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Cyclic AMP

CAT: 0804-HY-B1511-04Size: 10 gDry Ice: NoHazardous: No
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CAT#:0804-HY-B1511-04Size:10 g
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Description
Cyclic AMP (Cyclic adenosine monophosphate), adenosine triphosphate derivative, is an intracellular signaling molecule responsible for directing cellular responses to extracellular signals. Cyclic AMP is an important second messenger in many biological processes[1][2][3].
CAS Number
60-92-4
Product Name Alternative
Cyclic adenosine monophosphate; Adenosine cyclic 3', 5'-monophosphate; cAMP
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Endogenous Metabolite
Type
Natural Products
Related Pathways
Metabolic Enzyme/Protease
Applications
Metabolism-protein/nucleotide metabolism
Field of Research
Cancer; Metabolic Disease; Neurological Disease
Assay Protocol
https://www.medchemexpress.com/cAMP.html
Purity
99.95
Solubility
0.1 M NaOH : 50 mg/mL (ultrasonic; adjust pH to 6 with NaOH)
Smiles
NC1=C2N=CN([C@@H]3O[C@]4([H])COP(O)(O[C@@]4([H])[C@H]3O)=O)C2=NC=N1
Molecular Formula
C10H12N5O6P
Molecular Weight
329.21
Precautions
H302, H315, H319, H335
References & Citations
[1]G M Fimia, et al. Cyclic AMP signaling. J Cell Sci. 2001 Jun;114 (Pt 11) :1971-2.|[2]Paolo Sassone-Corsi, et al. The cyclic AMP pathway. Cold Spring Harb Perspect Biol. 2012 Dec 1;4 (12) :a011148.|[3]Aronoff DM, et, al. Short communication: differences between macrophages and dendritic cells in the cyclic AMP-dependent regulation of lipopolysaccharide-induced cytokine and chemokine synthesis. J Interferon Cytokine Res. 2006 Nov;26 (11) :827-33.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C, 3 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
Human Endogenous Metabolite; Microbial Metabolite

Chemical Information

Camp

3',5'-cyclic AMP is a 3',5'-cyclic purine nucleotide having having adenine as the nucleobase. It has a role as a mouse metabolite, an Escherichia coli metabolite and a human metabolite. It is a 3',5'-cyclic purine nucleotide and an adenyl ribonucleotide. It is a conjugate acid of a 3',5'-cyclic AMP(1-).

CAS Number60-92-4
PubChem CID6076
IUPAC Name(4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
Molecular FormulaC10H12N5O6P
Molecular Weight329.21
XLogP-2.6
Topological Polar Surface Area155
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count10
Rotatable Bond Count1
Heavy Atom Count22
Formal Charge0
Complexity498
SMILES
C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C(N=CN=C43)N)O)OP(=O)(O1)O
InChI
InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
InChIKey
IVOMOUWHDPKRLL-KQYNXXCUSA-N
Chemical Structure
2D Structure
2D structure of Camp
CAS: 60-92-4
CID: 6076
Formula: C10H12N5O6P
MW: 329.21
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight329.21
XLogP3-2.6
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count10
Rotatable Bond Count1
Exact Mass329.05252012
Monoisotopic Mass329.05252012
Topological Polar Surface Area155 Ų
Heavy Atom Count22
Formal Charge0
Complexity498
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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