Farnesyl pyrophosphate (CHEM035007)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:24:49 UTC
Update Date2016-11-09 01:21:13 UTC
Accession NumberCHEM035007
Identification
Common NameFarnesyl pyrophosphate
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2E,6E)-Farnesol diphosphateChEBI
(2E,6E)-Farnesyl diphosphateChEBI
(2E,6E)-Farnesyl pyrophosphateChEBI
(all-e)-Farnesyl diphosphateChEBI
(e,e)-Farnesyl pyrophosphateChEBI
2-trans,6-trans-Farnesyl pyrophosphateChEBI
all-trans-Farnesyl pyrophosphateChEBI
Farnesyl diphosphateChEBI
trans,trans-Farnesyl diphosphateChEBI
trans-trans-Farnesyl diphosphateChEBI
2-trans,6-trans-Farnesyl diphosphateKegg
(2E,6E)-Farnesol diphosphoric acidGenerator
(2E,6E)-Farnesyl diphosphoric acidGenerator
(2E,6E)-Farnesyl pyrophosphoric acidGenerator
(all-e)-Farnesyl diphosphoric acidGenerator
(e,e)-Farnesyl pyrophosphoric acidGenerator
2-trans,6-trans-Farnesyl pyrophosphoric acidGenerator
all-trans-Farnesyl pyrophosphoric acidGenerator
Farnesyl diphosphoric acidGenerator
trans,trans-Farnesyl diphosphoric acidGenerator
trans-trans-Farnesyl diphosphoric acidGenerator
2-trans,6-trans-Farnesyl diphosphoric acidGenerator
Farnesyl pyrophosphoric acidGenerator
(e,e)-Farnesyl diphosphateHMDB
Farnesyl-PPHMDB
trans-Farnesyl pyrophosphateHMDB
trans-trans-Farnesyl pyrophosphateHMDB
Farnesyl pyrophosphate, (e,e)-isomerHMDB
Farnesyl pyrophosphate, (e,Z)-isomerHMDB
Farnesyl pyrophosphate, (Z,e)-isomerHMDB
Farnesyl pyrophosphate, (Z,Z)-isomerHMDB
FarnesylpyrophosphateHMDB
Chemical FormulaC15H28O7P2
Average Molecular Mass382.330 g/mol
Monoisotopic Mass382.131 g/mol
CAS Registry Number372-97-4
IUPAC Name{[hydroxy({[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy})phosphoryl]oxy}phosphonic acid
Traditional Namefarnesyl diphosphate
SMILES[H]OP(=O)(O[H])OP(=O)(O[H])OC\C=C(/C)CC\C=C(/C)CCC=C(C)C
InChI IdentifierInChI=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 KeyVWFJDQUYCIWHTN-YFVJMOTDSA-N
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-7943000000-ab6d749700f510a94133Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 26V, negativesplash10-014i-0090000000-09efa5f4e481376eae3dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-001i-2009000000-b2358e50ee86b2ebccb5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-004i-9004000000-b255d40b3beef0ddd16fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 16V, negativesplash10-004i-9001000000-64cd48aa93040d775977Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 19V, negativesplash10-004i-9000000000-84a4e8d938e03661128eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 25V, negativesplash10-004i-9000000000-eb2e768f7c19af669f74Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 26V, negativesplash10-03di-0209000000-651c59dc3e732ea880d7Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 26V, negativesplash10-0a4i-0900000000-ae4be9bde4ed56cfa99bSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 26V, positivesplash10-0002-0294000000-7019f71a6e4f542dddaeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pc0-1469000000-e3fd27c0418d0977f84eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-6791000000-1ca128d2b96287a5b2f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0q29-9820000000-3277fbdf16e288ab1142Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0409000000-f8bbf786ee9d33cb48d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9501000000-8d060d3ceac94de45b8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a265a369e6802359a7dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-ea5bda9906940e9694b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2409000000-4b044bb59695723b85bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9600000000-a090357e0efeb6192936Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0019000000-66a0a5510c1d34aea230Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-114i-0394000000-89ab3170c9695823fb2fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05rs-6900000000-7b5163a81d3cbdf1feb4Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB07780
HMDB IDHMDB0000961
FooDB IDFDB022339
Phenol Explorer IDNot Available
KNApSAcK IDC00007268
BiGG ID35006
BioCyc IDFARNESYL-PP
METLIN ID403
PDB IDNot Available
Wikipedia LinkFarnesyl pyrophosphate
Chemspider ID393270
ChEBI ID17407
PubChem Compound ID445713
Kegg Compound IDC00448
YMDB IDYMDB00229
ECMDB IDECMDB00961
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Castillo-Bocanegra, Rafael. Synthesis and biological activity of farnesyl pyrophosphate analogs. University of California, San Francisco., 1977 - Farnesol  p.364
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.
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.
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.
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.
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.
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.
8. 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.
9. 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.
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=7753173