Accession Number: pdtdbl00093

Details of the Ligand

Ligand Name : Zingiberene
Systematic Names : Zingiberene; alpha-Zingiberene; (5R)-2-methyl-5-[(2S)-6-methylhept-5-en-2-yl]cyclohexa-1,3-diene; (-)-Zingiberene; Zingiberene from ginger
Molecular Formula : C15H24
Molecular Weight : g/mol
IUPAC Name : (5R)-2-methyl-5-[(2S)-6-methylhept-5-en-2-yl]cyclohexa-1,3-diene
Canonical SMILES : CC1=CCC(C=C1)C(C)CCC=C(C)C
Ligand Description :

Zingiberene is a monocyclic sesquiterpene that is the predominant constituent of the oil of ginger (Zingiber officinale), from which it gets its name. It can contribute up to 30% of the essential oils in ginger rhizomes. This is the compound that gives ginger its distinct flavoring.

Zingiberene is formed in the isoprenoid pathway from farnesyl pyrophosphate (FPP). FPP undergoes a rearrangement to give nerolidyl diphosphate. After the removal of pyrophosphate, the ring closes leaving a carbocation on the tertiary carbon attached to the ring. A 1,3-hydride shift then takes place to give a more stable allylic carbocation. The final step in the formation of zingiberene is the removal of the cyclic allylic proton and consequent formation of a double bond. Zingiberene synthase is the enzyme responsible for catalyzing the reaction forming zingiberene as well as other mono- and sesquiterpenes.

Related Plants :
Ligand Related Dockings :
NA
Ligand References :
  1. https://en.wikipedia.org/wiki/Zingiberene
  2. https://pubchem.ncbi.nlm.nih.gov/compound/Zingiberene
  3. http://chem.sis.nlm.nih.gov/chemidplus/name/zingiberene
Zingiberene

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