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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:23:14 UTC
Update Date2019-07-23 07:14:24 UTC
HMDB IDHMDB0060471
Secondary Accession Numbers
  • HMDB60471
Metabolite Identification
Common NameDhurrin
DescriptionDhurrin is a cyanogenic glycoside occurring in plants. Its biosynthesis has been elucidated. Dhurrin is hydrolyzed in the stomach of an insect into a carbohydrate and aglycone. The aglycone is unstable and releases hydrogen cyanide. (Wikipedia) In biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor, the UDP-glucosyltransferase UGT85B1 catalyzes the conversion of p-hydroxymandelonitrile into dhurrin. (PMID: 16169969 ) In Sorghum, the cyanogenic glucoside dhurrin is derived from l-tyrosine in a pathway involving the two cytochromes P450 (CYPs) CYP79A1 and CYP71E1, a glucosyltransferase (UGT85B1), and the redox partner NADPH-dependent cytochrome P450 reductase (CPR). (PMID: 21620426 ) Synthesis of the tyrosine derived cyanogenic glucoside dhurrin in Sorghum bicolor is catalyzed by two multifunctional, membrane bound cytochromes P450, CYP79A1 and CYP71E1, and a soluble UDPG-glucosyltransferase, UGT85B1. In the presence of CYP79A1 and CYP71E1, the localization of UGT85B1 shifted towards the surface of the ER membrane in the periphery of biosynthetic active cells, demonstrating in planta dhurrin metabolon formation. (PMID: 17706731 )
Structure
Data?1563866064
Synonyms
ValueSource
(AlphaS)-alpha-(beta-D-glucopyranosyloxy)-4-hydroxybenzeneacetonitrileChEBI
(S)-(beta-D-Glucopyranosyloxy)(4-hydroxyphenyl)acetonitrileChEBI
DhurrinChEBI
(AlphaS)-a-(b-D-glucopyranosyloxy)-4-hydroxybenzeneacetonitrileGenerator
(AlphaS)-α-(β-D-glucopyranosyloxy)-4-hydroxybenzeneacetonitrileGenerator
(S)-4-Hydroxymandelonitrile b-D-glucosideGenerator
(S)-4-Hydroxymandelonitrile β-D-glucosideGenerator
(S)-(b-D-Glucopyranosyloxy)(4-hydroxyphenyl)acetonitrileGenerator
(S)-(β-D-glucopyranosyloxy)(4-hydroxyphenyl)acetonitrileGenerator
Chemical FormulaC14H17NO7
Average Molecular Weight311.2873
Monoisotopic Molecular Weight311.100501903
IUPAC Name(2S)-2-(4-hydroxyphenyl)-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile
Traditional Namedhurrin
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
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
InChI KeyNVLTYOJHPBMILU-YOVYLDAJSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentCyanogenic glycosides
Alternative Parents
Substituents
  • Cyanogenic glycoside
  • Hexose monosaccharide
  • O-glycosyl compound
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Secondary alcohol
  • Polyol
  • Oxacycle
  • Nitrile
  • Carbonitrile
  • Acetal
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organopnictogen compound
  • Organic nitrogen compound
  • Primary alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility28.4 g/LALOGPS
logP-0.77ALOGPS
logP-1.1ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)9.46ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area143.4 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.08 m³·mol⁻¹ChemAxon
Polarizability29.37 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-6980000000-f80d5117e719acd7ea21JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-0a4i-2120139000-64b3d92eecffc4b7a926JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w29-0923000000-cf26d31410f4a6bbf49bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0900000000-b87d3729a9263154ed95JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ul1-2900000000-f33010875c02895c0fb1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-0829000000-ebfe73bcd41e6a182465JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-2910000000-36f398a6b58bb479e425JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-8900000000-aff50f1ad716828a3472JSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00001442
Chemspider IDNot Available
KEGG Compound IDC05143
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound161355
PDB IDNot Available
ChEBI ID27826
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  2. Thorsoe KS, Bak S, Olsen CE, Imberty A, Breton C, Lindberg Moller B: Determination of catalytic key amino acids and UDP sugar donor specificity of the cyanohydrin glycosyltransferase UGT85B1 from Sorghum bicolor. Molecular modeling substantiated by site-specific mutagenesis and biochemical analyses. Plant Physiol. 2005 Oct;139(2):664-73. Epub 2005 Sep 16. [PubMed:16169969 ]
  3. Jensen K, Osmani SA, Hamann T, Naur P, Moller BL: Homology modeling of the three membrane proteins of the dhurrin metabolon: catalytic sites, membrane surface association and protein-protein interactions. Phytochemistry. 2011 Dec;72(17):2113-23. doi: 10.1016/j.phytochem.2011.05.001. Epub 2011 May 26. [PubMed:21620426 ]
  4. Nielsen KA, Tattersall DB, Jones PR, Moller BL: Metabolon formation in dhurrin biosynthesis. Phytochemistry. 2008 Jan;69(1):88-98. Epub 2007 Aug 15. [PubMed:17706731 ]

Enzymes

General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Glycosidase probably involved in the intestinal absorption and metabolism of dietary flavonoid glycosides. Able to hydrolyze a broad variety of glycosides including phytoestrogens, flavonols, flavones, flavanones and cyanogens. Possesses beta-glycosylceramidase activity and may be involved in a nonlysosomal catabolic pathway of glycosylceramide.
Gene Name:
GBA3
Uniprot ID:
Q9H227
Molecular weight:
Not Available
Reactions
Dhurrin + Water → (S)-4-Hydroxymandelonitrile + beta-D-Glucosedetails