(R)-N-(2-(2-((4-(4-chlorobenzyl)-1-oxophthalazin-2(1H)-yl)methyl)pyrrolidin-1-yl)ethyl)-4-methoxybutanamide Hydrochloride

ID: ALA5286389

Max Phase: Preclinical

Molecular Formula: C27H34Cl2N4O3

Molecular Weight: 497.04

Names and Identifiers

Canonical SMILES:  COCCCC(=O)NCCN1CCC[C@@H]1Cn1nc(Cc2ccc(Cl)cc2)c2ccccc2c1=O.Cl

Standard InChI:  InChI=1S/C27H33ClN4O3.ClH/c1-35-17-5-9-26(33)29-14-16-31-15-4-6-22(31)19-32-27(34)24-8-3-2-7-23(24)25(30-32)18-20-10-12-21(28)13-11-20;/h2-3,7-8,10-13,22H,4-6,9,14-19H2,1H3,(H,29,33);1H/t22-;/m1./s1

Standard InChI Key:  AHCZFQKDSCADKT-VZYDHVRKSA-N

Molfile:  

     RDKit          2D

 36 38  0  0  0  0  0  0  0  0999 V2000
    2.2759   -1.4060    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.5587   -3.4316    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.8442   -3.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8442   -2.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1341   -1.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4166   -2.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4166   -3.0211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1295   -3.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7022   -1.7836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7022   -0.9586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9878   -0.5462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9878    0.2787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2733    0.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5588    0.2787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4727   -0.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3338   -0.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7460    0.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1942    0.6140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4078    1.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2044    1.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4181    2.4213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2149    2.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7982    2.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5952    2.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1785    1.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9753    1.8950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5587    1.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4284    3.4316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7022    0.6912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7022    1.5160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4167    0.2787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4167   -0.5462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1265   -0.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8427   -0.5499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8427    0.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1283    0.6905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  3  1  0
  5  4  2  0
  6  5  1  0
  7  6  2  0
  8  7  1  0
  3  8  2  0
  9  6  1  0
 10  9  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 14 13  1  6
 15 14  1  0
 16 15  1  0
 17 16  1  0
 18 17  1  0
 18 14  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 22 28  2  0
 12 29  1  0
 29 30  2  0
 31 29  1  0
 32 31  2  0
 32 10  1  0
 33 32  1  0
 34 33  2  0
 35 34  1  0
 36 35  2  0
 31 36  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 497.04

Molecular Weight (Monoisotopic): 496.2241

AlogP: 3.65

#Rotatable Bonds: 11

Polar Surface Area: 76.46

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.29

CX LogP: 3.35

CX LogD: 3.11

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.41

Np Likeness Score: -1.32

References

1. Procopiou PA, Ford AJ, Gore PM, Looker BE, Hodgson ST, Holmes DS, Vile S, Clark KL, Saunders KA, Slack RJ, Rowedder JE, Watts CJ..  (2017)  Design of Phthalazinone Amide Histamine H₁ Receptor Antagonists for Use in Rhinitis.,  8  (5): [PMID:28523114] [10.1021/acsmedchemlett.7b00112]

Source

Source(1):

• Scientific Literature