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

2024-04-30 19:44:03 UTC

Metabolite 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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
4-Amino-5-carbamoylimidazole	ChEBI
4-Amino-5-imidazolecarboxamide	ChEBI
5(4)-Amino-4(5)-imidazolecarboxamide	ChEBI
5-Amino-4-imidazolecarboxyamide	ChEBI
4-Aminoimidazole-5-carboxamide	HMDB
4-Carbamoyl-5-aminoimidazole	HMDB
4-Carboxamido-5-aminoimidazole	HMDB
5-Amino-1H-imidazole-4-carboxamide	HMDB
5-Amino-4-imidazolecarboxamide	HMDB
5-Amino-imidazole-4-carboxamide	HMDB
5-Aminoimidazol-4-carboxamide	HMDB
5-Aminoimidazole-4-carboxamide ribotide	HMDB
AIC	HMDB
AICA	HMDB
AICAR	HMDB
Colahepat	HMDB
Aminoimidazole carboxamide	HMDB
Carboxamide, aminoimidazole	HMDB

Molecular Formula

C₄H₆N₄O

Average Mass

126.1166

Monoisotopic Mass

126.054160834

IUPAC Name

4-amino-1H-imidazole-5-carboxamide

Traditional Name

4-aminoimidazole-5-carboxamide

CAS Registry Number

72-40-2

SMILES

NC(=O)C1=C(N)N=CN1

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

Description

Belongs to the class of organic compounds known as aminoimidazoles. These are organic compounds containing an amino group linked to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Imidazoles

Direct Parent

Aminoimidazoles

Alternative Parents

Substituents

Aminoimidazole
Heteroaromatic compound
Azacycle
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:2030 )
aminoimidazole (CHEBI:2030 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	124 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-0.96	ChemAxon
logS	-0.01	ALOGPS
pKa (Strongest Acidic)	12.74	ChemAxon
pKa (Strongest Basic)	5.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	97.79 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	32.98 m³·mol⁻¹	ChemAxon
Polarizability	11.37 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0f9i-4965000000-81d31245e06d3f90edaf	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-0kgk-3936100000-5d3d51d18ff3e42df0e8	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0f9i-4965000000-81d31245e06d3f90edaf	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0kgk-3936100000-5d3d51d18ff3e42df0e8	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-3690000000-139a77fec9d1fff114cd	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f9i-1943000000-fc9ed76a2b879a05cac3	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f6t-0924100000-3f9bf805d01a76aee672	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0059-9700000000-59d0b74e7172f25684a9	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0900000000-7f5a5c4e183bae4dac94	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a6r-4900000000-f098009008beac308c09	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4l-9100000000-0558a1cf6f49c407a5c9	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-49775423db52b263ab35	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-61b854e636df8aefa743	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03fr-0900000000-dbf2f2a8c104b1886d61	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03di-0900000000-4e7fa2397876cb8faa22	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03di-4900000000-c5cc732d595521342e28	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9200000000-4f8ffe0195fc8b4eefb3	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9000000000-2475e395f0201d1ae8dc	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0006-9000000000-e01c782c531e25d73332	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-5ac6303648d30c83dd8c	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-5900000000-891e8af2ee696c82bb67	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-d969e00c4e0a26137fb4	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-5900000000-38872de2bfb260a5d96f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0563-9400000000-5d37f6e245dbc41ac3e4	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-9797d793034ec5f4f97f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-00d6654a49bf268f862d	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01q9-9300000000-8eb581fb8e27a0073dde	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-a1482203ba6eb659c755	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004l-8900000000-fa9ba502d467ade9fdca	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-26ef6e91d6b3541e3748	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-74703663982d7ee978ef	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

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

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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0018256	L-Glutamine	L-Glutamic acid	Imidazole glycerol phosphate synthase subunit HisH	Synthesis	PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Melanoma		Association	Human Blood	HMDB	7172404
Sarcoma		Association	Human Blood	HMDB	7172404

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	5.55	0.79	39.67	uM	Adult (>18 years old)	Both	Malignant melanoma or sarcoma	HMDB	7172404
Human Urine	Detected and Quantified	<0.11			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	30817767
Human Urine	Detected and Quantified	0.21	0.05	0.52	umol/mmol creatinine	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.
Human Urine	Detected and Quantified	0.47	0.20	0.82	umol/mmol creatinine	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.
Human Fibroblasts	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0003192

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023121

KNApSAcK ID

Not Available

Chemspider ID

9298

KEGG Compound ID

C04051

BioCyc ID

CPD-3762

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

629

PubChem Compound

9679

PDB ID

Not Available

ChEBI ID

2030

Food Biomarker Ontology

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:0x00007fd12e063d88>

3D MOL for #<Metabolite:0x00007fd12e063d88>

3D SDF for #<Metabolite:0x00007fd12e063d88>

3D-SDF for #<Metabolite:0x00007fd12e063d88>

PDB for #<Metabolite:0x00007fd12e063d88>

3D PDB for #<Metabolite:0x00007fd12e063d88>

SMILES for #<Metabolite:0x00007fd12e063d88>

INCHI for #<Metabolite:0x00007fd12e063d88>

Structure for #<Metabolite:0x00007fd12e063d88>

3D Structure for #<Metabolite:0x00007fd12e063d88>