8-(4-Chlorophenylthio)adenosine 3′,5′-cyclic monophosphate sodium salt - ≥99% , CAS No.93882-12-3

CAS: 93882-12-3 Cat. No.: C276526 Molecular Weight: 493.79

GRADE & PURITY ≥99%

Synonyms

8-Cpt-camp | 8-(4-Chlorophenylthio)-cAMP sodium | 8-(4-Chlorophenylthio)-adenosine-3',5'-cyclic monophosphate, sodium salt | Adenosine,8-[(4-chlorophenyl)thio]-,cyclic 3',5'-(hydrogen phosphate),monosodium salt(9ci) | 8-(4-Chlorophenylthio)adenosine 3',5'

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Product Application:

8- (4-thiochlorophenyl) adenosine 3 '5' -cyclic sodium monophosphate is used for:
Up-regulated cellular cholesterol pump (adenosine triphosphate (ATP) binding box (ABC) transporter 1, ABCA-1)
Glucose production assay
Stimulating the cystic fibrosis transmembrane conduction regulatory factor (CFTR) channel in airway epithelial cells

Specifications

Synonyms

8-Cpt-camp | 8-(4-Chlorophenylthio)-cAMP sodium | 8-(4-Chlorophenylthio)-adenosine-3', 5'-cyclic monophosphate, sodium salt | Adenosine, 8-[(4-chlorophenyl)thio]-, cyclic 3', 5'-(hydrogen phosphate), monosodium salt(9ci) | 8-(4-Chlorophenylthio)adenosine 3', 5'

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

Membrane permeability cAMP analogues. Used as a selective activator of CAMP-dependent protein kinase (PKA). Inhibition of CGMP-dependent phosphodiesterase and CAMP-dependent phosphodiesterase at higher concentrations. Inhibits the hydrolysis and secretion

Storage

Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

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

Action Type

INHIBITOR

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 504769580
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504769580
• Canonical Smiles: C1C2C(C(C(O2)N3C4=NC=NC(=C4N=C3SC5=CC=C(C=C5)Cl)N)O)OP(=O)(O1)[O-].[Na+]
• IUPAC Name: sodium;(4aR,6R,7R,7aS)-6-[6-amino-8-(4-chlorophenyl)sulfanylpurin-9-yl]-2-oxido-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
• InChIKey: YIJFVHMIFGLKQL-DNBRLMRSSA-M
• INCHI: 1S/C16H15ClN5O6PS.Na/c17-7-1-3-8(4-2-7)30-16-21-10-13(18)19-6-20-14(10)22(16)15-11(23)12-9(27-15)5-26-29(24,25)28-12;/h1-4,6,9,11-12,15,23H,5H2,(H,24,25)(H2,18,19,20);/q;+1/p-1/t9-,11-,12-,15-;/m1./s1
• Isomeric SMILES: C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C4=NC=NC(=C4N=C3SC5=CC=C(C=C5)Cl)N)O)OP(=O)(O1)[O-].[Na+]
• Molecular Weight: 493.79
• Reaxy-Rn: 26050921
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=26050921&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 Diarylthioethers Glycosylamines 6-aminopurines Monosaccharide phosphates Thiophenol ethers Aminopyrimidines and derivatives Chlorobenzenes Aryl chlorides Organic phosphoric acids and derivatives Imidolactams N-substituted imidazoles Oxolanes Heteroaromatic compounds Secondary alcohols Sulfenyl compounds Oxacyclic compounds Azacyclic compounds Organic metal halides Organic zwitterions Organochlorides Organic sodium salts Organic oxides Hydrocarbon derivatives Primary amines
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 3',5'-cyclic purine ribonucleotide - Pentose phosphate - Glycosyl compound - N-glycosyl compound - Diarylthioether - 6-aminopurine - Monosaccharide phosphate - Purine - Imidazopyrimidine - Aryl thioether - Thiophenol ether - Aminopyrimidine - Chlorobenzene - Halobenzene - Imidolactam - Benzenoid - Monosaccharide - N-substituted imidazole - Monocyclic benzene moiety - Organic phosphoric acid derivative - Aryl halide - Pyrimidine - Aryl chloride - Azole - Heteroaromatic compound - Imidazole - Oxolane - Secondary alcohol - Organic metal halide - Oxacycle - Azacycle - Organic alkali metal salt - Organoheterocyclic compound - Sulfenyl compound - Thioether - Primary amine - Alcohol - Organic sodium salt - Organosulfur compound - Amine - Organooxygen compound - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Organic salt - Organic zwitterion - Organohalogen compound - Organic oxide - Organochloride - 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)

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in H2O: 25 mg/mL
• Sensitivity: Moisture sensitive
• Molecular Weight: 493.800 g/mol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 3
• Exact Mass: 492.999 Da
• Monoisotopic Mass: 492.999 Da
• Topological Polar Surface Area: 183.000 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 699.000
• 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