N-Butyl-L-ido-1-deoxynojirimycin

ID: ALA1076754

Chembl Id: CHEMBL1076754

Cas Number: 441061-44-5

PubChem CID: 23622616

Max Phase: Preclinical

Molecular Formula: C10H21NO4

Molecular Weight: 219.28

Molecule Type: Small molecule

Associated Items:

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-AXTSPUMRSA-N

Alternative Forms

  1. Parent:

    ALA1076754

    L-ido Miglustat

Associated Targets(Human)

UGCG Tclin Ceramide glucosyltransferase (308 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SI Tchem Sucrase-isomaltase (84 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MGAM Tclin Maltase-glucoamylase (654 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LCT Tbio Lactase-phlorizin hydrolase (37 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GBA2 Tchem Beta-glucosidase (258 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GAA Tclin Lysosomal alpha-glucosidase (35701 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AGL Tbio Glycogen debranching enzyme (27 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GBA1 Tclin Beta-glucocerebrosidase (14647 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Gaa Lysosomal alpha-glucosidase (58 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Glb1 Beta-galactosidase (29 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Sis Sucrase-isomaltase (30 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ugcg Ceramide glucosyltransferase (150 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 219.28Molecular Weight (Monoisotopic): 219.1471AlogP: -1.45#Rotatable Bonds: 4
Polar Surface Area: 84.16Molecular Species: NEUTRALHBA: 5HBD: 4
#RO5 Violations: 0HBA (Lipinski): 5HBD (Lipinski): 4#RO5 Violations (Lipinski): 0
CX Acidic pKa: 12.90CX Basic pKa: 8.49CX LogP: -1.18CX LogD: -2.30
Aromatic Rings: 0Heavy Atoms: 15QED Weighted: 0.46Np Likeness Score: 1.24

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): [PMID:24900289] [10.1021/ml100192b]
3. 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