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Shikimic acid (YMDB00216)

Identification
YMDB IDYMDB00216
NameShikimic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionShikimic acid is an intermediate in the chorismate biosynthesis pathway also called shikimate pathway. This pathway occurs in plants and microorganisms. Chorismate is an important intermediate that leads to the biosynthesis of several essential metabolites, including the aromatic amino acids L-phenylalanine, L-tyrosine and L-tryptophan, vitamins E and K, ubiquinone and certain siderophore. [Biocyc ARO-PWY]
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • (-)-Shikimate
  • (-)-Shikimic acid
  • (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid
  • 1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-
  • 3,4, 5-Trihydroxy-1-cyclohexene-1-carboxylic acid
  • 3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid
  • 3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid
  • L-Shikimate
  • L-Shikimic acid
  • Shikimate
  • Shikimic acid
  • SKM
  • 3alpha,4alpha,5beta-Trihydroxy-1-cyclohexene-1-carboxylic acid
  • [3R-(3alpha,4alpha,5beta)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid
  • 3,4,5-Trihydroxy-1-cyclohexenecarboxylate
  • 3a,4a,5b-Trihydroxy-1-cyclohexene-1-carboxylate
  • 3a,4a,5b-Trihydroxy-1-cyclohexene-1-carboxylic acid
  • 3alpha,4alpha,5beta-Trihydroxy-1-cyclohexene-1-carboxylate
  • 3Α,4α,5β-trihydroxy-1-cyclohexene-1-carboxylate
  • 3Α,4α,5β-trihydroxy-1-cyclohexene-1-carboxylic acid
  • [3R-(3a,4a,5b)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylate
  • [3R-(3a,4a,5b)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid
  • [3R-(3alpha,4alpha,5beta)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylate
  • [3R-(3Α,4α,5β)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate
  • [3R-(3Α,4α,5β)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylic acid
  • Acid, shikimic
  • Skikimate
  • Skikimic acid
  • (3R,4S,5R)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid
  • (-)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid
CAS number138-59-0
WeightAverage: 174.1513
Monoisotopic: 174.05282343
InChI KeyJXOHGGNKMLTUBP-HSUXUTPPSA-N
InChIInChI=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
IUPAC Name(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
Traditional IUPAC Name(-)-shikimate
Chemical FormulaC7H10O5
SMILES[H]OC(=O)C1=C([H])[C@@]([H])(O[H])[C@@]([H])(O[H])[C@]([H])(O[H])C1([H])[H]
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
Physical Properties
StateSolid
Charge0
Melting point186 °C
Experimental Properties
PropertyValueReference
Water Solubility150 mg/mL at 21 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogPNot AvailablePhysProp
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Phenylalanine, tyrosine and tryptophan biosynthesisec00400 Map00400
SMPDB ReactionsNot Available
KEGG Reactions
NADPH + hydron + 3-Dehydroshikimic acid → NADP + Shikimic acid
Adenosine triphosphate + Shikimic acid → 3-Phosphoshikimic acid + hydron + ADP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0udj-0970000000-42465cd3f3e138b0bc12JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0udi-0790000000-1100443abb8605953f58JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-9450000000-e6ca954dc1a9c1cc4285JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0udi-0491000000-49993b9b18e12b9461fcJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-0391000000-ddb2c574233062a911faJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udj-0970000000-42465cd3f3e138b0bc12JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0790000000-1100443abb8605953f58JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9450000000-e6ca954dc1a9c1cc4285JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-0491000000-49993b9b18e12b9461fcJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4900000000-817f1ed3feb4c763285fJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0092-7119400000-67b0989b5019a72e1016JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-01b9-1900000000-fd80f5e7f51d927e8e15JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-9300000000-cf8a3148fd132540bf97JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-ed28bc20ae43473043c9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9000000000-65249fc24f2de4acf2c7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-26dfc876ae35c2cdb845JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-006x-9600000000-3a5ab91754d9d837d8b4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-01b9-1900000000-6cba5b9b7c4891522045JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9300000000-12d15a049b141a37f34eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-ed28bc20ae43473043c9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-9864f7359ffed65d6ef0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-26dfc876ae35c2cdb845JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-006x-9600000000-3a5ab91754d9d837d8b4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-7900000000-d77a830354efe8731a42JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-01vx-9700000000-d2060c544171987e3dcdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-01vx-9500000000-baa64c3938f3d039c6e4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-d5821372fd8a830dc962JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00dl-9000000000-cb13aba83ba37150b931JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-01vo-9600000000-3433190ea61f16d92efdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-022l-9600000000-60e85b9b59edb135e4c4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-58e1775d1e013c416201JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-1f370d2806fd8245ebfbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-01vx-9600000000-d502f575cada8c0b5aeaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00dl-9400000000-d0ff38d5a290b8e8248dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0900000000-e6ca4ce5acb44dc23a74JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004r-9700000000-18afe769b0ef5ba3fbdbJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Larimer, F. W., Morse, C. C., Beck, A. K., Cole, K. W., Gaertner, F. H. (1983). "Isolation of the ARO1 cluster gene of Saccharomyces cerevisiae." Mol Cell Biol 3:1609-1614.6355828
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16119
HMDB IDHMDB03070
Pubchem Compound ID8742
Kegg IDC00493
ChemSpider ID8412
FOODB IDFDB003991
WikipediaShikimic_acid
BioCyc ID3-DEHYDRO-SHIKIMATE

Enzymes

Protein Details
1. Pentafunctional AROM polypeptide
General function:
Involved in 3-dehydroquinate dehydratase activity
Specific function:
The AROM polypeptide catalyzes 5 consecutive enzymatic reactions in prechorismate polyaromatic amino acid biosynthesis
Gene Name:
ARO1
Uniprot ID:
P08566
Molecular weight:
174754.0
Reactions
3-deoxy-D-arabino-hept-2-ulosonate 7-phosphate → 3-dehydroquinate + phosphate.
3-dehydroquinate → 3-dehydroshikimate + H(2)O.
Shikimate + NADP(+) → 3-dehydroshikimate + NADPH.
ATP + shikimate → ADP + shikimate 3-phosphate.
Phosphoenolpyruvate + 3-phosphoshikimate → phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate.