(S)-dimethyl 2-(2-(2-acetamidophenyl)-2-oxoacetamido)succinate

ID: ALA3577036

PubChem CID: 101537371

Max Phase: Preclinical

Molecular Formula: C16H18N2O7

Molecular Weight: 350.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C[C@H](NC(=O)C(=O)c1ccccc1NC(C)=O)C(=O)OC

Standard InChI:  InChI=1S/C16H18N2O7/c1-9(19)17-11-7-5-4-6-10(11)14(21)15(22)18-12(16(23)25-3)8-13(20)24-2/h4-7,12H,8H2,1-3H3,(H,17,19)(H,18,22)/t12-/m0/s1

Standard InChI Key:  MGPQVZXDXKBJGP-LBPRGKRZSA-N

Molfile:  

     RDKit          2D

 25 25  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5973    1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5548   -3.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933   -3.7570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5916   -6.0087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5912   -7.5095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5524   -5.4087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5521   -8.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1872   -7.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4854   -8.2648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1469   -8.1099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4837   -9.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951    3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6331    3.6060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5549    3.6021    0.0000 C   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
  4  7  1  0
  5  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 15 17  2  0
 16 18  1  0
 14 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
  7 23  1  0
 23 24  2  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3577036

   dimethyl (2S)-2-[[2-(2-acetamidophenyl)-2-oxoacetyl]amino]butanedioate

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: 350.33

Molecular Weight (Monoisotopic): 350.1114

AlogP: 0.05

#Rotatable Bonds: 7

Polar Surface Area: 127.87

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.13

CX Basic pKa: ┄

CX LogP: 0.49

CX LogD: 0.49

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.40

Np Likeness Score: -0.48

References

1. El-Faham A, Zainab Al Marhoon, Abdel-Megeed A, Khattab SN, Bekhit AA, Albericio F..  (2014)  α-Ketoamino acid ester derivatives as promising MAO inhibitors.,  25  (1): [PMID:25466194] [10.1016/j.bmcl.2014.11.007]

Source

Source(1):

• Scientific Literature