(2R,3S,5R)-methyl 3-(N-(fluoromethyl)sulfamoylamino)-2-(((1s,4S)-4-(3-fluorophenyl)cyclohexyloxy)methyl)-5-methylpyrrolidine-1-carboxylate

ID: ALA4740509

PubChem CID: 162644870

Max Phase: Preclinical

Molecular Formula: C21H31F2N3O5S

Molecular Weight: 475.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)N1[C@H](C)C[C@H](NS(=O)(=O)NCF)[C@@H]1CO[C@H]1CC[C@@H](c2cccc(F)c2)CC1

Standard InChI:  InChI=1S/C21H31F2N3O5S/c1-14-10-19(25-32(28,29)24-13-22)20(26(14)21(27)30-2)12-31-18-8-6-15(7-9-18)16-4-3-5-17(23)11-16/h3-5,11,14-15,18-20,24-25H,6-10,12-13H2,1-2H3/t14-,15-,18+,19+,20+/m1/s1

Standard InChI Key:  SIHRJIMCGSWJED-XEGUMIITSA-N

Molfile:  

 
     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   20.8012   -2.5300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2234   -3.1119    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.0163   -3.3214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0372   -5.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0372   -6.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7425   -6.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4478   -6.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4478   -5.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7425   -5.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3310   -6.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6224   -6.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9158   -6.9060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9166   -7.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6298   -8.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3335   -7.7202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1567   -5.2725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8632   -5.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5721   -5.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3166   -5.6083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8652   -5.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4586   -4.2936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6588   -4.4613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0526   -3.9133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6180   -2.5662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7895   -1.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6776   -5.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4853   -6.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8771   -6.9537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2621   -6.6616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0458   -7.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2077   -6.4981    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.5672   -1.5163    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
 12 31  1  0
 25 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4740509

   ---

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: 2.82

#Rotatable Bonds: 8

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: 9.27

CX Basic pKa: ┄

CX LogP: 2.24

CX LogD: 2.24

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.56

Np Likeness Score: -0.58

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