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

Supplier Information	ZINC000002522619

Download	Molfile XML SDF

Wikipedia	License
Deoxyuridine (dU) is a compound and a nucleoside. It belongs to a class of compounds known as Pyrimidine 2'-deoxyribonucleosides and closely resembles the chemical composition of uridine but without the presence of the 2' hydroxyl group. Idoxuridine and Trifluridine are variants of deoxyuridine used as antiviral drugs. They are similar enough to be incorporated as part of DNA replication, but they possess side groups on the uracil component (an iodine and a CF3 group, respectively), that prevent base pairing. A known use of dU is as a precursor in the synthesis of Edoxudine. This compound exists in all living organisms and can become part of DNA in both prokaryotic and eukaryotic cells through two mechanisms. The first is the removal of an amino group from cytosine to result in uracil and the second is the non-intentional incorporation of pyrimidine where thymine belongs in the DNA, resulting in dUMP. UMP synthase deficiency is a metabolic disorder in humans that involves deoxyuridine. Deoxyuridine can be toxic. It has also been found in several foods, which makes it a useful indicator for diseases through consumption of those foods.
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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