Record Information
Version1.0
Creation date2011-09-21 00:13:55 UTC
Update date2020-09-17 15:41:14 UTC
Primary IDFDB022434
Secondary Accession Numbers
  • FDB030829
Chemical Information
FooDB NameDimethylallylpyrophosphate
DescriptionDimethylallylpyrophosphate, also known as 2-isopentenyl diphosphate or delta-prenyl diphosphoric acid, 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. Dimethylallylpyrophosphate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
CAS Number358-72-5
Structure
Thumb
Synonyms
SynonymSource
2-Isopentenyl diphosphateChEBI
3,3-Dimethylallyl pyrophosphateChEBI
3-Methylbut-2-enyl phosphono hydrogen phosphateChEBI
delta-Prenyl diphosphateChEBI
delta2-Isopentenyl diphosphateChEBI
Dimethylallyl diphosphateChEBI
Dimethylallyl pyrophosphateChEBI
DMAPPChEBI
Monoprenyl diphosphateChEBI
Prenol pyrophosphateChEBI
Prenyl diphosphateKegg
2-Isopentenyl diphosphoric acidGenerator
3,3-Dimethylallyl pyrophosphoric acidGenerator
3-Methylbut-2-enyl phosphono hydrogen phosphoric acidGenerator
delta-Prenyl diphosphoric acidGenerator
Δ-prenyl diphosphateGenerator
Δ-prenyl diphosphoric acidGenerator
delta2-Isopentenyl diphosphoric acidGenerator
Δ2-isopentenyl diphosphateGenerator
Δ2-isopentenyl diphosphoric acidGenerator
Dimethylallyl diphosphoric acidGenerator
Dimethylallyl pyrophosphoric acidGenerator
Monoprenyl diphosphoric acidGenerator
Prenol pyrophosphoric acidGenerator
Prenyl diphosphoric acidGenerator
Dimethylallylpyrophosphoric acidGenerator
1,1-Dimethyl-4-phenylpiperazinium iodideHMDB
3-Methyl-2-buten-1-ol pyrophosphateHMDB
3-Methyl-2-buten-1-ol trihydrogen pyrophosphateHMDB
3-Methyl-2-butenyl pyrophosphateHMDB
3-Methylbut-2-enyl pyrophosphateHMDB
Delta2-Isopentenyl-diphosphateHMDB
Dimethylallyl-diphosphateHMDB
Dimethylallyl-PPHMDB
Dimethylallyl-ppiHMDB
Dimethylallyl-pyrophosphateHMDB
Diphosphoric acid mono(3-methyl-2-butenyl) esterHMDB
DMPPHMDB
IPEHMDB
Prenyl-diphosphateHMDB
3,3-Dimethylallyl pyrophosphate, (14)C-labeledHMDB
DMADP CPDHMDB
3-Methyl-2-butenyl trihydrogen diphosphateHMDB
DimethylallylpyrophosphateHMDB
gamma,gamma-Dimethylallyl pyrophosphateHMDB
γ,γ-Dimethylallyl pyrophosphateHMDB
2-Isopentenyl diateChEBI
2-Isopentenyl diic acidGenerator
3-Methyl-2-buten-1-ol pyroateHMDB
3-methyl-2-Buten-1-ol pyrophosphatehmdb
3-Methyl-2-buten-1-ol trihydrogen pyroateHMDB
3-methyl-2-Buten-1-ol trihydrogen pyrophosphatehmdb
3-Methyl-2-butenyl pyroateHMDB
3-Methylbut-2-enyl ONO hydrogen ateChEBI
3-Methylbut-2-enyl ONO hydrogen ic acidGenerator
3-Methylbut-2-enyl pyroateHMDB
3-methylbut-2-enyl pyrophosphatehmdb
3,3-Dimethylallyl pyroateChEBI
3,3-Dimethylallyl pyroic acidGenerator
delta-Prenyl diateChEBI
delta-Prenyl diic acidGenerator
delta2-Isopentenyl diateChEBI
delta2-Isopentenyl diic acidGenerator
Delta2-Isopentenyl-diateHMDB
delta2-isopentenyl-diphosphatehmdb
Dimethylallyl diateChEBI
Dimethylallyl diic acidGenerator
Dimethylallyl pyroateChEBI
Dimethylallyl pyroic acidGenerator
dimethylallyl pyrophosphatehmdb
Dimethylallyl-diateHMDB
dimethylallyl-diphosphatehmdb
dimethylallyl-PPhmdb
dimethylallyl-PPihmdb
Dimethylallyl-pyroateHMDB
dimethylallyl-pyrophosphatehmdb
DimethylallylpyroateHMDB
Dimethylallylpyrophosphic acidhmdb
Dioric acid mono(3-methyl-2-butenyl) esterHMDB
Monoprenyl diateChEBI
Monoprenyl diic acidGenerator
Prenol pyroateChEBI
Prenol pyroic acidGenerator
Prenyl diateChEBI
Prenyl diic acidGenerator
Prenyl-diateHMDB
prenyl-diphosphatehmdb
δ-prenyl diateGenerator
δ-prenyl diic acidGenerator
δ2-isopentenyl diateGenerator
δ2-isopentenyl diic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility6.54 g/LALOGPS
logP0.3ALOGPS
logP0.3ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity49.13 m³·mol⁻¹ChemAxon
Polarizability19.19 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H12O7P2
IUPAC name({hydroxy[(3-methylbut-2-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid
InChI IdentifierInChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h3H,4H2,1-2H3,(H,9,10)(H2,6,7,8)
InChI KeyCBIDRCWHNCKSTO-UHFFFAOYSA-N
Isomeric SMILESCC(C)=CCO[P@](O)(=O)OP(O)(O)=O
Average Molecular Weight246.0921
Monoisotopic Molecular Weight246.005825762
Classification
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
  • 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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSDimethylallylpyrophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004j-9700000000-678abe159a77eee761ecSpectrum
Predicted GC-MSDimethylallylpyrophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - n/a 17V, negativesplash10-004i-3690000000-be82b5d8f3a1d675c6de2020-07-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-9660000000-6e2c34b818f993a966d72015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9200000000-08a00604e05fbe36065b2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9100000000-01b0ee5834d30012257b2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0490000000-3b55dbb5fc89be39fcb42015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9510000000-3521e5fb3dcbf2e3590e2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-15ed4ecee7cc175e38332015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-3290000000-0d2c2679aff41e5a2aa82021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-9100000000-1ca46da447e4b1c422222021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-a94de2be1fc80e7f3ca72021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0490000000-d1cdea0da4ab0affcc512021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056s-9600000000-f42e0441eb797a5faf852021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9700000000-c8d7613f7f9dc6aa7e472021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID627
ChEMBL IDCHEMBL343480
KEGG Compound IDC00235
Pubchem Compound ID647
Pubchem Substance IDNot Available
ChEBI ID16057
Phenol-Explorer IDNot Available
DrugBank IDDB01785
HMDB IDHMDB01120
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID131960
KNApSAcK IDNot Available
HET IDDMA
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDimethylallylpyrophosphate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Geranylgeranyl pyrophosphate synthaseGGPS1O95749
Farnesyl pyrophosphate synthaseFDPSP14324
Pathways
NameSMPDB LinkKEGG Link
Steroid BiosynthesisSMP00023 map00100
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference