 UTC
Update date2020-09-17 15:40:48 UTC
Primary IDFDB003991
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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.
CAS Number138-59-0
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point186 oC
Boiling PointNot Available
Experimental Water Solubility150 mg/mL at 21 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
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
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 ID8412
ChEMBL IDCHEMBL290345
KEGG Compound IDC00493
Pubchem Compound ID8742
Pubchem Substance IDNot Available
ChEBI ID16119
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03070
CRC / DFC (Dictionary of Food Compounds) IDCTQ51-O:CTQ47-R
EAFUS IDNot Available
Dr. Duke IDSHIKIMIC-ACID
BIGG IDNot Available
KNApSAcK IDC00001203
HET IDSKM
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDShikimic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti convulsant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti radicularDUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
antitumor promoter35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
bruchifuge25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
carcinogenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
ileorelaxantDUKE
mutagenicDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).