(S)-3-Hydroxy-2-oxo-1-phenylpyrrolidine-3-carboxylic Acid (2-Thiophen-2-ylethyl)amide

ID: ALA4566670

PubChem CID: 56959820

Max Phase: Preclinical

Molecular Formula: C17H18N2O3S

Molecular Weight: 330.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NCCc1cccs1)[C@@]1(O)CCN(c2ccccc2)C1=O

Standard InChI:  InChI=1S/C17H18N2O3S/c20-15(18-10-8-14-7-4-12-23-14)17(22)9-11-19(16(17)21)13-5-2-1-3-6-13/h1-7,12,22H,8-11H2,(H,18,20)/t17-/m0/s1

Standard InChI Key:  FZATYXICMFSLHR-KRWDZBQOSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   11.0327   -3.2956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8327   -3.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6204   -2.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5480   -6.0205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5468   -6.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2616   -7.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9779   -6.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9751   -6.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2598   -5.6077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2514   -4.7818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9174   -4.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6601   -3.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5826   -4.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7988   -4.5563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2053   -2.1294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8241   -2.4956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0015   -2.3451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5864   -1.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3827   -1.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6804   -2.7482    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.5043   -2.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7200   -1.9109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0293   -1.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
 10 11  1  0
 11 12  1  0
 12  2  1  0
  2 13  1  0
 13 10  1  0
  9 10  1  0
 13 14  2  0
  3 15  1  0
  3 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 19  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4566670

   (3~{S})-3-oxidanyl-2-oxidanylidene-1-phenyl-~{N}-(2-thiophen-2-ylethyl)pyrrolidine-3-carboxamide

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: 330.41

Molecular Weight (Monoisotopic): 330.1038

AlogP: 1.57

#Rotatable Bonds: 5

Polar Surface Area: 69.64

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.77

CX Basic pKa: ┄

CX LogP: 1.56

CX LogD: 1.56

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.82

Np Likeness Score: -1.24

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