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

ID: ALA2372914

PubChem CID: 14654694

Max Phase: Preclinical

Molecular Formula: C15H20N4O3

Molecular Weight: 304.35

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H]1CCCN1)c1ccccc1

Standard InChI:  InChI=1S/C15H20N4O3/c16-12(20)9-18-15(22)13(10-5-2-1-3-6-10)19-14(21)11-7-4-8-17-11/h1-3,5-6,11,13,17H,4,7-9H2,(H2,16,20)(H,18,22)(H,19,21)/t11-,13-/m0/s1

Standard InChI Key:  OHRIFHPVTUDFDC-AAEUAGOBSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    5.1135    0.3581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4140   -0.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8381   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5377    0.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2705    0.0208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6988    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9482   -0.0417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6894    0.3206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4390   -0.8994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5127    1.2325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8714   -0.8537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7238   -0.7537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9743    0.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3984    0.4997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3777    0.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5751   -1.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1468   -1.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5770    1.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7650    1.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1218   -2.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5502   -2.1029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8256   -2.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  3  1  0
  5  4  1  0
  6 13  1  0
  7  8  1  0
  8  2  1  1
  9  2  2  0
 10  4  2  0
  3 11  1  6
 12  6  2  0
 13  5  1  0
 14  6  1  0
 15  7  1  0
 16 11  2  0
 17 11  1  0
 18  8  1  0
 19 18  1  0
 20 17  2  0
 21 16  1  0
 22 20  1  0
 19 15  1  0
 22 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2372914

   (2S)-N-[(1S)-2-[(2-amino-2-oxoethyl)amino]-2-oxo-1-phenylethyl]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: 304.35

Molecular Weight (Monoisotopic): 304.1535

AlogP: -0.80

#Rotatable Bonds: 6

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: 11.97

CX Basic pKa: 9.50

CX LogP: -1.18

CX LogD: -3.26

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.55

Np Likeness Score: -0.72

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