Record Information
Version1.0
Creation date2010-04-08 22:05:27 UTC
Update date2020-02-24 19:10:34 UTC
Primary IDFDB002625
Secondary Accession Numbers
  • FDB002626
Chemical Information
FooDB NameTaxiphyllin
DescriptionTaxiphyllin belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. Taxiphyllin has been detected, but not quantified in, several different foods, such as red rice (Oryza rufipogon), soy beans (Glycine max), yellow wax beans (Phaseolus vulgaris), common thymes (Thymus vulgaris), and wasabis (Wasabia japonica). This could make taxiphyllin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Taxiphyllin.
CAS Number21401-21-8
Structure
Thumb
Synonyms
SynonymSource
(R)-4-Hydroxymandelonitrile beta-D-glucosideHMDB
(R)-P-Hydroxymandelonitrile-D-glucopyranosideHMDB
Phyllanthin?HMDB
Phyllanthoside?HMDB
(R)-4-hydroxymandelonitrile beta-D-glucosidebiospider
(r)-p-hydroxymandelonitrile-d-glucopyranosidebiospider
Taxiphyllindb_source
Predicted Properties
PropertyValueSource
Water Solubility28.4 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.08 m³·mol⁻¹ChemAxon
Polarizability30.2 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC14H17NO7
IUPAC name2-(4-hydroxyphenyl)-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile
InChI IdentifierInChI=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
InChI KeyNVLTYOJHPBMILU-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(OC(C#N)C2=CC=C(O)C=C2)C(O)C(O)C1O
Average Molecular Weight311.2873
Monoisotopic Molecular Weight311.100501903
Classification
Description Belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentCyanogenic 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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 54.02%; H 5.50%; N 4.50%; O 35.98%DFC
Melting PointMp 176°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -66.7 (c, 0.37 in EtOH)DFC
Spectroscopic UV Data277 (e 21880) (MeOH) (Derep)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSTaxiphyllin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001l-6980000000-f80d5117e719acd7ea21Spectrum
Predicted GC-MSTaxiphyllin, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-2120139000-64b3d92eecffc4b7a926Spectrum
Predicted GC-MSTaxiphyllin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w29-0922000000-4323039c23c09ae7d5b62015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0900000000-20291a7cc728584757732015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ff0-2900000000-d9b8829840517b5ef00a2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-1927000000-2051e5cb0bd7423a8dad2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-2910000000-abc72215556e260df8c02015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-8900000000-11bb86435bb0e9209de42015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w29-0922000000-4323039c23c09ae7d5b62015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0900000000-20291a7cc728584757732015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ff0-2900000000-d9b8829840517b5ef00a2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-1927000000-2051e5cb0bd7423a8dad2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-2910000000-abc72215556e260df8c02015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-8900000000-11bb86435bb0e9209de42015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0904000000-baae4b1f1ed72ce9ee842021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-2410a7a9ec6f40f45a162021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001j-2900000000-d3b6c4b5bde5be1cac822021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0916000000-37b4ac284188fd96ab152021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0911000000-2e031aa32e65d2a7b3bb2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067i-2900000000-8756a0c265050c89a1362021-09-23View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC01855
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI ID16267
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDDZM59-D:CMS65-I
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference