US8691753, 38

ID: ALA3675542

PubChem CID: 84973138

Max Phase: Preclinical

Molecular Formula: C22H27N3O5S

Molecular Weight: 445.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](NC(=O)CCc1ccc(-c2ccsc2)cc1)C(=O)N[C@@H](CCC(=O)O)C(N)=O

Standard InChI:  InChI=1S/C22H27N3O5S/c1-2-17(22(30)25-18(21(23)29)8-10-20(27)28)24-19(26)9-5-14-3-6-15(7-4-14)16-11-12-31-13-16/h3-4,6-7,11-13,17-18H,2,5,8-10H2,1H3,(H2,23,29)(H,24,26)(H,25,30)(H,27,28)/t17-,18-/m0/s1

Standard InChI Key:  AEOWLQGPNGMHBP-ROUUACIJSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  1  0  0  0  0  0999 V2000
    6.4893   -4.0601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4889   -5.2601    0.0000 C   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
    3.8912   -5.2578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9336   -3.1588    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
   -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
   -2.5987    1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7390    2.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2067    3.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9546    1.9903    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9492    0.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1873   -7.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1470   -8.1099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4855   -8.2648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4833   -9.7656    0.0000 C   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
    9.0776  -12.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0759  -13.9726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1179  -12.1744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1838  -10.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1834  -11.7165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1446   -9.9165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 15  2  0
  3 20  1  0
 20 21  2  0
 20 22  1  0
 23 22  1  1
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 23 29  1  0
 29 30  2  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3675542

   (4S)-5-amino-5-oxo-4-[[(2S)-2-[3-(4-thiophen-3-ylphenyl)propanoylamino]butanoyl]amino]pentanoic 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: 445.54

Molecular Weight (Monoisotopic): 445.1671

AlogP: 2.08

#Rotatable Bonds: 12

Polar Surface Area: 138.59

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.13

CX Basic pKa: ┄

CX LogP: 1.77

CX LogD: -1.31

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.40

Np Likeness Score: -0.61

References

1.  (2014)  Pseudodipeptides as MMP inhibitors, 

Source

Source(1):

• BindingDB Database