Rac-(4-Benzyl-3-hydroxypiperidin-1-yl)(5-methyl-2-(pyridin-4-yl)-phenyl)methanone

ID: ALA5286208

Max Phase: Preclinical

Molecular Formula: C25H26N2O2

Molecular Weight: 386.50

Names and Identifiers

Canonical SMILES:  Cc1ccc(-c2ccncc2)c(C(=O)N2CCC(Cc3ccccc3)C(O)C2)c1

Standard InChI:  InChI=1S/C25H26N2O2/c1-18-7-8-22(20-9-12-26-13-10-20)23(15-18)25(29)27-14-11-21(24(28)17-27)16-19-5-3-2-4-6-19/h2-10,12-13,15,21,24,28H,11,14,16-17H2,1H3

Standard InChI Key:  OOCBPPHXWOWQET-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    6.5038  -11.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2165  -11.6869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9310  -11.2746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9281  -10.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2147  -10.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2183  -12.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5041  -12.9179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5035  -13.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2164  -14.1521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9313  -13.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9284  -12.9160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2123   -9.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7909  -11.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7903  -12.5086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0789  -11.2740    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0789  -10.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3709  -10.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6557  -10.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6530  -11.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3656  -11.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9451  -10.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2308  -10.4360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5207  -10.0236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8068  -10.4309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8027  -11.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5183  -11.6690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2291  -11.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3746   -9.2127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  3  7  1  0
  6 13  1  0
  2 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 18 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5286208

   ---

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: 386.50

Molecular Weight (Monoisotopic): 386.1994

AlogP: 4.12

#Rotatable Bonds: 4

Polar Surface Area: 53.43

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.73

CX LogP: 3.93

CX LogD: 3.93

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.73

Np Likeness Score: -0.47

References

1. Koike T, Yoshikawa M, Ando HK, Farnaby W, Nishi T, Watanabe E, Yano J, Miyamoto M, Kondo S, Ishii T, Kuroita T..  (2021)  Discovery of Soticlestat, a Potent and Selective Inhibitor for Cholesterol 24-Hydroxylase (CH24H).,  64  (16.0): [PMID:34387987] [10.1021/acs.jmedchem.1c00864]

Source

Source(1):

• Scientific Literature