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Isopentenyl pyrophosphate (ECMDB01347) (M2MDB000348)
Record Information | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 13:50:27 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-06-03 15:53:57 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Isopentenyl pyrophosphate | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Isopentenyl pyrophosphate, IPP or isopentenyl diphosphate, is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. IPP is formed from Mevalonate-5-pyrophosphate, in a reaction catalyzed by the enzyme mevalonate-5-pyrophosphate decarboxylase. (wikipedia) | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C5H12O7P2 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 246.0921 Monoisotopic: 246.005825762 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | NUHSROFQTUXZQQ-UHFFFAOYSA-N | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h1,3-4H2,2H3,(H,9,10)(H2,6,7,8) | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 358-71-4 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | ({hydroxy[(3-methylbut-3-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | isopentenyl-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: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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 > Water + Isopentenyl pyrophosphate + NAD Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate >8 Pyrophosphate + Undecaprenyl diphosphate Dimethylallylpyrophosphate + Isopentenyl pyrophosphate > Geranyl-PP + Pyrophosphate Geranyl-PP + Isopentenyl pyrophosphate + Geranyl diphosphate <> Farnesyl pyrophosphate + Pyrophosphate Isopentenyl pyrophosphate <> Dimethylallylpyrophosphate Farnesyl pyrophosphate + 5 Isopentenyl pyrophosphate <> Octaprenyl diphosphate +5 Pyrophosphate Dimethylallylpyrophosphate + Isopentenyl pyrophosphate <> Pyrophosphate + Geranyl-PP Geranyl-PP + Isopentenyl pyrophosphate <> Pyrophosphate + Farnesyl pyrophosphate 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADPH + Hydrogen ion <> Isopentenyl pyrophosphate + NADP + Water Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate <> di-trans,poly-cis-Undecaprenyl diphosphate +8 Pyrophosphate + Undecaprenyl diphosphate Isopentenyl pyrophosphate + NAD + Water <> 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH + Hydrogen ion Geranyl-PP + Isopentenyl pyrophosphate > Farnesyl pyrophosphate + Pyrophosphate Isopentenyl pyrophosphate + NAD(P)<sup>+</sup> + Water < 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NAD(P)H + Hydrogen ion Farnesyl pyrophosphate + Isopentenyl pyrophosphate > all-<i>trans</i>-octaprenyl diphosphate + Pyrophosphate Farnesyl pyrophosphate + Isopentenyl pyrophosphate > Undecaprenyl diphosphate + Pyrophosphate Isopentenyl pyrophosphate > Dimethylallylpyrophosphate Farnesyl pyrophosphate + 5 Isopentenyl pyrophosphate >5 Pyrophosphate + Octaprenyl diphosphate Isopentenyl pyrophosphate + NAD(P)(+) + Water > 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NAD(P)H Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate >8 Pyrophosphate + di-trans,octa-cis-undecaprenyl diphosphate 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 > Water + NADPH + Isopentenyl pyrophosphate + Isopentenyl pyrophosphate Isopentenyl pyrophosphate + Isopentenyl pyrophosphate <> Dimethylallylpyrophosphate + Dimethylallylpyrophosphate Dimethylallylpyrophosphate + Isopentenyl pyrophosphate + Dimethylallylpyrophosphate + Isopentenyl pyrophosphate > Pyrophosphate + Geranyl-PP + Geranyl-PP Geranyl-PP + Isopentenyl pyrophosphate + Geranyl-PP + Isopentenyl pyrophosphate > Pyrophosphate + Farnesyl pyrophosphate + Farnesyl pyrophosphate Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate + Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate >8 Pyrophosphate + di-trans,octa-cis-undecaprenyl diphosphate Farnesyl pyrophosphate + 5 Isopentenyl pyrophosphate + Farnesyl pyrophosphate + 5 Isopentenyl pyrophosphate >5 Pyrophosphate + Octaprenyl diphosphate + Octaprenyl diphosphate More...Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate <> di-trans,octa-cis-undecaprenyl diphosphate +8 Pyrophosphate + Undecaprenyl diphosphate Dimethylallylpyrophosphate + Isopentenyl pyrophosphate > Geranyl-PP + Pyrophosphate Hydrogen ion + 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH > Water + Isopentenyl pyrophosphate + NAD Farnesyl pyrophosphate + 5 Isopentenyl pyrophosphate <> Octaprenyl diphosphate +5 Pyrophosphate Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate <> di-trans,octa-cis-undecaprenyl diphosphate +8 Pyrophosphate + Undecaprenyl diphosphate Dimethylallylpyrophosphate + Isopentenyl pyrophosphate > Geranyl-PP + Pyrophosphate | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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: | Kao, Chai-Lin; Kittleman, William; Zhang, Hua; Seto, Haruo; Liu, Hung-Wen. Stereochemical Analysis of Isopentenyl Diphosphate Isomerase Type II from Staphylococcus aureus Using Chemically Synthesized (S)- and (R)-[2-2H]Isopentenyl Diphosphates.Organic Let | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- 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 transferase activity, transferring alkyl or aryl (other than methyl) groups
- Specific function:
- Generates undecaprenyl pyrophosphate (UPP) from isopentenyl pyrophosphate (IPP). UPP is the precursor of glycosyl carrier lipid in the biosynthesis of bacterial cell wall polysaccharide components such as peptidoglycan and lipopolysaccharide
- Gene Name:
- uppS
- Uniprot ID:
- P60472
- Molecular weight:
- 28444
Reactions
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + di-trans,octa-cis-undecaprenyl 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. |
- General function:
- Involved in isoprenoid biosynthetic process
- Specific function:
- Supplies octaprenyl diphosphate, the precursor for the side chain of the isoprenoid quinones ubiquinone and menaquinone
- Gene Name:
- ispB
- Uniprot ID:
- P0AD57
- Molecular weight:
- 35217
Reactions
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate = 5 diphosphate + all-trans-octaprenyl diphosphate. |