Home > Compound List > Compound details
2627-69-2 molecular structure
click picture or here to close

5-amino-1-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-imidazole-4-carboxamide

ChemBase ID: 160201
Molecular Formular: C9H14N4O5
Molecular Mass: 258.23126
Monoisotopic Mass: 258.09641957
SMILES and InChIs

SMILES:
[C@@H]1(C([C@H](O[C@H]1n1cnc(c1N)C(=O)N)CO)O)O
Canonical SMILES:
OC[C@H]1O[C@H]([C@H](C1O)O)n1cnc(c1N)C(=O)N
InChI:
InChI=1S/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
InChIKey:
RTRQQBHATOEIAF-DTUHVUQASA-N

Cite this record

CBID:160201 http://www.chembase.cn/molecule-160201.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
5-amino-1-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-imidazole-4-carboxamide
IUPAC Traditional name
5-amino-1-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazole-4-carboxamide
Synonyms
5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranoside
AICAR
Acadesine
5-Amino-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamide
5-Amino-4-imidazolecarboxamide Riboside
Arasine
GP 1-110
NSC 105823
5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranoside
CAS Number
2627-69-2
PubChem SID
162254336
PubChem CID
46780289

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
TRC A611700 external link Add to cart
PubChem 46780289 external link
Data Source Data ID Price
TRC
A611700 external link Add to cart Please log in.
Data Source Data ID
PubChem 46780289 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 12.449647  H Acceptors
H Donor LogD (pH = 5.5) -2.6328213 
LogD (pH = 7.4) -2.5593672  Log P -2.5583196 
Molar Refractivity 58.2692 cm3 Polarizability 22.46471 Å3
Polar Surface Area 156.85 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Methanol expand Show data source
Water (65 mg / mL at 23°C) expand Show data source
Apperance
Off-White to Pale Beige Solid expand Show data source
Melting Point
205-207°C (dec.) expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

TRC TRC
Toronto Research Chemicals - A611700 external link
AICAR 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 myocardi

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Mullane, K., et al.: Trends Cardiovasc Med., 3, 227 (1993)
  • • Browne, G.J., et al.: J. Biol. Chem., 279, 13, 12220 (2004)
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle