Record Information |
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Version | 1.0 |
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Created at | 2022-02-14 20:56:07 UTC |
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Updated at | 2022-03-10 22:17:52 UTC |
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NP-MRD ID | NP0044403 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | AICAR |
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Description | AICAR, also known as Z-nucleotide or ZMP, belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond. AICAR is a strong basic compound (based on its pKa). AICAR exists in all living species, ranging from bacteria to humans. Within humans, AICAR participates in a number of enzymatic reactions. In particular, fumaric acid and AICAR can be biosynthesized from SAICAR; which is catalyzed by the enzyme adenylosuccinate lyase. In addition, 10-formyltetrahydrofolate and AICAR can be converted into tetrahydrofolic acid and phosphoribosyl formamidocarboxamide; which is mediated by the enzyme bifunctional purine biosynthesis protein purh. In humans, AICAR is involved in the metabolic disorder called the purine nucleoside phosphorylase deficiency pathway. Outside of the human body, AICAR has been detected, but not quantified in, several different foods, such as cardoons, chayotes, almonds, buffalo currants, and rambutans. This could make AICAR a potential biomarker for the consumption of these foods. AICAR has been used clinically to treat and protect against cardiac ischemic injury. The drug was first used in the 1980s as a method to preserve blood flow to the heart during surgery and is currently of interest as a potential treatment for diabetes by increasing the metabolic activity of tissues by changing the physical composition of muscle. 5-Aminoimidazole-4-carboxamide ribonucleotide is an intermediate in the generation of inosine monophosphate and analog of adenosine monophosphate (AMP) that is capable of stimulating AMP-dependent protein kinase (AMPK) activity. AICAR is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
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Structure | NC(=O)C1=C(N)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O InChI=1S/C9H15N4O8P/c10-7-4(8(11)16)12-2-13(7)9-6(15)5(14)3(21-9)1-20-22(17,18)19/h2-3,5-6,9,14-15H,1,10H2,(H2,11,16)(H2,17,18,19)/t3-,5-,6-,9-/m1/s1 |
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Synonyms | Value | Source |
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1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide | ChEBI | 5'-Phospho-ribosyl-5-amino-4-imidazole carboxamide | ChEBI | 5'-Phosphoribosyl-5-amino-4-imidazolecarboxamide | ChEBI | 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide | ChEBI | 5-Aminoimidazole-4-carboxamide ribotide | ChEBI | 5-Phosphoribosyl-4-carbamoyl-5-aminoimidazole | ChEBI | Acadesine 5'-monophosphate | ChEBI | AICA-Ribonucleotide | ChEBI | 5-Amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide | Kegg | Acadesine 5'-monophosphoric acid | Generator | 5-Amino-1-(5-phospho-b-D-ribosyl)imidazole-4-carboxamide | Generator | 5-Amino-1-(5-phospho-β-D-ribosyl)imidazole-4-carboxamide | Generator | 5'-p-Ribosyl-5-amino-4-imidazole carboxamide | HMDB | 5'-Phosphoribosyl-5-amino-4-imidazole carboxamide | HMDB | 5-Amino-4-imidazolecarboxamide ribotide | HMDB | AICA Ribonucleotide | HMDB | Aminoimidazole carboxamide ribonucleotide | HMDB | Z-Nucleotide | HMDB | 4-Carboxy-5-aminoimidazole ribotide | HMDB | 5-Amino-1-beta-D-ribofuranosylimidazole-4-carboxamide monophosphate | HMDB | 5-Amino-4-imidazolecarboxamide ribofuranoside 5'-monophosphate | HMDB | AICA Ribonucleotide, (D-ribofuranosyl)-isomer | HMDB | AICAriboside 5'-monophosphate | HMDB | CAIR | HMDB | ZMP | HMDB | (2R,3S,4R,5R)-5-(4-Carbam0yl-5-aminoimidazol-1-yl)-3,4-dihydroxyoxolan-2-yljmethyl dihydrogen phosphate | HMDB | 5'-Phospho-beta-D-ribosyl-5-amino-4-imidazolecarboxamide | HMDB | 5'-Phospho-β-D-ribosyl-5-amino-4-imidazolecarboxamide | HMDB | 5-Amino-1-(5'-phosphofuranoribosyl)-4-imidazolecarboxamide | HMDB | 5-Amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-1H-imidazole-4-carboxamide | HMDB | 5-Amino-1-(5-O-phosphono-β-D-ribofuranosyl)-1H-imidazole-4-carboxamide | HMDB | 5-Amino-1-(5’-phosphofuranoribosyl)-4-imidazolecarboxamide | HMDB | 5-Amino-1beta-D-ribofuranosylimidazole-4-carboxamide 5'-phosphate | HMDB | 5-Amino-1β-D-ribofuranosylimidazole-4-carboxamide 5'-phosphate | HMDB | 5-Amino-1β-D-ribofuranosylimidazole-4-carboxamide 5’-phosphate | HMDB | 5-Amino-4-imidazolecarboxamide ribonucleoside 5'-monophosphate | HMDB | 5-Amino-4-imidazolecarboxamide ribonucleoside 5’-monophosphate | HMDB | 5-Amino-4-imidazolecarboxamide ribonucleotide | HMDB | 5-Amino-4-imidazolecarboxamide riboside 5'-monophosphate | HMDB | 5-Amino-4-imidazolecarboxamide riboside 5’-monophosphate | HMDB | 5-Aminoimidazole-4-carboxamide ribonucleotide | HMDB | 5-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranosyl 5'-monophosphate | HMDB | 5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5’-monophosphate | HMDB | 5’-Phospho-β-D-ribosyl-5-amino-4-imidazolecarboxamide | HMDB | 5’-Phosphoribosyl-5-amino-4-imidazolecarboxamide | HMDB | AICA Ribotide | HMDB | AICAR | HMDB | AICAR (5-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranosyl 5'-monophosphate) | HMDB | AICAR (5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5'-monophosphate) | HMDB | AICAR (5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5’-monophosphate) | HMDB | Acadesine 5’-monophosphate | HMDB | Aminoimidazolecarboxamide ribonucleotide | HMDB |
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Chemical Formula | C9H15N4O8P |
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Average Mass | 338.2112 Da |
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Monoisotopic Mass | 338.06275 Da |
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IUPAC Name | {[(2R,3S,4R,5R)-5-(5-amino-4-carbamoyl-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid |
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Traditional Name | aica ribonucleotide |
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CAS Registry Number | 3031-94-5 |
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SMILES | NC(=O)C1=C(N)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O |
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InChI Identifier | InChI=1S/C9H15N4O8P/c10-7-4(8(11)16)12-2-13(7)9-6(15)5(14)3(21-9)1-20-22(17,18)19/h2-3,5-6,9,14-15H,1,10H2,(H2,11,16)(H2,17,18,19)/t3-,5-,6-,9-/m1/s1 |
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InChI Key | NOTGFIUVDGNKRI-UUOKFMHZSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Imidazole ribonucleosides and ribonucleotides |
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Sub Class | 1-ribosyl-imidazolecarboxamides |
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Direct Parent | 1-ribosyl-imidazolecarboxamides |
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Alternative Parents | |
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Substituents | - 1-ribosyl-imidazolecarboxamide
- Pentose phosphate
- Pentose-5-phosphate
- Glycosyl compound
- N-glycosyl compound
- Monosaccharide phosphate
- Pentose monosaccharide
- 2-heteroaryl carboxamide
- Imidazole-4-carbonyl group
- Monoalkyl phosphate
- Aminoimidazole
- Monosaccharide
- N-substituted imidazole
- Organic phosphoric acid derivative
- Alkyl phosphate
- Phosphoric acid ester
- Azole
- Imidazole
- Heteroaromatic compound
- Vinylogous amide
- Tetrahydrofuran
- Primary carboxylic acid amide
- Secondary alcohol
- Amino acid or derivatives
- 1,2-diol
- Carboxamide group
- Organoheterocyclic compound
- Azacycle
- Oxacycle
- Carboxylic acid derivative
- Primary amine
- Organonitrogen compound
- Organopnictogen compound
- Organooxygen compound
- Organic oxygen compound
- Amine
- Organic oxide
- Hydrocarbon derivative
- Organic nitrogen compound
- Alcohol
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | 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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General References | - Shi X, Wu Y, Ai Z, Liu X, Yang L, Du J, Shao J, Guo Z, Zhang Y: AICAR sustains J1 mouse embryonic stem cell self-renewal and pluripotency by regulating transcription factor and epigenetic modulator expression. Cell Physiol Biochem. 2013;32(2):459-75. doi: 10.1159/000354451. Epub 2013 Aug 27. [PubMed:23988673 ]
- Shi X, YongyanWu, Ai Z, Du J, Cao L, Guo Z, Zhang Y: MicroRNA modulation induced by AICA ribonucleotide in J1 mouse ES cells. PLoS One. 2014 Jul 31;9(7):e103724. doi: 10.1371/journal.pone.0103724. eCollection 2014. [PubMed:25078608 ]
- Dixon R, Fujitaki J, Sandoval T, Kisicki J: Acadesine (AICA-riboside): disposition and metabolism of an adenosine-regulating agent. J Clin Pharmacol. 1993 Oct;33(10):955-8. doi: 10.1002/j.1552-4604.1993.tb01929.x. [PubMed:8227467 ]
- Jakobsen SN, Hardie DG, Morrice N, Tornqvist HE: 5'-AMP-activated protein kinase phosphorylates IRS-1 on Ser-789 in mouse C2C12 myotubes in response to 5-aminoimidazole-4-carboxamide riboside. J Biol Chem. 2001 Dec 14;276(50):46912-6. doi: 10.1074/jbc.C100483200. Epub 2001 Oct 11. [PubMed:11598104 ]
- Koistinen HA, Galuska D, Chibalin AV, Yang J, Zierath JR, Holman GD, Wallberg-Henriksson H: 5-amino-imidazole carboxamide riboside increases glucose transport and cell-surface GLUT4 content in skeletal muscle from subjects with type 2 diabetes. Diabetes. 2003 May;52(5):1066-72. doi: 10.2337/diabetes.52.5.1066. [PubMed:12716734 ]
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