(4aR,6S,7S,7aR)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-1,3,5,2$l^{5}-furo[3,2-d][1,3,2$l^{5}]dioxaphosphinin-2-one

• ChemBase ID: 2258
• Molecular Formular: C10H12N5O6P
• Molecular Mass: 329.205941
• Monoisotopic Mass: 329.05251976
• SMILES: Nc1ncnc2c1ncn2[C@H]1O[C@@H]2CO[P@@](=O)(O)O[C@@H]2[C@@H]1O
• Canonical SMILES: O[C@H]1[C@H]2O[P@](=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-ASCDQALMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4aR,6S,7S,7aR)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-1,3,5,2$l^{5}-furo[3,2-d][1,3,2$l^{5}]dioxaphosphinin-2-one
• IUPAC Traditional name: cAMP
• Synonyms: cAMP; Cyclic AMP; 3'-5'-cyclic adenosine monophosphate; Cyclic adenylic acid; 3',5'-Cyclic AMP; Cyclic Adenosine Monophosphate

Database IDs

• CAS Number: 60-92-4
• PubChem SID: 46508991; 160965711
• PubChem CID: 25322948

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.7814406
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -3.7316577
• LogD (pH = 7.4): -3.69503
• Log P: -3.8156195
• 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

ALOGPS 2.1

• Log P: -2.29
• LOG S: -1.96
• Solubility (Water): 3.58e+00 g/l

DETAILS

DrugBank - DB02527

• Drug Groups: experimental
• Description: Cyclic adenosine monophosphate (cAMP, cyclic AMP or 3'-5'-cyclic adenosine monophosphate) is a molecule that is important in many biological processes; it is derived from adenosine triphosphate (ATP).
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia