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Geranyl diphosphate (M2MDB003527)

Record Information
Version2.0
Creation Date2012-10-10 12:18:24 -0600
Update Date2015-09-16 14:50:11 -0600
Secondary Accession Numbers
  • ECMDB23137
Identification
Name:Geranyl diphosphate
DescriptionGeranyl diphosphate is regarded as a key intermediate in the steroid, isoprene and terpene biosynthesis pathways and is used in the biosynthesis of farnesyl pyrophosphate, geranylgeranyl pyrophosphate, cholesterol, terpenes and terpenoids. (wikipedia).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • ω,E-geranyl diphosphate
  • ω,e-geranyl diphosphoric acid
  • Geranyl diphosphoric acid
  • Geranyl pyrophosphate
  • Geranyl pyrophosphoric acid
  • Geranyl-diphosphate
  • Geranyl-diphosphoric acid
  • Geranyl-PP
  • Geranyl-pyrophosphate
  • Geranyl-pyrophosphoric acid
  • GPP
Chemical Formula:C40H68O7P2
Weight:Average: 722.9112
Monoisotopic: 722.444027554
InChI Key:CNCHONBZLLTYBW-NISPWTRESA-N
InChI:InChI=1S/C40H68O7P2/c1-33(2)17-13-21-37(9)25-29-43-48(41,44-30-26-38(10)22-14-18-34(3)4)47-49(42,45-31-27-39(11)23-15-19-35(5)6)46-32-28-40(12)24-16-20-36(7)8/h17-20,25-28H,13-16,21-24,29-32H2,1-12H3/b37-25+,38-26+,39-27+,40-28+
CAS number:763-10-0
IUPAC Name:bis(2E)-3,7-dimethylocta-2,6-dien-1-yl {[bis({[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy})phosphoryl]oxy}phosphonate
Traditional IUPAC Name:bis(2E)-3,7-dimethylocta-2,6-dien-1-yl {bis[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxyphosphoryl}oxyphosphonate
SMILES:[H]\C(COP(=O)(OC\C([H])=C(/C)CCC=C(C)C)OP(=O)(OC\C([H])=C(/C)CCC=C(C)C)OC\C([H])=C(/C)CCC=C(C)C)=C(\C)CCC=C(C)C
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
  • Dialkyl 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 DescriptorsNot Available
Physical Properties
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0005 g/LALOGPS
logP6.97ALOGPS
logP12.15ChemAxon
logS-6.2ALOGPS
pKa (Strongest Basic)-9.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area80.29 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity215.14 m³·mol⁻¹ChemAxon
Polarizability85.36 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
Geranyl-PP + Isopentenyl pyrophosphate + Geranyl diphosphate <> Farnesyl pyrophosphate + Pyrophosphate
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0901012500-d1b7aa18c9b2d51ff0c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3901010000-a9b86de7dae021885b86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ldr-9700002000-17516a4fadeccb729babView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000040900-3880e297b06dcbb047b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-008i-0300960100-a0493861d38f5bf740dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0082910000-4f9a62a28157471f4c2bView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17211
HMDB IDHMDB01285
Pubchem Compound ID445995
Kegg IDC00341
ChemSpider IDNot Available
WikipediaGeranyl pyrophosphate
BioCyc IDGERANYL-PP
EcoCyc IDGERANYL-PP

Enzymes

Protein Details
1. Geranyltranstransferase
General function:
Involved in isoprenoid biosynthetic process
Specific function:
Geranyl diphosphate + isopentenyl diphosphate = diphosphate + trans,trans-farnesyl diphosphate
Gene Name:
ispA
Uniprot ID:
P22939
Molecular weight:
32159
Reactions
Geranyl diphosphate + isopentenyl diphosphate = diphosphate + (2E,6E)-farnesyl diphosphate.