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37839-81-9 molecular structure
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sodium (4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-7-hydroxy-2-oxo-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-2-olate

ChemBase ID: 102912
Molecular Formular: C10H11N5NaO6P
Molecular Mass: 351.187771
Monoisotopic Mass: 351.03446401
SMILES and InChIs

SMILES:
c1nc(c2c(n1)n(cn2)[C@H]1[C@@H]([C@H]2[C@H](O1)COP(=O)(O2)[O-])O)N.[Na+]
Canonical SMILES:
O[C@@H]1[C@@H]2OP(=O)([O-])OC[C@H]2O[C@H]1n1cnc2c1ncnc2N.[Na+]
InChI:
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
InChIKey:
BXJBFCKTIWRKMQ-MCDZGGTQSA-M

Cite this record

CBID:102912 http://www.chembase.cn/molecule-102912.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
sodium (4aR,6R,7R,7aS)-6-(6-amino-9H-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 3',5'-cyclic amp anion
Synonyms
cAMP-Na
Adenosine 3′,5′-cyclic monophosphate sodium salt monohydrate
Adenosine-3',5'-Monophosphoric Acid
ADENOSINE-3',5'-cyclic-MONOPHOSPHATE SODIUM SALT
Adenosine Cyclic 3',5'-(Hydrogen Phosphate) Monosodium Salt
3',5'-AMP Sodium Salt
Adenosine 3',5'-Phosphoric Acid Sodium Salt
Cyclic 3',5'-AMP Sodium Salt
Cyclic 3',5'-Adenosine Monophosphate Monosodium Salt
Cyclic AMP Sodium
Cyclic AMP Sodium Salt
cAMP Sodium Salt
Adenosine-3',5'-cyclic Monophosphate Sodium Salt
3′,5′-Cyclic AMP sodium salt
环化腺苷酸 钠盐
腺苷-3′,5′-环单磷酸 钠盐 一水合物
CAS Number
37839-81-9
MDL Number
MFCD00069736
Beilstein Number
54612
PubChem SID
24891151
162088780
PubChem CID
23669773

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 23669773 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 1.8324043  H Acceptors
H Donor LogD (pH = 5.5) -3.768807 
LogD (pH = 7.4) -3.6955175  Log P -4.0200067 
Molar Refractivity 69.1678 cm3 Polarizability 27.794725 Å3
Polar Surface Area 157.67 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
H2O: soluble50 mg/mL expand Show data source
H2O: soluble50 mg/mL, clear, colorless expand Show data source
Apperance
white powder expand Show data source
Storage Condition
0°C expand Show data source
RTECS
AU7357900 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 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% expand Show data source
≥98.0% (HPLC) expand Show data source
≥99.0% (HPLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Shipped in
wet ice expand Show data source
Empirical Formula (Hill Notation)
C10H11N5NaO6P · H2O expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02105460 external link
Sodium Salt
Crystalline
Purity: Approx. 98%
Sigma Aldrich - A6885 external link
Application
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.
Biochem/physiol Actions
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 inhibit cell proliferation, induce differentiation and lead to apoptosis.
Sigma Aldrich - 01894 external link
Biochem/physiol Actions
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 inhibit cell proliferation, induce differentiation and lead to apoptosis.
Toronto Research Chemicals - A280455 external link
Adenosine-3’,5’-cyclic Monophosphate is an Adenosine (A280400) derivative useful as anticancer agent.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Keast, R., et al.: Pharma. Res., 19, 1019 (2002)
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PATENTS

PATENTS

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INTERNET

INTERNET

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