Rac-(3S,3'S,4'S,5'S)-4'-amino-6-chloro-3'-(3-chloro-2-fluorophenyl)-1'-[(3-ethoxyphenyl)methyl]-5'-methyl-1,2-dihydrospiro[indole-3,2'-pyrrolidine]-2-one

ID: ALA4756922

PubChem CID: 122198472

Max Phase: Preclinical

Molecular Formula: C27H26Cl2FN3O2

Molecular Weight: 514.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOc1cccc(CN2[C@@H](C)[C@@H](N)[C@H](c3cccc(Cl)c3F)[C@]23C(=O)Nc2cc(Cl)ccc23)c1

Standard InChI:  InChI=1S/C27H26Cl2FN3O2/c1-3-35-18-7-4-6-16(12-18)14-33-15(2)25(31)23(19-8-5-9-21(29)24(19)30)27(33)20-11-10-17(28)13-22(20)32-26(27)34/h4-13,15,23,25H,3,14,31H2,1-2H3,(H,32,34)/t15-,23-,25+,27+/m0/s1

Standard InChI Key:  VTZPRLPCZBTKSH-VFICKSILSA-N

Molfile:  

 
     RDKit          2D

 35 39  0  0  0  0  0  0  0  0999 V2000
   34.9746  -19.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7449  -19.1990    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.7242  -18.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9410  -18.1495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4778  -18.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7812  -19.7322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7800  -20.5518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4881  -20.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4863  -19.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1949  -19.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1997  -20.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9797  -20.7957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.4571  -20.1306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2743  -20.1268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.0720  -20.9598    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   33.7649  -18.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7670  -17.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0549  -17.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3416  -17.5888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3448  -18.4159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0575  -18.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0547  -16.3595    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   34.6694  -17.3753    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.4180  -19.6624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1559  -19.3112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3730  -17.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9753  -16.7937    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   37.8235  -19.7773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5609  -19.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6262  -18.6113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9481  -18.1477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2135  -18.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2337  -19.8905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.1685  -20.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8414  -21.1689    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
  4 23  1  6
  2 24  1  0
 24 25  1  0
  3 26  1  6
 17 27  1  0
 25 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 25  1  0
 29 33  1  0
 33 34  1  0
 34 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4756922

   ---

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: 514.43

Molecular Weight (Monoisotopic): 513.1386

AlogP: 5.69

#Rotatable Bonds: 5

Polar Surface Area: 67.59

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.30

CX Basic pKa: 8.88

CX LogP: 5.60

CX LogD: 4.12

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.46

Np Likeness Score: -0.64

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]

2. 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