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

ID: ALA3317735

PubChem CID: 71696075

Max Phase: Preclinical

Molecular Formula: C18H19BrN2O4

Molecular Weight: 407.26

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H19BrN2O4/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:  OCCKGEJURKCBTP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   10.5294   -5.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8203   -5.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5294   -4.7174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2384   -5.9432    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9434   -5.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9434   -4.7174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6525   -4.3088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2384   -4.3088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3616   -4.7174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0665   -4.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7756   -4.7174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7756   -5.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0665   -5.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3616   -5.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0665   -3.4916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4847   -5.9432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1897   -5.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1153   -5.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4062   -5.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4062   -6.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7013   -7.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9922   -6.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9922   -5.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7013   -5.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2831   -7.1690    0.0000 Br  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:

   

   ALA3317735

   2-[[2-(4-bromophenoxy)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: 407.26

Molecular Weight (Monoisotopic): 406.0528

AlogP: 2.90

#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: 11.93

CX Basic pKa: ┄

CX LogP: 2.75

CX LogD: 2.75

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.74

Np Likeness Score: -1.68

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