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Cyclic Adenosine Monophosphate

AlkaPlorer ID: AK003554

Synonym: None

IUPAC Name: (4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2-oxido-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol

Structure

SMILES: NC1=C2N=CN([C@@H]3O[C@@H]4COP(=O)([O-])O[C@H]4[C@H]3O)C2=NC=N1

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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)/p-1/t4-,6-,7-,10-/m1/s1

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InChIKey: IVOMOUWHDPKRLL-KQYNXXCUSA-M

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Properties Information

Molecule Weight: 328.201

TPSA？: 157.67000000000002

MolLogP？: -1.4494

Number of H-Donors: 2

Number of H-Acceptors: 11

RingCount: 4

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bos taurus cAMP-dependent protein kinase A K'a 1.0 None 10.1021/jm00102a006
Bos taurus Phosphodiesterase 3B Km 530.0 nM 10.1021/jm00346a017
Chlorocebus sabaeus Vero Cytotoxicity nan None 10.1021/jm00382a005
Equus caballus Alcohol dehydrogenase Ki 780000.0 nM 10.1021/jm00136a021
Homo sapiens ATP-binding cassette sub-family C member 11 Activity 74.0 % 10.1124/mol.104.007138
Homo sapiens ATP-binding cassette sub-family C member 11 Activity nan None 10.1074/jbc.m304059200
Homo sapiens Bloom syndrome protein Potency 3.5 nM None
Homo sapiens DNA polymerase eta Potency 281.8 nM None
Homo sapiens Dopamine D1 receptor Potency 366.3 nM None
Homo sapiens Dopamine D1 receptor Potency 19952.6 nM None
Homo sapiens Geminin Potency 22387.2 nM None
Homo sapiens HEK293 Potency 31.6 nM None
Homo sapiens HEK293 Potency 1635.3 nM None
Homo sapiens Histone acetyltransferase GCN5 Potency 39810.7 nM None
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 2377.8 nM None
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 2818.4 nM None
Homo sapiens Histone-lysine N-methyltransferase MLL Potency 125.9 nM None
Homo sapiens Multidrug resistance-associated protein 4 Activity 36.0 % 10.1681/asn.v133595
Homo sapiens Multidrug resistance-associated protein 4 Activity 39.6 % 10.1074/jbc.m104833200
Homo sapiens Multidrug resistance-associated protein 4 Activity 48.5 % None
Homo sapiens Multidrug resistance-associated protein 4 Activity nan None 10.1038/nrd3028
Homo sapiens Multidrug resistance-associated protein 4 Activity nan None 10.1042/0264-6021:3610497
Homo sapiens Multidrug resistance-associated protein 4 Km 44500.0 nM 10.1074/jbc.m104833200
Homo sapiens Multidrug resistance-associated protein 5 Activity 35.5 % 10.1074/jbc.m005463200
Homo sapiens Multidrug resistance-associated protein 5 Km 379000.0 nM 10.1074/jbc.m005463200
Homo sapiens Neuropeptide S receptor Potency 1584.9 nM None
Homo sapiens Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 Potency 952.8 nM None
Homo sapiens Phosphodiesterase 4 Hydrolysis 1.0 None 10.1021/jm00177a007
Homo sapiens Prelamin-A/C Potency 5.0 nM None
Homo sapiens Rap guanine nucleotide exchange factor 3 Kd 4500.0 nM 10.1021/acs.jmedchem.9b02151
Homo sapiens Rap guanine nucleotide exchange factor 4 IC50 40000.0 nM 10.1021/jm3014162
Homo sapiens Rap guanine nucleotide exchange factor 4 IC50 40000.0 nM 10.1021/jm401425e
Homo sapiens Rap guanine nucleotide exchange factor 4 IC50 48000.0 nM 10.1016/j.bmcl.2012.04.082
Homo sapiens Rap guanine nucleotide exchange factor 4 Ratio IC50 1.0 None 10.1016/j.bmcl.2012.04.082
Homo sapiens Regulator of G-protein signaling 4 Potency 842.9 nM None
Homo sapiens Solute carrier family 22 member 7 Activity nan None 10.1006/bbrc.2001.4774
Homo sapiens Solute carrier family 22 member 8 Activity nan None 10.1124/mol.59.5.1277
Homo sapiens Thyroid hormone receptor beta-1 Potency 0.6 nM None
Human alphaherpesvirus 1 Human alphaherpesvirus 1 ED50 5.0 mM l-1 10.1021/jm00382a005
Human alphaherpesvirus 1 Human alphaherpesvirus 1 Virus rating 0.0 None 10.1021/jm00382a005
Human alphaherpesvirus 2 Human alphaherpesvirus 2 ED50 5.0 mM l-1 10.1021/jm00382a005
Human alphaherpesvirus 2 Human alphaherpesvirus 2 Virus rating 0.2 None 10.1021/jm00382a005
Human respirovirus 3 Human respirovirus 3 ED50 5.0 mM l-1 10.1021/jm00382a005
Human respirovirus 3 Human respirovirus 3 Virus rating 0.0 None 10.1021/jm00382a005
Mus musculus L1210 Inhibition 26.0 % 10.1021/jm00382a005
Mus musculus P388 Inhibition 34.0 % 10.1021/jm00382a005
Rattus norvegicus C6 Activity 0.0 % 10.1021/jm00217a008
Rattus norvegicus C6 Activity 0.0 pmol/min 10.1021/jm00217a008
Rattus norvegicus Phosphodiesterase 5A Km 150000.0 nM 10.1016/j.bmcl.2004.03.021
Rattus norvegicus Phosphodiesterase 8A Km 50.0 nM 10.1016/j.bmcl.2004.03.021
Rattus norvegicus Solute carrier family 22 member 6 Activity nan None 10.1074/jbc.272.30.18526
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 4.96 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.27 % 10.6019/CHEMBL4495565
Streptomyces avidinii Streptavidin Activity nan None 10.1016/j.bmcl.2012.09.088
Vaccinia virus Vaccinia virus ED50 5.0 mM l-1 10.1021/jm00382a005
Vaccinia virus Vaccinia virus Virus rating 0.0 None 10.1021/jm00382a005
None NON-PROTEIN TARGET Activity nan None 10.1021/acs.jmedchem.9b00258
None Unchecked K1/2 3.8 uM 10.1021/jm0702581
None Unchecked K'a 1.0 None 10.1021/jm00102a006
None Unchecked Ka 8.0 M 10.1021/jm00389a015
None Unchecked Ka' 1.0 None 10.1021/jm00177a007
None Unchecked Km 0.63 None 10.1021/jm00345a010
None Unchecked Km 200.0 nM 10.1016/j.bmcl.2004.03.021
None Unchecked Km 560.0 nM 10.1021/jm00345a010
None Unchecked Km 560.0 nM 10.1021/jm00346a017
None Unchecked Km 710.0 nM 10.1016/j.bmcl.2011.08.036
None Unchecked Km 790.0 nM 10.1021/jm00346a017
None Unchecked Km 1300.0 nM 10.1021/jm00345a010
None Unchecked Potency 31.6 nM None
None Unchecked Potency 141.3 nM None
None Unchecked Potency 231.0 nM None
None Unchecked Specificity 1.0 None 10.1021/jm00102a006

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT021654 Nc1ncnc2c1ncn2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O>>Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](OP(=O)(O)O)[C@H]1O enzymemap_57316
AKRT021655 Nc1ncnc2c1ncn2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O>>Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O RXN0-5038
AKRT021656 Nc1ncnc2c1ncn2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O>>Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O1 MNXR182566
AKRT021657 Nc1ncnc2c1ncn2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O>>O=c1[nH]cnc2c1ncn2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O RXN-18398
AKRT022100 Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O>>Nc1ncnc2c1ncn2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O ADENYLATECYC-RXN