2-[(4R,6R)-8-Chloro-6-(3-methoxy-2-methylphenyl)-1-(trifluoromethyl)-4H,6H-[1,2,4]triazolo[4,3-a][4,1]benzoxazepin-4-yl]acetic acid

ID: ALA2441083

PubChem CID: 57778471

Max Phase: Preclinical

Molecular Formula: C21H17ClF3N3O4

Molecular Weight: 467.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc([C@H]2O[C@H](CC(=O)O)c3nnc(C(F)(F)F)n3-c3ccc(Cl)cc32)c1C

Standard InChI:  InChI=1S/C21H17ClF3N3O4/c1-10-12(4-3-5-15(10)31-2)18-13-8-11(22)6-7-14(13)28-19(16(32-18)9-17(29)30)26-27-20(28)21(23,24)25/h3-8,16,18H,9H2,1-2H3,(H,29,30)/t16-,18-/m1/s1

Standard InChI Key:  YNTNSYLRVPNSGY-SJLPKXTDSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    5.6150   -7.7704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6138   -8.5978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3286   -9.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3268   -7.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6922   -7.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4974   -7.4299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8585   -8.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0421   -7.7668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0466   -8.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5078   -6.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1124   -5.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9286   -5.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1393   -4.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5338   -5.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7208   -6.2031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6835   -8.1694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5080   -8.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6954   -9.1090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6242   -9.9403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3929  -10.2650    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9390   -9.6341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0926   -7.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9179  -10.3665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9023   -7.3611    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.5332   -4.5169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3215   -4.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9338  -11.1913    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.1956   -9.9679    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.1997  -10.7745    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.9175   -7.4490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6766   -6.7405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9005   -6.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  9  2  0
  8  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7 17  1  0
  5  8  1  0
  8  9  1  0
 18  9  1  0
  5 10  1  1
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  7 16  1  6
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 17  2  0
 16 22  1  0
 19 23  1  0
  1 24  1  0
 12 25  1  0
 25 26  1  0
 23 27  1  0
 23 28  1  0
 23 29  1  0
 22 30  1  0
 22 31  2  0
 11 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2441083

   CID 57778471

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: 467.83

Molecular Weight (Monoisotopic): 467.0860

AlogP: 4.89

#Rotatable Bonds: 4

Polar Surface Area: 86.47

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.95

CX Basic pKa: ┄

CX LogP: 4.40

CX LogD: 1.21

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.59

Np Likeness Score: -0.60

References

1. Ichikawa M, Ohtsuka M, Ohki H, Ota M, Haginoya N, Itoh M, Shibata Y, Ishigai Y, Terayama K, Kanda A, Sugita K..  (2013)  Discovery of DF-461, a Potent Squalene Synthase Inhibitor.,  4  (10): [PMID:24900587] [10.1021/ml400151c]

Source

Source(1):

• Scientific Literature