2-(1-{2-[(4R,6S)-8-Chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl}-1H-pyrazol-4-yl)acetic acid

ID: ALA2057957

PubChem CID: 57779341

Max Phase: Preclinical

Molecular Formula: C27H26ClN3O5

Molecular Weight: 507.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc([C@H]2O[C@H](CCn3cc(CC(=O)O)cn3)c3cccn3-c3ccc(Cl)cc32)c1OC

Standard InChI:  InChI=1S/C27H26ClN3O5/c1-34-24-7-3-5-19(27(24)35-2)26-20-14-18(28)8-9-21(20)31-11-4-6-22(31)23(36-26)10-12-30-16-17(15-29-30)13-25(32)33/h3-9,11,14-16,23,26H,10,12-13H2,1-2H3,(H,32,33)/t23-,26-/m1/s1

Standard InChI Key:  WPAURHCVDBQFQU-ZEQKJWHPSA-N

Molfile:  

     RDKit          2D

 36 40  0  0  0  0  0  0  0  0999 V2000
   -6.2769  -10.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2758  -11.5649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5650  -11.9737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5668  -10.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9541  -11.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3733  -10.3471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2032  -10.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8534  -11.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8585  -10.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3125  -11.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1478  -12.1196    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2165  -12.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4236  -13.3056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8649  -12.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2039   -9.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4948   -8.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4941   -8.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2018   -7.7613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9117   -8.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9089   -8.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7881   -9.3962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7893  -10.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7864   -7.7630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0794   -8.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0659  -11.1019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967  -11.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9803  -10.3376    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7085  -11.8277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1628  -12.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6736  -12.2253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6442  -11.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2096  -11.0903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4444  -12.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4461  -13.5573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6791  -14.0067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2189  -14.0036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5 10  1  0
 17 18  2  0
 11  8  1  0
 18 19  1  0
  8  9  1  0
 19 20  2  0
 20 15  1  0
  7 15  1  1
  9  7  1  0
 16 21  1  0
 10 11  1  0
 21 22  1  0
  4  1  1  0
 17 23  1  0
 23 24  1  0
  2  3  1  0
  5 25  1  6
  3  8  2  0
 25 26  1  0
  1  2  2  0
  1 27  1  0
 11 12  1  0
 26 28  1  0
 28 29  1  0
 12 13  2  0
 13 14  1  0
 14 10  2  0
  9  4  2  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 28  1  0
  5  6  1  0
 30 33  1  0
 15 16  2  0
 33 34  1  0
  6  7  1  0
 16 17  1  0
 34 35  1  0
 34 36  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2057957

   2-(1-{2-[(4R,6S)-8-Chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl}-1H-pyrazol-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: 507.97

Molecular Weight (Monoisotopic): 507.1561

AlogP: 5.22

#Rotatable Bonds: 8

Polar Surface Area: 87.74

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.63

CX Basic pKa: 1.92

CX LogP: 4.40

CX LogD: 1.20

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.35

Np Likeness Score: -0.86

References

1. Ichikawa M, Ohtsuka M, Ohki H, Haginoya N, Itoh M, Sugita K, Usui H, Suzuki M, Terayama K, Kanda A..  (2012)  Discovery of novel tricyclic compounds as squalene synthase inhibitors.,  20  (9): [PMID:22464687] [10.1016/j.bmc.2012.02.054]

Source

Source(1):

• Scientific Literature