US8691753, 101

ID: ALA3675599

PubChem CID: 69922083

Max Phase: Preclinical

Molecular Formula: C28H29N3O7S

Molecular Weight: 551.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)CCc1ccc(-c2cc(-c3ccccc3)cs2)cc1

Standard InChI:  InChI=1S/C28H29N3O7S/c29-27(37)22(15-26(35)36)31-28(38)21(11-13-25(33)34)30-24(32)12-8-17-6-9-19(10-7-17)23-14-20(16-39-23)18-4-2-1-3-5-18/h1-7,9-10,14,16,21-22H,8,11-13,15H2,(H2,29,37)(H,30,32)(H,31,38)(H,33,34)(H,35,36)/t21-,22-/m0/s1

Standard InChI Key:  UUDTVMMARAFNKG-VXKWHMMOSA-N

Molfile:  

     RDKit          2D

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    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
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   -4.9546    1.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9492    0.8772    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8193    4.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0353    5.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7489    7.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2483    7.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3205    4.6976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  1
  5  6  1  0
  6  7  2  0
  6  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
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 12 13  1  1
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 14 15  1  0
 15 16  2  0
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 12 18  1  0
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 19 20  2  0
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 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 26 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 29  1  0
 31 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
 39 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3675599

   (4S)-5-[[(2S)-1-amino-3-carboxy-1-oxopropan-2-yl]amino]-5-oxo-4-[3-[4-(4-phenylthiophen-2-yl)phenyl]propanoylamino]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: 551.62

Molecular Weight (Monoisotopic): 551.1726

AlogP: 2.81

#Rotatable Bonds: 14

Polar Surface Area: 175.89

Molecular Species: ACID

HBA: 6

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.59

CX Basic pKa: ┄

CX LogP: 2.25

CX LogD: -4.09

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.20

Np Likeness Score: -0.21

References

1.  (2014)  Pseudodipeptides as MMP inhibitors, 

Source

Source(1):

• BindingDB Database