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Record Information
Version4.0
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

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00p1-8966200000-998d239f267a150b43edSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-0002-0000900000-e7c9a733fcef12117c3dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 15V, negativesplash10-0002-1000900000-51a8d5ce498d65e79691Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 19V, negativesplash10-004j-9000800000-4beea4fd2eb20ffa4ad9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 26V, negativesplash10-004i-9000000000-4db0a53ff36e5e4b9935Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 31V, negativesplash10-004i-9000000000-cf199ce4e78be9534fb7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 37V, negativesplash10-004i-9000000000-7867ab9db012f87e43c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 44V, negativesplash10-004i-9000000000-be17e3662a7647d871aaSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 52V, negativesplash10-004i-9000000000-1f4ff46767d08f6c4824Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 60V, negativesplash10-004i-9000000000-d99bb72e9136380d8698Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 72V, negativesplash10-004i-9000000000-d99bb72e9136380d8698Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 31V, negativesplash10-001i-0300900000-fecb2380f7e0ec863abcSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 31V, negativesplash10-004i-9000000000-5ef060d5ec4b80c35c1aSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 31V, negativesplash10-0a4i-0900000000-dc954ce23ecf1a263189Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 31V, negativesplash10-0a4i-0900000000-8ab5606bd668c2535e4dSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 31V, negativesplash10-004i-9000000000-5ef060d5ec4b80c35c1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-1394600000-c6d91e9bfb5eeb46563eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-3592000000-c8aa1820057f6139aad8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xs-5690000000-5fa48d769648b6310c2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0400900000-86700e111b6b2b0215c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-7900100000-c5c0d2a89df8d138cebbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-0ec0eed3d4d479d9c002Spectrum
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 ID
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