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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2015-12-02 05:10:07 UTC
HMDB IDHMDB00961
Secondary Accession Numbers
  • HMDB04201
Metabolite Identification
Common NameFarnesyl 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
  1. (2E,6E)-Farnesyl diphosphate
  2. (2E,6E)-Farnesyl pyrophosphate
  3. (all-E)-Farnesyl diphosphate
  4. (E,E)-Farnesyl diphosphate
  5. (E,E)-Farnesyl pyrophosphate
  6. 2-trans,6-trans-Farnesyl diphosphate
  7. 2-trans,6-trans-Farnesyl pyrophosphate
  8. All-trans-Farnesyl pyrophosphate
  9. Farnesyl diphosphate
  10. Farnesyl pyrophosphate
  11. Farnesyl-PP
  12. trans-Farnesyl pyrophosphate
  13. trans-trans-Farnesyl diphosphate
  14. trans-trans-Farnesyl pyrophosphate
Chemical FormulaC15H28O7P2
Average Molecular Weight382.3261
Monoisotopic Molecular Weight382.131026274
IUPAC Name{[hydroxy({[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy})phosphoryl]oxy}phosphonic acid
Traditional Namefarnesyl diphosphate
CAS Registry Number13058-04-3
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O
InChI Identifier
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+
InChI KeyInChIKey=VWFJDQUYCIWHTN-YFVJMOTDSA-N
Chemical Taxonomy
DescriptionThis compound 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 phosphate
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Component of Terpenoid biosynthesis
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
  • Peroxisome
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 Solubility0.081 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity96.73 m3·mol-1ChemAxon
Polarizability37.94 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-4jqz000000-e3fd27c0418d0977f84eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-nuz4000000-1ca128d2b96287a5b2f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-zx92000000-3277fbdf16e288ab1142View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-1h1z000000-f8bbf786ee9d33cb48d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-zk25000000-8d060d3ceac94de45b8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-z300000000-a265a369e6802359a7dfView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
  • Peroxisome
Biofluid Locations
  • Blood
Tissue Location
  • Neuron
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Acute Intermittent PorphyriaSMP00344Not Available
Alendronate pathwaySMP00095Not Available
Atorvastatin PathwaySMP00131Not Available
Cerivastatin PathwaySMP00111Not Available
CHILD SyndromeSMP00387Not Available
Cholesteryl ester storage diseaseSMP00508Not Available
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)SMP00388Not Available
Congenital Erythropoietic Porphyria (CEP) or Gunther DiseaseSMP00345Not Available
DesmosterolosisSMP00386Not Available
Fluvastatin PathwaySMP00119Not Available
Hereditary Coproporphyria (HCP)SMP00342Not Available
Hyper-IgD syndromeSMP00509Not Available
HypercholesterolemiaSMP00209Not Available
Ibandronate PathwaySMP00079Not Available
Lovastatin PathwaySMP00099Not Available
Lysosomal Acid Lipase Deficiency (Wolman Disease)SMP00319Not Available
Mevalonic aciduriaSMP00510Not Available
Pamidronate PathwaySMP00117Not Available
Porphyria Variegata (PV)SMP00346Not Available
Porphyrin MetabolismSMP00024map00860
Pravastatin PathwaySMP00089Not Available
Risedronate PathwaySMP00112Not Available
Rosuvastatin PathwaySMP00092Not Available
Simvastatin Action PathwaySMP00082Not Available
Smith-Lemli-Opitz Syndrome (SLOS)SMP00389Not Available
Steroid BiosynthesisSMP00023map00100
Wolman diseaseSMP00511Not Available
Zoledronate PathwaySMP00107Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0086 (0.0000-0.0170) uMAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022339
KNApSAcK IDNot Available
Chemspider ID393270
KEGG Compound IDC00448
BioCyc IDFARNESYL-PP
BiGG ID35006
Wikipedia LinkFarnesyl pyrophosphate
NuGOwiki LinkHMDB00961
Metagene LinkHMDB00961
METLIN ID403
PubChem Compound445713
PDB IDFPP
ChEBI ID17407
References
Synthesis ReferenceCastillo-Bocanegra, Rafael. Synthesis and biological activity of farnesyl pyrophosphate analogs. (1977), 193 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [15713990 ]
  2. 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. [15846140 ]
  3. 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. [15817453 ]
  4. 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. [16101305 ]
  5. 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. [11792726 ]
  6. 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. [9324945 ]
  7. 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. [15828834 ]
  8. 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. [12957674 ]

Enzymes

General function:
Involved in transferase activity
Specific function:
Not Available
Gene Name:
FDFT1
Uniprot ID:
P37268
Molecular weight:
48114.87
Reactions
Farnesyl pyrophosphate + NAD(P)H → Squalene + Pyrophosphate + NAD(P)(+)details
Farnesyl pyrophosphate → Pyrophosphate + Presqualene diphosphatedetails
Farnesyl pyrophosphate + NADPH + Hydrogen Ion → Squalene + Pyrophosphate + NADPdetails
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
Geranyl-PP + Isopentenyl pyrophosphate → Pyrophosphate + Farnesyl pyrophosphatedetails
Farnesyl pyrophosphate + Isopentenyl pyrophosphate → Pyrophosphate + Geranylgeranyl-PPdetails
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
Geranyl-PP + Isopentenyl pyrophosphate → Pyrophosphate + Farnesyl pyrophosphatedetails
General function:
Involved in protoheme IX farnesyltransferase activity
Specific function:
Converts protoheme IX and farnesyl diphosphate to heme O (By similarity).
Gene Name:
COX10
Uniprot ID:
Q12887
Molecular weight:
Not Available
Reactions
Heme + Water + Farnesyl pyrophosphate → Heme O + 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
Farnesyl pyrophosphate + protein-cysteine → S-farnesyl protein + Pyrophosphatedetails
Farnesyl pyrophosphate + Protein-cysteine → S-Farnesyl protein + Pyrophosphatedetails
General function:
Involved in transferase activity, transferring alkyl or aryl (other than methyl) groups
Specific function:
Catalyzes cis-prenyl chain elongation to produce the polyprenyl backbone of dolichol, a glycosyl carrier-lipid required for the biosynthesis of several classes of glycoprotein.
Gene Name:
DHDDS
Uniprot ID:
Q86SQ9
Molecular weight:
Not Available
Reactions
Farnesyl pyrophosphate + → Dehydrodolichol diphosphate + details
General function:
Involved in catalytic activity
Specific function:
Catalyzes the transfer of a farnesyl moiety from farnesyl pyrophosphate to a cysteine at the fourth position from the C-terminus of several proteins. The beta subunit is responsible for peptide-binding.
Gene Name:
FNTB
Uniprot ID:
P49356
Molecular weight:
48773.2
Reactions
Farnesyl pyrophosphate + protein-cysteine → S-farnesyl protein + Pyrophosphatedetails
Farnesyl pyrophosphate + Protein-cysteine → S-Farnesyl protein + Pyrophosphatedetails
General function:
Not Available
Specific function:
Supplies decaprenyl diphosphate, the precursor for the side chain of the isoprenoid quinones ubiquinone-10.
Gene Name:
PDSS2
Uniprot ID:
Q86YH6
Molecular weight:
44128.17
Reactions
Farnesyl pyrophosphate + Isopentenyl pyrophosphate → Pyrophosphate + all-trans-Decaprenyl diphosphatedetails
General function:
Not Available
Specific function:
Supplies decaprenyl diphosphate, the precursor for the side chain of the isoprenoid quinones ubiquinone-10.
Gene Name:
PDSS1
Uniprot ID:
Q5T2R2
Molecular weight:
46260.6
Reactions
Farnesyl pyrophosphate + Isopentenyl pyrophosphate → Pyrophosphate + all-trans-Decaprenyl diphosphatedetails