4-[3-(o-Bromo-phenyl)-5-methyl-isoxazol-4-yl]-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester

ID: ALA4101015

PubChem CID: 137658891

Max Phase: Preclinical

Molecular Formula: C23H25BrN2O5

Molecular Weight: 489.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1c1c(-c2ccccc2Br)noc1C

Standard InChI:  InChI=1S/C23H25BrN2O5/c1-6-29-22(27)17-12(3)25-13(4)18(23(28)30-7-2)20(17)19-14(5)31-26-21(19)15-10-8-9-11-16(15)24/h8-11,20,25H,6-7H2,1-5H3

Standard InChI Key:  SAFUGOIRFHJACA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   21.2279   -4.9972    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   19.6038   -6.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2529   -6.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5431   -5.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1707   -7.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6639   -6.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1874   -5.4085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1451   -6.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9394   -6.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0499   -6.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0090   -5.4101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3494   -7.1782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3602   -5.8847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1432   -9.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8455   -7.2487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8695   -8.3138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7926   -6.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0359   -7.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8570   -9.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4251   -7.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2824   -9.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1528   -8.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5845   -7.9154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7338   -8.3166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5634   -9.5566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0060   -7.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2909   -8.3342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9849   -9.5772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0861   -8.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4948   -8.5961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9951   -7.0812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  4  1  0
  4  1  1  0
  5 12  1  0
  9  8  1  0
  3  2  1  0
  7 11  1  0
  3 10  1  0
  4 13  2  0
  7  9  1  0
 13  6  1  0
  2  9  2  0
 10 12  2  0
  6  5  2  0
 11  3  2  0
 15 18  1  0
 16 29  1  0
 21 28  1  0
 27 26  1  0
 26 24  1  0
 20 22  1  0
 21 25  1  0
 24 20  1  0
 27 23  1  0
 29 15  1  0
 19 14  1  0
 23 16  1  0
 21 27  2  0
 19 25  1  0
 16 19  2  0
 18 17  1  0
 29 30  2  0
 23  2  1  0
 26 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4101015

   ---

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: 489.37

Molecular Weight (Monoisotopic): 488.0947

AlogP: 4.77

#Rotatable Bonds: 6

Polar Surface Area: 90.66

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.25

CX LogP: 3.96

CX LogD: 3.96

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.58

Np Likeness Score: -0.71

References

1. Steiger SA, Li C, Backos DS, Reigan P, Natale NR..  (2017)  Dimeric isoxazolyl-1,4-dihydropyridines have enhanced binding at the multi-drug resistance transporter.,  25  (12): [PMID:28434782] [10.1016/j.bmc.2017.04.008]

Source

Source(1):

• Scientific Literature