(R)-Phenyl-carbamic acid 1-[3-(2-bromo-ethoxy)-4-chloro-1-oxo-1H-isochromen-7-ylcarbamoyl]-ethyl ester

ID: ALA3085278

PubChem CID: 76324349

Max Phase: Preclinical

Molecular Formula: C21H18BrClN2O6

Molecular Weight: 509.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](OC(=O)Nc1ccccc1)C(=O)Nc1ccc2c(Cl)c(OCCBr)oc(=O)c2c1

Standard InChI:  InChI=1S/C21H18BrClN2O6/c1-12(30-21(28)25-13-5-3-2-4-6-13)18(26)24-14-7-8-15-16(11-14)19(27)31-20(17(15)23)29-10-9-22/h2-8,11-12H,9-10H2,1H3,(H,24,26)(H,25,28)/t12-/m1/s1

Standard InChI Key:  VOIQWVHTMKOBBL-GFCCVEGCSA-N

Molfile:  

     RDKit          2D

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    8.8831   -5.8178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4437   -5.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5901   -5.8100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3134   -5.3955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1669   -5.8178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7444   -7.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7282   -5.8100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8824   -5.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7444   -5.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1676   -4.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4437   -4.5550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5901   -6.6271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1676   -7.8822    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.6064   -7.0611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0289   -6.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0087   -5.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7568   -6.6428    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.8824   -4.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0374   -7.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3219   -6.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2932   -5.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0127   -4.5627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2972   -4.1522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4223   -5.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4223   -4.5627    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
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  7 10  1  0
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 13 24  1  6
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 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3085278

   [(2R)-1-[[3-(2-bromoethoxy)-4-chloro-1-oxoisochromen-7-yl]amino]-1-oxopropan-2-yl] N-phenylcarbamate

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: 509.74

Molecular Weight (Monoisotopic): 508.0037

AlogP: 4.80

#Rotatable Bonds: 7

Polar Surface Area: 106.87

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.22

CX Basic pKa: ┄

CX LogP: 4.64

CX LogD: 4.64

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.44

Np Likeness Score: -0.83

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