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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-06-30 18:40:48 UTC
HMDB IDHMDB0001285
Secondary Accession Numbers
  • HMDB0001560
  • HMDB0002239
  • HMDB0006506
  • HMDB01285
  • HMDB01560
  • HMDB02239
  • HMDB06506
Metabolite Identification
Common NameGeranyl-PP
DescriptionGeranyl diphosphate is the precursor of monoterpenes, a large family of natural occurring C10 compounds predominately found in plants and animals. Geranyl diphosphate is regarded as a key intermediate in the steroid, isoprene and terpene biosynthesis pathways and is used by organisms in the biosynthesis of farnesyl pyrophosphate, geranylgeranyl pyrophosphate, cholesterol, terpenes and terpenoids. (wikipedia). In humans, geranyl diphosphate synthase (GPPS) catalyzes the condensation of dimethylallyl diphosphate (DMAPP) and isopentenyl diphosphate (IPP) to form geranyl diphosphate. Animals produce IPP through the mevalonate (MVA) pathway. Isoprenoid compounds have been implicated in several human disease states including coronary heart disease, blindness, infectious hepatitis and cancer. Geranyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. -- Wikipedia .
Structure
Data?1593542448
Synonyms
ValueSource
Geranyl pyrophosphateChEBI
PolyisopentenylpyrophosphateKegg
PolyisopentenyldiphosphateKegg
trans-PolyisopentenyldiphosphateKegg
Polyprenyl diphosphateKegg
Geranyl pyrophosphoric acidGenerator
Polyisopentenylpyrophosphoric acidGenerator
Polyisopentenyldiphosphoric acidGenerator
trans-Polyisopentenyldiphosphoric acidGenerator
Polyprenyl diphosphoric acidGenerator
(2E)-3,7-Dimethylocta-2,6-dien-1-yl trihydrogen diphosphateHMDB
Geranyl diphosphateHMDB
Geranyl-diphosphateHMDB
Geranyl-pyrophosphateHMDB
Monoterpenyl diphosphateHMDB
Neryl diphosphateHMDB
trans-Geranyl pyrophosphateHMDB
P-[(2E)-3,7-Dimethyl-2,6-octadien-1-yl]diphosphoric acidHMDB
trans-geranyl-PPHMDB
Chemical FormulaC10H20O7P2
Average Molecular Weight314.2091
Monoisotopic Molecular Weight314.068426018
IUPAC Name[({[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid
Traditional Namegeranyl diphosphate
CAS Registry Number763-10-0
SMILES
CC(C)=CCC\C(C)=C\COP(O)(=O)OP(O)(O)=O
InChI Identifier
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)/b10-7+
InChI KeyGVVPGTZRZFNKDS-JXMROGBWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isoprenoid phosphates. These are prenol lipids containing a phosphate group linked to an isoprene (2-methylbuta-1,3-diene) unit.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassIsoprenoid phosphates
Direct ParentIsoprenoid phosphates
Alternative Parents
Substituents
  • Organic pyrophosphate
  • Monoterpenoid
  • Isoprenoid phosphate
  • Acyclic monoterpenoid
  • 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:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.9 g/LALOGPS
logP1.63ALOGPS
logP1.96ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity72.93 m³·mol⁻¹ChemAxon
Polarizability28.52 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
AllCCS[M-H]-ExperimentalNot Available167.0http://allccs.zhulab.cn/database/detail?ID=AllCCS00000241
DarkChem[M+H]+PredictedNot Available176.78331661259
DarkChem[M-H]-PredictedNot Available168.54731661259
AllCCS[M+H]+PredictedNot Available173.60432859911
AllCCS[M-H]-PredictedNot Available167.01432859911

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-9640000000-9ce32c835bdcfa97fa152016-09-22View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-0002-0090000000-b5ca864b0ba8818ad6272020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-0002-0090000000-c7f7c5c529a56d5323042020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-0002-3390000000-010bee66d1e4bd685e952020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-004i-9440000000-13e525f66230aae586a22020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 17V, negativesplash10-004i-9200000000-a9da8f03edb73eec50bf2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 20V, negativesplash10-004i-9100000000-fe3060700600ee72f8dd2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 23V, negativesplash10-004i-9000000000-15de26c097afd86b70072020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 27V, negativesplash10-004i-9000000000-bcc45bf0bf3bbb46af132020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 33V, negativesplash10-004i-9000000000-b8b56dc9ea06c2ce52b52020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-0a4i-0900000000-f2685d197409ed952f022020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-004i-9000000000-5ef060d5ec4b80c35c1a2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-0a4i-0900000000-60b9e910670cbc6ebe0c2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-0bt9-0390000000-6532032bbb594aa54d9c2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-03di-0009000000-3bcab8c3688c96a4cec52020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, negativesplash10-03di-2009000000-42fa98db20ae4d6f687e2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-01t9-9005000000-44618200345aed481b482020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 12V, negativesplash10-004i-9000000000-befed7a961a777eb5f662020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 15V, negativesplash10-004i-9000000000-8afaaf750b51acbd1a012020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 18V, negativesplash10-004i-9000000000-b5b3b346fecad6ae473d2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 21V, negativesplash10-004i-9000000000-71f08ee06355626ebfd62020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 25V, negativesplash10-004i-9000000000-b7f0efd9272b1a27eac42020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 28V, negativesplash10-004i-9000000000-d99bb72e9136380d86982020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 35V, negativesplash10-004i-9000000000-d99bb72e9136380d86982020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-052b-0980000000-e4e4fa6041e73c8c9b5c2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-0a4i-0900000000-416f4bc886d807f0201d2020-07-22View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
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 IDDB02552
Phenol Explorer Compound IDNot Available
FooDB IDFDB001463
KNApSAcK IDC00000846
Chemspider ID393471
KEGG Compound IDC05847
BioCyc IDGERANYL-PP
BiGG ID34712
Wikipedia LinkGeranyl_pyrophosphate
METLIN ID6134
PubChem Compound445995
PDB IDNot Available
ChEBI ID17211
Food Biomarker OntologyNot Available
VMH IDGRDP
MarkerDB IDNot Available
References
Synthesis ReferenceRunquist M; Ericsson J; Thelin A; Chojnacki T; Dallner G Biosynthesis of trans,trans,trans-geranylgeranyl diphosphate by the cytosolic fraction from rat tissues. Biochemical and biophysical research communications (1992), 186(1), 157-65.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Micali E, Chehade KA, Isaacs RJ, Andres DA, Spielmann HP: Protein farnesyltransferase isoprenoid substrate discrimination is dependent on isoprene double bonds and branched methyl groups. Biochemistry. 2001 Oct 16;40(41):12254-65. [PubMed:11591144 ]
  2. Kavanagh KL, Guo K, Dunford JE, Wu X, Knapp S, Ebetino FH, Rogers MJ, Russell RG, Oppermann U: The molecular mechanism of nitrogen-containing bisphosphonates as antiosteoporosis drugs. Proc Natl Acad Sci U S A. 2006 May 16;103(20):7829-34. Epub 2006 May 9. [PubMed:16684881 ]
  3. Holstein SA, Hohl RJ: Isoprenoids: remarkable diversity of form and function. Lipids. 2004 Apr;39(4):293-309. [PubMed:15357017 ]
  4. Gan X, Kaplan R, Menke JG, MacNaul K, Chen Y, Sparrow CP, Zhou G, Wright SD, Cai TQ: Dual mechanisms of ABCA1 regulation by geranylgeranyl pyrophosphate. J Biol Chem. 2001 Dec 28;276(52):48702-8. Epub 2001 Oct 18. [PubMed:11641412 ]
  5. Sagami H, Ogura K: [A new development in isoprenoid biochemistry brought by the discovery of prenylated proteins]. Seikagaku. 1994 Dec;66(12):1488-501. [PubMed:7884273 ]
  6. Loza-Tavera H: Monoterpenes in essential oils. Biosynthesis and properties. Adv Exp Med Biol. 1999;464:49-62. [PubMed:10335385 ]
  7. Barnard GF, Popjak G: Human liver prenyltransferase and its characterization. Biochim Biophys Acta. 1981 Sep 15;661(1):87-99. [PubMed:7295734 ]
  8. Pont F, Luciani B, Belmant C, Fournie JJ: Characterization of phosphoantigens by high-performance anion-exchange chromatography-electrospray ionization ion trap mass spectrometry and nanoelectrospray ionization ion trap mass spectrometry. Anal Chem. 2001 Aug 1;73(15):3562-9. [PubMed:11510819 ]
  9. Smit A, Mushegian A: Biosynthesis of isoprenoids via mevalonate in Archaea: the lost pathway. Genome Res. 2000 Oct;10(10):1468-84. [PubMed:11042147 ]

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
Dimethylallylpyrophosphate + Isopentenyl pyrophosphate → Pyrophosphate + Geranyl-PPdetails
Geranyl-PP + Isopentenyl pyrophosphate → Pyrophosphate + Farnesyl pyrophosphatedetails
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
General function:
Involved in isoprenoid biosynthetic process
Specific function:
Key enzyme in isoprenoid biosynthesis which catalyzes the formation of farnesyl diphosphate (FPP), a precursor for several classes of essential metabolites including sterols, dolichols, carotenoids, and ubiquinones. FPP also serves as substrate for protein farnesylation and geranylgeranylation. Catalyzes the sequential condensation of isopentenyl pyrophosphate with the allylic pyrophosphates, dimethylallyl pyrophosphate, and then with the resultant geranylpyrophosphate to the ultimate product farnesyl pyrophosphate.
Gene Name:
FDPS
Uniprot ID:
P14324
Molecular weight:
48275.03
Reactions
Dimethylallylpyrophosphate + Isopentenyl pyrophosphate → Pyrophosphate + Geranyl-PPdetails
Geranyl-PP + Isopentenyl pyrophosphate → Pyrophosphate + Farnesyl pyrophosphatedetails
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
General function:
Involved in prenyltransferase activity
Specific function:
Catalyzes the prenylation of para-hydroxybenzoate (PHB) with an all-trans polyprenyl group. Mediates the second step in the final reaction sequence of coenzyme Q (CoQ) biosynthesis, which is the condensation of the polyisoprenoid side chain with PHB.
Gene Name:
COQ2
Uniprot ID:
Q96H96
Molecular weight:
45593.67
Reactions
Geranyl-PP + 4-Hydroxybenzoic acid → 4-Hydroxy-3-polyprenylbenzoate + Pyrophosphatedetails