US9115102, Ex2

ID: ALA3704903

PubChem CID: 51029815

Max Phase: Preclinical

Molecular Formula: C19H26N4O6S

Molecular Weight: 438.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC#CCOc1ccc(C(=O)NC[C@@H](C(=O)NO)N2CCN(S(C)(=O)=O)CC2)cc1

Standard InChI:  InChI=1S/C19H26N4O6S/c1-3-4-13-29-16-7-5-15(6-8-16)18(24)20-14-17(19(25)21-26)22-9-11-23(12-10-22)30(2,27)28/h5-8,17,26H,9-14H2,1-2H3,(H,20,24)(H,21,25)/t17-/m0/s1

Standard InChI Key:  GHBQSNPRMVUGFE-KRWDZBQOSA-N

Molfile:  

     RDKit          2D

 30 31  0  0  1  0  0  0  0  0999 V2000
    6.2295   -5.1122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1915   -4.5101    0.0000 C   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
    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 O   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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   -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
   -2.6003    1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6024    2.6977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4990    0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8003    1.4887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0994    0.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3984    1.4886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3985    2.9886    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0995    3.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8004    2.9887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6983    3.7390    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7379    3.1397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6979    4.9390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7372    4.3395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4995   -0.7599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4602   -1.3599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7990   -1.5107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7994   -2.7107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  3  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  9 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 16 15  1  1
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 17  1  0
 20 23  1  0
 23 24  2  0
 23 25  2  0
 23 26  1  0
 16 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3704903

   4-but-2-ynoxy-N-[(2S)-3-(hydroxyamino)-2-(4-methylsulfonylpiperazin-1-yl)-3-oxopropyl]benzamide

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: 438.51

Molecular Weight (Monoisotopic): 438.1573

AlogP: -0.73

#Rotatable Bonds: 8

Polar Surface Area: 128.28

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.71

CX Basic pKa: 3.67

CX LogP: -0.58

CX LogD: -0.60

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.28

Np Likeness Score: -1.15

References

1.  (2015)  N-[2-hydroxycarbamoyl-2-(piperazinyl) ethyl] benzamide compounds, their preparation and their use as TACE inhibitors, 

Source

Source(1):

• BindingDB Database