Geranyl diphosphate (CHEM023750)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:16:20 UTC
Update Date2016-11-09 01:17:46 UTC
Accession NumberCHEM023750
Identification
Common NameGeranyl diphosphate
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Geranyl pyrophosphateChEBI
PolyisopentenylpyrophosphateKegg
PolyisopentenyldiphosphateKegg
trans-PolyisopentenyldiphosphateKegg
Polyprenyl diphosphateKegg
Geranyl pyrophosphoric acidGenerator
Polyisopentenylpyrophosphoric acidGenerator
Polyisopentenyldiphosphoric acidGenerator
trans-Polyisopentenyldiphosphoric acidGenerator
Polyprenyl diphosphoric acidGenerator
(2E)-3,7-Dimethylocta-2,6-dien-1-yl trihydrogen diphosphateHMDB
Geranyl diphosphateHMDB
Geranyl-diphosphateHMDB
Geranyl-pyrophosphateHMDB
Monoterpenyl diphosphateHMDB
Neryl diphosphateHMDB
trans-Geranyl pyrophosphateHMDB
P-[(2E)-3,7-Dimethyl-2,6-octadien-1-yl]diphosphoric acidHMDB
trans-geranyl-PPHMDB
Chemical FormulaC10H20O7P2
Average Molecular Mass314.209 g/mol
Monoisotopic Mass314.068 g/mol
CAS Registry Number763-10-0
IUPAC Name[({[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid
Traditional Namegeranyl diphosphate
SMILESCC(C)=CCC\C(C)=C\CO[P@@](=O)(O)OP(=O)(O)O
InChI IdentifierInChI=1S/C10H20O7P2/c1-9(2)5-4-6-10(3)7-8-16-19(14,15)17-18(11,12)13/h5,7H,4,6,8H2,1-3H3,(H,14,15)(H2,11,12,13)/b10-7+
InChI KeyGVVPGTZRZFNKDS-JXMROGBWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as isoprenoid phosphates. These are prenol lipids containing a phosphate group linked to an isoprene (2-methylbuta-1,3-diene) unit.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassIsoprenoid phosphates
Direct ParentIsoprenoid phosphates
Alternative Parents
Substituents
  • Organic pyrophosphate
  • Monoterpenoid
  • Isoprenoid phosphate
  • Acyclic monoterpenoid
  • 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 Solubility0.9 g/LALOGPS
logP1.63ALOGPS
logP1.96ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity72.93 m³·mol⁻¹ChemAxon
Polarizability28.52 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-9640000000-9ce32c835bdcfa97fa15Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-0002-0090000000-b5ca864b0ba8818ad627Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-0002-0090000000-c7f7c5c529a56d532304Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-0002-3390000000-010bee66d1e4bd685e95Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-004i-9440000000-13e525f66230aae586a2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 17V, negativesplash10-004i-9200000000-a9da8f03edb73eec50bfSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 20V, negativesplash10-004i-9100000000-fe3060700600ee72f8ddSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 23V, negativesplash10-004i-9000000000-15de26c097afd86b7007Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 27V, negativesplash10-004i-9000000000-bcc45bf0bf3bbb46af13Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 33V, negativesplash10-004i-9000000000-b8b56dc9ea06c2ce52b5Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-0a4i-0900000000-f2685d197409ed952f02Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-004i-9000000000-5ef060d5ec4b80c35c1aSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-0a4i-0900000000-60b9e910670cbc6ebe0cSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-0bt9-0390000000-6532032bbb594aa54d9cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-03di-0009000000-3bcab8c3688c96a4cec5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, negativesplash10-03di-2009000000-42fa98db20ae4d6f687eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-01t9-9005000000-44618200345aed481b48Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 12V, negativesplash10-004i-9000000000-befed7a961a777eb5f66Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 15V, negativesplash10-004i-9000000000-8afaaf750b51acbd1a01Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 18V, negativesplash10-004i-9000000000-b5b3b346fecad6ae473dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-1953000000-e5ee3340554c9ecac23eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-5910000000-82bcd2195a53b847981cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gc0-9400000000-f87d391f1b3c01743515Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0509000000-43083a162145718cd977Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9500000000-053b6323e620a16328a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4faed4c921d605619cafSpectrum
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 IDDB02552
HMDB IDHMDB0001285
FooDB IDFDB001463
Phenol Explorer IDNot Available
KNApSAcK IDC00000846
BiGG ID34712
BioCyc IDGERANYL-PP
METLIN ID6134
PDB IDNot Available
Wikipedia LinkGeranyl_pyrophosphate
Chemspider ID393471
ChEBI ID17211
PubChem Compound ID445995
Kegg Compound IDC05847
YMDB IDYMDB00266
ECMDB IDECMDB01285
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Runquist M; Ericsson J; Thelin A; Chojnacki T; Dallner G Biosynthesis of trans,trans,trans-geranylgeranyl diphosphate by the cytosolic fraction from rat tissues. Biochemical and biophysical research communications (1992), 186(1), 157-65.
2. Micali E, Chehade KA, Isaacs RJ, Andres DA, Spielmann HP: Protein farnesyltransferase isoprenoid substrate discrimination is dependent on isoprene double bonds and branched methyl groups. Biochemistry. 2001 Oct 16;40(41):12254-65.
3. Kavanagh KL, Guo K, Dunford JE, Wu X, Knapp S, Ebetino FH, Rogers MJ, Russell RG, Oppermann U: The molecular mechanism of nitrogen-containing bisphosphonates as antiosteoporosis drugs. Proc Natl Acad Sci U S A. 2006 May 16;103(20):7829-34. Epub 2006 May 9.
4. Holstein SA, Hohl RJ: Isoprenoids: remarkable diversity of form and function. Lipids. 2004 Apr;39(4):293-309.
5. Gan X, Kaplan R, Menke JG, MacNaul K, Chen Y, Sparrow CP, Zhou G, Wright SD, Cai TQ: Dual mechanisms of ABCA1 regulation by geranylgeranyl pyrophosphate. J Biol Chem. 2001 Dec 28;276(52):48702-8. Epub 2001 Oct 18.
6. Sagami H, Ogura K: [A new development in isoprenoid biochemistry brought by the discovery of prenylated proteins]. Seikagaku. 1994 Dec;66(12):1488-501.
7. Loza-Tavera H: Monoterpenes in essential oils. Biosynthesis and properties. Adv Exp Med Biol. 1999;464:49-62.
8. Barnard GF, Popjak G: Human liver prenyltransferase and its characterization. Biochim Biophys Acta. 1981 Sep 15;661(1):87-99.
9. Pont F, Luciani B, Belmant C, Fournie JJ: Characterization of phosphoantigens by high-performance anion-exchange chromatography-electrospray ionization ion trap mass spectrometry and nanoelectrospray ionization ion trap mass spectrometry. Anal Chem. 2001 Aug 1;73(15):3562-9.
10. Smit A, Mushegian A: Biosynthesis of isoprenoids via mevalonate in Archaea: the lost pathway. Genome Res. 2000 Oct;10(10):1468-84.
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=19049370
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=19856009
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23607888
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=7753173