isopropyl 2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)benzoate

ID: ALA2269750

PubChem CID: 12819080

Max Phase: Preclinical

Molecular Formula: C18H18ClNO4

Molecular Weight: 347.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)OC(=O)c1cc(N2C(=O)C3=C(CCCC3)C2=O)ccc1Cl

Standard InChI:  InChI=1S/C18H18ClNO4/c1-10(2)24-18(23)14-9-11(7-8-15(14)19)20-16(21)12-5-3-4-6-13(12)17(20)22/h7-10H,3-6H2,1-2H3

Standard InChI Key:  GZOMDEWNWODVJF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    0.6026   -5.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6026   -6.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3079   -6.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3079   -5.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0131   -5.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0131   -6.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7913   -6.5521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2723   -5.8901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7913   -5.2282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0439   -4.4510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0437   -7.3293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0885   -5.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4965   -6.5993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3129   -6.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7223   -5.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3093   -5.1814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4942   -5.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5395   -5.8904    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.7243   -7.3095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3154   -8.0170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5415   -7.3099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4982   -8.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0892   -8.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0899   -7.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  9 10  2  0
  7 11  2  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  8 12  1  0
 15 18  1  0
 19 20  1  0
 19 21  2  0
 14 19  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2269750

   Propan-2-yl 2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)benzoate

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: 347.80

Molecular Weight (Monoisotopic): 347.0924

AlogP: 3.65

#Rotatable Bonds: 3

Polar Surface Area: 63.68

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.17

CX LogP: 3.84

CX LogD: 3.84

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.62

Np Likeness Score: -1.00

References

1. ISHIDA S, IIDA T, KOHNO H, SATO Y, KUBO H, BOGER P, WAKABAYASHI K.  (1999)  Comparison of Phytotoxicities between 4-Fluorinated and Non-fluorinated 2-Chloro-5-(3, 4, 5, 6-tetrahydrophthalimido)benzoates,  24  (1): [10.1584/jpestics.24.28]

2. MIYAMOTO Y, IKEDA Y, WAKABAYASHI K.  (2003)  Synthesis and Phytotoxic Activities of N-Substituted Phenyl Isothiazolone Derivatives,  28  (3): [10.1584/jpestics.28.293]

3. ISHIDA S, HIRAI K, KOHNO H, SATO Y, KUBO H, BOGER P, WAKABAYASHI K.  (1997)  Protoporphyrinogen-IX Oxidase Inhibition by N-(2, 4, 5-Trisubstituted phenyl)-3, 4, 5, 6-tetrahydrophthalimides,  22  (4): [10.1584/jpestics.22.299]

Source

Source(1):

• Scientific Literature