2-(2-Acetylamino-3-phenyl-propionylamino)-5-guanidino-pentanoic acid [1-(1-carbamoyl-2-methyl-propylcarbamoyl)-2-hydroxy-ethyl]-amide

ID: ALA104861

PubChem CID: 14999617

Max Phase: Preclinical

Molecular Formula: C25H40N8O6

Molecular Weight: 548.65

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  CC(=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/C25H40N8O6/c1-14(2)20(21(26)36)33-24(39)19(13-34)32-22(37)17(10-7-11-29-25(27)28)31-23(38)18(30-15(3)35)12-16-8-5-4-6-9-16/h4-6,8-9,14,17-20,34H,7,10-13H2,1-3H3,(H2,26,36)(H,30,35)(H,31,38)(H,32,37)(H,33,39)(H4,27,28,29)/t17-,18-,19-,20-/m0/s1

Standard InChI Key:  FZNDNGDITYPGLU-MUGJNUQGSA-N

Molfile:  

     RDKit          2D

 39 39  0  0  1  0  0  0  0  0999 V2000
    9.2042  -10.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5000  -11.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2667  -11.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3875  -10.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0917  -11.1792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7917  -10.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9750  -10.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9042  -11.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667  -10.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0917  -14.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6125  -10.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8625  -11.1792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792  -11.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1542  -10.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7917  -14.8417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5000  -11.9917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2667  -11.9917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3875   -9.9542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667   -9.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6125   -9.9542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1417   -9.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0917  -13.6167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3875  -14.8417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3167  -11.1792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9042  -11.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9750   -9.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7917   -9.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5000   -9.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4500  -11.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792  -11.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3875  -13.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6125  -12.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2042  -12.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8000   -9.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -8.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3875  -12.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542   -7.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2042   -8.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -7.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  7  1  0
  4  5  1  0
  5  6  1  0
  6  2  1  0
  7 13  1  0
  8  1  1  0
  9  3  1  0
 10 22  2  0
 11  8  1  0
 12  9  1  0
 13  4  1  0
 14 12  1  0
 15 10  1  0
 16  2  2  0
 17  3  2  0
 18  4  2  0
  9 19  1  1
 20 11  2  0
 21 14  2  0
 22 31  1  0
 23 10  1  0
 24 11  1  0
  8 25  1  6
 26 19  1  0
  6 27  1  1
 28 27  1  0
 29 14  1  0
 13 30  1  6
 31 36  1  0
 32 25  1  0
 33 25  1  0
 34 26  2  0
 35 26  1  0
 36 30  1  0
 37 35  2  0
 38 34  1  0
 39 37  1  0
 38 39  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA104861

   Ac-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: 548.65

Molecular Weight (Monoisotopic): 548.3071

AlogP: -2.62

#Rotatable Bonds: 16

Polar Surface Area: 244.12

Molecular Species: BASE

HBA: 7

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.74

CX Basic pKa: 15.77

CX LogP: -2.90

CX LogD: -5.02

Aromatic Rings: 1

Heavy Atoms: 39

QED Weighted: 0.06

Np Likeness Score: 0.32

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