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Compound Detail

CHEMBL405355

NIGULDIPINE
🧪 Phase II
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🧪 Phase II
COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCN2CCC(c3ccccc3)(c3ccccc3)CC2)[C@H]1c1cccc([N+](=O)[O-])c1

Basic Information

ChEMBL ID CHEMBL405355
Name NIGULDIPINE
Phase Phase II
Structure Type MOL
InChI Key SVJMLYUFVDMUHP-XIFFEERXSA-N

Known Names

(+)-niguldipine Niguldipine Niguldipino
49
Targets
63
Activities
2
Assay Types
0
PK Parameters
20
Publications
3
Known Names

Molecular Properties

609.7
MW (Da)
6.02
ALogP
8
HBA
1
HBD
111.0
PSA (Ų)
0.13
QED
2
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -dipine; -pine

Extended Properties

Molecular Formula C36H39N3O6
MW 609.72
Aromatic Rings 3
Heavy Atoms 45
NP-Likeness -0.69

Activity Summary

Ki 53 meas. best 9.8
IC50 10 meas. best 6.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Alpha-1A adrenergic receptor
CHEMBL229
Ki 9.8 9.1275 0.2 4
Alpha-1A adrenergic receptor
CHEMBL4892
Ki 9.42 9.42 0.4 1
Voltage-gated L-type calcium channel
CHEMBL2095177
Ki 8.34 8.34 4.6 1
Alpha-1A adrenergic receptor
CHEMBL319
Ki 8.2 8.2 6.4 1
Voltage-dependent L-type calcium channel subunit alpha-1C
CHEMBL3762
Ki 8.05 8.05 9.0 1
Alpha-1B adrenergic receptor
CHEMBL232
Ki 7.6 7.09 25.0 4
Adrenergic receptor alpha-1
CHEMBL1907610
Ki 7.56 7.56 27.8 1
Alpha-1D adrenergic receptor
CHEMBL326
Ki 7.08 7.08 82.4 1
Histamine H1 receptor
CHEMBL231
Ki 7.05 7.05 89.7 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 7.0 6.86 100.0 2
Mu-type opioid receptor
CHEMBL233
Ki 6.89 6.89 128.5 1
D(2) dopamine receptor
CHEMBL217
Ki 6.55 6.55 279.6 1
D(2) dopamine receptor
CHEMBL339
Ki 6.53 6.53 294.9 1
5-hydroxytryptamine receptor 7
CHEMBL3155
Ki 6.5 6.5 313.0 1
Sigma intracellular receptor 2
CHEMBL4105907
Ki 6.49 6.49 327.6 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 6.49 6.4667 322.1 3
Sigma non-opioid intracellular receptor 1
CHEMBL287
Ki 6.49 6.49 320.4 1
Kappa-type opioid receptor
CHEMBL237
Ki 6.46 6.46 346.9 1
5-hydroxytryptamine receptor 1B
CHEMBL1898
Ki 6.44 6.44 365.6 1
D(1A) dopamine receptor
CHEMBL2056
Ki 6.43 6.43 370.4 1
Alpha-1B adrenergic receptor
CHEMBL315
Ki 6.42 6.42 379.9 1
Delta-type opioid receptor
CHEMBL236
Ki 6.4 6.4 399.4 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 6.38 6.345 420.0 2
5-hydroxytryptamine receptor 5A
CHEMBL3426
Ki 6.37 6.37 430.5 1
D(3) dopamine receptor
CHEMBL234
Ki 6.37 6.37 424.7 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 6.28 6.0367 530.0 3
5-hydroxytryptamine receptor 1A
CHEMBL214
Ki 6.27 6.27 538.5 1
Sodium-dependent dopamine transporter
CHEMBL238
Ki 6.23 6.23 590.6 1
ATP-dependent translocase ABCB1
CHEMBL4302
IC50 6.15 6.15 708.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
Ki 6.14 6.14 717.6 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 6.07 6.07 857.2 1
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 6.06 6.06 878.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 6.06 6.06 862.1 1
Translocator protein
CHEMBL5742
Ki 6.02 6.02 952.9 1
D(1B) dopamine receptor
CHEMBL1850
Ki 5.91 5.91 1242.5 1
Adrenergic receptor alpha-2
CHEMBL2093864
Ki 5.79 5.79 1611.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 5.73 5.73 1854.8 1
Histamine H3 receptor
CHEMBL264
Ki 5.67 5.67 2135.5 1
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 5.67 5.67 2148.1 1
Adenosine receptor A3
CHEMBL256
Ki 5.55 5.55 2800.0 3
Sphingosine 1-phosphate receptor 1
CHEMBL4333
IC50 5.55 5.55 2835.6 1
Psychosine receptor
CHEMBL3714081
IC50 5.51 5.51 3081.4 1
G-protein coupled receptor 183
CHEMBL3259470
IC50 5.49 5.49 3249.8 1
N-formyl peptide receptor 3
CHEMBL5646
IC50 5.46 5.46 3436.2 1
Glucose-dependent insulinotropic receptor
CHEMBL5652
IC50 5.46 5.46 3437.8 1
G-protein coupled receptor 35
CHEMBL1293267
IC50 5.43 5.43 3743.1 1
fMet-Leu-Phe receptor
CHEMBL3359
IC50 5.42 5.42 3845.2 1
Apelin receptor
CHEMBL1628481
IC50 5.4 5.4 4007.7 1
Muscarinic acetylcholine receptor M2
CHEMBL211
IC50 5.36 5.36 4407.3 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Alpha-1A adrenergic receptor Ki = 0.16 nM 9.8 Binding constant measured against Alpha-1A adrenergic receptor in human prostate... 15664832
Alpha-1A adrenergic receptor Ki = 0.16 nM 9.8 Ability to displace [3H]prazosin from cloned human Alpha-1A adrenergic receptor 7752182
Alpha-1A adrenergic receptor Ki = 0.38 nM 9.42 Binding affinity towards Alpha-1A adrenergic receptor in bovine brain using [3H]... 8667368
Alpha-1A adrenergic receptor Ki = 1.8 nM 8.74 Inhibition of [3H]prazosin binding to human Alpha-1A adrenergic receptor express... 7562902
Voltage-gated L-type calcium channel Ki = 4.6 nM 8.34 Displacement of [3H]nitrendipine from rat brain L-type [Ca2+] channel 7752182
Alpha-1A adrenergic receptor Ki = 6.38 nM 8.2 Binding affinity towards Alpha-1A adrenergic receptor in rat hippocampal membran... 8667368
Alpha-1A adrenergic receptor Ki = 6.752 nM 8.17 PDSP Secondary Binding target: ADRA1A - Compounds are tested at 10 uM concentrat... -
Voltage-dependent L-type calcium channel subunit alpha-1C Ki = 9.0 nM 8.05 Inhibition of [3H]nitrendipine binding to membrane homogenates of of rat cardiac... 7562902
Alpha-1B adrenergic receptor Ki = 25.01 nM 7.6 Binding affinity towards Alpha-1B adrenergic receptor hamster smooth muscle usin... 8667368
Adrenergic receptor alpha-1 Ki = 27.8 nM 7.56 Binding affinity towards Alpha-1 adrenergic receptor in rat cerebral cortex usin... 8667368
Alpha-1B adrenergic receptor Ki = 55.0 nM 7.26 Ability to displace [3H]prazosin from cloned human Alpha-1B adrenergic receptor 7752182
Alpha-1D adrenergic receptor Ki = 82.41 nM 7.08 Binding affinity towards Alpha-1D adrenergic receptor in rat brain using [3H]pra... 8667368
Alpha-1B adrenergic receptor Ki = 85.0 nM 7.07 Inhibition of [3H]prazosin binding to human Alpha-1B adrenergic receptor express... 7562902
Histamine H1 receptor Ki = 89.66 nM 7.05 PDSP Secondary Binding target: HRH1 - Compounds are tested at 10 uM concentratio... -
Alpha-1D adrenergic receptor Ki = 100.0 nM 7.0 Ability to displace [3H]prazosin from cloned human Alpha-1D adrenergic receptor 7752182
Mu-type opioid receptor Ki = 128.53 nM 6.89 PDSP Secondary Binding target: OPRM1 - Compounds are tested at 10 uM concentrati... -
Alpha-1D adrenergic receptor Ki = 191.0 nM 6.72 Inhibition of [3H]prazosin binding to human Alpha-1D adrenergic receptor express... 7562902
D(2) dopamine receptor Ki = 279.64 nM 6.55 PDSP Secondary Binding target: DRD2 - Compounds are tested at 10 uM concentratio... -
D(2) dopamine receptor Ki = 294.9 nM 6.53 Binding affinity towards Dopamine receptor D2 in rat striatum using [3H]spiperon... 8667368
5-hydroxytryptamine receptor 7 Ki = 312.96 nM 6.5 PDSP Secondary Binding target: HTR7 - Compounds are tested at 10 uM concentratio... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4689842 U2OS 345
- 10.6019/CHEMBL4689842 HEK-293T 345
- 10.6019/CHEMBL4689842 Fibroblast 345
18024584 10.1073/pnas.0709695104 H4 13
- 10.6019/CHEMBL5209801 Alpha-2A adrenergic receptor 5
- 10.6019/CHEMBL5209801 Apelin receptor 5
- 10.6019/CHEMBL5209801 CX3C chemokine receptor 1 5
- 10.6019/CHEMBL5209801 Sphingosine 1-phosphate receptor 1 5
- 10.6019/CHEMBL5209801 Type-1 angiotensin II receptor 5
- 10.6019/CHEMBL5209801 Glucose-dependent insulinotropic receptor 5
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 5
- 10.6019/CHEMBL5209801 C5a anaphylatoxin chemotactic receptor 1 5
- 10.6019/CHEMBL5209801 N-formyl peptide receptor 2 5
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 5
- 10.6019/CHEMBL5209801 Glucagon-like peptide 1 receptor 5
- 10.6019/CHEMBL5209801 Adhesion G-protein coupled receptor F1 5
16033273 10.1021/jm0408969 Unchecked 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
20739103 10.1016/j.ejmech.2010.07.050 Saccharomyces cerevisiae 2
8667368 10.1021/jm960069a Alpha-1A adrenergic receptor 2

Data from ChEMBL 36 via Core Engine