N-[4-[(phenylsulfonamido)carbonyl]benzoyl]-L-phenylalanyl-L-alanyl[(2,4,6-Trimethylbenzoyl)oxy)methyl ketone

ID: ALA291453

PubChem CID: 44297453

Max Phase: Preclinical

Molecular Formula: C37H37N3O8S

Molecular Weight: 683.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C)c(C(=O)OCC(=O)[C@@H](C)NC(=O)[C@H](Cc2ccccc2)NC(=O)c2ccc(C(=O)NS(=O)(=O)c3ccccc3)cc2)c(C)c1

Standard InChI:  InChI=1S/C37H37N3O8S/c1-23-19-24(2)33(25(3)20-23)37(45)48-22-32(41)26(4)38-36(44)31(21-27-11-7-5-8-12-27)39-34(42)28-15-17-29(18-16-28)35(43)40-49(46,47)30-13-9-6-10-14-30/h5-20,26,31H,21-22H2,1-4H3,(H,38,44)(H,39,42)(H,40,43)/t26-,31+/m1/s1

Standard InChI Key:  NNBPHYKERIZVOW-NEEKEDPPSA-N

Molfile:  

     RDKit          2D

 49 52  0  0  1  0  0  0  0  0999 V2000
   -6.5042   -8.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2083   -7.4875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2083   -5.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8917   -3.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0083   -2.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9917   -3.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2917   -3.7458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2917   -3.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9958   -1.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1917   -3.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5917   -3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6917   -3.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7917   -3.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5458   -7.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5042   -7.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5042   -9.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917   -3.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9083   -5.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3083   -3.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3917   -3.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2958   -0.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5917   -3.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2458   -5.3833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8875   -4.9583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0042   -1.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0917   -3.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5958   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6875   -4.9833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5917   -1.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7958   -1.8208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3125   -5.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9083   -3.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6083   -2.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6125   -5.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8958   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2875   -4.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9583   -0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4875   -4.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2125  -10.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8042  -10.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6333   -0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1917   -1.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2125  -11.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8042  -11.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2000    1.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917   -0.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5083  -12.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5000    0.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4 11  1  0
  5 19  1  0
  6 12  1  0
  7  5  1  0
  8  6  2  0
  9  6  1  0
 10  4  1  0
 11  7  1  0
 12 20  1  0
 13 17  1  0
 14  1  2  0
 15  1  2  0
 16  1  1  0
 17 10  1  0
 18  3  1  0
 19 31  1  0
 20 26  1  0
 21  9  2  0
 22  8  1  0
 23  3  2  0
 24  4  2  0
 25  5  2  0
 26 13  1  0
 11 27  1  1
 28 12  2  0
 29 21  1  0
 30 13  2  0
 31 34  2  0
 32 18  2  0
 33 32  1  0
 34 18  1  0
 35 27  1  0
 36  8  1  0
 37  9  1  0
 17 38  1  1
 39 16  2  0
 40 16  1  0
 41 29  1  0
 42 35  1  0
 43 35  2  0
 44 39  1  0
 45 40  2  0
 46 43  1  0
 47 42  2  0
 48 45  1  0
 49 47  1  0
 48 44  2  0
 33 19  2  0
 49 46  2  0
 29 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA291453

   [(3R)-3-[[(2S)-2-[[4-(benzenesulfonylcarbamoyl)benzoyl]amino]-3-phenylpropanoyl]amino]-2-oxobutyl] 2,4,6-trimethylbenzoate

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: 683.78

Molecular Weight (Monoisotopic): 683.2301

AlogP: 4.00

#Rotatable Bonds: 13

Polar Surface Area: 164.81

Molecular Species: ACID

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.28

CX Basic pKa: ┄

CX LogP: 6.21

CX LogD: 5.27

Aromatic Rings: 4

Heavy Atoms: 49

QED Weighted: 0.18

Np Likeness Score: -0.54

References

1. Wagner BM, Smith RA, Coles PJ, Copp LJ, Ernest MJ, Krantz A..  (1994)  In vivo inhibition of cathepsin B by peptidyl (acyloxy)methyl ketones.,  37  (12): [PMID:8021922] [10.1021/jm00038a012]

Source

Source(1):

• Scientific Literature