Identification
YMDB IDYMDB00325
Name2-trans,6-trans-farnesyl diphosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionFarnesyl pyrophosphate, also known as farnesyl diphosphoric acid or farnesyl-PP, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Farnesyl pyrophosphate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
  • (2E,6E)-farnesol diphosphate
  • (2E,6E)-Farnesyl diphosphate
  • (2E,6E)-Farnesyl pyrophosphate
  • (all-E)-Farnesyl diphosphate
  • (E,E)-Farnesyl diphosphate
  • (E,E)-Farnesyl pyrophosphate
  • 2-trans,6-trans-Farnesyl diphosphate
  • 2-trans,6-trans-Farnesyl pyrophosphate
  • all-trans-farnesyl diphosphate
  • all-trans-Farnesyl pyrophosphate
  • Farnesyl diphosphate
  • Farnesyl pyrophosphate
  • Farnesyl pyrophosphic acid
  • Farnesyl-PP
  • FPP
  • fpp, farnesyl pyrophosphate
  • omega,E,E-farnesyl diphosphate
  • trans-Farnesyl pyrophosphate
  • trans-trans-Farnesyl diphosphate
  • trans-trans-Farnesyl pyrophosphate
  • trans, trans-farnesyl diphosphate
  • trans,trans-farnesyl diphosphate
  • (2E,6E)-Farnesol diphosphoric acid
  • (2E,6E)-Farnesyl diphosphoric acid
  • (2E,6E)-Farnesyl pyrophosphoric acid
  • (all-e)-Farnesyl diphosphoric acid
  • (e,e)-Farnesyl pyrophosphoric acid
  • 2-trans,6-trans-Farnesyl pyrophosphoric acid
  • all-trans-Farnesyl pyrophosphoric acid
  • Farnesyl diphosphoric acid
  • trans,trans-Farnesyl diphosphoric acid
  • trans-trans-Farnesyl diphosphoric acid
  • 2-trans,6-trans-Farnesyl diphosphoric acid
  • Farnesyl pyrophosphoric acid
  • Farnesyl pyrophosphate, (e,e)-isomer
  • Farnesyl pyrophosphate, (e,Z)-isomer
  • Farnesyl pyrophosphate, (Z,e)-isomer
  • Farnesyl pyrophosphate, (Z,Z)-isomer
  • Farnesylpyrophosphate
CAS number13058-04-3
WeightAverage: 382.3261
Monoisotopic: 382.131026274
InChI KeyVWFJDQUYCIWHTN-YFVJMOTDSA-N
InChIInChI=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+
IUPAC Name{[hydroxy({[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy})phosphoryl]oxy}phosphonic acid
Traditional IUPAC Namefarnesyl diphosphate
Chemical FormulaC15H28O7P2
SMILESCC(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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
  • mitochondrion
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Cholesterol biosynthesis and metabolism CE(10:0)PW002545 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(12:0)PW002548 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(14:0)PW002544 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(16:0)PW002550 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(18:0)PW002551 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Steroid biosynthesisec00100 Map00100
Terpenoid backbone biosynthesisec00900 Map00900
SMPDB ReactionsNot Available
KEGG Reactions
2-trans,6-trans-farnesyl diphosphate + Isopentenyl pyrophosphatePyrophosphate + 2-trans,6-trans,10-trans-geranylgeranyl diphosphate
Isopentenyl pyrophosphate + Geranyl-PPPyrophosphate + 2-trans,6-trans-farnesyl diphosphate
water + Heme + 2-trans,6-trans-farnesyl diphosphatePyrophosphate + heme o
2-trans,6-trans-farnesyl diphosphate + NADPH + hydronNADP + squalene + Pyrophosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-7943000000-ab6d749700f510a94133JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - n/a 26V, negativesplash10-014i-0090000000-09efa5f4e481376eae3dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-001i-2009000000-b2358e50ee86b2ebccb5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-004i-9004000000-b255d40b3beef0ddd16fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 16V, negativesplash10-004i-9001000000-64cd48aa93040d775977JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 19V, negativesplash10-004i-9000000000-84a4e8d938e03661128eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 25V, negativesplash10-004i-9000000000-eb2e768f7c19af669f74JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 26V, negativesplash10-03di-0209000000-651c59dc3e732ea880d7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 26V, negativesplash10-0a4i-0900000000-ae4be9bde4ed56cfa99bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 26V, positivesplash10-0002-0294000000-7019f71a6e4f542dddaeJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pc0-1469000000-e3fd27c0418d0977f84eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-6791000000-1ca128d2b96287a5b2f1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0q29-9820000000-3277fbdf16e288ab1142JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0409000000-f8bbf786ee9d33cb48d4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9501000000-8d060d3ceac94de45b8dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a265a369e6802359a7dfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-ea5bda9906940e9694b2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2409000000-4b044bb59695723b85bdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9600000000-a090357e0efeb6192936JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0019000000-66a0a5510c1d34aea230JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-114i-0394000000-89ab3170c9695823fb2fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05rs-6900000000-7b5163a81d3cbdf1feb4JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17407
HMDB IDHMDB00961
Pubchem Compound ID445713
Kegg IDC00448
ChemSpider ID23092868
FOODB IDFDB022339
WikipediaFarnesyl pyrophosphate
BioCyc IDFARNESYL-PP

Enzymes

General function:
Involved in isoprenoid biosynthetic process
Specific function:
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:
ERG20
Uniprot ID:
P08524
Molecular weight:
40483.0
Reactions
Dimethylallyl diphosphate + isopentenyl diphosphate → diphosphate + geranyl diphosphate.
Geranyl diphosphate + isopentenyl diphosphate → diphosphate + (2E,6E)-farnesyl diphosphate.
General function:
Involved in isoprenoid biosynthetic process
Specific function:
Catalyzes the trans-addition of the 3 molecules of IPP onto DMAPP to form geranylgeranyl pyrophosphate. Required for the membrane attachment of YPT1 and SEC4. May be involved in vesicle trafficking and protein sorting
Gene Name:
BTS1
Uniprot ID:
Q12051
Molecular weight:
38651.0
Reactions
Dimethylallyl diphosphate + isopentenyl diphosphate → diphosphate + geranyl diphosphate.
Geranyl diphosphate + isopentenyl diphosphate → diphosphate + (2E,6E)-farnesyl diphosphate.
Trans,trans-farnesyl diphosphate + isopentenyl diphosphate → diphosphate + geranylgeranyl diphosphate.
General function:
Involved in transferase activity
Specific function:
May regulate the flux of isoprene intermediates through the sterol pathway. Squalene synthase is crucial for balancing the incorporation of farnesyl diphosphate (FPP) into sterol and nonsterol isoprene synthesis. ERG9 is also essential for cell growth in yeast
Gene Name:
ERG9
Uniprot ID:
P29704
Molecular weight:
51719.39844
Reactions
2 farnesyl diphosphate → diphosphate + presqualene diphosphate.
Presqualene diphosphate + NAD(P)H → squalene + diphosphate + NAD(P)(+).
General function:
Involved in protoheme IX farnesyltransferase activity
Specific function:
Converts protoheme IX and farnesyl diphosphate to heme O
Gene Name:
COX10
Uniprot ID:
P21592
Molecular weight:
52147.19922
Reactions