(2S,3R,4R,5S,6S)-2-(hydroxymethyl)-6-propylpiperidine-3,4,5-triol hydrochloride

ID: ALA2409342

PubChem CID: 71747500

Max Phase: Preclinical

Molecular Formula: C9H20ClNO4

Molecular Weight: 205.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC[C@@H]1N[C@@H](CO)[C@@H](O)[C@H](O)[C@H]1O.Cl

Standard InChI:  InChI=1S/C9H19NO4.ClH/c1-2-3-5-7(12)9(14)8(13)6(4-11)10-5;/h5-14H,2-4H2,1H3;1H/t5-,6-,7-,8+,9+;/m0./s1

Standard InChI Key:  AWLAMQZPQLGEBD-RLRVVZGOSA-N

Molfile:  

     RDKit          2D

 15 14  0  0  0  0  0  0  0  0999 V2000
   14.5157   -7.9715    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.3905   -6.6665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6775   -7.0765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6767   -7.9027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3910   -8.3153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1062   -7.9017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1049   -7.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9614   -8.3163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3902   -9.1414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8205   -8.3142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8201   -6.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5344   -7.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2497   -6.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9630   -6.6639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9617   -5.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  2  7  1  0
  4  8  1  6
  5  9  1  1
  6 10  1  6
 11 12  1  0
 12 13  1  0
  7 11  1  1
 14 15  1  0
  3 14  1  6
M  END

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: 205.25

Molecular Weight (Monoisotopic): 205.1314

AlogP: -1.80

#Rotatable Bonds: 3

Polar Surface Area: 92.95

Molecular Species: NEUTRAL

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.86

CX Basic pKa: 8.35

CX LogP: -1.50

CX LogD: -2.50

Aromatic Rings: ┄

Heavy Atoms: 14

QED Weighted: 0.37

Np Likeness Score: 2.16

References

1. Mondon M, Lecornué F, Guillard J, Nakagawa S, Kato A, Blériot Y..  (2013)  Skeletal rearrangement of seven-membered iminosugars: synthesis of (-)-adenophorine, (-)-1-epi-adenophorine and derivatives and evaluation as glycosidase inhibitors.,  21  (16): [PMID:23611766] [10.1016/j.bmc.2013.03.035]

Source

Source(1):

• Scientific Literature