N-Hexyl-1-deoxynojirimycin

ID: ALA1651550

Chembl Id: CHEMBL1651550

Cas Number: 81117-34-2

PubChem CID: 12766473

Max Phase: Preclinical

Molecular Formula: C12H25NO4

Molecular Weight: 247.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO

Standard InChI:  InChI=1S/C12H25NO4/c1-2-3-4-5-6-13-7-10(15)12(17)11(16)9(13)8-14/h9-12,14-17H,2-8H2,1H3/t9-,10+,11-,12-/m1/s1

Standard InChI Key:  KRNOSIJCJVCXKU-WRWGMCAJSA-N

Alternative Forms

1. Parent:

   

   ALA1651550

   (2R,3R,4R,5S)-1-hexyl-2-(hydroxymethyl)piperidine-3,4,5-triol

2. Alternative Forms:

   

   ALA1651550

   (2R,3R,4R,5S)-1-hexyl-2-(hydroxymethyl)piperidine-3,4,5-triol;hydrochloride

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: 247.33

Molecular Weight (Monoisotopic): 247.1784

AlogP: -0.67

#Rotatable Bonds: 6

Polar Surface Area: 84.16

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.90

CX Basic pKa: 8.37

CX LogP: -0.29

CX LogD: -1.30

Aromatic Rings: ┄

Heavy Atoms: 17

QED Weighted: 0.47

Np Likeness Score: 1.22

References

1. Ghisaidoobe A, Bikker P, de Bruijn AC, Godschalk FD, Rogaar E, Guijt MC, Hagens P, Halma JM, Van't Hart SM, Luitjens SB, van Rixel VH, Wijzenbroek M, Zweegers T, Donker-Koopman WE, Strijland A, Boot R, van der Marel G, Overkleeft HS, Aerts JM, van den Berg RJ..  (2011)  Identification of potent and selective glucosylceramide synthase inhibitors from a library of N-alkylated iminosugars.,  2  (2): [PMID:24900289] [10.1021/ml100192b]

2. Kato A, Nakagome I, Kanekiyo U, Lu TT, Li YX, Yoshimura K, Kishida M, Shinzawa K, Yoshida T, Tanaka N, Jia YM, Nash RJ, Fleet GWJ, Yu CY..  (2022)  5-C-Branched Deoxynojirimycin: Strategy for Designing a 1-Deoxynojirimycin-Based Pharmacological Chaperone with a Nanomolar Affinity for Pompe Disease.,  65  (3.0): [PMID:35072486] [10.1021/acs.jmedchem.1c01673]

Source

Source(1):

• Scientific Literature