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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 19:43:10 UTC
Update Date2020-03-11 15:23:05 UTC
HMDB IDHMDB0004486
Secondary Accession Numbers
  • HMDB0060109
  • HMDB04486
  • HMDB60109
Metabolite Identification
Common NameGeranylgeranyl-PP
DescriptionGeranylgeranyl pyrophosphate, also known as geranylgeranyl-PP or GGPP, is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. This compound belongs to the family of acyclic diterpenes. These are diterpenes (compounds made of four consecutive isoprene units) that do not contain a cycle. Thus, GGPP is considered to be an isoprenoid lipid molecule. GGPP is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1583940185
Synonyms
ValueSource
all-trans-Geranylgeranyl diphosphateChEBI
all-trans-Geranylgeranyl pyrophosphateChEBI
Geranylgeranyl diphosphateChEBI
Geranylgeranyl pyrophosphateChEBI
GGDPChEBI
(2E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraen-1-yl diphosphateKegg
all-trans-Geranylgeranyl diphosphoric acidGenerator
all-trans-Geranylgeranyl pyrophosphoric acidGenerator
Geranylgeranyl diphosphoric acidGenerator
Geranylgeranyl pyrophosphoric acidGenerator
(2E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraen-1-yl diphosphoric acidGenerator
2-trans,6-trans,10-trans-Geranylgeranyl diphosphateHMDB
3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenyl diphosphateHMDB
all-trans-Geranyl-geranyl-PPHMDB
Geranylgeranyl-diphosphateHMDB
Geranylgeraniol diphosphateHMDB
Geranylgeranyl pyrophosphate, (Z,e,e)-isomerHMDB
Nerylneryl diphosphateHMDB
GGPP DiphosphateHMDB
Geranylgeranyl pyrophosphate, 14C-labeled, (e,e,e)-isomerHMDB
GGPP CPDHMDB
Chemical FormulaC20H36O7P2
Average Molecular Weight450.4432
Monoisotopic Molecular Weight450.19362653
IUPAC Name{[hydroxy({[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]oxy})phosphoryl]oxy}phosphonic acid
Traditional Namegeranylgeranyl diphosphate
CAS Registry Number6699-20-3
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O
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)/b18-11+,19-13+,20-15+
InChI KeyOINNEUNVOZHBOX-QIRCYJPOSA-N
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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0046 g/LALOGPS
logP10(3.57) g/LALOGPS
logP10(5.28) g/LChemAxon
logS10(-5) g/LALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+204.70831661259
DarkChem[M-H]-197.25931661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Geranylgeranyl-PP GC-MS (Non-derivatized) - 70eV, Positivesplash10-00p1-8966200000-998d239f267a150b43ed2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Geranylgeranyl-PP GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Geranylgeranyl-PP Orbitrap 11V, negative-QTOFsplash10-0002-0000900000-e7c9a733fcef12117c3d2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Geranylgeranyl-PP Orbitrap 15V, negative-QTOFsplash10-0002-1000900000-51a8d5ce498d65e796912020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Geranylgeranyl-PP Orbitrap 19V, negative-QTOFsplash10-004j-9000800000-4beea4fd2eb20ffa4ad92020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Geranylgeranyl-PP Orbitrap 26V, negative-QTOFsplash10-004i-9000000000-4db0a53ff36e5e4b99352020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Geranylgeranyl-PP Orbitrap 31V, negative-QTOFsplash10-004i-9000000000-cf199ce4e78be9534fb72020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Geranylgeranyl-PP Orbitrap 37V, negative-QTOFsplash10-004i-9000000000-7867ab9db012f87e43c82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Geranylgeranyl-PP Orbitrap 44V, negative-QTOFsplash10-004i-9000000000-be17e3662a7647d871aa2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Geranylgeranyl-PP Orbitrap 52V, negative-QTOFsplash10-004i-9000000000-1f4ff46767d08f6c48242020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Geranylgeranyl-PP Orbitrap 60V, negative-QTOFsplash10-004i-9000000000-d99bb72e9136380d86982020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Geranylgeranyl-PP Orbitrap 72V, negative-QTOFsplash10-004i-9000000000-d99bb72e9136380d86982020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Geranylgeranyl-PP n/a 31V, negative-QTOFsplash10-001i-0300900000-fecb2380f7e0ec863abc2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Geranylgeranyl-PP n/a 31V, negative-QTOFsplash10-004i-9000000000-5ef060d5ec4b80c35c1a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Geranylgeranyl-PP n/a 31V, negative-QTOFsplash10-0a4i-0900000000-dc954ce23ecf1a2631892020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Geranylgeranyl-PP n/a 31V, negative-QTOFsplash10-0a4i-0900000000-8ab5606bd668c2535e4d2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Geranylgeranyl-PP n/a 31V, negative-QTOFsplash10-004i-9000000000-5ef060d5ec4b80c35c1a2020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geranylgeranyl-PP 10V, Positive-QTOFsplash10-0fk9-1394600000-c6d91e9bfb5eeb46563e2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geranylgeranyl-PP 20V, Positive-QTOFsplash10-00di-3592000000-c8aa1820057f6139aad82016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geranylgeranyl-PP 40V, Positive-QTOFsplash10-00xs-5690000000-5fa48d769648b6310c2d2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geranylgeranyl-PP 10V, Negative-QTOFsplash10-0002-0400900000-86700e111b6b2b0215c02016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geranylgeranyl-PP 20V, Negative-QTOFsplash10-057i-7900100000-c5c0d2a89df8d138cebb2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geranylgeranyl-PP 40V, Negative-QTOFsplash10-004i-9000000000-0ec0eed3d4d479d9c0022016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geranylgeranyl-PP 10V, Positive-QTOFsplash10-0udi-1214900000-f698165f4dfead7c9d552021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geranylgeranyl-PP 20V, Positive-QTOFsplash10-00di-1189100000-6a265357a808fdf96bf82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geranylgeranyl-PP 40V, Positive-QTOFsplash10-05s1-3910000000-59003e6f3766239ee38a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geranylgeranyl-PP 10V, Negative-QTOFsplash10-0002-0000900000-582b037b919c4a7e747f2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023377
KNApSAcK IDC00000908
Chemspider ID394418
KEGG Compound IDC00353
BioCyc IDGERANYLGERANYL-PP
BiGG ID1759656
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound447277
PDB IDGRG
ChEBI ID48861
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Denis M, Bissonnette R, Haidar B, Krimbou L, Bouvier M, Genest J: Expression, regulation, and activity of ABCA1 in human cell lines. Mol Genet Metab. 2003 Apr;78(4):265-74. [PubMed:12706378 ]
  2. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]

Enzymes

General function:
Involved in isoprenoid biosynthetic process
Specific function:
Catalyzes the trans-addition of the three molecules of IPP onto DMAPP to form geranylgeranyl pyrophosphate, an important precursor of carotenoids and geranylated proteins.
Gene Name:
GGPS1
Uniprot ID:
O95749
Molecular weight:
34870.625
Reactions
Farnesyl pyrophosphate + Isopentenyl pyrophosphate → Pyrophosphate + Geranylgeranyl-PPdetails
General function:
Involved in CAAX-protein geranylgeranyltransferase acti
Specific function:
Catalyzes the transfer of a geranyl-geranyl moiety from geranyl-geranyl pyrophosphate to a cysteine at the fourth position from the C-terminus of proteins having the C-terminal sequence Cys-aliphatic-aliphatic-X. Acts on the Rac1, Rac2, Rap1A and Rap1B proteins. The beta subunit is responsible for peptide-binding.
Gene Name:
PGGT1B
Uniprot ID:
P53609
Molecular weight:
42367.81
Reactions
Geranylgeranyl-PP + protein-cysteine → S-geranylgeranyl-protein + Pyrophosphatedetails
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. Through RAC1 prenylation and activation may positively regulate neuromuscular junction development downstream of MUSK (By similarity).
Gene Name:
FNTA
Uniprot ID:
P49354
Molecular weight:
44408.32
Reactions
Geranylgeranyl-PP + protein-cysteine → S-geranylgeranyl-protein + Pyrophosphatedetails
General function:
Not Available
Specific function:
Catalyzes the transfer of a geranyl-geranyl moiety from geranyl-geranyl pyrophosphate to both cysteines in Rab proteins with an -XXCC, -XCXC and -CCXX C-terminal, such as RAB1A, RAB3A and RAB5A respectively.
Gene Name:
RABGGTA
Uniprot ID:
Q92696
Molecular weight:
65071.06
Reactions
Geranylgeranyl-PP + protein-cysteine → S-geranylgeranyl-protein + Pyrophosphatedetails
General function:
Not Available
Specific function:
Catalyzes the transfer of a geranyl-geranyl moiety from geranyl-geranyl pyrophosphate to both cysteines in Rab proteins with an -XXCC, -XCXC and -CCXX C-terminal, such as RAB1A, RAB3A and RAB5A respectively.
Gene Name:
RABGGTB
Uniprot ID:
P53611
Molecular weight:
36924.04
Reactions
Geranylgeranyl-PP + protein-cysteine → S-geranylgeranyl-protein + Pyrophosphatedetails