1H-imidazole-4-carboxamide, 5-amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-

Base Information

• Chemical Name: 1H-imidazole-4-carboxamide, 5-amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-
• CAS No.: 3031-94-5
• Molecular Formula: C9H15N4O8P
• Molecular Weight: 338.214
• Hs Code.: 29349990
• NSC Number: 292227,283955
• DSSTox Substance ID: DTXSID50863081
• Wikidata: Q27165640
• Mol file: 3031-94-5.mol

Synonyms:[5-(5-amino-4-carbamoylimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate;1H-imidazole-4-carboxamide, 5-amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-;Imidazole-4-carboxamide, 5'-(dihydrogen phosphate);C9-H15-N4-O8-P;NSC-283955;NSC-292227;1H-Imidazole-4-carboxamide, 5-amino-1-(5-O-phosphono-.beta.-D-ribofuranosyl)-;SCHEMBL1230589;SCHEMBL20134003;SCHEMBL20276955;CHEBI:93885;DTXSID50863081;Imidazole-4-carboxamide, 5-amino-1-.beta.-D-ribofuranosyl-, 5'-(dihydrogen phosphate);BDBM526262;NSC283955;NSC292227;AKOS030242258;FT-0620013;US11185100, TABLE 14.2;BRD-A67373739-001-01-4;Q27165640;5'-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-D-RIBOFURANOSYL;5-Amino-1-(5-O-phosphonopentofuranosyl)-1H-imidazole-4-carboxamide;[5-(5-amino-4-carbamoyl-1-imidazolyl)-3,4-dihydroxy-2-oxolanyl]methyl dihydrogen phosphate;132069-10-4

Chemical Property of 1H-imidazole-4-carboxamide, 5-amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-

Chemical Property:

• Appearance/Colour: White powder with pink tinge
• Melting Point: 198-202 °C dec.
• Boiling Point: 845.3 °C at 760 mmHg
• PKA: 1.86±0.10(Predicted)
• Flash Point: 465 °C
• PSA: 213.19000
• Density: 2.3 g/cm³
• LogP: -1.42580
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly, Heated, Sonicated), Methanol (Slightly), Water (Slightly)
• XLogP3: -3.8
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 5
• Exact Mass: 338.06275045
• Heavy Atom Count: 22
• Complexity: 475

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5′-monophosphate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C(N1C2C(C(C(O2)COP(=O)(O)O)O)O)N)C(=O)N
• Uses: AICAR monophosphate is a 5′′-phosphorylated analog of cell permeable AICAR that mimics AMP. AICAR is an adenosine monophophate (AMP)-activated protein kinase (AMPK) activator/agonist.

Technology Process of 1H-imidazole-4-carboxamide, 5-amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-

There total 9 articles about 1H-imidazole-4-carboxamide, 5-amino-1-(5-O-phosphono-beta-D-ribofuranosyl)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C27H44N4O9PPolSi2 → 5-aminoimidazole-4-carboxamide ribonucleotide (3031-94-5)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.333333h; solid phase reaction;

DOI:10.1002/ejoc.200901271

Reference yield:

C34H44N6O13PPolSi2 + ethylenediamine (107-15-3,85404-18-8) → N-(2-aminoethyl)formamide (69219-13-2) + N1-(2,4-dinitrophenyl)ethane-1,2-diamine (28767-75-1) + 5-aminoimidazole-4-carboxamide ribonucleotide (3031-94-5)

Guidance literature:

C₃₄H₄₄N₆O₁₃PPolSi₂; ethylenediamine; In N,N-dimethyl-formamide; at 50 ℃; for 8h; solid phase reaction;

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.333333h; solid phase reaction;

DOI:10.1002/ejoc.200901271

Reference yield:

C34H44N6O13PPolSi2 + Trimethylenediamine (109-76-2,54018-94-9) → N-(2,4-dinitrophenyl)-1,3-diaminopropane (23920-00-5) + 5-aminoimidazole-4-carboxamide ribonucleotide (3031-94-5) + N-(2-aminopropyl)formamide (56125-51-0)

Guidance literature:

C₃₄H₄₄N₆O₁₃PPolSi₂; Trimethylenediamine; In N,N-dimethyl-formamide; at 50 ℃; for 8h; solid phase reaction;

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.333333h; solid phase reaction;

DOI:10.1002/ejoc.200901271

upstream raw materials:

AICA riboside

5-Aminoimidazole-4-carboxamide

5-phosphoribosyl-1-pyrophosphate

ethylenediamine

Downstream raw materials:

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

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

Refernces

• 1、 Eltoukhy, Lobna,Loderer, Christoph. "A Multi-enzyme Cascade for the Biosynthesis of AICA Ribonucleoside Di- and Triphosphate". . . Retrieved 2021/12/22.