US8969348, 3-{4-[(1,4-Dimethyl-1H-indol-3-yl)methyl]-1-oxophthalazin-2(1H)-yl}propanoic acid

ID: ALA3691799

PubChem CID: 46175869

Max Phase: Preclinical

Molecular Formula: C22H21N3O3

Molecular Weight: 375.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc2c1c(Cc1nn(CCC(=O)O)c(=O)c3ccccc13)cn2C

Standard InChI:  InChI=1S/C22H21N3O3/c1-14-6-5-9-19-21(14)15(13-24(19)2)12-18-16-7-3-4-8-17(16)22(28)25(23-18)11-10-20(26)27/h3-9,13H,10-12H2,1-2H3,(H,26,27)

Standard InChI Key:  SRWLFOUYCJTYKD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    4.9201   -3.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7201   -2.7865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1884   -3.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1884   -1.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7201   -0.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2519   -0.2434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2519   -1.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990   -0.7455    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
    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 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039    3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3070    5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3470    5.8487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2688    5.8520    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
   -2.3383    1.3500    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
   -2.5981   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981   -3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -3.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.0000    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
    4.0320    0.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4982    1.0526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9827    2.1504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 12 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 10  1  0
 25 20  1  0
  8 26  2  0
 26 27  1  0
 27  6  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3691799

   US8969348, 3-{4-[(1,4-Dimethyl-1H-indol-3-yl)methyl]-1-oxophthalazin-2(1H)-yl}propanoic 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: 375.43

Molecular Weight (Monoisotopic): 375.1583

AlogP: 3.26

#Rotatable Bonds: 5

Polar Surface Area: 77.12

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.99

CX Basic pKa: ┄

CX LogP: 3.44

CX LogD: 0.28

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.58

Np Likeness Score: -0.98

References

1.  (2015)  Chymase inhibitors, 

Source

Source(1):

• BindingDB Database