1-(3,7-Dimethyl-1H-indole-5-carbonyl)-2'-ethyl-3'-methyl-2'H-spiro[piperidine-4,5'-pyrano[3,2,c]pyrazol]-7'(6'H)-one

ID: ALA1958368

PubChem CID: 44519663

Max Phase: Preclinical

Molecular Formula: C24H28N4O3

Molecular Weight: 420.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCn1nc2c(c1C)OC1(CCN(C(=O)c3cc(C)c4[nH]cc(C)c4c3)CC1)CC2=O

Standard InChI:  InChI=1S/C24H28N4O3/c1-5-28-16(4)22-21(26-28)19(29)12-24(31-22)6-8-27(9-7-24)23(30)17-10-14(2)20-18(11-17)15(3)13-25-20/h10-11,13,25H,5-9,12H2,1-4H3

Standard InChI Key:  DXOPPMVNXZZJRP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -0.3077   -7.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4032   -8.3680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1180   -7.9572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4019   -6.7180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0171   -7.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3051   -6.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7292   -7.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7291   -6.3038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5181   -6.0473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8317   -9.1951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5414   -7.1366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7502   -8.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2383   -7.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7574   -6.8852    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9720   -7.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9673   -7.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0152   -5.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8308   -6.7185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2433   -6.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7731   -8.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2503   -5.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1618   -8.9336    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
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 17 18  2  0
 18 25  1  0
  7  1  1  0
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  1  8  1  0
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  2  3  1  0
  3  4  1  0
  4  5  1  0
 21 22  2  0
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 25 21  1  0
  5  6  1  0
  9 26  2  0
 13 27  1  0
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 27 28  1  0
 12 13  1  0
 14 29  1  0
 13 14  1  0
 19 30  1  0
 14 10  2  0
 21 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1958368

   1'-(3,7-dimethyl-1H-indole-5-carbonyl)-2-ethyl-3-methylspiro[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: 420.51

Molecular Weight (Monoisotopic): 420.2161

AlogP: 3.95

#Rotatable Bonds: 2

Polar Surface Area: 80.22

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.84

CX LogD: 2.84

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.68

Np Likeness Score: -1.06

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