5-[3-(2,5-Di(aziridin-1-yl)-3,6-dioxocyclohexa-1,4-dienyl)isoxazol-5-yl]-N-(4-fuorobenzyl)-N-methylthiophene-2-carboxamide

ID: ALA3809646

PubChem CID: 127045075

Max Phase: Preclinical

Molecular Formula: C26H21FN4O4S

Molecular Weight: 504.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(Cc1ccc(F)cc1)C(=O)c1ccc(-c2cc(C3=C(N4CC4)C(=O)C=C(N4CC4)C3=O)no2)s1

Standard InChI:  InChI=1S/C26H21FN4O4S/c1-29(14-15-2-4-16(27)5-3-15)26(34)22-7-6-21(36-22)20-12-17(28-35-20)23-24(31-10-11-31)19(32)13-18(25(23)33)30-8-9-30/h2-7,12-13H,8-11,14H2,1H3

Standard InChI Key:  BOYNKAKWHWXLOY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 36 41  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5987   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9511   -0.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9530   -1.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2010   -3.2957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7343   -2.9815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4458   -1.8433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2720   -0.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7097   -1.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7469   -2.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3323   -3.0387    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9787   -3.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8568   -4.8886    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0634   -2.8795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7721   -5.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0907   -5.7429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5987    1.5004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987   -1.5004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2716    2.7526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0195    1.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0197   -1.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2676   -2.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9688   -7.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2009   -8.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0759   -9.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7190  -10.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4869   -9.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6118   -7.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6190  -11.4243    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  1  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11  7  2  0
  5  7  1  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 12  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 18 20  1  0
 18 21  1  0
  3 22  2  0
  6 23  2  0
  4 24  1  0
  1 25  1  0
 26 24  1  0
 27 26  1  0
 24 27  1  0
 28 25  1  0
 29 28  1  0
 25 29  1  0
 21 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 30  1  0
 33 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3809646

   ---

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: 504.54

Molecular Weight (Monoisotopic): 504.1268

AlogP: 3.19

#Rotatable Bonds: 7

Polar Surface Area: 86.50

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.06

CX LogD: 3.06

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.36

Np Likeness Score: -1.26

References

1. Swapnaja KJ, Yennam S, Chavali M, Poornachandra Y, Kumar CG, Muthusamy K, Jayaraman VB, Arumugam P, Balasubramanian S, Sriram KK..  (2016)  Design, synthesis and biological evaluation of diaziridinyl quinone isoxazole hybrids.,  117  [PMID:27089214] [10.1016/j.ejmech.2016.03.042]

Source

Source(1):

• Scientific Literature