methyl (2R,3S,5R)-2-[[(1S,3R,4R)-3,4-dideuterio-4-(3-fluorophenyl)cyclohexoxy]methyl]-3-(dimethylsulfamoylamino)-5-methyl-pyrrolidine-1-carboxylate

ID: ALA4790356

PubChem CID: 154622581

Max Phase: Preclinical

Molecular Formula: C22H34FN3O5S

Molecular Weight: 471.60

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  [2H][C@@H]1C[C@@H](OC[C@H]2[C@@H](NS(=O)(=O)N(C)C)C[C@@H](C)N2C(=O)OC)CC[C@@]1([2H])c1cccc(F)c1

Standard InChI:  InChI=1S/C22H34FN3O5S/c1-15-12-20(24-32(28,29)25(2)3)21(26(15)22(27)30-4)14-31-19-10-8-16(9-11-19)17-6-5-7-18(23)13-17/h5-7,13,15-16,19-21,24H,8-12,14H2,1-4H3/t15-,16-,19+,20+,21+/m1/s1/i8D,16D/t8-,15-,16+,19-,20+,21+

Standard InChI Key:  VRCBPPQSWQSLSW-QQQLQBHZSA-N

Molfile:  

 
     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
   21.2098  -15.2130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6320  -15.7949    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.4249  -16.0043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4458  -18.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4458  -19.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1511  -19.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8564  -19.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8564  -18.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1511  -17.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7396  -19.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0310  -19.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3244  -19.5890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3252  -20.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0384  -20.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7421  -20.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5653  -17.9555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2718  -18.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9807  -17.9597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7252  -18.2912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2737  -17.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8672  -16.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0674  -17.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4612  -16.5962    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0266  -15.2492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1981  -14.4502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0862  -17.7733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8938  -19.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2857  -19.6367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6707  -19.3445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4544  -20.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6163  -19.1811    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.2491  -15.5007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7359  -18.7706    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.7369  -17.9555    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  4  9  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  5 10  1  1
  8 16  1  1
 16 17  1  0
 18 17  1  1
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 22 23  1  1
 23  2  1  0
  2 24  1  0
 24 25  1  0
 20 26  1  1
 19 27  1  0
 27 28  1  0
 27 29  2  0
 28 30  1  0
 12 31  1  0
 24 32  1  0
  5 33  1  0
  4 34  1  6
M  ISO  2  33   2  34   2
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: 471.60

Molecular Weight (Monoisotopic): 471.2203

AlogP: 2.86

#Rotatable Bonds: 7

Polar Surface Area: 88.18

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.41

CX Basic pKa: 0.03

CX LogP: 2.28

CX LogD: 2.28

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.66

Np Likeness Score: -0.61

References

1. Sabnis RW..  (2020)  Novel 5-Alkyl Pyrrolidine Orexin Receptor Agonists for Treating Sleep Disorders.,  11  (11): [PMID:33214817] [10.1021/acsmedchemlett.0c00501]

Source

Source(1):

• Scientific Literature