1-(4-(2-Fluoroethoxy)benzyl)-5-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-ylsulfonyl)indoline-2,3-dione 2,2,2-trifluoroacetate

ID: ALA3133150

PubChem CID: 76322078

Max Phase: Preclinical

Molecular Formula: C25H25F4N3O7S

Molecular Weight: 473.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C(F)(F)F.O=C1C(=O)N(Cc2ccc(OCCF)cc2)c2ccc(S(=O)(=O)N3CC4CNCC4C3)cc21

Standard InChI:  InChI=1S/C23H24FN3O5S.C2HF3O2/c24-7-8-32-18-3-1-15(2-4-18)12-27-21-6-5-19(9-20(21)22(28)23(27)29)33(30,31)26-13-16-10-25-11-17(16)14-26;3-2(4,5)1(6)7/h1-6,9,16-17,25H,7-8,10-14H2;(H,6,7)

Standard InChI Key:  NRDVAJOENOZFEL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 40 43  0  0  0  0  0  0  0  0999 V2000
   19.5084   -5.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2226   -5.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5091   -4.6493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7937   -5.8863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9374   -5.4754    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.2220   -6.7123    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.9371   -6.2998    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.6648   -1.7043    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.0492   -0.9743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2248   -1.0064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3947   -2.0887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4255   -2.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1557   -3.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0901   -1.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8209   -2.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8530   -2.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6484   -3.0804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1078   -2.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5964   -1.7442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9323   -2.3612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8205   -0.9502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0087   -2.2046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2184   -1.9636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0280   -3.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9351   -3.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5127   -4.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6879   -4.5461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2655   -5.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6680   -5.9752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4973   -5.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9160   -5.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2465   -6.6844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4216   -6.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0000   -7.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1750   -7.3727    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.2495   -3.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7543   -2.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9772   -2.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9922   -3.7324    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7785   -3.9720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  1  4  1  0
  2  5  1  0
  2  6  1  0
  2  7  1  0
  9  8  2  0
  8 10  2  0
 11 12  2  0
 12 13  1  0
 13 16  2  0
 15 14  2  0
 14 11  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 15  1  0
 18 20  2  0
 19 21  2  0
 11  8  1  0
  8 22  1  0
 22 23  1  0
 23 37  1  0
 36 24  1  0
 24 22  1  0
 17 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 29 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 40 36  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 473.53

Molecular Weight (Monoisotopic): 473.1421

AlogP: 1.60

#Rotatable Bonds: 7

Polar Surface Area: 96.02

Molecular Species: BASE

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 11.06

CX LogP: 0.83

CX LogD: -2.28

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.61

Np Likeness Score: -1.16

References

1. Krause-Heuer AM, Howell NR, Matesic L, Dhand G, Young EL, Burgess L, Jiang CD, Lengkeek NA, Fookes CJR, Pham TQ, Sobrio F, Greguric I, Fraser BH.  (2013)  A new class of fluorinated 5-pyrrolidinylsulfonyl isatin caspase inhibitors for PET imaging of apoptosis,  4  (2): [10.1039/C2MD20249B]

Source

Source(1):

• Scientific Literature