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

ID: ALA104918

PubChem CID: 14999613

Max Phase: Preclinical

Molecular Formula: C16H31N7O5

Molecular Weight: 401.47

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  CC(=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/C16H31N7O5/c1-8(2)12(13(17)26)23-15(28)11(7-24)22-14(27)10(21-9(3)25)5-4-6-20-16(18)19/h8,10-12,24H,4-7H2,1-3H3,(H2,17,26)(H,21,25)(H,22,27)(H,23,28)(H4,18,19,20)/t10-,11-,12-/m0/s1

Standard InChI Key:  NIYNFIBEISWDIC-SRVKXCTJSA-N

Molfile:  

     RDKit          2D

 28 27  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
    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
    9.9042  -11.1792    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
    4.9750  -10.7750    0.0000 N   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
    5.6792  -11.1792    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
    6.3875   -9.9542    0.0000 O   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
    4.2667  -11.9917    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
    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
    3.5667  -10.7750    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
    6.3875  -12.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  4  1  0
  4  5  1  0
  5  2  1  0
  6  1  1  0
  7 17  2  0
  8  6  1  0
  9 11  1  0
 10  9  1  0
 11  3  1  0
 12  7  1  0
 13  2  2  0
 14  3  2  0
 15  8  2  0
 16 10  2  0
 17 25  1  0
 18  7  1  0
 19  8  1  0
  6 20  1  6
  5 21  1  1
 22 21  1  0
 23 10  1  0
 11 24  1  6
 25 28  1  0
 26 20  1  0
 27 20  1  0
 28 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA104918

   Ac-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: 401.47

Molecular Weight (Monoisotopic): 401.2387

AlogP: -3.35

#Rotatable Bonds: 12

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: 11.90

CX Basic pKa: 10.87

CX LogP: -4.04

CX LogD: -6.14

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.10

Np Likeness Score: 0.53

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