ID: ALA51697

Max Phase: Preclinical

Molecular Formula: C16H18N2

Molecular Weight: 238.33

Molecule Type: Small molecule

Representations

Synonyms (1): (S)-Nomifensine
Synonyms from Alternative Forms(1):

Canonical SMILES:  CN1Cc2c(N)cccc2[C@H](c2ccccc2)C1

Standard InChI:  InChI=1S/C16H18N2/c1-18-10-14(12-6-3-2-4-7-12)13-8-5-9-16(17)15(13)11-18/h2-9,14H,10-11,17H2,1H3/t14-/m0/s1

Standard InChI Key:  XXPANQJNYNUNES-AWEZNQCLSA-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: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 238.33

Molecular Weight (Monoisotopic): 238.1470

AlogP: 2.85

#Rotatable Bonds: 1

Polar Surface Area: 29.26

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 8.80

CX LogP: 2.62

CX LogD: 1.21

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.77

Np Likeness Score: 0.22

References

1. Bøgesø KP, Christensen AV, Hyttel J, Liljefors T..  (1985)  3-Phenyl-1-indanamines. Potential antidepressant activity and potent inhibition of dopamine, norepinephrine, and serotonin uptake.,  28  (12): [PMID:2999402] [10.1021/jm00150a012]

2. Moda TL, Montanari CA, Andricopulo AD..  (2007)  Hologram QSAR model for the prediction of human oral bioavailability.,  15  (24): [PMID:17870541] [10.1016/j.bmc.2007.08.060]

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. Pechulis AD, Beck JP, Curry MA, Wolf MA, Harms AE, Xi N, Opalka C, Sweet MP, Yang Z, Vellekoop AS, Klos AM, Crocker PJ, Hassler C, Laws M, Kitchen DB, Smith MA, Olson RE, Liu S, Molino BF..  (2012)  4-Phenyl tetrahydroisoquinolines as dual norepinephrine and dopamine reuptake inhibitors.,  22  (23): [PMID:23084899] [10.1016/j.bmcl.2012.09.050]

7. Brown DG, Bernstein PR, Wu Y, Urbanek RA, Becker CW, Throner SR, Dembofsky BT, Steelman GB, Lazor LA, Scott CW, Wood MW, Wesolowski SS, Nugiel DA, Koch S, Yu J, Pivonka DE, Li S, Thompson C, Zacco A, Elmore CS, Schroeder P, Liu J, Hurley CA, Ward S, Hunt HJ, Williams K, McLaughlin J, Hoesch V, Sydserff S, Maier D, Aharony D..  (2013)  Azepines and piperidines with dual norepinephrine dopamine uptake inhibition and antidepressant activity.,  4  (1): [PMID:24900562] [10.1021/ml300262e]

8. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

9. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]

10. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

11. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

Source

Source(4):

• Scientific Literature
• PubChem BioAssays
• AstraZeneca Deposited Data
• SARS-CoV-2 Screening Data 2020-21