quinpirole   Click here for help

GtoPdb Ligand ID: 2

Synonyms: (-)-quinpirole
Compound class: Synthetic organic
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species
2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 31.92
Molecular weight 219.17
XLogP 2.34
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES CCCN1CCCC2C1Cc1cn[nH]c1C2
Isomeric SMILES CCCN1CCC[C@H]2[C@H]1Cc1cn[nH]c1C2
InChI InChI=1S/C13H21N3/c1-2-5-16-6-3-4-10-7-12-11(8-13(10)16)9-14-15-12/h9-10,13H,2-8H2,1H3,(H,14,15)/t10-,13-/m1/s1
InChI Key FTSUPYGMFAPCFZ-ZWNOBZJWSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Burris KD, Pacheco MA, Filtz TM, Kung MP, Kung HF, Molinoff PB. (1995)
Lack of discrimination by agonists for D2 and D3 dopamine receptors.
Neuropsychopharmacology, 12 (4): 335-45. [PMID:7576010]
2. Knight AR, Misra A, Quirk K, Benwell K, Revell D, Kennett G, Bickerdike M. (2004)
Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors.
Naunyn Schmiedebergs Arch Pharmacol, 370 (2): 114-23. [PMID:15322733]
3. Mierau J, Schneider FJ, Ensinger HA, Chio CL, Lajiness ME, Huff RM. (1995)
Pramipexole binding and activation of cloned and expressed dopamine D2, D3 and D4 receptors.
Eur J Pharmacol, 290 (1): 29-36. [PMID:7664822]
4. Millan MJ, Maiofiss L, Cussac D, Audinot V, Boutin JA, Newman-Tancredi A. (2002)
Differential actions of antiparkinson agents at multiple classes of monoaminergic receptor. I. A multivariate analysis of the binding profiles of 14 drugs at 21 native and cloned human receptor subtypes.
J Pharmacol Exp Ther, 303 (2): 791-804. [PMID:12388666]
5. Millan MJ, Peglion JL, Vian J, Rivet JM, Brocco M, Gobert A, Newman-Tancredi A, Dacquet C, Bervoets K, Girardon S. (1995)
Functional correlates of dopamine D3 receptor activation in the rat in vivo and their modulation by the selective antagonist, (+)-S 14297: 1. Activation of postsynaptic D3 receptors mediates hypothermia, whereas blockade of D2 receptors elicits prolactin secretion and catalepsy.
J Pharmacol Exp Ther, 275: 885-898. [PMID:7473180]
6. Newman-Tancredi A, Cussac D, Audinot V, Millan MJ. (1999)
Actions of roxindole at recombinant human dopamine D2, D3 and D4 and serotonin 5-HT1A, 5-HT1B and 5-HT1D receptors.
Naunyn Schmiedebergs Arch Pharmacol, 359 (6): 447-53. [PMID:10431754]
7. Patel S, Patel S, Marwood R, Emms F, Marston D, Leeson PD, Curtis NR, Kulagowski JJ, Freedman SB. (1996)
Identification and pharmacological characterization of [125I]L-750,667, a novel radioligand for the dopamine D4 receptor.
Mol Pharmacol, 50 (6): 1658-64. [PMID:8967990]
8. Sautel F, Griffon N, Lévesque D, Pilon C, Schwartz JC, Sokoloff P. (1995)
A functional test identifies dopamine agonists selective for D3versus D2receptors.
Neuroreport, 6: 329-332. [PMID:7756621]
9. Sokoloff P, Andrieux M, Besançon R, Pilon C, Martres MP, Giros B, Schwartz JC. (1992)
Pharmacology of human dopamine D3 receptor expressed in a mammalian cell line: comparison with D2 receptor.
Eur J Pharmacol, 225 (4): 331-7. [PMID:1354163]
10. Sokoloff P, Giros B, Martres MP, Bouthenet ML, Schwartz JC. (1990)
Molecular cloning and characterization of a novel dopamine receptor (D3) as a target for neuroleptics.
Nature, 347 (6289): 146-51. [PMID:1975644]
11. Van Tol HH, Bunzow JR, Guan HC, Sunahara RK, Seeman P, Niznik HB, Civelli O. (1991)
Cloning of the gene for a human dopamine D4 receptor with high affinity for the antipsychotic clozapine.
Nature, 350 (6319): 610-4. [PMID:1840645]