4-[3-(2-Bromo-ethoxy)-4-chloro-1-oxo-1H-isochromen-7-ylcarbamoyl]-butyric acid methyl ester

ID: ALA357115

PubChem CID: 10253017

Max Phase: Preclinical

Molecular Formula: C17H17BrClNO6

Molecular Weight: 446.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)CCCC(=O)Nc1ccc2c(Cl)c(OCCBr)oc(=O)c2c1

Standard InChI:  InChI=1S/C17H17BrClNO6/c1-24-14(22)4-2-3-13(21)20-10-5-6-11-12(9-10)16(23)26-17(15(11)19)25-8-7-18/h5-6,9H,2-4,7-8H2,1H3,(H,20,21)

Standard InChI Key:  CLIISUBHEBQZTF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    7.4792   -6.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4792   -5.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7167   -4.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7167   -6.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9625   -6.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9625   -5.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2000   -6.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -5.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2042   -4.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6750   -4.8917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7167   -4.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1500   -5.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4375   -5.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7167   -7.5417    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -6.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1500   -6.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2500   -6.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4417   -6.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9208   -4.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5417   -6.2167    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.1417   -4.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6125   -4.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3792   -5.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7792   -6.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0125   -6.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9208   -4.0042    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  5  1  0
  8 10  1  0
  9  6  1  0
 10 13  1  0
 11  3  2  0
 12 22  1  0
 13 18  1  0
 14  4  1  0
 15  8  2  0
 16 12  2  0
 17  1  1  0
 18  7  2  0
 19 12  1  0
 20 24  1  0
 21  8  1  0
 22 23  1  0
 23 21  1  0
 24 25  1  0
 25 17  1  0
 26 19  1  0
  3  6  1  0
 13  9  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA357115

   Methyl 5-[[3-(2-bromoethoxy)-4-chloro-1-oxoisochromen-7-yl]amino]-5-oxopentanoate

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: 446.68

Molecular Weight (Monoisotopic): 444.9928

AlogP: 3.50

#Rotatable Bonds: 8

Polar Surface Area: 94.84

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.50

CX Basic pKa: ┄

CX LogP: 2.96

CX LogD: 2.96

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.49

Np Likeness Score: -0.57

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