N-((R)-1-((S)-1-amino-1-oxo-3-phenylpropan-2-ylamino)-5-guanidino-1-oxopentan-2-yl)benzamide

ID: ALA2208340

PubChem CID: 71463279

Max Phase: Preclinical

Molecular Formula: C22H28N6O3

Molecular Weight: 424.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)NCCC[C@@H](NC(=O)c1ccccc1)C(=O)N[C@@H](Cc1ccccc1)C(N)=O

Standard InChI:  InChI=1S/C22H28N6O3/c23-19(29)18(14-15-8-3-1-4-9-15)28-21(31)17(12-7-13-26-22(24)25)27-20(30)16-10-5-2-6-11-16/h1-6,8-11,17-18H,7,12-14H2,(H2,23,29)(H,27,30)(H,28,31)(H4,24,25,26)/t17-,18+/m1/s1

Standard InChI Key:  AYCCDRRQDKILDD-MSOLQXFVSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
   16.3521   -5.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0598   -4.7339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6444   -4.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3521   -5.9597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6444   -3.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9367   -5.1425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2290   -4.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5212   -5.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2290   -3.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3521   -3.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3521   -2.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6444   -2.2824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6444   -1.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9367   -1.0566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3521   -1.0566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7675   -5.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4752   -4.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1829   -5.1425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4752   -3.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7675   -5.9597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4752   -6.3683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4707   -7.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1776   -7.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8863   -7.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8837   -6.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1762   -5.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8142   -4.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1070   -5.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1065   -5.9566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8192   -6.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5235   -5.9548    0.0000 C   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  6
  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
M  END

Alternative Forms

1. Parent:

   

   ALA2208340

   Bz-D-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: 424.51

Molecular Weight (Monoisotopic): 424.2223

AlogP: 0.26

#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: 12.41

CX Basic pKa: 11.80

CX LogP: 0.18

CX LogD: -1.91

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.17

Np Likeness Score: -0.15

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