9,10-Dimethoxy-3-methyl-2-(2,4,6-trimethyl-phenylimino)-2,3,6,7-tetrahydro-pyrimido[6,1-a]isoquinolin-4-one

ID: ALA285913

Chembl Id: CHEMBL285913

Max Phase: Phase

Molecular Formula: C24H27N3O3

Molecular Weight: 405.50

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Trequinsin

Synonyms from Alternative Forms(1): Trequinsin HCl

Canonical SMILES:  COc1cc2c(cc1OC)-c1c/c(=N\c3c(C)cc(C)cc3C)n(C)c(=O)n1CC2

Standard InChI:  InChI=1S/C24H27N3O3/c1-14-9-15(2)23(16(3)10-14)25-22-13-19-18-12-21(30-6)20(29-5)11-17(18)7-8-27(19)24(28)26(22)4/h9-13H,7-8H2,1-6H3/b25-22+

Standard InChI Key:  MCMSJVMUSBZUCN-YYDJUVGSSA-N

Alternative Forms

1. Parent:

   

   ALA285913

   TREQUINSIN

2. Alternative Forms:

   

   ALA285913

   TREQUINSIN HYDROCHLORIDE

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 405.50

Molecular Weight (Monoisotopic): 405.2052

AlogP: 3.58

#Rotatable Bonds: 3

Polar Surface Area: 57.75

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.37

CX LogP: 4.58

CX LogD: 4.57

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.67

Np Likeness Score: -0.17

References

1. Marivet MC, Bourguignon JJ, Lugnier C, Mann A, Stoclet JC, Wermuth CG..  (1989)  Inhibition of cyclic adenosine-3',5'-monophosphate phosphodiesterase from vascular smooth muscle by rolipram analogues.,  32  (7): [PMID:2544722] [10.1021/jm00127a009]

2. McNeal ET, Lewandowski GA, Daly JW, Creveling CR..  (1985)  [3H]Batrachotoxinin A 20 alpha-benzoate binding to voltage-sensitive sodium channels: a rapid and quantitative assay for local anesthetic activity in a variety of drugs.,  28  (3): [PMID:2579237] [10.1021/jm00381a019]

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. Bland ND, Wang C, Tallman C, Gustafson AE, Wang Z, Ashton TD, Ochiana SO, McAllister G, Cotter K, Fang AP, Gechijian L, Garceau N, Gangurde R, Ortenberg R, Ondrechen MJ, Campbell RK, Pollastri MP..  (2011)  Pharmacological validation of Trypanosoma brucei phosphodiesterases B1 and B2 as druggable targets for African sleeping sickness.,  54  (23): [PMID:22023548] [10.1021/jm201148s]

6. Chen ZS, Lee K, Walther S, Raftogianis RB, Kuwano M, Zeng H, Kruh GD..  (2002)  Analysis of methotrexate and folate transport by multidrug resistance protein 4 (ABCC4): MRP4 is a component of the methotrexate efflux system.,  62  (1): [PMID:12036927]

7. Jedlitschky G, Burchell B, Keppler D..  (2000)  The multidrug resistance protein 5 functions as an ATP-dependent export pump for cyclic nucleotides.,  275  (1): [PMID:10893247] [10.1074/jbc.m005463200]

8. Chen ZS, Hopper-Borge E, Belinsky MG, Shchaveleva I, Kotova E, Kruh GD..  (2003)  Characterization of the transport properties of human multidrug resistance protein 7 (MRP7, ABCC10).,  63  (1): [PMID:12527806] [10.1124/mol.63.2.351]

9. Reid G, Wielinga P, Zelcer N, De Haas M, Van Deemter L, Wijnholds J, Balzarini J, Borst P..  (2003)  Characterization of the transport of nucleoside analog drugs by the human multidrug resistance proteins MRP4 and MRP5.,  63  (1): [PMID:12695538] [10.1124/mol.63.5.1094]

10. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

11. Bakmiwewa SM, Fatokun AA, Tran A, Payne RJ, Hunt NH, Ball HJ..  (2012)  Identification of selective inhibitors of indoleamine 2,3-dioxygenase 2.,  22  (24): [PMID:23122865] [10.1016/j.bmcl.2012.10.010]

12. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

Source

Source(5):

• Scientific Literature
• PubChem BioAssays
• USP Dictionary of USAN and International Drug Names
• TP-search Transporter Database
• Fraunhofer HDAC6