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Human Metabolome Database Version 3.5

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Showing metabocard for Farnesyl pyrophosphate (HMDB00961)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:40 -0700
HMDB ID HMDB00961
Secondary Accession Numbers
  • HMDB04201
Metabolite Identification
Common Name Farnesyl pyrophosphate
Description Farnesyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. -- Wikipedia.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C15H28O7P2
Average Molecular Weight 382.3261
Monoisotopic Molecular Weight 382.131026274
IUPAC Name {[hydroxy({[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy})phosphoryl]oxy}phosphonic acid
Traditional IUPAC Name {hydroxy[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxyphosphoryl}oxyphosphonic acid
CAS Registry Number 13058-04-3
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 Key VWFJDQUYCIWHTN-YFVJMOTDSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Prenol Lipids
Sub Class Sesquiterpenes
Other Descriptors
  • Aliphatic Acyclic Compounds
  • farnesyl phosphate(ChEBI)
  • polyprenol diphosphate(ChEBI)
Substituents
  • Acyclic Alkene
  • Isoprene
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Phosphoric Acid Ester
Direct Parent Sesquiterpenes
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.081 g/L ALOGPS
LogP 2.40 ALOGPS
LogP 3.62 ChemAxon
LogS -3.68 ALOGPS
pKa (strongest acidic) 1.77 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 113.29 A2 ChemAxon
Rotatable Bond Count 11 ChemAxon
Refractivity 96.73 ChemAxon
Polarizability 37.94 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
  • Peroxisome
Biofluid Locations
  • Blood
Tissue Location
  • Neuron
  • Testes
Pathways
Name SMPDB Link KEGG Link
Porphyrin Metabolism SMP00024 map00860 Link_out
Steroid Biosynthesis SMP00023 map00100 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.0086 (0.0000-0.0170) uM Adult (>18 years old) Not Specified Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022339
KNApSAcK ID Not Available
Chemspider ID 393270 Link_out
KEGG Compound ID C00448 Link_out
BioCyc ID FARNESYL-PP Link_out
BiGG ID 35006 Link_out
Wikipedia Link Farnesyl pyrophosphate Link_out
NuGOwiki Link HMDB00961 Link_out
Metagene Link HMDB00961 Link_out
METLIN ID 403 Link_out
PubChem Compound 445713 Link_out
PDB ID FPP Link_out
ChEBI ID 17407 Link_out
References
Synthesis Reference Castillo-Bocanegra, Rafael. Synthesis and biological activity of farnesyl pyrophosphate analogs. (1977), 193 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. 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 Link_out
  2. 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 Link_out
  3. 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 Link_out
  4. 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 Link_out
  5. 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 Link_out
  6. 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 Link_out
  7. 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 Link_out
  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. Pubmed: 12957674 Link_out
Enzymes
Name: Squalene synthase
Reactions:
  • (1) (1a) 2 farnesyl diphosphate = diphosphate + presqualene diphosphate [RN:R00702]
  • (2) (1b) presqualene diphosphate + NAD(P)H + H+ = squalene + diphosphate + NAD(P)+ [RN:R02872]
Gene Name: FDFT1
Uniprot ID: P37268 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Geranylgeranyl pyrophosphate synthase
Reactions:
  • trans,trans-farnesyl diphosphate + isopentenyl diphosphate = diphosphate + geranylgeranyl diphosphate [RN:R02061]
Gene Name: GGPS1
Uniprot ID: O95749 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Farnesyl pyrophosphate synthase
Reactions:
  • geranyl diphosphate + isopentenyl diphosphate = diphosphate + trans,trans-farnesyl diphosphate [RN:R02003]
Gene Name: FDPS
Uniprot ID: P14324 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha
Reactions:
  • geranylgeranyl diphosphate + protein-cysteine = S-geranylgeranyl-protein + diphosphate
Gene Name: FNTA
Uniprot ID: P49354 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protein farnesyltransferase subunit beta
Reactions:
  • farnesyl diphosphate + protein-cysteine = S-farnesyl protein + diphosphate
Gene Name: FNTB
Uniprot ID: P49356 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA