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

ID: ALA2208333

PubChem CID: 71459819

Max Phase: Preclinical

Molecular Formula: C23H30N6O4

Molecular Weight: 454.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc1ccccc1)C(N)=O

Standard InChI:  InChI=1S/C23H30N6O4/c1-33-19-12-6-5-10-16(19)21(31)28-17(11-7-13-27-23(25)26)22(32)29-18(20(24)30)14-15-8-3-2-4-9-15/h2-6,8-10,12,17-18H,7,11,13-14H2,1H3,(H2,24,30)(H,28,31)(H,29,32)(H4,25,26,27)/t17-,18-/m0/s1

Standard InChI Key:  HCHKOIZJWXHBPQ-ROUUACIJSA-N

Molfile:  

     RDKit          2D

 33 34  0  0  0  0  0  0  0  0999 V2000
    5.8813   -5.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5890   -5.2168    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1736   -5.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8813   -6.4426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1736   -4.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4659   -5.6254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7582   -5.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0505   -5.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7582   -4.3996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8813   -3.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8813   -3.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1736   -2.7652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1736   -1.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4659   -1.5395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8813   -1.5395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2967   -5.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0044   -5.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7121   -5.6254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0044   -4.3996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2967   -6.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0044   -6.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9999   -7.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7068   -8.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4155   -7.6693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4129   -6.8479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7054   -6.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3434   -5.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6362   -5.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6358   -6.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3485   -6.8479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0528   -6.4377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3452   -4.3963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6384   -3.9862    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  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
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2208333

   Bz(2-OMe)-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: 454.53

Molecular Weight (Monoisotopic): 454.2329

AlogP: 0.27

#Rotatable Bonds: 12

Polar Surface Area: 172.42

Molecular Species: BASE

HBA: 5

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.28

CX Basic pKa: 11.74

CX LogP: 0.02

CX LogD: -2.07

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.15

Np Likeness Score: -0.26

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