2-(4-Fluorophenoxy)-N-[(4-methoxy-2-methylphenylcarbamoyl)methyl]acetamide

ID: ALA3317750

PubChem CID: 89717783

Max Phase: Preclinical

Molecular Formula: C18H19FN2O4

Molecular Weight: 346.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(NC(=O)CNC(=O)COc2ccc(F)cc2)c(C)c1

Standard InChI:  InChI=1S/C18H19FN2O4/c1-12-9-15(24-2)7-8-16(12)21-17(22)10-20-18(23)11-25-14-5-3-13(19)4-6-14/h3-9H,10-11H2,1-2H3,(H,20,23)(H,21,22)

Standard InChI Key:  CEVDRPUZPCFAOV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   11.9812   -6.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2721   -6.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9812   -5.4314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6903   -6.6572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3993   -6.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3993   -5.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1043   -5.0228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6903   -5.0228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8134   -5.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5225   -5.0228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2275   -5.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2275   -6.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5225   -6.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8134   -6.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5225   -4.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9365   -6.6572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6456   -6.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5671   -6.2486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8580   -6.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8580   -7.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1531   -7.8830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4440   -7.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4440   -6.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1531   -6.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7349   -7.8830    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  1  4  1  0
  6  7  1  0
  6  8  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  9 14  2  0
 10 15  1  0
 16 17  1  0
 12 16  1  0
  7  9  1  0
  5  6  1  0
  4  5  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 19 24  2  0
 18 19  1  0
 22 25  1  0
  2 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3317750

   2-[[2-(4-fluorophenoxy)acetyl]amino]-N-(4-methoxy-2-methylphenyl)acetamide

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: 346.36

Molecular Weight (Monoisotopic): 346.1329

AlogP: 2.28

#Rotatable Bonds: 7

Polar Surface Area: 76.66

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.97

CX Basic pKa: ┄

CX LogP: 2.12

CX LogD: 2.12

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.81

Np Likeness Score: -1.88

References

1. Mori H, Wada R, Li J, Ishimoto T, Mizuguchi M, Obita T, Gouda H, Hirono S, Toyooka N..  (2014)  In silico and pharmacological screenings identify novel serine racemase inhibitors.,  24  (16): [PMID:25066953] [10.1016/j.bmcl.2014.07.003]

2.  (2014)  Serine racemase inhibitor, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data