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Compound Detail

CHEMBL316966

CYCLIC ADENOSINE MONOPHOSPHATE
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Nc1ncnc2c1ncn2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL316966
Name CYCLIC ADENOSINE MONOPHOSPHATE
Phase Preclinical
Structure Type MOL
InChI Key IVOMOUWHDPKRLL-KQYNXXCUSA-N
2
Targets
5
Activities
3
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

329.2
MW (Da)
-0.82
ALogP
10
HBA
3
HBD
154.8
PSA (Ų)
0.57
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C10H12N5O6P
MW 329.21
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness 1.26

Activity Summary

IC50 3 meas. best 4.4
Kd 1 meas. best 5.35
Ki 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Rap guanine nucleotide exchange factor 3
CHEMBL2029197
 Kd 5.35 5.35 4500.0 1
Rap guanine nucleotide exchange factor 4
CHEMBL2029198
 IC50 4.4 4.3733 40000.0 3

Pharmacokinetic Data

Parameter Value Units Species
Ka 8.0 M Bos taurus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Rap guanine nucleotide exchange factor 3 Kd = 4500.0 nM 5.35 Binding affinity to GST-tagged human EPAC1 CNBD (149 to 318 residues) expressed ... 32297742
Rap guanine nucleotide exchange factor 4 IC50 = 40000.0 nM 4.4 Antagonist activity at recombinant EPAC2 (unknown origin) assessed 8-NBD-cAMP su... 23286832
Rap guanine nucleotide exchange factor 4 IC50 = 40000.0 nM 4.4 Inhibition of EPAC2 (unknown origin) 24256330
Rap guanine nucleotide exchange factor 4 IC50 = 48000.0 nM 4.32 Competitive inhibition of Epac2 using fluorescent nucleotide analog 8-NBD-cAMP b... 22607683

Literature References

PubMed DOI Target Context # Activities
195057 10.1021/jm00217a008 C6 4
6279842 10.1021/jm00345a010 Unchecked 3
2984417 10.1021/jm00382a005 Vaccinia virus 2
22607683 10.1016/j.bmcl.2012.04.082 Rap guanine nucleotide exchange factor 4 2
10893247 10.1074/jbc.m005463200 ATP-binding cassette sub-family C member 5 2
11447229 10.1074/jbc.m104833200 ATP-binding cassette sub-family C member 4 2
2984417 10.1021/jm00382a005 Human respirovirus 3 2
2984417 10.1021/jm00382a005 Human alphaherpesvirus 2 2
2984417 10.1021/jm00382a005 Human alphaherpesvirus 1 2
1335076 10.1021/jm00102a006 Unchecked 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
6279846 10.1021/jm00346a017 Unchecked 2
2984417 10.1021/jm00382a005 Vero 1
2984417 10.1021/jm00382a005 L1210 1
6245211 10.1021/jm00177a007 Unchecked 1
32297742 10.1021/acs.jmedchem.9b02151 Rap guanine nucleotide exchange factor 3 1
15125967 10.1016/j.bmcl.2004.03.021 cGMP-specific 3',5'-cyclic phosphodiesterase 1
6279846 10.1021/jm00346a017 Phosphodiesterase 3B 1
7021832 10.1021/jm00136a021 Alcohol dehydrogenase 1
3585903 10.1021/jm00389a015 Unchecked 1

Data from ChEMBL 36 via Core Engine