(R)-4-(4-(3-(5-oxo-5,6-dihydro-1,6-naphthyridin-7-yl)cyclopent-2-en-1-yl)piperazin-1-yl)benzonitrile

ID: ALA4776820

PubChem CID: 126602424

Max Phase: Preclinical

Molecular Formula: C24H23N5O

Molecular Weight: 397.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(N2CCN([C@H]3C=C(c4cc5ncccc5c(=O)[nH]4)CC3)CC2)cc1

Standard InChI:  InChI=1S/C24H23N5O/c25-16-17-3-6-19(7-4-17)28-10-12-29(13-11-28)20-8-5-18(14-20)22-15-23-21(24(30)27-22)2-1-9-26-23/h1-4,6-7,9,14-15,20H,5,8,10-13H2,(H,27,30)/t20-/m1/s1

Standard InChI Key:  IBBZXRLLZKUNIM-HXUWFJFHSA-N

Molfile:  

 
     RDKit          2D

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   27.7420  -32.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4579  -32.7094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.4560  -31.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1725  -31.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1733  -32.2942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8897  -32.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6059  -32.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6011  -31.4598    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   31.3231  -32.6984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8798  -30.2245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.4193  -33.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2275  -33.6865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6355  -32.9691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0794  -32.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4519  -32.8781    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.9350  -33.5420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7481  -33.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0815  -32.7020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5953  -32.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7759  -32.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8983  -32.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3790  -33.2780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1951  -33.1905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5279  -32.4385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0387  -31.7733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2244  -31.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3446  -32.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1570  -32.2568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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 20 23  1  0
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 24 25  1  0
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 26 29  1  0
 29 30  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4776820

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 397.48

Molecular Weight (Monoisotopic): 397.1903

AlogP: 3.16

#Rotatable Bonds: 3

Polar Surface Area: 76.02

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.51

CX Basic pKa: 7.82

CX LogP: 2.60

CX LogD: 2.04

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.73

Np Likeness Score: -0.99

References

1. Karche NP,Bhonde M,Sinha N,Jana G,Kukreja G,Kurhade SP,Jagdale AR,Tilekar AR,Hajare AK,Jadhav GR,Gupta NR,Limaye R,Khedkar N,Thube BR,Shaikh JS,Rao Irlapati N,Phukan S,Gole G,Bommakanti A,Khanwalkar H,Pawar Y,Kale R,Kumar R,Gupta R,Praveen Kumar VR,Wahid S,Francis A,Bhat T,Kamble N,Patil V,Nigade PB,Modi D,Pawar S,Naidu S,Volam H,Pagdala V,Mallurwar S,Goyal H,Bora P,Ahirrao P,Singh M,Kamalakannan P,Naik KR,Kumar P,Powar RG,Shankar RB,Bernstein PR,Gundu J,Nemmani K,Narasimham L,George KS,Sharma S,Bakhle D,Kamboj RK,Palle VP.  (2020)  Discovery of isoquinolinone and naphthyridinone-based inhibitors of poly(ADP-ribose) polymerase-1 (PARP1) as anticancer agents: Structure activity relationship and preclinical characterization.,  28  (24): [PMID:33120078] [10.1016/j.bmc.2020.115819]

Source

Source(1):

• Scientific Literature