MiMeDB: Showing metabocard for 5-Amino-4-imidazolecarboxyamide (MMDBc0030023)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:51:01 UTC

Update Date

2022-08-31 17:38:48 UTC

MiMeDB ID

MMDBc0030023

Metabolite Identification

Common Name

5-Amino-4-imidazolecarboxyamide

Description

5-Amino-4-imidazolecarboxyamide is a metabolite of purine metabolism. Adenine phosphoribosyltransferase [EC:2.4.2.7] catalyzes both the formation of 5-Amino-4-imidazolecarboxyamide and its conversion to 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide, also called AICAR. (KEGG)

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₄H₆N₄O

Average Molecular Weight

126.1166

Monoisotopic Molecular Weight

126.054160834

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

72-40-2

SMILES

Not Available

InChI Identifier

InChI=1S/C4H6N4O/c5-3-2(4(6)9)7-1-8-3/h1H,5H2,(H2,6,9)(H,7,8)

InChI Key

DVNYTAVYBRSTGK-UHFFFAOYSA-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

Blood
Fibroblasts
Platelet
Skeletal Muscle
Urine

Tissue Locations

Fibroblasts
Platelet
Skeletal Muscle

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

#<MetaboliteProteinLink:0x000055b76d394958>

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference
Melanoma		This associated disease is originally imported from HMDB metabolite HMDB0003192 concentration id 17513	Association	Human Blood		7172404	details
Sarcoma		This associated disease is originally imported from HMDB metabolite HMDB0003192 concentration id 17513	Association	Human Blood		7172404	details

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
	Proteobacteria	1	Human	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Age	Sex	Health Condition	Data Source	Reference
Human	Detected and Quantified	5.55	0.79	39.67	Adult (>18 years old)	Both	Malignant melanoma or sarcoma	HMDB	7172404	details
Human	Detected and Quantified	<0.11			Infant (0-1 year old)	Both	Normal	HMDB	30817767	details
Human	Detected and Quantified	0.21	0.05	0.52	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.	details
Human	Detected and Quantified	0.47	0.20	0.82	Adult (>18 years old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.	details
Human Fibroblasts	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Platelet	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Skeletal Muscle	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597	details

External Links

Not Available

References

Synthesis Reference

Not Available

General References

Lower GM Jr, Lanphear SP, Johnson BM, Bryan GT: Aryl and heterocyclic diazo compounds as potential environmental electrophiles. J Toxicol Environ Health. 1977 May;2(5):1095-107. doi: 10.1080/15287397709529507. [PubMed:17015 ]
Morris GS, Simmonds HA, Davies PM: Use of biological fluids for the rapid diagnosis of potentially lethal inherited disorders of human purine and pyrimidine metabolism. Biomed Chromatogr. 1986 Jun;1(3):109-18. doi: 10.1002/bmc.1130010305. [PubMed:3506820 ]
Fiore D, Jackson AJ, Didolkar MS, Dandu VR: Simultaneous determination of dacarbazine, its photolytic degradation product, 2-azahypoxanthine, and the metabolite 5-aminoimidazole-4-carboxamide in plasma and urine by high-pressure liquid chromatography. Antimicrob Agents Chemother. 1985 Jun;27(6):977-9. doi: 10.1128/AAC.27.6.977. [PubMed:4026274 ]
Zheng D, MacLean PS, Pohnert SC, Knight JB, Olson AL, Winder WW, Dohm GL: Regulation of muscle GLUT-4 transcription by AMP-activated protein kinase. J Appl Physiol (1985). 2001 Sep;91(3):1073-83. doi: 10.1152/jappl.2001.91.3.1073. [PubMed:11509501 ]
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 ]
Wang W, Yang X, Lopez de Silanes I, Carling D, Gorospe M: Increased AMP:ATP ratio and AMP-activated protein kinase activity during cellular senescence linked to reduced HuR function. J Biol Chem. 2003 Jul 18;278(29):27016-23. doi: 10.1074/jbc.M300318200. Epub 2003 May 1. [PubMed:12730239 ]
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 ]
Fleming I, Schulz C, Fichtlscherer B, Kemp BE, Fisslthaler B, Busse R: AMP-activated protein kinase (AMPK) regulates the insulin-induced activation of the nitric oxide synthase in human platelets. Thromb Haemost. 2003 Nov;90(5):863-71. doi: 10.1160/TH03-04-0228. [PubMed:14597982 ]
Shang J, Lehrman MA: Activation of glycogen phosphorylase with 5-aminoimidazole-4-carboxamide riboside (AICAR). Assessment of glycogen as a precursor of mannosyl residues in glycoconjugates. J Biol Chem. 2004 Mar 26;279(13):12076-80. doi: 10.1074/jbc.M400431200. Epub 2004 Jan 16. [PubMed:14729664 ]
Al-Khalili L, Krook A, Zierath JR, Cartee GD: Prior serum- and AICAR-induced AMPK activation in primary human myocytes does not lead to subsequent increase in insulin-stimulated glucose uptake. Am J Physiol Endocrinol Metab. 2004 Sep;287(3):E553-7. doi: 10.1152/ajpendo.00161.2004. Epub 2004 May 18. [PubMed:15149951 ]
Holloszy JO: Exercise-induced increase in muscle insulin sensitivity. J Appl Physiol (1985). 2005 Jul;99(1):338-43. doi: 10.1152/japplphysiol.00123.2005. [PubMed:16036907 ]
Nakano M, Hamada T, Hayashi T, Yonemitsu S, Miyamoto L, Toyoda T, Tanaka S, Masuzaki H, Ebihara K, Ogawa Y, Hosoda K, Inoue G, Yoshimasa Y, Otaka A, Fushiki T, Nakao K: alpha2 isoform-specific activation of 5'adenosine monophosphate-activated protein kinase by 5-aminoimidazole-4-carboxamide-1-beta-D-ribonucleoside at a physiological level activates glucose transport and increases glucose transporter 4 in mouse skeletal muscle. Metabolism. 2006 Mar;55(3):300-8. doi: 10.1016/j.metabol.2005.09.003. [PubMed:16483872 ]

Showing metabocard for 5-Amino-4-imidazolecarboxyamide (MMDBc0030023)

MOL for #<Metabolite:0x000055b76dd05000>

3D MOL for #<Metabolite:0x000055b76dd05000>

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3D-SDF for #<Metabolite:0x000055b76dd05000>

PDB for #<Metabolite:0x000055b76dd05000>

3D PDB for #<Metabolite:0x000055b76dd05000>

SMILES for #<Metabolite:0x000055b76dd05000>

INCHI for #<Metabolite:0x000055b76dd05000>

Structure for #<Metabolite:0x000055b76dd05000>

3D Structure for #<Metabolite:0x000055b76dd05000>