N⁶,2′-O-Dibutyryladenosine 3′,5′-cyclic monophosphate sodium salt - ≥95%(HPLC), powder , CAS No.16980-89-5

CAS: 16980-89-5 Cat. No.: N464165 Molecular Weight: 491.37 EC Number: 241-059-4

GRADE & PURITY ≥95%(HPLC), powder

Synonyms

Dibutyryl cAMP (sodium salt);DBcAMP (sodium salt) | InChI=1/C6H10O2/c7-6-4-2-1-3-5-8-6/h1-5H | Actosin | Adenosine, N-(1-oxobutyl)-, cyclic 3',5'-(hydrogen phosphate) 2'-butanoate, monosodium salt | Actosin (TN) | STK803270 | EINECS 243-065-2 | MLS0022071

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Description

Dibutyryl CAMP is a cell-permeable CAMP analogue that activates CAMP dependent protein kinase (PKA) or the CAMP/PKA signaling pathway. Dibutyryl CAMP is used as a morphological differentiation inducer and cell signaling modulator in cells such as Schwann cells. Dibutyrl cAMP is used in a variety of differentiation studies, such as neuron differentiation / neuronal differentiation.

Specifications

Synonyms

Dibutyryl cAMP (sodium salt);DBcAMP (sodium salt) | InChI=1/C6H10O2/c7-6-4-2-1-3-5-8-6/h1-5H | Actosin | Adenosine, N-(1-oxobutyl)-, cyclic 3', 5'-(hydrogen phosphate) 2'-butanoate, monosodium salt | Actosin (TN) | STK803270 | EINECS 243-065-2 | MLS0022071

Specifications & Purity

≥95%(HPLC), powder

Biochemical and Physiological Mechanisms

Cell-permeable cAMP analog that activates cAMP dependent protein kinase (PKA).

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.

Action Type

INHIBITOR

Purity

≥95%(HPLC)

Names and Identifiers

• Canonical Smiles: CCCC(=O)NC1=C2C(=NC=N1)N(C=N2)C3C(C4C(O3)COP(=O)(O4)[O-])OC(=O)CCC.[Na+]
• IUPAC Name: sodium;[(4aR,6R,7R,7aR)-6-[6-(butanoylamino)purin-9-yl]-2-oxido-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-yl] butanoate
• InChIKey: KRBZRVBLIUDQNG-JBVYASIDSA-M
• INCHI: 1S/C18H24N5O8P.Na/c1-3-5-11(24)22-16-13-17(20-8-19-16)23(9-21-13)18-15(30-12(25)6-4-2)14-10(29-18)7-28-32(26,27)31-14;/h8-10,14-15,18H,3-7H2,1-2H3,(H,26,27)(H,19,20,22,24);/q;+1/p-1/t10-,14-,15-,18-;/m1./s1
• Isomeric SMILES: CCCC(=O)NC1=C2C(=NC=N1)N(C=N2)[C@H]3[C@@H]([C@H]4[C@H](O3)COP(=O)(O4)[O-])OC(=O)CCC.[Na+]
• WGK Germany: 2
• RTECS: ES5055500
• Molecular Weight: 491.37
• Reaxy-Rn: 38305031
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=38305031&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 Monosaccharide phosphates Purines and purine derivatives N-arylamides Fatty acid esters Organic phosphoric acids and derivatives Fatty amides N-substituted imidazoles Pyrimidines and pyrimidine derivatives Imidolactams Oxolanes Heteroaromatic compounds Carboxylic acid esters Secondary carboxylic acid amides Oxacyclic compounds Azacyclic compounds Monocarboxylic acids and derivatives Organic oxides Organic sodium salts Carbonyl compounds Organic zwitterions Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 3',5'-cyclic purine ribonucleotide - Pentose phosphate - Glycosyl compound - N-glycosyl compound - Monosaccharide phosphate - Imidazopyrimidine - Purine - N-arylamide - Fatty acid ester - Fatty amide - Monosaccharide - N-substituted imidazole - Organic phosphoric acid derivative - Pyrimidine - Imidolactam - Fatty acyl - Imidazole - Heteroaromatic compound - Azole - Oxolane - Carboxylic acid ester - Secondary carboxylic acid amide - Carboxamide group - Azacycle - Organoheterocyclic compound - Oxacycle - Monocarboxylic acid or derivatives - Organic alkali metal salt - Carboxylic acid derivative - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic nitrogen compound - Organic oxygen compound - Organic sodium salt - Organic zwitterion - Organic salt - Carbonyl group - Organonitrogen compound - 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

GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)

Discover Target: GLP1R

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

APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

Discover Target: APEX1

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

GMNN Tbio Geminin (128009 Activities)

Discover Target: GMNN

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

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

microRNA 21 (64692 Activities)

Explore this target

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

Associated Targets(non-human)

Plasmodium falciparum (966862 Activities)

Explore this target

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

Mus musculus (284745 Activities)

Explore this target

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

Npsr1 Neuropeptide S receptor (260 Activities)

Discover Target: Npsr1

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

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: H2O: 100mg/mL
• Sensitivity: Loss of 2 '- O-butyryl at pH 8.5
• Molecular Weight: 491.400 g/mol
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 8
• Exact Mass: 491.118 Da
• Monoisotopic Mass: 491.118 Da
• Topological Polar Surface Area: 167.000 Ų
• Heavy Atom Count: 33
• Formal Charge: 0
• Complexity: 765.000
• 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. Fen Wang, Jinping Zhang, Qian Zhang, Zhangyong Song, Caiyan Xin.  (2024)  Antifungal activities of Equol against Candida albicans in vitro and in vivo.  Virulence,      [PMID:39267283] [10.1080/21505594.2024.2404256]

2. Yaxiu Feng, Xiong Wang, Cien Chen, Di Wang, Changshun Hou, Yiran Wang, Huan Hu, Peiran Chen, LeiYing Qin, Qianya Wan, Xi Yao, Ming-Liang He.  (2025)  Carbon Quantum Dots Assisted Virus Tracking: From Skin to Brain.  ADVANCED MATERIALS,      [PMID:40619836] [10.1002/adma.202508464]