ID: ALA3781751

Max Phase: Phase

Molecular Formula: C15H22N2

Molecular Weight: 230.35

Molecule Type: Small molecule

Representations

Synonyms (3): Iadademstat | ORY-1001 | RG-6016
Synonyms from Alternative Forms(3):

Canonical SMILES:  N[C@H]1CC[C@H](N[C@@H]2C[C@H]2c2ccccc2)CC1

Standard InChI:  InChI=1S/C15H22N2/c16-12-6-8-13(9-7-12)17-15-10-14(15)11-4-2-1-3-5-11/h1-5,12-15,17H,6-10,16H2/t12-,13-,14-,15+/m0/s1

Standard InChI Key:  ALHBJBCQLJZYON-ZQDZILKHSA-N

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

Properties

Molecular Weight: 230.35

Molecular Weight (Monoisotopic): 230.1783

AlogP: 2.40

#Rotatable Bonds: 3

Polar Surface Area: 38.05

Molecular Species: BASE

HBA: 2

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 10.63

CX LogP: 2.08

CX LogD: -3.29

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.84

Np Likeness Score: -0.43

References

1. Vianello P, Botrugno OA, Cappa A, Dal Zuffo R, Dessanti P, Mai A, Marrocco B, Mattevi A, Meroni G, Minucci S, Stazi G, Thaler F, Trifiró P, Valente S, Villa M, Varasi M, Mercurio C..  (2016)  Discovery of a Novel Inhibitor of Histone Lysine-Specific Demethylase 1A (KDM1A/LSD1) as Orally Active Antitumor Agent.,  59  (4): [PMID:26702542] [10.1021/acs.jmedchem.5b01209]

2.  (2016)  (Hetero)aryl cyclopropylamine compounds as LSD1 inhibitors, 

3. Vianello P, Sartori L, Amigoni F, Cappa A, Fagá G, Fattori R, Legnaghi E, Ciossani G, Mattevi A, Meroni G, Moretti L, Cecatiello V, Pasqualato S, Romussi A, Thaler F, Trifiró P, Villa M, Botrugno OA, Dessanti P, Minucci S, Vultaggio S, Zagarrí E, Varasi M, Mercurio C..  (2017)  Thieno[3,2-b]pyrrole-5-carboxamides as New Reversible Inhibitors of Histone Lysine Demethylase KDM1A/LSD1. Part 2: Structure-Based Drug Design and Structure-Activity Relationship.,  60  (5): [PMID:28186757] [10.1021/acs.jmedchem.6b01019]

4. Hoang N, Zhang X, Zhang C, Vo V, Leng F, Saxena L, Yin F, Lu F, Zheng G, Bhowmik P, Zhang H..  (2018)  New histone demethylase LSD1 inhibitor selectively targets teratocarcinoma and embryonic carcinoma cells.,  26  (8): [PMID:29439916] [10.1016/j.bmc.2018.01.031]

5. 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]

6. 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]

7. Unpublished dataset, 

8. Li C, Su M, Zhu W, Kan W, Ge T, Xu G, Wang S, Sheng L, Gao F, Ye Y, Wang J, Zhou Y, Li J, Liu H..  (2022)  Structure-Activity Relationship Study of Indolin-5-yl-cyclopropanamine Derivatives as Selective Lysine Specific Demethylase 1 (LSD1) Inhibitors.,  65  (5.0): [PMID:35200034] [10.1021/acs.jmedchem.1c02156]

9. Vaidergorn MM, da Silva Emery F, Ganesan A..  (2021)  From Hit Seeking to Magic Bullets: The Successful Union of Epigenetic and Fragment Based Drug Discovery (EPIDD + FBDD).,  64  (19.0): [PMID:34591474] [10.1021/acs.jmedchem.1c00787]

Source

Source(4):

• Scientific Literature
• Clinical Candidates
• BindingDB Database
• SARS-CoV-2 Screening Data 2020-21