(S)-N-((S)-1-((S)-2-carbamoylpyrrolidin-1-yl)-1-oxo-4-phenylbutan-2-yl)-5-oxopyrrolidine-2-carboxamide

ID: ALA3933726

PubChem CID: 10340115

Max Phase: Preclinical

Molecular Formula: C20H26N4O4

Molecular Weight: 386.45

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCc1ccccc1)NC(=O)[C@@H]1CCC(=O)N1

Standard InChI:  InChI=1S/C20H26N4O4/c21-18(26)16-7-4-12-24(16)20(28)15(9-8-13-5-2-1-3-6-13)23-19(27)14-10-11-17(25)22-14/h1-3,5-6,14-16H,4,7-12H2,(H2,21,26)(H,22,25)(H,23,27)/t14-,15-,16-/m0/s1

Standard InChI Key:  ZKGYSCIDBBYKKJ-JYJNAYRXSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    7.7834  -16.8293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4979  -16.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2124  -16.8293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9268  -16.4168    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2124  -17.6543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7834  -17.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0690  -18.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4979  -18.0668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3156  -17.7364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7636  -18.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1761  -19.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9830  -18.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9431  -18.2633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4979  -15.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6806  -16.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2326  -16.1342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8201  -15.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0131  -15.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8543  -17.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2427  -18.1076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6396  -17.8066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7834  -15.1793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7834  -14.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5002  -13.9437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5005  -13.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7855  -12.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0686  -13.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0719  -13.9459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  3  5  2  0
  1  6  1  0
  7  6  1  6
  6  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  7  1  0
 10 13  2  0
  2 14  1  0
  4 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18  4  1  0
 15 19  1  1
 19 20  1  0
 19 21  2  0
 14 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3933726

   H-Pyr-hPhe-Pro-NH2

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 386.45

Molecular Weight (Monoisotopic): 386.1954

AlogP: -0.14

#Rotatable Bonds: 7

Polar Surface Area: 121.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.43

CX Basic pKa: ┄

CX LogP: -0.40

CX LogD: -0.40

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.60

Np Likeness Score: -0.33

References

1.  (2010)  TRH-like peptide derivatives as inhibitors of the TRH-degrading ectoenzyme, 

Source

Source(1):

• Patent Bioactivity Data