Back to Compounds

Showing Compound Prunasin (FDB013526)

Record Information
Version1.0
Creation date2010-04-08 22:10:46 UTC
Update date2019-11-26 03:08:33 UTC
Primary IDFDB013526
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 peaches (Prunus persica), sour cherries (Prunus cerasus), almonds (Prunus dulcis), herbs and spices, and passion fruits (Passiflora edulis). This could make prunasin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Prunasin.
CAS Number99-18-3
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(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
(R)-(β-D-glucopyranosyloxy)phenylacetonitrileGenerator
(R)-α-(β-D-glucopyranosyloxy)benzene-acetonitrileGenerator
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC14H17NO6
IUPAC name(2R)-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+/m0/s1
InChI KeyZKSZEJFBGODIJW-GMDXDWKASA-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 147-148°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -29.6 (H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPrunasin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-02e9-5970000000-af7eea9783215b5077ecSpectrum
Predicted GC-MSPrunasin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-2411490000-eb6d4c8c77d360144d24Spectrum
Predicted GC-MSPrunasin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0950000000-94af28ff3325aa91829f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-0900000000-c209318aed53a776a6042016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067i-3900000000-f46229fde33733da738a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-1890000000-a1a34454361f8a461a192016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2910000000-9efa8331da9f7f35adb02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-9800000000-6551bbcd67cdb98095062016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0930000000-b073c628b5ae90962ddb2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-1930000000-0195cac2f79233b86e612021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-6900000000-14cef03a9110265ac2a22021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0950000000-911e901878111f3552da2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gc0-1910000000-e65f091dbdc8f43dd35c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-2900000000-ae791f613076bd2826062021-09-24View Spectrum
NMRNot Available
ChemSpider ID106360
ChEMBL IDCHEMBL1778417
KEGG Compound IDC00844
Pubchem Compound ID119033
Pubchem Substance IDNot Available
ChEBI ID17396
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34934
CRC / DFC (Dictionary of Food Compounds) IDJDX91-A:JDX99-I
EAFUS IDNot Available
Dr. Duke IDPRUNASIN
BIGG IDNot Available
KNApSAcK IDC00001454
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— 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.