(S)-N-(3-amino-2-(3-methylbenzamido)-3-oxopropyl)-1,4-dioxo-1,2,3,4-tetrahydrophthalazine-6-carboxamide

ID: ALA5190289

PubChem CID: 168284044

Max Phase: Preclinical

Molecular Formula: C20H19N5O5

Molecular Weight: 409.40

Names and Identifiers

Canonical SMILES:  Cc1cccc(C(=O)N[C@@H](CNC(=O)c2ccc3c(=O)[nH][nH]c(=O)c3c2)C(N)=O)c1

Standard InChI:  InChI=1S/C20H19N5O5/c1-10-3-2-4-11(7-10)18(28)23-15(16(21)26)9-22-17(27)12-5-6-13-14(8-12)20(30)25-24-19(13)29/h2-8,15H,9H2,1H3,(H2,21,26)(H,22,27)(H,23,28)(H,24,29)(H,25,30)/t15-/m0/s1

Standard InChI Key:  PUFUAFGCANGLMI-HNNXBMFYSA-N

Molfile:  

 
     RDKit          2D

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    1.7881    1.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5026    1.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2145    1.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2145    0.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5045   -0.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7881    0.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292    1.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6438    1.0323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6438    0.2072    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -0.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292    2.2700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -1.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0734   -0.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0734   -1.0342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3588    0.2034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3557   -0.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0704    0.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7850   -0.2090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0704    1.0287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7850    1.4413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3557    1.4413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4996    0.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2143   -0.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4996    1.0287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2145   -1.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9274   -1.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6422   -1.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6438   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9320    0.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9274   -2.2700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  3  7  1  0
  8  7  1  0
  9  8  1  0
 10  9  1  0
  4 10  1  0
  7 11  2  0
 10 12  2  0
  6 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 17 16  1  6
 17 18  1  0
 17 19  1  0
 19 20  2  0
 19 21  1  0
 18 22  1  0
 22 23  1  0
 22 24  2  0
 25 23  2  0
 26 25  1  0
 27 26  2  0
 28 27  1  0
 29 28  2  0
 23 29  1  0
 26 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5190289

   ---

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: 409.40

Molecular Weight (Monoisotopic): 409.1386

AlogP: -0.46

#Rotatable Bonds: 6

Polar Surface Area: 167.01

Molecular Species: NEUTRAL

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.79

CX Basic pKa: ┄

CX LogP: -0.54

CX LogD: -0.67

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.37

Np Likeness Score: -0.81

References

1. Nizi MG, Maksimainen MM, Lehtiö L, Tabarrini O..  (2022)  Medicinal Chemistry Perspective on Targeting Mono-ADP-Ribosylating PARPs with Small Molecules.,  65  (11.0): [PMID:35608571] [10.1021/acs.jmedchem.2c00281]

Source

Source(1):

• Scientific Literature