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

ID: ALA2269741

Cas Number: 81663-36-7

PubChem CID: 134032

Max Phase: Preclinical

Molecular Formula: C18H17ClFNO4

Molecular Weight: 365.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)OC(=O)c1cc(N2C(=O)C3=C(CCCC3)C2=O)c(F)cc1Cl

Standard InChI:  InChI=1S/C18H17ClFNO4/c1-9(2)25-18(24)12-7-15(14(20)8-13(12)19)21-16(22)10-5-3-4-6-11(10)17(21)23/h7-9H,3-6H2,1-2H3

Standard InChI Key:  LKXJESTUTBOTSI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    1.7499  -21.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7499  -22.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4552  -22.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4552  -21.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1605  -21.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1605  -22.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9386  -22.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4196  -21.8790    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9387  -21.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1912  -20.4399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1911  -23.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2358  -21.8789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6438  -22.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4603  -22.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8697  -21.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4567  -21.1703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6416  -21.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6869  -21.8792    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.8717  -23.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4627  -24.0059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6889  -23.2988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6455  -24.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2366  -24.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2373  -23.2976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2311  -20.4668    0.0000 F   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
 17 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2269741

   Propan-2-yl 2-chloro-5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2h-isoindol-2-yl)-4-fluorobenzoate

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: 365.79

Molecular Weight (Monoisotopic): 365.0830

AlogP: 3.79

#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: 1.00

CX LogP: 3.99

CX LogD: 3.99

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.60

Np Likeness Score: -0.93

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. 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