Bovine Metabolome Database: Showing metabocard for 5-Aminoimidazole-4-carboxamide (BMDB0003192)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:03:04 UTC

Update Date

2020-05-21 16:27:08 UTC

BMDB ID

BMDB0003192

Secondary Accession Numbers

BMDB03192

Metabolite Identification

Common Name

5-Aminoimidazole-4-carboxamide

Description

5-Aminoimidazole-4-carboxamide, also known as AIC or 4-amino-5-carbamoylimidazole, belongs to the class of organic compounds known as aminoimidazoles. These are organic compounds containing an amino group linked to an imidazole ring. 5-Aminoimidazole-4-carboxamide is a very strong basic compound (based on its pKa). 5-Aminoimidazole-4-carboxamide exists in all living organisms, ranging from bacteria to humans. 5-Aminoimidazole-4-carboxamide is a potentially toxic compound.

Structure

MOL SDF 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

Chemical Formula

C₄H₆N₄O

Average Molecular Weight

126.1166

Monoisotopic Molecular Weight

126.054160834

IUPAC Name

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

Traditional Name

4-aminoimidazole-5-carboxamide

CAS Registry Number

360-97-4

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 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-1.1	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

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

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Fibroblasts
Platelet
Skeletal Muscle

Pathways

Name	SMPDB/Pathwhiz	KEGG
Purine Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Skeletal Muscle	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

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

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Adenine phosphoribosyltransferase

General function:: Nucleotide transport and metabolism
Specific function:: Catalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis.
Gene Name:: APRT
Uniprot ID:: Q56JW4
Molecular weight:: 19537.0

Reactions

AICAR + Pyrophosphate → 5-Aminoimidazole-4-carboxamide + Phosphoribosyl pyrophosphate	details

Showing metabocard for 5-Aminoimidazole-4-carboxamide (BMDB0003192)

Structure for BMDB0003192 (5-Aminoimidazole-4-carboxamide)

Enzymes

Reactions