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

Supplier Information	ChemicalBook:CB41124723, ChemicalBook:CB8400042, ChemicalBook:CB1400043, eMolecules:901780

Download	Molfile XML SDF

Wikipedia	License
Nicotinamide (INN, BAN UK) or niacinamide (USAN US) is a form of vitamin B3 found in food and used as a dietary supplement and medication. As a supplement, it is used orally (swallowed by mouth) to prevent and treat pellagra (niacin deficiency). While nicotinic acid (niacin) may be used for this purpose, nicotinamide has the benefit of not causing skin flushing. As a cream, it is used to treat acne, and has been observed in clinical studies to improve the appearance of aging skin by reducing hyperpigmentation and redness. It is a water-soluble vitamin. Side effects are minimal. At high doses, liver problems may occur. Normal amounts are safe for use during pregnancy. Nicotinamide is in the vitamin B family of medications, specifically the vitamin B3 complex. It is an amide of nicotinic acid. Foods that contain nicotinamide include yeast, meat, milk, and green vegetables. Nicotinamide was discovered between 1935 and 1937. It is on the World Health Organization's List of Essential Medicines. Nicotinamide is available as a generic medication and over the counter. Commercially, nicotinamide is made from either nicotinic acid (niacin) or nicotinonitrile. In some countries, grains have nicotinamide added to them. Extra-terrestrial nicotinamide has been found in carbonaceous chondrite meteorites.
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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).