4-((4-(((1S,2R)-2-phenylcyclopropylamino)methyl)piperidin-1-yl)methyl)benzoic acid

ID: ALA3775735

Chembl Id: CHEMBL3775735

PubChem CID: 86278919

Max Phase: Preclinical

Molecular Formula: C23H28N2O2

Molecular Weight: 364.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(CN2CCC(CN[C@H]3C[C@@H]3c3ccccc3)CC2)cc1

Standard InChI:  InChI=1S/C23H28N2O2/c26-23(27)20-8-6-18(7-9-20)16-25-12-10-17(11-13-25)15-24-22-14-21(22)19-4-2-1-3-5-19/h1-9,17,21-22,24H,10-16H2,(H,26,27)/t21-,22+/m1/s1

Standard InChI Key:  LRULVYSBRWUVGR-YADHBBJMSA-N

Alternative Forms

1. Parent:

   

   ALA3775735

   4-[[4-[[[(1S,2R)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methyl]benzoic acid

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: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 364.49

Molecular Weight (Monoisotopic): 364.2151

AlogP: 3.74

#Rotatable Bonds: 7

Polar Surface Area: 52.57

Molecular Species: ZWITTERION

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.64

CX Basic pKa: 10.20

CX LogP: 0.93

CX LogD: -0.56

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.79

Np Likeness Score: -0.79

References

1. Itoh Y, Aihara K, Mellini P, Tojo T, Ota Y, Tsumoto H, Solomon VR, Zhan P, Suzuki M, Ogasawara D, Shigenaga A, Inokuma T, Nakagawa H, Miyata N, Mizukami T, Otaka A, Suzuki T..  (2016)  Identification of SNAIL1 Peptide-Based Irreversible Lysine-Specific Demethylase 1-Selective Inactivators.,  59  (4): [PMID:26700437] [10.1021/acs.jmedchem.5b01323]

2. 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]

3. Schulz-Fincke J, Hau M, Barth J, Robaa D, Willmann D, Kürner A, Haas J, Greve G, Haydn T, Fulda S, Lübbert M, Lüdeke S, Berg T, Sippl W, Schüle R, Jung M..  (2018)  Structure-activity studies on N-Substituted tranylcypromine derivatives lead to selective inhibitors of lysine specific demethylase 1 (LSD1) and potent inducers of leukemic cell differentiation.,  144  [PMID:29247860] [10.1016/j.ejmech.2017.12.001]

Source

Source(1):

• Scientific Literature