Compounds > lotaustralin
Page last updated: 2024-12-08

lotaustralin

Description

lotaustralin: higher homologue of linamarin from flax; a cyanogenic glycoside; RN given refers to (R)-isomer; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID441467
CHEBI ID6542
SCHEMBL ID42924
MeSH IDM0041788

Synonyms (25)

Synonym
2(r)-hydroxy-2-methylbutyronitrile-beta-d-glucopyranoside
p588137a94 ,
butanenitrile, 2-(beta-d-glucopyranosyloxy)-2-methyl-, (r)-
unii-p588137a94
534-67-8
C08334 ,
lotaustralin
2-hydroxy-2-methylbutyronitrile-beta-d-glucopyranoside
AC1L9B81 ,
(2r)-2-methyl-2-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutanenitrile
2-methyl-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutanenitrile
butanenitrile, 2-(.beta.-d-glucopyranosyloxy)-2-methyl-, (2r)-
.beta.-d-glucopyranosyloxy-2-methylbutyronitrile (r)
SCHEMBL42924
CHEBI:6542
surecn42924
zinc04097529
(2r)-2-methyl-2-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-butanenitrile
DTXSID30897501
Q905492
(r)-2-methyl-2-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)butanenitrile
(r)-2-(beta-d-glucopyranosyloxy)-2-methylbutyronitrile
(2r)-2-(beta-d-glucopyranosyloxy)-2-methyl-butanenitrile;
(2r)-2-methyl-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanenitrile
AKOS040752682

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"The toxic effects of cassava diets on humans were reviewed."( The toxic effects of cassava (manihot esculenta grantz) diets on humans: a review.
Agunbiade, OO; Aregheore, EM, 1991)		0.28
" In order to achieve safe levels of 10 μg/g in cassava products, new methods of processing, especially for cassava containing more than 250 μg CN eq."( Strategies for elimination of cyanogens from cassava for reducing toxicity and improving food safety.
Nambisan, B, 2011)		0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
cyanogenic glycosideA glycoside in which the aglycone contains a cyanide group. A cyanogenic glycoside can release poisonous hydrogen cyanide if acted upon by some enzyme.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (4)

PathwayProteinsCompounds
lotaustralin degradation18
neolinustatin bioactivation08
lotaustralin biosynthesis014
superpathway of linamarin and lotaustralin biosynthesis023

Research

Studies (31)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (22.58)18.7374
1990's5 (16.13)18.2507
2000's7 (22.58)29.6817
2010's12 (38.71)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 30.82

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index30.82 (24.57)
Research Supply Index3.50 (2.92)
Research Growth Index4.65 (4.65)
Search Engine Demand Index39.34 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (30.82)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (6.25%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other30 (93.75%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
acetone
methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).		1.9410ketone body;
methyl ketone;
propanones;
volatile organic compound		EC 3.5.1.4 (amidase) inhibitor;
human metabolite;
polar aprotic solvent
carbon monoxide
Carbon Monoxide: Carbon monoxide (CO). A poisonous colorless, odorless, tasteless gas. It combines with hemoglobin to form carboxyhemoglobin, which has no oxygen carrying capacity. The resultant oxygen deprivation causes headache, dizziness, decreased pulse and respiratory rates, unconsciousness, and death. (From Merck Index, 11th ed). carbon monoxide : A one-carbon compound in which the carbon is joined only to a single oxygen. It is a colourless, odourless, tasteless, toxic gas.		2.0610carbon oxide;
gas molecular entity;
one-carbon compound		biomarker;
EC 1.9.3.1 (cytochrome c oxidase) inhibitor;
human metabolite;
ligand;
metabolite;
mitochondrial respiratory-chain inhibitor;
mouse metabolite;
neurotoxin;
neurotransmitter;
P450 inhibitor;
probe;
signalling molecule;
vasodilator agent
hydrogen cyanide
Hydrogen Cyanide: Hydrogen cyanide (HCN); A toxic liquid or colorless gas. It is found in the smoke of various tobacco products and released by combustion of nitrogen-containing organic materials.. hydrogen cyanide : A one-carbon compound consisting of a methine group triple bonded to a nitrogen atom		3.8230hydracid;
one-carbon compound		Escherichia coli metabolite;
human metabolite;
poison
cyanides
Cyanides: Inorganic salts of HYDROGEN CYANIDE containing the -CN radical. The concept also includes isocyanides. It is distinguished from NITRILES, which denotes organic compounds containing the -CN radical.. cyanides : Salts and C-organyl derivatives of hydrogen cyanide, HC#N.. isocyanide : The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)).. cyanide : A pseudohalide anion that is the conjugate base of hydrogen cyanide.		4.1950pseudohalide anionEC 1.9.3.1 (cytochrome c oxidase) inhibitor
valine
Valine: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.. valine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group.. L-valine : The L-enantiomer of valine.		2.6530L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid;
valine		algal metabolite;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
isoleucine
Isoleucine: An essential branched-chain aliphatic amino acid found in many proteins. It is an isomer of LEUCINE. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels.. isoleucine : A 2-amino-3-methylpentanoic acid having either (2R,3R)- or (2S,3S)-configuration.. L-isoleucine : The L-enantiomer of isoleucine.		2.3620aspartate family amino acid;
isoleucine;
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
cyanogen
cyanogen: structure. oxalonitrile : A dinitrile that is ethane substituted by two cyano groups.		7.4720dinitrile;
pseudohalogen
linamarin
[no description available]		6.06220beta-D-glucoside
2'-deoxyadenosine
2'-deoxyformycin A: RN not in Chemline 9/85; RN and structure given in first source		2.0810purine 2'-deoxyribonucleoside;
purines 2'-deoxy-D-ribonucleoside		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
deoxynivalenol
deoxynivalenol : A trichothecene mycotoxin produced by Fusarium to which wheat, barley, maize (corn) and their products are susceptible to contamination.		2.1710cyclic ketone;
enone;
primary alcohol;
secondary alpha-hydroxy ketone;
trichothecene;
triol		mycotoxin
glucose, (beta-d)-isomer
beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.		6.38310D-glucopyranoseepitope;
mouse metabolite
secoisolariciresinol
secoisolariciresinol: RN given refers to ((R-(R*,R*))-isomer); RN for cpd without isomeric designation not available 8/89; precursor of lignans found in human urine; structure given in first source. secoisolariciresinol : A lignan that is butane-1,4-diol in which the 2 and 3 positions are substituted by 4-hydroxy-3-methoxybenzyl groups. (-)-secoisolariciresinol : An enantiomer of secoisolariciresinol having (-)-(2R,3R)-configuration.		2.1110secoisolariciresinolantidepressant;
phytoestrogen;
plant metabolite
linustatin
linustatin: cyanogenic glucoside from linseed oil; structure		2.0810cyanogenic glycoside
neolinustatin
neolinustatin: cyanogenic glucoside from linseed oil; related to amygdalin; structure		2.0810cyanogenic glycoside
rhodioloside
[no description available]		1.9910glycoside
lignans
Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)		2.520
glycosides
[no description available]		4.95120
amygdalin
[no description available]		2.0810
cytellin
cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982		1.9810
zearalenone
Zearalenone: (S-(E))-3,4,5,6,8,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione. One of a group of compounds known under the general designation of resorcylic acid lactones. Cis, trans, dextro and levo forms have been isolated from the fungus Gibberella zeae (formerly Fusarium graminearum). They have estrogenic activity, cause toxicity in livestock as feed contaminant, and have been used as anabolic or estrogen substitutes.. zearalenone : A macrolide comprising a fourteen-membered lactone fused to 1,3-dihydroxybenzene; a potent estrogenic metabolite produced by some Giberella species.		2.1110macrolide;
resorcinols		fungal metabolite;
mycoestrogen
rhodiocyanoside a
rhodiocyanoside A: from Chinese natural medicine, Si Lie Hong Jing Tian, from the underground part of Rhodiola quadrifida; structure given in first source. rhodiocyanoside A : A cyanogenic glycoside that is (2Z)-2-methylbut-2-enenitrile attached to a beta-D-glucopyranosyloxy at position 4. Isolated from Rhodiola quadrifida, it exhibits anti-allergic activity.		7.0210aliphatic nitrile;
beta-D-glucoside;
cyanogenic glycoside;
monosaccharide derivative		anti-allergic agent;
metabolite
secoisolariciresinol diglucoside
secoisolariciresinol diglucoside: major precursor of mammalian lignans; structure given in first source; RN given refers to B-D-GLUCO isomer		2.1110
tachioside
tachioside: from the linseed meal; structure in first source		2.0810
lyoniside
lyoniside: see also eleutherosides & syringin for eleutheroside B: 118-34-3; RN given refers to (3beta)-isomer		1.9810
pinoresinol
pinoresinol: in plants; a furo[3,4-c]furan created from dimer of coniferyl alcohol. pinoresinol : A lignan that is tetrahydro-1H,3H-furo[3,4-c]furan substituted at positions 1 and 4 by 4-hydroxy-3-methoxyphenyl groups.		2.1110
deoxynivalenol-3-glucoside
deoxynivalenol-3-glucoside: a major conjugate of deoxynivalenol in beer and some brewing intermediates		2.1710trichothecene
deoxyguanosine
[no description available]		2.0810purine 2'-deoxyribonucleoside;
purines 2'-deoxy-D-ribonucleoside		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Infections, Nematode
[description not available]		01.9310
Ovine Diseases
[description not available]		01.9310
chemdatabank.com