(2S,3R,4S)-1-[5-(adamantan-1-yl-methoxy)pentyl]-2-(hydroxymethyl)piperidin-3,4-diol

ID: ALA2011640

Chembl Id: CHEMBL2011640

PubChem CID: 70691536

Max Phase: Preclinical

Molecular Formula: C22H39NO4

Molecular Weight: 381.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1[C@@H](O)[C@@H](O)CCN1CCCCCOCC12CC3CC(CC(C3)C1)C2

Standard InChI:  InChI=1S/C22H39NO4/c24-14-19-21(26)20(25)4-6-23(19)5-2-1-3-7-27-15-22-11-16-8-17(12-22)10-18(9-16)13-22/h16-21,24-26H,1-15H2/t16?,17?,18?,19-,20-,21+,22?/m0/s1

Standard InChI Key:  VIZUYNYAIYKSCL-DGVWQGFFSA-N

Alternative Forms

1. Parent:

   

   ALA2011640

   (2S,3R,4S)-1-[5-(1-adamantylmethoxy)pentyl]-2-(hydroxymethyl)piperidine-3,4-diol

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: 381.56

Molecular Weight (Monoisotopic): 381.2879

AlogP: 2.18

#Rotatable Bonds: 9

Polar Surface Area: 73.16

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.43

CX Basic pKa: 8.66

CX LogP: 1.59

CX LogD: 0.31

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.53

Np Likeness Score: 0.73

References

1. van den Berg RJ, Wennekes T, Ghisaidoobe A, Donker-Koopman WE, Strijland A, Boot RG, van der Marel GA, Aerts JM, Overkleeft HS..  (2011)  Assessment of partially deoxygenated deoxynojirimycin derivatives as glucosylceramide synthase inhibitors.,  2  (7): [PMID:24900342] [10.1021/ml200050s]

Source

Source(1):

• Scientific Literature