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8-Br-cAMP-AM

CAT: 0804-HY-134263Size: 1 EachDry Ice: NoHazardous: No
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CAT#:0804-HY-134263Size:1 Each
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Description
8-Br-cAMP-AM is a cyclic adenosine monophosphate (cAMP) analog that activates two major signal transduction pathways in the heart by mimicking the effects of cAMP: protein kinase A (PKA) and guanosine nucleotide exchange factor (Epac), which is directly activated by cAMP. 8-Br-cAMP-AM can be used to study cardiac ischemia and reperfusion injury[1].
CAS Number
190522-24-8
UNSPSC
12352005
Target
PKA; Ras
Type
Reference compound
Related Pathways
GPCR/G Protein; MAPK/ERK Pathway; Stem Cell/Wnt; TGF-beta/Smad
Applications
Neuroscience-Neuromodulation
Field of Research
Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/8-br-camp-am.html
Smiles
NC1=NC=NC2=C1N=C(Br)N2[C@H]3[C@H](O)[C@H](O4)[C@@H](CO[P@@]4(OCOC(C)=O)=O)O3
Molecular Formula
C13H15BrN5O8P
Molecular Weight
480.16
References & Citations
[1]Khaliulin I, et al. Preconditioning or postconditioning with 8-Br-cAMP-AM protects the heart against regional ischemia and reperfusion: A role for mitochondrial permeability transition[J]. Cells, 2021, 10 (5) : 1223.
Shipping Conditions
Room temperature
Scientific Category
Reference compound1
Clinical Information
No Development Reported

Chemical Information

[(4aR,6R,7R,7aS)-6-(6-amino-8-bromopurin-9-yl)-7-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-2-yl]oxymethyl acetate
CAS Number190522-24-8
PubChem CID172653134
IUPAC Name[(4aR,6R,7R,7aS)-6-(6-amino-8-bromopurin-9-yl)-7-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-2-yl]oxymethyl acetate
Molecular FormulaC13H15BrN5O8P
Molecular Weight480.16
XLogP-1
Topological Polar Surface Area170
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count12
Rotatable Bond Count5
Heavy Atom Count28
Formal Charge0
Complexity662
SMILES
CC(=O)OCOP1(=O)OC[C@@H]2[C@@H](O1)[C@H]([C@@H](O2)N3C4=NC=NC(=C4N=C3Br)N)O
InChI
InChI=1S/C13H15BrN5O8P/c1-5(20)23-4-25-28(22)24-2-6-9(27-28)8(21)12(26-6)19-11-7(18-13(19)14)10(15)16-3-17-11/h3,6,8-9,12,21H,2,4H2,1H3,(H2,15,16,17)/t6-,8-,9-,12-,28?/m1/s1
InChIKey
YPJNHYCRVYPJOT-JFUDBUEBSA-N
Chemical Structure
2D Structure
2D structure of [(4aR,6R,7R,7aS)-6-(6-amino-8-bromopurin-9-yl)-7-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-2-yl]oxymethyl acetate
CAS: 190522-24-8
CID: 172653134
Formula: C13H15BrN5O8P
MW: 480.16
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight480.16
XLogP3-1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count12
Rotatable Bond Count5
Exact Mass478.98416
Monoisotopic Mass478.98416
Topological Polar Surface Area170 Ų
Heavy Atom Count28
Formal Charge0
Complexity662
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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