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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:51:57 UTC
Update Date2018-03-12 21:58:13 UTC
HMDB IDHMDB0034934
Secondary Accession Numbers
  • HMDB34934
Metabolite Identification
Common NamePrunasin
DescriptionPrunasin, also known as (R)-prunasin or prulaurasin, belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. Prunasin exists as a solid, soluble (in water), and a very weakly acidic compound (based on its pKa). Within the cell, prunasin is primarily located in the cytoplasm. Prunasin can be converted into (R)-4-hydroxymandelonitrile beta-D-glucoside. Outside of the human body, prunasin can be found in a number of food items such as peach, fruits, papaya, and herbs and spices. This makes prunasin a potential biomarker for the consumption of these food products. Prunasin is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
(R)-(beta-D-Glucopyranosyloxy)phenylacetonitrileChEBI
(R)-alpha-(beta-D-Glucopyranosyloxy)benzene-acetonitrileChEBI
(R)-Mandelonitrile beta-D-glucopyranosideChEBI
(R)-Mandelonitrile beta-D-glucosideChEBI
D-PrunasinChEBI
(R)-(b-D-Glucopyranosyloxy)phenylacetonitrileGenerator
(R)-(β-D-glucopyranosyloxy)phenylacetonitrileGenerator
(R)-a-(b-D-Glucopyranosyloxy)benzene-acetonitrileGenerator
(R)-α-(β-D-glucopyranosyloxy)benzene-acetonitrileGenerator
(R)-Mandelonitrile b-D-glucopyranosideGenerator
(R)-Mandelonitrile β-D-glucopyranosideGenerator
(R)-Mandelonitrile b-D-glucosideGenerator
(R)-Mandelonitrile β-D-glucosideGenerator
(-)-(2R)-PrunasinHMDB
(-)-PrunasinHMDB
(2R)-(beta-D-Glucopyranosyloxy)(phenyl)acetonitrileHMDB
(2R)-PrunasinHMDB
(R)-PrunasinHMDB
Mandelonitrile-beta-glucosideMeSH
PrulaurasinMeSH
PrunasineMeSH
Prunasin, (R)-isomerMeSH
Chemical FormulaC14H17NO6
Average Molecular Weight295.2879
Monoisotopic Molecular Weight295.105587281
IUPAC Name(2R)-2-phenyl-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile
Traditional Name(R)-prunasin
CAS Registry Number99-18-3
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+/m0/s1
InChI KeyZKSZEJFBGODIJW-GMDXDWKASA-N
Chemical Taxonomy
DescriptionThis compound 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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point147 - 148 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Polarizability28.55 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02e9-5970000000-af7eea9783215b5077ecView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-014i-2411490000-eb6d4c8c77d360144d24View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0950000000-94af28ff3325aa91829fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-0900000000-c209318aed53a776a604View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067i-3900000000-f46229fde33733da738aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-1890000000-a1a34454361f8a461a19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2910000000-9efa8331da9f7f35adb0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-9800000000-6551bbcd67cdb9809506View in MoNA
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
FoodDB IDFDB013526
KNApSAcK IDC00001454 C00034206
Chemspider ID106360
KEGG Compound IDC00844
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPrunasin
METLIN IDNot Available
PubChem Compound119033
PDB IDNot Available
ChEBI ID17396
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.. .

Enzymes

General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Glycosidase probably involved in the intestinal absorption and metabolism of dietary flavonoid glycosides. Able to hydrolyze a broad variety of glycosides including phytoestrogens, flavonols, flavones, flavanones and cyanogens. Possesses beta-glycosylceramidase activity and may be involved in a nonlysosomal catabolic pathway of glycosylceramide.
Gene Name:
GBA3
Uniprot ID:
Q9H227
Molecular weight:
Not Available
Reactions
Prunasin + Water → Mandelonitrile + D-Glucosedetails
Prunasin + D-Glucose → Amygdalin + Waterdetails