Faicar

Base Information

• Chemical Name: Faicar
• CAS No.: 13018-54-7
• Molecular Formula: C10H15 N4 O9 P
• Molecular Weight: 366.22
• UNII: KNY2D67FT5
• DSSTox Substance ID: DTXSID50156384
• Nikkaji Number: J602.393B
• Wikipedia: 5-Formamidoimidazole-4-carboxamide_ribotide
• Wikidata: Q2817110
• Pharos Ligand ID: XG7QPCFZHG6T
• Metabolomics Workbench ID: 37801
• ChEMBL ID: CHEMBL521310
• Mol file: 13018-54-7.mol

Synonyms:5-formamidoimidazole-4-carboxamide ribotide;FAICAR

Chemical Property of Faicar

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 941.6°Cat760mmHg
• Flash Point: 523.2°C
• PSA: 219.76000
• Density: 2.17g/cm³
• LogP: -1.37140
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Water (Slightly)
• XLogP3: -4
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 366.05766507
• Heavy Atom Count: 24
• Complexity: 531

Purity/Quality:

99%, ^*data from raw suppliers

FAICAR~85% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C(N1C2C(C(C(O2)COP(=O)(O)O)O)O)NC=O)C(=O)N
• Isomeric SMILES: C1=NC(=C(N1[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O)NC=O)C(=O)N
• Uses: FAICAR is the derivative of AICAR (A611700), which is a nucleoside analogue that is able to enter nucleoside pools and is able to significantly increase levels of adenosine during periods of ATP breakdown. Adenosine-regulating agents (ARAs) have been recognized for therapeutic potential in myocardial ischemia. Cardioprotective.

Technology Process of Faicar

There total 3 articles about Faicar 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: 100.0%

formic acid (64-18-6) + 5-aminoimidazole-4-carboxamide ribonucleotide (3031-94-5) → 5-aminoformylimidazole-4-carboxamide 1-β-D-ribofuranosyl 5'-monophosphate (13018-54-7)

Guidance literature:

With sodium formate; acetic anhydride; at 20 - 50 ℃; for 0.5h;

DOI:10.1021/jacs.9b00241

Reference yield:

5-aminoimidazole-4-carboxamide ribonucleotide (3031-94-5) + N10-formyl-dihydrofolic acid → 5-aminoformylimidazole-4-carboxamide 1-β-D-ribofuranosyl 5'-monophosphate (13018-54-7) + (S)-2-{4-[(2-Amino-4-oxo-3,4,7,8-tetrahydro-pteridin-6-ylmethyl)-amino]-benzoylamino}-pentanedioic acid (4033-27-6)

Guidance literature:

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

DOI:10.1021/ja010014k

Reference yield:

formic acid (64-18-6) → 5-aminoformylimidazole-4-carboxamide 1-β-D-ribofuranosyl 5'-monophosphate (13018-54-7)

Guidance literature:

With sodium formate; acetic anhydride;

upstream raw materials:

formic acid

5-aminoimidazole-4-carboxamide ribonucleotide

Refernces

• 1、 Wang, Shao-An,Ko, Yeonjin,Zeng, Jia,Geng, Yujie,Ren, Daan,Ogasawara, Yasushi,Irani, Seema,Zhang, Yan,Liu, Hung-Wen. "Identification of the Formycin A Biosynthetic Gene Cluster from Streptomyces kaniharaensis Illustrates the Interplay between Biological Pyrazolopyrimidine Formation and de Novo Purine Biosynthesis". . p. 6127 - 6131. Retrieved 2019.