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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 | PAMDB000681 |
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Identification |
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| Name: |
DIMP |
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| Description: | dIMP is a deoxyribonucleoside and is considered a derivative of the nucleoside inosine, differing from the latter by the replacement of a hydroxyl group (-OH) by hydrogen (-H) at the 2' position of its ribose sugar moiety. The hydrolytic deamination of dAMP residues in DNA yields dIMP residues. The deamination of adenine residues in DNA generates hypoxanthine, which is mutagenic since it can pair not only with thymine but also with cytosine and therefore would result in A-T to G-C transitions after DNA replication. Hypoxanthine DNA glycosylase (EC 3.2.2.15) excises hypoxanthine from DNA containing dIMP residues in cells. (PMID: 10684927, 8016081) |
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Structure |
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| Synonyms: | - 2'-Deoxy-5'-inosinate
- 2'-Deoxy-5'-inosinic acid
- 2'-Deoxy-IMP
- 2'-Deoxyinosine 5'-monophosphate
- 2'-Deoxyinosine 5'-monophosphoric acid
- 2'-Deoxyinosine 5'-phosphate
- 2'-Deoxyinosine 5'-phosphoric acid
- 9-(2-deoxy-5-O-phosphono-β-D-erythro-pentofuranosyl)-9H-purin-6-ol
- 9-(2-Deoxy-5-O-phosphono-b-D-erythro-pentofuranosyl)-9H-purin-6-ol
- 9-(2-Deoxy-5-O-phosphono-b-delta-erythro-pentofuranosyl)-9H-purin-6-ol
- 9-(2-Deoxy-5-O-phosphono-b-δ-erythro-pentofuranosyl)-9H-purin-6-ol
- 9-(2-Deoxy-5-O-phosphono-beta-D-erythro-pentofuranosyl)-9H-purin-6-ol
- 9-(2-Deoxy-5-O-phosphono-beta-delta-erythro-pentofuranosyl)-9H-purin-6-ol
- 9-(2-Deoxy-5-O-phosphono-β-D-erythro-pentofuranosyl)-9H-purin-6-ol
- 9-(2-Deoxy-5-O-phosphono-β-δ-erythro-pentofuranosyl)-9H-purin-6-ol
- Deoxyinosine monophosphate
- Deoxyinosine monophosphoric acid
- DIMP
- Hypoxanthine deoxyriboside
- [(2R,3S,4R,5R)-3-hydroxy-5-(6-hydroxy-9H-purin-9-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate
- [(2R,3S,4R,5R)-3-Hydroxy-5-(6-hydroxy-9H-purin-9-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphoric acid
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Chemical Formula: |
C10H13N4O7P |
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| Average Molecular Weight: |
332.2066 |
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| Monoisotopic Molecular
Weight: |
332.052185302 |
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| InChI Key: |
PHNGFPPXDJJADG-RRKCRQDMSA-N |
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| InChI: | InChI=1S/C10H13N4O7P/c15-5-1-7(21-6(5)2-20-22(17,18)19)14-4-13-8-9(14)11-3-12-10(8)16/h3-7,15H,1-2H2,(H,11,12,16)(H2,17,18,19)/t5-,6+,7+/m0/s1 |
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| CAS
number: |
3393-18-8 |
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| IUPAC Name: | {[(2R,3S,5R)-3-hydroxy-5-(6-oxo-6,9-dihydro-3H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid |
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Traditional IUPAC Name: |
[(2R,3S,5R)-3-hydroxy-5-(6-oxo-3H-purin-9-yl)oxolan-2-yl]methoxyphosphonic acid |
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| SMILES: | O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)N1C=NC2=C1NC=NC2=O |
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Chemical Taxonomy |
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Taxonomy Description | This compound belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. |
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Kingdom |
Organic compounds |
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| Super Class | Nucleosides, nucleotides, and analogues |
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Class |
Purine nucleotides |
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| Sub Class | Purine ribonucleotides |
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Direct Parent |
Purine ribonucleoside monophosphates |
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| Alternative Parents |
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| Substituents |
- Purine ribonucleoside monophosphate
- Hypoxanthine
- 6-oxopurine
- Purine
- Imidazopyrimidine
- Monoalkyl phosphate
- Pyrimidone
- Alkyl phosphate
- Pyrimidine
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Organic phosphate
- N-substituted imidazole
- Saccharide
- Heteroaromatic compound
- Vinylogous amide
- Oxolane
- Imidazole
- Azole
- Secondary alcohol
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Alcohol
- Aromatic heteropolycyclic compound
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| Molecular Framework |
Aromatic heteropolycyclic 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: |
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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: |
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Spectra |
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| Spectra: |
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References |
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| 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
- Saparbaev M, Laval J: Excision of hypoxanthine from DNA containing dIMP residues by the Escherichia coli, yeast, rat, and human alkylpurine DNA glycosylases. Proc Natl Acad Sci U S A. 1994 Jun 21;91(13):5873-7. Pubmed: 8016081
- Saparbaev, M., Mani, J. C., Laval, J. (2000). "Interactions of the human, rat, Saccharomyces cerevisiae and Escherichia coli 3-methyladenine-DNA glycosylases with DNA containing dIMP residues." Nucleic Acids Res 28:1332-1339. Pubmed: 10684927
- 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: |
Ogilvie, Kelvin K.; Slotin, Lewis A. Anhydronucleosides. XI. Synthesis of nucleotides from 8,2'-thioanhydropurine nucleosides. Canadian Journal of Chemistry (1973), 51(14), 2397-405. |
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| Material Safety Data Sheet (MSDS) |
Not Available |
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