(3R,4S,5R,6R)-6-(2-hydroxyethyl)-5-(hydroxymethyl)piperidine-3,4-diol

ID: ALA3770764

PubChem CID: 127027504

Max Phase: Preclinical

Molecular Formula: C8H17NO4

Molecular Weight: 191.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OCC[C@H]1NC[C@@H](O)[C@@H](O)[C@H]1CO

Standard InChI:  InChI=1S/C8H17NO4/c10-2-1-6-5(4-11)8(13)7(12)3-9-6/h5-13H,1-4H2/t5-,6+,7+,8-/m0/s1

Standard InChI Key:  YGWQBHDZBOWCEC-OSMVPFSASA-N

Molfile:  

     RDKit          2D

 13 13  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383    1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6387   -0.8963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031   -3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039   -3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3064   -4.9494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  3  7  1  1
  2  8  1  1
  1  9  1  1
  9 10  1  0
  6 11  1  1
 11 12  1  0
 12 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3770764

   ---

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: -2.33

#Rotatable Bonds: 3

Polar Surface Area: 92.95

Molecular Species: BASE

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.51

CX Basic pKa: 8.59

CX LogP: -2.83

CX LogD: -4.05

Aromatic Rings: ┄

Heavy Atoms: 13

QED Weighted: 0.34

Np Likeness Score: 2.33

References

1. Thonhofer M, Weber P, Santana AG, Fischer R, Pabst BM, Paschke E, Schalli M, Stütz AE, Tschernutter M, Windischhofer W, Withers SG..  (2016)  Synthesis of C-5a-chain extended derivatives of 4-epi-isofagomine: Powerful β-galactosidase inhibitors and low concentration activators of GM1-gangliosidosis-related human lysosomal β-galactosidase.,  26  (5): [PMID:26838810] [10.1016/j.bmcl.2016.01.059]

Source

Source(1):

• Scientific Literature