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

ID: ALA3691805

PubChem CID: 46176035

Max Phase: Preclinical

Molecular Formula: C23H23N3O3

Molecular Weight: 389.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC(C(=O)O)n1nc(Cc2cn(C)c3ccccc23)c2ccccc2c1=O

Standard InChI:  InChI=1S/C23H23N3O3/c1-3-8-21(23(28)29)26-22(27)18-11-5-4-10-17(18)19(24-26)13-15-14-25(2)20-12-7-6-9-16(15)20/h4-7,9-12,14,21H,3,8,13H2,1-2H3,(H,28,29)

Standard InChI Key:  ALXLWMJOACABSO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    6.2387   -0.8917    0.0000 C   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
    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 N   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 C   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
    2.6532    3.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6606    4.2353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8536    4.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9151    5.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3833    6.9611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3833    8.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9151    7.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4468    6.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4468    5.2290    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
   -2.5981    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971   -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
   -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
    0.0000   -2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6060   -2.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6472   -3.5953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5689   -3.6022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18  9  1  0
 18 13  1  0
  7 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 24 25  1  0
 25  5  1  0
 25 26  2  0
  4 27  1  0
 27 28  2  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3691805

   US8969348, 2-{4-[(1-Methyl-1H-indol-3-yl)methyl]-1-oxophthalazin-2(1H)-yl}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: 389.46

Molecular Weight (Monoisotopic): 389.1739

AlogP: 3.90

#Rotatable Bonds: 6

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: 3.60

CX Basic pKa: ┄

CX LogP: 4.23

CX LogD: 0.89

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.54

Np Likeness Score: -0.63

References

1.  (2015)  Chymase inhibitors, 

Source

Source(1):

• BindingDB Database