1-Acetyl-pyrrolidine-2-carboxylic acid {1-[1-(1-carbamoyl-2-hydroxy-ethylcarbamoyl)-4-guanidino-butylcarbamoyl]-2-phenyl-ethyl}-amide

ID: ALA321324

PubChem CID: 14999605

Max Phase: Preclinical

Molecular Formula: C25H38N8O6

Molecular Weight: 546.63

Molecule Type: Protein

Names and Identifiers

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

Standard InChI:  InChI=1S/C25H38N8O6/c1-15(35)33-12-6-10-20(33)24(39)31-18(13-16-7-3-2-4-8-16)23(38)30-17(9-5-11-29-25(27)28)22(37)32-19(14-34)21(26)36/h2-4,7-8,17-20,34H,5-6,9-14H2,1H3,(H2,26,36)(H,30,38)(H,31,39)(H,32,37)(H4,27,28,29)/t17-,18-,19-,20-/m0/s1

Standard InChI Key:  XAWXSQISJXUZIM-MUGJNUQGSA-N

Molfile:  

     RDKit          2D

 39 40  0  0  1  0  0  0  0  0999 V2000
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   -0.4333   -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
   -1.1458   -3.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917   -3.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5000   -3.6542    0.0000 N   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
    5.2042   -3.2417    0.0000 C   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
   -2.3000   -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
    5.9042   -3.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5000   -6.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0875   -3.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2042   -7.3167    0.0000 N   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
    1.6792   -4.4667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917   -2.4292    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
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    4.5000   -6.0917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917   -7.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6125   -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
    5.2042   -2.4292    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
    5.9042   -2.0250    0.0000 O   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
    3.0875   -4.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917   -5.6875    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
    3.7917   -4.8750    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
  4  2  1  6
  3 11  1  0
  4  1  1  0
  5 14  1  0
  6  5  1  0
  7  2  1  0
  8  6  1  1
  9  3  1  0
 10  1  1  0
 11  7  1  1
 12  8  1  0
 13 22  2  0
 14  9  1  6
 15 13  1  0
 16  2  2  0
 17  3  2  0
 18  5  2  0
 11 19  1  0
 20 10  2  0
 21 12  2  0
 22 33  1  0
 23 13  1  0
 24 12  1  0
 25  1  1  0
 26 19  1  0
  8 27  1  0
  4 28  1  0
 29 10  1  0
 30 27  1  0
 31 25  1  0
 14 32  1  0
 33 36  1  0
 34 26  2  0
 35 26  1  0
 36 32  1  0
 37 35  2  0
 38 34  1  0
 39 37  1  0
 31 28  1  0
 38 39  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA321324

   Ac-Pro-Phe-Arg-Ser-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: 546.63

Molecular Weight (Monoisotopic): 546.2914

AlogP: -2.77

#Rotatable Bonds: 14

Polar Surface Area: 235.33

Molecular Species: BASE

HBA: 7

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.73

CX Basic pKa: 10.78

CX LogP: -3.52

CX LogD: -5.63

Aromatic Rings: 1

Heavy Atoms: 39

QED Weighted: 0.07

Np Likeness Score: 0.09

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