(2R)-2-({9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-yl}amino)butanedioic acid

• ChemBase ID: 177844
• Molecular Formular: C14H17N5O8
• Molecular Mass: 383.31348
• Monoisotopic Mass: 383.10771253
• SMILES: n1cnc2c(c1N[C@H](CC(=O)O)C(=O)O)ncn2[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)n1cnc2c1ncnc2N[C@@H](C(=O)O)CC(=O)O
• InChI: InChI=1S/C14H17N5O8/c20-2-6-9(23)10(24)13(27-6)19-4-17-8-11(15-3-16-12(8)19)18-5(14(25)26)1-7(21)22/h3-6,9-10,13,20,23-24H,1-2H2,(H,21,22)(H,25,26)(H,15,16,18)/t5-,6-,9-,10-,13-/m1/s1
• InChIKey: VKGZCEJTCKHMRL-KFRZGLEESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-({9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-yl}amino)butanedioic acid
• IUPAC Traditional name: (2R)-2-({9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl}amino)butanedioic acid
• Synonyms: N-(9-β-D-Ribofuranosyl-9H-purin-6-yl)-L-aspartic Acid; 6-(1,2-Dicarboxyethylamino)-9-β-D-ribofuranosylpurine; (S)-N-(1,2-Dicarboxyethyl)adenosine; Succinoadenosine; N6-Succinyl Adenosine

Database IDs

• CAS Number: 4542-23-8
• PubChem SID: 164233754
• PubChem CID: 71752227

CALCULATED PROPERTIES

• Acid pKa: 3.138852
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -5.3287115
• LogD (pH = 7.4): -8.270796
• Log P: -4.058436
• Molar Refractivity: 85.3029 cm^3
• Polarizability: 33.19867 Å^3
• Polar Surface Area: 200.15 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - S688825

Succinyladenosine (S-Ado) is a biochemical marker of adenylosuccinase deficiency - the genetic defect of purine de novo synthesis. S-Ado has been previously reported as normally undetectable in cerebrospinal fluid (CSF) of children not suffering from thi

REFERENCES

• Wevers, R., et al.: Clin. Chem., 41, 744 (1995)
• Nassogne, M., et al.: Brain Dev., 22, 383 (1995)
• Jurecka, A., et al.: Mol. Genet., 94, 435 (1995)