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 | PAMDB110150 |
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Identification |
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Name: |
5-amino-1-(5-phospho-β-D-ribosyl)imidazole |
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Description: | 5-aminoimidazole ribonucleotide (AIR), is an intermediate of purine nucleotide biosynthesis. It is also the precursor to 4-amino-2-methyl-5-hydroxymethylpyrimidine (HMP), the first product of pyrimidine biosynthesis. This reaction is mediated by the enzyme HMP-P kinase (ThiD). HMP is a precursor of thiamine phosphate (TMP), and subsequently to thiamine pyrophosphate (TPP). TPP is an essential cofactor in all living systems that plays a central role in metabolism. (PMID: 15326535 ). 5-Aminoimidazole ribonucleotide is a substrate for a number of proteins including: Scaffold attachment factor B2, Multifunctional protein ADE2, Pulmonary surfactant-associated protein B, Tumor necrosis factor receptor superfamily member 25, Pulmonary surfactant-associated protein C, Serine/threonine-protein kinase Chk1, Vinexin, Trifunctional purine biosynthetic protein adenosine-3, Antileukoproteinase 1 and Scaffold attachment factor B. |
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Structure |
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Synonyms: | -
5-aminoimidazole ribonucleotide
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5-amino-1-(5-phospho-D-ribosyl)imidazole
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5-aminoimidazole ribotide
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AIR
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1-(5'-phosphoribosyl)-5-aminoimidazole
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5'-phosphoribosyl-5-aminoimidazole
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phosphoribosylaminoimidazole
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Chemical Formula: |
C8H13N3O7P
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Average Molecular Weight: |
294.18 |
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Monoisotopic Molecular
Weight: |
296.0647613618 |
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InChI Key: |
PDACUKOKVHBVHJ-XVFCMESISA-M |
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InChI: |
InChI=1S/C8H14N3O7P/c9-5-1-10-3-11(5)8-7(13)6(12)4(18-8)2-17-19(14,15)16/h1,3-4,6-8,12-13H,2,9H2,(H2,14,15,16)/p-1/t4-,6-,7-,8-/m1/s1 |
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CAS
number: |
25635-88-5 |
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IUPAC Name: | 1-(5-O-phosphono-D-ribofuranosyl)-1H-imidazol-5-amine |
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Traditional IUPAC Name: |
5-aminoimidazole ribotide |
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SMILES: | C2([N+]=CN(C1(OC(COP([O-])(=O)[O-])C(O)C(O)1))C(N)=2) |
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Chemical Taxonomy |
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Taxonomy Description | This compound belongs to the class of chemical entities known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. |
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Kingdom |
Chemical entities |
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Super Class | Organic compounds |
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Class |
Organic oxygen compounds |
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Sub Class | Organooxygen compounds |
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Direct Parent |
Pentose phosphates |
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Alternative Parents |
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Substituents |
- Pentose phosphate
- Pentose-5-phosphate
- Imidazole ribonucleoside
- Glycosyl compound
- N-glycosyl compound
- Monosaccharide phosphate
- Monoalkyl phosphate
- Aminoimidazole
- Alkyl phosphate
- Primary aromatic amine
- Phosphoric acid ester
- N-substituted imidazole
- Organic phosphoric acid derivative
- Heteroaromatic compound
- Azole
- Imidazole
- Oxolane
- 1,2-diol
- Secondary alcohol
- Oxacycle
- Organoheterocyclic compound
- Azacycle
- Organic oxide
- Primary amine
- Organic nitrogen compound
- Alcohol
- Hydrocarbon derivative
- Amine
- Organopnictogen compound
- Organonitrogen compound
- Aromatic heteromonocyclic compound
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Molecular Framework |
Aromatic heteromonocyclic compounds |
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External Descriptors |
Not Available |
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Physical Properties |
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State: |
Solid |
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Charge: | 0 |
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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: |
- Vetvik H, Grewal HM, Haugen IL, Ahren C, Haneberg B: Mucosal antibodies can be measured in air-dried samples of saliva and feces. J Immunol Methods. 1998 Jun 1;215(1-2):163-72. [9744758 ]
- Ogata M, Michitsuji H, Fujiki Y: Estimating amounts of toluene inhaled by workers with protective mask using biological indicators of toluene. Toxicol Lett. 1999 Sep 5;108(2-3):233-9. [10511267 ]
- Chang HK, Weber ME, King M: Mucus transport by high-frequency nonsymmetrical oscillatory airflow. J Appl Physiol. 1988 Sep;65(3):1203-9. [3182490 ]
- Lawhorn BG, Mehl RA, Begley TP: Biosynthesis of the thiamin pyrimidine: the reconstitution of a remarkable rearrangement reaction. Org Biomol Chem. 2004 Sep 7;2(17):2538-46. Epub 2004 Aug 11. [15326535 ]
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Synthesis Reference: |
Groziak M P; Bhat B; Leonard N J Nonenzymatic synthesis of 5-aminoimidazole ribonucleoside and recognition of its facile rearrangement. Proceedings of the National Academy of Sciences of the United States of America (1988), 85(19), 7174-6. |
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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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