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

ID: ALA2208336

PubChem CID: 71450765

Max Phase: Preclinical

Molecular Formula: C24H32N6O5

Molecular Weight: 484.56

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)cc1OC

Standard InChI:  InChI=1S/C24H32N6O5/c1-34-19-11-10-16(14-20(19)35-2)22(32)29-17(9-6-12-28-24(26)27)23(33)30-18(21(25)31)13-15-7-4-3-5-8-15/h3-5,7-8,10-11,14,17-18H,6,9,12-13H2,1-2H3,(H2,25,31)(H,29,32)(H,30,33)(H4,26,27,28)/t17-,18-/m0/s1

Standard InChI Key:  VROVWYHTEPXFBG-ROUUACIJSA-N

Molfile:  

     RDKit          2D

 35 36  0  0  0  0  0  0  0  0999 V2000
   17.3467  -13.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0545  -13.5745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6390  -13.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3467  -14.8002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6390  -12.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9313  -13.9831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2236  -13.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5159  -13.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2236  -12.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3467  -12.3487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3467  -11.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6390  -11.1229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6390  -10.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9313   -9.8971    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3467   -9.8971    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7622  -13.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4699  -13.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1776  -13.9831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4699  -12.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7622  -14.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4699  -15.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4654  -16.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1723  -16.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8809  -16.0270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8783  -15.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1709  -14.8007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8089  -13.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1017  -13.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1012  -14.7971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8139  -15.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5182  -14.7953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3941  -13.5701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3945  -12.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3940  -15.2067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6858  -14.7990    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
 28 32  1  0
 32 33  1  0
 29 34  1  0
 34 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2208336

   N-[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]-3,4-dimethoxybenzamide

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: 484.56

Molecular Weight (Monoisotopic): 484.2434

AlogP: 0.28

#Rotatable Bonds: 13

Polar Surface Area: 181.65

Molecular Species: BASE

HBA: 6

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.08

CX Basic pKa: 11.70

CX LogP: -0.17

CX LogD: -2.23

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.13

Np Likeness Score: -0.17

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