[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl 4-(fluorosulfonyl)benzoate hydrochloride

• ChemBase ID: 132605
• Molecular Formular: C17H17ClFN5O7S
• Molecular Mass: 489.8625832
• Monoisotopic Mass: 489.05212481
• SMILES: c1cc(ccc1C(=O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2N)O)O)S(=O)(=O)F.Cl
• Canonical SMILES: O[C@@H]1[C@@H](COC(=O)c2ccc(cc2)S(=O)(=O)F)O[C@H]([C@@H]1O)n1cnc2c1ncnc2N.Cl
• InChI: InChI=1S/C17H16FN5O7S.ClH/c18-31(27,28)9-3-1-8(2-4-9)17(26)29-5-10-12(24)13(25)16(30-10)23-7-22-11-14(19)20-6-21-15(11)23;/h1-4,6-7,10,12-13,16,24-25H,5H2,(H2,19,20,21);1H/t10-,12-,13-,16-;/m1./s1
• InChIKey: ZUHVYHQVJYIHPN-KHXPSBENSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl 4-(fluorosulfonyl)benzoate hydrochloride
• IUPAC Traditional name: [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl 4-(fluorosulfonyl)benzoate hydrochloride
• Synonyms: Adenosine-5′-(4-fluorosulfonylbenzoate) hydrochloride; FSBA; 5′-(4-Fluorosulfonylbenzoyl)adenosine hydrochloride

Database IDs

• CAS Number: 78859-42-4
• MDL Number: MFCD00043258
• Beilstein Number: 8178939
• PubChem SID: 162226882; 24894988
• PubChem CID: 133128

CALCULATED PROPERTIES

• Acid pKa: 12.456743
• H Acceptors: 10
• H Donor: 3
• LogD (pH = 5.5): -0.052105885
• LogD (pH = 7.4): 0.061383788
• Log P: 0.063049756
• Molar Refractivity: 102.5768 cm^3
• Polarizability: 40.13058 Å^3
• Polar Surface Area: 179.75 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: methanol: soluble50 mg/mL, clear, slightly yellow

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

• Purity: ≥95.0% (HPLC)
• Empirical Formula (Hill Notation): C17H16FN5O7S · HCl

DETAILS

Sigma Aldrich - F9128

Quality
Contains one mole dimethylformamide of crystallization
Application
5′-(4-Fluorosulfonylbenzoyl)adenosine (FSBA) is an ATP analog used to study the mechanism of action of wortmannin. FSBA has been used to study vesicular transport in intestinal cells such as Caco-2, and to covalently modify residues in the nucleotide-binding domains (NBDs) of various ATPases, kinases, and other proteins.

Sigma Aldrich - 47502

Other Notes
For the affinity labeling of adenine nucleotide sites in proteins. Review1