ID: ALA1411979

Max Phase: Approved

Molecular Formula: C14H19N3S

Molecular Weight: 261.39

Molecule Type: Small molecule

Representations

Synonyms (9): A 3322 | A-3322 | Metapyrilene | Pyrinistol | Restryl | Semikon | Sleepwell | Tenalin | Thionylan
Synonyms from Alternative Forms(9):

Canonical SMILES:  CN(C)CCN(Cc1cccs1)c1ccccn1

Standard InChI:  InChI=1S/C14H19N3S/c1-16(2)9-10-17(12-13-6-5-11-18-13)14-7-3-4-8-15-14/h3-8,11H,9-10,12H2,1-2H3

Standard InChI Key:  HNJJXZKZRAWDPF-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

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

Properties

Molecular Weight: 261.39

Molecular Weight (Monoisotopic): 261.1300

AlogP: 2.71

#Rotatable Bonds: 6

Polar Surface Area: 19.37

Molecular Species: BASE

HBA: 4

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 8.76

CX LogP: 3.11

CX LogD: 1.73

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.80

Np Likeness Score: -2.08

References

1. PubChem BioAssay data set, 

2. PubChem BioAssay data set, 

3. Obach RS, Lombardo F, Waters NJ..  (2008)  Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.,  36  (7): [PMID:18426954] [10.1124/dmd.108.020479]

4. Pelletier DJ, Gehlhaar D, Tilloy-Ellul A, Johnson TO, Greene N..  (2007)  Evaluation of a published in silico model and construction of a novel Bayesian model for predicting phospholipidosis inducing potential.,  47  (1): [PMID:17428028] [10.1021/ci6004542]

5. Lowe R, Glen RC, Mitchell JB..  (2010)  Predicting phospholipidosis using machine learning.,  7  (5): [PMID:20799726] [10.1021/mp100103e]

6. Greene N, Fisk L, Naven RT, Note RR, Patel ML, Pelletier DJ..  (2010)  Developing structure-activity relationships for the prediction of hepatotoxicity.,  23  (7): [PMID:20553011] [10.1021/tx1000865]

7. Ekins S, Williams AJ, Xu JJ..  (2010)  A predictive ligand-based Bayesian model for human drug-induced liver injury.,  38  (12): [PMID:20843939] [10.1124/dmd.110.035113]

8. Ekins S, Williams AJ, Xu JJ..  (2010)  A predictive ligand-based Bayesian model for human drug-induced liver injury.,  38  (12): [PMID:20843939] [10.1124/dmd.110.035113]

9. Kruhlak NL, Choi SS, Contrera JF, Weaver JL, Willard JM, Hastings KL, Sancilio LF..  (2008)  Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.,  18  (2): [PMID:20020916] [10.1080/15376510701857262]

10. PubChem BioAssay data set, 

11. Scott S. Auerbach, DrugMatrix¨ and ToxFX¨ Coordinator National Toxicology Program. DrugMatrix in vitro pharmacology data, 

12. Liu Z, Shi Q, Ding D, Kelly R, Fang H, Tong W..  (2011)  Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).,  7  (12): [PMID:22194678] [10.1371/journal.pcbi.1002310]

13. Dawson S, Stahl S, Paul N, Barber J, Kenna JG..  (2012)  In vitro inhibition of the bile salt export pump correlates with risk of cholestatic drug-induced liver injury in humans.,  40  (1): [PMID:21965623] [10.1124/dmd.111.040758]

14. WHO Anatomical Therapeutic Chemical Classification, 

15. Open TG-GATES,  [10.6019/CHEMBL3885861]

16. DrugMatrix,  [10.6019/CHEMBL3885881]

17. Warner DJ, Chen H, Cantin LD, Kenna JG, Stahl S, Walker CL, Noeske T..  (2012)  Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.,  40  (12): [PMID:22961681] [10.1124/dmd.112.047068]

18. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

19. 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]

20. Ma H, Liang H, Cai S, O'Keefe BR, Mooberry SL, Cichewicz RH..  (2021)  An Integrated Strategy for the Detection, Dereplication, and Identification of DNA-Binding Biomolecules from Complex Natural Product Mixtures.,  84  (3.0): [PMID:33226219] [10.1021/acs.jnatprod.0c00946]

21. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]

Source

Source(7):

• Scientific Literature
• PubChem BioAssays
• Open TG-GATEs
• DrugMatrix
• WHO Anatomical Therapeutic Chemical Classification
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6