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Showing Compound Zierin (FDB000836)

Record Information
Version1.0
Creation date2010-04-08 22:04:44 UTC
Update date2019-11-26 02:55:29 UTC
Primary IDFDB000836
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameZierin
DescriptionZierin belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. Zierin has been detected, but not quantified in, black elderberries (Sambucus nigra). This could make zierin a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Zierin.
CAS Number645-02-3
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Benzeneacetonitrile, alpha-(beta-D-glucopyranosyloxy)-3-hydroxy-, (S)Kegg
Benzeneacetonitrile, a-(b-D-glucopyranosyloxy)-3-hydroxy-, (S)Generator
Benzeneacetonitrile, α-(β-D-glucopyranosyloxy)-3-hydroxy-, (S)Generator
Zierindb_source
Predicted Properties
PropertyValueSource
logP-1.1ChemAxon
pKa (Strongest Acidic)9.32ChemAxon
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
Polarizability29.37 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC14H17NO7
IUPAC name(2S)-2-(3-hydroxyphenyl)-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile
InChI IdentifierInChI=1S/C14H17NO7/c15-5-9(7-2-1-3-8(17)4-7)21-14-13(20)12(19)11(18)10(6-16)22-14/h1-4,9-14,16-20H,6H2
InChI KeyKCVXNPDAHDGXFD-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(OC(C#N)C2=CC(O)=CC=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-4-unsubstituted benzenoid
  • 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
OntologyNo ontology term
Physico-Chemical Properties
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 156° (softens at 153°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20.3D -29.5DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC08345
Pubchem Compound ID441473
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDDZM56-A:BJQ80-T
EAFUS IDNot Available
Dr. Duke IDZIERIN
BIGG IDNot Available
KNApSAcK IDC00001460
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 / Bioactivities
DescriptorIDDefinitionReference
CyanogenicAn agent that releases hydrogen cyanide, playing a biological role in plant defense. It has therapeutic applications in cancer treatment and key medical uses in chemotherapy, due to its ability to inhibit cell growth and induce apoptosis in cancer cells.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.