(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; 2-amino-2-(hydroxymethyl)propane-1,3-diol

• ChemBase ID: 133793
• Molecular Formular: C14H23N6O9P
• Molecular Mass: 450.340981
• Monoisotopic Mass: 450.12641298
• SMILES: c1nc(c2c(n1)n(cn2)[C@H]1[C@@H]([C@H]2[C@H](O1)COP(=O)(O2)O)O)N.C(C(CO)(CO)N)O
• Canonical SMILES: O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1n1cnc2c1ncnc2N.OCC(CO)(CO)N
• InChI: InChI=1S/C10H12N5O6P.C4H11NO3/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;5-4(1-6,2-7)3-8/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13);6-8H,1-3,5H2/t4-,6-,7-,10-;/m1./s1
• InChIKey: CLDDYJFNXTUHIN-MCDZGGTQSA-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; 2-amino-2-(hydroxymethyl)propane-1,3-diol
• IUPAC Traditional name: tris buffer cyclic adenosine monophosphate
• Synonyms: cAMP; cyclic AMP; Adenosine 3′,5′-cyclic monophosphate tris salt; 腺苷-3′,5′-环单磷酸 三羟甲基氨基甲烷盐

Database IDs

• CAS Number: 102029-77-6
• MDL Number: MFCD00058346
• PubChem SID: 162228070
• PubChem CID: 71308717

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: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble100 mg/mL
• Apperance: white powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - A3262

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.