N1-(benzo[d][1,3]dioxol-5-yl)-N2-(2,2,6,6-tetramethylpiperidin-4-yl)oxalamide hydrochloride

ID: ALA3754675

PubChem CID: 127037579

Max Phase: Preclinical

Molecular Formula: C18H26ClN3O4

Molecular Weight: 347.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CC(NC(=O)C(=O)Nc2ccc3c(c2)OCO3)CC(C)(C)N1.Cl

Standard InChI:  InChI=1S/C18H25N3O4.ClH/c1-17(2)8-12(9-18(3,4)21-17)20-16(23)15(22)19-11-5-6-13-14(7-11)25-10-24-13;/h5-7,12,21H,8-10H2,1-4H3,(H,19,22)(H,20,23);1H

Standard InChI Key:  DRMSDNAKUKBTCJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    5.0889   -3.7142    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6187   -1.4919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6267   -2.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9300   -3.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5905   -3.5979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9380   -5.2378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9662   -3.1317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2413   -5.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2516   -7.4820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5557   -8.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8496   -7.4644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8394   -5.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5354   -5.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8684   -6.5819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8031   -4.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5065   -8.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6126   -8.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  7  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  6  1  0
  4 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 13 16  2  0
 15 17  1  0
 17 18  1  0
 17 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 19 25  1  0
 19 26  1  0
M  END

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: 347.42

Molecular Weight (Monoisotopic): 347.1845

AlogP: 1.78

#Rotatable Bonds: 2

Polar Surface Area: 88.69

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.32

CX Basic pKa: 10.33

CX LogP: 0.98

CX LogD: -1.55

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.71

Np Likeness Score: -1.12

References

1. Mizuguchi T, Harada S, Miura T, Ohashi N, Narumi T, Mori H, Irahara Y, Yamada Y, Nomura W, Matsushita S, Yoshimura K, Tamamura H..  (2016)  A minimally cytotoxic CD4 mimic as an HIV entry inhibitor.,  26  (2): [PMID:26706175] [10.1016/j.bmcl.2015.11.103]

Source

Source(1):

• Scientific Literature