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

• ChemBase ID: 4002
• Molecular Formular: C14H18N5O11P
• Molecular Mass: 463.293381
• Monoisotopic Mass: 463.07404305
• SMILES: O[C@@H]1[C@@H](COP(=O)(O)O)O[C@H]([C@@H]1O)n1cnc2c(N[C@@H](CC(=O)O)C(=O)O)ncnc12
• Canonical SMILES: OC(=O)C[C@@H](C(=O)O)Nc1ncnc2c1ncn2[C@@H]1O[C@@H]([C@H]([C@H]1O)O)COP(=O)(O)O
• InChI: InChI=1S/C14H18N5O11P/c20-7(21)1-5(14(24)25)18-11-8-12(16-3-15-11)19(4-17-8)13-10(23)9(22)6(30-13)2-29-31(26,27)28/h3-6,9-10,13,22-23H,1-2H2,(H,20,21)(H,24,25)(H,15,16,18)(H2,26,27,28)/t5-,6+,9+,10+,13+/m0/s1
• InChIKey: OFBHPPMPBOJXRT-VWJPMABRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-({9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-9H-purin-6-yl}amino)butanedioic acid
• IUPAC Traditional name: adenylosuccinic acid
• Synonyms: Adenylosuccinic acid; Aspartyl adenylate; Adenylosuccinate; N(6)-(1,2-dicarboxyethyl)AMP; N(6)-(1,2-dicarboxyethyl)-AMP; N-[9-(5-O-phosphono-beta-D-ribofuranosyl)-9H-purin-6-yl]aspartic acid; Adenylosuccinic Acid; 腺苷酸基琥珀酸

Database IDs

• CAS Number: 19046-78-7
• PubChem SID: 24890933; 160967437; 46509168
• PubChem CID: 447145

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.2194421
• H Acceptors: 14
• H Donor: 7
• LogD (pH = 5.5): -7.8843665
• LogD (pH = 7.4): -11.924866
• Log P: -5.1594777
• Molar Refractivity: 96.1758 cm^3
• Polarizability: 37.782154 Å^3
• Polar Surface Area: 246.68 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.96
• LOG S: -2.29
• Solubility (Water): 2.38e+00 g/l

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ~96% (HPLC)
• Empirical Formula (Hill Notation): C14H18N5O11P

DETAILS

DrugBank - DB04418

Drug information: experimental

Sigma Aldrich - A5028

Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A5028.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.