Bovine Metabolome Database: Showing metabocard for AICAR (BMDB0001517)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:47:05 UTC

Update Date

2020-05-21 16:27:08 UTC

BMDB ID

BMDB0001517

Secondary Accession Numbers

BMDB01517

Metabolite Identification

Common Name

AICAR

Description

AICAR, also known as Z-nucleotide or ZMP, 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. AICAR is a strong basic compound (based on its pKa). AICAR exists in all living species, ranging from bacteria to humans. Within cattle, AICAR participates in a number of enzymatic reactions. In particular, fumaric acid and AICAR can be biosynthesized from SAICAR through the action of the enzyme adenylosuccinate lyase. In addition, 10-formyltetrahydrofolate and AICAR can be converted into tetrahydrofolic acid and phosphoribosyl formamidocarboxamide through its interaction with the enzyme bifunctional purine biosynthesis protein purh. In cattle, AICAR is involved in the metabolic pathway called the purine metabolism pathway.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide	ChEBI
5'-Phospho-ribosyl-5-amino-4-imidazole carboxamide	ChEBI
5'-Phosphoribosyl-5-amino-4-imidazolecarboxamide	ChEBI
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide	ChEBI
5-Aminoimidazole-4-carboxamide ribotide	ChEBI
5-Phosphoribosyl-4-carbamoyl-5-aminoimidazole	ChEBI
Acadesine 5'-monophosphate	ChEBI
AICA-Ribonucleotide	ChEBI
5-Amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide	Kegg
Acadesine 5'-monophosphoric acid	Generator
5-Amino-1-(5-phospho-b-D-ribosyl)imidazole-4-carboxamide	Generator
5-Amino-1-(5-phospho-β-D-ribosyl)imidazole-4-carboxamide	Generator
5'-p-Ribosyl-5-amino-4-imidazole carboxamide	HMDB
5'-Phosphoribosyl-5-amino-4-imidazole carboxamide	HMDB
5-Amino-4-imidazolecarboxamide ribotide	HMDB
AICA Ribonucleotide	HMDB
Aminoimidazole carboxamide ribonucleotide	HMDB
Z-Nucleotide	HMDB
4-Carboxy-5-aminoimidazole ribotide	HMDB
5-Amino-1-beta-D-ribofuranosylimidazole-4-carboxamide monophosphate	HMDB
5-Amino-4-imidazolecarboxamide ribofuranoside 5'-monophosphate	HMDB
AICA Ribonucleotide, (D-ribofuranosyl)-isomer	HMDB
AICAriboside 5'-monophosphate	HMDB
CAIR	HMDB
ZMP	HMDB
(2R,3S,4R,5R)-5-(4-Carbam0yl-5-aminoimidazol-1-yl)-3,4-dihydroxyoxolan-2-yljmethyl dihydrogen phosphate	HMDB
5'-Phospho-beta-D-ribosyl-5-amino-4-imidazolecarboxamide	HMDB
5'-Phospho-β-D-ribosyl-5-amino-4-imidazolecarboxamide	HMDB
5-Amino-1-(5'-phosphofuranoribosyl)-4-imidazolecarboxamide	HMDB
5-Amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-1H-imidazole-4-carboxamide	HMDB
5-Amino-1-(5-O-phosphono-β-D-ribofuranosyl)-1H-imidazole-4-carboxamide	HMDB
5-Amino-1-(5’-phosphofuranoribosyl)-4-imidazolecarboxamide	HMDB
5-Amino-1beta-D-ribofuranosylimidazole-4-carboxamide 5'-phosphate	HMDB
5-Amino-1β-D-ribofuranosylimidazole-4-carboxamide 5'-phosphate	HMDB
5-Amino-1β-D-ribofuranosylimidazole-4-carboxamide 5’-phosphate	HMDB
5-Amino-4-imidazolecarboxamide ribonucleoside 5'-monophosphate	HMDB
5-Amino-4-imidazolecarboxamide ribonucleoside 5’-monophosphate	HMDB
5-Amino-4-imidazolecarboxamide ribonucleotide	HMDB
5-Amino-4-imidazolecarboxamide riboside 5'-monophosphate	HMDB
5-Amino-4-imidazolecarboxamide riboside 5’-monophosphate	HMDB
5-Aminoimidazole-4-carboxamide ribonucleotide	HMDB
5-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranosyl 5'-monophosphate	HMDB
5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5’-monophosphate	HMDB
5’-Phospho-β-D-ribosyl-5-amino-4-imidazolecarboxamide	HMDB
5’-Phosphoribosyl-5-amino-4-imidazolecarboxamide	HMDB
AICA Ribotide	HMDB
AICAR	HMDB
AICAR (5-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranosyl 5'-monophosphate)	HMDB
AICAR (5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5'-monophosphate)	HMDB
AICAR (5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5’-monophosphate)	HMDB
Acadesine 5’-monophosphate	HMDB
Aminoimidazolecarboxamide ribonucleotide	HMDB

Chemical Formula

C₉H₁₅N₄O₈P

Average Molecular Weight

338.2112

Monoisotopic Molecular Weight

338.062749988

IUPAC Name

{[(2R,3S,4R,5R)-5-(5-amino-4-carbamoyl-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

Traditional Name

aica ribonucleotide

CAS Registry Number

3031-94-5

SMILES

NC(=O)C1=C(N)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O

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)/t3-,5-,6-,9-/m1/s1

InChI Key

NOTGFIUVDGNKRI-UUOKFMHZSA-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

1-(phosphoribosyl)imidazolecarboxamide (CHEBI:18406 )
aminoimidazole (CHEBI:18406 )

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	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.2	ALOGPS
logP	-4.8	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	4.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	203.38 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	69.14 m³·mol⁻¹	ChemAxon
Polarizability	28.57 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Skeletal Muscle

Pathways

Name	SMPDB/Pathwhiz	KEGG
Purine Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	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

HMDB0001517

DrugBank ID

DB01700

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

18406

References

Synthesis Reference

Schmitt, Laurent; Caperelli, Carol A. Enantiospecific synthesis of carbocyclic aminoimidazole carboxamide ribonucleotide (C-AICAR), succinoaminoimidazole carboxamide ribonucleotide (C-SAICAR), and a new intermediate for SAICAR analogs. Nucleosides & Nucleotides (1995), 14(9 & 10), 1929-45.

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

Enzyme Details

2. Bifunctional purine biosynthesis protein PURH

General function:: Nucleotide transport and metabolism
Specific function:: Bifunctional enzyme that catalyzes 2 steps in purine biosynthesis.
Gene Name:: ATIC
Uniprot ID:: Q0VCK0
Molecular weight:: 64483.0

Reactions

N10-Formyl-THF + AICAR → Tetrahydrofolic acid + Phosphoribosyl formamidocarboxamide	details

Enzyme Details

3. Adenylosuccinate lyase

General function:: Nucleotide transport and metabolism
Specific function:: Catalyzes two non-sequential steps in de novo AMP synthesis: converts (S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinate (SAICAR) to fumarate plus 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide, and thereby also contributes to de novo IMP synthesis, and converts succinyladenosine monophosphate (SAMP) to AMP and fumarate.
Gene Name:: ADSL
Uniprot ID:: A3KN12
Molecular weight:: 55484.0

Reactions

SAICAR → Fumaric acid + AICAR	details

Showing metabocard for AICAR (BMDB0001517)

Structure for BMDB0001517 (AICAR)

Enzymes

Reactions

Reactions

Reactions