2-{[(1-Benzyl-piperidin-4-ylmethyl)-amino]-methyl}-pyrrolidine-3,4-diol

ID: ALA84272

PubChem CID: 44462072

Max Phase: Preclinical

Molecular Formula: C18H29N3O2

Molecular Weight: 319.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC1CNC(CNCC2CCN(Cc3ccccc3)CC2)C1O

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

Standard InChI Key:  DRPOVXNOVAPPSV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    4.7792   -3.1792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5917   -4.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4000   -3.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1542   -7.0875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -4.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2125   -3.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167   -7.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2250   -4.4167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8792   -6.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9625   -7.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5875   -2.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0875   -2.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4000   -4.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7917   -7.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5000   -6.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4167   -5.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2292   -5.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6375   -5.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -6.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2667   -8.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4542   -8.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7250   -6.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1875   -7.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  1  0
  4  9  1  0
  5  6  1  0
  6  1  1  0
  7  4  1  0
  8 13  1  0
  9 16  1  0
 10 15  1  0
 11  2  1  0
 12  5  1  0
 13  3  1  0
 14  7  1  0
 15 17  1  0
 16 17  1  0
 17 18  1  0
 18  8  1  0
 19 14  2  0
 20 14  1  0
 21 20  2  0
 22 19  1  0
 23 21  1  0
  2  5  1  0
 10  4  1  0
 22 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA84272

   2-{[(1-Benzyl-piperidin-4-ylmethyl)-amino]-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. Popowycz F, Gerber-Lemaire S, Demange R, Rodriguez-García E, Asenjo AT, Robina I, Vogel P..  (2001)  Derivatives of (2R,3R,4S)-2-aminomethylpyrrolidine-3,4-diol are selective alpha-mannosidase inhibitors.,  11  (18): [PMID:11549453] [10.1016/s0960-894x(01)00477-2]

Source

Source(1):

• Scientific Literature