8-Bromoadenosine cyclic 3',5'-monophosphate
Basic information
- CAS
23583-48-4- Standard SMILES
Nc1ncnc2c1nc(Br)n2[C@@H]1O[C@H]2COP(=O)(O)O[C@@H]2[C@H]1O- InChIKey
DVKQVRZMKBDMDH-FULWYAMNSA-N- Molecular formula
- C10H11BrN5O6P
- Average molar mass
- 408.1 g/mol
- Monoisotopic mass
- 406.96303
Names & identifiers
- Preferred name
- 8-Bromoadenosine cyclic 3',5'-monophosphate
- IUPAC
- (4aS,6R,7R,7aR)-6-(6-amino-8-bromopurin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
- English name
- 8-Bromoadenosine 3':5'-cyclic monophosphate
- Molecular formula
- C10H11BrN5O6P
- Molecular weight
- 408.1
Names & synonyms
8-BROMOADENOSINE CYCLIC 3',5'-MONOPHOSPHATECHEMBL1624796SCHEMBL29384358(4aS,6R,7R,7aR)-6-(6-Amino-8-bromo-9H-purin-9-yl)-2,7-dihydroxytetrahydro-2H,4H-2lambda~5~-furo[3,2-d][1,3,2]dioxaphosphinin-2-one8-BR-CAMP8-BROMO-CAMPB-cAMP8-Br-A-3:5-MP8-BR-CAMP,98+%8-Bromocyclic AMPCyclic amp, 8-bromo-CyclicMonophosphate
Show more names
8-Bromo-cyclic 3',5'-amp8-bromo-3',5'-cyclic AMP
Database identifiers
- CAS
23583-48-4- PubChem CID
- 6604063
- DTXSID
DTXSID1040403- ChEMBL
CHEMBL1624796- Nikkaji
- J2.155.881H
Properties
Computed structural properties
- XLogP
- -1.5
- Topological polar surface area
- 155 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 1
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 532
Experimental & physicochemical properties
Endocrine DisruptorsPotential endocrine disrupting compound
Physicochemical properties
- Melting point
- 254 °C · 254 °C (dec.) (lit.)
- Boiling point
- 741.9 · 741.9±70.0 °C(Predicted)
- Density
- 2.8 · 2.80±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- aqueous base: soluble
- pka
- 0.95 · 0.95±0.60(Predicted)
- form
- Powder
- color
- Pale Brown
- Sensitive
- Hygroscopic
- BRN
- 591930 · 591930
- 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)/t3-,5-,6-,9-/m1/s1
- InChIKey
- DVKQVRZMKBDMDH-UUOKFMHZSA-N
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 3-10
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 29349990
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
Uses8-Bromoadenosine 3′,5′-cyclic monophosphate has been used:to treat H295R cells as positive controls for CYP19 inductionas a membrane permeable cAMP analog to study its effect on short-circuit current (Isc)to investigate its potential as an inducer of differentiation in Wharton′s jelly-derived mesenchymal stem cells (WJ-MSCs)
Additional notes
DefinitionChEBI: A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic AMP bearing an additional bromo substituent at position 8 on the adenine ring. An activator of cyclic AMP-dependent protein kinase.
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