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Record Information |
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| Version |
1.0 |
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| Update Date |
1/22/2018 12:54:54 PM |
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Metabolite ID | PAMDB110165 |
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Identification |
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| Name: |
isopentenyl diphosphate |
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| Description: | Trianion of isopentenyl diphosphate arising from deprotonation of the three OH groups of the diphosphate. |
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Structure |
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| Synonyms: | -
isopentenyl-pp
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isopentenyl pyrophosphate
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IPP
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δ(3)-isopentenyl-PP
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Δ3-isopentenyl-PP
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3-methylbut-3-enyl diphosphate
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3-methylbut-3-enyl pyrophosphate
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Chemical Formula: |
C5H9O7P2
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| Average Molecular Weight: |
243.07 |
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| Monoisotopic Molecular
Weight: |
246.0058257599 |
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| InChI Key: |
NUHSROFQTUXZQQ-UHFFFAOYSA-K |
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| 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)/p-3 |
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| CAS
number: |
358-71-4 |
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| IUPAC Name: | 3-methylbut-3-en-1-yl diphosphate |
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Traditional IUPAC Name: |
isopentenyl-diphosphate |
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| SMILES: | C=C(C)CCOP([O-])(=O)OP([O-])(=O)[O-] |
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Chemical Taxonomy |
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Taxonomy Description | This compound belongs to the class of chemical entities 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 |
Chemical entities |
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| Super Class | Organic compounds |
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Class |
Lipids and lipid-like molecules |
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| Sub Class | Prenol lipids |
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Direct Parent |
Isoprenoid phosphates |
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| Alternative Parents |
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| 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
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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: |
Solid |
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| Charge: | -3 |
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Melting point: |
Not Available |
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| Experimental Properties: |
| Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties |
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Biological Properties |
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| Cellular Locations: |
Not Available |
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| Reactions: | |
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Pathways: |
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Spectra |
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| Spectra: |
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References |
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| References: |
- Reichenberg A, Hintz M, Kletschek Y, Kuhl T, Haug C, Engel R, Moll J, Ostrovsky DN, Jomaa H, Eberl M (2003)Replacing the pyrophosphate group of HMB-PP by a diphosphonate function abrogates Its potential to activate human gammadelta T cells but does not lead to competitive antagonism. Bioorganic & medicinal chemistry letters 13, Pubmed: 12657258
- Nagaki M, Kannari H, Ishibashi J, Maki Y, Nishino T, Ogura K, Koyama T (1998)Substrate specificity of thermostable farnesyl diphosphate synthase with alkyl group homologs of isopentenyl diphosphate. Bioorganic & medicinal chemistry letters 8, Pubmed: 9873578
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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 |
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| Material Safety Data Sheet (MSDS) |
Not Available |
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Links |
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| External Links: |
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