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

ID: ALA321719

PubChem CID: 14999604

Max Phase: Preclinical

Molecular Formula: C30H47N9O7

Molecular Weight: 645.76

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(=O)N[C@H](C(N)=O)C(C)C

Standard InChI:  InChI=1S/C30H47N9O7/c1-17(2)24(25(31)42)38-28(45)22(16-40)37-26(43)20(11-7-13-34-30(32)33)35-27(44)21(15-19-9-5-4-6-10-19)36-29(46)23-12-8-14-39(23)18(3)41/h4-6,9-10,17,20-24,40H,7-8,11-16H2,1-3H3,(H2,31,42)(H,35,44)(H,36,46)(H,37,43)(H,38,45)(H4,32,33,34)/t20-,21-,22-,23-,24-/m0/s1

Standard InChI Key:  RORHPEIEQZFKGK-LSBAASHUSA-N

Molfile:  

     RDKit          2D

 46 47  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
    6.6125   -3.2417    0.0000 N   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
    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
    5.2042   -3.2417    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
    2.3792   -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
    7.3167   -3.6542    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
    4.5000   -6.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0167   -3.2417    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
    5.9042   -4.4667    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
    8.0167   -2.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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
    8.7292   -3.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3167   -4.4667    0.0000 C   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
    8.0167   -4.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6125   -4.8750    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
  6  2  1  6
  3  4  1  0
  4  9  1  0
  5 14  1  0
  6  1  1  0
  7 17  1  0
  8  7  1  0
  9  8  1  1
 10  2  1  0
 11  5  1  0
 12  1  1  0
 13  3  1  6
 14 10  1  1
 15 26  2  0
 16 13  1  0
 17 11  1  6
 18 15  1  0
 19  2  2  0
 20  4  2  0
 21  5  2  0
 22  7  2  0
 14 23  1  0
 24 12  2  0
 25 16  2  0
 26 38  1  0
 27 15  1  0
 28 16  1  0
 13 29  1  0
 30  1  1  0
 31 23  1  0
  9 32  1  0
  6 33  1  0
 34 12  1  0
 35 32  1  0
 36 30  1  0
 17 37  1  0
 38 43  1  0
 39 29  1  0
 40 29  1  0
 41 31  2  0
 42 31  1  0
 43 37  1  0
 44 42  2  0
 45 41  1  0
 46 44  1  0
 36 33  1  0
 45 46  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA321719

   Ac-Pro-Phe-Arg-Ser-Val-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: 645.76

Molecular Weight (Monoisotopic): 645.3598

AlogP: -2.63

#Rotatable Bonds: 17

Polar Surface Area: 264.43

Molecular Species: BASE

HBA: 8

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.64

CX Basic pKa: 10.77

CX LogP: -3.18

CX LogD: -5.28

Aromatic Rings: 1

Heavy Atoms: 46

QED Weighted: 0.05

Np Likeness Score: 0.08

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