US9320722, 18

ID: ALA4108422

PubChem CID: 4800055

Max Phase: Preclinical

Molecular Formula: C18H21N3O4S

Molecular Weight: 375.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)NS(=O)(=O)c1ccc(Nc2ccc3c(c2)CCC3)c([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C18H21N3O4S/c1-12(2)20-26(24,25)16-8-9-17(18(11-16)21(22)23)19-15-7-6-13-4-3-5-14(13)10-15/h6-12,19-20H,3-5H2,1-2H3

Standard InChI Key:  LNAQZCYWSFRFIF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    0.2316  -10.3494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2725   -9.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3099  -10.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2777   -8.2515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5796   -7.5048    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5760   -8.7048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6169   -8.1081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5847   -6.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2883   -5.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935   -3.7495    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 N   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
   -2.7248    1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6065    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7248   -1.2135    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
    3.8915   -3.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8864   -5.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1954   -3.0153    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2317   -3.6204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2017   -1.8153    0.0000 O   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  0
  5  6  2  0
  5  7  2  0
  5  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 16  1  0
 20 21  2  0
 21 13  1  0
 11 22  1  0
 22 23  2  0
 23  8  1  0
 22 24  1  0
 24 25  2  0
 24 26  1  0
M  CHG  2  24   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4108422

   CB29 (derivative 18)

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: 375.45

Molecular Weight (Monoisotopic): 375.1253

AlogP: 3.51

#Rotatable Bonds: 6

Polar Surface Area: 101.34

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.05

CX Basic pKa: ┄

CX LogP: 5.26

CX LogD: 5.26

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.59

Np Likeness Score: -1.87

References

1.  (2016)  Regulators of aldehyde dehydrogenase ALDH3A1 and related therapeutic methods, 

Source

Source(1):

• BindingDB Database