2-(4-chloro-2-fluoro-5-(prop-2-ynyloxy)phenyl)-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione

ID: ALA2269734

Cas Number: 84478-42-2

PubChem CID: 107955

Max Phase: Preclinical

Molecular Formula: C17H13ClFNO3

Molecular Weight: 333.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCOc1cc(N2C(=O)C3=C(CCCC3)C2=O)c(F)cc1Cl

Standard InChI:  InChI=1S/C17H13ClFNO3/c1-2-7-23-15-9-14(13(19)8-12(15)18)20-16(21)10-5-3-4-6-11(10)17(20)22/h1,8-9H,3-7H2

Standard InChI Key:  QAWLSTWQUFLACC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   20.6361  -11.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6361  -12.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3414  -12.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3414  -10.9206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0467  -11.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0467  -12.1516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8248  -12.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3058  -11.7425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8249  -11.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0774  -10.3034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0773  -13.1817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1220  -11.7424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5300  -12.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3465  -12.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7559  -11.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3429  -11.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5278  -11.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5731  -11.7428    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   25.7547  -13.1600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5719  -13.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9801  -13.8683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3884  -14.5762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1173  -10.3304    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
 14 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  3  0
 17 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2269734

   1H-Isoindole-1,3(2H)-dione, 2-(4-chloro-2-fluoro-5-(2-propynyloxy)phenyl)-4,5,6,7-tetrahydro-

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: 333.75

Molecular Weight (Monoisotopic): 333.0568

AlogP: 3.23

#Rotatable Bonds: 3

Polar Surface Area: 46.61

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.00

CX LogP: 3.28

CX LogD: 3.28

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.63

Np Likeness Score: -1.13

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. KOHNO H, OGINO C, IIDA T, TAKASUKA S, SATO Y, NICOLAUS B, BOGER P, WAKABAYASHI K.  (1995)  Peroxidizing Phytotoxic Activity of Pyrazoles,  20  (2): [10.1584/jpestics.20.137]

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