Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.

Record Information
Version	2.0
Creation Date	2012-05-31 13:49:08 -0600
Update Date	2015-09-13 12:56:10 -0600
Secondary Accession Numbers	ECMDB01285
Identification
Name:	Geranyl-PP
Description	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 E.coli, geranyl diphosphate synthase (GPPS) catalyzes the condensation of dimethylallyl diphosphate (DMAPP) and isopentenyl diphosphate (IPP) to form geranyl diphosphate. Geranyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. (Wikipedia)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x9031afac> Close
Synonyms:	ω,E-geranyl diphosphate ω,e-geranyl diphosphoric acid (2E)-3,7-dimethylocta-2,6-dien-1-yl trihydrogen diphosphate (2E)-3,7-Dimethylocta-2,6-dien-1-yl trihydrogen diphosphoric acid Geranyl diphosphate Geranyl diphosphoric acid Geranyl pyrophosphate Geranyl pyrophosphoric acid Geranyl-diphosphate Geranyl-diphosphoric acid Geranyl-PP Geranyl-pyrophosphate Geranyl-pyrophosphoric acid GPP Monoterpenyl diphosphate Monoterpenyl diphosphoric acid Neryl diphosphate Neryl diphosphoric acid Omega,E-geranyl diphosphate Omega,e-geranyl diphosphoric acid Trans-Geranyl pyrophosphate trans-Geranyl pyrophosphoric acid
Chemical Formula:	C10H20O7P2
Weight:	Average: 314.2091 Monoisotopic: 314.068426018
InChI Key:	GVVPGTZRZFNKDS-JXMROGBWSA-N
InChI:	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+
CAS number:	763-10-0
IUPAC Name:	[({[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid
Traditional IUPAC Name:	geranyl diphosphate
SMILES:	CC(C)=CCC\C(C)=C\CO[P@@](=O)(O)OP(=O)(O)O
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.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Prenol lipids
Sub Class	Isoprenoid phosphates
Direct Parent	Isoprenoid phosphates
Alternative Parents	Organic pyrophosphates Acyclic monoterpenoids Monoalkyl phosphates Organooxygen compounds Organic oxides Hydrocarbon derivatives
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 Framework	Aliphatic acyclic compounds
External Descriptors	polyprenol diphosphate (CHEBI:17211 ) Acyclic monoterpenoids (C00341 ) Linear monoterpenes (C00341 ) Acyclic monoterpenoids (LMPR0102010001 )
Physical Properties
State:	Solid
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.9 g/L ALOGPS logP 1.63 ALOGPS logP 1.96 ChemAxon logS -2.5 ALOGPS pKa (Strongest Acidic) 1.77 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 113.29 Ų ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 72.93 m³·mol⁻¹ ChemAxon Polarizability 28.52 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Dimethylallylpyrophosphate + Isopentenyl pyrophosphate > Geranyl-PP + Pyrophosphate Geranyl-PP + Isopentenyl pyrophosphate + Geranyl diphosphate <> Farnesyl pyrophosphate + Pyrophosphate Dimethylallylpyrophosphate + Isopentenyl pyrophosphate <> Pyrophosphate + Geranyl-PP Geranyl-PP + Isopentenyl pyrophosphate <> Pyrophosphate + Farnesyl pyrophosphate all-trans-Polyprenyl diphosphate + 4-Hydroxybenzoic acid + Geranyl-PP <> 4-Hydroxy-3-polyprenylbenzoate + Pyrophosphate + 4-Hydroxy-3-polyprenylbenzoate Geranyl-PP + Isopentenyl pyrophosphate > Farnesyl pyrophosphate + Pyrophosphate Geranyl-PP + 1,4-Dihydroxy-2-naphthoic acid <> Demethylmenaquinol + Pyrophosphate + Carbon dioxide Dimethylallylpyrophosphate + Isopentenyl pyrophosphate + Dimethylallylpyrophosphate + Isopentenyl pyrophosphate > Pyrophosphate + Geranyl-PP + Geranyl-PP Geranyl-PP + Isopentenyl pyrophosphate + Geranyl-PP + Isopentenyl pyrophosphate > Pyrophosphate + Farnesyl pyrophosphate + Farnesyl pyrophosphate Dimethylallylpyrophosphate + Isopentenyl pyrophosphate > Geranyl-PP + Pyrophosphate Dimethylallylpyrophosphate + Isopentenyl pyrophosphate > Geranyl-PP + Pyrophosphate
SMPDB Pathways:	Secondary metabolites: methylerythritol phosphate and polyisoprenoid biosynthesis PW000958
KEGG Pathways:	Metabolic pathways eco01100 Terpenoid backbone biosynthesis ec00900 Ubiquinone and other terpenoid-quinone biosynthesis ec00130
EcoCyc Pathways:	trans, trans-farnesyl diphosphate biosynthesis PWY-5123
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-004j-9640000000-9ce32c835bdcfa97fa15 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Orbitrap 6V, negative splash10-0002-0090000000-b5ca864b0ba8818ad627 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 8V, negative splash10-0002-0090000000-c7f7c5c529a56d532304 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 11V, negative splash10-0002-3390000000-010bee66d1e4bd685e95 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 14V, negative splash10-004i-9440000000-13e525f66230aae586a2 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 17V, negative splash10-004i-9200000000-a9da8f03edb73eec50bf View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 20V, negative splash10-004i-9100000000-fe3060700600ee72f8dd View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 23V, negative splash10-004i-9000000000-15de26c097afd86b7007 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 27V, negative splash10-004i-9000000000-bcc45bf0bf3bbb46af13 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 33V, negative splash10-004i-9000000000-b8b56dc9ea06c2ce52b5 View in MoNA LC-MS/MS LC-MS/MS Spectrum - n/a 21V, negative splash10-0a4i-0900000000-f2685d197409ed952f02 View in MoNA LC-MS/MS LC-MS/MS Spectrum - n/a 21V, negative splash10-004i-9000000000-5ef060d5ec4b80c35c1a View in MoNA LC-MS/MS LC-MS/MS Spectrum - n/a 21V, negative splash10-0a4i-0900000000-60b9e910670cbc6ebe0c View in MoNA LC-MS/MS LC-MS/MS Spectrum - n/a 21V, negative splash10-0bt9-0390000000-6532032bbb594aa54d9c View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 5V, negative splash10-03di-0009000000-3bcab8c3688c96a4cec5 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 7V, negative splash10-03di-2009000000-42fa98db20ae4d6f687e View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 9V, negative splash10-01t9-9005000000-44618200345aed481b48 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 12V, negative splash10-004i-9000000000-befed7a961a777eb5f66 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 15V, negative splash10-004i-9000000000-8afaaf750b51acbd1a01 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 18V, negative splash10-004i-9000000000-b5b3b346fecad6ae473d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00kr-1953000000-e5ee3340554c9ecac23e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-5910000000-82bcd2195a53b847981c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0gc0-9400000000-f87d391f1b3c01743515 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03di-0509000000-43083a162145718cd977 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9500000000-053b6323e620a16328a8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-4faed4c921d605619caf View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Barnard GF, Popjak G: Human liver prenyltransferase and its characterization. Biochim Biophys Acta. 1981 Sep 15;661(1):87-99. Pubmed: 7295734 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 Holstein SA, Hohl RJ: Isoprenoids: remarkable diversity of form and function. Lipids. 2004 Apr;39(4):293-309. Pubmed: 15357017 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 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 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882 Loza-Tavera H: Monoterpenes in essential oils. Biosynthesis and properties. Adv Exp Med Biol. 1999;464:49-62. Pubmed: 10335385 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 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 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 Smit A, Mushegian A: Biosynthesis of isoprenoids via mevalonate in Archaea: the lost pathway. Genome Res. 2000 Oct;10(10):1468-84. Pubmed: 11042147 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:	Runquist 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)
Links
External Links:	Resource Link CHEBI ID 17211 HMDB ID HMDB01285 Pubchem Compound ID 445995 Kegg ID C05847 ChemSpider ID 393471 Wikipedia Geranyl pyrophosphate BioCyc ID GERANYL-PP EcoCyc ID GERANYL-PP Ligand Expo GPP

Enzymes