Molecule

(S)-4-hydroxymandelonitrile beta-D-glucoside

AlkaPlorer ID: AK018085

Synonym: 'Dhurrin', '', 'Taxiphyllin', '(2R)-taxiphyllin', '(alphaS)-alpha-(beta-D-glucopyranosyloxy)-4-hydroxybenzeneacetonitrile', '(S)-(beta-D-glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile', 'dhurrin', '(2S)-dhurrin', '(S)-4-Hydroxymandelonitrile beta-D-glucoside'

IUPAC Name: (2S)-2-(4-hydroxyphenyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile

Structure

SMILES: N#C[C@@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C1=CC=C(O)C=C1

InChI: InChI=1S/C14H17NO7/c15-5-9(7-1-3-8(17)4-2-7)21-14-13(20)12(19)11(18)10(6-16)22-14/h1-4,9-14,16-20H,6H2/t9-,10-,11-,12+,13-,14-/m1/s1

InChIKey: NVLTYOJHPBMILU-YOVYLDAJSA-N

Reference

The Primary Sequence of Cytochrome P450tyr, the MultifunctionalN-Hydroxylase Catalyzing the Conversion ofL-Tyrosine top-Hydroxyphenylacetaldehyde Oxime in the Biosynthesis of the Cyanogenic Glucoside Dhurrin inSorghum bicolor(L.) Moench

PubChem CID: 161355

CAS: 499-20-7

LOTUS: LTS0063687

SuperNatural Ⅲ: SN0256366-06

NPASS: NPC109759

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Hypomyces rosellus	Hypomyces	Hypocreaceae	Hypocreales	Sordariomycetes	Ascomycota	Fungi	Eukaryota
Glutamicibacter nicotianae	Glutamicibacter	Micrococcaceae	Micrococcales	Actinomycetes	Actinomycetota	None	Bacteria
Solanum incanum	Solanum	Solanaceae	Solanales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Tetragonotheca helianthoides	Tetragonotheca	Asteraceae	Asterales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Hovenia trichocarpa	Hovenia	Rhamnaceae	Rosales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Aspergillus alliaceus	Aspergillus	Aspergillaceae	Eurotiales	Eurotiomycetes	Ascomycota	Fungi	Eukaryota
Berberis nummularia	Berberis	Berberidaceae	Ranunculales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Selaginella moellendorffii	Selaginella	Selaginellaceae	Selaginellales	Lycopodiopsida	Streptophyta	Viridiplantae	Eukaryota
Olearia paniculata	Olearia	Asteraceae	Asterales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Mycobacterium avium	Mycobacterium	Mycobacteriaceae	Mycobacteriales	Actinomycetes	Actinomycetota	None	Bacteria

Properties Information

Molecule Weight: 311.29

TPSA？: 143.4

MolLogP？: -1.22662

Number of H-Donors: 5

Number of H-Acceptors: 8

RingCount: 2

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT015575	N#CC(O)c1ccc(O)cc1.O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H]2O)c(=O)[nH]1>>N#C[C@@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)c1ccc(O)cc1	enzymemap_38130
AKRT015577	N#CC(O)c1ccc(O)cc1.OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O>>N#C[C@@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)c1ccc(O)cc1	MNXR131828
AKRT015675	N#C[C@@H](O)c1ccc(O)cc1.O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H]2O)c(=O)[nH]1>>N#C[C@@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)c1ccc(O)cc1	RXN-743
AKRT015701	N#C[C@@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)c1ccc(O)cc1>>C#N	enzymemap_60840
AKRT015702	N#C[C@@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)c1ccc(O)cc1>>N#CC(O)c1ccc(O)cc1	enzymemap_58918
AKRT015703	N#C[C@@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)c1ccc(O)cc1>>N#C[C@@H](O)c1ccc(O)cc1	RXN-9588
AKRT015704	N#C[C@@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)c1ccc(O)cc1>>N#C[C@@H](O)c1ccc(O)cc1.OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O	None
AKRT015705	N#C[C@@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)c1ccc(O)cc1>>N#C[C@@H](O)c1ccc(O)cc1.OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O	None
AKRT015706	N#C[C@@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)c1ccc(O)cc1>>O=Cc1ccc(O)cc1	enzymemap_60840
AKRT015707	N#C[C@@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)c1ccc(O)cc1>>OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O	RXN-9588
AKRT015708	N#C[C@@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)c1ccc(O)cc1>>OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O	R10035