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

ID: ALA431813

PubChem CID: 14999606

Max Phase: Preclinical

Molecular Formula: C22H33N7O4

Molecular Weight: 459.55

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(N)=O

Standard InChI:  InChI=1S/C22H33N7O4/c1-14(30)29-12-6-10-18(29)21(33)28-17(13-15-7-3-2-4-8-15)20(32)27-16(19(23)31)9-5-11-26-22(24)25/h2-4,7-8,16-18H,5-6,9-13H2,1H3,(H2,23,31)(H,27,32)(H,28,33)(H4,24,25,26)/t16-,17-,18-/m0/s1

Standard InChI Key:  BVRBTAJCMBNWCB-BZSNNMDCSA-N

Molfile:  

     RDKit          2D

 33 34  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
    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
    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
    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
    3.7917   -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
    1.6792   -4.4667    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
    3.7917   -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
    4.5000   -3.6542    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
   -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
   -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  8  1  0
  4  1  1  0
  5  2  1  0
  6  3  1  0
  7  1  1  0
  8  5  1  1
  9 18  2  0
 10 11  1  0
 11  6  1  6
 12  9  1  0
 13  2  2  0
 14  3  2  0
  8 15  1  0
 16  7  2  0
 17 10  2  0
 18 27  1  0
 19  9  1  0
 20 10  1  0
 21  1  1  0
 22 15  1  0
  4 23  1  0
 24  7  1  0
 25 21  1  0
 11 26  1  0
 27 30  1  0
 28 22  2  0
 29 22  1  0
 30 26  1  0
 31 29  2  0
 32 28  1  0
 33 31  1  0
 25 23  1  0
 32 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA431813

   Ac-Pro-Phe-Arg-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: 459.55

Molecular Weight (Monoisotopic): 459.2594

AlogP: -1.25

#Rotatable Bonds: 11

Polar Surface Area: 186.00

Molecular Species: BASE

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.13

CX Basic pKa: 10.97

CX LogP: -1.98

CX LogD: -4.06

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.16

Np Likeness Score: -0.01

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