1.02010-04-08 22:10:48 UTC2019-11-26 03:08:39 UTCFDB013582SambunigrinIsolated from leaves of elderberry (Sambucus nigra) and from other plants. Sambunigrin is found in passion fruit, fruits, and black elderberry.(2S)-(beta-D-Glucopyranosyloxy)(phenyl)acetonitrile(2S)-Sambunigrin(S)-Mandelonitrile beta-D-glucoside(S)-PrunasinL-PrunasinSambunigrinC14H17NO6295.2879295.105587281(2S)-2-phenyl-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile(S)-prunasin99-19-4OC[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-/m1/s1ZKSZEJFBGODIJW-YOVYLDAJSA-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 alcoholCyanogenic glucosides derived from phenylalanineCyanogenic glycosidesprunasinlogp-0.56logs-1.02solubility2.82e+01 g/lmelting_pointMp 151-152°logp-0.82pka_strongest_acidic12.21pka_strongest_basic-3iupac(2S)-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-/m1/s1inchikeyZKSZEJFBGODIJW-YOVYLDAJSA-Npolar_surface_area123.17refractivity70.1polarizability29.09rotatable_bond_count4acceptor_count7donor_count4physiological_charge0formal_charge0Specdb::CMs25451Specdb::CMs44121Specdb::CMs154018Specdb::MsMs79929Specdb::MsMs79930Specdb::MsMs79931Specdb::MsMs140643Specdb::MsMs140644Specdb::MsMs140645Specdb::MsMs2455492Specdb::MsMs2455493Specdb::MsMs2455494Specdb::MsMs2480158Specdb::MsMs2480159Specdb::MsMs2480160Specdb::NmrOneD128768Specdb::NmrOneD128769Specdb::NmrOneD128770Specdb::NmrOneD128771Specdb::NmrOneD128772Specdb::NmrOneD128773Specdb::NmrOneD128774Specdb::NmrOneD128775Specdb::NmrOneD128776Specdb::NmrOneD128777Specdb::NmrOneD128778Specdb::NmrOneD128779Specdb::NmrOneD128780Specdb::NmrOneD128781Specdb::NmrOneD128782Specdb::NmrOneD128783Specdb::NmrOneD128784Specdb::NmrOneD128785Specdb::NmrOneD128786Specdb::NmrOneD128787HMDB3498127761Black elderberryType 1specificSambucus nigra420242.042.042.0mg/100 gFruitsUnknowngenericPassion fruitType 1specificPassiflora edulis78168aldose 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