shikimic acid (CHEBI:16119)

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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

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.

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

Last Modified

11 March 2016