{[(2R,3S,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-[hydroxy(13C)methyl](2,3,4,5-13C4)oxolan-3-yl]oxy}phosphonic acid; {[(2R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-[hydroxy(13C)methyl](2,3,4,5-13C4)oxolan-3-yl]oxy}phosphonic acid

• ChemBase ID: 159571
• Molecular Formular: C20H28N10O14P2
• Molecular Mass: 704.36899038
• Monoisotopic Mass: 704.15971727
• SMILES: [13CH]1(OP(=O)(O)O)[13C@@H]([13CH2]O)O[13C@@H](n2cnc3c2ncnc3N)[13C@H]1O.[13CH]1(O)[13C@@H]([13CH2]O)O[13C@@H](n2cnc3c2ncnc3N)[13C@H]1OP(=O)(O)O
• Canonical SMILES: O[13CH2][13C@H]1O[13C@H]([13C@H]([13CH]1OP(=O)(O)O)O)n1cnc2c1ncnc2N.O[13CH2][13C@H]1O[13C@H]([13C@H]([13CH]1O)OP(=O)(O)O)n1cnc2c1ncnc2N
• InChI: InChI=1S/2C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(17)7(4(1-16)21-10)22-23(18,19)20;11-8-5-9(13-2-12-8)15(3-14-5)10-7(22-23(18,19)20)6(17)4(1-16)21-10/h2*2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6+,7?,10-;4-,6?,7+,10-/m11/s1/i2*1+1,4+1,6+1,7+1,10+1
• InChIKey: UQRXDDDXDPEXNS-SLSIEFPASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-[hydroxy(^1^3C)methyl](2,3,4,5-^1^3C₄)oxolan-3-yl]oxy}phosphonic acid; {[(2R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-[hydroxy(^1^3C)methyl](2,3,4,5-^1^3C₄)oxolan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: [(2R,3S,5R)-2-(6-aminopurin-9-yl)-4-hydroxy-5-[hydroxy(^1^3C)methyl](2,3,4,5-^1^3C₄)oxolan-3-yl]oxyphosphonic acid; [(2R,4S,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[hydroxy(^1^3C)methyl](2,3,4,5-^1^3C₄)oxolan-3-yl]oxyphosphonic acid
• Synonyms: 2’(3')-Adenylic acid-13C5; 2’(3')-AMP-13C5; Adenosine 2’(3')-(Dihydrogen Phosphate)-13C5; Adenosine 2’(3')-Phosphate-13C5; NSC 210570-13C5; Adenosine Monophosphate (mixture of 2'(3')-phosphate isomers)-13C5

Database IDs

• PubChem SID: 162253706
• PubChem CID: 46780089

CALCULATED PROPERTIES

• Acid pKa: 0.86534554
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -4.829373
• LogD (pH = 7.4): -6.054201
• Log P: -5.27431
• Molar Refractivity: 74.0685 cm^3
• Polarizability: 29.089455 Å^3
• Polar Surface Area: 186.07 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A281777

Labelled AMP mixture

REFERENCES

• Jackson, E.K. et al.: Hypertension, 56, 151 (2010)
• Jackson, E.K. et al: J. Bio. Chem., 284, 33097 (2010)