2-(4-Chloro-5-cyclopentyloxy-2-fluorophenyl)-tetrahydropyrrolo[1,2-a]pyrazine-1,3(2H,4H)-dione

ID: ALA2270103

PubChem CID: 76319650

Max Phase: Preclinical

Molecular Formula: C18H20ClFN2O3

Molecular Weight: 366.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1CN2CCCC2C(=O)N1c1cc(OC2CCCC2)c(Cl)cc1F

Standard InChI:  InChI=1S/C18H20ClFN2O3/c19-12-8-13(20)15(9-16(12)25-11-4-1-2-5-11)22-17(23)10-21-7-3-6-14(21)18(22)24/h8-9,11,14H,1-7,10H2

Standard InChI Key:  KVLOLWBSRBURSY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    4.3289  -15.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1539  -15.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5663  -15.7172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1539  -16.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5663  -14.2897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5663  -17.1489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3913  -15.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8038  -15.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6288  -15.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0413  -15.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6288  -16.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8038  -16.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3913  -14.2897    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.8662  -15.7172    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.0416  -17.1474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8666  -17.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3531  -17.8130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1376  -17.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1372  -16.7327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3525  -16.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3286  -16.4331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9145  -15.7144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1030  -15.8860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0154  -16.7110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7730  -17.0489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1 22  1  0
  2  3  1  0
  3  4  1  0
  4 21  1  0
  2  5  2  0
  4  6  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  7 12  2  0
  8 13  1  0
 10 14  1  0
  3  7  1  0
 11 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 16  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2270103

   2-(4-chloro-5-cyclopentyloxy-2-fluorophenyl)-6,7,8,8a-tetrahydro-4H-pyrrolo[1,2-a]pyrazine-1,3-dione

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: 366.82

Molecular Weight (Monoisotopic): 366.1146

AlogP: 3.14

#Rotatable Bonds: 3

Polar Surface Area: 49.85

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.02

CX LogP: 2.99

CX LogD: 2.99

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.77

Np Likeness Score: -0.57

References

1. Li B, Xiang D, Hsu CT, Liu ZL, Wu C, Yang HZ..  (2005)  A facile synthesis of novel herbicidal 1-phenyl-piperazine-2,6-diones.,  10  (9): [PMID:18007377] [10.3390/10091119]

Source

Source(1):

• Scientific Literature