8-bromo-cAMP

HCID 32014CAS 23583-48-4

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Basic information

Standard SMILES: Nc1ncnc2c1nc(Br)n2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O
InChIKey: DVKQVRZMKBDMDH-UUOKFMHZSA-N
Molecular formula: C10H11BrN5O6P
Average molar mass: 408.1 g/mol
Monoisotopic mass: 406.96303

Names & identifiers

Preferred name: 8-bromo-cAMP
IUPAC: (4aR,6R,7R,7aS)-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-bromo-cAMP23583-48-48-Bromo-cyclic AMP8-Bromo-cyclic 3',5'-AMPCyclic AMP, 8-bromo8-Bromoadenosine cyclic 3',5'-phosphateCyclic 8-bromoadenosine 3',5'-monophosphate8-Bromoadenosine 3',5'-monophosphate8-BROMO CYCLIC ADENOSINE MONOPHOSPHATE5QO1UW05Q5NSC-171719Adenosine, 8-bromo-, cyclic 3',5'-(hydrogen phosphate)

Show more names

8-BR-CAMPB-cAMP8-Br-A-3:5-MP8-BR-CAMP,98+%8-Bromocyclic AMP-CyclicMonophosphate8-bromo-3',5'-cyclic AMP

DTXSID1040403Br Cycl AMP8 Bromo cAMP8 Br Cyclic AMP8-Br Cyclic AMPAMP, Br Cycl8 Bromo Cyclic AMP8-Bromo Cyclic AMP

Database identifiers

CAS: 23583-48-4
PubChem CID: 32014
ChEMBL: CHEMBL1626177
ChEBI: CHEBI:64211
UNII: 5QO1UW05Q5
EC Number: 245-760-6
Nikkaji: J229.011A

Properties

Computed structural properties

XLogP: -1.5
Topological polar surface area: 155 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 10
Rotatable bonds: 1
Heavy atoms: 23
Formal charge: 0
Complexity: 532

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
SMILES: Nc1ncnc2n([C@@H]3O[C@@H]4COP(O)(=O)O[C@H]4[C@H]3O)c(Br)nc12
FDA UNII: 5 QO1UW05Q5 · 5QO1UW05Q5
UNSPSC Code: 41106305 · 41106305
NACRES: 77 · NA.77
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Safety Statements: 22 · 22-24/25
WGK Germany: 3 · 3
F: 3 · 3-10
HS Code: 29349990 · 29349990
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

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 · 1 item

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)

Suppliers38 total

上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]

上海微佳禾生物科技有限公司17502176150; 17502176150 · [email protected]

武汉易泰科技有限公司上海分公司18930552037 · [email protected]

MedBio脉铂医药021-69568360 18916172912 · [email protected]

上海梅凯科技有限公司021-68689288 15300790979 · [email protected]

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.

Related reactions

3 records

New reaction record

HRID 1440957As reactantuspto-grants-1996_03

HRID 1689620As reactantuspto-grants-2012_04

HRID 1723458As reactantuspto-grants-1989_08

Linked notes

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