1.0 2010-04-08 22:10:46 UTC 2019-11-26 03:08:33 UTC FDB013526 Prunasin Isolated 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-acetonitrile D-Prunasin Prunasin C14H17NO6 295.2879 295.105587281 (2R)-2-phenyl-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile (R)-prunasin 99-18-3 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+/m0/s1 ZKSZEJFBGODIJW-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 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 prunasin logp -0.56 ALOGPS logs -1.02 ALOGPS solubility 2.82e+01 g/l ALOGPS melting_point Mp 147-148° logp -0.82 ChemAxon pka_strongest_acidic 12.21 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R)-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+/m0/s1 ChemAxon inchikey ZKSZEJFBGODIJW-GMDXDWKASA-N ChemAxon polar_surface_area 123.17 ChemAxon refractivity 70.1 ChemAxon polarizability 28.55 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 26469 Specdb::CMs 44094 Specdb::CMs 147393 Specdb::NmrOneD 128468 Specdb::NmrOneD 128469 Specdb::NmrOneD 128470 Specdb::NmrOneD 128471 Specdb::NmrOneD 128472 Specdb::NmrOneD 128473 Specdb::NmrOneD 128474 Specdb::NmrOneD 128475 Specdb::NmrOneD 128476 Specdb::NmrOneD 128477 Specdb::NmrOneD 128478 Specdb::NmrOneD 128479 Specdb::NmrOneD 128480 Specdb::NmrOneD 128481 Specdb::NmrOneD 128482 Specdb::NmrOneD 128483 Specdb::NmrOneD 128484 Specdb::NmrOneD 128485 Specdb::NmrOneD 128486 Specdb::NmrOneD 128487 Specdb::MsMs 89598 Specdb::MsMs 89599 Specdb::MsMs 89600 Specdb::MsMs 152559 Specdb::MsMs 152560 Specdb::MsMs 152561 Specdb::MsMs 2743732 Specdb::MsMs 2743733 Specdb::MsMs 2743734 Specdb::MsMs 2934420 Specdb::MsMs 2934421 Specdb::MsMs 2934422 HMDB34934 17396 #<Reference:0x000056127324b978> Almond Type 1 specific Prunus dulcis 3755 Black elderberry Type 1 specific Sambucus nigra 4202 Fruits Unknown generic Herbs and Spices Unknown generic Papaya Type 1 specific Carica papaya 3649 Passion fruit Type 1 specific Passiflora edulis 78168 Peach Type 1 specific Prunus persica 3760 Sour cherry Type 1 specific Prunus cerasus 140311 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