CHEBI:27826 - (S)-4-hydroxymandelonitrile β-D-glucoside

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ChEBI Name (S)-4-hydroxymandelonitrile β-D-glucoside
ChEBI ID CHEBI:27826
ChEBI ASCII Name (S)-4-hydroxymandelonitrile beta-D-glucoside
Definition A β-D-glucoside consisting of (S)-prunasin carrying a hydroxy substituent at position 4 on the phenyl ring.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:11051, CHEBI:407, CHEBI:4475, CHEBI:18760
Supplier Information
Download Molfile XML SDF
Formula C14H17NO7
Net Charge 0
Average Mass 311.28732
Monoisotopic Mass 311.10050
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
SMILES OC[C@H]1O[C@@H](O[C@H](C#N)c2ccc(O)cc2)[C@H](O)[C@@H](O)[C@@H]1O
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via cyanogenic glycoside )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (S)-4-hydroxymandelonitrile β-D-glucoside (CHEBI:27826) has functional parent (S)-prunasin (CHEBI:27761)
(S)-4-hydroxymandelonitrile β-D-glucoside (CHEBI:27826) is a β-D-glucoside (CHEBI:22798)
(S)-4-hydroxymandelonitrile β-D-glucoside (CHEBI:27826) is a cyanogenic glycoside (CHEBI:23436)
(S)-4-hydroxymandelonitrile β-D-glucoside (CHEBI:27826) is a monosaccharide derivative (CHEBI:63367)
(S)-4-hydroxymandelonitrile β-D-glucoside (CHEBI:27826) is a nitrile (CHEBI:18379)
IUPAC Name
(2S)-(β-D-glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile
Synonyms Sources
(αS)-α-(β-D-glucopyranosyloxy)-4-hydroxybenzeneacetonitrile ChemIDplus
(S)-(β-D-glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile ChemIDplus
(S)-4-Hydroxymandelonitrile beta-D-glucoside KEGG COMPOUND
Dhurrin KEGG COMPOUND
dhurrin UniProt
Manual Xrefs Databases
C00001442 KNApSAcK
C05143 KEGG COMPOUND
View more database links
Registry Numbers Types Sources
499-20-7 CAS Registry Number ChemIDplus
92611 Beilstein Registry Number Beilstein
92611 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12114576 PubMed citation Europe PMC
16660850 PubMed citation Europe PMC
16663720 PubMed citation Europe PMC
16666964 PubMed citation Europe PMC
16667820 PubMed citation Europe PMC
17126881 PubMed citation Europe PMC
17706731 PubMed citation Europe PMC
18003897 PubMed citation Europe PMC
21541942 PubMed citation Europe PMC
21707058 PubMed citation Europe PMC
237909 PubMed citation Europe PMC
Last Modified
28 July 2014
General Comment
2011-07-18 A cyanogenic glucoside from the fruit of young Sorghum vulgare.