Details of the Drug

General Information of Drug (ID: DMDNHEP)

Drug Name
QUINPIROLE
Synonyms
Quinpirolum; Quinpirol; Quinpirole [INN]; Quinpirolum [Latin]; Quinpirol [Spanish]; 80373-22-4; UNII-20OP60125T; CHEBI:75401; LY 156258; CHEMBL240773; (4aR-trans)-4,4a,5,6,7,8,8a,9-Octahydro-5-propyl-1H-pyrazolo(3,4-g)quinoline; 20OP60125T; 1H-Pyrazolo(3,4-g)quinoline, 4,4a,5,6,7,8,8a,9-octahydro-5-propyl-, (4aR-trans)-; (4aR,8aR)-5-propyl-1,4,4a,6,7,8,8a,9-octahydropyrido[2,3-f]indazole; (4aR,8aR)-5-propyl-1,4,4a,6,7,8,8a,9-octahydropyrazolo[3,4-g]quinoline
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 219.33
Logarithm of the Partition Coefficient (xlogp) 2.3
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C13H21N3
IUPAC Name
(4aR,8aR)-5-propyl-1,4,4a,6,7,8,8a,9-octahydropyrazolo[3,4-g]quinoline
Canonical SMILES
CCCN1CCC[C@H]2[C@H]1CC3=C(C2)NN=C3
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
InChIKey
FTSUPYGMFAPCFZ-ZWNOBZJWSA-N
Cross-matching ID
PubChem CID
54562
ChEBI ID
CHEBI:75401
CAS Number
80373-22-4
TTD ID
D0H2WQ

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Dopamine D1 receptor (D1R) TTZFYLI DRD1_HUMAN Inhibitor [2]
Dopamine D2 receptor (D2R) TTEX248 DRD2_HUMAN Inhibitor [3]
Dopamine D3 receptor (D3R) TT4C8EA DRD3_HUMAN Inhibitor [4]
Dopamine D4 receptor (D4R) TTE0A2F DRD4_HUMAN Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
D(2) dopamine receptor (DRD2) OTBLXKEG DRD2_HUMAN Drug Response [5]
Matrix metalloproteinase-9 (MMP9) OTB2QDAV MMP9_HUMAN Protein Interaction/Cellular Processes [5]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [6]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [6]
POU domain, class 5, transcription factor 1 (POU5F1) OTDHHN7O PO5F1_HUMAN Gene/Protein Processing [5]
Sodium-dependent dopamine transporter (SLC6A3) OT39XG28 SC6A3_HUMAN Protein Interaction/Cellular Processes [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Dopamine D1 receptor (D1R) DTT DRD1 8.99E-01 -0.06 -0.3
Dopamine D2 receptor (D2R) DTT DRD2 2.20E-03 -0.51 -1.35
Dopamine D4 receptor (D4R) DTT DRD4 1.90E-01 0.19 0.76
Dopamine D3 receptor (D3R) DTT DRD3 2.84E-03 0.13 2
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2).
2 Pharmacophore-guided drug discovery investigations leading to bioactive 5-aminotetrahydropyrazolopyridines. Implications for the binding mode of he... J Med Chem. 2005 Sep 8;48(18):5771-9.
3 N-n-Propyl-substituted 3-(dimethylphenyl)piperidines display novel discriminative properties between dopamine receptor subtypes: synthesis and rece... J Med Chem. 1998 Dec 3;41(25):4933-8.
4 1,1'-Disubstituted ferrocenes as molecular hinges in mono- and bivalent dopamine receptor ligands. J Med Chem. 2009 Nov 12;52(21):6860-70.
5 Activation of D2 Dopamine Receptors in CD133+ve Cancer Stem Cells in Non-small Cell Lung Carcinoma Inhibits Proliferation, Clonogenic Ability, and Invasiveness of These Cells. J Biol Chem. 2017 Jan 13;292(2):435-445. doi: 10.1074/jbc.M116.748970. Epub 2016 Dec 5.
6 Coupling of D2R Short but not D2R Long receptor isoform to the Rho/ROCK signaling pathway renders striatal neurons vulnerable to mutant huntingtin. Eur J Neurosci. 2017 Jan;45(1):198-206. doi: 10.1111/ejn.13415. Epub 2016 Oct 24.
7 The role of the dopamine transporter in dopamine-induced DNA damage. Brain Pathol. 2011 May;21(3):237-48. doi: 10.1111/j.1750-3639.2010.00440.x. Epub 2010 Sep 28.