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60-92-4 molecular structure
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(4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-2-one

ChemBase ID: 102121
Molecular Formular: C10H12N5O6P
Molecular Mass: 329.205941
Monoisotopic Mass: 329.05251976
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
Canonical SMILES:
O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1n1cnc2c1ncnc2N
InChI:
InChI=1S/C10H12N5O6P/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)/t4-,6-,7-,10-/m1/s1
InChIKey:
IVOMOUWHDPKRLL-KQYNXXCUSA-N

Cite this record

CBID:102121 http://www.chembase.cn/molecule-102121.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-2-one
IUPAC Traditional name
cyclic adenosine monophosphate
Synonyms
Adenosine 3′,5′-cyclic monophosphate
Cyclic adenosine monophosphate
3',5'-Cyclic AMP
Adenosine 3',5'-cyclophosphate
cAMP
ADENOSINE-3',5'-cyclic-MONOPHOSPHORIC ACID
Adenosine 3′,5′-cyclophosphate
3′,5′-Cyclic AMP
环化腺苷酸
腺苷环磷酸酯
腺苷-3′,5′-环单磷酸
CAS Number
60-92-4
EC Number
200-492-9
MDL Number
MFCD00005845
Beilstein Number
52645
PubChem SID
162088126
24278245
PubChem CID
6076
CHEBI ID
17489
CHEMBL
316966
Chemspider ID
5851
DrugBank ID
DB02527
IUPHAR ligand ID
2352
KEGG ID
C00575
MeSH Name
Cyclic+AMP
Unique Ingredient Identifier
E0399OZS9N
Wikipedia Title
Cyclic_adenosine_monophosphate

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 1.8324046  H Acceptors
H Donor LogD (pH = 5.5) -3.768807 
LogD (pH = 7.4) -3.6955175  Log P -4.0200067 
Molar Refractivity 70.2895 cm3 Polarizability 27.912539 Å3
Polar Surface Area 154.84 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
H2O: soluble10 mg/mL, clear, colorless (pH of aqueous solution is approx. 3.0. The sodium salt (A6885) is about 20× more soluble.) expand Show data source
Apperance
white powder expand Show data source
Melting Point
219-220 expand Show data source
260 °C (dec.)(lit.) expand Show data source
Optical Rotation
[α]20/D -54±2°, c = 0.7% in H2O expand Show data source
[α]22/D -53.7°, c = 0.7 in H2O expand Show data source
Storage Condition
0°C, Desiccate expand Show data source
RTECS
AU7357600 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
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
2-8°C expand Show data source
Gene Information
human ... OPRK1(4986) expand Show data source
Purity
~99-100% expand Show data source
≥98.5% (HPLC) expand Show data source
≥99.0% (HPLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Packaging
vial of ~6 μmol (2 mg) expand Show data source
Suitability
suitable for HPLC marker expand Show data source
Impurities
≤5% water expand Show data source
Empirical Formula (Hill Notation)
C10H12N5O6P expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
MP Biomedicals - 02100234 external link
Free Acid
Crystalline
Purity: Approx. 99-100%
Sigma Aldrich - A9501 external link
包装
1, 5, 25 g in poly bottle
Biochem/physiol Actions
环化腺苷酸依赖性蛋白激酶 (PKA) 的自然活化剂。cAMP 是一种重要的第二信使,并且在很多系统中与神经递质或激素诱导的受体激活相关。已有显示,cAMP/PKA 信号通路可抑制细胞增殖,诱导分化并导致细胞凋亡。
Sigma Aldrich - N4897 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.
Sigma Aldrich - 851205 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.
Sigma Aldrich - 01895 external link
Other Notes
Intracellular messenger. Binding to cyclic AMP-dependent protein kinase1
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.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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