VINPOCETINE

/static/temp/default.svg

Search structure


Synonyms	AY-27,255 AY-27255 Apovincaminic acid ethyl ester Bravinton Cavinton Ceractin Ethyl apovincamin-22-oate NSC-760093 Rgh 4405 Tcv 3b Ultra-vinca Vinpocetine Vinporal
Status
Molecule Category	UNKNOWN
ATC	N06BX18
UNII	543512OBTC
EPA CompTox	DTXSID5023740


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	DDNCQMVWWZOMLN-IRLDBZIGSA-N
Smiles	CCOC(=O)C1=C[C@]2(CC)CCCN3CCc4c(n1c1ccccc41)[C@@H]32
InChI	InChI=1S/C22H26N2O2/c1-3-22-11-7-12-23-13-10-16-15-8-5-6-9-17(15)24(19(16)20(22)23)18(14-22)21(25)26-4-2/h5-6,8-9,14,20H,3-4,7,10-13H2,1-2H3/t20-,22+/m1/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C22H26N2O2
Molecular Weight	350.46
AlogP	4.15
Hydrogen Bond Acceptor	4.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	3.0
Polar Surface Area	34.47
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	26.0

Assay Description	Organism	Bioactivity	Reference
Inhibition of diazepam-induced amnesia in NMRI mouse at 0.1 mg/kg, po by one-trial passive avoidance test	Mus musculus	0.0 %
Inhibition of diazepam-induced amnesia in NMRI mouse at 10 mg/kg, po by one-trial passive avoidance test	Mus musculus	100.0 %
Inhibition of electric eel AChE at 2 mg/ml by Ellman's method	Electrophorus electricus	12.34 %
Inhibition of horse BChE at 2 mg/ml by Ellman's method	Equus caballus	29.06 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	167.68 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	109.43 %
Inhibition of human ERG	Homo sapiens	39.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	2.1 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	12.94 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.17 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.17 %
Binding affinity to PDE1A (unknown origin) assessed as dissociation constant by SPR assay	Homo sapiens	13.88 10'-2/s

Cross References

Resources	Reference
ChEBI	32297
ChEMBL	CHEMBL71752
DrugBank	DB12131
DrugCentral	2828
FDA SRS	543512OBTC
Guide to Pharmacology	5285
PubChem	443955
SureChEMBL	SCHEMBL50081
ZINC	ZINC000019796031

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).