Pyrrolidine-2-carboxylic acid [1-(carbamoylmethyl-carbamoyl)-2-phenyl-ethyl]-amide

ID: ALA2372917

Cas Number: 114390-34-0

PubChem CID: 9973171

Max Phase: Preclinical

Molecular Formula: C16H22N4O3

Molecular Weight: 318.38

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  NC(=O)CNC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H]1CCCN1

Standard InChI:  InChI=1S/C16H22N4O3/c17-14(21)10-19-15(22)13(9-11-5-2-1-3-6-11)20-16(23)12-7-4-8-18-12/h1-3,5-6,12-13,18H,4,7-10H2,(H2,17,21)(H,19,22)(H,20,23)/t12-,13-/m0/s1

Standard InChI Key:  QQGCHENFDLCECR-STQMWFEESA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    4.1023   -0.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8020    0.1999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2263    0.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5267   -0.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9510   -0.1416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3837   -0.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6280   -0.2041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3735    0.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1273   -1.0537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5517   -1.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2014    1.0745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4128   -0.9163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6590    0.2957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0875    0.3456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1393   -1.7242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0658    0.3956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2652    0.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3105   -1.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5392   -2.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4531    1.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1268   -3.1403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8899   -2.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3022   -3.1403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  4  1  0
  4  2  1  0
  5  3  1  0
  6 13  1  0
  7  8  1  0
  8  1  1  1
  9  1  2  0
  4 10  1  6
 11  3  2  0
 12  6  2  0
 13  5  1  0
 14  6  1  0
 15 10  1  0
 16  7  1  0
 17  8  1  0
 18 15  2  0
 19 15  1  0
 20 17  1  0
 21 19  2  0
 22 18  1  0
 23 21  1  0
 20 16  1  0
 22 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2372917

   (S)-N-((S)-1-((2-Amino-2-oxoethyl)amino)-1-oxo-3-phenylpropan-2-yl)pyrrolidine-2-carboxamide

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: 318.38

Molecular Weight (Monoisotopic): 318.1692

AlogP: -0.93

#Rotatable Bonds: 7

Polar Surface Area: 113.32

Molecular Species: BASE

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.32

CX Basic pKa: 9.50

CX LogP: -0.89

CX LogD: -2.97

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.52

Np Likeness Score: -0.43

References

1. Johnson RL, Bontems RJ, Yang KE, Mishra RK..  (1990)  Synthesis and biological evaluation of analogues of Pro-Leu-Gly-NH2 modified at the leucyl residue.,  33  (6): [PMID:1971310] [10.1021/jm00168a045]

Source

Source(1):

• Scientific Literature