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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:55:00 UTC
Update Date2022-03-07 02:54:18 UTC
HMDB IDHMDB0034981
Secondary Accession Numbers
  • HMDB34981
Metabolite Identification
Common NameSambunigrin
DescriptionSambunigrin, also known as (2S)-sambunigrin or L-prunasin, 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 found, on average, in the highest concentration within black elderberries (Sambucus nigra). Sambunigrin has also been detected, but not quantified in, fruits and passion fruits (Passiflora edulis). This could make sambunigrin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Sambunigrin.
Structure
Thumb
Synonyms
ValueSource
(2S)-SambunigrinChEBI
(S)-(beta-D-Glucopyranosyloxy)(phenyl)acetonitrileChEBI
(S)-Mandelonitrile beta-D-glucosideChEBI
(S)-O-beta-D-GlucopyranosylmandelonitrileChEBI
(S)-SambunigrinChEBI
L-PrunasinChEBI
(S)-(b-D-Glucopyranosyloxy)(phenyl)acetonitrileGenerator
(S)-(Β-D-glucopyranosyloxy)(phenyl)acetonitrileGenerator
(S)-Mandelonitrile b-D-glucosideGenerator
(S)-Mandelonitrile β-D-glucosideGenerator
(S)-O-b-D-GlucopyranosylmandelonitrileGenerator
(S)-O-Β-D-glucopyranosylmandelonitrileGenerator
(2S)-(beta-D-Glucopyranosyloxy)(phenyl)acetonitrileHMDB
(S)-PrunasinHMDB
SambunigrinMeSH
Chemical FormulaC14H17NO6
Average Molecular Weight295.2879
Monoisotopic Molecular Weight295.105587281
IUPAC Name(2S)-2-phenyl-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile
Traditional Name(S)-prunasin
CAS Registry Number99-19-4
SMILES
OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point151 - 152 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility268800 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013582
KNApSAcK IDC00034206
Chemspider ID82563
KEGG Compound IDC04273
BioCyc IDCPD-20541
BiGG IDNot Available
Wikipedia LinkPrunasin
METLIN IDNot Available
PubChem Compound91434
PDB IDNot Available
ChEBI ID27761
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1846771
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .