N-((S)-1-((S)-1-amino-1-oxo-3-phenylpropan-2-ylamino)-5-guanidino-1-oxopentan-2-yl)-2,4-dichlorobenzamide

ID: ALA2208332

PubChem CID: 71454360

Max Phase: Preclinical

Molecular Formula: C22H26Cl2N6O3

Molecular Weight: 493.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)NCCC[C@H](NC(=O)c1ccc(Cl)cc1Cl)C(=O)N[C@@H](Cc1ccccc1)C(N)=O

Standard InChI:  InChI=1S/C22H26Cl2N6O3/c23-14-8-9-15(16(24)12-14)20(32)29-17(7-4-10-28-22(26)27)21(33)30-18(19(25)31)11-13-5-2-1-3-6-13/h1-3,5-6,8-9,12,17-18H,4,7,10-11H2,(H2,25,31)(H,29,32)(H,30,33)(H4,26,27,28)/t17-,18-/m0/s1

Standard InChI Key:  QVDDXGDCGATLNM-ROUUACIJSA-N

Molfile:  

     RDKit          2D

 33 34  0  0  0  0  0  0  0  0999 V2000
   16.7153  -29.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4230  -29.4024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0076  -29.4024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7153  -30.6282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0076  -28.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2999  -29.8110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5922  -29.4024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8844  -29.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5922  -28.5852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7153  -28.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7153  -27.3594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0076  -26.9508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0076  -26.1336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2999  -25.7250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7153  -25.7250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1307  -29.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8384  -29.4024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5461  -29.8110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8384  -28.5852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1307  -30.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8384  -31.0368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8339  -31.8550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5408  -32.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2495  -31.8549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2469  -31.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5394  -30.6286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1774  -29.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4702  -29.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4697  -30.6251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1824  -31.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8867  -30.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1792  -28.5819    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.7626  -31.0346    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  4  2  0
  3  5  1  1
  3  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
  2 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 16 20  1  6
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
  8 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31  8  1  0
 27 32  1  0
 29 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2208332

   Bz(2,4-diCl)-Arg-Phe-NH2

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 493.40

Molecular Weight (Monoisotopic): 492.1443

AlogP: 1.57

#Rotatable Bonds: 11

Polar Surface Area: 163.19

Molecular Species: BASE

HBA: 4

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.87

CX Basic pKa: 11.56

CX LogP: 1.33

CX LogD: -0.70

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.16

Np Likeness Score: -0.57

References

1. Gealageas R, Schneider S, Humbert JP, Bertin I, Schmitt M, Laboureyras E, Dugave C, Mollereau C, Simonnet G, Bourguignon JJ, Simonin F, Bihel F..  (2012)  Development of sub-nanomolar dipeptidic ligands of neuropeptide FF receptors.,  22  (24): [PMID:23131340] [10.1016/j.bmcl.2012.10.049]

Source

Source(1):

• Scientific Literature