Microbial
Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-05 22:47:39 UTC
Update Date2025-10-07 16:08:20 UTC
Metabolite IDMMDBc0054036
Metabolite Identification
Common Name(2E,6E,10E)-geranylgeranyl diphosphate
Description(2E,6E,10E)-geranylgeranyl diphosphate is a terpenoid, specifically a type of isoprenoid, that serves as a key intermediate in the biosynthesis of various terpenes and terpenoids. Its chemical structure features a long carbon chain with multiple double bonds, characteristic of the geranylgeranyl group, which is crucial for the synthesis of larger terpenes. In biological pathways, (2E,6E,10E)-geranylgeranyl diphosphate is involved in the production of complex terpenes through enzymatic reactions facilitated by terpene synthases. For instance, heterologous expression of a GV-type terpene synthase named GiaTPS demonstrated that it utilizes (2E,6E,10E)-geranylgeranyl diphosphate as a substrate to generate a novel cyclized terpene compound, showcasing its role in the diversification of terpenoid structures (PMID:40795194 ). This compound's involvement in such pathways highlights its significance in the synthesis of bioactive molecules that may have ecological and pharmacological implications.
Structure
Synonyms
ValueSource
all-trans-Geranylgeranyl diphosphateChEBI
all-trans-Geranylgeranyl diphosphoric acidGenerator
all-trans-Geranyl-geranyl diphosphoric acidGenerator
2-trans,6-trans,10-trans-Geranylgeranyl diphosphoric acid(3-)Generator
Geranylgeranyl pyrophosphate, (Z,e,e)-isomerMeSH
Geranylgeranyl pyrophosphate, 14C-labeled, (e,e,e)-isomerMeSH
GGPP CPDMeSH
Geranylgeranyl pyrophosphateMeSH
Geranylgeraniol diphosphateMeSH
GGPP DiphosphateMeSH
Nerylneryl diphosphateMeSH
Geranylgeranyl diphosphateMeSH
Molecular FormulaC20H33O7P2
Average Mass447.426
Monoisotopic Mass447.171798138
IUPAC Name(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl (phosphonatooxy)phosphonate
Traditional Name(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl phosphonatooxyphosphonate
CAS Registry NumberNot Available
SMILES
[H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])COP([O-])(=O)OP([O-])([O-])=O)=C(\C)CCC=C(C)C
InChI Identifier
InChI=1S/C20H36O7P2/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-26-29(24,25)27-28(21,22)23/h9,11,13,15H,6-8,10,12,14,16H2,1-5H3,(H,24,25)(H2,21,22,23)/p-3/b18-11+,19-13+,20-15+
InChI KeyOINNEUNVOZHBOX-QIRCYJPOSA-K