rac-1-ethyl-N-(1-(4-fluorophenyl)ethyl)-N-methyl-1H-indole-3-carboxamide

ID: ALA4097127

PubChem CID: 42923016

Max Phase: Preclinical

Molecular Formula: C20H21FN2O

Molecular Weight: 324.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCn1cc(C(=O)N(C)C(C)c2ccc(F)cc2)c2ccccc21

Standard InChI:  InChI=1S/C20H21FN2O/c1-4-23-13-18(17-7-5-6-8-19(17)23)20(24)22(3)14(2)15-9-11-16(21)12-10-15/h5-14H,4H2,1-3H3

Standard InChI Key:  BORQPVMVEMIFSR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    6.9711  -11.8296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2279  -11.0455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5585  -10.5588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1460  -11.8296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8938  -11.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0912  -10.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5398  -11.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7968  -12.2700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5989  -12.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4553  -12.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1188  -13.2510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2759  -12.4124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7601  -13.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6123  -11.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4236  -13.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5807  -12.9951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0605  -13.6640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8804  -13.5791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2176  -12.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7289  -12.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9107  -12.2435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0381  -12.7388    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.5568   -9.7337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2704   -9.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0
  1  2  2  0
  2  3  1  0
  3  5  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  1 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 13 15  1  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 19 22  1  0
  3 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4097127

   1-ethyl-N-[1-(4-fluorophenyl)ethyl]-N-methylindole-3-carboxamide

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: 324.40

Molecular Weight (Monoisotopic): 324.1638

AlogP: 4.63

#Rotatable Bonds: 4

Polar Surface Area: 25.24

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.23

CX LogD: 4.23

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.69

Np Likeness Score: -1.72

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