ECMDB: Dimethylallylpyrophosphate (ECMDB01120) (M2MDB000260)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (4)XML

Proteins (1456)

Record Information

Version

2.0

Creation Date

2012-05-31 13:45:34 -0600

Update Date

2015-09-13 12:56:10 -0600

Secondary Accession Numbers

ECMDB01120

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

MOL SDF PDB SMILES InChI

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Isoprenoid phosphates

Direct Parent

Isoprenoid 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 Framework

Aliphatic acyclic compounds

External Descriptors

prenol phosphate (CHEBI:16057 )
C5 isoprenoids (hemiterpenes) (C00235 )
C5 isoprenoids (hemiterpenes) (LMPR01010001 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

234 - 238 °C

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	6.54 g/L	ALOGPS
logP	0.3	ALOGPS
logP	0.3	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.77	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	49.13 m³·mol⁻¹	ChemAxon
Polarizability	19.19 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

Secondary metabolites: isoprenoid biosynthesis (nonmevalonate pathway)	PW000975
Secondary metabolites: methylerythritol phosphate and polyisoprenoid biosynthesis	PW000958

KEGG Pathways:

Metabolic pathways eco01100
Terpenoid backbone biosynthesis ec00900
Zeatin biosynthesis ec00908

EcoCyc Pathways:

trans, trans-farnesyl diphosphate biosynthesis PWY-5123
methylerythritol phosphate pathway NONMEVIPP-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004j-9700000000-678abe159a77eee761ec	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - n/a 17V, negative	splash10-004i-3690000000-be82b5d8f3a1d675c6de	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-9660000000-6e2c34b818f993a966d7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9200000000-08a00604e05fbe36065b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9100000000-01b0ee5834d30012257b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0490000000-3b55dbb5fc89be39fcb4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9510000000-3521e5fb3dcbf2e3590e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-15ed4ecee7cc175e3833	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-3290000000-0d2c2679aff41e5a2aa8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-9100000000-1ca46da447e4b1c42222	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-a94de2be1fc80e7f3ca7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0490000000-d1cdea0da4ab0affcc51	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056s-9600000000-f42e0441eb797a5faf85	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-9700000000-c8d7613f7f9dc6aa7e47	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View 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)

Links

External Links:

Resource	Link
CHEBI ID	16057
HMDB ID	HMDB01120
Pubchem Compound ID	647
Kegg ID	C00235
ChemSpider ID	627
Wikipedia	Dimethylallylpyrophosphate
BioCyc ID	CPD-4211
EcoCyc ID	CPD-4211
Ligand Expo	DMA

Enzymes

Protein Details

1. tRNA dimethylallyltransferase

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.

Protein Details

2. Geranyltranstransferase

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.

Protein Details

3. 4-hydroxy-3-methylbut-2-enyl diphosphate reductase

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.

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:: idi
Uniprot ID:: Q46822
Molecular weight:: 20508

Reactions

Isopentenyl diphosphate = dimethylallyl diphosphate.

Dimethylallylpyrophosphate (ECMDB01120) (M2MDB000260)

Structure for #<Compound:0xa7c9d108>

Enzymes

Reactions

Reactions

Reactions

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