MiMeDB: Showing metabocard for AICAR (MMDBc0029664)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:36:38 UTC

Update Date

2024-10-13 08:35:14 UTC

Metabolite ID

MMDBc0029664

Metabolite Identification

Common Name

AICAR

Description

AICAR (5-amino-4-carboxamide imidazole riboside 5'-phosphate), is a by-product of histidine biosynthesis, and its (ribo)triphosphate derivative, ZTP, has been detected in E. coli. It is also an intermediate in the generation of inosine monophosphate. The purH gene product catalyzes the conversion of 5-aminoimidazole-4-carboxamide ribonucleotide (AICAR) to 5-form-aminoimidazole-4-carboxamide ribonucleotide (FAICAR) and inosine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₉H₁₅N₄O₈P

Average Mass

338.2112

Monoisotopic Mass

338.062749988

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

3031-94-5

SMILES

Not Available

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

InChI Key

NOTGFIUVDGNKRI-UUOKFMHZSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Feces
Saliva
Skeletal Muscle

Tissue Locations

Skeletal Muscle

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192104	Adenine phosphoribosyltransferase	Enzyme	P07741	Homo sapiens
MMDBp0192229	Adenylosuccinate lyase	Enzyme	P30566	Homo sapiens
MMDBp0192500	Bifunctional purine biosynthesis protein PURH	Enzyme	P31939	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000243	SAICAR	AICAR	adenylosuccinate lyase	VMH	1302001 2004782
MMDBr0007250	SAICAR	AICAR	Not Available	VMH	30371894
MMDBr0007706	10-Formyltetrahydrofolic acid	Phosphoribosyl formamidocarboxamide	Not Available	VMH; KEGG	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	13	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; River trout ; Rat ; Sheep ; Chicken ; Cattle ; Turkey ; Human subgingival plaque	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	475	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool; Catfish	Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	513	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; River trout ; Rat ; Sheep ; Chicken ; Cattle ; Turkey ; Human subgingival plaque	Unknown; Metabolic reconstruction
Bacteria	Actinobacteria	15	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva; Cattle	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	157	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva; Cattle	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	2	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	132	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	29	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool; Catfish	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	9	Human feces; Pig ; Human	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Cyanobacteria	32	Human
Bacteria/Eubacteria	Aquificae	4
Bacteria/Eubacteria	Chloroflexi	9
Bacteria/Eubacteria	Chlorobi	11
Bacteria/Eubacteria	Deinococcus-thermus	5
Bacteria/Eubacteria	Elusimicrobia	2
Bacteria/Eubacteria	Thermotogae	4
Eukaryota/Fungi	Ascomycota	4	Human feces; Human saliva	Unknown
Bacteria	nah	1
Bacteria/Eubacteria	Nitrospirae	1
Archaea/Archaea	Euryarchaeota	33		Metabolic reconstruction
Bacteria	Tenericutes	1
Archaea/Archaea	Crenarchaeota	10		Metabolic reconstruction
Archaea/Archaea	Thaumarchaeota	2		Metabolic reconstruction
Archaea/Archaea	Korarchaeota	1
Bacteria	Spirochaetes	1	Human feces; Pig ; Human	Metabolic reconstruction
Bacteria/Eubacteria	Acidobacteria	3
Bacteria/Eubacteria	Dictyoglomi	2

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Saliva	Detected and Quantified	0.441	0.133	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.504	0.126	uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.548	0.153	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Skeletal muscle	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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 ]
Koistinen HA, Chibalin AV, Zierath JR: Aberrant p38 mitogen-activated protein kinase signalling in skeletal muscle from Type 2 diabetic patients. Diabetologia. 2003 Oct;46(10):1324-8. doi: 10.1007/s00125-003-1196-3. Epub 2003 Aug 23. [PubMed:12937895 ]

Showing metabocard for AICAR (MMDBc0029664)

MOL for #<Metabolite:0x00007f3e10d05138>

3D MOL for #<Metabolite:0x00007f3e10d05138>

3D SDF for #<Metabolite:0x00007f3e10d05138>

3D-SDF for #<Metabolite:0x00007f3e10d05138>

PDB for #<Metabolite:0x00007f3e10d05138>

3D PDB for #<Metabolite:0x00007f3e10d05138>

SMILES for #<Metabolite:0x00007f3e10d05138>

INCHI for #<Metabolite:0x00007f3e10d05138>

Structure for #<Metabolite:0x00007f3e10d05138>

3D Structure for #<Metabolite:0x00007f3e10d05138>