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

ID: ALA4061367

Chembl Id: CHEMBL4061367

Cas Number: 2159078-06-3

PubChem CID: 71299592

Max Phase: Preclinical

Molecular Formula: C10H21NO4

Molecular Weight: 219.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCN1C[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1CO

Standard InChI:  InChI=1S/C10H21NO4/c1-2-3-4-11-5-8(13)10(15)9(14)7(11)6-12/h7-10,12-15H,2-6H2,1H3/t7-,8+,9-,10-/m0/s1

Standard InChI Key:  UQRORFVVSGFNRO-JXUBOQSCSA-N

Alternative Forms

1. Parent:

   

   ALA4061367

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

Molecule Features

Natural Product: Yes

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: 219.28

Molecular Weight (Monoisotopic): 219.1471

AlogP: -1.45

#Rotatable Bonds: 4

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: 8.49

CX LogP: -1.18

CX LogD: -2.30

Aromatic Rings: ┄

Heavy Atoms: 15

QED Weighted: 0.46

Np Likeness Score: 1.24

References

1. D'Alonzo D, De Fenza M, Porto C, Iacono R, Huebecker M, Cobucci-Ponzano B, Priestman DA, Platt F, Parenti G, Moracci M, Palumbo G, Guaragna A..  (2017)  N-Butyl-l-deoxynojirimycin (l-NBDNJ): Synthesis of an Allosteric Enhancer of α-Glucosidase Activity for the Treatment of Pompe Disease.,  60  (23): [PMID:29112434] [10.1021/acs.jmedchem.7b00646]

2. De Fenza M, D'Alonzo D, Esposito A, Munari S, Loberto N, Santangelo A, Lampronti I, Tamanini A, Rossi A, Ranucci S, De Fino I, Bragonzi A, Aureli M, Bassi R, Tironi M, Lippi G, Gambari R, Cabrini G, Palumbo G, Dechecchi MC, Guaragna A..  (2019)  Exploring the effect of chirality on the therapeutic potential of N-alkyl-deoxyiminosugars: anti-inflammatory response to Pseudomonas aeruginosa infections for application in CF lung disease.,  175  [PMID:31075609] [10.1016/j.ejmech.2019.04.061]

Source

Source(1):

• Scientific Literature