3-dehydroshikimate





Description


3-dehydroshikimate (also known as DHS) is an intermediate compound in the shikimate pathway, a metabolic pathway found in bacteria, fungi, and plants that leads to the synthesis of aromatic amino acids, such as phenylalanine, tyrosine, and tryptophan. In the shikimate pathway, DHS is formed from shikimate-3-phosphate by the enzyme shikimate dehydrogenase. DHS is then converted into 3-dehydroquinate by the enzyme DHS dehydratase. 3-dehydroquinate is further processed to produce the aromatic amino acids. The shikimate pathway is an important target for herbicides and antimicrobial agents, as it is not found in animals, including humans. By inhibiting enzymes in the shikimate pathway, it is possible to selectively target the growth of weeds, pathogens, and parasites, without harming humans or other animals. For example, glyphosate, the active ingredient in the herbicide Roundup, inhibits the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS) in the shikimate pathway, leading to the death of plants that rely on this pathway for the synthesis of aromatic amino acids.


Chemical Formula:
C7H7O5
Molecular Weight:
171.129 Daltons
Monoisotopic Mass:
172.0371733673 Daltons
SMILES:
C([O-])(=O)C1(=CC(=O)C(O)C(O)C1)
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)/p-1/t5-,6-/m1/s1

Synonyms
  • 3-dehydroshikimic acid
  • 5-dehydroshikimic acid
  • 5-dehydroshikimate

Databases
MetaCyc:  3-DEHYDRO-SHIKIMATE
RefMet:  3-dehydroshikimate
BiGG:  3dhsk
ChemSpider:  4573915
ChEBI:  16630
PubChem (CID):  5460360
KEGG:  C02637
Reactome:  964941
Seed:  cpd01716
MetaNetX:  MNXM611