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

ID: ALA2208334

PubChem CID: 71463276

Max Phase: Preclinical

Molecular Formula: C23H30N6O4

Molecular Weight: 454.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc2ccccc2)C(N)=O)c1

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

Standard InChI Key:  ZTAYITNDDNUUNE-OALUTQOASA-N

Molfile:  

     RDKit          2D

 33 34  0  0  0  0  0  0  0  0999 V2000
   17.1032   -5.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8109   -5.3695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3955   -5.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1032   -6.5953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3955   -4.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6878   -5.7781    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9801   -5.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2724   -5.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9801   -4.5523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1032   -4.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1032   -3.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3955   -2.9180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3955   -2.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6878   -1.6922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1032   -1.6922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5187   -5.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2264   -5.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9341   -5.7781    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2264   -4.5523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5187   -6.5953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2264   -7.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2219   -7.8222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9288   -8.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6374   -7.8220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6348   -7.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9274   -6.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5654   -5.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8581   -5.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8577   -6.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5704   -7.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2747   -6.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1506   -5.3652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4427   -5.7734    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
M  END

Alternative Forms

1. Parent:

   

   ALA2208334

   Bz(3-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: 11.76

CX LogP: 0.01

CX LogD: -2.07

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.15

Np Likeness Score: -0.31

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