8-Bromoadenosine
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Basic information
- CAS
2946-39-6- Standard SMILES
Nc1ncnc2c1nc(Br)n2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O- InChIKey
VJUPMOPLUQHMLE-UUOKFMHZSA-N- Molecular formula
- C10H12BrN5O4
- Average molar mass
- 346.14 g/mol
- Monoisotopic mass
- 345.00726596
Overview
8-Bromoadenosine is a purine nucleoside.
Names & identifiers
- Preferred name
- 8-Bromoadenosine
- IUPAC
- (2R,3R,4S,5R)-2-(6-amino-8-bromopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
- English name
- 8-Bromoadenosine
- Molecular formula
- C10H12BrN5O4
- Molecular weight
- 346.14
Names & synonyms
8-Bromoadenosine2946-39-685C9T4TXH2NSC-79213(2R,3R,4S,5R)-2-(6-amino-8-bromo-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diolDTXSID001021364RefChem:106966DTXCID101506408220-959-0Adenosine, 8-bromo-(2R,3R,4S,5R)-2-(6-Amino-8-bromo-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diolBromoadenosine
Show more names
8-Br-A8-Br-Ar8-Br-Adenosine8-BROMO-D-ADENOSINE8-Bromoadenosine,98%8-BROMOADENOSINE USP/EP/BP
8-Bromo AdenosineMFCD000057336-Amino-8-bromopurine riboside8-Bromo-adenosineNSC 79213UNII-85C9T4TXH2CHEBI:2312CHEMBL1775009
Database identifiers
- CAS
2946-39-6- PubChem CID
- 96544
- DTXSID
DTXSID001021364- ChEMBL
CHEMBL1775009- ChEBI
CHEBI:2312- UNII
- 85C9T4TXH2
- EC Number
- 220-959-0
- Nikkaji
- J136.591F
Properties
Computed structural propertiesFilling in
- XLogP
- 0
- Topological polar surface area
- 140 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 2
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 367
Physicochemical properties
- Melting point
- 210 · 210-212 °C (dec.)(lit.)
- Boiling point
- 717.7 · 717.7±70.0 °C(Predicted)
- Density
- 1.8171 · 1.8171 (rough estimate)
- refractive index
- 1.64 · 1.6400 (estimate)
- storage temp.
- -20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
- solubility
- DMSO (Slightly), Methanol (Slightly, Sonicated)
- pka
- 12.89 · 12.89±0.70(Predicted)
- form
- powder
- color
- white
- Water Solubility
- Soluble in DMSO, and DMF. Insoluble in water.
- Sensitive
- Air Sensitive
- BRN
- 627737 · 627737
- CAS DataBase Reference
- 2946 · 2946-39-6(CAS DataBase Reference)
- FDA UNII
- 85 C9T4TXH2 · 85C9T4TXH2
- Symbol(GHS)
- 7 · GHS07
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- F
- 10-23
- wgk
- 3
- hs_code
- 2934 99 90
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36-24/25-22
- Hazard statements
- H315-H319
- Precautionary statements
- P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Chemistry & industry
Applications
Description8-Bromoadenosine is a nucleotide that is structurally related to adenosine. It can be used as an inhibitor of guanine nucleotide-binding proteins and has shown biological properties in vitro. 8-Bromoadenosine has been shown to inhibit the mitochondrial membrane potential, cytosolic Ca2+, and the synthesis of RNA and protein. 8-Bromoadenosine also inhibits leukemia inhibitory factor (LIF) production by 3T3-L1 preadipocytes and induces apoptosis in T84 cells.
Uses8-Bromoadenosine is an adenosine binding inhibitor. formation of 8-S-L-cysteinyladenosine from 8-Bromoadenosine and cysteine.
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: 8-Bromoadenosine is a purine nucleoside.
Related reactions
8 records
Compound notes
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