8-(4-(Azetidin-1-ylmethyl)phenyl)-9-(4-fluorophenyl)-2,7,8,9-tetrahydro-3H-pyrido[4,3,2-de]phthalazin-3-one

ID: ALA3763674

PubChem CID: 136130843

Max Phase: Preclinical

Molecular Formula: C26H23FN4O

Molecular Weight: 426.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]nc2c3c(cccc13)NC(c1ccc(CN3CCC3)cc1)C2c1ccc(F)cc1

Standard InChI:  InChI=1S/C26H23FN4O/c27-19-11-9-17(10-12-19)22-24(18-7-5-16(6-8-18)15-31-13-2-14-31)28-21-4-1-3-20-23(21)25(22)29-30-26(20)32/h1,3-12,22,24,28H,2,13-15H2,(H,30,32)

Standard InChI Key:  UMTZOWPWZLHANK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 37  0  0  0  0  0  0  0  0999 V2000
   -2.5914    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5914   -1.4965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2957   -2.2629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2957    0.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2957    2.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2957    2.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2957    0.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2957   -2.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5914   -1.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5914    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6307    0.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2957   -3.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0039   -4.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0175   -6.0251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3233   -6.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6155   -6.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6019   -4.5016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3342   -7.9633    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.8951   -2.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1889   -1.4803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4935   -2.2206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5046   -3.7205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2112   -4.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9066   -3.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8084   -4.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8174   -5.9647    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8821   -6.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8256   -8.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7608   -6.9779    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  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  1 10  1  0
  5 10  2  0
 11 12  1  0
 12 13  1  0
  4 11  1  0
  6 13  1  0
  1 14  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 15 20  2  0
 18 21  1  0
 11 15  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 22 27  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 29 32  1  0
 28 29  1  0
 25 28  1  0
 12 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3763674

   ---

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: 426.50

Molecular Weight (Monoisotopic): 426.1856

AlogP: 4.57

#Rotatable Bonds: 4

Polar Surface Area: 61.02

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.06

CX Basic pKa: 8.35

CX LogP: 3.56

CX LogD: 2.68

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.50

Np Likeness Score: -1.09

References

1. Wang B, Chu D, Feng Y, Shen Y, Aoyagi-Scharber M, Post LE..  (2016)  Discovery and Characterization of (8S,9R)-5-Fluoro-8-(4-fluorophenyl)-9-(1-methyl-1H-1,2,4-triazol-5-yl)-2,7,8,9-tetrahydro-3H-pyrido[4,3,2-de]phthalazin-3-one (BMN 673, Talazoparib), a Novel, Highly Potent, and Orally Efficacious Poly(ADP-ribose) Polymerase-1/2 Inhibitor, as an Anticancer Agent.,  59  (1): [PMID:26652717] [10.1021/acs.jmedchem.5b01498]

Source

Source(1):

• Scientific Literature