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Sp-5,6-DCl-cBIMPS

CAT: 0804-HY-137638Size: 1 EachDry Ice: NoHazardous: No
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Description
Sp-5,6-DCl-cBIMPS is a potent and specific cAMP-dependent protein kinases (cAMP-PK) activator. Sp-5,6-DCl-cBIMPS stimulates insulin release. Sp-5,6-DCl-cBIMPS inhibits U-46619 -induced activation of Rho, Gq and G12/G13 in platelets[1][2][3].
CAS Number
120912-54-1
UNSPSC
12352005
Target
PKA
Type
Reference compound
Related Pathways
Stem Cell/Wnt; TGF-beta/Smad
Applications
Metabolism-sugar/lipid metabolism
Field of Research
Metabolic Disease
Assay Protocol
https://www.medchemexpress.com/sp-5-6-dcl-cbimps.html
Solubility
10 mM in DMSO
Smiles
O[C@H]1[C@](O[C@@](CO2)([H])[C@@]1([H])O[P@]2(S)=O)([H])N(C=NC3=C4)C3=CC(Cl)=C4Cl
Molecular Formula
C12H11Cl2N2O5PS
Molecular Weight
397.17
References & Citations
[1]Sandberg M, et al. Characterization of Sp-5,6-dichloro-1-beta-D-ribofuranosylbenzimidazole- 3',5'-monophosphorothioate (Sp-5,6-DCl-cBiMPS) as a potent and specific activator of cyclic-AMP-dependent protein kinase in cell extracts and intact cells. Biochem J. 1991 Oct 15;279 (Pt 2) (Pt 2) :521-7.|[2]Laychock SG. Sp-5,6-dichloro-1-beta-D-ribofuranosylbenzimidazole-3',5'-cyclic monophosphorothioate is a potent stimulus for insulin release. Endocr Res. 1993;19 (2-3) :113-22.|[3]Gratacap MP, et al. Differential regulation of Rho and Rac through heterotrimeric G-proteins and cyclic nucleotides. J Biol Chem. 2001 Dec 21;276 (51) :47906-13.
Shipping Conditions
Room temperature
Scientific Category
Reference compound1
Clinical Information
No Development Reported

Chemical Information

(7R,8R)-7-(5,6-dichlorobenzimidazol-1-yl)-5a,7,8,8a-tetrahydro-5H-furo[3,2-e][1,4,2,3]dioxathiaphosphepine-5,8-diol
CAS Number120912-54-1
PubChem CID5487206
IUPAC Name(7R,8R)-7-(5,6-dichlorobenzimidazol-1-yl)-5a,7,8,8a-tetrahydro-5H-furo[3,2-e][1,4,2,3]dioxathiaphosphepine-5,8-diol
Molecular FormulaC12H11Cl2N2O5PS
Molecular Weight397.2
XLogP1.4
Topological Polar Surface Area111
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count1
Heavy Atom Count23
Formal Charge0
Complexity458
SMILES
C1=C2C(=CC(=C1Cl)Cl)N(C=N2)[C@H]3[C@@H](C4C(O3)C(OSPO4)O)O
InChI
InChI=1S/C12H11Cl2N2O5PS/c13-4-1-6-7(2-5(4)14)16(3-15-6)11-8(17)9-10(19-11)12(18)21-23-22-20-9/h1-3,8-12,17-18,22H/t8-,9?,10?,11-,12?,22?/m1/s1
InChIKey
NCXQEYBSXYJLGP-SBTLNALPSA-N
Chemical Structure
2D Structure
2D structure of (7R,8R)-7-(5,6-dichlorobenzimidazol-1-yl)-5a,7,8,8a-tetrahydro-5H-furo[3,2-e][1,4,2,3]dioxathiaphosphepine-5,8-diol
CAS: 120912-54-1
CID: 5487206
Formula: C12H11Cl2N2O5PS
MW: 397.2
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight397.2
XLogP31.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count1
Exact Mass395.9503350
Monoisotopic Mass395.9503350
Topological Polar Surface Area111 Ų
Heavy Atom Count23
Formal Charge0
Complexity458
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count3
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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Alternative Products

CatalogName
GTR19212679-01Sp-5,6-DCl-cBIMPS
BLG-D013-05Rp-5,6-DCl-cBIMPS
MBS565633-01Sp-5,6-Dichloro-cBIMPS
MBS256561-015, 6- Dichlorobenzimidazole riboside- 3', 5' - cyclic monophosphorothioate, Sp- isomer (Sp-5,6-DCl-cBIMPS)
466405-01Sp-5,6-DCI-cBiMPS
D 014-055, 6- Dichlorobenzimidazole riboside- 3', 5'- cyclic monophosphorothioate, Sp- isomer (Sp-5,6-DCl-cBIMPS), sodium salt
C3728-5Sp-5,6-dichloro-cBIMPS (sodium salt)
MBS256309-015, 6- Dichlorobenzimidazole riboside- 3', 5' - cyclic monophosphorothioate, Rp- isomer (Rp-5,6-DCl-cBIMPS)
BLG-T037Sp-2-CF3-cBIMPS
D 013-055, 6- Dichlorobenzimidazole riboside- 3', 5'- cyclic monophosphorothioate, Rp- isomer (Rp-5,6-DCl-cBIMPS), sodium salt

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