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

ID: ALA4789769

PubChem CID: 162669350

Max Phase: Preclinical

Molecular Formula: C21H17Cl2N5O3

Molecular Weight: 458.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1Nc2cc(Cl)ccc2[C@]12N[C@@H](Cc1c[nH]cn1)[C@@H]([N+](=O)[O-])[C@@H]2c1cccc(Cl)c1

Standard InChI:  InChI=1S/C21H17Cl2N5O3/c22-12-3-1-2-11(6-12)18-19(28(30)31)17(8-14-9-24-10-25-14)27-21(18)15-5-4-13(23)7-16(15)26-20(21)29/h1-7,9-10,17-19,27H,8H2,(H,24,25)(H,26,29)/t17-,18-,19+,21+/m0/s1

Standard InChI Key:  OHAOXDKVEPBNCW-CTAFRAEOSA-N

Molfile:  

 
     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   40.3028   -4.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0732   -3.8870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.0525   -3.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2693   -2.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8061   -3.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1094   -4.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1083   -5.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8163   -5.6487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8145   -4.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5231   -4.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5279   -5.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3080   -5.4837    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.7853   -4.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6025   -4.8148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.4002   -5.6478    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   39.0931   -3.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0953   -2.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3832   -1.8647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6698   -2.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6731   -3.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3858   -3.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3830   -1.0475    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   39.9976   -2.0633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.1942   -1.9138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.5288   -1.4423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.7012   -2.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4560   -2.8867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6470   -3.6774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.4617   -3.7422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.7751   -2.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1540   -2.4563    0.0000 N   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  1  0
 30 31  2  0
 31 27  1  0
M  CHG  2  23   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4789769

   ---

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: 458.31

Molecular Weight (Monoisotopic): 457.0708

AlogP: 3.51

#Rotatable Bonds: 4

Polar Surface Area: 112.95

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.22

CX Basic pKa: 6.84

CX LogP: 3.11

CX LogD: 3.17

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.41

Np Likeness Score: -0.38

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