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Compound Detail

CHEMBL277041

METHYLTHIOADENOSINE
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CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL277041
Name METHYLTHIOADENOSINE
Phase Preclinical
Structure Type MOL
InChI Key WUUGFSXJNOTRMR-IOSLPCCCSA-N
9
Targets
26
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

297.3
MW (Da)
-0.61
ALogP
9
HBA
3
HBD
119.3
PSA (Ų)
0.69
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C11H15N5O3S
MW 297.34
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness 0.78

Activity Summary

IC50 13 meas. best 6.17
Ki 10 meas. best 6.82
Kd 3 meas. best 6.18

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine receptor A1
CHEMBL318
 Ki 6.82 6.7067 150.0 3
PRMT5/MEP50 complex
CHEMBL3137261
 Kd 6.18 6.18 661.0 1
Adenosine receptor A3
CHEMBL256
 Ki 6.17 6.17 680.0 1
Adenosine receptor A1
CHEMBL318
 IC50 6.17 5.495 680.0 2
Adenosine receptor A2a
CHEMBL302
 Ki 5.95 5.94 1130.0 2
Adenosine receptor A2b
CHEMBL255
 Ki 5.09 4.975 8200.0 2
Unchecked
CHEMBL612545
 Kd 5.0 4.98 10000.0 2
MOLT-4
CHEMBL614177
 IC50 4.96 4.96 11000.0 1
Unchecked
CHEMBL612545
 IC50 4.75 4.75 18000.0 2
L5178Y
CHEMBL614720
 IC50 4.22 4.22 60000.0 1
Adenosine receptor A3
CHEMBL256
 IC50 4.15 4.15 71000.0 1
Trypanosoma brucei brucei
CHEMBL612851
 IC50 4.0 4.0 100000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine receptor A1 Ki = 150.0 nM 6.82 Displacement of [3H]CCPA from adenosine A1 receptor of rat cortical membranes 15084123
Adenosine receptor A1 Ki = 210.0 nM 6.68 Displacement of [3H]DPCPX from adenosine A1 receptor of rat cortical membranes 15084123
Adenosine receptor A1 Ki = 240.0 nM 6.62 Displacement of [3H]R-PIA from adenosine A1 receptor of rat cortical membranes 15084123
PRMT5/MEP50 complex Kd = 661.0 nM 6.18 Inhibition of streptavidin sensor chip immobilized biotinylated human PRMT5/MEP5... 35041419
Adenosine receptor A1 IC50 = 680.0 nM 6.17 Displacement of [3H]DPCPX from adenosine A1 receptor of rat cortical membranes w... 15084123
Adenosine receptor A3 Ki = 680.0 nM 6.17 Displacement of [3H]PSB-11 from human adenosine A3 receptor expressed in CHO cel... 15084123
Adenosine receptor A2a Ki = 1130.0 nM 5.95 Displacement of [3H]-MSX-2 from Adenosine A2A receptor of rat striatal membranes 15084123
Adenosine receptor A2a Ki = 1180.0 nM 5.93 Displacement of [3H]NECA from Adenosine A2A receptor of rat striatal membranes 15084123
Adenosine receptor A2b Ki = 8200.0 nM 5.09 Binding affinity towards human adenosine A2B receptor in VA13 fibroblasts as inh... 15084123
Unchecked Kd = 10000.0 nM 5.0 Binding affinity to Clostridioides difficile-specific DNA adenine methyltransfer... 36581322
MOLT-4 IC50 = 11000.0 nM 4.96 The concentration required to inhibit cell growth by 50% was measured on human M... 1908523
Unchecked Kd = 11000.0 nM 4.96 Binding affinity to Clostridioides difficile-specific DNA adenine methyltransfer... 36581322
Adenosine receptor A2b Ki = 13900.0 nM 4.86 Displacement of [3H]PSB-298 from human adenosine A2B receptor expressed in HEK29... 15084123
Adenosine receptor A1 IC50 = 15100.0 nM 4.82 Displacement of [3H]DPCPX from adenosine A1 receptor of rat cortical membranes w... 15084123
Unchecked IC50 = 18000.0 nM 4.75 Inhibition of Clostridioides difficile-specific DNA adenine methyltransferase me... 36581322
Unchecked IC50 = 18000.0 nM 4.75 Inhibition of Clostridioides difficile-specific DNA adenine methyltransferase PD... 36581322
L5178Y IC50 = 60000.0 nM 4.22 Compound was evaluated for its ability to inhibit growth by 50% at 48 hr in L517... 2496231
Adenosine receptor A3 IC50 = 71000.0 nM 4.15 Inhibition of forskolin-stimulated cAMP accumulation in chinese hamster ovary ce... 15084123
Trypanosoma brucei brucei IC50 = 100000.0 nM 4.0 Antitrypanosomal activity against bloodstream form of Trypanosoma brucei brucei ... 17954686

Literature References

PubMed DOI Target Context # Activities
36581322 10.1021/acs.jmedchem.2c01789 Unchecked 7
15084123 10.1021/jm031092g Adenosine receptor A1 6
15911263 10.1016/j.bmcl.2005.03.107 S-methyl-5'-thioadenosine phosphorylase 6
1908523 10.1021/jm00112a039 Adenosylhomocysteinase 5
2496231 10.1021/jm00125a012 L5178Y 5
2496231 10.1021/jm00125a012 L1210 5
7241513 10.1021/jm00137a014 Spermidine synthase 4
1908523 10.1021/jm00112a039 L1210 4
1908523 10.1021/jm00112a039 L5178Y 4
17954686 10.1128/aac.00480-07 Trypanosoma brucei brucei 4
15084123 10.1021/jm031092g Adenosine receptor A3 3
17603473 10.1038/nature05981 5-methylthioadenosine/S-adenosylhomocysteine deaminase 3
17954686 10.1128/aac.00480-07 Unchecked 3
15084123 10.1021/jm031092g Adenosine receptor A2b 2
15084123 10.1021/jm031092g Adenosine receptor A2a 2
18083524 10.1016/j.bmc.2007.11.075 Unchecked 2
1908523 10.1021/jm00112a039 S-methyl-5'-thioadenosine phosphorylase 2
37560786 10.1021/acs.jmedchem.3c01030 Protein arginine N-methyltransferase 9 1
6279840 10.1021/jm00345a001 Adenosine A2 receptor 1
6620306 10.1021/jm00364a021 Indolethylamine N-methyltransferase 1

Data from ChEMBL 36 via Core Engine