ethyl 2-(3-(aminomethyl)phenyl)-4-bromobenzo[d]oxazole-6-carboxylate

ID: ALA4537639

PubChem CID: 44126153

Max Phase: Preclinical

Molecular Formula: C17H15BrN2O3

Molecular Weight: 375.22

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cc(Br)c2nc(-c3cccc(CN)c3)oc2c1

Standard InChI:  InChI=1S/C17H15BrN2O3/c1-2-22-17(21)12-7-13(18)15-14(8-12)23-16(20-15)11-5-3-4-10(6-11)9-19/h3-8H,2,9,19H2,1H3

Standard InChI Key:  XHVNOKLBERHFEA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   15.5913   -2.5093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5901   -3.3289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2982   -3.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2964   -2.1005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0050   -2.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0098   -3.3243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7898   -3.5728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2672   -2.9077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7821   -2.2483    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0824   -2.9023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4945   -3.6093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3109   -3.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7162   -2.8941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2990   -2.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4840   -2.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7009   -1.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5181   -1.4673    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2939   -1.2833    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   14.8821   -3.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1747   -3.3277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8814   -4.5541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1753   -2.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4680   -2.1014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  8 10  1  0
 14 16  1  0
 16 17  1  0
  4 18  1  0
  2 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4537639

   Ethyl 2-[3-(aminomethyl)phenyl]-4-bromo-1,3-benzoxazole-6-carboxylate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 375.22

Molecular Weight (Monoisotopic): 374.0266

AlogP: 3.89

#Rotatable Bonds: 4

Polar Surface Area: 78.35

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.08

CX LogP: 3.60

CX LogD: 1.93

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.70

Np Likeness Score: -0.81

References

1. Ameryckx A, Thabault L, Pochet L, Leimanis S, Poupaert JH, Wouters J, Joris B, Van Bambeke F, Frédérick R..  (2018)  1-(2-Hydroxybenzoyl)-thiosemicarbazides are promising antimicrobial agents targeting d-alanine-d-alanine ligase in bacterio.,  159  [PMID:30300845] [10.1016/j.ejmech.2018.09.067]

Source

Source(1):

• Scientific Literature