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

ID: ALA2208331

PubChem CID: 10143123

Max Phase: Preclinical

Molecular Formula: C22H26Cl2N6O3

Molecular Weight: 493.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)NCCC[C@H](NC(=O)c1ccc(Cl)c(Cl)c1)C(=O)N[C@@H](Cc1ccccc1)C(N)=O

Standard InChI:  InChI=1S/C22H26Cl2N6O3/c23-15-9-8-14(12-16(15)24)20(32)29-17(7-4-10-28-22(26)27)21(33)30-18(19(25)31)11-13-5-2-1-3-6-13/h1-3,5-6,8-9,12,17-18H,4,7,10-11H2,(H2,25,31)(H,29,32)(H,30,33)(H4,26,27,28)/t17-,18-/m0/s1

Standard InChI Key:  JIKAORMZYVXNRV-ROUUACIJSA-N

Molfile:  

     RDKit          2D

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    6.0877  -30.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7954  -29.6789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3800  -29.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0877  -30.9047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3800  -28.8617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6722  -30.0875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9645  -29.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2568  -30.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9645  -28.8617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0877  -28.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0877  -27.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3800  -27.2273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3800  -26.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6722  -26.0015    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0877  -26.0015    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5031  -30.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2108  -29.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9185  -30.0875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2108  -28.8617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5031  -30.9047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2108  -31.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2063  -32.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9132  -32.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6219  -32.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6192  -31.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9118  -30.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5498  -29.6756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8426  -30.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8421  -30.9016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5548  -31.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2591  -30.8997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1351  -29.6746    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1350  -31.3111    0.0000 Cl  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
 29 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2208331

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

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: 493.40

Molecular Weight (Monoisotopic): 492.1443

AlogP: 1.57

#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: 11.88

CX Basic pKa: 12.18

CX LogP: 1.32

CX LogD: -0.70

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.16

Np Likeness Score: -0.50

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