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Compound Detail

CHEMBL52333

ROLOFYLLINE
🧪 Phase III
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🧪 Phase III
CCCn1c(=O)c2nc(C34CC5CC(CC3C5)C4)[nH]c2n(CCC)c1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL52333
Name ROLOFYLLINE
Phase Phase III
Structure Type MOL
InChI Key PJBFVWGQFLYWCB-UHFFFAOYSA-N

Known Names

KW 3902 KW-3902 KW3902 MK-7418 Rolofyllina Rolofylline
16
Targets
40
Activities
2
Assay Types
0
PK Parameters
20
Publications
6
Known Names
2
Indications
1
Mechanisms

Molecular Properties

356.5
MW (Da)
2.78
ALogP
5
HBA
1
HBD
72.7
PSA (Ų)
0.90
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Stem -fylline
USAN Year 2007

Extended Properties

Molecular Formula C20H28N4O2
MW 356.47
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness -0.29

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Adenosine A1 receptor antagonist ANTAGONIST Adenosine receptor A1 ✓ ✓

Indications

Heart Failure Heart Failure

Activity Summary

Ki 37 meas. best 9.84
Kd 3 meas. best 7.94

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine receptor A1
CHEMBL3688
 Ki 9.84 9.84 0.1 1
Adenosine receptor A1
CHEMBL4975
 Ki 9.72 9.72 0.2 1
Adenosine receptor A1
CHEMBL318
 Ki 9.72 9.19 0.2 5
Adenosine receptor A1
CHEMBL226
 Ki 9.53 9.1667 0.3 6
Adenosine receptor A1
CHEMBL2304404
 Ki 8.96 8.918 1.1 5
Adenosine receptor A1
CHEMBL226
 Kd 7.94 7.94 11.4 1
Adenosine receptor A2a
CHEMBL251
 Kd 7.46 7.17 34.8 2
Adenosine A2 receptor
CHEMBL2094257
 Ki 6.97 6.66 108.0 3
Adenosine receptor A2a
CHEMBL251
 Ki 6.97 6.97 108.0 2
Adenosine receptor A2a
CHEMBL302
 Ki 6.77 6.595 170.0 2
Adenosine receptor A2a
CHEMBL2605
 Ki 6.64 6.64 230.0 1
Adenosine receptor A2b
CHEMBL255
 Ki 6.57 6.55 269.0 2
Adenosine A2 receptor
CHEMBL2094117
 Ki 6.42 6.3767 380.0 3
Sodium-dependent dopamine transporter
CHEMBL238
 Ki 5.47 5.47 3362.0 1
Organic anion transporter 3
CHEMBL1641348
 Ki 5.43 5.43 3700.0 1
Adenosine receptor A3
CHEMBL256
 Ki 5.36 5.36 4390.0 2
Solute carrier family 22 member 6
CHEMBL1641347
 Ki 5.11 5.11 7820.0 1
Solute carrier family 22 member 11
CHEMBL2073677
 Ki 4.68 4.68 20700.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine receptor A1 Ki = 0.145 nM 9.84 Binding affinity to mouse adenosine A1 receptor 20188574
Adenosine receptor A1 Ki = 0.19 nM 9.72 Binding affinity towards adenosine A1 receptor in rat forebrain membranes using ... 1501234
Adenosine receptor A1 Ki = 0.19 nM 9.72 Binding affinity at bovine Adenosine A1 receptor. 12383013
Adenosine receptor A1 Ki = 0.19 nM 9.72 Binding affinity to rat adenosine A1 receptor 20188574
Adenosine receptor A1 Ki = 0.19 nM 9.72 Displacement of [3H]CCPA from adenosine receptor A1 in rat brain cortex membrane... 31780082
Adenosine receptor A1 Ki = 0.295 nM 9.53 Binding affinity to human adenosine A1 receptor 20188574
Adenosine receptor A1 Ki = 0.7 nM 9.15 Displacement of [3H]CCPA from human adenosine receptor A1 expressed in CHO cell ... 31780082
Adenosine receptor A1 Ki = 0.7 nM 9.15 Antagonist activity at adenosine A1 receptor (unknown origin) 34695776
Adenosine receptor A1 Ki = 0.72 nM 9.14 Inhibition of binding to membranes from HEK293 cells expressing human Adenosine ... 9191953
Adenosine receptor A1 Ki = 0.72 nM 9.14 Binding affinity to human adenosine A1 receptor by radioligand displacement assa... 30108984
Adenosine receptor A1 Ki = 1.1 nM 8.96 Binding affinity for Adenosine A1 receptor from Guinea pig membranes 9191953
Adenosine receptor A1 Ki = 1.1 nM 8.96 Binding affinity to guinea pig adenosine A1 receptor 20188574
Adenosine receptor A1 Ki = 1.3 nM 8.89 Displacement of [3H]cyclohexyladen from A1 adenosine receptor derived from in gu... 34019396
Adenosine receptor A1 Ki = 1.3 nM 8.89 Binding affinity against adenosine A1 receptor using N6-[3H]cyclohexyladenosine ... 1548682
Adenosine receptor A1 Ki = 1.3 nM 8.89 Binding affinity against adenosine A1 receptor using [3H]-CHA or [3H]PIA as radi... 1738138
Adenosine receptor A1 Ki = 1.3 nM 8.89 Binding affinity towards adenosine A1 receptor using N6-[3H]cyclohexyladenosine ... 1404238
Adenosine receptor A1 Ki = 1.3 nM 8.89 Binding affinity against adenosine A1 receptor in guinea pig forebrain membranes... 1501234
Adenosine receptor A1 Kd = 11.38 nM 7.94 The A1-StaR receptor has been purified from membranes in n-decyl-beta-D-maltosid... -
Adenosine receptor A1 Ki = 12.6 nM 7.9 Binding affinity for Adenosine A1 receptor of rat forebrain 9191953
Adenosine receptor A2a Kd = 34.81 nM 7.46 The A2A-StaR2 receptor has been purified from membranes in n-decyl-beta-D-maltos... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4689842 HEK-293T 346
- 10.6019/CHEMBL4689842 Fibroblast 345
- 10.6019/CHEMBL4689842 U2OS 345
1501234 10.1021/jm00094a022 Rattus norvegicus 44
- 10.6019/CHEMBL3885741 Adenosine receptor A2a 8
20188574 10.1016/j.bmc.2010.01.072 Adenosine receptor A1 4
- 10.6019/CHEMBL3885741 Adenosine receptor A1 3
9191953 10.1021/jm970013w Adenosine receptors; A1 & A2 3
9191953 10.1021/jm970013w Adenosine A2 receptor 3
9191953 10.1021/jm970013w Adenosine receptor A1 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
31780082 10.1016/j.ejmech.2019.111879 Adenosine receptor A2a 2
28238512 10.1016/j.bmc.2017.02.029 Rattus norvegicus 2
31780082 10.1016/j.ejmech.2019.111879 Adenosine receptor A1 2
1404238 10.1021/jm00097a016 No relevant target 2
20188574 10.1016/j.bmc.2010.01.072 Adenosine receptor A2a 2
- 10.6019/CHEMBL5209801 Sphingosine 1-phosphate receptor 1 2
1501234 10.1021/jm00094a022 Adenosine receptor A1 2

Data from ChEMBL 36 via Core Engine