CHEBI:30918 - 3-dehydroshikimic acid

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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 0
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.
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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
Synonyms Sources
(−)-3-dehydroshikimic acid ChEBI
3-Dehydroshikimate KEGG COMPOUND
3-dehydroshikimic acid ChEBI
5-Dehydroshikimate KEGG COMPOUND
5-dehydroshikimic acid ChEBI
Manual Xrefs Databases
3-Dehydroshikimic_acid Wikipedia
C00019663 KNApSAcK
C02637 KEGG COMPOUND
DB04347 DrugBank
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Registry Number Type Source
2938338 Reaxys Registry Number Reaxys
Citation Waiting for Citations 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).