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51116-01-9 molecular structure
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sodium (4aR,6R,7R,7aS)-6-(2-amino-8-bromo-6-oxo-6,9-dihydro-1H-purin-9-yl)-7-hydroxy-2-oxo-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-2-olate

ChemBase ID: 131320
Molecular Formular: C10H10BrN5NaO7P
Molecular Mass: 446.083231
Monoisotopic Mass: 444.9398906
SMILES and InChIs

SMILES:
C1[C@@H]2[C@H]([C@H]([C@@H](O2)n2c3c(c(=O)[nH]c(n3)N)nc2Br)O)OP(=O)(O1)[O-].[Na+]
Canonical SMILES:
O[C@@H]1[C@@H]2OP(=O)([O-])OC[C@H]2O[C@H]1n1c(Br)nc2c1nc(N)[nH]c2=O.[Na+]
InChI:
InChI=1S/C10H11BrN5O7P.Na/c11-9-13-3-6(14-10(12)15-7(3)18)16(9)8-4(17)5-2(22-8)1-21-24(19,20)23-5;/h2,4-5,8,17H,1H2,(H,19,20)(H3,12,14,15,18);/q;+1/p-1/t2-,4-,5-,8-;/m1./s1
InChIKey:
ZJRFCXHKYQVNFK-YEOHUATISA-M

Cite this record

CBID:131320 http://www.chembase.cn/molecule-131320.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
sodium (4aR,6R,7R,7aS)-6-(2-amino-8-bromo-6-oxo-6,9-dihydro-1H-purin-9-yl)-7-hydroxy-2-oxo-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-2-olate
IUPAC Traditional name
sodium (4aR,6R,7R,7aS)-6-(2-amino-8-bromo-6-oxo-1H-purin-9-yl)-7-hydroxy-2-oxo-tetrahydro-4H-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-2-olate
Synonyms
8-Br-cGMP
8-Bromoguanosine-3′,5′-cyclomonophosphate sodium salt
8-Bromo-cyclic GMP
8-Bromoguanosine 3′,5′-cyclic monophosphate sodium salt
CAS Number
51116-01-9
EC Number
256-993-8
MDL Number
MFCD00070128
Beilstein Number
8378760
PubChem SID
24278021
162225598
PubChem CID
23702959

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 23702959 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 1.9035653  H Acceptors
H Donor LogD (pH = 5.5) -3.215349 
LogD (pH = 7.4) -3.245903  Log P -1.1080263 
Molar Refractivity 78.2181 cm3 Polarizability 30.848368 Å3
Polar Surface Area 173.35 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
H2O: soluble0.1 g/mL, clear, slightly yellow expand Show data source
H2O: soluble50 mg/mL expand Show data source
Apperance
powder expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
Purity
≥98% (HPLC) expand Show data source
≥99.0% (HPLC) expand Show data source
Impurities
≤1% guanosine 3′,5′-cyclophosphate (HPLC) expand Show data source
≤8% water(2 mol/mol) expand Show data source
Empirical Formula (Hill Notation)
C10H10BrN5NaO7P expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - B1381 external link
Biochem/physiol Actions
Cell-permeable cGMP analog having greater resistance to hydrolysis by phosphodiesterases than cGMP. Activates cGMP-dependent protein kinase. Slows or inhibits the intracellular calcium oscillations of tracheal smooth muscle cells in response to acetylcholine. Reported to mimic the effect of nitric oxide generating drugs.
Sigma Aldrich - 17110 external link
Other Notes
A membrane-permeable cGMP derivative. Induces HL-60 cells to differentiate along the granulocytic pathway1

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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