N-benzyl-N-((((2R,3R,4S)-3,4-dihydroxypyrrolidin-2-yl)methylamino)methyl)acetamide

ID: ALA2207395

PubChem CID: 71452507

Max Phase: Preclinical

Molecular Formula: C15H23N3O3

Molecular Weight: 293.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N(CNC[C@H]1NC[C@H](O)[C@@H]1O)Cc1ccccc1

Standard InChI:  InChI=1S/C15H23N3O3/c1-11(19)18(9-12-5-3-2-4-6-12)10-16-7-13-15(21)14(20)8-17-13/h2-6,13-17,20-21H,7-10H2,1H3/t13-,14+,15-/m1/s1

Standard InChI Key:  YXRLSAPWCWOKTL-QLFBSQMISA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   10.4501  -11.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2673  -11.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5217  -10.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8587  -10.1117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2000  -10.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9689  -12.0310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7469  -12.0322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2992  -10.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9057  -10.8900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6833  -10.6386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2898  -11.1862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0674  -10.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1188  -11.9853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7253  -12.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6739  -11.4824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2384  -10.1357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5526  -13.3300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1583  -13.8774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9368  -13.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1062  -12.8223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4991  -12.2784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  1  6  1  1
  2  7  1  1
  3  8  1  6
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 12 15  2  0
 12 16  1  0
 14 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2207395

   N-benzyl-N-[[[(2R,3R,4S)-3,4-dihydroxypyrrolidin-2-yl]methylamino]methyl]acetamide

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: 293.37

Molecular Weight (Monoisotopic): 293.1739

AlogP: -0.72

#Rotatable Bonds: 6

Polar Surface Area: 84.83

Molecular Species: BASE

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.35

CX Basic pKa: 8.83

CX LogP: -0.85

CX LogD: -2.29

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.52

Np Likeness Score: 0.19

References

1. Moorthy NS, Brás NF, Ramos MJ, Fernandes PA..  (2012)  Virtual screening and QSAR study of some pyrrolidine derivatives as α-mannosidase inhibitors for binding feature analysis.,  20  (24): [PMID:23151473] [10.1016/j.bmc.2012.10.011]

Source

Source(1):

• Scientific Literature