geranyl diphosphate





Description


Geranyl diphosphate (GPP) is a precursor molecule in the biosynthesis of various terpenoids and essential oils found in plants. It is a diphosphate ester composed of two isoprene units (C10H16) linked by a phosphoanhydride bond. Geranyl diphosphate is synthesized from isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP) via the enzyme geranyl diphosphate synthase. Once formed, geranyl diphosphate can undergo a series of reactions catalyzed by different enzymes to produce a wide range of terpenoids, including monoterpenes, sesquiterpenes, and diterpenes. For example, geranyl diphosphate can be converted into limonene, a monoterpene found in citrus fruits and other plants, or into farnesyl diphosphate, a precursor of various sesquiterpenes and diterpenes. In addition to their roles in plant metabolism, terpenoids have many commercial applications, such as in the production of fragrances, flavors, and pharmaceuticals.


Chemical Formula:
C10H17O7P2
Molecular Weight:
311.188 Daltons
Monoisotopic Mass:
314.0684260167 Daltons
SMILES:
CC(=CCCC(=CCOP([O-])(OP(=O)([O-])[O-])=O)C)C
InChI:
1S/C10H20O7P2/c1-9(2)5-4-6-10(3)7-8-16-19(14,15)17-18(11,12)13/h5,7H,4,6,8H2,1-3H3,(H,14,15)(H2,11,12,13)/p-3/b10-7+

Synonyms
  • geranyl-diphosphate
  • geranyl-pyrophosphate
  • GPP
  • geranyl-PP
  • geranyl pyrophosphate
  • ω,E-geranyl diphosphate

Databases
MetaCyc:  GERANYL-PP
BiGG:  grdp
MetaboLights:  MTBLC58057
HMDB:  HMDB01285
ChemSpider:  14211068
ChEBI:  58057 17211
KNApSAcK:  C00000846
PubChem (CID):  19379894
KEGG:  C00341
PupChem (SID):  3634
CHEMBL:  CHEMBL41342
LIPID MAPS:  LMPR0102010001
LIPIDBANK:  IIP0003
PDB-CCD:  GPP
3DMET:  B00091
NIKKAJI:  J1.452.575K J39.583H
Reactome:  191409
MetaNetX:  MNXM100