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Linamarin

PubChem CID: 11128

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Compound Synonyms LINAMARIN, 554-35-8, Phaseolunatin, 2-(beta-D-Glucopyranosyloxy)-2-methylpropanenitrile, Manihotoxin, HSDB 3507, UNII-H3V9RP3WLO, H3V9RP3WLO, alpha-Hydroxyisobutyronitrile-beta-D-glucose, 1-cyano-1-methylethyl beta-D-glucoside, BRN 0019237, CHEBI:16441, 2-(beta-D-Glucopyranosyloxy)isobutyronitrile, LINAMARIN [MI], LINAMARIN [HSDB], Propanenitrile, 2-(beta-D-glucopyranosyloxy)-2-methyl-, DTXSID8052857, 5-17-07-00397 (Beilstein Handbook Reference), 2-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropanenitrile, alpha-Hydroxyisobutyronitrile beta-D-glucopyranoside, 2-(b-D-Glucopyranosyloxy)-2-methylpropanenitrile, 9CI, 2-(.BETA.-D-GLUCOPYRANOSYLOXY)-2-METHYLPROPANENITRILE, 2-methyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanenitrile, 2-methyl-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy)propanenitrile, 2-methyl-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxypropanenitrile, Linamarin min. 99%, Spectrum_001946, SpecPlus_000936, Spectrum2_001972, Spectrum3_001622, Spectrum4_001668, Spectrum5_000575, SCHEMBL42021, BSPBio_003283, KBioGR_002195, KBioSS_002500, DivK1c_007032, SPECTRUM1504124, SPBio_002123, CHEMBL3039425, DTXCID5031268, KBio1_001976, KBio2_002492, KBio2_005060, KBio2_007628, KBio3_002503, QLTCHMYAEJEXBT-ZEBDFXRSSA-N, CCG-39428, MFCD00036209, AKOS030242445, ML04551, SDCCGMLS-0066829.P001, 2(betaDGlucopyranosyloxy)isobutyronitrile, NCGC00178164-01, 1ST005033, alpha-Hydroxyisobutyronitrile beta-D-glucose, HY-123114, CS-0081441, NS00094824, 2(betaDGlucopyranosyloxy)2methylpropanenitrile, C01594, G79760, 2-beta-d-glucopyranosyloxy-2-methylpropanenitrile, Propanenitrile, 2(betaDglucopyranosyloxy)2methyl, Q425157, SR-05000002494, 2-(beta-D-Glucopyranosyloxy)-2-methylpropionitrile, SR-05000002494-1, 2-(beta-D-Glucopyranosyloxy)-2-methyl-Propanenitrile, alpha-Hydroxyisobutyronitrile beta-D-glucopyranoside, >=98.0% (HPLC), 2-(?-D-Glucopyranosyloxy)-2-methyl-propanenitrile, Phaseolunatin, a-Hydroxyisobutyronitrile ?-D-glucose, 2-Methyl-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)propanenitrile, 2-methyl-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)propanenitrile
Ghose Rule False
Classyfire Kingdom Organic compounds
Topological Polar Surface Area 123.0
Hydrogen Bond Donor Count 4.0
Pfizer 3 75 Rule True
Scaffold Graph Level C1CCCCC1
Np Classifier Class Cyanogenic glycosides
Deep Smiles OC[C@H]O[C@@H]OCC#N))C)C)))[C@@H][C@H][C@@H]6O))O))O
Heavy Atom Count 17.0
Classyfire Class Organooxygen compounds
Description Occurs in manioc (Manihot utilissimus), flax (Linum usitatissimum), Phaseolus lunatus (butter bean), Trifolium repens (white clover) and other plants. First isol in 1830. Linamarin is found in many foods, some of which are gooseberry, chinese broccoli, cascade huckleberry, and leek.
Scaffold Graph Node Level C1CCOCC1
Classyfire Subclass Carbohydrates and carbohydrate conjugates
Isotope Atom Count 0.0
Molecular Complexity 311.0
Database Name cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem
Defined Atom Stereocenter Count 5.0
Uniprot Id Q9H227, Q9NPD5, Q9Y6L6
Iupac Name 2-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropanenitrile
Prediction Hob 1.0
Class Carbohydrates and carbohydrate conjugates
Veber Rule True
Classyfire Superclass Organic oxygen compounds
Xlogp -1.8
Superclass Organooxygen compounds
Subclass Glycosyl compounds
Gsk 4 400 Rule True
Molecular Formula C10H17NO6
Scaffold Graph Node Bond Level C1CCOCC1
Prediction Swissadme 0.0
Inchi Key QLTCHMYAEJEXBT-ZEBDFXRSSA-N
Silicos It Class Soluble
Fcsp3 0.9
Logs -0.008
Rotatable Bond Count 3.0
State Solid
Logd -1.157
Synonyms 1-Cyano-1-methylethyl b-D-glucoside, 1-Cyano-1-methylethyl beta-D-glucoside, 1-Cyano-1-methylethyl β-D-glucoside, 2-(b-D-Glucopyranosyloxy)-2-methylpropanenitrile, 9CI, 2-(beta-D-Glucopyranosyloxy)-2-methyl-propanenitrile, 2-(beta-D-Glucopyranosyloxy)-2-methylpropanenitrile, alpha-Hydroxyisobutyronitrile-beta-D-glucose, Linamarin, Manihotoxin, Phaseolunatin, Propanenitrile, 2-(beta-D-glucopyranosyloxy)-2-methyl-, 2-(b-D-Glucopyranosyloxy)-2-methylpropanenitrile, 9ci, 2beta-d-glucopyranosyloxy-2-methylpropionitrile(linamarin), 2β-d-glucopyranosyloxy-2-methyl propionitrile (linamarin), linamarin
Substituent Name Cyanogenic glycoside, O-glycosyl compound, Oxane, Monosaccharide, Secondary alcohol, Polyol, 1,2-diol, Oxacycle, Organoheterocyclic compound, Nitrile, Carbonitrile, Ether, Acetal, Hydrocarbon derivative, Primary alcohol, Organonitrogen compound, Alcohol, Aliphatic heteromonocyclic compound
Esol Class Highly soluble
Functional Groups CC#N, CO, CO[C@@H](C)OC
Compound Name Linamarin
Kingdom Organic compounds
Prediction Hob Swissadme 0.0
Exact Mass 247.106
Formal Charge 0.0
Monoisotopic Mass 247.106
Hydrogen Bond Acceptor Count 7.0
Molecular Weight 247.24
Gi Absorption False
Covalent Unit Count 1.0
Total Atom Stereocenter Count 5.0
Total Bond Stereocenter Count 0.0
Molecular Framework Aliphatic heteromonocyclic compounds
Lipinski Rule Of 5 True
Esol 0.2551686
Inchi InChI=1S/C10H17NO6/c1-10(2,4-11)17-9-8(15)7(14)6(13)5(3-12)16-9/h5-9,12-15H,3H2,1-2H3/t5-,6-,7+,8-,9+/m1/s1
Smiles CC(C)(C#N)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
Nring 1.0
Np Classifier Biosynthetic Pathway Amino acids and Peptides
Defined Bond Stereocenter Count 0.0
Egan Rule False
Taxonomy Direct Parent Cyanogenic glycosides
Np Classifier Superclass Amino acid glycosides

  • 1. Outgoing r'ship FOUND_IN to/from Acacia Cambagei (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 2. Outgoing r'ship FOUND_IN to/from Acacia Farnesiana (Plant) Rel Props:Reference:ISBN:9788172363178
  • 3. Outgoing r'ship FOUND_IN to/from Arnica Viscosa (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 4. Outgoing r'ship FOUND_IN to/from Aster Alpinus (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 5. Outgoing r'ship FOUND_IN to/from Athanasia Dregeana (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 6. Outgoing r'ship FOUND_IN to/from Avena Sativa (Plant) Rel Props:Reference:ISBN:9788172362140
  • 7. Outgoing r'ship FOUND_IN to/from Baccharis Solieri (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 8. Outgoing r'ship FOUND_IN to/from Berberis Crataegina (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 9. Outgoing r'ship FOUND_IN to/from Calceolaria Thyrsiflora (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 10. Outgoing r'ship FOUND_IN to/from Calophyllum Thwaitesii (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 11. Outgoing r'ship FOUND_IN to/from Cannabis Sativa (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 12. Outgoing r'ship FOUND_IN to/from Coptis Trifolia (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 13. Outgoing r'ship FOUND_IN to/from Crataegus Pontica (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 14. Outgoing r'ship FOUND_IN to/from Echinocystis Lobata (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 15. Outgoing r'ship FOUND_IN to/from Eriobotrya Japonica (Plant) Rel Props:Source_db:npass_chem_all
  • 16. Outgoing r'ship FOUND_IN to/from Felicia Amelloides (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 17. Outgoing r'ship FOUND_IN to/from Haemanthus Toxicarius (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 18. Outgoing r'ship FOUND_IN to/from Helenium Quadridentatum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 19. Outgoing r'ship FOUND_IN to/from Hevea Brasiliensis (Plant) Rel Props:Reference:ISBN:9788172360481
  • 20. Outgoing r'ship FOUND_IN to/from Leonurus Japonicus (Plant) Rel Props:Reference:https://www.ncbi.nlm.nih.gov/pubmed/18467457
  • 21. Outgoing r'ship FOUND_IN to/from Linum Usitatissimum (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all;npass_chem_all
  • 22. Outgoing r'ship FOUND_IN to/from Lonicera Japonica (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 23. Outgoing r'ship FOUND_IN to/from Manihot Esculenta (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 24. Outgoing r'ship FOUND_IN to/from Melaleuca Decora (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 25. Outgoing r'ship FOUND_IN to/from Osmanthus Fragrans (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 26. Outgoing r'ship FOUND_IN to/from Paramignya Griffithii (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 27. Outgoing r'ship FOUND_IN to/from Pelargonium Graveolens (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 28. Outgoing r'ship FOUND_IN to/from Phaseolus Lunatus (Plant) Rel Props:Source_db:fooddb_chem_all
  • 29. Outgoing r'ship FOUND_IN to/from Phlomoides Medicinalis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 30. Outgoing r'ship FOUND_IN to/from Podocarpus Montanus (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 31. Outgoing r'ship FOUND_IN to/from Pteris Inaequalis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 32. Outgoing r'ship FOUND_IN to/from Schisandra Arisanensis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 33. Outgoing r'ship FOUND_IN to/from Senecio Polyodon (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 34. Outgoing r'ship FOUND_IN to/from Senna Sophera (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 35. Outgoing r'ship FOUND_IN to/from Sophora Japonica (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 36. Outgoing r'ship FOUND_IN to/from Trifolium Repens (Plant) Rel Props:Reference:ISBN:9788185042084
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