Identification
YMDB IDYMDB00359
Name2-trans,6-trans,10-trans-geranylgeranyl diphosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2-trans,6-trans,10-trans-Geranylgeranyl diphosphate (GPP) is a crucial compound involved in the biosynthesis of a variety of terpenoids including chlorophylls, carotenoids, tocopherols, plastoquinones, and the plant hormones gibberellin and abscisic acid. GPP is also used in posttranslational modifications of proteins (geranylgeranylation) which is important for membrane adhesion as well as the function of some proteins. [Biocyc PWY-5120]
Structure
Thumb
Synonyms
  • all-trans-geranylgeranyl diphosphate
  • all-trans-geranylgeranyl pyrophosphate
  • Geranylgeranyl diphosphate
  • geranylgeranyl pyrophosphate
  • GGDP
  • ggpp
  • (2E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraen-1-yl diphosphate
  • all-trans-Geranylgeranyl diphosphoric acid
  • all-trans-Geranylgeranyl pyrophosphoric acid
  • Geranylgeranyl diphosphoric acid
  • Geranylgeranyl pyrophosphoric acid
  • (2E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraen-1-yl diphosphoric acid
  • 2-trans,6-trans,10-trans-Geranylgeranyl diphosphate
  • 3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenyl diphosphate
  • all-trans-Geranyl-geranyl-PP
  • Geranylgeranyl-diphosphate
  • Geranylgeraniol diphosphate
  • Geranylgeranyl pyrophosphate, (Z,e,e)-isomer
  • Nerylneryl diphosphate
  • GGPP Diphosphate
  • Geranylgeranyl pyrophosphate, 14C-labeled, (e,e,e)-isomer
  • GGPP CPD
CAS number6699-20-3
WeightAverage: 450.4432
Monoisotopic: 450.19362653
InChI KeyOINNEUNVOZHBOX-QIRCYJPOSA-N
InChIInChI=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)/b18-11+,19-13+,20-15+
IUPAC Name{[hydroxy({[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]oxy})phosphoryl]oxy}phosphonic acid
Traditional IUPAC Namegeranylgeranyl diphosphate
Chemical FormulaC20H36O7P2
SMILESCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentAcyclic diterpenoids
Alternative Parents
Substituents
  • Acyclic diterpenoid
  • Organic pyrophosphate
  • Isoprenoid phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0046 g/LALOGPS
logP3.57ALOGPS
logP5.28ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity120.53 m³·mol⁻¹ChemAxon
Polarizability47.82 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Terpenoid backbone biosynthesisPW002485 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Terpenoid backbone biosynthesisec00900 Map00900
SMPDB Reactions
Farnesyl pyrophosphate + Isopentenyl pyrophosphatePyrophosphate + 2-trans,6-trans,10-trans-geranylgeranyl diphosphate
KEGG Reactions
2-trans,6-trans-farnesyl diphosphate + Isopentenyl pyrophosphatePyrophosphate + 2-trans,6-trans,10-trans-geranylgeranyl diphosphate
2-trans,6-trans,10-trans-geranylgeranyl diphosphate + Isopentenyl pyrophosphatePyrophosphate + pentaprenyl diphosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00p1-8966200000-998d239f267a150b43edJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-0002-0000900000-e7c9a733fcef12117c3dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 15V, negativesplash10-0002-1000900000-51a8d5ce498d65e79691JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 19V, negativesplash10-004j-9000800000-4beea4fd2eb20ffa4ad9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 26V, negativesplash10-004i-9000000000-4db0a53ff36e5e4b9935JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 31V, negativesplash10-004i-9000000000-cf199ce4e78be9534fb7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 37V, negativesplash10-004i-9000000000-7867ab9db012f87e43c8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 44V, negativesplash10-004i-9000000000-be17e3662a7647d871aaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 52V, negativesplash10-004i-9000000000-1f4ff46767d08f6c4824JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 60V, negativesplash10-004i-9000000000-d99bb72e9136380d8698JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 72V, negativesplash10-004i-9000000000-d99bb72e9136380d8698JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 31V, negativesplash10-001i-0300900000-fecb2380f7e0ec863abcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 31V, negativesplash10-004i-9000000000-5ef060d5ec4b80c35c1aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 31V, negativesplash10-0a4i-0900000000-dc954ce23ecf1a263189JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 31V, negativesplash10-0a4i-0900000000-8ab5606bd668c2535e4dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 31V, negativesplash10-004i-9000000000-5ef060d5ec4b80c35c1aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-1394600000-c6d91e9bfb5eeb46563eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-3592000000-c8aa1820057f6139aad8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xs-5690000000-5fa48d769648b6310c2dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0400900000-86700e111b6b2b0215c0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-7900100000-c5c0d2a89df8d138cebbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-0ec0eed3d4d479d9c002JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1214900000-f698165f4dfead7c9d55JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1189100000-6a265357a808fdf96bf8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05s1-3910000000-59003e6f3766239ee38aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-582b037b919c4a7e747fJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID48861
HMDB IDHMDB0004486
Pubchem Compound ID447277
Kegg IDC00353
ChemSpider ID23092869
FOODB IDFDB023377
Wikipedia IDNot Available
BioCyc IDGERANYLGERANYL-PP

Enzymes

General function:
Involved in isoprenoid biosynthetic process
Specific function:
Catalyzes the trans-addition of the 3 molecules of IPP onto DMAPP to form geranylgeranyl pyrophosphate. Required for the membrane attachment of YPT1 and SEC4. May be involved in vesicle trafficking and protein sorting
Gene Name:
BTS1
Uniprot ID:
Q12051
Molecular weight:
38651.0
Reactions
Dimethylallyl diphosphate + isopentenyl diphosphate → diphosphate + geranyl diphosphate.
Geranyl diphosphate + isopentenyl diphosphate → diphosphate + (2E,6E)-farnesyl diphosphate.
Trans,trans-farnesyl diphosphate + isopentenyl diphosphate → diphosphate + geranylgeranyl diphosphate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the transfer of a geranyl-geranyl moiety from geranyl-geranyl pyrophosphate to proteins having the C-terminal sequence Cys-Ile-Ile-Leu or Cys-Val-Leu-Leu. Acts, among other substrates, on Rho1 and Rho2 and CDC42 proteins. Participates in a RAS-like C-terminal modification of proteins involved in nuclear division and bud growth. It is involved in bud positioning and cell polarity
Gene Name:
CDC43
Uniprot ID:
P18898
Molecular weight:
42689.10156
Reactions
Geranylgeranyl diphosphate + protein-cysteine → S-geranylgeranyl-protein + diphosphate.
General function:
Involved in protein prenyltransferase activity
Specific function:
Catalyzes the transfer of a farnesyl or geranyl-geranyl moiety from farnesyl or geranyl-geranyl pyrophosphate to a cysteine at the fourth position from the C-terminus of several proteins having the C-terminal sequence Cys-aliphatic-aliphatic-X. The alpha subunit is thought to participate in a stable complex with the substrate. The beta subunit binds the peptide substrate
Gene Name:
RAM2
Uniprot ID:
P29703
Molecular weight:
37507.30078
Reactions
Farnesyl diphosphate + protein-cysteine → S-farnesyl protein + diphosphate.
Geranylgeranyl diphosphate + protein-cysteine → S-geranylgeranyl-protein + diphosphate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the transfer of a geranyl-geranyl moiety from geranyl-geranyl pyrophosphate to proteins having the C-terminal -XCC or -XCXC, where both cysteines may become modified. Acts on YPT1 and SEC4
Gene Name:
BET2
Uniprot ID:
P20133
Molecular weight:
36665.60156
Reactions
Geranylgeranyl diphosphate + protein-cysteine → S-geranylgeranyl-protein + diphosphate.
General function:
Involved in protein prenyltransferase activity
Specific function:
Catalyzes the transfer of a geranyl-geranyl moiety from geranyl-geranyl pyrophosphate to proteins having the C-terminal -XCC or -XCXC, where both cysteines may become modified. Acts on YPT1 and SEC4
Gene Name:
BET4
Uniprot ID:
Q00618
Molecular weight:
39674.30078
Reactions
Geranylgeranyl diphosphate + protein-cysteine → S-geranylgeranyl-protein + diphosphate.