ChemFOnt: Showing chemical card for 5-Aminoimidazole-4-carboxamide (CFc000001798)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:31 UTC

Chemfont ID

CFc000001798

Molecule Identification

Common Name

5-Aminoimidazole-4-carboxamide

Definition

5-Aminoimidazole-4-carboxamide is an imidazole derivative which is a metabolite of the antineoplastic agents BIC and DIC. By itself, or as the ribonucleotide, it is used as a condensation agent in the preparation of nucleosides and nucleotides. Compounded with orotic acid, it is used to treat liver diseases. -- Pubchem.

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 )

Functional Ontology

Physiological effect

Health effect

Cancer

Sarcoma (HMDB: HMDB0003192)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 7172404)

Cell

Fibroblast

Fibroblast (HMDB: HMDB0003192)

Fibroblasts (HMDB: HMDB0003192)

Hematocyte

Platelet (HMDB: HMDB0003192)

Tissue substructure

Muscle (HMDB: HMDB0003192)

Excreta

Biofluid or Excreta

Urine (PMID: 30817767)

Tissue

Muscle tissue

Skeletal muscle (HMDB: HMDB0003192)
Skeletal muscle (HMDB: HMDB0003192)

Cellular substructure

Cytoplasm (HMDB: HMDB0003192)
Extracellular (HMDB: HMDB0003192)

Source

Exogenous

Exogenous (HMDB: HMDB0003192)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0003192)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

AICA-Ribosiduria (HMDB: HMDB0003192)
Xanthinuria Type II (PathBank: SMP0120578)
Gout or Kelley-Seegmiller Syndrome (PathBank: SMP0120709)
Xanthine Dehydrogenase Deficiency (Xanthinuria) (PathBank: SMP0120717)
Mitochondrial DNA Depletion Syndrome (PathBank: SMP0120820)
Adenylosuccinate Lyase Deficiency (PathBank: SMP0120670)
Purine Nucleoside Phosphorylase Deficiency (PathBank: SMP0120756)
Adenine Phosphoribosyltransferase Deficiency (APRT) (PathBank: SMP0120819)
Myoadenylate Deaminase Deficiency (PathBank: SMP0120821)
Adenosine Deaminase Deficiency (PathBank: SMP0120448)
Lesch-Nyhan Syndrome (LNS) (PathBank: SMP0120508)
Molybdenum Cofactor Deficiency (PathBank: SMP0120752)
Xanthinuria Type I (PathBank: SMP0120577)
Mitochondrial DNA Depletion Syndrome (PathBank: SMP0000536)

Drug action pathway

Thioguanine Action Pathway (HMDB: HMDB0003192)
Azathioprine Action Pathway (PathBank: SMP0000427)
Mercaptopurine Action Pathway (PathBank: SMP0000428)
Thioguanine Action Pathway (PathBank: SMP0000430)

Metabolic pathway

Purine Metabolism (PathBank: SMP0063668)
Histidine Biosynthesis (PathBank: SMP0121286)
Secondary Metabolites: Histidine Biosynthesis (PathBank: SMP0121334)
Purine Metabolism (HMDB: HMDB0003192)

Melanoma (HMDB: HMDB0003192)

Role

Not Available

Physical Properties

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