(2S,3R,4S,5R)-3-Hydroxymethyl-2-pentylpiperidine-4,5-diol; (5aS)-5a-C-pentyl-4-epi-isofagomine

ID: ALA4099495

PubChem CID: 137661178

Max Phase: Preclinical

Molecular Formula: C11H23NO3

Molecular Weight: 217.31

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C11H23NO3/c1-2-3-4-5-9-8(7-13)11(15)10(14)6-12-9/h8-15H,2-7H2,1H3/t8-,9-,10+,11-/m0/s1

Standard InChI Key:  HEXGKPRMUKYMCW-MMWGEVLESA-N

Molfile:  

     RDKit          2D

 15 15  0  0  0  0  0  0  0  0999 V2000
   11.0919   -3.9834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0919   -4.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8039   -5.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5159   -4.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5159   -3.9834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8039   -3.5667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2298   -5.2219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8039   -6.0418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3780   -5.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6629   -4.8105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3762   -3.5730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6629   -3.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9472   -3.5772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2340   -3.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5183   -3.5814    0.0000 C   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
  4  7  1  1
  3  8  1  1
  2  9  1  1
  9 10  1  0
  1 11  1  6
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4099495

   ---

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: 217.31

Molecular Weight (Monoisotopic): 217.1678

AlogP: -0.13

#Rotatable Bonds: 5

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: 13.51

CX Basic pKa: 9.08

CX LogP: 0.01

CX LogD: -1.67

Aromatic Rings: ┄

Heavy Atoms: 15

QED Weighted: 0.48

Np Likeness Score: 2.09

References

1. Front S, Biela-Banaś A, Burda P, Ballhausen D, Higaki K, Caciotti A, Morrone A, Charollais-Thoenig J, Gallienne E, Demotz S, Martin OR..  (2017)  (5aR)-5a-C-Pentyl-4-epi-isofagomine: A powerful inhibitor of lysosomal β-galactosidase and a remarkable chaperone for mutations associated with GM1-gangliosidosis and Morquio disease type B.,  126  [PMID:27750150] [10.1016/j.ejmech.2016.09.095]

Source

Source(1):

• Scientific Literature