{[5-(6-amino-8-bromo-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

• ChemBase ID: 134260
• Molecular Formular: C10H13BrN5O7P
• Molecular Mass: 426.117281
• Monoisotopic Mass: 424.97359641
• SMILES: c1nc(c2c(n1)n(c(n2)Br)C1C(C(C(O1)COP(=O)(O)O)O)O)N
• Canonical SMILES: OC1C(O)C(OC1n1c(Br)nc2c1ncnc2N)COP(=O)(O)O
• InChI: InChI=1S/C10H13BrN5O7P/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-6(18)5(17)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,17-18H,1H2,(H2,12,13,14)(H2,19,20,21)
• InChIKey: DNPIJKNXFSPNNY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[5-(6-amino-8-bromo-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: C10H13BrN5O7P
• Synonyms: 8-Br-AMP; 8-Bromoadenosine 5′-monophosphate

Database IDs

• CAS Number: 23567-96-6
• MDL Number: MFCD00056945
• PubChem SID: 24891684; 162228537
• PubChem CID: 3525955

CALCULATED PROPERTIES

• Acid pKa: 1.2239963
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -3.6035507
• LogD (pH = 7.4): -4.681145
• Log P: -3.7307093
• Molar Refractivity: 81.6933 cm^3
• Polarizability: 32.28468 Å^3
• Polar Surface Area: 186.07 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

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: ~98%

DETAILS

Sigma Aldrich - B3131

Application
8-Bromoadenosine 5′′-monophosphate (8-Br-AMP) is an analogue of 5’-AMP useful for receptor mapping studies; as a starting structure for 8-modified 5’-AMP derivatives and for synthesis of poly-8-bromoriboadenylic acid.