ID: ALA266084

Max Phase: Preclinical

Molecular Formula: C12H14N2O

Molecular Weight: 202.26

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1ccc2[nH]c3c(c2c1)CCNC3

Standard InChI:  InChI=1S/C12H14N2O/c1-15-8-2-3-11-10(6-8)9-4-5-13-7-12(9)14-11/h2-3,6,13-14H,4-5,7H2,1H3

Standard InChI Key:  QYMDEOQLJUUNOF-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: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 202.26

Molecular Weight (Monoisotopic): 202.1106

AlogP: 1.82

#Rotatable Bonds: 1

Polar Surface Area: 37.05

Molecular Species: BASE

HBA: 2

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 9.10

CX LogP: 1.43

CX LogD: -0.26

Aromatic Rings: 2

Heavy Atoms: 15

QED Weighted: 0.74

Np Likeness Score: -0.06

References

1. Glennon RA, Grella B, Tyacke RJ, Lau A, Westaway J, Hudson AL..  (2004)  Binding of beta-carbolines at imidazoline I2 receptors: a structure-affinity investigation.,  14  (4): [PMID:15013009] [10.1016/j.bmcl.2003.11.078]

2. Chang-Fong J, Tyacke RJ, Lau A, Westaway J, Hudson AL, Glennon RA..  (2004)  Pyrazino[1,2-a]indoles as novel high-affinity and selective imidazoline I(2) receptor ligands.,  14  (4): [PMID:15013010] [10.1016/j.bmcl.2003.12.033]

3. Grella B, Teitler M, Smith C, Herrick-Davis K, Glennon RA..  (2003)  Binding of beta-carbolines at 5-HT(2) serotonin receptors.,  13  (24): [PMID:14643338] [10.1016/j.bmcl.2003.09.027]

4. Schott Y, Decker M, Rommelspacher H, Lehmann J..  (2006)  6-Hydroxy- and 6-methoxy-beta-carbolines as acetyl- and butyrylcholinesterase inhibitors.,  16  (22): [PMID:16945529] [10.1016/j.bmcl.2006.08.067]

5. Diamandis P, Wildenhain J, Clarke ID, Sacher AG, Graham J, Bellows DS, Ling EK, Ward RJ, Jamieson LG, Tyers M, Dirks PB..  (2007)  Chemical genetics reveals a complex functional ground state of neural stem cells.,  3  (5): [PMID:17417631] [10.1038/nchembio873]

6. PubChem BioAssay data set, 

7. PubChem BioAssay data set, 

8. PubChem BioAssay data set, 

9. PubChem BioAssay data set, 

10. PubChem BioAssay data set, 

11. Khorana N, Changwichit K, Ingkaninan K, Utsintong M..  (2012)  Prospective acetylcholinesterase inhibitory activity of indole and its analogs.,  22  (8): [PMID:22425563] [10.1016/j.bmcl.2012.02.057]

12. Rice AJ, Lei H, Santarsiero BD, Lee H, Johnson ME..  (2016)  Ca-asp bound X-ray structure and inhibition of Bacillus anthracis dihydroorotase (DHOase).,  24  (19): [PMID:27499369] [10.1016/j.bmc.2016.07.055]

13. 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]

14. 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(3):

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