ChemFOnt: Showing chemical card for 5-Phosphoribosyl-4-carboxy-5-aminoimidazole (CFc000042836)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:45:33 UTC

Chemfont ID

CFc000042836

Molecule Identification

Common Name

5-Phosphoribosyl-4-carboxy-5-aminoimidazole

Definition

5-Phosphoribosyl-4-carboxy-5-aminoimidazole is also known as AICA Ribonucleotide, (D-ribofuranosyl)-isomer or AICAR. 5-Phosphoribosyl-4-carboxy-5-aminoimidazole is considered to be slightly soluble (in water) and acidic

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-Amino-1-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-1H-imidazole-4-carboxylate	HMDB
4-Carboxy-5-aminoimidazole ribotide	HMDB
5'-Phosphoribosyl-5-amino-4-imidazolecarboxamide	HMDB
5-Amino-1-beta-D-ribofuranosylimidazole-4-carboxamide monophosphate	HMDB
5-Amino-4-imidazolecarboxamide ribofuranoside 5'-monophosphate	HMDB
AICA Ribonucleotide	HMDB
AICA Ribonucleotide, (D-ribofuranosyl)-isomer	HMDB
AICAR	HMDB
AICAriboside 5'-monophosphate	HMDB
Aminoimidazole carboxamide ribonucleotide	HMDB
Z-Nucleotide	HMDB
ZMP	HMDB

Chemical Formula

C₉H₁₄N₃O₉P

Average Molecular Weight

339.197

Monoisotopic Molecular Weight

339.046766041

IUPAC Name

5-amino-1-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-1H-imidazole-4-carboxylic acid

Traditional Name

5-amino-1-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}imidazole-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

NC1=C(N=CN1C1OC(COP(O)(O)=O)C(O)C1O)C(O)=O

InChI Identifier

InChI=1S/C9H14N3O9P/c10-7-4(9(15)16)11-2-12(7)8-6(14)5(13)3(21-8)1-20-22(17,18)19/h2-3,5-6,8,13-14H,1,10H2,(H,15,16)(H2,17,18,19)

InChI Key

XFVULMDJZXYMSG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentose phosphates

Alternative Parents

Substituents

Pentose phosphate
Pentose-5-phosphate
Imidazole ribonucleoside
N-glycosyl compound
Glycosyl compound
Monosaccharide phosphate
Monoalkyl phosphate
Imidazole-4-carbonyl group
Alkyl phosphate
Phosphoric acid ester
Aminoimidazole
Organic phosphoric acid derivative
N-substituted imidazole
Azole
Vinylogous amide
Tetrahydrofuran
Imidazole
Heteroaromatic compound
1,2-diol
Secondary alcohol
Amino acid
Amino acid or derivatives
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organopnictogen compound
Organic oxide
Primary amine
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0062424)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.81 g/L	ALOGPS
logP	-2	ALOGPS
logP	-3.7	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.18	ChemAxon
pKa (Strongest Basic)	7.11	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	197.59 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	67.32 m³·mol⁻¹	ChemAxon
Polarizability	28.19 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0062424

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

985

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1010

PDB ID

Not Available

ChEBI ID

185031

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 5-Phosphoribosyl-4-carboxy-5-aminoimidazole (CFc000042836)

MOL for CFc000042836 (5-Phosphoribosyl-4-carboxy-5-aminoimidazole)

3D MOL for CFc000042836 (5-Phosphoribosyl-4-carboxy-5-aminoimidazole)

3D SDF for CFc000042836 (5-Phosphoribosyl-4-carboxy-5-aminoimidazole)

3D-SDF for CFc000042836 (5-Phosphoribosyl-4-carboxy-5-aminoimidazole)

PDB for CFc000042836 (5-Phosphoribosyl-4-carboxy-5-aminoimidazole)

3D PDB for CFc000042836 (5-Phosphoribosyl-4-carboxy-5-aminoimidazole)

SMILES for CFc000042836 (5-Phosphoribosyl-4-carboxy-5-aminoimidazole)

INCHI for CFc000042836 (5-Phosphoribosyl-4-carboxy-5-aminoimidazole)

Structure for CFc000042836 (5-Phosphoribosyl-4-carboxy-5-aminoimidazole)

3D Structure for CFc000042836 (5-Phosphoribosyl-4-carboxy-5-aminoimidazole)