benzyl 1-(4-(2-aminocyclopropyl)phenylamino)-1-oxo-3-phenylpropan-2-ylcarbamate hydrochloride

ID: ALA3104337

PubChem CID: 46830228

Max Phase: Preclinical

Molecular Formula: C26H28ClN3O3

Molecular Weight: 429.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.NC1CC1c1ccc(NC(=O)C(Cc2ccccc2)NC(=O)OCc2ccccc2)cc1

Standard InChI:  InChI=1S/C26H27N3O3.ClH/c27-23-16-22(23)20-11-13-21(14-12-20)28-25(30)24(15-18-7-3-1-4-8-18)29-26(31)32-17-19-9-5-2-6-10-19;/h1-14,22-24H,15-17,27H2,(H,28,30)(H,29,31);1H

Standard InChI Key:  VYVWOUFCKCMSIG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    9.5048  -11.2757    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.4770   -8.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7527   -8.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7340   -7.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4398   -7.3305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1657   -7.7314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1808   -8.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9022   -8.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7237   -8.9444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3234   -9.6659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4321   -8.5215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0103   -7.3634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3053   -7.7921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5817   -7.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3241   -8.6168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5629   -6.5709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8767   -7.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8954   -8.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1910   -9.0753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2092   -9.8993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9335  -10.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6408   -9.8633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6189   -9.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8392   -6.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8206   -5.3499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1343   -6.6033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4106   -6.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7056   -6.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9846   -6.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2801   -6.6644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2984   -7.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0271   -7.8860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7286   -7.4558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  7  8  1  0
  9  8  1  0
 10  9  1  0
  8 10  1  0
  9 11  1  0
  4 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 16 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
M  END

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: 429.52

Molecular Weight (Monoisotopic): 429.2052

AlogP: 3.98

#Rotatable Bonds: 8

Polar Surface Area: 93.45

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.13

CX Basic pKa: 9.62

CX LogP: 4.04

CX LogD: 1.88

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.50

Np Likeness Score: -0.39

References

1. Sorna V, Theisen ER, Stephens B, Warner SL, Bearss DJ, Vankayalapati H, Sharma S..  (2013)  High-throughput virtual screening identifies novel N'-(1-phenylethylidene)-benzohydrazides as potent, specific, and reversible LSD1 inhibitors.,  56  (23): [PMID:24237195] [10.1021/jm400870h]

2. Valente S, Rodriguez V, Mercurio C, Vianello P, Saponara B, Cirilli R, Ciossani G, Labella D, Marrocco B, Ruoppolo G, Botrugno OA, Dessanti P, Minucci S, Mattevi A, Varasi M, Mai A..  (2015)  Pure Diastereomers of a Tranylcypromine-Based LSD1 Inhibitor: Enzyme Selectivity and In-Cell Studies.,  6  (2): [PMID:25699146] [10.1021/ml500424z]

3. Dai XJ, Liu Y, Xiong XP, Xue LP, Zheng YC, Liu HM..  (2020)  Tranylcypromine Based Lysine-Specific Demethylase 1 Inhibitor: Summary and Perspective.,  63  (23.0): [PMID:32931269] [10.1021/acs.jmedchem.0c00919]

Source

Source(1):

• Scientific Literature