Showing Compound Card for Geranyl-PP (CDB005223)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (3) Show 5 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:21:41 UTC
Updated at2020-12-07 19:11:47 UTC
CannabisDB IDCDB005223
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameGeranyl-PP
DescriptionGeranyl-PP, also known as neryl diphosphate, 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. Thus, geranyl-PP is considered to be an isoprenoid lipid molecule. Geranyl-PP is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Geranyl-PP is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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 Weight314.21
Monoisotopic Molecular Weight314.0684
IUPAC Name[({[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid
Traditional Namegeranyl diphosphate
CAS Registry Number763-10-0
SMILES
CC(C)=CCC\C(C)=C\CO[P@](O)(=O)OP(O)(O)=O
InChI Identifier
InChI=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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSGeranyl-PP, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004j-9640000000-9ce32c835bdcfa97fa15Spectrum
Predicted GC-MSGeranyl-PP, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGeranyl-PP, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-0002-0090000000-b5ca864b0ba8818ad6272020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-0002-0090000000-c7f7c5c529a56d5323042020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-0002-3390000000-010bee66d1e4bd685e952020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-004i-9440000000-13e525f66230aae586a22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 17V, negativesplash10-004i-9200000000-a9da8f03edb73eec50bf2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 20V, negativesplash10-004i-9100000000-fe3060700600ee72f8dd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 23V, negativesplash10-004i-9000000000-15de26c097afd86b70072020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 27V, negativesplash10-004i-9000000000-bcc45bf0bf3bbb46af132020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 33V, negativesplash10-004i-9000000000-b8b56dc9ea06c2ce52b52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-0a4i-0900000000-f2685d197409ed952f022020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-004i-9000000000-5ef060d5ec4b80c35c1a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-0a4i-0900000000-60b9e910670cbc6ebe0c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-0bt9-0390000000-6532032bbb594aa54d9c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-03di-0009000000-3bcab8c3688c96a4cec52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, negativesplash10-03di-2009000000-42fa98db20ae4d6f687e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-01t9-9005000000-44618200345aed481b482020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, negativesplash10-004i-9000000000-befed7a961a777eb5f662020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 15V, negativesplash10-004i-9000000000-8afaaf750b51acbd1a012020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 18V, negativesplash10-004i-9000000000-b5b3b346fecad6ae473d2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-1953000000-e5ee3340554c9ecac23e2015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-5910000000-82bcd2195a53b847981c2015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gc0-9400000000-f87d391f1b3c017435152015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0509000000-43083a162145718cd9772015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9500000000-053b6323e620a16328a82015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4faed4c921d605619caf2015-09-15View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Geranylgeranyl pyrophosphate synthaseGGPS11q43O95749 details
Farnesyl pyrophosphate synthaseFDPS1q22P14324 details
4-hydroxybenzoate polyprenyltransferase, mitochondrialCOQ24q21.23Q96H96 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Geranylgeranyl pyrophosphate synthaseGGPS11q43O95749 details
Farnesyl pyrophosphate synthaseFDPS1q22P14324 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001285
DrugBank IDDB02552
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001463
KNApSAcK IDC00000846
Chemspider ID393471
KEGG Compound IDC05847
BioCyc IDGERANYL-PP
BiGG ID34712
Wikipedia LinkGeranyl_pyrophosphate
METLIN ID6134
PubChem Compound445995
PDB IDNot Available
ChEBI ID17211
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Geranylgeranyl pyrophosphate synthase
General function:
Involved in isoprenoid biosynthetic process
Specific function:
Catalyzes the trans-addition of the three molecules of IPP onto DMAPP to form geranylgeranyl pyrophosphate, an important precursor of carotenoids and geranylated proteins.
Gene Name:
GGPS1
Uniprot ID:
O95749
Molecular weight:
34870.625
Enzyme Details
2. Farnesyl pyrophosphate synthase
General function:
Involved in isoprenoid biosynthetic process
Specific function:
Key enzyme in isoprenoid biosynthesis which catalyzes the formation of farnesyl diphosphate (FPP), a precursor for several classes of essential metabolites including sterols, dolichols, carotenoids, and ubiquinones. FPP also serves as substrate for protein farnesylation and geranylgeranylation. Catalyzes the sequential condensation of isopentenyl pyrophosphate with the allylic pyrophosphates, dimethylallyl pyrophosphate, and then with the resultant geranylpyrophosphate to the ultimate product farnesyl pyrophosphate.
Gene Name:
FDPS
Uniprot ID:
P14324
Molecular weight:
48275.03
Enzyme Details
3. 4-hydroxybenzoate polyprenyltransferase, mitochondrial
General function:
Involved in prenyltransferase activity
Specific function:
Catalyzes the prenylation of para-hydroxybenzoate (PHB) with an all-trans polyprenyl group. Mediates the second step in the final reaction sequence of coenzyme Q (CoQ) biosynthesis, which is the condensation of the polyisoprenoid side chain with PHB.
Gene Name:
COQ2
Uniprot ID:
Q96H96
Molecular weight:
45593.67