[8-Chloro-6-(2,3-dimethoxy-phenyl)-1-isopropyl-4H,6H-2,5-dioxa-3-aza-benzo[e]azulen-4-yl]-acetic acid

ID: ALA1778339

PubChem CID: 24889304

Max Phase: Preclinical

Molecular Formula: C24H24ClNO6

Molecular Weight: 457.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(C2OC(CC(=O)O)c3noc(C(C)C)c3-c3ccc(Cl)cc32)c1OC

Standard InChI:  InChI=1S/C24H24ClNO6/c1-12(2)22-20-14-9-8-13(25)10-16(14)23(15-6-5-7-17(29-3)24(15)30-4)31-18(11-19(27)28)21(20)26-32-22/h5-10,12,18,23H,11H2,1-4H3,(H,27,28)

Standard InChI Key:  WRADIXPKOCXFKO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    2.4568   -0.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4556   -1.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1669   -1.4204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1651    0.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7907   -0.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3694    0.2141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5356    0.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8820   -1.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8768   -0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6833   -0.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1043    0.2435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9969    0.2727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6326    1.0019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4305   -1.3669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5910   -1.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5219   -2.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3189   -2.7589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8803   -2.1034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7854   -2.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0276   -2.4643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8067   -3.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7459    0.2238    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.3259    1.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9099    1.7228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7005    2.5156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9076    2.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3242    2.1479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5366    1.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7018    1.5069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2846    2.0848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2830    3.0939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0751    2.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
  6  7  1  0
  5 14  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 14  2  0
 15  8  1  0
 16 19  1  0
  8  9  1  0
 19 20  1  0
  9  7  1  0
 19 21  1  0
  4  1  1  0
  1 22  1  0
  5 10  1  0
 23 24  2  0
 10 11  1  0
 24 25  1  0
  2  3  1  0
 25 26  2  0
 11 12  1  0
 26 27  1  0
  3  8  2  0
 27 28  2  0
 28 23  1  0
  7 23  1  0
 11 13  2  0
 24 29  1  0
 14 15  1  0
 29 30  1  0
  1  2  2  0
 25 31  1  0
  9  4  2  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1778339

   2-[8-Chloro-6-(2,3-dimethoxyphenyl)-1-propan-2-yl-4,6-dihydro-[2]benzoxepino[4,5-c][1,2]oxazol-4-yl]acetic acid

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: 457.91

Molecular Weight (Monoisotopic): 457.1292

AlogP: 5.77

#Rotatable Bonds: 6

Polar Surface Area: 91.02

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.48

CX Basic pKa: ┄

CX LogP: 4.78

CX LogD: 1.96

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.50

Np Likeness Score: -0.03

References

1. Griebenow N, Buchmueller A, Kolkhof P, Schamberger J, Bischoff H..  (2011)  Identification of 4H,6H-[2]benzoxepino[4,5-c][1,2]oxazoles as novel squalene synthase inhibitors.,  21  (12): [PMID:21576018] [10.1016/j.bmcl.2011.04.092]

2. Griebenow N, Buchmueller A, Kolkhof P, Schamberger J, Bischoff H..  (2011)  Identification of 4H,6H-[2]benzoxepino[4,5-c][1,2]oxazoles as novel squalene synthase inhibitors.,  21  (12): [PMID:21576018] [10.1016/j.bmcl.2011.04.092]

Source

Source(1):

• Scientific Literature