2'-tert-butyl-1-(2,4-dimethyl-1H-benzo[d]imidazole-6-carbonyl)-2'H-spiro[piperidine-4,5'-pyrano[3,2-c]pyrazol]-7'(6'H)-one

ID: ALA1958374

PubChem CID: 56949781

Max Phase: Preclinical

Molecular Formula: C24H29N5O3

Molecular Weight: 435.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc2c(C)cc(C(=O)N3CCC4(CC3)CC(=O)c3nn(C(C)(C)C)cc3O4)cc2[nH]1

Standard InChI:  InChI=1S/C24H29N5O3/c1-14-10-16(11-17-20(14)26-15(2)25-17)22(31)28-8-6-24(7-9-28)12-18(30)21-19(32-24)13-29(27-21)23(3,4)5/h10-11,13H,6-9,12H2,1-5H3,(H,25,26)

Standard InChI Key:  ZPQBARADSDTGBA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    0.8125  -22.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8132  -23.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5240  -23.9263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2388  -23.5155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2381  -22.6905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5227  -22.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1037  -23.1000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8157  -21.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1037  -21.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6083  -22.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6083  -21.8621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3973  -21.6057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8850  -22.2768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3973  -22.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9530  -23.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9525  -24.7534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6677  -23.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3776  -23.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3735  -22.2812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6623  -22.6949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8711  -23.7768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3591  -23.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8783  -22.4436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0928  -22.6939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0881  -23.5183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1057  -20.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7100  -22.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1225  -21.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3711  -21.4562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1225  -22.9913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5375  -22.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1841  -23.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4 15  1  0
  1  6  1  0
 15 16  2  0
 11  9  1  0
 15 17  1  0
 10  7  1  0
 17 18  2  0
 18 25  1  0
  7  1  1  0
 24 19  1  0
  1  8  1  0
 19 20  2  0
 20 17  1  0
 24 25  2  0
  8  9  1  0
 10 11  1  0
 22 23  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
 21 22  1  0
 23 24  1  0
 25 21  1  0
  5  6  1  0
  9 26  2  0
 13 27  1  0
 11 12  2  0
 27 28  1  0
 12 13  1  0
 19 29  1  0
 13 14  1  0
 27 30  1  0
 14 10  2  0
 27 31  1  0
  1  2  1  0
 22 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1958374

   2-tert-butyl-1'-(2,7-dimethyl-3H-benzimidazole-5-carbonyl)spiro[6H-pyrano[3,2-c]pyrazole-5,4'-piperidine]-7-one

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: 435.53

Molecular Weight (Monoisotopic): 435.2270

AlogP: 3.77

#Rotatable Bonds: 1

Polar Surface Area: 93.11

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.85

CX Basic pKa: 6.31

CX LogP: 2.13

CX LogD: 2.10

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.63

Np Likeness Score: -1.19

References

1. Freeman-Cook KD, Amor P, Bader S, Buzon LM, Coffey SB, Corbett JW, Dirico KJ, Doran SD, Elliott RL, Esler W, Guzman-Perez A, Henegar KE, Houser JA, Jones CS, Limberakis C, Loomis K, McPherson K, Murdande S, Nelson KL, Phillion D, Pierce BS, Song W, Sugarman E, Tapley S, Tu M, Zhao Z..  (2012)  Maximizing lipophilic efficiency: the use of Free-Wilson analysis in the design of inhibitors of acetyl-CoA carboxylase.,  55  (2): [PMID:22148323] [10.1021/jm201503u]

Source

Source(1):

• Scientific Literature