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

• ChemBase ID: 133623
• Molecular Formular: C10H15BrN5NaO13P3
• Molecular Mass: 609.066853
• Monoisotopic Mass: 607.89602674
• SMILES: c1nc(c2c(n1)n(c(n2)Br)C1C(C(C(O1)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O)O)N.[Na]
• Canonical SMILES: OC1C(COP(=O)(OP(=O)(OP(=O)(O)O)O)O)OC(C1O)n1c(Br)nc2c1ncnc2N.[Na]
• InChI: InChI=1S/C10H15BrN5O13P3.Na/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-6(18)5(17)3(27-9)1-26-31(22,23)29-32(24,25)28-30(19,20)21;/h2-3,5-6,9,17-18H,1H2,(H,22,23)(H,24,25)(H2,12,13,14)(H2,19,20,21)
• InChIKey: ZKMCUMNNTIIFSK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({[({[5-(6-amino-8-bromo-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid sodium
• IUPAC Traditional name: ({[5-(6-amino-8-bromopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid sodium
• Synonyms: 8-Br-ATP; 8-Bromoadenosine 5′-triphosphate sodium salt

Database IDs

• CAS Number: 81035-56-5
• MDL Number: MFCD00070102
• PubChem SID: 162227900; 24891733
• PubChem CID: 16219027

CALCULATED PROPERTIES

• Acid pKa: 0.8949739
• H Acceptors: 14
• H Donor: 7
• LogD (pH = 5.5): -8.682248
• LogD (pH = 7.4): -9.40448
• Log P: -4.773558
• Molar Refractivity: 103.4391 cm^3
• Polarizability: 41.908104 Å^3
• Polar Surface Area: 279.13 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 23/24/25-36/37/38
• Safety Statements: 22-26-36-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H315-H319-H331-H335
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (HPLC)

DETAILS

Sigma Aldrich - B3756

Biochem/physiol Actions
P2X purinoceptor agonist similar in reactivity to ATP.
Linkage
8-Bromo form of adenosine 5′-triphosphate.
Application
8-Bromoadenosine 5′-triphosphate (8-Br-ATP) is as an ATP analogue used in conjunction with other ATP analogues to study and resolve ATP-site binding effects on receptor and enzyme function and specificity.