Adenosine 3',5'-Cyclic Monophosphate Sodium Salt Hydrate - ≥99% , CAS No.37839-81-9

CAS: 37839-81-9 Cat. No.: A122959 Molecular Weight: 351.19(as Anhydrous) Beilstein Registry Number: 54612

GRADE & PURITY ≥99%

Synonyms

Camp sodium salt | c-AMP sodium salt | cAMP-Na | AC-32412 | MLS001333136 | (4aR,6R,7R,7aS)-6-(6-Amino-9H-purin-9-yl)-2,7-dihydroxytetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinine 2-oxide, sodium salt | Cyclic AMP Sodium Salt | NCGC00179131-02 | sodium (4a

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Adenosine 3′,5′-cyclic monophosphate sodium salt is a naturally-occurring activator of PKA (cAMP-dependent protein kinase A). Cyclic-AMP is an important second messenger that is linked in many systems to neurotransmitter- or hormone-induced receptor stimulation. The cAMP/PKA signaling pathway has shown to induce differentiation, inhibit cell proliferation, and lead to apoptosis. Adenosine 3′,5′-cyclic monophosphate sodium salt monohydrate is an activator of Epac.
Adenosine-3′,5′-cyclic monophosphate (cAMP) is an activator of cyclic-AMP-dependent protein kinase A (PKA). The cAMP/PKA signaling pathway has been shown to inhibit cell proliferation, induce differentiation and lead to apoptosis. Exogneous cAMP plays a role in the spontaneous activity and contraction of the heart muscle.

Specifications

Synonyms

Camp sodium salt | c-AMP sodium salt | cAMP-Na | AC-32412 | MLS001333136 | (4aR, 6R, 7R, 7aS)-6-(6-Amino-9H-purin-9-yl)-2, 7-dihydroxytetrahydro-4H-furo[3, 2-d][1, 3, 2]dioxaphosphinine 2-oxide, sodium salt | Cyclic AMP Sodium Salt | NCGC00179131-02 | sodium (4a

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

Naturally-occurring activator of cyclic-AMP-dependent protein kinase (PKA). cAMP is an important second messenger that is linked in many systems to neurotransmitter- or hormone-induced receptor stimulation. The cAMP/PKA signaling pathway has been shown to

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 488200444
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488200444
• Canonical Smiles: C1C2C(C(C(O2)N3C=NC4=C(N=CN=C43)N)O)OP(=O)(O1)[O-].[Na+]
• IUPAC Name: sodium;(4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2-oxido-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
• InChIKey: BXJBFCKTIWRKMQ-MCDZGGTQSA-M
• INCHI: 1S/C10H12N5O6P.Na/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);/q;+1/p-1/t4-,6-,7-,10-;/m1./s1
• Isomeric SMILES: C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C(N=CN=C43)N)O)OP(=O)(O1)[O-].[Na+]
• WGK Germany: 2
• RTECS: AU7357900
• Molecular Weight: 351.19(as Anhydrous)
• Beilstein: 54612
• Reaxy-Rn: 26171620
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=26171620&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Class Purine nucleotides
      • Subclass Cyclic purine nucleotides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Class: Purine nucleotides
• Subclass: Cyclic purine nucleotides
• Intermediate Tree Nodes: Not available
• Direct Parent: 3',5'-cyclic purine nucleotides
• Alternative Parents: Pentose phosphates Glycosylamines 6-aminopurines Monosaccharide phosphates Aminopyrimidines and derivatives Organic phosphoric acids and derivatives Imidolactams N-substituted imidazoles Oxolanes Heteroaromatic compounds Secondary alcohols Oxacyclic compounds Azacyclic compounds Organic sodium salts Organic zwitterions Primary amines Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 3',5'-cyclic purine ribonucleotide - Pentose phosphate - Glycosyl compound - N-glycosyl compound - 6-aminopurine - Monosaccharide phosphate - Imidazopyrimidine - Purine - Aminopyrimidine - Monosaccharide - N-substituted imidazole - Organic phosphoric acid derivative - Imidolactam - Pyrimidine - Azole - Heteroaromatic compound - Imidazole - Oxolane - Secondary alcohol - Oxacycle - Azacycle - Organoheterocyclic compound - Organic alkali metal salt - Amine - Organic sodium salt - Organonitrogen compound - Organooxygen compound - Alcohol - Organic oxygen compound - Hydrocarbon derivative - Organic nitrogen compound - Organic oxide - Organic salt - Primary amine - Organic zwitterion - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 3',5'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C3 and C5 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

AVPR1B Tclin Vasopressin V1b receptor (1301 Activities)

Discover Target: AVPR1B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PRKAR1A Tbio cAMP-dependent protein kinase type I-alpha regulatory subunit (18 Activities)

Discover Target: PRKAR1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PRKAR2A Tchem cAMP-dependent protein kinase type II-alpha regulatory subunit (246 Activities)

Discover Target: PRKAR2A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GNAS Tbio Guanine nucleotide-binding protein G(s), subunit alpha (103405 Activities)

Discover Target: GNAS

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GMNN Tbio Geminin (128009 Activities)

Discover Target: GMNN

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RXFP1 Tchem Relaxin receptor 1 (6345 Activities)

Discover Target: RXFP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RXFP2 Tbio Relaxin receptor 2 (377 Activities)

Discover Target: RXFP2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ATAD5 Tbio ATPase family AAA domain-containing protein 5 (122566 Activities)

Discover Target: ATAD5

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RAPGEF3 Tchem Rap guanine nucleotide exchange factor 3 (15528 Activities)

Discover Target: RAPGEF3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RAPGEF4 Tchem Rap guanine nucleotide exchange factor 4 (11476 Activities)

Discover Target: RAPGEF4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Plasmodium falciparum (966862 Activities)

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Mus musculus (284745 Activities)

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Hcn2 Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 (15 Activities)

Discover Target: Hcn2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cnga2 Cyclic nucleotide-gated olfactory channel (5 Activities)

Discover Target: Cnga2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Heat sensitive
• Molecular Weight: 351.190 g/mol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 1
• Exact Mass: 351.034 Da
• Monoisotopic Mass: 351.034 Da
• Topological Polar Surface Area: 158.000 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 504.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3

References

1. Liling Wang, Huan Wang, Jing Luo, Ting Xie, Gil Mor, Aihua Liao.  (2022)  Decorin promotes decidual M1-like macrophage polarization via mitochondrial dysfunction resulting in recurrent pregnancy loss.  Theranostics,      [PMID:36438479] [10.7150/thno.78467]

2. Mingfang Wang, Jia Zeng, Binbin Cui, Guangliang Wu, Xiayu Chen, Yikai Fu, Bing Gu, Yinyue Deng.  (2025)  Multilevel regulation of c-di-GMP biosynthesis by cAMP signaling increases Shigella sonnei fitness and pathogenicity in response to bile salts.  Cell Reports,      [PMID:40966079] [10.1016/j.celrep.2025.116306]