Record Information
Version2.0
Creation Date2012-05-31 13:45:34 -0600
Update Date2015-09-13 12:56:10 -0600
Secondary Accession Numbers
  • ECMDB01120
Identification
Name:Dimethylallylpyrophosphate
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.
Structure
Thumb
Synonyms:
  • δ-prenyl diphosphate
  • δ-prenyl diphosphoric acid
  • δ2-isopentenyl-diphosphate
  • δ2-isopentenyl-diphosphoric acid
  • 1,1-Dimethyl-4-phenylpiperazinium iodide
  • 2-Isopentenyl diphosphate
  • 2-Isopentenyl diphosphoric acid
  • 3,3-Dimethylallyl pyrophosphate
  • 3,3-Dimethylallyl pyrophosphoric acid
  • 3-Methyl-2-Buten-1-ol pyrophosphate
  • 3-Methyl-2-buten-1-ol pyrophosphoric acid
  • 3-Methyl-2-Buten-1-ol trihydrogen pyrophosphate
  • 3-Methyl-2-buten-1-ol trihydrogen pyrophosphoric acid
  • 3-Methyl-2-butenyl pyrophosphate
  • 3-Methyl-2-butenyl pyrophosphoric acid
  • 3-Methylbut-2-enyl pyrophosphate
  • 3-Methylbut-2-enyl pyrophosphoric acid
  • Delta-Prenyl diphosphate
  • delta-Prenyl diphosphoric acid
  • Delta2-Isopentenyl diphosphate
  • delta2-Isopentenyl diphosphoric acid
  • Delta2-isopentenyl-diphosphate
  • delta2-Isopentenyl-diphosphoric acid
  • Di-CH3-allyl-PPi
  • Dimethylallyl diphosphate
  • Dimethylallyl diphosphoric acid
  • Dimethylallyl pyrophosphate
  • Dimethylallyl pyrophosphoric acid
  • Dimethylallyl-diphosphate
  • Dimethylallyl-diphosphoric acid
  • Dimethylallyl-PP
  • Dimethylallyl-PPi
  • Dimethylallyl-pyrophosphate
  • Dimethylallyl-pyrophosphoric acid
  • Dimethylallylpyrophosphate
  • Dimethylallylpyrophosphoric acid
  • Diphosphate mono(3-methyl-2-butenyl) ester
  • Diphosphorate mono(3-methyl-2-butenyl) ester
  • Diphosphoric acid mono(3-methyl-2-butenyl) ester
  • DMAPP
  • DMAProP
  • DMPP
  • DPP
  • IPE
  • Prenyl diphosphate
  • Prenyl diphosphoric acid
  • Prenyl-diphosphate
  • Prenyl-diphosphoric acid
  • δ-Prenyl diphosphate
  • δ-Prenyl diphosphoric acid
  • δ2-Isopentenyl diphosphate
  • δ2-Isopentenyl diphosphoric acid
  • δ2-Isopentenyl-diphosphate
  • δ2-Isopentenyl-diphosphoric acid
Chemical Formula:C5H12O7P2
Weight:Average: 246.0921
Monoisotopic: 246.005825762
InChI Key:CBIDRCWHNCKSTO-UHFFFAOYSA-N
InChI: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)
CAS number:358-72-5
IUPAC Name:({hydroxy[(3-methylbut-2-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid
Traditional IUPAC Name:dimethylallyl diphosphate
SMILES:CC(C)=CCO[P@](O)(=O)OP(O)(O)=O
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
  • 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
Physical Properties
State:Solid
Charge:-2
Melting point:234 - 238 °C
Experimental Properties:
PropertyValueSource
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
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Hydrogen ion + 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH > Dimethylallylpyrophosphate + Water + NAD
Dimethylallylpyrophosphate + Isopentenyl pyrophosphate > Geranyl-PP + Pyrophosphate
Isopentenyl pyrophosphate <> Dimethylallylpyrophosphate
Dimethylallylpyrophosphate + tRNA <> Pyrophosphate + tRNA containing 6-isopentenyladenosine
Dimethylallylpyrophosphate + Isopentenyl pyrophosphate <> Pyrophosphate + Geranyl-PP
Dimethylallylpyrophosphate + NADP + Water <> 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADPH + Hydrogen ion
Dimethylallylpyrophosphate + NAD + Water <> 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH + Hydrogen ion
NAD(P)<sup>+</sup> + Dimethylallylpyrophosphate + Water < NAD(P)H + Hydrogen ion + 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate
Isopentenyl pyrophosphate > Dimethylallylpyrophosphate
Dimethylallylpyrophosphate + NAD(P)(+) + Water > 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NAD(P)H
Dimethylallylpyrophosphate + tRNA > Pyrophosphate + tRNA containing 6-dimethylallyladenosine
Isopentenyl pyrophosphate + NAD + NADP + Water + Dimethylallylpyrophosphate <> 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH + NADPH + Hydrogen ion
1-Hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + Hydrogen ion + NADPH + NADPH > NADP + Water + Dimethylallylpyrophosphate + Dimethylallylpyrophosphate
Isopentenyl pyrophosphate + Isopentenyl pyrophosphate <> Dimethylallylpyrophosphate + Dimethylallylpyrophosphate
Dimethylallylpyrophosphate + Isopentenyl pyrophosphate + Dimethylallylpyrophosphate + Isopentenyl pyrophosphate > Pyrophosphate + Geranyl-PP + Geranyl-PP
Dimethylallylpyrophosphate + Isopentenyl pyrophosphate > Geranyl-PP + Pyrophosphate
Dimethylallylpyrophosphate + tRNA <> Pyrophosphate + tRNA containing 6-isopentenyladenosine
Dimethylallylpyrophosphate + Isopentenyl pyrophosphate > Geranyl-PP + Pyrophosphate
Dimethylallylpyrophosphate + tRNA <> Pyrophosphate + tRNA containing 6-isopentenyladenosine
SMPDB Pathways:
Secondary metabolites: isoprenoid biosynthesis (nonmevalonate pathway)PW000975 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary metabolites: methylerythritol phosphate and polyisoprenoid biosynthesisPW000958 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-9700000000-678abe159a77eee761ecView in MoNA
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
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID16057
HMDB IDHMDB01120
Pubchem Compound ID647
Kegg IDC00235
ChemSpider ID627
WikipediaDimethylallylpyrophosphate
BioCyc IDCPD-4211
EcoCyc IDCPD-4211
Ligand ExpoDMA

Enzymes

General function:
Involved in ATP binding
Specific function:
Catalyzes the transfer of a dimethylallyl group onto the adenine at position 37 in tRNAs that read codons beginning with uridine, leading to the formation of N6-(dimethylallyl)adenosine (i(6)A)
Gene Name:
miaA
Uniprot ID:
P16384
Molecular weight:
35065
Reactions
Dimethylallyl diphosphate + tRNA = diphosphate + tRNA containing 6-dimethylallyladenosine.
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.
General function:
Involved in isopentenyl diphosphate biosynthetic process, mevalonate-independent pathway
Specific function:
Converts 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate into isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP). Is also involved in penicillin tolerance and control of the stringent response. Seems to directly or indirectly interact with relA to maintain it in an inactive form during normal growth
Gene Name:
ispH
Uniprot ID:
P62623
Molecular weight:
34774
Reactions
Isopentenyl diphosphate + NAD(P)(+) + H(2)O = (E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + NAD(P)H.
Dimethylallyl diphosphate + NAD(P)(+) + H(2)O = (E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + NAD(P)H.
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:
idi
Uniprot ID:
Q46822
Molecular weight:
20508
Reactions
Isopentenyl diphosphate = dimethylallyl diphosphate.