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add semisystematic name
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| ImageFile1 = 8-bromoadenosine-cyclic-monophosphate-3D-balls.png |
| ImageFile1 = 8-bromoadenosine-cyclic-monophosphate-3D-balls.png |
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| ImageName1 = Ball-and-stick model |
| ImageName1 = Ball-and-stick model |
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| IUPACName = 8-Bromoadenosine 3′,5′-(hydrogen phosphate) |
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| IUPACName = (1''S'',6''R'',8''R'',9''R'')-8-(6-amino-8-bromopurin-9-yl)-3-hydroxy-3-oxo-2,4,7-trioxa-3λ<sup>5</sup>-phosphabicyclo[4.3.0]nonan-9-ol |
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| SystematicName = (4a''R'',6''R'',7''R'',7a''S'')-6-(6-Amino-8-bromo-9''H''-purin-9-yl)-2,7-dihydroxytetrahydro-2''H'',4''H''-2λ<sup>5</sup>-furo[3,2-''d''][1,3,2]dioxaphosphinin-2-one |
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| OtherNames = 8-Br-cAMP; BCAMP; 8-Bromo-cyclic AMP; 8-Bromo-cyclic 3',5'-AMP |
| OtherNames = 8-Br-cAMP; BCAMP; 8-Bromo-cyclic AMP; 8-Bromo-cyclic 3',5'-AMP |
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|Section1={{Chembox Identifiers |
|Section1={{Chembox Identifiers |
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| ChEBI = 64211 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 85519 |
| ChEMBL = 85519 |
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| ChemSpiderID = 29689 |
| ChemSpiderID = 29689 |
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| SMILES = Brc2nc1c(ncnc1n2[C@@H]3O[C@@H]4COP(=O)(O[C@H]4[C@H]3O)O)N |
| SMILES = Brc2nc1c(ncnc1n2[C@@H]3O[C@@H]4COP(=O)(O[C@H]4[C@H]3O)O)N |
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| InChI = 1/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 |
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| InChIKey = DVKQVRZMKBDMDH-UUOKFMHZBM |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 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 |
| StdInChI = 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 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 23583-48-4 |
| CASNo = 23583-48-4 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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⚫ | |||
| UNII = 5QO1UW05Q5 |
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⚫ | |||
|Section2={{Chembox Properties |
|Section2={{Chembox Properties |
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| C=10 | H=11 | Br=1 | N=5 | O=6 | P=1 |
| C=10 | H=11 | Br=1 | N=5 | O=6 | P=1 |
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[[Category:Nucleotides]] |
[[Category:Nucleotides]] |
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[[Category: |
[[Category:Bromoarenes]] |
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[[Category:Purines]] |
[[Category:Purines]] |
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[[Category:Oxygen heterocycles]] |
[[Category:Oxygen heterocycles]] |
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Names | |
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IUPAC name
8-Bromoadenosine 3′,5′-(hydrogen phosphate) | |
Systematic IUPAC name
(4aR,6R,7R,7aS)-6-(6-Amino-8-bromo-9H-purin-9-yl)-2,7-dihydroxytetrahydro-2H,4H-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-2-one | |
Other names
8-Br-cAMP; BCAMP; 8-Bromo-cyclic AMP; 8-Bromo-cyclic 3',5'-AMP | |
Identifiers | |
3D model (JSmol) |
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ChEBI | |
ChEMBL | |
ChemSpider |
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ECHA InfoCard | 100.041.585 ![]() |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C10H11BrN5O6P | |
Molar mass | 408.105 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
8-Bromoadenosine 3',5'-cyclic adenosine monophosphate (8-Br-cAMP) is a brominated derivative of cyclic adenosine monophosphate (cAMP). 8-Br-cAMP is an activator of cyclic AMP-dependent protein kinase, and it is long-acting because it is resistant to degradation by cyclic AMP phosphodiesterase.[2]