1.0 2010-04-08 22:10:48 UTC 2025-11-18 23:52:04 UTC FDB013582 Sambunigrin Isolated 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)-Prunasin L-Prunasin Sambunigrin C14H17NO6 295.2879 295.105587281 (2S)-2-phenyl-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile (S)-prunasin 99-19-4 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=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/s1 ZKSZEJFBGODIJW-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 glycosides Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aromatic heteromonocyclic compounds Acetals Benzene and substituted derivatives Hexoses Hydrocarbon derivatives Nitriles O-glycosyl compounds Organopnictogen compounds Oxacyclic compounds Oxanes Polyols Primary alcohols Secondary alcohols Acetal Alcohol Aromatic heteromonocyclic compound Benzenoid Carbonitrile Cyanogenic glycoside Hexose monosaccharide Hydrocarbon derivative Monocyclic benzene moiety Monosaccharide Nitrile O-glycosyl compound Organic nitrogen compound Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Oxane Polyol Primary alcohol Secondary alcohol Cyanogenic glucosides derived from phenylalanine Cyanogenic glycosides prunasin logp -0.56 ALOGPS logs -1.02 ALOGPS solubility 2.82e+01 g/l ALOGPS melting_point Mp 151-152° logp -0.82 ChemAxon pka_strongest_acidic 12.21 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2S)-2-phenyl-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile ChemAxon average_mass 295.2879 ChemAxon mono_mass 295.105587281 ChemAxon 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 ChemAxon formula C14H17NO6 ChemAxon inchi 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-/m1/s1 ChemAxon inchikey ZKSZEJFBGODIJW-YOVYLDAJSA-N ChemAxon polar_surface_area 123.17 ChemAxon refractivity 70.1 ChemAxon polarizability 29.09 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 25451 Specdb::CMs 44121 Specdb::CMs 154018 Specdb::NmrOneD 128768 Specdb::NmrOneD 128769 Specdb::NmrOneD 128770 Specdb::NmrOneD 128771 Specdb::NmrOneD 128772 Specdb::NmrOneD 128773 Specdb::NmrOneD 128774 Specdb::NmrOneD 128775 Specdb::NmrOneD 128776 Specdb::NmrOneD 128777 Specdb::NmrOneD 128778 Specdb::NmrOneD 128779 Specdb::NmrOneD 128780 Specdb::NmrOneD 128781 Specdb::NmrOneD 128782 Specdb::NmrOneD 128783 Specdb::NmrOneD 128784 Specdb::NmrOneD 128785 Specdb::NmrOneD 128786 Specdb::NmrOneD 128787 Specdb::MsMs 79929 Specdb::MsMs 79930 Specdb::MsMs 79931 Specdb::MsMs 140643 Specdb::MsMs 140644 Specdb::MsMs 140645 Specdb::MsMs 2455492 Specdb::MsMs 2455493 Specdb::MsMs 2455494 Specdb::MsMs 2480158 Specdb::MsMs 2480159 Specdb::MsMs 2480160 HMDB34981 27761 Black elderberry Type 1 specific Sambucus nigra 4202 42.0 42.0 42.0 mg/100 g Fruits Unknown generic Passion fruit Type 1 specific Passiflora edulis 78168 Aldose reductase inhibitor 40 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). Cyanogenic 845