rac-(3S,3'S,4'S,5'S)-5'-benzyl-6-chloro-3'-(3-chlorophenyl)-4'-nitro-1,2-dihydrospiro[indole-3,2'-pyrrolidine]-2-one

ID: ALA4776003

PubChem CID: 162643498

Max Phase: Preclinical

Molecular Formula: C24H19Cl2N3O3

Molecular Weight: 468.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1Nc2cc(Cl)ccc2[C@]12N[C@@H](Cc1ccccc1)[C@@H]([N+](=O)[O-])[C@@H]2c1cccc(Cl)c1

Standard InChI:  InChI=1S/C24H19Cl2N3O3/c25-16-8-4-7-15(12-16)21-22(29(31)32)20(11-14-5-2-1-3-6-14)28-24(21)18-10-9-17(26)13-19(18)27-23(24)30/h1-10,12-13,20-22,28H,11H2,(H,27,30)/t20-,21-,22+,24+/m0/s1

Standard InChI Key:  BFAARWMTSAIQDF-ZPFZUWPUSA-N

Molfile:  

 
     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   22.2256  -17.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9959  -17.4490    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9752  -16.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1920  -16.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7288  -17.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0321  -17.9823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0310  -18.8018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7390  -19.2108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7373  -17.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4459  -17.9787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4507  -18.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2307  -19.0458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.7081  -18.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5252  -18.3769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3230  -19.2099    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.0158  -16.6616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0180  -15.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3059  -15.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5926  -15.8388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5958  -16.6660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3085  -17.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3057  -14.6096    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.9204  -15.6254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1170  -15.4759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4516  -15.0044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6240  -16.1354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3787  -16.4487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4827  -17.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2366  -17.5720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8863  -17.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7772  -16.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0232  -15.9511    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  5  1  0
  5  1  1  0
  6  7  2  0
  7  8  1  0
  8 11  2  0
 10  9  2  0
  9  6  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  1  1  0
  1 10  1  6
 13 14  2  0
  7 15  1  0
  5 16  1  1
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 18 22  1  0
 23 24  2  0
 23 25  1  0
  4 23  1  6
  3 26  1  6
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
M  CHG  2  23   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4776003

   ---

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: 468.34

Molecular Weight (Monoisotopic): 467.0803

AlogP: 4.78

#Rotatable Bonds: 4

Polar Surface Area: 84.27

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.28

CX Basic pKa: 6.77

CX LogP: 5.22

CX LogD: 5.28

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.43

Np Likeness Score: -0.33

References

1. Gollner A,Rudolph D,Arnhof H,Bauer M,Blake SM,Boehmelt G,Cockroft XL,Dahmann G,Ettmayer P,Gerstberger T,Karolyi-Oezguer J,Kessler D,Kofink C,Ramharter J,Rinnenthal J,Savchenko A,Schnitzer R,Weinstabl H,Weyer-Czernilofsky U,Wunberg T,McConnell DB.  (2016)  Discovery of Novel Spiro[3H-indole-3,2'-pyrrolidin]-2(1H)-one Compounds as Chemically Stable and Orally Active Inhibitors of the MDM2-p53 Interaction.,  59  (22): [PMID:27775892] [10.1021/acs.jmedchem.6b00900]

Source

Source(1):

• Scientific Literature