Miglustat (CED0006411)

Record Information

Version

1.0

Creation Date

2016-05-22 05:15:26 UTC

Update Date

2026-08-18 03:10:27 UTC

Accession Number

CHEM018440

Identification

Common Name

Miglustat

Class

Small Molecule

Description

Miglustat belongs to the piperidines, a class of organoheterocyclic compounds within the organic compounds. This compound has the chemical formula $\text{C}_{10}\text{H}_{21}\text{NO}_4$ and an average molecular weight of 219.28 g/mol. In terms of biological activity, miglustat acts as an inhibitor of the protein target ceramide glucosyltransferase (UGCG). The compound is found in or released from three recorded sources: household cleaning and consumer products (non electric simulated smoking devices), electrical and electronic equipment (electrically stimulated smoking devices), and healthcare, pharmaceuticals and veterinary products (alimentary tract and metabolism products). The recorded route of exposure for this substance is oral.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
BuDNJ	ChEBI
Butyldeoxynojirimycin	ChEBI
Miglustatum	ChEBI
N-(N-Butyl)deoxynojirimycin	ChEBI
N-Butyl deoxynojirimycin	ChEBI
N-Butyl-1-deoxynojirimycin	ChEBI
N-Butylmoranoline	ChEBI
NB-DNJ	ChEBI
SC-48334	ChEBI
Zavesca	ChEBI
Brazaves	Kegg
N-(N-Butyl)deoxy-nojirimycin	HMDB
N-Butyldeoxynojirimycin	HMDB
OGT 918	HMDB

Chemical Formula

C₁₀H₂₁NO₄

Average Molecular Mass

219.278 g/mol

Monoisotopic Mass

219.147 g/mol

CAS Registry Number

72599-27-0

IUPAC Name

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

Traditional Name

miglustat

SMILES

CCCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO

InChI Identifier

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-/m1/s1

InChI Key

UQRORFVVSGFNRO-UTINFBMNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Not Available

Direct Parent

Piperidines

Alternative Parents

Substituents

Piperidine
1,2-aminoalcohol
Secondary alcohol
Tertiary aliphatic amine
Tertiary amine
Polyol
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Primary alcohol
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:50381 )
tertiary amino compound (CHEBI:50381 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	331 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-1.2	ChemAxon
logS	0.18	ALOGPS
pKa (Strongest Acidic)	12.9	ChemAxon
pKa (Strongest Basic)	8.49	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	84.16 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	55.74 m³·mol⁻¹	ChemAxon
Polarizability	23.99 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0zos-3910000000-487652a19fde10ffe683	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-00kf-2142900000-0c0744b80c14d6b20646	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0fk9-0190000000-1545727fb8c9dc1b2685	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ue9-6980000000-589edd008686a4fe9d4b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-9800000000-0ef03d48da73c35c0c96	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014r-0690000000-52d21087091279bec38b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0fe0-3930000000-e5cf8de6350860e73852	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00dl-9100000000-f8691ad25d535e38c625	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0090000000-32e6ad4c1e36e0f2fb66	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0290000000-b7fd37a3d8a9c58a1be0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4l-9310000000-fb18a3f257a799c2f63d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0090000000-66c377bd2995bc818438	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-2590000000-6286d923af7492795fcf	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05gi-9000000000-ba860e30faee784f9ef1	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2653.0	Log mg/kg	[1500:4700]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
272	Alimentary tract and metabolism products	Healthcare, pharmaceuticals & veterinary products	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available

Pathways

2 pathways

Miglustat Drug Metabolism

Miglustat Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Non-lysosomal glucosylceramidase	Q69ZF3	Mus musculus	Predicted (SEA)	0.0778492
Click to view 3D structure	Non-lysosomal glucosylceramidase	Q9HCG7	Humans	Predicted (SEA)	0.155698
Click to view 3D structure	Sucrase-isomaltase	B5THE3	Mus musculus	Predicted (SEA)	0.155698
Click to view 3D structure	Lysosomal alpha-glucosidase	P70699	Mus musculus	Predicted (SEA)	0.155698
Click to view 3D structure	Lysosomal alpha-glucosidase	P10253	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Maltase-glucoamylase	O43451	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Ceramide glucosyltransferase	O88693	Mus musculus	Predicted (SEA)	0.155698
Click to view 3D structure	Sucrase-isomaltase, intestinal	P23739	Rattus norvegicus	Predicted (SEA)	0.0778492
Click to view 3D structure	Lysosomal acid glucosylceramidase	P04062	Humans	Predicted (SEA)	0.233548
Click to view 3D structure	Sucrase-isomaltase, intestinal	P14410	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Ceramide glucosyltransferase	Q16739	Humans	Predicted (SEA)	0.233548
Click to view 3D structure	Glycogen debranching enzyme	P35573	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Alpha-glucosidase	Q9LGC6	Oryza sativa Japonica Group	Predicted (SEA)	0.155698
Click to view 3D structure	Lysosomal alpha-glucosidase	Q6P7A9	Rattus norvegicus	Predicted (SEA)	0.622794
Click to view 3D structure	Lactase/phlorizin hydrolase	P09848	Humans	Predicted (SEA)	0.467095
Click to view 3D structure	Beta-galactosidase	Q59750	Sinorhizobium meliloti	Predicted (SEA)	0.544945
Click to view 3D structure	Alpha-galactosidase	Q42656	Coffea arabica	Predicted (SEA)	1.71268
Click to view 3D structure	Beta-galactosidase	P16278	Humans	Predicted (SEA)	2.64687
Click to view 3D structure	Beta-galactosidase	P00722	Escherichia coli (strain K12)	Predicted (SEA)	0.389246
Click to view 3D structure	Beta-glucosidase	P27034	Agrobacterium tumefaciens	Predicted (SEA)	0.622794
Click to view 3D structure	Glycogen debranching enzyme	P35574	Oryctolagus cuniculus	Predicted (SEA)	0.700643
Click to view 3D structure	IAG-nucleoside hydrolase	Q9GPQ4	Trypanosoma vivax	Predicted (SEA)	0.544945
Click to view 3D structure	Lactase/phlorizin hydrolase	Q02401	Rattus norvegicus	Predicted (SEA)	1.24559
Click to view 3D structure	Beta-galactosidase	Q58D55	Bos taurus	Predicted (SEA)	2.33548
Click to view 3D structure	Putative beta-hexosaminidase	Q9RK76	Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)	Predicted (SEA)	2.95827