(2S,6R)-4-((3,5-dimethylisoxazol-4-yl)methoxy)-2,6-difluorobenzyl 2,6-dimethylpiperazine-1-carboxylate

ID: ALA1091452

PubChem CID: 9844378

Max Phase: Preclinical

Molecular Formula: C20H25F2N3O4

Molecular Weight: 409.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1noc(C)c1COc1cc(F)c(COC(=O)N2[C@H](C)CNC[C@@H]2C)c(F)c1

Standard InChI:  InChI=1S/C20H25F2N3O4/c1-11-7-23-8-12(2)25(11)20(26)28-10-17-18(21)5-15(6-19(17)22)27-9-16-13(3)24-29-14(16)4/h5-6,11-12,23H,7-10H2,1-4H3/t11-,12+

Standard InChI Key:  IIHSKABITVJBTL-TXEJJXNPSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -2.3431    1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3443    1.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6294    0.6640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9130    1.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9159    1.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6312    2.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0591    0.6649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2029    2.3230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5131    1.9132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6337    3.1420    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1979    0.6659    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7732    1.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4880    0.6663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2673    0.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7673    0.2824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2976   -0.3960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5075   -0.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8514   -0.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5046    1.7287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2260    2.3284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9420    1.9186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2229    3.1534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9428    1.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6547    0.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700    1.0925    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3689    1.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6524    2.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2288    0.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6510    3.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  7  1  0
  3  4  2  0
  5  8  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 13  2  0
 17 18  1  0
  8  9  1  0
 14 19  1  0
  4  5  1  0
  9 20  1  0
  6 10  1  0
 20 21  1  0
  2  3  1  0
 20 22  2  0
 21 23  1  0
  4 11  1  0
  5  6  2  0
  7 12  1  0
  6  1  1  0
 12 13  1  0
 21 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 13 14  1  0
 23 28  1  6
  1  2  2  0
 27 29  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1091452

   (2S,6R)-4-((3,5-dimethylisoxazol-4-yl)methoxy)-2,6-difluorobenzyl 2,6-dimethylpiperazine-1-carboxylate

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: 409.43

Molecular Weight (Monoisotopic): 409.1813

AlogP: 3.47

#Rotatable Bonds: 5

Polar Surface Area: 76.83

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.08

CX LogP: 2.61

CX LogD: 1.85

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.82

Np Likeness Score: -1.15

References

1. Liu KK, Lefker BA, Dombroski MA, Chiang P, Cornelius P, Patterson TA, Zeng Y, Santucci S, Tomlinson E, Gibbons CP, Marala R, Brown JA, Kong JX, Lee E, Werner W, Wenzel Z, Giragossian C, Chen H, Coffey SB..  (2010)  Orally active and brain permeable proline amides as highly selective 5HT2c agonists for the treatment of obesity.,  20  (7): [PMID:20202843] [10.1016/j.bmcl.2010.01.107]

2. Banerjee PS, Sharma PK.  (2012)  New antiepileptic agents: structureactivity relationships,  21  (7): [10.1007/s00044-011-9615-3]

Source

Source(1):

• Scientific Literature