(2S)-2-({5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-imidazol-4-yl}formamido)butanedioic acid

• ChemBase ID: 177841
• Molecular Formular: C13H18N4O9
• Molecular Mass: 374.30342
• Monoisotopic Mass: 374.10737818
• SMILES: Nc1c(C(=O)N[C@@H](CC(=O)O)C(=O)O)ncn1[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc(c1N)C(=O)N[C@H](C(=O)O)CC(=O)O
• InChI: InChI=1S/C13H18N4O9/c14-10-7(11(23)16-4(13(24)25)1-6(19)20)15-3-17(10)12-9(22)8(21)5(2-18)26-12/h3-5,8-9,12,18,21-22H,1-2,14H2,(H,16,23)(H,19,20)(H,24,25)/t4-,5+,8+,9+,12+/m0/s1
• InChIKey: XNKLTOHYNRQCLJ-ZZZDFHIKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-({5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-imidazol-4-yl}formamido)butanedioic acid
• IUPAC Traditional name: (2S)-2-({5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazol-4-yl}formamido)butanedioic acid
• Synonyms: N-[(5-Amino-1-β-D-ribofuranosyl-1H-imidazol-4-yl)carbonyl]-L-aspartic Acid; SAICAR; N-Succinyl-5-aminoimidazole-4-carboxamide Ribose

Database IDs

• CAS Number: 17388-80-6
• PubChem SID: 164233751
• PubChem CID: 54478644

CALCULATED PROPERTIES

• Acid pKa: 2.9902277
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): -5.571317
• LogD (pH = 7.4): -8.740803
• Log P: -4.2013297
• Molar Refractivity: 79.7798 cm^3
• Polarizability: 31.150492 Å^3
• Polar Surface Area: 217.46 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - S688790

A metabolite of Purine. Purine metabolism by adenylosuccinasedeficient. Since adenosine is a potent inhibitor of neuronal function, depressing the release of several excitatory transmitters and causing direct hyperpolarization of neurons, it was possible

REFERENCES

• Gollub, E.G., et al.: J. Bacteriol., 78, 320 (1959)
• Srivastava, P.C., et al.: J. Med. Chem., 17, 1207 (1959)