7-Amino-3-(2-bromo-propoxy)-4-chloro-isochromen-1-one

ID: ALA153354

PubChem CID: 9974046

Max Phase: Preclinical

Molecular Formula: C12H11BrClNO3

Molecular Weight: 332.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(Br)COc1oc(=O)c2cc(N)ccc2c1Cl

Standard InChI:  InChI=1S/C12H11BrClNO3/c1-6(13)5-17-12-10(14)8-3-2-7(15)4-9(8)11(16)18-12/h2-4,6H,5,15H2,1H3

Standard InChI Key:  OEDWZHQYEAKXCH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
    3.0042   -2.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042   -1.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2417   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2417   -2.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4792   -2.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4792   -1.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7667   -2.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7167   -2.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7167   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2417   -0.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2417   -3.7667    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0458   -1.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0458   -2.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292   -2.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8083   -1.1167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -3.7667    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -2.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0667   -2.4417    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  1  1  0
  8  5  1  0
  9  6  1  0
 10  3  2  0
 11  4  1  0
 12 13  1  0
 13  8  2  0
 14  7  1  0
 15 12  1  0
 16 17  1  0
 17 14  1  0
 18 17  1  0
  3  6  1  0
 12  9  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA153354

   7-Amino-3-(2-bromopropoxy)-4-chloroisochromen-1-one

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: 332.58

Molecular Weight (Monoisotopic): 330.9611

AlogP: 3.19

#Rotatable Bonds: 3

Polar Surface Area: 65.46

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.72

CX LogP: 2.89

CX LogD: 2.89

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.69

Np Likeness Score: 0.06

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