US8691753, 54

ID: ALA3675556

PubChem CID: 50992417

Max Phase: Preclinical

Molecular Formula: C25H29N3O8

Molecular Weight: 499.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)CCc1ccc(-c2cccc(O)c2)cc1

Standard InChI:  InChI=1S/C25H29N3O8/c26-24(35)19(9-12-22(31)32)28-25(36)20(10-13-23(33)34)27-21(30)11-6-15-4-7-16(8-5-15)17-2-1-3-18(29)14-17/h1-5,7-8,14,19-20,29H,6,9-13H2,(H2,26,35)(H,27,30)(H,28,36)(H,31,32)(H,33,34)/t19-,20-/m0/s1

Standard InChI Key:  UIEDXQBYCVBGGE-PMACEKPBSA-N

Molfile:  

     RDKit          2D

 36 37  0  0  1  0  0  0  0  0999 V2000
    5.1766  -11.7111    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1807  -10.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1434   -9.9078    0.0000 O   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
    6.4855   -8.2648    0.0000 N   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
    5.1894   -6.0109    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
    6.4894   -3.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7889   -3.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7893   -1.8084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8281   -3.6084    0.0000 O   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
   -2.6012    3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9015    3.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1993    2.9963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1969    1.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2352    0.8946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8967    0.7484    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  1  0
  7  8  2  0
  7  9  1  0
  4 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  1
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 13 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 27 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  1  0
 34 36  2  0
 36 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3675556

   (4S)-5-amino-4-[[(2S)-4-carboxy-2-[3-[4-(3-hydroxyphenyl)phenyl]propanoylamino]butanoyl]amino]-5-oxopentanoic 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: 499.52

Molecular Weight (Monoisotopic): 499.1955

AlogP: 1.18

#Rotatable Bonds: 14

Polar Surface Area: 196.12

Molecular Species: ACID

HBA: 6

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.83

CX Basic pKa: ┄

CX LogP: 0.81

CX LogD: -5.34

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.22

Np Likeness Score: 0.07

References

1.  (2014)  Pseudodipeptides as MMP inhibitors, 

Source

Source(1):

• BindingDB Database