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

• ChemBase ID: 159570
• Molecular Formular: C20H28N10O14P2
• Molecular Mass: 694.442442
• Monoisotopic Mass: 694.12616889
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1c2c(nc1)c(ncn2)N)CO)OP(=O)(O)O)O.[C@@H]1(C([C@H](O[C@H]1n1c2c(nc1)c(ncn2)N)CO)O)OP(=O)(O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1OP(=O)(O)O)O)n1cnc2c1ncnc2N.OC[C@H]1O[C@H]([C@H](C1O)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
• InChIKey: UQRXDDDXDPEXNS-AGTAMSEFSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162253705
• PubChem CID: 71313041

CALCULATED PROPERTIES

• Acid pKa: 0.86533904
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -4.829372
• LogD (pH = 7.4): -6.054201
• Log P: -5.274322
• 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 - A281775

An adenosine derivative that is a metabolite of adenosine-2’:3’-cyclic monophopshate (A280450).

REFERENCES

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