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2D Structure
Also known as: Aicar, Nsc 105823, Schembl2619704, Akos030228468, 5-amino-1-((2r,3s,4r,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1h-imidazole-4-carboxamide
Molecular Formula
C9H14N4O5
Molecular Weight
258.23  g/mol
InChI Key
RTRQQBHATOEIAF-DTUHVUQASA-N

AICAR is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-amino-1-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazole-4-carboxamide
2.1.2 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
2.1.3 InChI Key
RTRQQBHATOEIAF-DTUHVUQASA-N
2.1.4 Canonical SMILES
C1=NC(=C(N1C2C(C(C(O2)CO)O)O)N)C(=O)N
2.1.5 Isomeric SMILES
C1=NC(=C(N1[C@H]2[C@H](C([C@H](O2)CO)O)O)N)C(=O)N
2.2 Synonyms
2.2.1 MeSH Synonyms

1. 4-carboxy-5-aminoimidazole Ribotide

2. 5'-phosphoribosyl-5-amino-4-imidazolecarboxamide

3. 5-amino-1-beta-d-ribofuranosylimidazole-4-carboxamide Monophosphate

4. 5-amino-4-imidazolecarboxamide Ribofuranoside 5'-monophosphate

5. Aica Ribonucleotide

6. Aica Ribonucleotide, (d-ribofuranosyl)-isomer

7. Aicar

8. Aicariboside 5'-monophosphate

9. Aminoimidazole Carboxamide Ribonucleotide

10. Z-nucleotide

11. Zmp

2.2.2 Depositor-Supplied Synonyms

1. Aicar

2. Nsc 105823

3. Schembl2619704

4. Akos030228468

5. 5-amino-1-((2r,3s,4r,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1h-imidazole-4-carboxamide

2.3 Create Date
2010-07-26
3 Chemical and Physical Properties
Molecular Weight 258.23 g/mol
Molecular Formula C9H14N4O5
XLogP3-2.2
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count7
Rotatable Bond Count3
Exact Mass258.09641956 g/mol
Monoisotopic Mass258.09641956 g/mol
Topological Polar Surface Area157 Ų
Heavy Atom Count18
Formal Charge0
Complexity330
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Hypoglycemic Agents

Substances which lower blood glucose levels. (See all compounds classified as Hypoglycemic Agents.)