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

ID: ALA1958373

PubChem CID: 56949780

Max Phase: Preclinical

Molecular Formula: C23H27N5O3

Molecular Weight: 421.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C(=O)N2CCC3(CC2)CC(=O)c2nn(C(C)(C)C)cc2O3)cc2[nH]cnc12

Standard InChI:  InChI=1S/C23H27N5O3/c1-14-9-15(10-16-19(14)25-13-24-16)21(30)27-7-5-23(6-8-27)11-17(29)20-18(31-23)12-28(26-20)22(2,3)4/h9-10,12-13H,5-8,11H2,1-4H3,(H,24,25)

Standard InChI Key:  PKMRYIWYGLMGNW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   14.1167  -18.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1173  -19.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8282  -19.9930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5430  -19.5822    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5423  -18.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8269  -18.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4079  -19.1667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1199  -17.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4079  -17.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6958  -18.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6959  -17.9288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9069  -17.6723    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4192  -18.3435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9068  -19.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2572  -19.9951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2567  -20.8201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9719  -19.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6818  -19.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6777  -18.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9664  -18.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1752  -19.8435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6633  -19.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1824  -18.5102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3970  -18.7606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3923  -19.5850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4098  -16.6917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5942  -18.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1817  -17.6290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6753  -17.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1817  -19.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7667  -18.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
M  END

Alternative Forms

1. Parent:

   

   ALA1958373

   2-tert-butyl-1'-(7-methyl-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: 421.50

Molecular Weight (Monoisotopic): 421.2114

AlogP: 3.46

#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: 11.41

CX Basic pKa: 5.79

CX LogP: 2.01

CX LogD: 2.00

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.65

Np Likeness Score: -1.13

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