N-[5-(Adamantan-1-yl-methoxy)-pentyl]-L-ido-1-deoxynojirimycin

ID: ALA1086996

Chembl Id: CHEMBL1086996

Cas Number: 1203659-60-2

PubChem CID: 11258014

Max Phase: Preclinical

Molecular Formula: C22H39NO5

Molecular Weight: 397.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1[C@@H](O)[C@H](O)[C@@H](O)CN1CCCCCOCC12CC3CC(CC(C3)C1)C2

Standard InChI:  InChI=1S/C22H39NO5/c24-13-18-20(26)21(27)19(25)12-23(18)4-2-1-3-5-28-14-22-9-15-6-16(10-22)8-17(7-15)11-22/h15-21,24-27H,1-14H2/t15?,16?,17?,18-,19-,20+,21+,22?/m0/s1

Standard InChI Key:  XVYLNHVEAOOEGI-CURLCGPBSA-N

Alternative Forms

1. Parent:

   

   ALA1086996

   N-[5-(Adamantan-1-yl-methoxy)-pentyl]-L-ido-1-deoxynojirimycin

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: 397.56

Molecular Weight (Monoisotopic): 397.2828

AlogP: 1.15

#Rotatable Bonds: 9

Polar Surface Area: 93.39

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.90

CX Basic pKa: 8.23

CX LogP: 0.90

CX LogD: 0.01

Aromatic Rings: 0

Heavy Atoms: 28

QED Weighted: 0.44

Np Likeness Score: 0.75

References

1. Wennekes T, Meijer AJ, Groen AK, Boot RG, Groener JE, van Eijk M, Ottenhoff R, Bijl N, Ghauharali K, Song H, O'Shea TJ, Liu H, Yew N, Copeland D, van den Berg RJ, van der Marel GA, Overkleeft HS, Aerts JM..  (2010)  Dual-action lipophilic iminosugar improves glycemic control in obese rodents by reduction of visceral glycosphingolipids and buffering of carbohydrate assimilation.,  53  (2): [PMID:20000679] [10.1021/jm901281m]

2. 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]

3. 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]

4. Ghisaidoobe AT, van den Berg RJ, Butt SS, Strijland A, Donker-Koopman WE, Scheij S, van den Nieuwendijk AM, Koomen GJ, van Loevezijn A, Leemhuis M, Wennekes T, van der Stelt M, van der Marel GA, van Boeckel CA, Aerts JM, Overkleeft HS..  (2014)  Identification and development of biphenyl substituted iminosugars as improved dual glucosylceramide synthase/neutral glucosylceramidase inhibitors.,  57  (21): [PMID:25250725] [10.1021/jm501181z]

Source

Source(1):

• Scientific Literature