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

• ChemBase ID: 110021
• Molecular Formular: C10H14N5O7P
• Molecular Mass: 347.221221
• Monoisotopic Mass: 347.06308444
• SMILES: Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](OP(=O)(O)O)[C@H]1O
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1OP(=O)(O)O)O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C10H14N5O7P/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/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
• InChIKey: LNQVTSROQXJCDD-KQYNXXCUSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 84-21-9
• EC Number: 201-521-8
• MDL Number: MFCD00005746
• Beilstein Number: 54478
• PubChem SID: 162095709; 24891429
• PubChem CID: 41211

CALCULATED PROPERTIES

• Acid pKa: 0.86534554
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -4.829373
• LogD (pH = 7.4): -6.054201
• Log P: -5.27431
• 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: ~210 °C (dec.)
• Optical Rotation: [α]20/D -43±2°, c = 0.5% in 0.5 M Na2HPO4

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥97.0% (HPLC)
• Biological Source: from yeast
• Empirical Formula (Hill Notation): C10H14N5O7P
• Classification: Rare Derivatives of Natural Compounds

DETAILS

MP Biomedicals - 05213406

MP Biomedicals Rare Chemical collection

Sigma Aldrich - A9272

Application
Adenosine 3′-monophosphate (3′-AMP) is a metabolite produced from hydrolysis of 2′,3′-cAMP by a family of metal-dependent phosphodiesterases. 3′-AMP inhibits proliferation of preglomerular vascular smooth muscle cells and glomerular mesangial cells via A2B receptors. 2′,3′-cAMP and 3′-AMP represent a new unexplored pathway for adenosine-based cell regulation.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A9272.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 01950

Application
Adenosine 3′-monophosphate (3′-AMP) is a metabolite produced from hydrolysis of 2′,3′-cAMP by a family of metal-dependent phosphodiesterases. 3′-AMP inhibits proliferation of preglomerular vascular smooth muscle cells and glomerular mesangial cells via A2B receptors. 2′,3′-cAMP and 3′-AMP represent a new unexplored pathway for adenosine-based cell regulation.