US9045524, 55

ID: ALA3673263

PubChem CID: 44520165

Max Phase: Preclinical

Molecular Formula: C35H41N5O11S

Molecular Weight: 739.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)[C@H](NC(=O)[C@H](Cc1ccc2ccccc2n1)NC(=O)[C@H](CC(=O)O)NC(=O)OCc1ccccc1)C(=O)N[C@H](/C=C/S(C)(=O)=O)CC(=O)O

Standard InChI:  InChI=1S/C35H41N5O11S/c1-21(2)31(34(47)37-25(18-29(41)42)15-16-52(3,49)50)40-33(46)27(17-24-14-13-23-11-7-8-12-26(23)36-24)38-32(45)28(19-30(43)44)39-35(48)51-20-22-9-5-4-6-10-22/h4-16,21,25,27-28,31H,17-20H2,1-3H3,(H,37,47)(H,38,45)(H,39,48)(H,40,46)(H,41,42)(H,43,44)/b16-15+/t25-,27+,28+,31+/m1/s1

Standard InChI Key:  XDTNISVZIRJASF-WGPOSJAPSA-N

Molfile:  

     RDKit          2D

 52 54  0  0  1  0  0  0  0  0999 V2000
   -1.3009   -4.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3026   -5.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3429   -5.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0044   -6.0064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2951   -5.2556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2956   -3.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2564   -3.1547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8509   -5.8560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4920   -5.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7894   -6.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8309   -5.4239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7852   -7.2199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1873   -7.5117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4855   -8.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5257   -7.6666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4833   -9.7656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7815  -10.5187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7794  -12.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0758  -12.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0706  -14.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7690  -15.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4726  -14.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4778  -12.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0049   -7.5072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0344   -8.1072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3044   -8.2580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3048   -9.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0066  -10.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0088  -12.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0292  -12.6149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0490  -12.6110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6044  -10.5097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6048  -12.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9043  -12.7613    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9047  -13.9613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9436  -12.1613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9437  -13.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  6
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  6
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 13  1  0
 18 19  2  0
 19 10  1  0
  8 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  6
 24 25  1  0
 25 26  2  0
 25 27  1  0
 23 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 33  1  0
  4 39  1  0
 39 40  2  0
 39 41  1  0
 42 41  1  1
 42 43  1  0
 43 44  1  0
 44 45  2  0
 44 46  1  0
 42 47  1  0
 47 48  2  0
 48 49  1  0
 49 50  2  0
 49 51  2  0
 49 52  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3673263

   (E,3S)-3-[[(2S)-2-[[(2S)-2-[[(2S)-3-carboxy-2-(phenylmethoxycarbonylamino)propanoyl]amino]-3-quinolin-2-ylpropanoyl]amino]-3-methylbutanoyl]amino]-5-methylsulfonylpent-4-enoic acid

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: 739.80

Molecular Weight (Monoisotopic): 739.2523

AlogP: 1.69

#Rotatable Bonds: 18

Polar Surface Area: 247.26

Molecular Species: ACID

HBA: 10

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.59

CX Basic pKa: 4.38

CX LogP: -0.11

CX LogD: -5.58

Aromatic Rings: 3

Heavy Atoms: 52

QED Weighted: 0.11

Np Likeness Score: 0.03

References

1.  (2015)  Selective caspase inhibitors and uses thereof, 

Source

Source(1):

• BindingDB Database