ID: ALA26019

Max Phase: Preclinical

Molecular Formula: C10H15NO2

Molecular Weight: 181.24

Molecule Type: Small molecule

Representations

Synonyms (1): 2-(3,4-Dimethoxyphenyl)Ethanamine
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1ccc(CCN)cc1OC

Standard InChI:  InChI=1S/C10H15NO2/c1-12-9-4-3-8(5-6-11)7-10(9)13-2/h3-4,7H,5-6,11H2,1-2H3

Standard InChI Key:  ANOUKFYBOAKOIR-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: 181.24

Molecular Weight (Monoisotopic): 181.1103

AlogP: 1.20

#Rotatable Bonds: 4

Polar Surface Area: 44.48

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 9.80

CX LogP: 1.07

CX LogD: -1.24

Aromatic Rings: 1

Heavy Atoms: 13

QED Weighted: 0.76

Np Likeness Score: 0.28

References

1. Jacob P, Shulgin AT..  (1981)  Sulfur analogues of psychotomimetic agents. Monothio analogues of mescaline and isomescaline.,  24  (11): [PMID:7310812] [10.1021/jm00143a017]

2. Glennon RA, Liebowitz SM, Anderson GM..  (1980)  Serotonin receptor affinities of psychoactive phenalkylamine analogues.,  23  (3): [PMID:7365744] [10.1021/jm00177a017]

3. Clare BW..  (1990)  Structure-activity correlations for psychotomimetics. 1. Phenylalkylamines: electronic, volume, and hydrophobicity parameters.,  33  (2): [PMID:2299636] [10.1021/jm00164a036]

4. Yraola F, García-Vicente S, Fernandez-Recio J, Albericio F, Zorzano A, Marti L, Royo M..  (2006)  New efficient substrates for semicarbazide-sensitive amine oxidase/VAP-1 enzyme: analysis by SARs and computational docking.,  49  (21): [PMID:17034126] [10.1021/jm051076e]

5. PubChem BioAssay data set, 

6. Barker CA, Allison SE, Zlitni S, Nguyen ND, Das R, Melacini G, Capretta AA, Brown ED..  (2013)  Degradation of MAC13243 and studies of the interaction of resulting thiourea compounds with the lipoprotein targeting chaperone LolA.,  23  (8): [PMID:23473681] [10.1016/j.bmcl.2013.02.005]

7. Kier LB, Hall LH..  (1977)  Structure-activity studies on hallucinogenic amphetamines using molecular connectivity.,  20  (12): [PMID:592329] [10.1021/jm00222a019]

8. 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]

9. 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]

10. 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]

11. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of NIH (USA) - Clinical Collection,  [10.6019/CHEMBL4513141]

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

13. 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(6):

• Scientific Literature
• PubChem BioAssays
• CO-ADD antimicrobial screening data
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6