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Compound Detail

CHEMBL388342

BOLDINE
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COc1cc2c(cc1O)C[C@H]1c3c(cc(O)c(OC)c3-2)CCN1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL388342
Name BOLDINE
Phase Preclinical
Structure Type MOL
InChI Key LZJRNLRASBVRRX-ZDUSSCGKSA-N
10
Targets
16
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

327.4
MW (Da)
2.87
ALogP
5
HBA
2
HBD
62.2
PSA (Ų)
0.89
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C19H21NO4
MW 327.38
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness 1.76

Activity Summary

IC50 10 meas. best 6.4
Ki 6 meas. best 8.31

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Alpha-1A adrenergic receptor
CHEMBL319
 Ki 8.31 8.31 4.9 1
D(1A) dopamine receptor
CHEMBL265
 Ki 6.54 6.54 290.0 1
Alpha-1B adrenergic receptor
CHEMBL315
 Ki 6.5 6.5 316.2 1
D(2) dopamine receptor
CHEMBL339
 Ki 6.43 6.43 370.0 1
D(1A) dopamine receptor
CHEMBL2056
 IC50 6.4 6.4 400.0 1
D(1A) dopamine receptor
CHEMBL265
 IC50 6.4 6.4 400.0 2
D(2) dopamine receptor
CHEMBL339
 IC50 6.3 6.29 500.0 2
D(2) dopamine receptor
CHEMBL217
 IC50 6.28 6.28 520.0 1
Casein kinase 2
CHEMBL3832943
 IC50 6.16 6.16 700.0 1
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907589
 Ki 5.52 5.52 3000.0 1
Sclerostin
CHEMBL3580487
 IC50 5.3 5.3 5000.0 1
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907589
 IC50 5.0 5.0 10000.0 1
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL2492
 Ki 4.17 4.17 67000.0 1
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL2492
 IC50 4.09 4.09 81000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Alpha-1A adrenergic receptor Ki = 4.898 nM 8.31 Displacement of [3H]prazosin from adrenergic alpha1A receptor in rat brain membr... 10785418
D(1A) dopamine receptor Ki = 290.0 nM 6.54 Displacement of [3H]SCH-23390 from rat dopamine D1 receptor 17228858
Alpha-1B adrenergic receptor Ki = 316.23 nM 6.5 Displacement of [3H]prazosin from adrenergic Alpha-1B receptor in rat brain memb... 10785418
D(2) dopamine receptor Ki = 370.0 nM 6.43 Displacement of [3H]raclopride from rat dopamine D2 receptor 17228858
D(1A) dopamine receptor IC50 = 400.0 nM 6.4 Displacement of [3H]SCH-23390 from rat dopamine D1 receptor 17228858
D(1A) dopamine receptor IC50 = 400.0 nM 6.4 Displacement of [3H]SCH23390 from dopamine D1 receptor in Wistar rat striatal me... 10785418
D(1A) dopamine receptor IC50 = 400.0 nM 6.4 Antagonist activity at D1 receptor (unknown origin) 39038276
D(2) dopamine receptor IC50 = 500.0 nM 6.3 Displacement of [3H]raclopride from rat dopamine D2 receptor 17228858
D(2) dopamine receptor IC50 = 520.0 nM 6.28 Displacement of [3H]raclopride from dopamine D2 receptor in Wistar rat striatal ... 10785418
D(2) dopamine receptor IC50 = 520.0 nM 6.28 Antagonist activity at D2 receptor (unknown origin) 39038276
Casein kinase 2 IC50 = 700.0 nM 6.16 Inhibition of CK2 (unknown origin) 30840451
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 3000.0 nM 5.52 Displacement of [3H]cytisine from human alpha-4-beta-2 nAChR expressed in SH-EP1... 17391965
Sclerostin IC50 = 5000.0 nM 5.3 Inhibition of sclerostin in human embryonic cells assessed as restoration of Wnt... -
Neuronal acetylcholine receptor; alpha4/beta2 IC50 = 10000.0 nM 5.0 Displacement of [3H]cytisine from human alpha-4-beta-2 nAChR expressed in SH-EP1... 17391965
Neuronal acetylcholine receptor subunit alpha-7 Ki = 67000.0 nM 4.17 Displacement of [125I]alpha-bungarotoxin from human alpha-7 nAChR expressed in S... 17391965
Neuronal acetylcholine receptor subunit alpha-7 IC50 = 81000.0 nM 4.09 Displacement of [125I]alpha-bungarotoxin from human alpha-7 nAChR expressed in S... 17391965

Literature References

PubMed DOI Target Context # Activities
9584402 10.1021/np970382v Poliovirus 2 4
17228858 10.1021/jm060959i Rattus norvegicus 3
17391965 10.1016/j.bmc.2007.03.023 Neuronal acetylcholine receptor; alpha4/beta2 2
17228858 10.1021/jm060959i D(1A) dopamine receptor 2
17228858 10.1021/jm060959i D(2) dopamine receptor 2
17391965 10.1016/j.bmc.2007.03.023 Neuronal acetylcholine receptor subunit alpha-7 2
10785418 10.1021/np990433j Unchecked 2
8786363 10.1021/np960195h Plasmodium falciparum 2
9584402 10.1021/np970382v Vero 2
39038276 10.1021/acs.jmedchem.4c00537 D(2) dopamine receptor 1
30840451 10.1021/acs.jnatprod.8b00889 Casein kinase 2 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B1 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B3 1
23062825 10.1016/j.bmc.2012.09.040 Cholinesterase 1
23062825 10.1016/j.bmc.2012.09.040 Acetylcholinesterase 1
9584402 10.1021/np970382v Unchecked 1
1710653 10.1021/np50073a012 Human immunodeficiency virus type 1 reverse transcriptase 1
10785418 10.1021/np990433j Alpha-1B adrenergic receptor 1
10785418 10.1021/np990433j Alpha-1A adrenergic receptor 1
10785418 10.1021/np990433j D(2) dopamine receptor 1

Data from ChEMBL 36 via Core Engine