{[(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

• ChemBase ID: 302376
• Molecular Formular: C10H14N5O7P
• Molecular Mass: 347.221221
• Monoisotopic Mass: 347.06308444
• SMILES: c1nc(c2c(n1)n(cn2)[C@H]1C([C@H]([C@H](O1)COP(=O)(O)O)O)O)N
• Canonical SMILES: OC1[C@@H](O)[C@H](O[C@H]1n1cnc2c1ncnc2N)COP(=O)(O)O
• InChI: InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6+,7?,10-/m1/s1
• InChIKey: UDMBCSSLTHHNCD-PKJMTWSGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: [(2R,3R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
• Synonyms: Adenylic acid; 5'-AMP; Adenosine-5'-monophosphoric acid; 腺苷-5'-单磷酸

Database IDs

• CAS Number: 61-19-8
• EC Number: 200-500-0
• MDL Number: MFCD00149360
• Beilstein Number: 5205540
• Merck Index: 14158

CALCULATED PROPERTIES

• Acid pKa: 1.2246279
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -4.751471
• LogD (pH = 7.4): -5.7464666
• Log P: -5.1917515
• 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

Physical Property

• Melting Point: ca 190°C dec.
• Optical Rotation: -47 (c=2 in 2% NaOH)

Safety Information

• RTECS: AU7480500
• TSCA Listed: 是

Product Information

• Purity: 99% (dry wt.), water <6%