1-Acetyl-pyrrolidine-2-carboxylic acid (1-carbamoyl-2-phenyl-ethyl)-amide

ID: ALA323292

Cas Number: 60240-12-2

PubChem CID: 14999607

Max Phase: Preclinical

Molecular Formula: C16H21N3O3

Molecular Weight: 303.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(N)=O

Standard InChI:  InChI=1S/C16H21N3O3/c1-11(20)19-9-5-8-14(19)16(22)18-13(15(17)21)10-12-6-3-2-4-7-12/h2-4,6-7,13-14H,5,8-10H2,1H3,(H2,17,21)(H,18,22)/t13-,14-/m0/s1

Standard InChI Key:  RDPDQECNGQFLDW-KBPBESRZSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  1  0  0  0  0  0999 V2000
   -1.8833   -3.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4333   -3.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1458   -3.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2667   -3.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3000   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9750   -3.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6792   -3.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4500   -2.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9750   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0500   -2.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6792   -4.4667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792   -3.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4333   -3.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3792   -1.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2250   -4.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8708   -1.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0208   -4.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042   -1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9625   -1.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -0.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1917   -0.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  6
  3  1  1  0
  4  2  1  0
  5  1  1  0
  6  4  1  1
  7  6  1  0
  8  2  2  0
  6  9  1  0
 10  5  2  0
 11  7  2  0
 12  7  1  0
 13  1  1  0
 14  9  1  0
  3 15  1  0
 16  5  1  0
 17 13  1  0
 18 14  2  0
 19 14  1  0
 20 19  2  0
 21 18  1  0
 22 20  1  0
 17 15  1  0
 21 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA323292

   1-Acetyl-L-prolyl-L-phenylalaninamide

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: 303.36

Molecular Weight (Monoisotopic): 303.1583

AlogP: 0.21

#Rotatable Bonds: 5

Polar Surface Area: 92.50

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.49

CX Basic pKa: ┄

CX LogP: -0.17

CX LogD: -0.17

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.81

Np Likeness Score: -0.64

References

1. Deshpande MS, Burton J..  (1992)  Mapping the binding site of tissue kallikrein: preparation and testing of all possible substrate analog inhibitors homologous with the sequence of kininogen between Ser386 and Gln392.,  35  (17): [PMID:1507198] [10.1021/jm00095a002]

Source

Source(1):

• Scientific Literature