rac-4-(4-chlorobenzoyl)-1-(2,5-dimethoxyphenyl)-3-methylpiperazin-2-one

ID: ALA4091399

PubChem CID: 46036431

Max Phase: Preclinical

Molecular Formula: C20H21ClN2O4

Molecular Weight: 388.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(OC)c(N2CCN(C(=O)c3ccc(Cl)cc3)C(C)C2=O)c1

Standard InChI:  InChI=1S/C20H21ClN2O4/c1-13-19(24)23(17-12-16(26-2)8-9-18(17)27-3)11-10-22(13)20(25)14-4-6-15(21)7-5-14/h4-9,12-13H,10-11H2,1-3H3

Standard InChI Key:  VBILMTNSWHFDNE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.4958  -11.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4958  -12.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2079  -12.9126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9199  -12.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9199  -11.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2079  -11.2626    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7819  -12.9177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7801  -11.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2079  -10.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2079  -13.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4934  -14.1501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9223  -14.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9181  -14.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6317  -15.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3472  -14.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3445  -14.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6303  -13.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9244  -10.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9247   -9.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2098   -8.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4929   -9.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4961  -10.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7829  -10.4434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0672  -10.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6394   -8.7902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3538   -9.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0622  -15.3875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  2  7  1  0
  1  8  2  0
  6  9  1  0
  3 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
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 14 15  2  0
 15 16  1  0
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 17 12  1  0
  9 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
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 23 24  1  0
 19 25  1  0
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 15 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4091399

   4-(4-Chlorobenzoyl)-1-(2,5-dimethoxyphenyl)-3-methylpiperazin-2-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: 388.85

Molecular Weight (Monoisotopic): 388.1190

AlogP: 3.23

#Rotatable Bonds: 4

Polar Surface Area: 59.08

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.73

CX LogD: 2.73

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.81

Np Likeness Score: -1.12

References

1. Fujimoto J, Okamoto R, Noguchi N, Hara R, Masada S, Kawamoto T, Nagase H, Tamura YO, Imanishi M, Takagahara S, Kubo K, Tohyama K, Iida K, Andou T, Miyahisa I, Matsui J, Hayashi R, Maekawa T, Matsunaga N..  (2017)  Discovery of 3,5-Diphenyl-4-methyl-1,3-oxazolidin-2-ones as Novel, Potent, and Orally Available Δ-5 Desaturase (D5D) Inhibitors.,  60  (21): [PMID:29023121] [10.1021/acs.jmedchem.7b01210]

Source

Source(1):

• Scientific Literature