4-Benzyl-pyrrolidine-3-carboxylic acid [1-(carbamoylmethyl-carbamoyl)-3-methyl-butyl]-amide

ID: ALA2111599

PubChem CID: 10407072

Max Phase: Preclinical

Molecular Formula: C20H30N4O3

Molecular Weight: 374.49

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H30N4O3/c1-13(2)8-17(20(27)23-12-18(21)25)24-19(26)16-11-22-10-15(16)9-14-6-4-3-5-7-14/h3-7,13,15-17,22H,8-12H2,1-2H3,(H2,21,25)(H,23,27)(H,24,26)/t15-,16-,17-/m0/s1

Standard InChI Key:  LKIKVUCBEUCKNC-ULQDDVLXSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  1  0  0  0  0  0999 V2000
    5.1000   -4.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4000   -4.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8250   -4.5875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2542   -4.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5417   -4.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -4.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9625   -4.1625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5250   -5.6000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3917   -4.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1000   -3.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2250   -3.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2542   -5.4042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5292   -3.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3917   -3.3250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6792   -4.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -5.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1167   -4.5625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1125   -4.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2250   -2.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2375   -2.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9375   -2.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000   -2.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9542   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2375   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000   -1.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292   -1.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  3  1  1  0
  4  5  1  0
  5  3  1  1
  6  2  1  0
  7  4  1  0
  8 16  1  0
  9 15  1  0
 10  1  2  0
  6 11  1  6
 12  4  2  0
  5 13  1  0
 14  9  2  0
 15  7  1  0
  2 16  1  0
  9 17  1  0
 18  6  1  0
 19 11  1  0
 20 13  1  0
 21 19  2  0
 22 19  1  0
 23 20  1  0
 24 20  1  0
 25 22  2  0
 26 21  1  0
 27 25  1  0
  8 18  1  0
 26 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2111599

   (3R,4R)-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]-4-benzylpyrrolidine-3-carboxamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 374.49

Molecular Weight (Monoisotopic): 374.2318

AlogP: 0.20

#Rotatable Bonds: 9

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: 12.57

CX Basic pKa: 10.38

CX LogP: 0.34

CX LogD: -2.45

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.49

Np Likeness Score: -0.22

References

1. Thomas C, Ohnmacht U, Niger M, Gmeiner P..  (1998)  Beta-analogs of PLG (L-prolyl-L-leucyl-glycinamide): ex-chiral pool syntheses and dopamine D2 receptor modulating effects.,  8  (20): [PMID:9873642] [10.1016/s0960-894x(98)00507-1]

Source

Source(1):

• Scientific Literature