Dimethylallylpyrophosphate (PAMDB000260)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000260
Identification
Name: Dimethylallylpyrophosphate
Description:Dimethylallyl 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
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🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: 246.0921
Monoisotopic Molecular Weight: 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
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
  • Isoprenoid phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: 234 - 238 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility6.54 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity49.13 m3·mol-1ChemAxon
Polarizability19.19 Å3ChemAxon
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 + NADP + Water <> 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADPH + Hydrogen ion
NAD(P)<sup>+</sup> + Dimethylallylpyrophosphate + Water < NAD(P)H + Hydrogen ion + 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate
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
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
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 Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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