shikimic acid (CHEBI:16119)

ChEBI > Main

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

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

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

Wikipedia	License

Read full article at Wikipedia

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

Citations

Last Modified

11 March 2016