Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120484
Identification
Name: taxiphyllin
Description:A β-D-glucoside consisting of (R)-prunasin carrying a hydroxy substituent at position 4 on the phenyl ring.
Structure
Thumb
Synonyms:
  • (R)-4-Hydroxymandelonitrile beta-D-glucoside
  • (R)-alpha-(β-D-glucopyranosyloxy)-4-hydroxybenzeneacetonitrile
  • (R)-p-hydroxymandelonitrile-D-glucopyranoside
  • Taxiphyllin
Chemical Formula: C14H17NO7
Average Molecular Weight: 311.291
Monoisotopic Molecular Weight: 311.1005
InChI Key: NVLTYOJHPBMILU-GMDXDWKASA-N
InChI:InChI=1S/C14H17NO7/c15-5-9(7-1-3-8(17)4-2-7)21-14-13(20)12(19)11(18)10(6-16)22-14/h1-4,9-14,16-20H,6H2/t9-,10+,11+,12-,13+,14+/m0/s1
CAS number: 21401-21-8
IUPAC Name:(2R)-(β-D-glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile
Traditional IUPAC Name: dhurrin
SMILES:C(C(C1(C=CC(=CC=1)O))OC2(OC(C(C(C2O)O)O)CO))#N
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic oxygen compounds
Sub ClassOrganooxygen compounds
Direct Parent Cyanogenic glycosides
Alternative Parents
Substituents
  • Cyanogenic glycoside
  • Hexose monosaccharide
  • O-glycosyl compound
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Secondary alcohol
  • Polyol
  • Oxacycle
  • Nitrile
  • Carbonitrile
  • Acetal
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organopnictogen compound
  • Organic nitrogen compound
  • Primary alcohol
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:0
Melting point: 176 °C
Experimental Properties:
PropertyValueReference
Melting Point176 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility28.4 mg/mLALOGPS
logP-0.77ALOGPS
logP-1.1ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)9.46ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area143.4 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.08 m3·mol-1ChemAxon
Polarizability30.2 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w29-0922000000-4323039c23c09ae7d5b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0900000000-20291a7cc72858475773View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ff0-2900000000-d9b8829840517b5ef00aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-1927000000-2051e5cb0bd7423a8dadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-2910000000-abc72215556e260df8c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-8900000000-11bb86435bb0e9209de4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w29-0922000000-4323039c23c09ae7d5b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0900000000-20291a7cc72858475773View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ff0-2900000000-d9b8829840517b5ef00aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-1927000000-2051e5cb0bd7423a8dadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-2910000000-abc72215556e260df8c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-8900000000-11bb86435bb0e9209de4View in MoNA
References
References:
  • Petruccioli M, Brimer L, Cicalini AR, Pulci V, Federici F (1999)Production and properties of the linamarase and amygdalase activities of Penicillium aurantiogriseum P35. Bioscience, biotechnology, and biochemistry 63, Pubmed: 10380623
  • Calderón AI, Terreaux C, Gupta MP, Hostettmann K, Schenk KJ (2003)Taxiphyllin from Henriettella fascicularis. Acta crystallographica. Section C, Crystal structure communications 59, Pubmed: 12711800
  • Rosen MA, Farnden KJ, Conn EE (1975)Stereochemical aspects of the biosynthesis of the epimeric cyanogenic glucosides dhurrin and taxiphyllin. The Journal of biological chemistry 250, Pubmed: 1194256
  • Nahrstedt A, Kant JD, Hösel W (1984)Aspects on the Biosynthesis of the Cyanogenic Glucoside Triglochinin in Triglochin maritima1. Planta medica 50, Pubmed: 17340339
  • Cutler AJ, Hösel W, Sternberg M, Conn EE (1981)The in vitro biosynthesis of taxiphyllin and the channeling of intermediates in Triglochin maritima. The Journal of biological chemistry 256, Pubmed: 7012151
  • Oueslati MH, Ben Jannet H, Mighri Z, Chriaa J, Abreu PM (2006)Phytochemical constituents from Salsola tetrandra. Journal of natural products 69, Pubmed: 16989538
  • Hösel W, Nahrstedt A (1980)In vitro biosynthesis of the cyanogenic glucoside taxiphyllin in Triglochin maritima. Archives of biochemistry and biophysics 203, Pubmed: 7458352
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
HMDBHMDB30704
CHEMSPIDER96890
PUBCHEM107721
CHEBI16267
LIGAND-CPDC01855
CAS21401-21-8