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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:30 UTC
Update Date2021-09-14 15:19:50 UTC
HMDB IDHMDB0003070
Secondary Accession Numbers
  • HMDB03070
Metabolite Identification
Common NameShikimic acid
DescriptionShikimic acid, more commonly known as its anionic form shikimate, is a cyclohexene, a cyclitol and a cyclohexanecarboxylic acid. It is an important biochemical intermediate in plants and microorganisms. Its name comes from the Japanese flower shikimi (the Japanese star anise, Illicium anisatum), from which it was first isolated. Shikimic acid is a precursor for: the aromatic amino acids phenylalanine and tyrosine; indole, indole derivatives and tryptophan; many alkaloids and other aromatic metabolites; tannins; and lignin. In pharmaceutical industry, shikimic acid from chinese star anise is used as a base material for production of Tamiflu (oseltamivir). Although shikimic acid is present in most autotrophic organisms, it is a biosynthetic intermediate and generally found in very low concentrations.
Structure
Data?1601265222
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
(-)-ShikimateHMDB
(-)-Shikimic acidHMDB
SkikimateHMDB
Skikimic acidHMDB
Acid, shikimicHMDB
(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 Weight174.1513
Monoisotopic Molecular Weight174.05282343
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
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
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0udj-0970000000-42465cd3f3e138b0bc122014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0udi-0790000000-1100443abb8605953f582014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-9450000000-e6ca954dc1a9c1cc42852014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0udi-0491000000-49993b9b18e12b9461fc2014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-0391000000-ddb2c574233062a911fa2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udj-0970000000-42465cd3f3e138b0bc122017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0790000000-1100443abb8605953f582017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9450000000-e6ca954dc1a9c1cc42852017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-0491000000-49993b9b18e12b9461fc2017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4900000000-817f1ed3feb4c763285f2016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0092-7119400000-67b0989b5019a72e10162017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-052f-5900000000-81513c2837c16e09b7702021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0900000000-e6ca4ce5acb44dc23a742012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004r-9700000000-18afe769b0ef5ba3fbdb2012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9100000000-7d0218e803b828de53b22012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-01b9-1900000000-fd80f5e7f51d927e8e152012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-9300000000-cf8a3148fd132540bf972012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-ed28bc20ae43473043c92012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9000000000-65249fc24f2de4acf2c72012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-26dfc876ae35c2cdb8452012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-006x-9600000000-3a5ab91754d9d837d8b42012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-01b9-1900000000-6cba5b9b7c48915220452017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9300000000-12d15a049b141a37f34e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-ed28bc20ae43473043c92017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-9864f7359ffed65d6ef02017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-26dfc876ae35c2cdb8452017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-006x-9600000000-3a5ab91754d9d837d8b42017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-2a02691107b26b47bfe72016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-d0e0c1c61a8cc849c4bc2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03kc-9500000000-1be2290fb516bd446a612016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-563539f2a2fed5cb4f8a2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-2900000000-229ad430d980f20f597b2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00b9-9300000000-db4467dbe0ef7549a6e72016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0c00-0900000000-09d3707be04338c7ef832021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0c00-2900000000-8da8948fa49b33f203452021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08i0-8900000000-eb22c27860c45243cdce2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-4cd4c9e7bcabe7ee1ba22021-09-07View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-05View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)2016-10-22View Spectrum
2D NMR[1H, 1H] 2D NMR Spectrum (predicted)2012-12-04View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.027 +/- 0.006 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.056 +/- 0.015 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.039 +/- 0.015 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.051 +/- 0.014 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.042 +/- 0.01 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.057 +/- 0.027 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.03 +/- 0.006 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.13 +/- 0.098 uMAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.004 +/- 0.001 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothProstate Cancer details
Associated Disorders and Diseases
Disease References
Prostate cancer
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031172
KNApSAcK IDC00001203
Chemspider ID8412
KEGG Compound IDC00493
BioCyc IDSHIKIMATE
BiGG IDNot Available
Wikipedia LinkShikimic_acid
METLIN ID338
PubChem Compound8742
PDB IDNot Available
ChEBI ID16119
Food Biomarker OntologyNot Available
VMH IDSKM
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Rose GA: Studies on the chemical nature of urinary chemiluminescence. Br J Urol. 1976 Feb;48(1):61-71. [PubMed:5168 ]
  2. Liu Y, Xie MX, Jiang M, Wang YD: Spectroscopic investigation of the interaction between human serum albumin and three organic acids. Spectrochim Acta A Mol Biomol Spectrosc. 2005 Jul;61(9):2245-51. [PubMed:15911418 ]