Compound Detail

CHEMBL275084

ISOBUTYLMETHYLXANTHINE

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CC(C)Cn1c(=O)n(C)c(=O)c2nc[nH]c21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL275084
Name	ISOBUTYLMETHYLXANTHINE
Phase	Preclinical
Structure Type	MOL
InChI Key	APIXJSLKIYYUKG-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

222.2

MW (Da)

0.08

ALogP

HBA

HBD

72.7

PSA (Å²)

0.78

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C10H14N4O2
MW	222.25
Aromatic Rings	2
Heavy Atoms	16
NP-Likeness	-0.58

Activity Summary

IC50 39 meas. best 7.0

Ki 21 meas. best 7.3

EC50 3 meas. best 6.0

Kd 1 meas. best 5.23

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Adenosine receptor CHEMBL2111386	Ki	7.3	5.77	50.0	6
Phosphodiesterase 1 CHEMBL2111322	IC50	7.0	7.0	100.0	1
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B CHEMBL290	IC50	6.62	6.62	242.0	1
Canis familiaris CHEMBL373	EC50	6.0	5.63	1000.0	2
Sodium channel alpha subunits; brain (Types I, II, III) CHEMBL2096682	IC50	5.75	5.75	1800.0	1
cGMP-specific 3',5'-cyclic phosphodiesterase CHEMBL1827	IC50	5.68	4.7933	2100.0	3
Adenosine receptor A1 CHEMBL318	Ki	5.6	5.25	2500.0	5
Phosphodiesterase 1 CHEMBL2095150	IC50	5.47	5.335	3400.0	2
Rattus norvegicus CHEMBL376	IC50	5.46	5.46	3500.0	1
Unchecked CHEMBL612545	IC50	5.41	4.8186	3900.0	7
Phosphodiesterase 7 CHEMBL2111411	Ki	5.4	5.4	4000.0	1
cGMP-dependent 3',5'-cyclic phosphodiesterase CHEMBL2652	IC50	5.4	5.0467	4000.0	3
Adenosine receptor A2a CHEMBL302	Ki	5.24	5.24	5800.0	1
Adenosine receptor A1 CHEMBL226	Kd	5.23	5.23	5900.0	1
Adenosine A2 receptor CHEMBL2094117	Ki	5.2	4.975	6300.0	4
Phosphodiesterase 3 CHEMBL2094125	IC50	5.18	5.18	6600.0	1
Phosphodiesterase; PDE3 & PDE4 CHEMBL2095153	IC50	5.16	5.16	6900.0	1
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3A CHEMBL241	IC50	5.16	5.16	7000.0	1
Adenosine receptor A1 CHEMBL4975	Ki	5.16	5.16	7000.0	1
Adenosine receptor A1 CHEMBL318	IC50	5.16	5.16	7000.0	1
Adenosine receptor A2a CHEMBL2605	Ki	5.1	5.1	8000.0	2
Phosphodiesterase 7 CHEMBL2111411	IC50	5.09	5.09	8100.0	1
PDE5A/PDE6C CHEMBL4523626	Ki	5.07	5.07	8500.0	1
Heart phosphodiesterase CHEMBL2111408	IC50	5.0	5.0	9900.0	1
Adenosine A2 receptor CHEMBL2094117	IC50	4.89	4.89	13000.0	1
3',5'-cyclic-AMP phosphodiesterase 4B CHEMBL275	IC50	4.84	4.6467	14310.0	3
Phosphodiesterase 4 CHEMBL2093863	IC50	4.58	4.58	26300.0	1
3',5'-cyclic-AMP phosphodiesterase 4D CHEMBL288	IC50	4.51	4.465	31000.0	2
Cystic fibrosis transmembrane conductance regulator CHEMBL4051	EC50	4.35	4.35	45000.0	1
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A CHEMBL3012	IC50	4.07	4.07	85600.0	2

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Adenosine receptor	Ki	=	50.0	nM	7.3	Antagonist binding of 2-chloro-[3H]-adenosine to rat brain	6279840
Phosphodiesterase 1	IC50	=	100.0	nM	7.0	Evaluated for Ca++ dependent phosphodiesterase activity.	2374150
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B	IC50	=	242.0	nM	6.62	Inhibition of human His-tagged PDE3B catalytic domain expressed in Escherichia c...	26908025
Adenosine receptor	Ki	=	800.0	nM	6.1	Antagonist binding of L-N6-phenyl-isopropyl)-[3H]adenosine to rat brain	6279840
Canis familiaris	EC50	=	1000.0	nM	6.0	In vitro vascular relaxation in canine mesenteric veins precontracted with pheny...	1654425
Sodium channel alpha subunits; brain (Types I, II, III)	IC50	=	1800.0	nM	5.75	Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on vol...	2579237
Adenosine receptor	Ki	=	2000.0	nM	5.7	Antagonist binding of 2-chloro-[3H]-adenosine to rat brain	6279840
cGMP-specific 3',5'-cyclic phosphodiesterase	IC50	=	2100.0	nM	5.68	Inhibition of PDE5A (unknown origin)	26908025
Adenosine receptor A1	Ki	=	2500.0	nM	5.6	Binding affinity against Adenosine A1 receptor in rat brain membrane, using [3H]...	2795597
Adenosine receptor	Ki	=	3000.0	nM	5.52	Antagonist binding of rN6-cyclohexyl-[3H]adenosine to rat brain	6279840
Phosphodiesterase 1	IC50	=	3400.0	nM	5.47	Inhibition of [Ca(2+)]/calmodulin dependent phosphodiesterase PDE 1 of human lun...	2985781
Rattus norvegicus	IC50	=	3500.0	nM	5.46	Evaluated for Ca++ independent phosphodiesterase activity.	2374150
Unchecked	IC50	=	3900.0	nM	5.41	Inhibition of phosphodiesterase (peak-1) isolated from pig coronary artery asses...	177782
cGMP-dependent 3',5'-cyclic phosphodiesterase	IC50	=	4000.0	nM	5.4	Inhibition of human C-terminal His6-tagged PDE2A1 (215 to 900 residues) expresse...	26908025
Phosphodiesterase 7	Ki	=	4000.0	nM	5.4	Inhibition of human phosphodiesterase 7	15887951
Adenosine receptor	Ki	=	5000.0	nM	5.3	Antagonist binding of 2-chloro-[3H]-adenosine to rat brain	6279840
Canis familiaris	EC50	=	5500.0	nM	5.26	In vitro vascular relaxation in canine coronary arteries precontracted with pros...	1654425
Adenosine receptor A2a	Ki	=	5800.0	nM	5.24	Binding affinity for adenosine A2A receptor from rat brain membranes using [3H]C...	8410976
Adenosine receptor A1	Kd	=	5900.0	nM	5.23	Dissociation constant against Adenosine A1 receptor	15771445
Unchecked	IC50	=	6300.0	nM	5.2	Inhibition of phosphodiesterase (peak-1) isolated from pig coronary artery asses...	177782

Literature References

PubMed	DOI	Target Context	# Activities
1654425	10.1021/jm00113a002	Canis familiaris	11
6279840	10.1021/jm00345a001	Adenosine receptor	7
10096854	10.1021/np980431j	Monocyte	6
177782	10.1021/jm00226a010	Unchecked	6
19744861	10.1016/j.bmc.2009.08.041	Rattus norvegicus	5
35983865	10.1021/acs.jnatprod.2c00502	Unchecked	4
2213834	10.1021/jm00172a022	Adenosine A2 receptor	2
1654425	10.1021/jm00113a002	Unchecked	2
2374150	10.1021/jm00170a031	Rattus norvegicus	2
23571415	10.1124/mol.112.084152	Solute carrier organic anion transporter family member 1B3	2
15771445	10.1021/jm040842z	Adenosine receptor A1	2
2579237	10.1021/jm00381a019	Sodium channel alpha subunits; brain (Types I, II, III)	2
26908025	10.1021/acs.jmedchem.5b01813	High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	2
37536210	10.1016/j.ejmech.2023.115682	High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	2
28799755	10.1021/acs.jmedchem.7b00805	Unchecked	2
-	10.6019/CHEMBL4651402	SARS-CoV-2	2
6279840	10.1021/jm00345a001	Adenosine receptor A1	2
23571415	10.1124/mol.112.084152	Solute carrier organic anion transporter family member 1B1	2
29407945	10.1016/j.ejmech.2018.01.035	3',5'-cyclic-AMP phosphodiesterase 4D	2
6279840	10.1021/jm00345a001	Adenosine receptor A2a	1

Data from ChEMBL 36 via Core Engine