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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
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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
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 pyrophosphateDimethylallylpyrophosphate
Isopentenyl pyrophosphateDimethylallylpyrophosphate
Dimethylallylpyrophosphate + Isopentenyl pyrophosphateGeranyl-PP + Pyrophosphate
Dimethylallylpyrophosphate + Isopentenyl pyrophosphatePyrophosphate + Geranyl-PP
KEGG Reactions
Isopentenyl pyrophosphate + DimethylallylpyrophosphatePyrophosphate + Geranyl-PP
Isopentenyl pyrophosphateDimethylallylpyrophosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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

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.
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.
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.
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.