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Compound Detail

CHEMBL464859

NECA
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CCNC(=O)[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL464859
Name NECA
Phase Preclinical
Structure Type MOL
InChI Key JADDQZYHOWSFJD-FLNNQWSLSA-N
28
Targets
378
Activities
4
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

308.3
MW (Da)
-1.84
ALogP
9
HBA
4
HBD
148.4
PSA (Ų)
0.52
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 C12H16N6O4
MW 308.30
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness 0.43

Activity Summary

Ki 219 meas. best 9.35
EC50 99 meas. best 9.93
IC50 45 meas. best 9.68
Kd 15 meas. best 8.07

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine receptor A3
CHEMBL256
 EC50 9.93 7.3661 0.1 18
Adenosine receptor A1
CHEMBL226
 EC50 9.92 8.3953 0.1 19
Adenosine receptor A3
CHEMBL256
 IC50 9.68 8.6153 0.2 15
Adenosine receptor A1
CHEMBL226
 IC50 9.68 9.2433 0.2 3
Adenosine receptor A1
CHEMBL3688
 Ki 9.35 9.35 0.5 1
Adenosine receptor A3
CHEMBL256
 Ki 9.1 7.5564 0.8 44
Adenosine receptor A2a
CHEMBL251
 Ki 9.0 7.7118 1.0 51
Adenosine receptor A1
CHEMBL2304404
 Ki 9.0 9.0 1.0 1
Adenosine receptor A1
CHEMBL226
 Ki 8.98 7.7882 1.0 34
Adenosine receptor A1
CHEMBL318
 IC50 8.62 6.6313 2.4 8
Adenosine receptor A2a
CHEMBL251
 EC50 8.6 7.6793 2.5 15
Adenosine A2 receptor
CHEMBL2094257
 EC50 8.56 7.22 2.8 3
Adenosine receptor A2b
CHEMBL255
 EC50 8.5 6.7608 3.2 25
Adenosine receptor A2a
CHEMBL302
 Ki 8.38 7.978 4.1 15
Adenosine receptor A1
CHEMBL318
 Ki 8.29 7.6913 5.1 30
Adenosine receptor A2a
CHEMBL302
 IC50 8.15 7.295 7.0 2
Adenosine A2 receptor
CHEMBL2094117
 Ki 8.11 7.919 7.8 10
Adenosine receptor A1
CHEMBL226
 Kd 8.07 6.7629 8.6 7
Adenosine receptor A2a
CHEMBL251
 IC50 8.0 7.55 10.0 9
Adenosine receptor A1
CHEMBL4975
 Ki 7.85 7.85 14.0 4
Adenosine receptor A3
CHEMBL1075269
 Ki 7.85 7.85 14.1 1
Adenosine A2 receptor
CHEMBL2094117
 IC50 7.82 7.73 15.0 3
Transmembrane domain-containing protein TMIGD3
CHEMBL3712907
 Ki 7.8 7.8 16.0 1
Adenosine receptor A1
CHEMBL2114
 IC50 7.77 7.77 17.0 1
2-oxoglutarate receptor 1
CHEMBL2325
 Ki 7.57 7.5 27.0 2
Adenosine receptor A2a
CHEMBL302
 EC50 7.47 6.675 34.0 4
P3 purinoceptor
CHEMBL612413
 Ki 7.43 7.43 37.0 2
PBMC
CHEMBL613107
 IC50 7.4 7.065 40.0 2
Adenosine receptor A3
CHEMBL3360
 Ki 7.31 6.9678 49.0 9
Adenosine receptor A1
CHEMBL318
 EC50 7.26 7.21 54.8 4
Adenosine receptor A1
CHEMBL2304404
 EC50 7.2 7.2 63.1 1
Adenosine A2 receptor
CHEMBL2094257
 Ki 7.16 7.16 70.0 1
Endoplasmin
CHEMBL1075323
 Ki 6.96 6.96 110.0 2
Adenosine A2 receptor
CHEMBL2094117
 EC50 6.89 6.65 130.0 2
Canis familiaris
CHEMBL373
 EC50 6.82 6.82 150.0 1
Rattus norvegicus
CHEMBL376
 IC50 6.8 6.8 160.0 1
Adenosine receptor A3
CHEMBL1075269
 EC50 6.73 6.73 188.0 1
Endoplasmin
CHEMBL3425397
 Kd 6.7 6.7 200.0 2
Adenosine receptor A2b
CHEMBL255
 Ki 6.58 5.9633 262.0 9
Adenosine receptor A1
CHEMBL318
 Kd 6.53 6.53 295.1 1
Endoplasmin
CHEMBL1075323
 Kd 6.28 6.28 530.0 1
Homo sapiens
CHEMBL372
 IC50 6.22 6.22 600.0 1
Adenosine receptor A2b
CHEMBL2592
 Ki 5.58 5.58 2600.0 1
Heat shock protein HSP 90-alpha
CHEMBL3880
 Ki 5.57 5.57 2700.0 1
Endoplasmin
CHEMBL4748
 Kd 5.55 5.55 2800.0 1
Unchecked
CHEMBL612545
 Kd 5.45 5.45 3548.1 1
Heat shock protein HSP 90-alpha
CHEMBL3880
 Kd 4.85 4.595 14000.0 2
Cavia porcellus
CHEMBL369
 EC50 4.19 4.11 65000.0 4

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.002367 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine receptor A3 EC50 = 0.1175 nM 9.93 Antagonist activity at human wild type A3R expressed in Flp-In-CHO cells assesse... 35707146
Adenosine receptor A1 EC50 = 0.12 nM 9.92 Agonist activity at human A1A adenosine receptor expressed in HEK cell membranes... 30605331
Adenosine receptor A1 IC50 = 0.2089 nM 9.68 Agonist activity at human Adenosine A1 receptor transfected in CHO-K1 cells asse... 26756468
Adenosine receptor A3 IC50 = 0.2089 nM 9.68 Agonist activity at wild type human A3 receptor V169'5.30E mutant stably express... 31502843
Adenosine receptor A3 IC50 = 0.257 nM 9.59 Agonist activity at wild type human A3 receptor V169'5.30A/W185'5.46A double mut... 31502843
Adenosine receptor A3 IC50 = 0.2951 nM 9.53 Agonist activity at wild type human A3 receptor I249'6.54A mutant stably express... 31502843
Adenosine receptor A1 EC50 = 0.3631 nM 9.44 Activity at human adenosine A1 receptor assessed as inhibition of forskolin-stim... 17249651
Adenosine receptor A1 EC50 = 0.3631 nM 9.44 Agonist activity at adenosine A1 receptor assessed as inhibition of forskolin-st... 17249651
Adenosine receptor A1 EC50 = 0.4365 nM 9.36 Agonist activity at human A1AR expressed in FlpIn-CHO cells assessed as intracel... 29446948
Adenosine receptor A1 Ki = 0.45 nM 9.35 Displacement of [3H]N6-R-phenylisopropyladenosine from mouse A1A adenosine recep... 30605331
Adenosine receptor A3 IC50 = 0.4898 nM 9.31 Agonist activity at wild type human A3 receptor V169'5.30A mutant stably express... 31502843
Adenosine receptor A3 IC50 = 0.4898 nM 9.31 Agonist activity at human Adenosine A3 receptor transfected in CHO-K1 cells asse... 26756468
Adenosine receptor A1 EC50 = 0.5012 nM 9.3 Irreversible agonist activity at human adenosine A1 receptor expressed in Flp-In... 27958734
Adenosine receptor A3 IC50 = 0.5888 nM 9.23 Agonist activity at wild type human A3 receptor I253'6.58E mutant stably express... 31502843
Adenosine receptor A3 IC50 = 0.6166 nM 9.21 Agonist activity at wild type human A3 receptor W185'5.46A mutant stably express... 31502843
Adenosine receptor A1 EC50 = 0.7586 nM 9.12 Agonist activity at human A1AR expressed in FlpIn-CHO cells assessed as inhibiti... 29446948
Adenosine receptor A3 IC50 = 0.7762 nM 9.11 Agonist activity at wild type human A3 receptor L264'7.35A mutant stably express... 31502843
Adenosine receptor A3 Ki = 0.8 nM 9.1 Binding affinity towards human Adenosine A3 receptor wild type 12238926
Adenosine receptor A1 IC50 = 0.7943 nM 9.1 Agonist activity at human adenosine A1 receptor expressed in CHO cells assessed ... -
Adenosine receptor A3 Ki = 0.9 nM 9.05 Binding affinity towards Adenosine A3 receptor (W243 A mutant receptor) 12238926

Literature References

PubMed DOI Target Context # Activities
31502843 10.1021/acs.jmedchem.9b01164 Adenosine receptor A3 18
15267242 10.1021/jm031143+ Cavia porcellus 12
36270633 10.1021/acs.jmedchem.2c01414 Adenosine receptor A1 12
1875349 10.1021/jm00112a035 Rattus norvegicus 10
27958734 10.1021/acs.jmedchem.6b01561 Adenosine receptor A1 10
- 10.1039/C2MD00247G Adenosine receptor A1 7
36173355 10.1021/acs.jmedchem.2c01123 Adenosine receptor A1 7
14584936 10.1021/jm0300431 Adenosine receptor A2a 7
15267242 10.1021/jm031143+ Adenosine receptor A2a 6
7365748 10.1021/jm00177a021 Canis familiaris 6
29446948 10.1021/acs.jmedchem.8b00047 Adenosine receptor A1 6
17249651 10.1021/jm061279i Adenosine receptor A1 6
35729775 10.1021/acs.jmedchem.2c00320 Adenosine receptor A1 6
30605331 10.1021/acs.jmedchem.8b01662 Adenosine receptor A1 6
12238926 10.1021/jm020211+ Adenosine receptor A3 6
39073853 10.1021/acs.jmedchem.4c01092 Unchecked 6
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
26756468 10.1021/acs.jmedchem.5b01402 Adenosine receptor A1 4
15267242 10.1021/jm031143+ Adenosine receptor A2b 4
34844790 10.1016/j.ejmech.2021.113983 Adenosine receptor A3 4

Data from ChEMBL 36 via Core Engine