Dimethylallylpyrophosphate (ECMDB01120) (M2MDB000260)
Record Information | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 13:45:34 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-13 12:56:10 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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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 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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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 |
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Molecular Framework | Aliphatic acyclic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -2 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | 234 - 238 °C | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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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: |
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KEGG Pathways: | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
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Concentrations | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Download (PDF) | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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External Links: |
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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. |