(2'S,3'R,5'S,6'R)-1-acetyl-6'-benzoyl-4-bromo-5'-hydroxy-3'-phenyl-3',4',5',6'-tetrahydrospiro[indoline-3,2'-thiopyran]-2-one

ID: ALA4539441

PubChem CID: 155550049

Max Phase: Preclinical

Molecular Formula: C27H22BrNO4S

Molecular Weight: 536.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)N1C(=O)[C@@]2(S[C@@H](C(=O)c3ccccc3)[C@@H](O)C[C@@H]2c2ccccc2)c2c(Br)cccc21

Standard InChI:  InChI=1S/C27H22BrNO4S/c1-16(30)29-21-14-8-13-20(28)23(21)27(26(29)33)19(17-9-4-2-5-10-17)15-22(31)25(34-27)24(32)18-11-6-3-7-12-18/h2-14,19,22,25,31H,15H2,1H3/t19-,22+,25-,27+/m1/s1

Standard InChI Key:  KGURWVBOUHASFH-XQKRJCHDSA-N

Molfile:  

 
     RDKit          2D

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   17.1102   -4.3004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4412   -4.3713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8014   -3.8524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6881   -3.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6881   -4.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.3216   -2.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1209   -2.4588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3303   -1.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7418   -1.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9409   -1.2998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7352   -2.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1453   -5.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3249   -5.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8755   -5.7784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   18.0691   -6.5556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5147   -5.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0518   -5.7317    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   17.8454   -3.0286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9743   -4.7137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2592   -4.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9755   -5.5388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9724   -3.0647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2610   -3.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5467   -3.0669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8318   -3.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8357   -4.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5505   -4.7173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2383   -4.1584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8212   -4.7423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4525   -3.3617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  1
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  2  3  1  0
  3  1  1  0
  4  5  1  0
  4  8  1  0
  5  6  1  0
  6  1  1  0
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  7  8  1  0
  7  9  1  6
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 18 19  1  0
 19 20  2  0
 20 15  1  0
 17 21  1  0
  3 22  2  0
  5 23  1  1
 23 24  1  0
 23 25  2  0
  4 26  1  1
 24 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 24  1  0
  2 32  1  0
 32 33  1  0
 32 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4539441

   ---

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: 536.45

Molecular Weight (Monoisotopic): 535.0453

AlogP: 5.07

#Rotatable Bonds: 3

Polar Surface Area: 74.68

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.85

CX Basic pKa: ┄

CX LogP: 4.67

CX LogD: 4.67

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.47

Np Likeness Score: 0.20

References

1. Liu Y, Wang X, Wang G, Yang Y, Yuan Y, Ouyang L..  (2019)  The past, present and future of potential small-molecule drugs targeting p53-MDM2/MDMX for cancer therapy.,  176  [PMID:31100649] [10.1016/j.ejmech.2019.05.018]

Source

Source(1):

• Scientific Literature