1-(2-Acetylamino-3-hydroxy-propionyl)-pyrrolidine-2-carboxylic acid (1-{1-[1-(1-carbamoyl-2-methyl-propylcarbamoyl)-2-hydroxy-ethylcarbamoyl]-4-guanidino-butylcarbamoyl}-2-phenyl-ethyl)-amide

ID: ALA322058

PubChem CID: 14999611

Max Phase: Preclinical

Molecular Formula: C33H52N10O9

Molecular Weight: 732.84

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@@H](CO)C(=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/C33H52N10O9/c1-18(2)26(27(34)47)42-30(50)23(16-44)41-28(48)21(11-7-13-37-33(35)36)39-29(49)22(15-20-9-5-4-6-10-20)40-31(51)25-12-8-14-43(25)32(52)24(17-45)38-19(3)46/h4-6,9-10,18,21-26,44-45H,7-8,11-17H2,1-3H3,(H2,34,47)(H,38,46)(H,39,49)(H,40,51)(H,41,48)(H,42,50)(H4,35,36,37)/t21-,22-,23-,24-,25-,26-/m0/s1

Standard InChI Key:  YGIQYWFHBNWFHM-FRSCJGFNSA-N

Molfile:  

     RDKit          2D

 52 53  0  0  1  0  0  0  0  0999 V2000
    0.7042  -10.8500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917  -10.1292    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
    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
    0.7167   -9.3750    0.0000 C   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
    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
    2.8625  -11.1792    0.0000 N   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
    0.2542   -8.7042    0.0000 N   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
    5.6792  -11.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5625   -8.7750    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
   -0.4583  -10.1250    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
    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
   -1.0333   -8.0917    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
    0.1625  -11.4542    0.0000 C   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
    1.5292   -9.3167    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
    1.3667  -11.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9500   -8.6000    0.0000 O   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
    0.5667  -12.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9208   -9.5167    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
    9.2042  -12.4042    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
    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
  7  3  1  6
  4  5  1  0
  5 11  1  0
  6  2  1  0
  7  1  1  0
  8 15  1  0
  9 19  1  0
 10  9  1  0
 11 10  1  1
 12  3  1  0
 13  8  1  0
 14  4  1  6
 15 12  1  1
  6 16  1  1
 17 30  2  0
 18 14  1  0
 19 13  1  6
 20 16  1  0
 21 17  1  0
 22  2  2  0
 23  3  2  0
 24  5  2  0
 25  8  2  0
 26  9  2  0
 15 27  1  0
 28 18  2  0
 29 20  2  0
 30 44  1  0
 31 17  1  0
 32 18  1  0
 33  1  1  0
 14 34  1  0
  6 35  1  0
 36 27  1  0
 11 37  1  0
  7 38  1  0
 39 35  1  0
 40 37  1  0
 41 33  1  0
 42 20  1  0
 19 43  1  0
 44 49  1  0
 45 34  1  0
 46 34  1  0
 47 36  2  0
 48 36  1  0
 49 43  1  0
 50 48  2  0
 51 47  1  0
 52 50  1  0
 41 38  1  0
 51 52  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA322058

   Ac-Ser-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: 732.84

Molecular Weight (Monoisotopic): 732.3919

AlogP: -4.16

#Rotatable Bonds: 20

Polar Surface Area: 313.76

Molecular Species: BASE

HBA: 10

HBD: 10

#RO5 Violations: 2

HBA (Lipinski): 19

HBD (Lipinski): 13

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.53

CX Basic pKa: 10.78

CX LogP: -4.78

CX LogD: -6.86

Aromatic Rings: 1

Heavy Atoms: 52

QED Weighted: 0.03

Np Likeness Score: 0.10

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