Pyrrolidine-2-carboxylic acid [1-(carbamoylmethyl-carbamoyl)-3-phenyl-propyl]-amide

ID: ALA2370030

PubChem CID: 73351544

Max Phase: Preclinical

Molecular Formula: C17H24N4O3

Molecular Weight: 332.40

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  NC(=O)CNC(=O)[C@H](CCc1ccccc1)NC(=O)[C@H]1CCCN1

Standard InChI:  InChI=1S/C17H24N4O3/c18-15(22)11-20-16(23)14(9-8-12-5-2-1-3-6-12)21-17(24)13-7-4-10-19-13/h1-3,5-6,13-14,19H,4,7-11H2,(H2,18,22)(H,20,23)(H,21,24)/t13-,14+/m1/s1

Standard InChI Key:  RUUGHIGMBFKHMT-KGLIPLIRSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    4.4144   -0.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1141    0.3581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5383    0.4081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8387   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2712    0.0208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6997    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9485   -0.0417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6898    0.3206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4394   -0.8995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5133    1.2327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7247   -0.7538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8720   -0.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9751    0.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3993    0.4997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1723   -1.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1973   -2.1114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3780    0.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5774    1.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4977   -2.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9219   -2.4904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7653    1.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9511   -3.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5227   -3.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2515   -3.7523    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  6
  9  1  2  0
 10  3  2  0
 11  6  2  0
  4 12  1  6
 13  5  1  0
 14  6  1  0
 15 12  1  0
 16 15  1  0
 17  7  1  0
 18  8  1  0
 19 16  2  0
 20 16  1  0
 21 18  1  0
 22 20  2  0
 23 19  1  0
 24 22  1  0
 21 17  1  0
 23 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2370030

   (2R)-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-1-oxo-4-phenylbutan-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: 332.40

Molecular Weight (Monoisotopic): 332.1848

AlogP: -0.54

#Rotatable Bonds: 8

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: 12.41

CX Basic pKa: 9.50

CX LogP: -0.44

CX LogD: -2.52

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.51

Np Likeness Score: -0.31

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