Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB003527
Identification
Name: Geranyl diphosphate
Description:Geranyl 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
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
Average Molecular Weight: 722.9112
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Prenol lipids
Sub ClassIsoprenoid phosphates
Direct Parent Isoprenoid phosphates
Alternative Parents
Substituents
  • Organic pyrophosphate
  • Monoterpenoid
  • Isoprenoid phosphate
  • Acyclic monoterpenoid
  • Dialkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0005 mg/mLALOGPS
logP6.97ALOGPS
logP12.15ChemAxon
logS-6.2ALOGPS
pKa (Strongest Basic)-9.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area80.29 Å2ChemAxon
Rotatable Bond Count26ChemAxon
Refractivity215.14 m3·mol-1ChemAxon
Polarizability85.36 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
Pathways:
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
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 ID20016346
WikipediaGeranyl pyrophosphate
BioCyc IDGERANYL-PP
EcoCyc IDGERANYL-PP