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

• ChemBase ID: 119794
• Molecular Formular: C10H16N5O8P
• Molecular Mass: 365.236501
• Monoisotopic Mass: 365.07364913
• SMILES: n1([C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O)c2c(nc1)c(ncn2)N.O
• Canonical SMILES: O[C@@H]1[C@H](O)[C@H](O[C@H]1n1cnc2c1ncnc2N)COP(=O)(O)O.O
• InChI: InChI=1S/C10H14N5O7P.H2O/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);1H2/t4-,6-,7-,10-;/m1./s1
• InChIKey: ZOEFQKVADUBYKV-MCDZGGTQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid hydrate
• IUPAC Traditional name: adenylate hydrate
• Synonyms: ((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate hydrate; 5′-AMP; AMP; Adenylic acid from muscle; (-)-Adenosine 5′-monophosphate monohydrate; 肌肉腺苷酸; (-)-腺苷-5'-单磷酸 一水合物

Database IDs

• CAS Number: 18422-05-4
• MDL Number: MFCD00149360
• Beilstein Number: 54612
• PubChem SID: 162107918
• PubChem CID: 6419976

CALCULATED PROPERTIES

• Acid pKa: 1.2246295
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -4.7514725
• LogD (pH = 7.4): -5.7464666
• Log P: -5.1917415
• 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: 183-188 °C (dec.)(lit.)
• Optical Rotation: [α]20/D -48±1°, c = 2% in 2% NaOH; [α]22/D -46.6°, c = 2 in 2% NaOH

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (HPLC); 99%
• Salt Data: H2O
• Empirical Formula (Hill Notation): C10H14N5O7P · H2O
• Classification: Genuine Natural Compounds

DETAILS

Sigma Aldrich - 01970

Application
Adenosine 5′-monophosphate (5′-AMP) has many uses in nature. 5′-AMP is an activator of a class of protein kinases known as AMP-activated protein kinase (AMPK).