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Record Information |
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| Version |
1.0 |
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| Update Date |
1/22/2018 11:54:54 AM |
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Metabolite ID | PAMDB001868 |
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Identification |
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| Name: |
1-Hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate |
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| Description: | 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate is a member of the chemical class known as Organic Pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O. 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate is an intermediate in the mehtylerithritol phosphate pathway. . D-glyceraldehyde-3-phosphate and pyruvate are initially combined to yield 1-deoxy-D-xylylose 5-phosphate (DXP). DXP is then rearranged and reduced to generate the pathway's namesake compound, 2-C-methyl-D-erythritol 4-phosphate (MEP). In the third reaction MEP is converted into 4-diphosphocytidyl-2-C-methylerythritol, which is subsequently phosphorylated at the 2 position hydroxy group, yielding 4-diphosphocytidyl-2C-methylerythritol 2-phosphate. This product is then converted into 2-C-methyl-D-erythritol 2,4-cyclodiphosphate. This compound is then reduced to generate 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate. In the final step, this diphosphate compound is converted by a single enzyme into a 5-6:1 ratio of IPP and DMAPP This ratio is subsequently adjusted to 7:3 by isopentenyl diphosphate isomerase. Both IPP and DMAPP then become the basic building blocks of polyisoprenoid biosynthesis. |
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Structure |
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| Synonyms: | - 1-Hydroxy-2-methyl-2-(E)-butenyl 4-diphosphoric acid
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Chemical Formula: |
C5H9O8P2 |
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| Average Molecular Weight: |
259.0677 |
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| Monoisotopic Molecular
Weight: |
258.977265288 |
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| InChI Key: |
MDSIZRKJVDMQOQ-GORDUTHDSA-K |
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| InChI: | InChI=1S/C5H12O8P2/c1-5(4-6)2-3-12-15(10,11)13-14(7,8)9/h2,6H,3-4H2,1H3,(H,10,11)(H2,7,8,9)/p-3/b5-2+ |
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| CAS
number: |
Not Available |
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| IUPAC Name: | {[(2E)-4-hydroxy-3-methylbut-2-en-1-yl phosphonato]oxy}phosphonate |
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Traditional IUPAC Name: |
hmbpp |
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| SMILES: | [H]\C(COP([O-])(=O)OP([O-])([O-])=O)=C(\C)CO |
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Chemical Taxonomy |
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Taxonomy Description | This compound 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. |
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Kingdom |
Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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Class |
Prenol lipids |
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| Sub Class | Isoprenoid phosphates |
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Direct Parent |
Isoprenoid phosphates |
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| Alternative Parents |
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| Substituents |
- Organic pyrophosphate
- Isoprenoid phosphate
- Alkyl phosphate
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Organic phosphate
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Alcohol
- Organic anion
- Aliphatic acyclic compound
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| Molecular Framework |
Aliphatic acyclic compounds |
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| External Descriptors |
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Physical Properties |
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| State: |
Not Available |
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| Charge: | -2 |
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Melting point: |
Not Available |
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| Experimental Properties: |
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| Predicted Properties |
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Biological Properties |
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| Cellular Locations: |
Cytoplasm |
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| Reactions: | |
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Pathways: |
Not Available |
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Spectra |
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| Spectra: |
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References |
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| References: |
- 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
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| Synthesis Reference: |
Not Available |
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| Material Safety Data Sheet (MSDS) |
Not Available |
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Links |
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| External Links: |
| Resource | Link |
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| CHEBI ID | 128753 | | HMDB ID | Not Available | | Pubchem Compound ID | 21597501 | | Kegg ID | Not Available | | ChemSpider ID | 10224038 | | Wikipedia ID | Not Available | | BioCyc ID | Not Available |
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