(2R,3R,4S)-2-(((1-benzylpiperidin-4-yl)methylamino)methyl)pyrrolidine-3,4-diol

ID: ALA2206829

PubChem CID: 71450639

Max Phase: Preclinical

Molecular Formula: C18H29N3O2

Molecular Weight: 319.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O[C@H]1[C@@H](O)CN[C@@H]1CNCC1CCN(Cc2ccccc2)CC1

Standard InChI:  InChI=1S/C18H29N3O2/c22-17-12-20-16(18(17)23)11-19-10-14-6-8-21(9-7-14)13-15-4-2-1-3-5-15/h1-5,14,16-20,22-23H,6-13H2/t16-,17+,18-/m1/s1

Standard InChI Key:  DRPOVXNOVAPPSV-FGTMMUONSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   24.9738   -0.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7910   -0.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0454    0.4821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3824    0.9575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7237    0.4821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4926   -0.9618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2706   -0.9630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8229    0.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4295    0.1840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.2070    0.4361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8135   -0.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6393   -0.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2419   -1.4615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0210   -1.2139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.1942   -0.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5881    0.1429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6255   -1.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4515   -2.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6741   -2.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4999   -3.6044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1047   -4.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8865   -3.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0570   -3.1059    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 16  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2206829

   (2R,3R,4S)-2-[[(1-benzylpiperidin-4-yl)methylamino]methyl]pyrrolidine-3,4-diol

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: 319.45

Molecular Weight (Monoisotopic): 319.2260

AlogP: 0.18

#Rotatable Bonds: 6

Polar Surface Area: 67.76

Molecular Species: BASE

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.35

CX Basic pKa: 9.74

CX LogP: 0.28

CX LogD: -3.79

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.60

Np Likeness Score: 0.02

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