(5S,11aR)-9-bromo-2-cyclohexyl-5-(4-methoxyphenyl)-3-thioxo-2,3,5,6,11,11a-hexahydro-1H-imidazo[1',5':1,6]pyrido[3,4-b]indol-1-one

ID: ALA5274468

Max Phase: Preclinical

Molecular Formula: C26H26BrN3O2S

Molecular Weight: 524.48

Names and Identifiers

Canonical SMILES:  COc1ccc([C@H]2c3[nH]c4ccc(Br)cc4c3C[C@@H]3C(=O)N(C4CCCCC4)C(=S)N23)cc1

Standard InChI:  InChI=1S/C26H26BrN3O2S/c1-32-18-10-7-15(8-11-18)24-23-20(19-13-16(27)9-12-21(19)28-23)14-22-25(31)29(26(33)30(22)24)17-5-3-2-4-6-17/h7-13,17,22,24,28H,2-6,14H2,1H3/t22-,24+/m1/s1

Standard InChI Key:  WFMYUKAIOWLABZ-VWNXMTODSA-N

Molfile:  

 
     RDKit          2D

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   -2.6760    0.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9642    0.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9642   -0.8121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6742   -1.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3906   -0.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6944   -0.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8436    1.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0230    1.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4619    0.4403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1262   -0.3134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5387   -1.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3641   -1.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7748   -1.7411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5998   -3.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2467    0.6952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4620    1.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2467    1.5203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9614    1.9329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9614    2.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6760    3.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3906    2.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3906    1.9329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6760    1.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2484    2.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9613    0.2826    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4356    1.8225    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1050    0.4252    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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 11 33  1  1
  1 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5274468

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 524.48

Molecular Weight (Monoisotopic): 523.0929

AlogP: 5.71

#Rotatable Bonds: 3

Polar Surface Area: 48.57

Molecular Species: NEUTRAL

HBA: 3

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: 6.08

CX LogD: 6.08

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.45

Np Likeness Score: -0.43

References

1. Baiazitov RY, Qi H, Arasu T, Lennox W, Cao L, Weetall M, Furia B, Zhuo J, Choi S, Kim MJ, Sheedy J, Davis T, Moon YC..  (2022)  SAR studies toward discovery of emvododstat (PTC299), a potent dihydroorotate dehydrogenase (DHODH) inhibitor.,  244  [PMID:36242990] [10.1016/j.ejmech.2022.114826]

Source

Source(1):

• Scientific Literature