Record Information
Version1.0
Creation date2010-04-08 22:10:48 UTC
Update date2019-11-26 03:08:39 UTC
Primary IDFDB013582
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSambunigrin
DescriptionSambunigrin, also known as L-prunasin or (2S)-sambunigrin, belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. Sambunigrin is an extremely weak basic (essentially neutral) compound (based on its pKa). Sambunigrin is found, on average, in the highest concentration within black elderberries. Sambunigrin has also been detected, but not quantified in, fruits and passion fruits. This could make sambunigrin a potential biomarker for the consumption of these foods. Sambunigrin is a potentially toxic compound.
CAS Number99-19-4
Structure
Thumb
Synonyms
SynonymSource
(S)-Mandelonitrile beta-D-glucosideChEBI
L-PrunasinChEBI
(S)-Mandelonitrile b-D-glucosideGenerator
(S)-Mandelonitrile β-D-glucosideGenerator
(2S)-(beta-D-Glucopyranosyloxy)(phenyl)acetonitrileHMDB
(2S)-SambunigrinHMDB
(S)-PrunasinHMDB
SambunigrinMeSH
Predicted Properties
PropertyValueSource
Water Solubility28.2 g/LALOGPS
logP-0.56ALOGPS
logP-0.82ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area123.17 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity70.1 m³·mol⁻¹ChemAxon
Polarizability29.09 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC14H17NO6
IUPAC name(2S)-2-phenyl-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile
InChI IdentifierInChI=1S/C14H17NO6/c15-6-9(8-4-2-1-3-5-8)20-14-13(19)12(18)11(17)10(7-16)21-14/h1-5,9-14,16-19H,7H2/t9-,10-,11-,12+,13-,14-/m1/s1
InChI KeyZKSZEJFBGODIJW-YOVYLDAJSA-N
Isomeric SMILESOC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O
Average Molecular Weight295.2879
Monoisotopic Molecular Weight295.105587281
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
  • Monocyclic benzene moiety
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Secondary alcohol
  • Polyol
  • Nitrile
  • Carbonitrile
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Primary alcohol
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 56.95%; H 5.80%; N 4.74%; O 32.51%DFC
Melting PointMp 151-152°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -76.3 (EtOAc)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSSambunigrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-02e9-5970000000-af7eea9783215b5077ecSpectrum
Predicted GC-MSSambunigrin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-2411490000-eb6d4c8c77d360144d24Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0950000000-94af28ff3325aa91829fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-0900000000-c209318aed53a776a604Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067i-3900000000-f46229fde33733da738aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-1890000000-a1a34454361f8a461a19Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2910000000-9efa8331da9f7f35adb0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-9800000000-6551bbcd67cdb9809506Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC04273
Pubchem Compound ID91434
Pubchem Substance IDNot Available
ChEBI ID27761
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34981
CRC / DFC (Dictionary of Food Compounds) IDJDX91-A:JFL71-A
EAFUS IDNot Available
Dr. Duke IDSAMBUNIGRIN|S-SAMBUNIGRIN
BIGG IDNot Available
KNApSAcK IDC00034206
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
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
cyanogenicDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).