3-dehydroshikimic acid (CHEBI:30918)

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ChEBI Name	3-dehydroshikimic acid

ChEBI ID	CHEBI:30918

Definition	A 4-oxo monocarboxylic acid that is shikimic acid in which the allylic hydroxy group has been oxidised to the corresponding keto group.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:42005, CHEBI:2052, CHEBI:1488, CHEBI:19999

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Formula

C7H8O5

Net Charge

Average Mass

172.13540

Monoisotopic Mass

172.03717

InChI

InChI=1S/C7H8O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,5-6,9-10H,2H2,(H,11,12)/t5-,6-/m1/s1

InChIKey

SLWWJZMPHJJOPH-PHDIDXHHSA-N

SMILES

O[C@@H]1CC(=CC(=O)[C@H]1O)C(O)=O

Metabolite of Species	Details
Centella asiatica (NCBI:txid48106)	See: MetaboLights Study

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):	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	3-dehydroshikimic acid (CHEBI:30918) has functional parent shikimic acid (CHEBI:16119) 3-dehydroshikimic acid (CHEBI:30918) has role plant metabolite (CHEBI:76924) 3-dehydroshikimic acid (CHEBI:30918) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020) 3-dehydroshikimic acid (CHEBI:30918) is a 4-hydroxy monocarboxylic acid (CHEBI:35970) 3-dehydroshikimic acid (CHEBI:30918) is a 4-oxo monocarboxylic acid (CHEBI:35950) 3-dehydroshikimic acid (CHEBI:30918) is a 5-hydroxy monocarboxylic acid (CHEBI:37125) 3-dehydroshikimic acid (CHEBI:30918) is a secondary α-hydroxy ketone (CHEBI:2468) 3-dehydroshikimic acid (CHEBI:30918) is conjugate acid of 3-dehydroshikimate (CHEBI:16630)

Incoming	3-dehydroshikimate (CHEBI:16630) is conjugate base of 3-dehydroshikimic acid (CHEBI:30918)

IUPAC Name

(4S,5R)-4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid

Registry Number	Type	Source
2938338	Reaxys Registry Number	Reaxys

Citation	Type	Source
10514257	PubMed citation	Europe PMC

Last Modified

18 August 2023

General Comment
2005-03-22	The numbering system used for the 3-dehydroshikimic acid is that of the IUPAC/CBN recommendations on cyclitols, sections I-8 and I-9. The use of the term '5-dehydroshikimic acid' for this compound is based on an earlier, now obsolete, system of numbering (for example of use, see S. Mitsuhashi and B. D. Davis, Biochim. Biophys. Acta, 1954, 15, 268-280).