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

ID: ALA2409343

PubChem CID: 71747502

Max Phase: Preclinical

Molecular Formula: C8H18ClNO4

Molecular Weight: 191.23

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C8H17NO4.ClH/c1-2-4-6(11)8(13)7(12)5(3-10)9-4;/h4-13H,2-3H2,1H3;1H/t4-,5+,6+,7-,8-;/m1./s1

Standard InChI Key:  WDFAPBKJJDIOFL-AGOZRGOYSA-N

Molfile:  

     RDKit          2D

 14 13  0  0  0  0  0  0  0  0999 V2000
   21.4087  -17.5142    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.4645  -16.5019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1792  -16.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1767  -17.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4595  -18.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7491  -17.7372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7516  -16.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8912  -18.1563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4570  -18.9769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0320  -18.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0370  -16.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3199  -16.9079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8963  -16.5064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8988  -15.6814    0.0000 C   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
  7 11  1  6
 13 14  1  0
  3 13  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: 191.23

Molecular Weight (Monoisotopic): 191.1158

AlogP: -2.19

#Rotatable Bonds: 2

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: 8.32

CX LogP: -1.95

CX LogD: -2.91

Aromatic Rings: ┄

Heavy Atoms: 13

QED Weighted: 0.34

Np Likeness Score: 2.12

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