2(R)-Hydroxy-2-methylbutyronitrile-beta-D-glucopyranoside
PubChem CID: 4626626
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| Compound Synonyms | 2(R)-Hydroxy-2-methylbutyronitrile-beta-D-glucopyranoside, 2-(beta-D-Glucopyranosyloxy)-2-methyl-(R)-Butanenitrile, AKOS030242404 |
|---|---|
| Topological Polar Surface Area | 123.0 |
| Hydrogen Bond Donor Count | 4.0 |
| Heavy Atom Count | 18.0 |
| Description | Glycoside from Trifolium repens (white clover) and other plants Lotaustralin is a cyanogenic glucoside found in small amounts in name giving Fabaceae Lotus australis, cassava (Manihot esculenta), lima bean (Phaseolus lunatus), roseroot (Rhodiola rosea) and white clover (Trifolium repens), among other plants. Lotaustralin is structurally related to linamarin, another glucoside found in these plants, and differs from it only by the presence of an extra methyl group. Both lotaustralin and linamarin may be hydrolysed by the enzyme linamarase to form glucose and a precursor to the toxic compound hydrogen cyanide. |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 329.0 |
| Database Name | fooddb_chem_all;hmdb_chem_all;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Uniprot Id | Q9H227 |
| Iupac Name | 2-methyl-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutanenitrile |
| Nih Violation | False |
| Class | Organooxygen compounds |
| Xlogp | -1.1 |
| Superclass | Organic oxygen compounds |
| Is Pains | False |
| Subclass | Carbohydrates and carbohydrate conjugates |
| Molecular Formula | C11H19NO6 |
| Inchi Key | WEWBWVMTOYUPHH-UHFFFAOYSA-N |
| Rotatable Bond Count | 4.0 |
| State | Solid |
| Synonyms | 2(R)-Hydroxy-2-methylbutyronitrile-beta-D-glucopyranoside, Butanenitrile, 2-(beta-D-glucopyranosyloxy)-2-methyl-, (R)-, Lotaustralin, 2-(beta-D-Glucopyranosyloxy)-2-methyl-(R)-butanenitrile, 2(R)-Hydroxy-2-methylbutyronitrile-beta-D- glucopyranoside, Lotaustralin, (S)-isomer |
| Compound Name | 2(R)-Hydroxy-2-methylbutyronitrile-beta-D-glucopyranoside |
| Kingdom | Organic compounds |
| Exact Mass | 261.121 |
| Formal Charge | 0.0 |
| Brenk Violation | False |
| Monoisotopic Mass | 261.121 |
| Hydrogen Bond Acceptor Count | 7.0 |
| Molecular Weight | 261.269 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 6.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aliphatic heteromonocyclic compounds |
| Inchi | InChI=1S/C11H19NO6/c1-3-11(2,5-12)18-10-9(16)8(15)7(14)6(4-13)17-10/h6-10,13-16H,3-4H2,1-2H3 |
| Smiles | CCC(C)(C#N)OC1C(C(C(C(O1)CO)O)O)O |
| Defined Bond Stereocenter Count | 0.0 |
| Taxonomy Direct Parent | Cyanogenic glycosides |
- 1. Outgoing r'ship
FOUND_INto/from Linum Usitatissimum (Plant) Rel Props:Source_db:fooddb_chem_all