Record Information
Version2.0
Creation Date2012-05-31 13:02:37 -0600
Update Date2015-09-13 12:56:09 -0600
Secondary Accession Numbers
  • ECMDB00961
Identification
Name:Farnesyl pyrophosphate
DescriptionFarnesyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. -- Wikipedia
Structure
Thumb
Synonyms:
  • ω,E,E-farnesyl diphosphate
  • ω,e,e-farnesyl diphosphate
  • ω,e,e-farnesyl diphosphoric acid
  • (2E,6E)-Farnesyl diphosphate
  • (2E,6E)-Farnesyl diphosphoric acid
  • (2E,6E)-Farnesyl pyrophosphate
  • (2E,6E)-Farnesyl pyrophosphoric acid
  • (E,E)-farnesyl diphosphate
  • (all-E)-Farnesyl diphosphate
  • (all-e)-Farnesyl diphosphoric acid
  • (E,E)-Farnesyl diphosphate
  • (e,e)-Farnesyl diphosphoric acid
  • (E,E)-Farnesyl pyrophosphate
  • (e,e)-Farnesyl pyrophosphoric acid
  • 2-trans,6-trans-farnesyl diphosphate
  • 2-trans,6-trans-Farnesyl diphosphate
  • 2-trans,6-trans-Farnesyl diphosphoric acid
  • 2-trans,6-trans-Farnesyl pyrophosphate
  • 2-trans,6-trans-Farnesyl pyrophosphoric acid
  • all-trans-farnesyl diphosphate
  • trans, trans-farnesyl diphosphate
  • All-trans-farnesyl diphosphate
  • all-trans-Farnesyl diphosphoric acid
  • All-trans-Farnesyl pyrophosphate
  • all-trans-Farnesyl pyrophosphoric acid
  • Farnesyl diphosphate
  • Farnesyl diphosphoric acid
  • Farnesyl pyrophosphate
  • Farnesyl pyrophosphoric acid
  • Farnesyl-PP
  • FPP
  • Omega,E,E-farnesyl diphosphate
  • Omega,e,e-farnesyl diphosphoric acid
  • Trans, trans-Farnesyl diphosphate
  • trans, trans-Farnesyl diphosphoric acid
  • Trans-Farnesyl pyrophosphate
  • trans-Farnesyl pyrophosphoric acid
  • Trans-trans-Farnesyl diphosphate
  • trans-trans-Farnesyl diphosphoric acid
  • Trans-trans-Farnesyl pyrophosphate
  • trans-trans-Farnesyl pyrophosphoric acid
Chemical Formula:C15H28O7P2
Weight:Average: 382.3261
Monoisotopic: 382.131026274
InChI Key:VWFJDQUYCIWHTN-YFVJMOTDSA-N
InChI:InChI=1S/C15H28O7P2/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-21-24(19,20)22-23(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H,19,20)(H2,16,17,18)/b14-9+,15-11+
CAS number:13058-04-3
IUPAC Name:{[hydroxy({[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy})phosphoryl]oxy}phosphonic acid
Traditional IUPAC Name:farnesyl diphosphate
SMILES:CC(C)=CCC\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 sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Farsesane sesquiterpenoid
  • Sesquiterpenoid
  • 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
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.081 g/LALOGPS
logP2.4ALOGPS
logP3.62ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity96.73 m³·mol⁻¹ChemAxon
Polarizability37.94 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate >8 Pyrophosphate + Undecaprenyl diphosphate
Geranyl-PP + Isopentenyl pyrophosphate + Geranyl diphosphate <> Farnesyl pyrophosphate + Pyrophosphate
Farnesyl pyrophosphate + Water + Heme > Heme O + Pyrophosphate
Farnesyl pyrophosphate + 5 Isopentenyl pyrophosphate <> Octaprenyl diphosphate +5 Pyrophosphate
Geranyl-PP + Isopentenyl pyrophosphate <> Pyrophosphate + Farnesyl pyrophosphate
Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate <> di-trans,poly-cis-Undecaprenyl diphosphate +8 Pyrophosphate + Undecaprenyl diphosphate
Heme + Water + Farnesyl pyrophosphate <> Heme O + Pyrophosphate
Geranyl-PP + Isopentenyl pyrophosphate > Farnesyl pyrophosphate + Pyrophosphate
Farnesyl pyrophosphate + Isopentenyl pyrophosphate > all-<i>trans</i>-octaprenyl diphosphate + Pyrophosphate
Farnesyl pyrophosphate + Isopentenyl pyrophosphate > Undecaprenyl diphosphate + Pyrophosphate
Farnesyl pyrophosphate + 5 Isopentenyl pyrophosphate >5 Pyrophosphate + Octaprenyl diphosphate
Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate >8 Pyrophosphate + di-trans,octa-cis-undecaprenyl diphosphate
ferroheme b + Water + Farnesyl pyrophosphate + Farnesyl pyrophosphate > Heme O + Pyrophosphate
Geranyl-PP + Isopentenyl pyrophosphate + Geranyl-PP + Isopentenyl pyrophosphate > Pyrophosphate + Farnesyl pyrophosphate + Farnesyl pyrophosphate
Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate + Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate >8 Pyrophosphate + di-trans,octa-cis-undecaprenyl diphosphate
Farnesyl pyrophosphate + 5 Isopentenyl pyrophosphate + Farnesyl pyrophosphate + 5 Isopentenyl pyrophosphate >5 Pyrophosphate + Octaprenyl diphosphate + Octaprenyl diphosphate
Farnesyl pyrophosphate + Water + Heme > Heme O + Pyrophosphate
Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate <> di-trans,octa-cis-undecaprenyl diphosphate +8 Pyrophosphate + Undecaprenyl diphosphate
Farnesyl pyrophosphate + 5 Isopentenyl pyrophosphate <> Octaprenyl diphosphate +5 Pyrophosphate
Farnesyl pyrophosphate + Water + Heme > Heme O + Pyrophosphate
Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate <> di-trans,octa-cis-undecaprenyl diphosphate +8 Pyrophosphate + Undecaprenyl diphosphate
SMPDB Pathways:
Porphyrin metabolismPW000936 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolites: Ubiquinol biosynthesisPW000981 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolites: Ubiquinol biosynthesis 2PW002036 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary metabolites: methylerythritol phosphate and polyisoprenoid biosynthesisPW000958 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
  • trans, trans-farnesyl diphosphate biosynthesis PWY-5123
  • di-trans,poly-cis-undecaprenyl phosphate biosynthesis PWY-5785
  • octaprenyl diphosphate biosynthesis PWY-5783
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-7943000000-ab6d749700f510a94133View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - n/a 26V, negativesplash10-014i-0090000000-09efa5f4e481376eae3dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-001i-2009000000-b2358e50ee86b2ebccb5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-004i-9004000000-b255d40b3beef0ddd16fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 16V, negativesplash10-004i-9001000000-64cd48aa93040d775977View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 19V, negativesplash10-004i-9000000000-84a4e8d938e03661128eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 25V, negativesplash10-004i-9000000000-eb2e768f7c19af669f74View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 26V, negativesplash10-03di-0209000000-651c59dc3e732ea880d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 26V, negativesplash10-0a4i-0900000000-ae4be9bde4ed56cfa99bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 26V, positivesplash10-0002-0294000000-7019f71a6e4f542dddaeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pc0-1469000000-e3fd27c0418d0977f84eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-6791000000-1ca128d2b96287a5b2f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0q29-9820000000-3277fbdf16e288ab1142View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0409000000-f8bbf786ee9d33cb48d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9501000000-8d060d3ceac94de45b8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a265a369e6802359a7dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-ea5bda9906940e9694b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2409000000-4b044bb59695723b85bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9600000000-a090357e0efeb6192936View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0019000000-66a0a5510c1d34aea230View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-114i-0394000000-89ab3170c9695823fb2fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05rs-6900000000-7b5163a81d3cbdf1feb4View in MoNA
References
References:
  • Argmann CA, Edwards JY, Sawyez CG, O'Neil CH, Hegele RA, Pickering JG, Huff MW: Regulation of macrophage cholesterol efflux through hydroxymethylglutaryl-CoA reductase inhibition: a role for RhoA in ABCA1-mediated cholesterol efflux. J Biol Chem. 2005 Jun 10;280(23):22212-21. Epub 2005 Apr 6. Pubmed: 15817453
  • Fukuchi J, Song C, Ko AL, Liao S: Transcriptional regulation of farnesyl pyrophosphate synthase by liver X receptors. Steroids. 2003 Sep;68(7-8):685-91. Pubmed: 12957674
  • 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
  • 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
  • Notarnicola M, Messa C, Cavallini A, Bifulco M, Tecce MF, Eletto D, Di Leo A, Montemurro S, Laezza C, Caruso MG: Higher farnesyl diphosphate synthase activity in human colorectal cancer inhibition of cellular apoptosis. Oncology. 2004;67(5-6):351-8. Pubmed: 15713990
  • Reigard SA, Zahn TJ, Haworth KB, Hicks KA, Fierke CA, Gibbs RA: Interplay of isoprenoid and peptide substrate specificity in protein farnesyltransferase. Biochemistry. 2005 Aug 23;44(33):11214-23. Pubmed: 16101305
  • Saisho Y, Morimoto A, Umeda T: Determination of farnesyl pyrophosphate in dog and human plasma by high-performance liquid chromatography with fluorescence detection. Anal Biochem. 1997 Oct 1;252(1):89-95. Pubmed: 9324945
  • Sanders JM, Song Y, Chan JM, Zhang Y, Jennings S, Kosztowski T, Odeh S, Flessner R, Schwerdtfeger C, Kotsikorou E, Meints GA, Gomez AO, Gonzalez-Pacanowska D, Raker AM, Wang H, van Beek ER, Papapoulos SE, Morita CT, Oldfield E: Pyridinium-1-yl bisphosphonates are potent inhibitors of farnesyl diphosphate synthase and bone resorption. J Med Chem. 2005 Apr 21;48(8):2957-63. Pubmed: 15828834
  • Shellman YG, Ribble D, Miller L, Gendall J, Vanbuskirk K, Kelly D, Norris DA, Dellavalle RP: Lovastatin-induced apoptosis in human melanoma cell lines. Melanoma Res. 2005 Apr;15(2):83-9. Pubmed: 15846140
  • Tacer KF, Haugen TB, Baltsen M, Debeljak N, Rozman D: Tissue-specific transcriptional regulation of the cholesterol biosynthetic pathway leads to accumulation of testis meiosis-activating sterol (T-MAS). J Lipid Res. 2002 Jan;43(1):82-9. Pubmed: 11792726
  • 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:Castillo-Bocanegra, Rafael. Synthesis and biological activity of farnesyl pyrophosphate analogs. (1977), 193 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID17407
HMDB IDHMDB00961
Pubchem Compound ID445713
Kegg IDC00448
ChemSpider ID393270
WikipediaFarnesyl pyrophosphate
BioCyc IDFARNESYL-PP
EcoCyc IDFARNESYL-PP
Ligand ExpoFPP

Enzymes

General function:
Involved in isoprenoid biosynthetic process
Specific function:
Geranyl diphosphate + isopentenyl diphosphate = diphosphate + trans,trans-farnesyl diphosphate
Gene Name:
ispA
Uniprot ID:
P22939
Molecular weight:
32159
Reactions
Geranyl diphosphate + isopentenyl diphosphate = diphosphate + (2E,6E)-farnesyl diphosphate.
General function:
Involved in transferase activity, transferring alkyl or aryl (other than methyl) groups
Specific function:
Generates undecaprenyl pyrophosphate (UPP) from isopentenyl pyrophosphate (IPP). UPP is the precursor of glycosyl carrier lipid in the biosynthesis of bacterial cell wall polysaccharide components such as peptidoglycan and lipopolysaccharide
Gene Name:
uppS
Uniprot ID:
P60472
Molecular weight:
28444
Reactions
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + di-trans,octa-cis-undecaprenyl diphosphate.
General function:
Involved in isoprenoid biosynthetic process
Specific function:
Supplies octaprenyl diphosphate, the precursor for the side chain of the isoprenoid quinones ubiquinone and menaquinone
Gene Name:
ispB
Uniprot ID:
P0AD57
Molecular weight:
35217
Reactions
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate = 5 diphosphate + all-trans-octaprenyl diphosphate.
General function:
Involved in protoheme IX farnesyltransferase activity
Specific function:
Converts heme B (protoheme IX) to heme O by substitution of the vinyl group on carbon 2 of heme B porphyrin ring with a hydroxyethyl farnesyl side group
Gene Name:
cyoE
Uniprot ID:
P0AEA5
Molecular weight:
32248