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

ID: ALA322972

PubChem CID: 14999608

Max Phase: Preclinical

Molecular Formula: C20H31N7O5

Molecular Weight: 449.51

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(N)=O

Standard InChI:  InChI=1S/C20H31N7O5/c1-12(29)25-15(10-13-6-3-2-4-7-13)19(32)26-14(8-5-9-24-20(22)23)18(31)27-16(11-28)17(21)30/h2-4,6-7,14-16,28H,5,8-11H2,1H3,(H2,21,30)(H,25,29)(H,26,32)(H,27,31)(H4,22,23,24)/t14-,15-,16-/m0/s1

Standard InChI Key:  HVLFXNHKZMVSAK-JYJNAYRXSA-N

Molfile:  

     RDKit          2D

 32 32  0  0  1  0  0  0  0  0999 V2000
    2.2125   -3.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0292   -3.1917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7375   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9167   -2.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4417   -3.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5042   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0292   -6.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8042   -3.1917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -3.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1000   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7375   -6.8542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2125   -4.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292   -1.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5042   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4417   -4.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0792   -1.9250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0292   -5.6292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292   -6.8542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1417   -2.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -1.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7375   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4417   -1.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6083   -3.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -4.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292   -5.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7417   -1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917   -0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292   -4.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9000    0.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500   -0.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292    0.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 10  1  0
  3  2  1  0
  4  3  1  0
  5  1  1  0
  6  4  1  0
  7  1  1  0
  8 18  2  0
  9  7  1  0
 10  5  1  0
 11  9  1  0
 12  8  1  0
 13  1  2  0
 14  2  2  0
  7 15  1  1
 16  6  2  0
 17 11  2  0
 18 26  1  0
 19  8  1  0
 20  6  1  0
 21 15  1  0
  4 22  1  1
 23 22  1  0
 24 11  1  0
 10 25  1  6
 26 29  1  0
 27 21  2  0
 28 21  1  0
 29 25  1  0
 30 28  2  0
 31 27  1  0
 32 30  1  0
 31 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA322972

   Ac-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: 449.51

Molecular Weight (Monoisotopic): 449.2387

AlogP: -2.77

#Rotatable Bonds: 13

Polar Surface Area: 215.02

Molecular Species: BASE

HBA: 6

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.87

CX Basic pKa: 10.79

CX LogP: -3.24

CX LogD: -5.37

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.10

Np Likeness Score: 0.38

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