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

• ChemBase ID: 153304
• Molecular Formular: C10H16N5O8P
• Molecular Mass: 365.236501
• Monoisotopic Mass: 365.07364913
• SMILES: c1nc(c2c(n1)n(cn2)C1C(C(C(O1)COP(=O)(O)O)O)O)N.O
• Canonical SMILES: OC1C(O)C(OC1n1cnc2c1ncnc2N)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
• InChIKey: ZOEFQKVADUBYKV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid hydrate
• IUPAC Traditional name: hydrate vidarabine phosphate
• Synonyms: 5′-AMP; A-5′-P; AMP; 5′-Adenylic acid; Adenosine 5′-monophosphate monohydrate; 5′-腺苷酸; 腺苷-5'-单磷酸 一水合物

Database IDs

• CAS Number: 18422-05-4
• MDL Number: MFCD00005750
• Beilstein Number: 54612
• PubChem SID: 24890610; 24890637; 162247443
• PubChem CID: 16218864

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

• Solubility: H2O: soluble (with addition of mild alkali)

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥97%; ≥99%
• Biological Source: from yeast
• Empirical Formula (Hill Notation): C10H14N5O7P · H2O

DETAILS

Sigma Aldrich - A2252

Packaging
5, 25, 100 g in poly bottle
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).