(2R,3S,4S,6R)-2-(hydroxymethyl)-6-undecylpiperidine-3,4-diol

ID: ALA207359

PubChem CID: 15604793

Max Phase: Preclinical

Molecular Formula: C17H35NO3

Molecular Weight: 301.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCC[C@@H]1C[C@H](O)[C@@H](O)[C@@H](CO)N1

Standard InChI:  InChI=1S/C17H35NO3/c1-2-3-4-5-6-7-8-9-10-11-14-12-16(20)17(21)15(13-19)18-14/h14-21H,2-13H2,1H3/t14-,15-,16+,17+/m1/s1

Standard InChI Key:  CFTMRMOTWVSRCS-NCOADZHNSA-N

Molfile:  

     RDKit          2D

 21 21  0  0  1  0  0  0  0  0999 V2000
    5.0304   -4.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7442   -4.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4581   -4.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1720   -4.1905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8859   -4.6001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5997   -4.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3136   -4.5962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0275   -4.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7413   -4.5923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4552   -4.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1691   -4.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8848   -3.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8848   -4.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5982   -4.5836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3117   -4.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3117   -3.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5982   -2.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0274   -4.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0291   -2.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5982   -2.1026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0264   -5.4154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
 12 13  1  0
  5  6  1  0
  1  2  1  0
  6  7  1  0
  3  4  1  0
  7  8  1  0
 12 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  8  9  1  0
 15 18  1  1
  4  5  1  0
 16 19  1  1
  9 10  1  0
 17 20  1  6
 13 11  1  6
  2  3  1  0
 18 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA207359

   (2R,3S,4S,6R)-2-(hydroxymethyl)-6-undecylpiperidine-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: 301.47

Molecular Weight (Monoisotopic): 301.2617

AlogP: 2.35

#Rotatable Bonds: 11

Polar Surface Area: 72.72

Molecular Species: BASE

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.43

CX Basic pKa: 8.91

CX LogP: 2.74

CX LogD: 1.23

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.44

Np Likeness Score: 1.85

References

1. Pearson MS, Saad RO, Dintinger T, Amri H, Mathé-Allainmat M, Lebreton J..  (2006)  Flexible synthesis and biological evaluation of novel 5-deoxyadenophorine analogues.,  16  (12): [PMID:16603357] [10.1016/j.bmcl.2006.03.035]

Source

Source(1):

• Scientific Literature