4-(4-Fluoro-3-(2-oxa-6-azaspiro[3.3]heptane-6-carbonyl)benzyl)-phthalazin-1(2H)-one

ID: ALA4169555

PubChem CID: 145953485

Max Phase: Preclinical

Molecular Formula: C21H18FN3O3

Molecular Weight: 379.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(c1cc(Cc2n[nH]c(=O)c3ccccc23)ccc1F)N1CC2(COC2)C1

Standard InChI:  InChI=1S/C21H18FN3O3/c22-17-6-5-13(7-16(17)20(27)25-9-21(10-25)11-28-12-21)8-18-14-3-1-2-4-15(14)19(26)24-23-18/h1-7H,8-12H2,(H,24,26)

Standard InChI Key:  XGCWPAJMWZAIBV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
    9.0029  -12.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2134  -13.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0017  -12.9916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7912  -12.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -9.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3376  -10.2337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0456  -10.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0438   -9.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7525   -9.4106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7558  -10.2312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4643  -10.6364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1739  -10.2254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1705   -9.4048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4575   -8.9951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4530   -8.1779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4665  -11.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1753  -11.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1750  -12.6758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8830  -13.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5906  -12.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5857  -11.8504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8772  -11.4475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2999  -13.0775    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.2908  -11.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0011  -11.8416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2857  -10.6202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2146  -12.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7862  -11.6253    0.0000 C   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  1  1  0
  5  6  2  0
  6  7  1  0
  7 10  2  0
  9  8  2  0
  8  5  1  0
  9 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 11 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 20 23  1  0
 21 24  1  0
 24 25  1  0
 24 26  2  0
 25 27  1  0
 27  1  1  0
  1 28  1  0
 28 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4169555

   ---

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: 379.39

Molecular Weight (Monoisotopic): 379.1332

AlogP: 2.13

#Rotatable Bonds: 3

Polar Surface Area: 75.29

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.96

CX Basic pKa: ┄

CX LogP: 1.57

CX LogD: 1.57

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.76

Np Likeness Score: -1.27

References

1. Reilly SW, Puentes LN, Wilson K, Hsieh CJ, Weng CC, Makvandi M, Mach RH..  (2018)  Examination of Diazaspiro Cores as Piperazine Bioisosteres in the Olaparib Framework Shows Reduced DNA Damage and Cytotoxicity.,  61  (12): [PMID:29856625] [10.1021/acs.jmedchem.8b00576]

Source

Source(1):

• Scientific Literature