1-Benzyl-3-[3-(3-bromo-propoxy)-4-chloro-1-oxo-1H-isochromen-7-yl]-urea

ID: ALA155099

PubChem CID: 10096054

Max Phase: Preclinical

Molecular Formula: C20H18BrClN2O4

Molecular Weight: 465.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCc1ccccc1)Nc1ccc2c(Cl)c(OCCCBr)oc(=O)c2c1

Standard InChI:  InChI=1S/C20H18BrClN2O4/c21-9-4-10-27-19-17(22)15-8-7-14(11-16(15)18(25)28-19)24-20(26)23-12-13-5-2-1-3-6-13/h1-3,5-8,11H,4,9-10,12H2,(H2,23,24,26)

Standard InChI Key:  HUIGVXGEKDOWGE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    9.5625   -7.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5625   -6.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8000   -6.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8000   -7.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0417   -7.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0417   -6.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9875   -6.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2792   -7.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542   -6.1917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2792   -6.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8000   -5.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2167   -6.1917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5167   -6.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0000   -7.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8000   -8.8417    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.3292   -7.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5167   -7.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4542   -6.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6875   -6.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3875   -7.9667    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   11.8542   -7.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6250   -7.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0917   -7.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9292   -6.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6792   -5.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9125   -4.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1542   -6.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1500   -5.3375    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  9  1  0
  8  5  1  0
  9 13  1  0
 10  6  1  0
 11  3  2  0
 12  7  1  0
 13 17  1  0
 14  7  2  0
 15  4  1  0
 16  1  1  0
 17  8  2  0
 18 12  1  0
 19 18  1  0
 20 22  1  0
 21 23  1  0
 22 21  1  0
 23 16  1  0
 24 19  2  0
 25 19  1  0
 26 25  2  0
 27 24  1  0
 28 26  1  0
  3  6  1  0
 13 10  2  0
 28 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA155099

   1-Benzyl-3-[3-(3-bromopropoxy)-4-chloro-1-oxoisochromen-7-yl]urea

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: 465.73

Molecular Weight (Monoisotopic): 464.0138

AlogP: 4.93

#Rotatable Bonds: 7

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: 4.22

CX LogD: 4.22

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.38

Np Likeness Score: -1.00

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