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Dimethylallylpyrophosphate (YMDB00095)

Identification
YMDB IDYMDB00095
NameDimethylallylpyrophosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1,1-Dimethyl-4-phenylpiperazinium iodide
  • 2-Isopentenyl diphosphate
  • 3-methyl-2-Buten-1-ol pyrophosphate
  • 3-methyl-2-Buten-1-ol trihydrogen pyrophosphate
  • 3-Methyl-2-butenyl pyrophosphate
  • 3-methylbut-2-enyl pyrophosphate
  • 3,3-Dimethylallyl pyrophosphate
  • delta-Prenyl diphosphate
  • delta2-Isopentenyl diphosphate
  • delta2-isopentenyl-diphosphate
  • Dimethylallyl diphosphate
  • dimethylallyl pyrophosphate
  • dimethylallyl-diphosphate
  • dimethylallyl-PP
  • dimethylallyl-PPi
  • dimethylallyl-pyrophosphate
  • Dimethylallylpyrophosphate
  • Dimethylallylpyrophosphic acid
  • Diphosphoric acid mono(3-methyl-2-butenyl) ester
  • DMAPP
  • DMPP
  • IPE
  • Prenyl diphosphate
  • prenyl-diphosphate
  • 3-Methylbut-2-enyl phosphono hydrogen phosphate
  • Monoprenyl diphosphate
  • Prenol pyrophosphate
  • 2-Isopentenyl diphosphoric acid
  • 3,3-Dimethylallyl pyrophosphoric acid
  • 3-Methylbut-2-enyl phosphono hydrogen phosphoric acid
  • delta-Prenyl diphosphoric acid
  • Δ-prenyl diphosphate
  • Δ-prenyl diphosphoric acid
  • delta2-Isopentenyl diphosphoric acid
  • Δ2-isopentenyl diphosphate
  • Δ2-isopentenyl diphosphoric acid
  • Dimethylallyl diphosphoric acid
  • Dimethylallyl pyrophosphoric acid
  • Monoprenyl diphosphoric acid
  • Prenol pyrophosphoric acid
  • Prenyl diphosphoric acid
  • Dimethylallylpyrophosphoric acid
  • 3,3-Dimethylallyl pyrophosphate, (14)C-labeled
  • DMADP CPD
  • 3-Methyl-2-butenyl trihydrogen diphosphate
  • gamma,gamma-Dimethylallyl pyrophosphate
  • γ,γ-Dimethylallyl pyrophosphate
CAS number358-72-5
WeightAverage: 246.0921
Monoisotopic: 246.005825762
InChI KeyCBIDRCWHNCKSTO-UHFFFAOYSA-N
InChIInChI=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)
IUPAC Name({hydroxy[(3-methylbut-2-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid
Traditional IUPAC Namedimethylallyl diphosphate
Chemical FormulaC5H12O7P2
SMILES[H]OP(=O)(O[H])OP(=O)(O[H])OC([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]
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
StateSolid
Charge0
Melting point234-238 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Organoleptic PropertiesNot Available
SMPDB Pathways
Cholesterol biosynthesis and metabolism CE(10:0)PW002545 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(12:0)PW002548 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(14:0)PW002544 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(16:0)PW002550 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(18:0)PW002551 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Steroid biosynthesisec00100 Map00100
Terpenoid backbone biosynthesisec00900 Map00900
SMPDB Reactions
Isopentenyl pyrophosphate ↔ Dimethylallylpyrophosphate
Isopentenyl pyrophosphate → Dimethylallylpyrophosphate
Dimethylallylpyrophosphate + Isopentenyl pyrophosphate → Geranyl-PP + Pyrophosphate
Dimethylallylpyrophosphate + Isopentenyl pyrophosphate → Pyrophosphate + Geranyl-PP
KEGG Reactions
Isopentenyl pyrophosphate + Dimethylallylpyrophosphate → Pyrophosphate + Geranyl-PP
Isopentenyl pyrophosphate ↔ Dimethylallylpyrophosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-9700000000-678abe159a77eee761ecJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - n/a 17V, negativesplash10-004i-3690000000-be82b5d8f3a1d675c6deJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-9660000000-6e2c34b818f993a966d7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9200000000-08a00604e05fbe36065bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9100000000-01b0ee5834d30012257bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0490000000-3b55dbb5fc89be39fcb4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9510000000-3521e5fb3dcbf2e3590eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-15ed4ecee7cc175e3833JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-3290000000-0d2c2679aff41e5a2aa8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-9100000000-1ca46da447e4b1c42222JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-a94de2be1fc80e7f3ca7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0490000000-d1cdea0da4ab0affcc51JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056s-9600000000-f42e0441eb797a5faf85JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9700000000-c8d7613f7f9dc6aa7e47JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Hsu, A. Y., Do, T. Q., Lee, P. T., Clarke, C. F. (2000). "Genetic evidence for a multi-subunit complex in the O-methyltransferase steps of coenzyme Q biosynthesis." Biochim Biophys Acta 1484:287-297.10760477
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16057
HMDB IDHMDB01120
Pubchem Compound ID647
Kegg IDC00235
ChemSpider ID627
FOODB IDFDB022434
WikipediaDimethylallylpyrophosphate
BioCyc IDCPD-4211

Enzymes

Protein Details
1. tRNA dimethylallyltransferase, mitochondrial
General function:
Involved in ATP binding
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:
MOD5
Uniprot ID:
P07884
Molecular weight:
50236.19922
Reactions
Dimethylallyl diphosphate + tRNA → diphosphate + tRNA containing 6-dimethylallyladenosine.
Protein Details
2. Farnesyl pyrophosphate synthase
General function:
Involved in isoprenoid biosynthetic process
Specific function:
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:
ERG20
Uniprot ID:
P08524
Molecular weight:
40483.0
Reactions
Dimethylallyl diphosphate + isopentenyl diphosphate → diphosphate + geranyl diphosphate.
Geranyl diphosphate + isopentenyl diphosphate → diphosphate + (2E,6E)-farnesyl diphosphate.
Protein Details
3. Geranylgeranyl pyrophosphate synthase
General function:
Involved in isoprenoid biosynthetic process
Specific function:
Catalyzes the trans-addition of the 3 molecules of IPP onto DMAPP to form geranylgeranyl pyrophosphate. Required for the membrane attachment of YPT1 and SEC4. May be involved in vesicle trafficking and protein sorting
Gene Name:
BTS1
Uniprot ID:
Q12051
Molecular weight:
38651.0
Reactions
Dimethylallyl diphosphate + isopentenyl diphosphate → diphosphate + geranyl diphosphate.
Geranyl diphosphate + isopentenyl diphosphate → diphosphate + (2E,6E)-farnesyl diphosphate.
Trans,trans-farnesyl diphosphate + isopentenyl diphosphate → diphosphate + geranylgeranyl diphosphate.
Protein Details
4. Isopentenyl-diphosphate Delta-isomerase
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:
P15496
Molecular weight:
33351.30078
Reactions
Isopentenyl diphosphate → dimethylallyl diphosphate.