(2R,3R,4S,5R)-2-(6-amino-8-bromo-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 81903
• Molecular Formular: C10H12BrN5O4
• Molecular Mass: 346.13738
• Monoisotopic Mass: 345.00726589
• SMILES: n1([C@H]2[C@@H]([C@H](O)[C@H](O2)CO)O)c(nc2c1ncnc2N)Br
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1c(Br)nc2c1ncnc2N
• InChI: InChI=1S/C10H12BrN5O4/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,13,14)/t3-,5-,6-,9-/m1/s1
• InChIKey: VJUPMOPLUQHMLE-UUOKFMHZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-(6-amino-8-bromo-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: bromoadenosine
• Synonyms: 6-Amino-8-bromopurine riboside; 8-Bromoadenine-9-β-D-ribofuranoside; 8-BROMOADENOSINE; (2R,3R,4S,5R)-2-(6-amino-8-bromo-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol; 8-Bromoadenine-9-β-D-ribofuranoside; 8-Bromoadenosine; 2-(6-amino-8-bromo-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol; 8-溴腺苷

Database IDs

• CAS Number: 2946-39-6
• EC Number: 220-959-0
• MDL Number: MFCD00063773; MFCD00005733
• Beilstein Number: 627737
• PubChem SID: 24891901; 162069022
• PubChem CID: 96544

CALCULATED PROPERTIES

• Acid pKa: 12.452744
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.040446
• LogD (pH = 7.4): -1.0270739
• Log P: -1.0268967
• Molar Refractivity: 70.8204 cm^3
• Polarizability: 27.664213 Å^3
• Polar Surface Area: 139.54 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: white powder
• Melting Point: 210-212 °C (dec.)(lit.); ca 211°C dec.
• Optical Rotation: [α]20/D -33±2°, c = 1% in 1 M HCl; -33 (c=1 in 1N HCl)

Safety Information

• Storage Condition: 0°C
• Storage Warning: Air Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Gene Information: rat ... Adora2a(25369)

Product Information

• Purity: ≥99.0% (HPLC); 98%
• Empirical Formula (Hill Notation): C10H12BrN5O4

DETAILS

MP Biomedicals - 02105471

Crystalline

Sigma Aldrich - B6272

包装
1, 5 g in poly bottle

Sigma Aldrich - 16132

Other Notes
Inhibits the binding of cyclic AMP and adenosine to the activated cyclic AMP/adenosine binding protein1

REFERENCES

• Adenosine binding inhibitor.