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

ID: ALA2208335

PubChem CID: 10184880

Max Phase: Preclinical

Molecular Formula: C23H30N6O4

Molecular Weight: 454.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc2ccccc2)C(N)=O)cc1

Standard InChI:  InChI=1S/C23H30N6O4/c1-33-17-11-9-16(10-12-17)21(31)28-18(8-5-13-27-23(25)26)22(32)29-19(20(24)30)14-15-6-3-2-4-7-15/h2-4,6-7,9-12,18-19H,5,8,13-14H2,1H3,(H2,24,30)(H,28,31)(H,29,32)(H4,25,26,27)/t18-,19-/m0/s1

Standard InChI Key:  XDLDWLLAJBXAFU-OALUTQOASA-N

Molfile:  

     RDKit          2D

 33 34  0  0  0  0  0  0  0  0999 V2000
    5.9473  -14.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6550  -13.6611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2396  -13.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9473  -14.8869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2396  -12.8439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5319  -14.0697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8242  -13.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1165  -14.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8242  -12.8439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9473  -12.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9473  -11.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2396  -11.2096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2396  -10.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5319   -9.9838    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9473   -9.9838    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3628  -14.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0705  -13.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7782  -14.0697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0705  -12.8439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3628  -14.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0705  -15.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0660  -16.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7729  -16.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4815  -16.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4789  -15.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7715  -14.8874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4095  -13.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7022  -14.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7018  -14.8838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4145  -15.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1188  -14.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9946  -15.2933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2864  -14.8857    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
 29 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2208335

   Bz(4-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: 12.17

CX Basic pKa: 11.73

CX LogP: 0.00

CX LogD: -2.07

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.15

Np Likeness Score: -0.20

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