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Compound Detail

CHEMBL71752

VINPOCETINE
🧪 Phase II
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🧪 Phase II
CCOC(=O)C1=C[C@]2(CC)CCCN3CCc4c(n1c1ccccc41)[C@@H]32
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL71752
Name VINPOCETINE
Phase Phase II
Structure Type MOL
InChI Key DDNCQMVWWZOMLN-IRLDBZIGSA-N
Therapeutic ✓ Yes

Known Names

Apovincaminic acid ethyl ester AY-27,255 AY-27255 Bravinton Cavinton Ceractin Ethyl apovincamin-22-oate NSC-760093 Rgh 4405 Tcv 3b Ultra-vinca Vinpocetina +2 more
7
Targets
19
Activities
2
Assay Types
2
PK Parameters
20
Publications
14
Known Names
3
Indications

Molecular Properties

350.5
MW (Da)
4.15
ALogP
4
HBA
0
HBD
34.5
PSA (Ų)
0.78
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem vin-
USAN Year 1981

Extended Properties

Molecular Formula C22H26N2O2
MW 350.46
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness 0.65

Indications

Attention Deficit Disorder with Hyperactivity Diabetic Nephropathies Epilepsy

ATC Classification

N06BX18
vinpocetine
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

IC50 18 meas. best 7.41
Ki 1 meas. best 4.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 7.41 7.41 39.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.1 4.95 7943.3 6
Dual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1B
CHEMBL4425
 IC50 5.1 5.1 7990.0 1
Phosphodiesterase 1
CHEMBL2095150
 IC50 5.0 4.68 10000.0 3
Phosphodiesterase 1
CHEMBL2095150
 Ki 4.85 4.85 14000.0 1
Phosphodiesterase 1
CHEMBL2097166
 IC50 4.72 4.72 19000.0 1
Dual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1A
CHEMBL3421
 IC50 4.72 4.72 18840.0 1
Unchecked
CHEMBL612545
 IC50 4.52 4.52 30000.0 3

Pharmacokinetic Data

Parameter Value Units Species
Ka 1.5 10'3/M/s Homo sapiens
T1/2 13.1 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 39.0 nM 7.41 Inhibition of human ERG 28406621
Plasmodium falciparum IC50 = 7943.28 nM 5.1 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Dual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1B IC50 = 7990.0 nM 5.1 Inhibition of human recombinant PDE1B using cAMP as substrate incubated for 20 m... 33022582
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Phosphodiesterase 1 IC50 = 10000.0 nM 5.0 Inhibition of PDE1 (unknown origin) 33412421
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Phosphodiesterase 1 Ki = 14000.0 nM 4.85 Inhibition of human phosphodiesterase 1 15887951
Phosphodiesterase 1 IC50 = 19000.0 nM 4.72 Evaluated for inhibitory activity against Phosphodiesterase 1 (PDE1) purified fr... 9216839
Dual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1A IC50 = 18840.0 nM 4.72 Inhibition of PDE1A (unknown origin) 31859156
Unchecked IC50 = 30000.0 nM 4.52 Inhibition of PDE1 (unknown origin) 29363967
Phosphodiesterase 1 IC50 = 30000.0 nM 4.52 Inhibition of PDE1 (unknown origin) 35144038
Phosphodiesterase 1 IC50 = 30000.0 nM 4.52 Inhibition of PDE1 (unknown origin) 34042442
Unchecked IC50 = 30000.0 nM 4.52 Inhibition of PDE1 (unknown origin) 38000211
Unchecked IC50 = 30000.0 nM 4.52 Inhibition of PDE1 (unknown origin) 38614063

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 89
- 10.6019/CHEMBL5303304 HEK-293T 8
- 10.6019/CHEMBL5303304 U2OS 6
19734910 10.1038/nchembio.215 Plasmodium falciparum 6
31859156 10.1016/j.bmcl.2019.05.052 Rattus norvegicus 6
- 10.6019/CHEMBL5303304 Fibroblast 5
31859156 10.1016/j.bmcl.2019.05.052 Dual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1A 5
- 10.6019/CHEMBL4651402 SARS-CoV-2 4
22793155 10.1021/jm3007992 No relevant target 3
28406621 10.1021/acs.jmedchem.7b00302 Liver 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 2
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 2
37468498 10.1038/s41467-023-40064-9 Androgen receptor 2
18183943 10.1021/jm070618k Mus musculus 2
18183943 10.1021/jm070618k Rattus norvegicus 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 2

Data from ChEMBL 36 via Core Engine