(4S)-4-((2S,3S)-2-amino-3-methylpentanamido)-5-oxo-5-(1-oxo-1-((S)-1-oxo-3-phenylpropan-2-ylamino)hexan-2-ylamino)pentanoic acid

ID: ALA4080150

PubChem CID: 137647098

Max Phase: Preclinical

Molecular Formula: C26H40N4O6

Molecular Weight: 504.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCC(NC(=O)[C@H](CCC(=O)O)NC(=O)[C@@H](N)[C@@H](C)CC)C(=O)N[C@H](C=O)Cc1ccccc1

Standard InChI:  InChI=1S/C26H40N4O6/c1-4-6-12-20(24(34)28-19(16-31)15-18-10-8-7-9-11-18)29-25(35)21(13-14-22(32)33)30-26(36)23(27)17(3)5-2/h7-11,16-17,19-21,23H,4-6,12-15,27H2,1-3H3,(H,28,34)(H,29,35)(H,30,36)(H,32,33)/t17-,19-,20?,21-,23-/m0/s1

Standard InChI Key:  OKKHZZUYGYWEDI-JQYJAXMZSA-N

Molfile:  

     RDKit          2D

 36 36  0  0  0  0  0  0  0  0999 V2000
    3.7533  -12.3040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4672  -11.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1812  -13.1269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1812  -12.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4672  -11.0656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1812  -10.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7533  -10.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7533   -9.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9011  -11.8896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6197  -12.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3337  -11.0680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3337  -11.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6197  -13.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3337  -13.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3337  -14.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0476  -14.7833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6245  -14.7851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0521  -12.3080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7700  -11.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4840  -13.1285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4840  -12.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2030  -11.8896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9210  -12.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6350  -11.0691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6350  -11.8919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9210  -13.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6350  -14.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6350  -13.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3479  -13.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0652  -13.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0652  -14.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3479  -14.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7700  -11.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4826  -10.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4826   -9.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1952   -9.4216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  9  1  0
 12 18  1  0
 21 22  1  0
  2  1  1  1
  2  4  1  0
  4  3  2  0
  2  5  1  0
  5  6  1  6
  5  7  1  0
  7  8  1  0
  9 10  1  0
 10 12  1  0
 12 11  2  0
 10 13  1  6
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 18 19  1  0
 19 21  1  0
 21 20  2  0
 22 23  1  0
 23 25  1  0
 25 24  2  0
 23 26  1  6
 26 28  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
 19 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4080150

   ---

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: 504.63

Molecular Weight (Monoisotopic): 504.2948

AlogP: 1.31

#Rotatable Bonds: 17

Polar Surface Area: 167.69

Molecular Species: ACID

HBA: 6

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.22

CX Basic pKa: 8.21

CX LogP: -0.56

CX LogD: -0.62

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.20

Np Likeness Score: 0.50

References

1. Swedberg JE, Li CY, de Veer SJ, Wang CK, Craik DJ..  (2017)  Design of Potent and Selective Cathepsin G Inhibitors Based on the Sunflower Trypsin Inhibitor-1 Scaffold.,  60  (2): [PMID:28045523] [10.1021/acs.jmedchem.6b01509]

Source

Source(1):

• Scientific Literature