2-oxo-1-phenyl-N-(2-(thiophen-2-yl)ethyl)pyrrolidine-3-carboxamide

ID: ALA4568227

PubChem CID: 20964219

Max Phase: Preclinical

Molecular Formula: C17H18N2O2S

Molecular Weight: 314.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NCCc1cccs1)C1CCN(c2ccccc2)C1=O

Standard InChI:  InChI=1S/C17H18N2O2S/c20-16(18-10-8-14-7-4-12-22-14)15-9-11-19(17(15)21)13-5-2-1-3-6-13/h1-7,12,15H,8-11H2,(H,18,20)

Standard InChI Key:  NUHVNPAAEPGUFR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   10.4609  -10.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4597  -11.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1745  -12.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8909  -11.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8880  -10.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1727  -10.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1643   -9.6028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8303   -9.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5730   -8.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7480   -8.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4955   -9.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6156   -9.3683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2831   -7.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0016   -8.3175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2747   -7.0874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7119   -7.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4304   -8.3030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4388   -9.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7800   -9.6212    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.0429  -10.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8679  -10.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1147   -9.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  7  1  0
  6  7  1  0
  8 12  2  0
  9 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4568227

   2-Oxo-1-phenylpyrrolidine-3-carboxylic acid (2-thiophen-2-ylethyl)amide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 314.41

Molecular Weight (Monoisotopic): 314.1089

AlogP: 2.46

#Rotatable Bonds: 5

Polar Surface Area: 49.41

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.38

CX LogD: 2.38

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.86

Np Likeness Score: -2.17

References

1. Heinrich T, Seenisamy J, Blume B, Bomke J, Calderini M, Eckert U, Friese-Hamim M, Kohl R, Lehmann M, Leuthner B, Musil D, Rohdich F, Zenke FT..  (2019)  Discovery and Structure-Based Optimization of Next-Generation Reversible Methionine Aminopeptidase-2 (MetAP-2) Inhibitors.,  62  (10): [PMID:30939017] [10.1021/acs.jmedchem.9b00041]

Source

Source(1):

• Scientific Literature