N-[3-(3-Bromo-propoxy)-4-chloro-1-oxo-1H-isochromen-7-yl]-acetamide

ID: ALA357068

PubChem CID: 10452068

Max Phase: Preclinical

Molecular Formula: C14H13BrClNO4

Molecular Weight: 374.62

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C14H13BrClNO4/c1-8(18)17-9-3-4-10-11(7-9)13(19)21-14(12(10)16)20-6-2-5-15/h3-4,7H,2,5-6H2,1H3,(H,17,18)

Standard InChI Key:  RVGFAGHJOWDELH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  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
    7.2792   -7.9542    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   -6.1917    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
    8.8000   -5.3042    0.0000 O   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
    8.8000   -8.8417    0.0000 Cl  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
   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
   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
    4.2167   -6.1917    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
  2  1  1  0
  3  2  1  0
  4  1  2  0
  5  4  1  0
  6  5  2  0
  7  5  1  0
  8 10  1  0
  9  6  1  0
 10 12  1  0
 11  3  2  0
 12 16  1  0
 13  4  1  0
 14  8  2  0
 15  1  1  0
 16  7  2  0
 17 20  1  0
 18 21  1  0
 19  8  1  0
 20 18  1  0
 21 15  1  0
  6  3  1  0
  9 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA357068

   N-[3-(3-Bromopropyloxy)-4-chloro-1-oxo-1H-2-benzopyran-7-yl]ethanamide

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: 374.62

Molecular Weight (Monoisotopic): 372.9716

AlogP: 3.57

#Rotatable Bonds: 5

Polar Surface Area: 68.54

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.66

CX Basic pKa: ┄

CX LogP: 2.60

CX LogD: 2.60

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.64

Np Likeness Score: -0.63

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