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Acadesine

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Name

Acadesine

EINECS 220-097-5
CAS No. 2627-69-2 Density 2.06 g/cm3
PSA 156.85000 LogP -1.54280
Solubility >10 mg/mL in water Melting Point 214-215 °C
Formula C9H14N4O5 Boiling Point 726.3 °C at 760 mmHg
Molecular Weight 258.234 Flash Point 393.1 °C
Transport Information N/A Appearance tan powder
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 2627-69-2 (AICAR) Hazard Symbols IrritantXi
Synonyms

Imidazole-4-carboxamide,5-amino-1-b-D-ribofuranosyl- (6CI,7CI,8CI);1-Ribosyl-4-carboxamido-5-aminoimidazole;1-b-D-Ribofuranosyl-5-amino-4-imidazolecarboxamide;5-Amino-1-ribosyl-4-imidazolecarboxamide;5-Amino-1-b-D-ribofuranosylimidazole-4-carboxamide;5-Amino-4-imidazolecarboxamide ribofuranoside;5-Amino-4-imidazolecarboxamideriboside;5-Aminoimidazole-4-carboxamide 1-(b-D-ribofuranoside);AIC-Riboside;AICA-Riboside;Acadesine;Arasine;NSC 105823;GP 1-110;

Article Data 25

Acadesine Synthetic route

197437-76-6

5-amino-1-(5′-O-tert-butyldimethylsilyl-2′,3′-O-isopropylidene-β-D-ribofuranosyl)imidazole-4-carboxamide

2627-69-2

AICA riboside

Conditions
ConditionsYield
With trifluoroacetic acid In acetonitrile at 0 - 20℃; for 17h;78%
659746-61-9

9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1-(2-methoxy-ethoxymethyl)-1,9-dihydro-purin-6-one

2627-69-2

AICA riboside

Conditions
ConditionsYield
With sodium hydroxide for 1h; Heating;73%
Stage #1: 9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1-(2-methoxy-ethoxymethyl)-1,9-dihydro-purin-6-one With sodium hydroxide; water for 1h; Heating / reflux;
Stage #2: With hydrogenchloride In water at 20℃;
70%
23192-64-5

5-amino-1-β-D-ribofuranosyl-1H-imidazole-4-carbonitrile

2627-69-2

AICA riboside

Conditions
ConditionsYield
With sodium hydroxide at 100℃; for 2.5h;72%
129878-03-1

5-azido-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamide

2627-69-2

AICA riboside

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In acetic acid under 760 Torr; for 1.5h; Ambient temperature;42%
With hydrogen; palladium on activated charcoal In water; acetic acid at 23℃; under 760 Torr; for 1h;42%
98880-13-8

5-Amino-1-(β-D-ribofuranosyl)imidazole-4-carboxylic Acid Hydrazide

2627-69-2

AICA riboside

Conditions
ConditionsYield
With ethanol; water; nickel
50730-45-5

5-nitro-1-β-D-ribofuranosyl-1H-imidazole-4-carboxylic acid amide

2627-69-2

AICA riboside

Conditions
ConditionsYield
With water; platinum Hydrogenation;
20735-74-4

5-amino-1-(β-D-ribofuranosyl)imidazole-4-(N-benzyl)carboxamide

2627-69-2

AICA riboside

Conditions
ConditionsYield
With ammonia; sodium amide
7408-41-5

2,3,5-tri-O-benzoyl-β-D-ribofuranosyl azide

2627-69-2

AICA riboside

Conditions
ConditionsYield
With ethyl acetate; platinum Hydrogenation.Behandeln mit -cyan-essigsaeure-amid und metanol. Natriummethylat;
515822-74-9

9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1-methoxymethyl-1,9-dihydro-purin-6-one

2627-69-2

AICA riboside

Conditions
ConditionsYield
With sodium hydroxide Heating;

9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1-ethoxymethyl-1,9-dihydro-purin-6-one

2627-69-2

AICA riboside

Conditions
ConditionsYield
With sodium hydroxide Heating;

Acadesine Specification

The Acadesine, with the CAS registry number 2627-69-2, has the systematic name 5-amino-1-(β-D-ribofuranosyl)-1H-imidazole-4-carboxamide. Its molecular formula is C9H14N4O5 and its product categories are Bases & Related Reagents; Carbohydrates & Derivatives; Nucleotides; Protein Kinase storage Temp. However, keep it at -20 °C.

Other characteristics of the Acadesine can be summarised as followings: (1)ACD/LogP: -3.87; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -3.87; (4)ACD/LogD (pH 7.4): -3.87; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 9; (10)#H bond donors: 7; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 78.29 Å2; (13)Index of Refraction: 1.821; (14)Molar Refractivity: 54.55 cm3; (15)Molar Volume: 125.2 cm3; (16)Polarizability: 21.62×10-24cm3; (17)Surface Tension: 106.5 dyne/cm; (18)Density: 2.06 g/cm3; (19)Flash Point: 393.1 °C; (20)Enthalpy of Vaporization: 111.33 kJ/mol; (21)Boiling Point: 726.3 °C at 760 mmHg; (22)Vapour Pressure: 3.83E-22 mmHg at 25°C.

Uses of this chemical: The Acadesine is the prototype of a new class of compounds termed adenosine regulating agents. It is also an AMP-activated protein kinase activator which is used for the treatment of acute lymphoblastic leukemia and may have applications in treating other disorders such as diabetes.

When you are using this chemical, please be cautious about it as the following: This chemical is irritating to eyes, respiratory system and skin. You should wear suitable protective clothing if you use it. In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure: 
1.SMILES: O=C(c1ncn(c1N)[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO)N
2.InChI: InChI=1/C9H14N4O5/c10-7-4(8(11)17)12-2-13(7)9-6(16)5(15)3(1-14)18-9/h2-3,5-6,9,14-16H,1,10H2,(H2,11,17)/t3-,5-,6-,9-/m1/s1
3.InChIKey: RTRQQBHATOEIAF-UUOKFMHZBE

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