Fagomine

HCID 72259CAS 53185-12-9

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Basic information

Standard SMILES: OC[C@H]1NCC[C@@H](O)[C@@H]1O
InChIKey: YZNNBIPIQWYLDM-HSUXUTPPSA-N
Molecular formula: C6H13NO3
Average molar mass: 147.17 g/mol
Monoisotopic mass: 147.08954328

Overview

Fagomine is a member of piperidines.

Names & identifiers

Preferred name: Fagomine
IUPAC: (2R,3R,4R)-2-(hydroxymethyl)piperidine-3,4-diol
English name: fagomine
Molecular formula: C6H13NO3
Molecular weight: 147.17

Names & synonyms

Fagomine53185-12-9D-Fagomine(2r,3r,4r)-2-(hydroxymethyl)piperidine-3,4-diol1,2,5-Trideoxy-1,5-imino-D-arabino-hexitol1M10C1P4SMDTXSID10201243D-arabino-Hexitol, 1,2,5-trideoxy-1,5-imino-RefChem:139877DTXCID101237343,4-Piperidinediol, 2-(hydroxymethyl)-, (2R,3R,4R)-CHEMBL108084

Show more names

Fagomine, >98%dextro-fagomineD-Fagomine53185-12-9Fagomine (D-Fagomine)D-Fagomine (Fagomine)1,2,5-Trideoxy-1,5-epimino-D-xylo-hexitol(2R)-3β,4α-Dihydroxypiperidine-2α-methanol(2R)-2-(Hydroxymethyl)piperidine-3β,4α-diol

(2R,3R,4R)-2-(Hydroxymethyl)-3,4-piperidinediolFAGUNII-1M10C1P4SM(D)-fagomineSureCN142574FAGOMINE, (D)-FAGOMINE, (+)-SCHEMBL142574

Database identifiers

CAS: 53185-12-9
PubChem CID: 72259
DTXSID: DTXSID10201243
ChEMBL: CHEMBL108084
ChEBI: CHEBI:4969
UNII: 1M10C1P4SM
Nikkaji: J265.072J

Properties

Computed structural properties

XLogP: -1.4
Topological polar surface area: 72.7 Å²
Hydrogen bond donors: 4
Hydrogen bond acceptors: 4
Rotatable bonds: 1
Heavy atoms: 10
Formal charge: 0
Complexity: 109

Experimental & physicochemical properties

Melting Point186 - 188 °C

Physical DescriptionSolid

Physicochemical properties

Melting point: 185 · 185-186℃
Boiling point: 315.4 · 315.4±42.0 °C(Predicted)
Density: 1.279 · 1.279
form: Solid
pka: 14.16 · 14.16±0.60(Predicted)
color: White to khaki
LogP: -0.88 · -0.880 (est)
FDA UNII: 1 M10C1P4SM · 1M10C1P4SM

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Applications

DescriptionAn alkaloid of Fagopyrum esculentum, fagomine has been characterized as the crystalline hydrochloride with m.p. 176-7°C. The structure has been shown to be that of a trisubstituted pierpidine.

UsesFagomine is an iminosugar which may reduce the risks of developing insulin resistance and becoming overweight. Also lowers blood glucose and modulates bacterial adhesion.