(2R,3S,5R)-methyl 2-(((1s,4S)-4-(2,5-difluorophenyl)cyclohexyloxy)methyl)-5-methyl-3-(N-methylsulfamoylamino)pyrrolidine-1-carboxylate

ID: ALA4799832

PubChem CID: 162676844

Max Phase: Preclinical

Molecular Formula: C21H31F2N3O5S

Molecular Weight: 475.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNS(=O)(=O)N[C@H]1C[C@@H](C)N(C(=O)OC)[C@H]1CO[C@H]1CC[C@@H](c2cc(F)ccc2F)CC1

Standard InChI:  InChI=1S/C21H31F2N3O5S/c1-13-10-19(25-32(28,29)24-2)20(26(13)21(27)30-3)12-31-16-7-4-14(5-8-16)17-11-15(22)6-9-18(17)23/h6,9,11,13-14,16,19-20,24-25H,4-5,7-8,10,12H2,1-3H3/t13-,14-,16+,19+,20+/m1/s1

Standard InChI Key:  PGWXJDASJLKIBW-RXUQYVRZSA-N

Molfile:  

 
     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    9.4802   -9.7361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9024  -10.3181    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.6953  -10.5275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7162  -12.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7162  -13.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4215  -14.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1268  -13.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1268  -12.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4215  -12.4725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0100  -14.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3015  -13.7032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5948  -14.1122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5956  -14.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3088  -15.3376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0126  -14.9263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8357  -12.4787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5422  -12.8894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2511  -12.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9956  -12.8144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5442  -12.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1376  -11.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3378  -11.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7317  -11.1194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2970   -9.7724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4685   -8.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3566  -12.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1643  -13.6140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5561  -14.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9411  -13.8677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7248  -14.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3011  -12.8860    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.3129  -16.1548    0.0000 F   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
 11 31  1  0
 14 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4799832

   ---

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: 475.56

Molecular Weight (Monoisotopic): 475.1952

AlogP: 2.66

#Rotatable Bonds: 7

Polar Surface Area: 96.97

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.38

CX Basic pKa: 0.35

CX LogP: 2.20

CX LogD: 2.20

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.63

Np Likeness Score: -0.67

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