trans-benzyl 2-((4-((2-aminocyclopropyl)phenyl)carbamoyl)pyrrolidine-1-carboxylate hydrochloride

ID: ALA3736172

PubChem CID: 127035482

Max Phase: Preclinical

Molecular Formula: C22H26ClN3O3

Molecular Weight: 379.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.N[C@@H]1C[C@H]1c1ccc(NC(=O)C2CCCN2C(=O)OCc2ccccc2)cc1

Standard InChI:  InChI=1S/C22H25N3O3.ClH/c23-19-13-18(19)16-8-10-17(11-9-16)24-21(26)20-7-4-12-25(20)22(27)28-14-15-5-2-1-3-6-15;/h1-3,5-6,8-11,18-20H,4,7,12-14,23H2,(H,24,26);1H/t18-,19+,20?;/m0./s1

Standard InChI Key:  WPEBVTLUOOLNND-GOHIFREVSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   18.3319   -3.0234    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.5256   -5.6559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7722   -4.4815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6437   -6.6570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9336   -3.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0701   -6.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1891   -7.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6137   -6.7196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9194   -5.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8005   -4.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3759   -4.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3448   -4.7813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2552   -3.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7270   -5.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6105   -5.9255    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1017   -6.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6332   -7.5468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1332   -7.5416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6747   -6.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 26  2  1  0
  2  3  2  0
  2  4  1  0
 25  5  1  0
  5  6  1  0
  5  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  4 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 22 21  1  0
 23 22  1  0
 21 23  1  0
 21 18  1  6
 23 24  1  1
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 25  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: 379.46

Molecular Weight (Monoisotopic): 379.1896

AlogP: 3.24

#Rotatable Bonds: 5

Polar Surface Area: 84.66

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.49

CX Basic pKa: 9.62

CX LogP: 2.66

CX LogD: 0.49

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.84

Np Likeness Score: -0.86

References

1. Rodriguez V, Valente S, Rovida S, Rotili D, Stazi G, Lucidi A, Ciossani G, Mattevi A, Botrugno OA, Dessanti P, Mercurio C, Vianello P, Minucci S, Varasi M, Mai A.  (2015)  Pyrrole- and indole-containing tranylcypromine derivatives as novel lysine-specific demethylase 1 inhibitors active on cancer cells,  6  (4): [10.1039/C4MD00507D]

Source

Source(1):

• Scientific Literature