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

ID: ALA2111600

PubChem CID: 71456156

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+/m1/s1

Standard InChI Key:  LKIKVUCBEUCKNC-ZACQAIPSSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  1  0  0  0  0  0999 V2000
    3.6492   -1.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9478   -1.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3632   -1.9708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8037   -1.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0772   -1.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8726   -2.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5177   -1.5449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6576   -2.2589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9456   -1.5324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6492   -0.7140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8726   -3.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8037   -2.7933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0772   -0.7307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9331   -0.7057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2317   -1.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1837   -1.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6596   -1.9457    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0710   -2.9854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2735   -4.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7912   -0.3131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8601   -5.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0877   -4.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5052   -0.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7787    0.5136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5010   -5.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2735   -5.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0877   -5.7661    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
  2  6  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
 16  2  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
 18  8  1  0
 26 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2111600

   (3S,4S)-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