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

ID: ALA316580

PubChem CID: 14999609

Max Phase: Preclinical

Molecular Formula: C25H38N8O6

Molecular Weight: 546.63

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(N)=O

Standard InChI:  InChI=1S/C25H38N8O6/c1-15(35)30-19(14-34)24(39)33-12-6-10-20(33)23(38)32-18(13-16-7-3-2-4-8-16)22(37)31-17(21(26)36)9-5-11-29-25(27)28/h2-4,7-8,17-20,34H,5-6,9-14H2,1H3,(H2,26,36)(H,30,35)(H,31,37)(H,32,38)(H4,27,28,29)/t17-,18-,19-,20-/m0/s1

Standard InChI Key:  AXGKGVPTHDXLPD-MUGJNUQGSA-N

Molfile:  

     RDKit          2D

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    2.6667   -3.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7792   -3.9042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9458   -4.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3583   -1.3250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3667   -4.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792   -5.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4917   -1.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0792   -5.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  0
  5  3  1  6
  4  2  1  0
  5  1  1  0
  6  9  1  0
  7  3  1  0
  8  6  1  0
  9  7  1  1
  4 10  1  1
 11 22  2  0
 12 14  1  0
 13 10  1  0
 14  8  1  6
 15 11  1  0
 16  2  2  0
 17  3  2  0
 18  6  2  0
  9 19  1  0
 20 12  2  0
 21 13  2  0
 22 33  1  0
 23 11  1  0
 24 12  1  0
 25  1  1  0
  4 26  1  0
 27 19  1  0
  5 28  1  0
 29 26  1  0
 30 25  1  0
 31 13  1  0
 14 32  1  0
 33 36  1  0
 34 27  2  0
 35 27  1  0
 36 32  1  0
 37 35  2  0
 38 34  1  0
 39 37  1  0
 30 28  1  0
 38 39  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA316580

   Ac-Ser-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: 546.63

Molecular Weight (Monoisotopic): 546.2914

AlogP: -2.77

#Rotatable Bonds: 14

Polar Surface Area: 235.33

Molecular Species: BASE

HBA: 7

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.75

CX Basic pKa: 12.69

CX LogP: -3.58

CX LogD: -5.64

Aromatic Rings: 1

Heavy Atoms: 39

QED Weighted: 0.07

Np Likeness Score: 0.13

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