[(1R,2S)-2-phenylcyclopropyl]cyclohexane-1,4-diamine

ID: ALA3781751

Chembl Id: CHEMBL3781751

Max Phase: Phase

Molecular Formula: C15H22N2

Molecular Weight: 230.35

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: Iadademstat | ORY-1001 | RG-6016

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

Alternative Forms

  1. Parent:

    ALA3781751

    IADADEMSTAT
  2. Alternative Forms:

    ALA3781751

    ---

Associated Targets(Human)

KDM1A Tchem LSD1/CoREST complex (418 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAOA Tclin Monoamine oxidase A (11911 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAOB Tclin Monoamine oxidase B (8835 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KDM1B Tbio Lysine-specific histone demethylase 1B (147 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KDM1A Tchem Lysine-specific histone demethylase 1 (3916 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
THP-1 (11052 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCT-116 (91556 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PA-1 (704 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

F9 (77 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NIH3T3 (5395 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rep Replicase polyprotein 1ab (11336 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vero C1008 (1716 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: YesAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 230.35Molecular Weight (Monoisotopic): 230.1783AlogP: 2.40#Rotatable Bonds: 3
Polar Surface Area: 38.05Molecular Species: BASEHBA: 2HBD: 2
#RO5 Violations: HBA (Lipinski): 2HBD (Lipinski): 3#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 10.63CX LogP: 2.08CX LogD: -3.29
Aromatic Rings: 1Heavy Atoms: 17QED Weighted: 0.84Np 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]