DHURRIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H17NO7
Molecular Weight	311.2873
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

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

InChIKey=NVLTYOJHPBMILU-YOVYLDAJSA-N

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

HIDE SMILES / InChI

Molecular Formula	C14H17NO7
Molecular Weight	311.2873
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Plant science. Dynamic metabolons.	2010-12-03	21127236
Creation of a genome-wide metabolic pathway database for Populus trichocarpa using a new approach for reconstruction and curation of metabolic pathways for plants.	2010-08	20522724
Genetic screening identifies cyanogenesis-deficient mutants of Lotus japonicus and reveals enzymatic specificity in hydroxynitrile glucoside metabolism.	2010-05	20453117
Metabolic profiling of Arabidopsis thaliana epidermal cells.	2010-03	20150518
Identification of flavone phytoalexins and a pathogen-inducible flavone synthase II gene (SbFNSII) in sorghum.	2010-02	20007684
Metabolomic, transcriptional, hormonal, and signaling cross-talk in superroot2.	2010-01	20008451
454 pyrosequencing based transcriptome analysis of Zygaena filipendulae with focus on genes involved in biosynthesis of cyanogenic glucosides.	2009-12-02	19954531
Phenolic compounds in ectomycorrhizal interaction of lignin modified silver birch.	2009-09-29	19788757
Chemical diversity and defence metabolism: how plants cope with pathogens and ozone pollution.	2009-07-30	20111684
Scale-free flow of life: on the biology, economics, and physics of the cell.	2009-05-05	19416527
Metabolon formation in dhurrin biosynthesis.	2008-01	17706731
Rate of hydrolysis and degradation of the cyanogenic glycoside - dhurrin - in soil.	2007-02	17126881
Analysis of rice glycosyl hydrolase family 1 and expression of Os4bglu12 beta-glucosidase.	2006-12-29	17196101
Consequences of transferring three sorghum genes for secondary metabolite (cyanogenic glucoside) biosynthesis to grapevine hairy roots.	2006-04	16604459
Reconstitution of cyanogenesis in barley (Hordeum vulgare L.) and its implications for resistance against the barley powdery mildew fungus.	2006-04	16307283
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.	2005-10	16169969
Predictive metabolic engineering in plants: still full of surprises.	2005-08	15922468
Cyanogenic glycosides and menisdaurin from Guazuma ulmifolia, Ostrya virgininana, Tiquilia plicata and Tiquilia canescens.	2005-07	16002108
Tailoring the plant metabolome without a loose stitch.	2005-07	15950519
Structural determinants of substrate specificity in family 1 beta-glucosidases: novel insights from the crystal structure of sorghum dhurrinase-1, a plant beta-glucosidase with strict specificity, in complex with its natural substrate.	2004-07-23	15148317
Raman spectroscopic analysis of cyanogenic glucosides in plants: development of a flow injection surface-enhanced Raman scatter (FI-SERS) method for determination of cyanide.	2004-02	15000716
Metabolic channeling in plants.	2004	15725058
The in vitro substrate regiospecificity of recombinant UGT85B1, the cyanohydrin glucosyltransferase from Sorghum bicolor.	2003-09	12946413
Conservation and diversity of gene families explored using the CODEHOP strategy in higher plants.	2002-08-01	12153706
Dhurrin synthesis in sorghum is regulated at the transcriptional level and induced by nitrogen fertilization in older plants.	2002-07	12114576
Resistance to an herbivore through engineered cyanogenic glucoside synthesis.	2001-09-07	11474068
Metabolism of tyrosine and tryptophan--new genes for old pathways.	2001-06	11312134

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:55:00 GMT 2025` Edited by `admin` on `Mon Mar 31 19:55:00 GMT 2025`
Record UNII	P5999IY65C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

(.ALPHA.S)-.ALPHA.-(.BETA.-D-GLUCOPYRANOSYLOXY)-4-HYDROXYBENZENEACETONITRILE

Preferred Name

English

DHURRIN

Common Name

English

.BETA.-D-GLUCOPYRANOSYLOXY-L-P-HYDROXYMANDELONITRILE

Common Name

English

DHURRIN [MI]

Common Name

English

Code System Code Type Description

ECHA (EC/EINECS)

207-878-6