(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: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]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

Database IDs

• CAS Number: 60-92-4
• EC Number: 200-492-9
• MDL Number: MFCD00005845
• Beilstein Number: 52645
• PubChem SID: 24278245; 162088126
• 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

• Acid pKa: 1.8324046
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -3.768807
• LogD (pH = 7.4): -3.6955175
• Log P: -4.0200067
• Molar Refractivity: 70.2895 cm^3
• Polarizability: 27.912539 Å^3
• Polar Surface Area: 154.84 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble10 mg/mL, clear, colorless (pH of aqueous solution is approx. 3.0. The sodium salt (A6885) is about 20× more soluble.)
• Apperance: white powder
• Melting Point: 219-220; 260 °C (dec.)(lit.)
• Optical Rotation: [α]20/D -54±2°, c = 0.7% in H2O; [α]22/D -53.7°, c = 0.7 in H2O

Safety Information

• Storage Condition: 0°C, Desiccate
• RTECS: AU7357600
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Gene Information: human ... OPRK1(4986)

Product Information

• Purity: ~99-100%; ≥98.5% (HPLC); ≥99.0% (HPLC)
• Packaging: vial of ~6 μmol (2 mg)
• Suitability: suitable for HPLC marker
• Impurities: ≤5% water
• Empirical Formula (Hill Notation): C10H12N5O6P

DETAILS

MP Biomedicals - 02100234

Free Acid
Crystalline
Purity: Approx. 99-100%

Sigma Aldrich - A9501

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

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

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

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.