• Name

  5'-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-D-RIBOFURANOSYL 5'-MONOPHOSPHATE

• EINECS 221-212-1
• CAS No. 3031-94-5
• Article Data15
• CAS DataBase
• Density 2.3 g/cm³
• Solubility
• Melting Point 198-202 °C dec.
• Formula C₉H₁₅N₄O₈P
• Boiling Point 845.3 °C at 760 mmHg
• Molecular Weight 338.214
• Flash Point 465 °C
• Transport Information
• Appearance White powder with pink tinge
• Safety 24/25
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms 5-Amino-4-imidazolecarboxamideribotide;5-Amino-4-imidazolecarboxamide ribonucleotide;Imidazole-4-carboxamide,5-amino-1-b-D-ribofuranosyl-, 5'-(dihydrogenphosphate) (8CI);Imidazole-4-carboxamide, 5-amino-1-b-D-ribofuranosyl-, 5'-phosphate(6CI,7CI);5-Amino-1-(5-O-phosphono-b-D-ribofuranosyl)-1H-imidazole-4-carboxamide;5-Amino-1-(5'-phosphofuranoribosyl)-4-imidazolecarboxamide;5'-Phosphoribosyl-5-amino-4-imidazolecarboxamide;5'-Phospho-b-D-ribosyl-5-amino-4-imidazolecarboxamide;AICA Ribotide;AICAR;Acadesine 5'-monophosphate;NSC283955;NSC 292227;ZMP;
• PSA 213.19000
• LogP -1.42580

Synthetic route

2627-69-2

AICA riboside

3031-94-5

5-aminoimidazole-4-carboxamide ribonucleotide

Conditions

Conditions	Yield
With enzyme-extracts from pigeon's liver; ATP
With brewer's yeast-autolysate; ATP

360-97-4

5-Aminoimidazole-4-carboxamide

97-55-2, 7540-64-9, 99945-37-6, 130384-52-0

5-phosphoribosyl-1-pyrophosphate

3031-94-5

5-aminoimidazole-4-carboxamide ribonucleotide

Conditions

Conditions	Yield
With nucleoside-phosphorus ylase

C34H44N6O13PPolSi2

107-15-3

ethylenediamine

A

69219-13-2

N-(2-aminoethyl)formamide

B

28767-75-1

N1-(2,4-dinitrophenyl)ethane-1,2-diamine

C

3031-94-5

5-aminoimidazole-4-carboxamide ribonucleotide

Conditions

Conditions	Yield
Stage #1: C34H44N6O13PPolSi2; ethylenediamine In N,N-dimethyl-formamide at 50℃; for 8h; solid phase reaction; Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 0.333333h; solid phase reaction;

...Expand

C34H44N6O13PPolSi2

109-76-2

Trimethylenediamine

A

23920-00-5

N-(2,4-dinitrophenyl)-1,3-diaminopropane

B

3031-94-5

5-aminoimidazole-4-carboxamide ribonucleotide

C

56125-51-0

N-(2-aminopropyl)formamide

Conditions

Conditions	Yield
Stage #1: C34H44N6O13PPolSi2; Trimethylenediamine In N,N-dimethyl-formamide at 50℃; for 8h; solid phase reaction; Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 0.333333h; solid phase reaction;

...Expand

C27H44N4O9PPolSi2

3031-94-5

5-aminoimidazole-4-carboxamide ribonucleotide

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 0.333333h; solid phase reaction;	18 mg

64-18-6

formic acid

3031-94-5

5-aminoimidazole-4-carboxamide ribonucleotide

13018-54-7

5-aminoformylimidazole-4-carboxamide 1-β-D-ribofuranosyl 5'-monophosphate

Conditions

Conditions	Yield
With sodium formate; acetic anhydride at 20 - 50℃; for 0.5h;	100%

3031-94-5

5-aminoimidazole-4-carboxamide ribonucleotide

530-62-1

1,1'-carbonyldiimidazole

Imidazol-1-yl-phosphonic acid mono-[(2R,3S,4R,5R)-5-(5-amino-4-carbamoyl-imidazol-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 3h;

3031-94-5

5-aminoimidazole-4-carboxamide ribonucleotide

N10-formyl-dihydrofolic acid

A

13018-54-7

5-aminoformylimidazole-4-carboxamide 1-β-D-ribofuranosyl 5'-monophosphate

B

4033-27-6

(S)-2-{4-[(2-Amino-4-oxo-3,4,7,8-tetrahydro-pteridin-6-ylmethyl)-amino]-benzoylamino}-pentanedioic acid

Conditions

Conditions	Yield
With Dimethylarsinic acid; AICAR transformylase wild type; ethanolamine; Tris buffer at 25℃; pH=7.5; Enzyme kinetics; Further Variations:; Reagents; pH-values;

...Expand

3031-94-5

5-aminoimidazole-4-carboxamide ribonucleotide

917-08-8

diphosphoric acid-1-adenosin-5'-yl ester-2-[(1R)-1-(5-amino-4-carbamoyl-imidazol-1-yl)-D-1,4-anhydro-ribitol-5-yl ester]

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylformamide / 3 h 2: tri-n-butylamine / dimethylformamide / 48 h / Ambient temperature View Scheme

108-24-7

acetic anhydride

3031-94-5

5-aminoimidazole-4-carboxamide ribonucleotide

5-formamido-4-imidazolecarboxamide ribonucleotide

Conditions

Conditions	Yield
With formic acid; sodium hydroxide In aq. phosphate buffer at 37℃; for 1h; pH=7.4;