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

• ChemBase ID: 155394
• Molecular Formular: C10H14N5O7P
• Molecular Mass: 347.221221
• Monoisotopic Mass: 347.06308444
• SMILES: c1nc(c2c(n1)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)OP(=O)(O)O)N
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)OP(=O)(O)O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(22-23(18,19)20)6(17)4(1-16)21-10/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
• InChIKey: QDFHPFSBQFLLSW-KQYNXXCUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: adenosine 2'-phosphate
• Synonyms: 2′-AMP; 2′-Adenylic acid; Adenosine 2′-monophosphate; 腺苷-2′-磷酸

Database IDs

• MDL Number: MFCD00022827
• PubChem SID: 162249532; 24891443
• PubChem CID: 94136

CALCULATED PROPERTIES

• Acid pKa: 0.68354994
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -4.8893466
• LogD (pH = 7.4): -6.2041807
• Log P: -5.2996483
• Molar Refractivity: 74.0685 cm^3
• Polarizability: 29.089455 Å^3
• Polar Surface Area: 186.07 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

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

• Biological Source: from yeast
• Empirical Formula (Hill Notation): C10H14N5O7P

DETAILS

Sigma Aldrich - A9396

Application
Adenosine 2′-monophosphate (2′-AMP) is a metabolite produced from hydrolysis of 2′,3′-cAMP. 2′-AMP inhibits proliferation of preglomerular vascular smooth muscle cells and glomerular mesangial cells via A2B receptors. 2′-AMP is used in the synthesis of a new photoaffinity lable for the coenzyme site of porcine NADP-specific isocitrate dehydrogenase. 2′,3′-cAMP and 2′-AMP represent a new unexplored pathway for adenosine-based cell regulation.