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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 08:03:07 UTC
HMDB IDHMDB0001120
Secondary Accession Numbers
  • HMDB01120
  • HMDB02101
Metabolite Identification
Common NameDimethylallylpyrophosphate
DescriptionDimethylallyl pyrophosphate (or -diphosphate) (DMAPP) is an intermediate product of both mevalonic acid (MVA) pathway and DOXP/MEP pathway. It is an isomer of isopentenyl pyrophosphate (IPP) and exists in virtually all life forms. (wikipedia).
Structure
Thumb
Synonyms
ValueSource
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
2-Isopentenyl diphosphoric acidGenerator
Dimethylallylpyrophosphoric 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
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
Prenyl-diphosphateHMDB
3,3-Dimethylallyl pyrophosphate, (14)C-labeledMeSH
DMADP CPDMeSH
Chemical FormulaC5H12O7P2
Average Molecular Weight246.0921
Monoisotopic Molecular Weight246.005825762
IUPAC Name({hydroxy[(3-methylbut-2-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid
Traditional Namedimethylallyl diphosphate
CAS Registry Number358-72-5
SMILES
CC(C)=CCO[P@](O)(=O)OP(O)(O)=O
InChI Identifier
InChI=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
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as isoprenoid phosphates. These are prenol lipids containing a phosphate group linked to an isoprene (2-methylbuta-1,3-diene) unit.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassPrenol lipids
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

Biological Location:

  Subcellular:

  Tissue and substructures:

Source:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

Role

Industrial application:

  Pharmaceutical industry:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point234 - 238 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-9660000000-6e2c34b818f993a966d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9200000000-08a00604e05fbe36065bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9100000000-01b0ee5834d30012257bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0490000000-3b55dbb5fc89be39fcb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9510000000-3521e5fb3dcbf2e3590eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-15ed4ecee7cc175e3833View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Peroxisome
Biofluid LocationsNot Available
Tissue Location
  • Muscle
Pathways
NameSMPDB/PathwhizKEGG
Alendronate pathwayPw000137Pw000137 greyscalePw000137 simpleNot Available
Atorvastatin PathwayPw000275Pw000275 greyscalePw000275 simpleNot Available
CHILD SyndromePw000096Pw000096 greyscalePw000096 simpleNot Available
Cerivastatin PathwayPw000271Pw000271 greyscalePw000271 simpleNot Available
Cholesteryl ester storage diseasePw000484Pw000484 greyscalePw000484 simpleNot Available
Displaying entries 1 - 5 of 23 in total
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022434
KNApSAcK IDNot Available
Chemspider ID627
KEGG Compound IDC00235
BioCyc IDCPD-4211
BiGG ID131960
Wikipedia LinkDimethylallylpyrophosphate
METLIN ID6016
PubChem Compound647
PDB IDDMA
ChEBI ID16057
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Smith AS, Smid SD: Impaired capsaicin and neurokinin-evoked colonic motility in inflammatory bowel disease. J Gastroenterol Hepatol. 2005 May;20(5):697-704. [PubMed:15853981 ]

Enzymes

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
Reactions
Dimethylallylpyrophosphate + Isopentenyl pyrophosphate → Pyrophosphate + Geranyl-PPdetails
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
Reactions
Dimethylallylpyrophosphate + Isopentenyl pyrophosphate → Pyrophosphate + Geranyl-PPdetails
General function:
Lipid transport and metabolism
Specific function:
Catalyzes the 1,3-allylic rearrangement of the homoallylic substrate isopentenyl (IPP) to its highly electrophilic allylic isomer, dimethylallyl diphosphate (DMAPP).
Gene Name:
IDI2
Uniprot ID:
Q9BXS1
Molecular weight:
26752.33
Reactions
Isopentenyl pyrophosphate → Dimethylallylpyrophosphatedetails
General function:
Involved in isopentenyl-diphosphate delta-isomerase activity
Specific function:
Catalyzes the 1,3-allylic rearrangement of the homoallylic substrate isopentenyl (IPP) to its highly electrophilic allylic isomer, dimethylallyl diphosphate (DMAPP).
Gene Name:
IDI1
Uniprot ID:
Q13907
Molecular weight:
32485.165
Reactions
Isopentenyl pyrophosphate → Dimethylallylpyrophosphatedetails
General function:
Not Available
Specific function:
Catalyzes the transfer of a dimethylallyl group onto the adenine at position 37 of both cytosolic and mitochondrial tRNAs, leading to the formation of N6-(dimethylallyl)adenosine (i(6)A).
Gene Name:
TRIT1
Uniprot ID:
Q9H3H1
Molecular weight:
52724.84
Reactions
Dimethylallylpyrophosphate + tRNA → Pyrophosphate + tRNA containing 6-dimethylallyladenosinedetails
Dimethylallylpyrophosphate + tRNA → Pyrophosphate + tRNA containing 6-isopentenyladenosinedetails