1-(2-Acetylamino-3-hydroxy-propionyl)-pyrrolidine-2-carboxylic acid (1-carbamoyl-2-phenyl-ethyl)-amide

ID: ALA107589

PubChem CID: 14999615

Max Phase: Preclinical

Molecular Formula: C19H26N4O5

Molecular Weight: 390.44

Molecule Type: Protein

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H26N4O5/c1-12(25)21-15(11-24)19(28)23-9-5-8-16(23)18(27)22-14(17(20)26)10-13-6-3-2-4-7-13/h2-4,6-7,14-16,24H,5,8-11H2,1H3,(H2,20,26)(H,21,25)(H,22,27)/t14-,15-,16-/m0/s1

Standard InChI Key:  DHRVRZIBGLXCFX-JYJNAYRXSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  1  0  0  0  0  0999 V2000
    0.4250   -6.1625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0042   -5.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8750   -6.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4375   -4.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1667   -6.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5792   -6.4917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0250   -4.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792   -6.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9875   -6.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8458   -4.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7458   -5.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8542   -5.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792   -5.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9875   -7.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208   -3.4042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6917   -6.0875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1208   -6.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2500   -4.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -4.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0792   -7.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667   -3.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2875   -7.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2000   -4.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -4.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667   -3.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6750   -3.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9250   -3.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042   -3.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  5  3  1  6
  4  2  1  0
  5  1  1  0
  6  3  1  0
  4  7  1  1
  8  6  1  1
  9  8  1  0
 10  7  1  0
 11  2  2  0
 12  3  2  0
  8 13  1  0
 14  9  2  0
 15 10  2  0
 16  9  1  0
 17  1  1  0
  4 18  1  0
 19 13  1  0
  5 20  1  0
 21 18  1  0
 22 17  1  0
 23 10  1  0
 24 19  2  0
 25 19  1  0
 26 25  2  0
 27 24  1  0
 28 26  1  0
 22 20  1  0
 27 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA107589

   Ac-Ser-Pro-Phe-NH2

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: 390.44

Molecular Weight (Monoisotopic): 390.1903

AlogP: -1.31

#Rotatable Bonds: 8

Polar Surface Area: 141.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.93

CX Basic pKa: ┄

CX LogP: -1.76

CX LogD: -1.76

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.44

Np Likeness Score: -0.31

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