1.02010-04-08 22:10:46 UTC2019-11-26 03:08:33 UTCFDB013526PrunasinIsolated from kernels of Prunus subspecies, immature fruits of Passiflora subspecies and leaves of perilla (Perilla frutescens variety acuta). Prunasin is found in many foods, some of which are almond, sour cherry, black elderberry, and herbs and spices.(-)-(2R)-Prunasin(-)-Prunasin(2R)-(beta-D-Glucopyranosyloxy)(phenyl)acetonitrile(2R)-Prunasin(R)-(b-D-Glucopyranosyloxy)phenylacetonitrile(R)-(beta-D-Glucopyranosyloxy)phenylacetonitrile(R)-(β-D-glucopyranosyloxy)phenylacetonitrile(R)-a-(b-D-Glucopyranosyloxy)benzene-acetonitrile(R)-alpha-(beta-D-Glucopyranosyloxy)benzene-acetonitrile(R)-Mandelonitrile b-D-glucopyranoside(R)-Mandelonitrile b-D-glucoside(R)-Mandelonitrile beta-D-glucopyranoside(R)-Mandelonitrile beta-D-glucoside(R)-Mandelonitrile β-D-glucopyranoside(R)-Mandelonitrile β-D-glucoside(R)-Prunasin(R)-α-(β-D-glucopyranosyloxy)benzene-acetonitrileD-PrunasinPrunasinC14H17NO6295.2879295.105587281(2R)-2-phenyl-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile(R)-prunasin99-18-3OC[C@H]1O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1OInChI=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/s1ZKSZEJFBGODIJW-GMDXDWKASA-N belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group.Cyanogenic glycosidesOrganic compoundsOrganic oxygen compoundsOrganooxygen compoundsCarbohydrates and carbohydrate conjugatesAromatic heteromonocyclic compoundsAcetalsBenzene and substituted derivativesHexosesHydrocarbon derivativesNitrilesO-glycosyl compoundsOrganopnictogen compoundsOxacyclic compoundsOxanesPolyolsPrimary alcoholsSecondary alcoholsAcetalAlcoholAromatic heteromonocyclic compoundBenzenoidCarbonitrileCyanogenic glycosideHexose monosaccharideHydrocarbon derivativeMonocyclic benzene moietyMonosaccharideNitrileO-glycosyl compoundOrganic nitrogen compoundOrganoheterocyclic compoundOrganonitrogen compoundOrganopnictogen compoundOxacycleOxanePolyolPrimary alcoholSecondary alcoholprunasinlogp-0.56logs-1.02solubility2.82e+01 g/lmelting_pointMp 147-148°logp-0.82pka_strongest_acidic12.21pka_strongest_basic-3iupac(2R)-2-phenyl-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrileaverage_mass295.2879mono_mass295.105587281smilesOC[C@H]1O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1OformulaC14H17NO6inchiInChI=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/s1inchikeyZKSZEJFBGODIJW-GMDXDWKASA-Npolar_surface_area123.17refractivity70.1polarizability28.55rotatable_bond_count4acceptor_count7donor_count4physiological_charge0formal_charge0Specdb::CMs26469Specdb::CMs44094Specdb::CMs147393Specdb::NmrOneD128468Specdb::NmrOneD128469Specdb::NmrOneD128470Specdb::NmrOneD128471Specdb::NmrOneD128472Specdb::NmrOneD128473Specdb::NmrOneD128474Specdb::NmrOneD128475Specdb::NmrOneD128476Specdb::NmrOneD128477Specdb::NmrOneD128478Specdb::NmrOneD128479Specdb::NmrOneD128480Specdb::NmrOneD128481Specdb::NmrOneD128482Specdb::NmrOneD128483Specdb::NmrOneD128484Specdb::NmrOneD128485Specdb::NmrOneD128486Specdb::NmrOneD128487Specdb::MsMs89598Specdb::MsMs89599Specdb::MsMs89600Specdb::MsMs152559Specdb::MsMs152560Specdb::MsMs152561Specdb::MsMs2743732Specdb::MsMs2743733Specdb::MsMs2743734Specdb::MsMs2934420Specdb::MsMs2934421Specdb::MsMs2934422HMDB3493417396#<Reference:0x0000555675e3b770>AlmondType 1specificPrunus dulcis3755Black elderberryType 1specificSambucus nigra4202FruitsUnknowngenericHerbs and SpicesUnknowngenericPapayaType 1specificCarica papaya3649Passion fruitType 1specificPassiflora edulis78168PeachType 1specificPrunus persica3760Sour cherryType 1specificPrunus cerasus140311aldose reductase inhibitor40An 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).cyanogenic845