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8-BROMOADENOSINE-3',5'-CYCLIC MONOPHOSPHATE SODIUM SALT structure
8-BROMOADENOSINE-3',5'-CYCLIC MONOPHOSPHATE SODIUM SALT structure

8-BROMOADENOSINE-3',5'-CYCLIC MONOPHOSPHATE SODIUM SALT

Iupac Name:(4aR,6R,7R,7aS)-6-(6-amino-8-bromopurin-9-yl)-2-oxido-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
CAS No.: 76939-46-3
Molecular Weight:407.09
Modify Date.: 2022-11-22 20:03
Introduction:

8-Bromo-cAMP sodium salt (8-Br-Camp sodium salt), a cyclic AMP analog, is an activator of cyclic AMP-dependent protein kinase (PKA)[1].


A long-acting derivative of cyclic AMP. It is an activator of cyclic AMP-dependent protein kinase, but resistant to degradation by cyclic AMP phosphodiesterase.

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1. Names and Identifiers
1.1 Name
8-BROMOADENOSINE-3',5'-CYCLIC MONOPHOSPHATE SODIUM SALT
1.2 Synonyms

4H-Furo[3,2-d]-1,3,2-dioxaphosphorin-7-ol, 6-(6-amino-8-bromo-9H-purin-9-yl)tetrahydro-2-hydroxy-, 2-oxide, sodium salt, (4aR,6R,7R,7aS)- (1:1) 8-BR-CAMP NA 8-BR-CAMP SODIUM SALT 8-BROM-ADENOSIN-3',5'-CYCLOPHOSPHAT 8-Bromoadenosine 3',5'-phosphoric acid sodium salt 8-BROMOADENOSINE 3':5'-CYCLIC MONOPHOSPHATE SODIUM SALT 8-bromoadenosine 3:5-cyclic*monophosphate sodiu 8-BROMOADENOSINE 3':5'-CYCLICMONOPHOSPHA TE SODIUM 8-BROMOADENOSINE-3',5'-CYCLOPHOSPHATE SODIUM SALT 8-bromoadenosine-3’,5’-cyclicmonophosphate(8-br-camp),sodiumsalt 8-BROMO-CAMP, NA 8-BROMO-CAMP, SODIUM SALT 8-BROMO-CAMP,NA 8-BROMO-CAMP,SODIUM SALT ADENOSINE 3',5'-CYCLIC MONOPHOSPHATE, 8-BROMO-, SODIUM SALT CAMP, 8-BR, NA CAMP,8-BR,NA MFCD00005844 Sodium (4aR,6R,7R,7aS)-6-(6-amino-8-bromo-9H-purin-9-yl)-7-hydroxytetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-2-olate 2-oxide

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1.3 CAS No.
76939-46-3
1.4 CID
71434121
1.5 Molecular Formula
C10H10BrN5O6P- (isomer)
1.6 Inchi
InChI=1S/C10H11BrN5O6P/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-5(17)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,17H,1H2,(H,18,19)(H2,12,13,14)/p-1/t3-,5-,6-,9-/m1/s1
1.7 InChIkey
DVKQVRZMKBDMDH-UUOKFMHZSA-M
1.8 Canonical Smiles
C1C2C(C(C(O2)N3C4=NC=NC(=C4N=C3Br)N)O)OP(=O)(O1)[O-]
1.9 Isomers Smiles
C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C4=NC=NC(=C4N=C3Br)N)O)OP(=O)(O1)[O-]
2. Properties
2.1 Precise Quality
405.95521
2.1 PSA
167.48000
2.1 logP
0.96450
2.1 Solubility
H2O: 100?mg/mL
2.2 Appearance
off-white powder
2.3 Chemical Properties
Off-white powder
2.4 Color/Form
off-white
2.5 Water Solubility
H2O: 100?mg/mL
2.6 StorageTemp
-20°C
3. Safety and Handling
3.1 Risk Statements
22-24/25
3.1 Safety Statements
22-24/25
3.1 RIDADR
NONH for all modes of transport
3.1 WGK Germany
3
4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s) no data available
Signal word

no data available

Hazard statement(s)

no data available

Precautionary statement(s)
Prevention

no data available

Response

no data available

Storage

no data available

Disposal

no data available

2.3 Other hazards which do not result in classification

no data available

5. Other Information
5.0 Mesh Entry Terms
8 Br Cyclic AMP
5.1 BRN
7739743
5.2 Target
Value
5.3 PKA ()
0.05 μM(Ka)
5.4 Chemical Properties
Off-white powder
5.5 Uses
8-Bromoadenosine 3′,5′-cyclic monophosphate sodium salt has been used:
  • to study its effect on fas and caspase-3 mRNA expression and on P4 production in bovine mid luteal cell culture
  • used to treat choriocarcinoma BeWo cell line and study its effect on cell viability, apoptosis and morphological changes in the nuclei
  • in superfusion medium for head kidneys stimulation

6. Computational chemical data
  • Molecular Weight: 407.09g/mol
  • Molecular Formula: C10H10BrN5O6P-
  • Compound Is Canonicalized: True
  • XLogP3-AA: -1.6
  • Exact Mass: 405.95521
  • Monoisotopic Mass: 405.95521
  • Complexity: 524
  • Rotatable Bond Count: 1
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 10
  • Topological Polar Surface Area: 158
  • Heavy Atom Count: 23
  • Defined Atom Stereocenter Count: 4
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADccBzuAIAEAAAAAAAAAAAAAAAAWJAAAAsSAAAAAAAAFgB+AAAHgBQCCAAGBzhlwYF8L9MFxCgQQZhZICAgC0REKABUCAoVBCDWAJAyEAeRAgPAALTACDwMAIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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