(2E,6E)-farnesyl diphosphate (PAMDB110355)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110355
Identification
Name: (2E,6E)-farnesyl diphosphate
Description:An organophosphate oxoanion that is the trianion obtained by removal of the three protons from the diphosphate group of 2-trans,6-trans-farnesyl diphosphate.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2-trans,6-trans-farnesyl diphosphate
  • 2-trans,6-trans-farnesyl diphosphate
  • FPP
  • trans
  • trans-farnesyl diphosphate
  • farnesyl-PP
  • farnesyl pyrophosphate
  • ω,E,E-farnesyl diphosphate
  • farnesyl diphosphate
  • (E,E)-farnesyl diphosphate
  • all-trans-farnesyl diphosphate
Chemical Formula: C15H25O7P2
Average Molecular Weight: 379.31
Monoisotopic Molecular Weight: 382.1310262735
InChI Key: VWFJDQUYCIWHTN-YFVJMOTDSA-K
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)/p-3/b14-9+,15-11+
CAS number: 13058-04-3
IUPAC Name:(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl diphosphate
Traditional IUPAC Name: [hydroxy([(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy)phosphoryl]oxyphosphonic acid
SMILES:CC(=CCCC(=CCCC(=CCOP(OP([O-])(=O)[O-])(=O)[O-])C)C)C
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Lipids and lipid-like molecules
Sub ClassPrenol lipids
Direct Parent Sesquiterpenoids
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 Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-3
Melting point: Not Available
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
Biological Properties
Cellular Locations: Not Available
Reactions:
ferroheme b + (2E,6E)-farnesyl diphosphate + Water → HEME_O + diphosphate
(2E,6E)-farnesyl diphosphate + isopentenyl diphosphate → all-trans-octaprenyl diphosphate + diphosphate
(2E,6E)-farnesyl diphosphate + isopentenyl diphosphate → di-trans,octa-cis-undecaprenyl diphosphate + diphosphate
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
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
References
References:
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
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
CAS13058-04-3
ChEBI175763
ChemSpider11633047
HMDBHMDB00961
IAF126035006
KEGGC00448
KNApSAcKC00007268
MetaboLightsMTBLC175763
PubChem15983959