1-[3-(2-Bromo-ethoxy)-4-chloro-1-oxo-1H-isochromen-7-yl]-3-tert-butyl-urea

ID: ALA153575

PubChem CID: 10251416

Max Phase: Preclinical

Molecular Formula: C16H18BrClN2O4

Molecular Weight: 417.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)NC(=O)Nc1ccc2c(Cl)c(OCCBr)oc(=O)c2c1

Standard InChI:  InChI=1S/C16H18BrClN2O4/c1-16(2,3)20-15(22)19-9-4-5-10-11(8-9)13(21)24-14(12(10)18)23-7-6-17/h4-5,8H,6-7H2,1-3H3,(H2,19,20,22)

Standard InChI Key:  GSTIQPIVHZFIKI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    4.7667   -6.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7667   -5.1167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0042   -4.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0042   -6.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417   -6.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417   -5.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1917   -5.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542   -4.6750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5750   -4.6750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792   -6.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4875   -4.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0042   -3.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7167   -5.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1917   -6.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3375   -5.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0042   -7.3250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.5292   -6.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7250   -6.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8292   -6.0042    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333   -5.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1083   -4.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4833   -5.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0625   -6.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917   -6.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  1  2  0
  5  4  1  0
  6  5  2  0
  7  8  1  0
  8 13  1  0
  9  7  1  0
 10  5  1  0
 11  6  1  0
 12  3  2  0
 13 18  1  0
 14  7  2  0
 15  9  1  0
 16  4  1  0
 17  1  1  0
 18 10  2  0
 19 23  1  0
 20 15  1  0
 21 15  1  0
 22 15  1  0
 23 24  1  0
 24 17  1  0
  3  6  1  0
 13 11  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA153575

   1-[3-(2-Bromoethoxy)-4-chloro-1-oxoisochromen-7-yl]-3-tert-butylurea

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: 417.69

Molecular Weight (Monoisotopic): 416.0138

AlogP: 4.14

#Rotatable Bonds: 4

Polar Surface Area: 80.57

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.81

CX Basic pKa: ┄

CX LogP: 3.49

CX LogD: 3.49

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.73

Np Likeness Score: -0.93

References

1. Kerrigan JE, Oleksyszyn J, Kam CM, Selzler J, Powers JC..  (1995)  Mechanism-based isocoumarin inhibitors for human leukocyte elastase. Effect of the 7-amino substituent and 3-alkoxy group in 3-alkoxy-7-amino-4-chloroisocoumarins on inhibitory potency.,  38  (3): [PMID:7853347] [10.1021/jm00003a017]

Source

Source(1):

• Scientific Literature