N-(((6S,7R)-7-(4-Chloro-3-fluorophenyl)-1,4-oxazepan-6-yl)methyl)-3-methoxypropanamide hydrochloride

ID: ALA4762373

PubChem CID: 66976631

Max Phase: Preclinical

Molecular Formula: C16H23Cl2FN2O3

Molecular Weight: 344.81

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COCCC(=O)NC[C@@H]1CNCCO[C@H]1c1ccc(Cl)c(F)c1.Cl

Standard InChI:  InChI=1S/C16H22ClFN2O3.ClH/c1-22-6-4-15(21)20-10-12-9-19-5-7-23-16(12)11-2-3-13(17)14(18)8-11;/h2-3,8,12,16,19H,4-7,9-10H2,1H3,(H,20,21);1H/t12-,16-;/m0./s1

Standard InChI Key:  WKAYSVROGDFFJK-MIRNQTQTSA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
   32.7826  -12.6417    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   30.6635   -9.1092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.4639   -8.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0966   -9.4626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2925   -9.8456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0877  -10.2826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6410  -10.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4405  -10.7838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4713   -9.8332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0753   -9.1155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2548   -9.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8306   -9.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2369  -10.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0561  -10.5343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1189  -11.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4069  -11.9892    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8885  -12.6209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1764  -13.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0822  -12.4879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0135   -9.7925    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.8588   -8.3879    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   30.9827  -13.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2706  -14.2836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.0769  -14.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  4  6  1  0
  5  7  1  0
  6  8  1  0
  7  8  1  0
  5  9  1  6
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  7 15  1  1
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 12 20  1  0
 11 21  1  0
 18 22  1  0
 22 23  1  0
 23 24  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 344.81

Molecular Weight (Monoisotopic): 344.1303

AlogP: 1.91

#Rotatable Bonds: 6

Polar Surface Area: 59.59

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.28

CX LogP: 1.26

CX LogD: -0.60

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.83

Np Likeness Score: -0.89

References

1. Yukawa T,Fujimori I,Kamei T,Nakada Y,Sakauchi N,Yamada M,Ohba Y,Ueno H,Takiguchi M,Kuno M,Kamo I,Nakagawa H,Fujioka Y,Igari T,Ishichi Y,Tsukamoto T.  (2016)  Design, synthesis, and biological evaluation of a novel series of peripheral-selective noradrenaline reuptake inhibitors-Part 2.,  24  (14.0): [PMID:27255177] [10.1016/j.bmc.2016.05.038]

Source

Source(1):

• Scientific Literature