2-((3R,5S)-7-chloro-5-(2,3-dimethoxyphenyl)-1-(3-hydroxy-2,2-dimethylpropyl)-2-oxo-1,2,3,5-tetrahydrobenzo[e][1,4]oxazepin-3-yl)acetic acid

ID: ALA1778455

PubChem CID: 11123636

Max Phase: Preclinical

Molecular Formula: C24H28ClNO7

Molecular Weight: 477.94

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc([C@H]2O[C@H](CC(=O)O)C(=O)N(CC(C)(C)CO)c3ccc(Cl)cc32)c1OC

Standard InChI:  InChI=1S/C24H28ClNO7/c1-24(2,13-27)12-26-17-9-8-14(25)10-16(17)21(33-19(23(26)30)11-20(28)29)15-6-5-7-18(31-3)22(15)32-4/h5-10,19,21,27H,11-13H2,1-4H3,(H,28,29)/t19-,21-/m1/s1

Standard InChI Key:  JIGKRELXCKTDLL-TZIWHRDSSA-N

Molfile:  

     RDKit          2D

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    5.8065  -14.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8053  -15.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5170  -15.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5153  -13.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1427  -14.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7213  -13.9155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8867  -13.7739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2328  -15.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2275  -14.3129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0361  -14.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4574  -13.8861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9854  -13.1272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7824  -15.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9422  -15.6981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0950  -13.9059    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.6769  -12.9846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2613  -12.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0518  -11.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2584  -11.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6745  -11.9803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8871  -12.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0538  -12.6218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6371  -12.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6348  -11.0337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4274  -11.2493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3371  -16.1707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7499  -16.5785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8913  -16.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6990  -17.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9863  -16.8513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6542  -15.9758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8404  -18.0062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3506  -13.8568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
 16 17  2  0
  5 13  1  0
 17 18  1  0
 14  8  1  0
 18 19  2  0
  8  9  1  0
 19 20  1  0
  9  7  1  0
 20 21  2  0
 21 16  1  0
  7 16  1  1
  4  1  1  0
 17 22  1  0
  5 10  1  6
 22 23  1  0
 18 24  1  0
 10 11  1  0
 24 25  1  0
  2  3  1  0
 13 26  2  0
 11 12  2  0
 14 27  1  0
 13 14  1  0
 27 28  1  0
  3  8  2  0
 28 29  1  0
  1  2  2  0
 28 30  1  0
  9  4  2  0
 28 31  1  0
  1 15  1  0
 29 32  1  0
  5  6  1  0
 11 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1778455

   (3R,5S)-7-chloro-1,2,3,5-tetrahydro-1-(3-hydroxy-2,2-dimethylpropyl)-5-(2,3-dimethoxyphenyl)-2-oxo-4,1-benzoxazepine-3-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: 477.94

Molecular Weight (Monoisotopic): 477.1554

AlogP: 3.67

#Rotatable Bonds: 8

Polar Surface Area: 105.53

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.98

CX Basic pKa: ┄

CX LogP: 2.99

CX LogD: -0.18

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.60

Np Likeness Score: -0.05

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]

Source

Source(1):

• Scientific Literature