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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:51:57 UTC
Update Date2021-10-13 06:44:34 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 in all living organisms, ranging from bacteria to humans. Prunasin has been detected, but not quantified in, several different foods, such as herbs and spices, papayas (Carica papaya), sour cherries (Prunus cerasus), black elderberries (Sambucus nigra), and passion fruits (Passiflora edulis). This could make prunasin a potential biomarker for the consumption of these foods. Prunasin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Prunasin.
Structure
Data?1563862638
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)-PrunasinKegg
(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
Mandelonitrile-beta-glucosideMeSH
PrulaurasinMeSH
Prunasin, (R)-isomerMeSH
PrunasineMeSH
(-)-(2R)-PrunasinHMDB
(-)-PrunasinHMDB
(2R)-(beta-D-Glucopyranosyloxy)(phenyl)acetonitrileHMDB
(2R)-PrunasinHMDB
PrunasinChEBI
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
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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point147 - 148 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility8.56 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility28.2 g/LALOGPS
logP10(-0.56) g/LALOGPS
logP10(-0.82) g/LChemAxon
logS10(-1) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+166.79731661259
DarkChem[M-H]-165.21931661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Prunasin,1TMS,#1C[Si](C)(C)OC[C@H]1O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O2246.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,1TMS,#2C[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H](C#N)C1=CC=CC=C12253.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,1TMS,#3C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@@H]1O2259.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,1TMS,#4C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@H](O)[C@H]1O2257.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,2TMS,#1C[Si](C)(C)OC[C@H]1O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O2243.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,2TMS,#2C[Si](C)(C)OC[C@H]1O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O2266.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,2TMS,#3C[Si](C)(C)OC[C@H]1O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C2267.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,2TMS,#4C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@@H]1O[Si](C)(C)C2269.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,2TMS,#5C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O[C@@H](C#N)C2=CC=CC=C2)O[C@@H]1CO2269.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,2TMS,#6C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@H](O)[C@H]1O[Si](C)(C)C2259.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,3TMS,#1C[Si](C)(C)OC[C@H]1O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O2280.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,3TMS,#2C[Si](C)(C)OC[C@H]1O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C2281.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,3TMS,#3C[Si](C)(C)OC[C@H]1O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2286.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,3TMS,#4C[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C)[C@@H](CO)O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@@H]1O[Si](C)(C)C2277.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,4TMS,#1C[Si](C)(C)OC[C@H]1O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2301.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,1TBDMS,#1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O2491.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,1TBDMS,#2CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H](C#N)C1=CC=CC=C12489.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,1TBDMS,#3CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@@H]1O2487.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,1TBDMS,#4CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@H](O)[C@H]1O2500.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,2TBDMS,#1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O2726.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,2TBDMS,#2CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O2729.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,2TBDMS,#3CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C2741.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,2TBDMS,#4CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@@H]1O[Si](C)(C)C(C)(C)C2722.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,2TBDMS,#5CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[C@@H](C#N)C2=CC=CC=C2)O[C@@H]1CO2723.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,2TBDMS,#6CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C2715.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,3TBDMS,#1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O2924.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,3TBDMS,#2CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C2914.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,3TBDMS,#3CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C2925.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,3TBDMS,#4CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@@H]1O[Si](C)(C)C(C)(C)C2916.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Prunasin,4TBDMS,#1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3108.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Prunasin GC-MS (Non-derivatized) - 70eV, Positivesplash10-02e9-5970000000-af7eea9783215b5077ec2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prunasin GC-MS (4 TMS) - 70eV, Positivesplash10-014i-2411490000-eb6d4c8c77d360144d242017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prunasin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prunasin 10V, Positive-QTOFsplash10-001j-0950000000-94af28ff3325aa91829f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prunasin 20V, Positive-QTOFsplash10-00lr-0900000000-c209318aed53a776a6042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prunasin 40V, Positive-QTOFsplash10-067i-3900000000-f46229fde33733da738a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prunasin 10V, Negative-QTOFsplash10-000x-1890000000-a1a34454361f8a461a192016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prunasin 20V, Negative-QTOFsplash10-001i-2910000000-9efa8331da9f7f35adb02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prunasin 40V, Negative-QTOFsplash10-003r-9800000000-6551bbcd67cdb98095062016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prunasin 10V, Positive-QTOFsplash10-014j-0930000000-b073c628b5ae90962ddb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prunasin 20V, Positive-QTOFsplash10-0159-1930000000-0195cac2f79233b86e612021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prunasin 40V, Positive-QTOFsplash10-014i-6900000000-14cef03a9110265ac2a22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prunasin 10V, Negative-QTOFsplash10-0006-0950000000-911e901878111f3552da2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prunasin 20V, Negative-QTOFsplash10-0gc0-1910000000-e65f091dbdc8f43dd35c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prunasin 40V, Negative-QTOFsplash10-00lr-2900000000-ae791f613076bd2826062021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
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 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1592501
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