Classification Term: 2876
1-ribosyl-imidazolecarboxamides (ontology term: CHEMONTID:0001420)
Organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond." []
found 11 associated metabolites at sub_class metabolite taxonomy ontology rank level.
Ancestor: Imidazole ribonucleosides and ribonucleotides
Child Taxonomies: 1-phosphoribosyl-imidazolecarboxamides
AICAR
Aicar, also known as 5-phosphoribosyl-5-amino-4-imidazolecarboxamide or 5-aminoimidazole-4-carboxamide ribotide, is a member of the class of compounds known as 1-ribosyl-imidazolecarboxamides. 1-ribosyl-imidazolecarboxamides are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond. Aicar is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Aicar can be found in a number of food items such as safflower, greenthread tea, common pea, and wild leek, which makes aicar a potential biomarker for the consumption of these food products. Aicar can be found primarily in saliva, as well as in human skeletal muscle tissue. Aicar exists in all living species, ranging from bacteria to humans. In humans, aicar is involved in few metabolic pathways, which include azathioprine action pathway, mercaptopurine action pathway, purine metabolism, and thioguanine action pathway. Aicar is also involved in several metabolic disorders, some of which include mitochondrial DNA depletion syndrome, purine nucleoside phosphorylase deficiency, xanthinuria type II, and gout or kelley-seegmiller syndrome. AICAR also known as ZMP is an analog of AMP that is capable of stimulating AMP-dependent protein kinase activity(AMPK). AICAR is an intermediate in the generation of inosine monophosphate. AICAR is being clinically used to treat and protect against cardiac ischemic injury. AICAR can enter cardiac cells to inhibit adenosine kinase and adenosine deaminase. It enhances the rate of nucleotide re-synthesis increasing adenosine generation from adenosine monophosphate only during conditions of myocardial ischemia. AICAR increases glucose uptake by inducing translocation of GLUT4 and/or by activating the p38 MAPK pathway. Acquisition and generation of the data is financially supported in part by CREST/JST. COVID info from COVID-19 Disease Map D007004 - Hypoglycemic Agents Corona-virus KEIO_ID A133 Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS
Phosphoribosyl formamidocarboxamide
This compound is an intermediate in purine metabolism, where it is the byproduct of phosphoribosylaminoimidazolecarboxamide formyltransferase (EC 2.1.2.3) and IMP cyclohydrolase (EC 3.5.4.10). It is also a byproduct of Ligases (EC 6.3.4.-). COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS
SAICAR
SAICAR, also known as succinylaminoimidazolecarboxamide ribotide or phosphoribosylaminoimidazolesuccinocarboxamide, is a substrate for the multifunctional protein ADE2. SAICAR is an intermediate in purine metabolism. SAICAR is converted from 5-aminoimidazole-4-carboxyribonucleotide (CAIR) via phosphoribosylaminoimidazolesuccinocarboxamide synthetase (EC: 6.3.2.6) or SAICAR synthase. This enzyme catalyzes the eighth step in the biosynthesis of purine nucleotides. SAICAR (a ribotide) can lose its phosphate group leading to the appearance of a riboside known as succinylaminoimidazolecarboxamide riboside (SAICAriboside) in cerebrospinal fluid, in urine, and, to a lesser extent, in plasma. This particular riboside (called SAICAr) is characteristic of a heritable deficiency known as adenylosuccinate lyase deficiency (ADSL). On the other hand, the ribotide (SAICAR) is generally harmless and is an essential intermediate in purine metabolism. When present in sufficiently high levels, SAICAR can act as an oncometabolite. An oncometabolite is a compound that promotes tumour growth and survival. As an oncometabolite, high levels of SAICAR stimulate pyruvate kinase isoform M2 and promote cancer cell survival in glucose-limited conditions such as aerobic glycolysis (PMID: 23086999). SAICAR (or (S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate) is a substrate for the multifunctional protein ADE2. SAICAR is an intermediate in purine metabolism. (S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate is converted from 5-Amino-1-(5-phospho-D-ribosyl) imidazole-4-carboxylate via phosphoribosylaminoimidazole-succinocarboxamide synthase [EC: 6.3.2.6] or SAICAR synthase. This enzyme catalyses the seventh step out of ten in the biosynthesis of purine nucleotides. The appearance of succinylaminoimidazolecarboxamide riboside (SAICAriboside) and succinyladenosine (S-Ado) in cerebrospinal fluid, urine, and to a lesser extent in plasma is characteristic of a heritable deficiency Adenylosuccinate lyase deficiency. [HMDB]. SAICAR is found in many foods, some of which are sweet potato, black chokeberry, common wheat, and globe artichoke. SAICAR. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=3031-95-6 (retrieved 2024-08-20) (CAS RN: 3031-95-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Phosphoribosylformimino-AICAR-P
1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide, also known as phosphoribosyl-formimino-aicar-phosphate or 5-profar, is a member of the class of compounds known as 1-ribosyl-imidazolecarboxamides. 1-ribosyl-imidazolecarboxamides are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond. 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide is slightly soluble (in water) and a moderately acidic compound (based on its pKa). 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide can be found in a number of food items such as wild rice, caraway, red huckleberry, and red algae, which makes 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide a potential biomarker for the consumption of these food products. 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide may be a unique S.cerevisiae (yeast) metabolite. Phosphoribosylformimino-AICAR-P, also known as phosphoribosylformiminoAICAR-phosphate, 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. Phosphoribosylformimino-AICAR-P is a very strong basic compound (based on its pKa). Phosphoribosylformimino-AICAR-P is found in both E. coli and humans.
Phosphoribulosylformimino-AICAR-P
Phosphoribulosylformimino-AICAR-P 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. Phosphoribulosylformimino-AICAR-P is a strong basic compound (based on its pKa). Phosphoribulosylformimino-AICAR-P is found in both E. coli and humans. A human metabolite taken as a putative food compound of mammalian origin [HMDB]
Mizoribine
Mizoribine belongs to the family of 1-Ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond. D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D007155 - Immunologic Factors > D007166 - Immunosuppressive Agents D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents D002491 - Central Nervous System Agents > D000700 - Analgesics C308 - Immunotherapeutic Agent > C574 - Immunosuppressant D000893 - Anti-Inflammatory Agents D000970 - Antineoplastic Agents D018501 - Antirheumatic Agents D004791 - Enzyme Inhibitors Mizoribine (NSC 289637), an imidazole nucleoside, inhibits HCV RNA replication with IC50 of approximately 100 μM for anti-HCV activity. Immunosuppressant[1]. Mizoribine, an IMPDH inhibitor, inhibits replication of SARS-CoV with IC50s of 3.5 μg/mL and 16 μg/mL for SARS-CoV Frankfurt-1 and SARS-CoV HKU39849, respectively[2]. Mizoribine (NSC 289637), an imidazole nucleoside, inhibits HCV RNA replication with IC50 of approximately 100 μM for anti-HCV activity. Immunosuppressant[1]. Mizoribine, an IMPDH inhibitor, inhibits replication of SARS-CoV with IC50s of 3.5 μg/mL and 16 μg/mL for SARS-CoV Frankfurt-1 and SARS-CoV HKU39849, respectively[2].
5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide(2-)
5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide(2-) is considered to be slightly soluble (in water) and acidic
Succinylaminoimidazole carboxamide riboside
Succinylaminoimidazole carboxamide riboside, also known as SAICAr, is the riboside form of the better known compound SAICAR (the ribotide). Ribosides chemically resemble ribotides except they do not contain a phosphate group. The appearance of succinylaminoimidazolecarboxamide riboside (SAICAriboside) and succinyladenosine (S-Ado) in cerebrospinal fluid, in urine, and, to a lesser extent, in plasma is characteristic of a heritable deficiency known as adenylosuccinate lyase deficiency (ADSL). Adenylosuccinate lyase deficiency is responsible for a range of symptoms that involve psychomotor retardation, often accompanied by epileptic seizures, and autistic features. In adenylosuccinate lyase deficiency it is believed that the buildup of SAICAr causes neurotoxic effects. In the severely affected individuals, the concentration levels of SAICAr and S-Ado are comparable, whereas in people with milder forms of the disease, the concentration of S-Ado is more than double that of those more severely affected, while SAICAr concentration levels remain comparable. Therefore, when present in sufficiently high levels, SAICAr can act as a metabotoxin and an acidogen. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated adenylosuccinate lyase deficiency. Many affected children with organic acidemias experience intellectual disability or delayed development.
