CHEBI:16119 - shikimic acid

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ChEBI Name shikimic acid
ChEBI ID CHEBI:16119
Definition 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). It is an intermediate metabolite in plants and microorganisms.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:45740, CHEBI:9133, CHEBI:26662, CHEBI:26664
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Formula C7H10O5
Net Charge 0
Average Mass 174.15130
Monoisotopic Mass 174.05282
InChI 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
InChIKey JXOHGGNKMLTUBP-HSUXUTPPSA-N
SMILES O[C@@H]1CC(=C[C@@H](O)[C@H]1O)C(O)=O
Metabolite of Species Details
Saccharomyces cerevisiae (NCBI:txid4932) See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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ChEBI Ontology
Outgoing shikimic acid (CHEBI:16119) has role Escherichia coli metabolite (CHEBI:76971)
shikimic acid (CHEBI:16119) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
shikimic acid (CHEBI:16119) has role plant metabolite (CHEBI:76924)
shikimic acid (CHEBI:16119) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
shikimic acid (CHEBI:16119) is a cyclohexenecarboxylic acid (CHEBI:23483)
shikimic acid (CHEBI:16119) is a hydroxy monocarboxylic acid (CHEBI:35868)
shikimic acid (CHEBI:16119) is conjugate acid of shikimate (CHEBI:36208)
Incoming (3R,4S,5R)-4,5-Dihydroxy-3-phosphonooxy-cyclohex-1-enecarboxylic acid anion (CHEBI:241925) has functional parent shikimic acid (CHEBI:16119)
3-dehydroshikimic acid (CHEBI:30918) has functional parent shikimic acid (CHEBI:16119)
3-phosphoshikimic acid (CHEBI:17052) has functional parent shikimic acid (CHEBI:16119)
4-coumaroylshikimic acid (CHEBI:16428) has functional parent shikimic acid (CHEBI:16119)
5-O-(1-carboxyvinyl)-3-phosphoshikimic acid (CHEBI:16257) has functional parent shikimic acid (CHEBI:16119)
5-[(E)-caffeoyl]shikimic acid (CHEBI:2106) has functional parent shikimic acid (CHEBI:16119)
5-amino-5-deoxy-3-dehydroshikimic acid (CHEBI:29514) has functional parent shikimic acid (CHEBI:16119)
shikimate (CHEBI:36208) is conjugate base of shikimic acid (CHEBI:16119)
IUPAC Name
(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
Note: (2004-07-01) The naturally occurring (-)-form. The (±)-racemate has also been synthesized.
Synonyms Sources
3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid KEGG COMPOUND
3α,4α,5β-trihydroxy-1-cyclohexene-1-carboxylic acid ChemIDplus
[3R-(3α,4α,5β)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylic acid NIST Chemistry WebBook
L-shikimic acid ChEBI
Shikimate KEGG COMPOUND
Shikimic acid KEGG COMPOUND
Manual Xrefs Databases
C00001203 KNApSAcK
C00493 KEGG COMPOUND
HMDB0003070 HMDB
Shikimic_acid Wikipedia
SKM PDBeChem
View more database links
Registry Numbers Types Sources
138-59-0 CAS Registry Number ChemIDplus
138-59-0 CAS Registry Number NIST Chemistry WebBook
2210055 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
24190737 PubMed citation Europe PMC
24628944 PubMed citation Europe PMC
24783849 PubMed citation Europe PMC
24836188 PubMed citation Europe PMC
24894540 PubMed citation Europe PMC
24981409 PubMed citation Europe PMC
Last Modified
11 March 2016