MiMeDB: Showing metabocard for Acadesine (MMDBc0033502)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:51:17 UTC

Update Date

2024-04-20 06:09:07 UTC

Metabolite ID

MMDBc0033502

Metabolite Identification

Common Name

Acadesine

Description

1H-Imidazole-4-carboxamide, 5-amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-, also known as acadesine 5'-monophosphoric acid, 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. 1H-Imidazole-4-carboxamide, 5-amino-1-(5-O-phosphono-beta-D-ribofuranosyl)- has been detected, but not quantified in, herbs and spices. This could make 1H-imidazole-4-carboxamide, 5-amino-1-(5-O-phosphono-beta-D-ribofuranosyl)- a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 1H-Imidazole-4-carboxamide, 5-amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Acadesine 5'-monophosphoric acid	HMDB

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)

InChI Key

NOTGFIUVDGNKRI-UHFFFAOYSA-N

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Imidazole ribonucleosides and ribonucleotides

Sub Class

1-ribosyl-imidazolecarboxamides

Direct Parent

1-ribosyl-imidazolecarboxamides

Alternative Parents

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Saliva
Skeletal Muscle

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

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
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
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

HMDB0248071

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001213

KNApSAcK ID

Not Available

Chemspider ID

195

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

200

PDB ID

Not Available

ChEBI ID

93885

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 Acadesine (MMDBc0033502)

MOL for #<Metabolite:0x00007feced39cf38>

3D MOL for #<Metabolite:0x00007feced39cf38>

3D SDF for #<Metabolite:0x00007feced39cf38>

3D-SDF for #<Metabolite:0x00007feced39cf38>

PDB for #<Metabolite:0x00007feced39cf38>

3D PDB for #<Metabolite:0x00007feced39cf38>

SMILES for #<Metabolite:0x00007feced39cf38>

INCHI for #<Metabolite:0x00007feced39cf38>

Structure for #<Metabolite:0x00007feced39cf38>

3D Structure for #<Metabolite:0x00007feced39cf38>