linamarin profile

Linamarin is a cyanogenic glycoside found in various plants, including cassava, flax, and lima beans. It is synthesized in plants through a series of enzymatic reactions, starting with the amino acid valine. Linamarin is broken down by the enzyme linamarase, releasing hydrogen cyanide (HCN), a highly toxic compound, upon ingestion. HCN inhibits cellular respiration by interfering with the enzyme cytochrome c oxidase. Linamarin's toxicity is the reason cassava, a staple food in many tropical regions, needs to be properly processed before consumption to remove or reduce its content. Despite its toxicity, linamarin has been studied for potential medicinal properties, such as anti-inflammatory and anti-tumor effects. Research on linamarin aims to understand its biosynthesis, toxicity, and potential uses in medicine and agriculture.'

ID Source	ID
PubMed CID	11128
CHEMBL ID	3039425
CHEBI ID	16441
SCHEMBL ID	42021
MeSH ID	M0046418

Synonym
CHEBI:16441 ,
1-cyano-1-methylethyl beta-d-glucoside
2-(beta-d-glucopyranosyloxy)-2-methylpropanenitrile
DIVK1C_007032
SDCCGMLS-0066829.P001
SPECTRUM4_001668
SPECTRUM_001946
SPECTRUM5_000575
BSPBIO_003283
brn 0019237
alpha-hydroxyisobutyronitrile-beta-d-glucose
hsdb 3507
2-(beta-d-glucopyranosyloxy)isobutyronitrile
propanenitrile, 2-(beta-d-glucopyranosyloxy)-2-methyl-
phaseolunatin
554-35-8
linamarin ,
C01594
KBIO3_002503
KBIOGR_002195
KBIO2_007628
KBIO1_001976
KBIO2_002492
KBIOSS_002500
KBIO2_005060
SPBIO_002123
SPECTRUM3_001622
SPECPLUS_000936
SPECTRUM2_001972
SPECTRUM1504124
NCGC00178164-01
2-methyl-2-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropanenitrile
CCG-39428
unii-h3v9rp3wlo
5-17-07-00397 (beilstein handbook reference)
h3v9rp3wlo ,
CHEMBL3039425
SCHEMBL42021
2-(.beta.-d-glucopyranosyloxy)-2-methylpropanenitrile
linamarin [mi]
linamarin [hsdb]
DTXSID8052857
W-203090
alpha-hydroxyisobutyronitrile beta-d-glucopyranoside
2-methyl-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanenitrile
alpha-hydroxyisobutyronitrile beta-d-glucopyranoside, >=98.0% (hplc)
AKOS030242445
SR-05000002494-1
sr-05000002494
2-(beta-d-glucopyranosyloxy)-2-methyl-propanenitrile
manihotoxin
2-(b-d-glucopyranosyloxy)-2-methylpropanenitrile, 9ci
Q425157
2-beta-d-glucopyranosyloxy-2-methylpropanenitrile
2-methyl-2-((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yloxy)propanenitrile
linamarin min. 99%
CS-0081441
HY-123114
2-methyl-2-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)propanenitrile

Excerpt	Reference	Relevance
"Linamarin is a natural component of cassava tubers that can be destroyed before consumption by proper processing."	( Cassava cyanogens and fish mercury are high but safely consumed in the diet of native Amazonians. Dórea, JG, 2004)	1.04
"Linamarin is a natural cyanogenic glycoside that occurs in high concentrations in cassava."	( Developmental toxicity of the cyanogenic glycoside linamarin in the golden hamster. Frakes, RA; Sharma, RP; Willhite, CC, 1985)	1.24

Excerpt	Reference	Relevance
"Linamarin treatment had no effect on fetal body weight, ossification of fetal skeletons, embryonic mortality, or litter size."	( Developmental toxicity of the cyanogenic glycoside linamarin in the golden hamster. Frakes, RA; Sharma, RP; Willhite, CC, 1985)	1.24

Excerpt	Reference	Relevance
"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
" Cassava roots contain the toxic cyanogenic glucoside linamarin."	( The retail market for fresh cassava root tubers in the European Union (EU): the case of Copenhagen, Denmark--a chemical food safety issue? Brimer, L; Kolind-Hansen, L, 2010)	0.61
" 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
" RSO did not show any toxic potential to the rats."	( Rubber (Hevea brasiliensis) seed oil toxicity effect and Linamarin compound analysis. Abdullah, BM; Salih, N; Salimon, J, 2012)	0.62

Excerpt	Relevance	Reference
"Wistar rats, about 100 g in weight, were dosed by stomach tube with 30 mg of pure linamarin."	( Fate of orally dosed linamarin in the rat. Alexander, JC; Barrett, MD; Hill, DC; Zitnak, A, 1977)	0.8
" Blood cyanide concentrations following amygdalin treatment reached their highest level (130 nmol/ml) 1 hr after dosing and remained elevated until 3 hr after treatment."	( Comparative metabolism of linamarin and amygdalin in hamsters. Frakes, RA; Sharma, RP; Willhite, CC, 1986)	0.57
"3mL saline solution, IP) and 3 ACH groups (PubChem CID: 6406) dosed at 10, 15, and 20mM/24h for 28 days."	( Effects of acetone cyanohydrin, a derivative of cassava, on motor activity and kidney and liver function in Wistar rats. Díaz-Sobac, R; J Rosas-Jarquín, C; Rivadeneyra-Domínguez, E; Rodríguez-Landa, JF; Vázquez-Luna, A, 2019)	0.51

Class	Description
beta-D-glucoside	Any D-glucoside in which the anomeric centre has beta-configuration.
[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]

Pathway	Proteins	Compounds
linustatin bioactivation	0	10
linamarin degradation	2	10
superpathway of linamarin and lotaustralin biosynthesis	1	23
linamarin biosynthesis	1	15
linamarin degradation	2	15
linamarin biosynthesis	0	15
superpathway of linamarin and lotaustralin biosynthesis	0	23

Assay ID	Title	Year	Journal	Article
AID1159550	Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening	2015	Nature cell biology, Nov, Volume: 17, Issue:11	6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
AID977599	Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	2013	Molecular pharmacology, Jun, Volume: 83, Issue:6	Structure-based identification of OATP1B1/3 inhibitors.
AID977602	Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	2013	Molecular pharmacology, Jun, Volume: 83, Issue:6	Structure-based identification of OATP1B1/3 inhibitors.
AID1159607	Screen for inhibitors of RMI FANCM (MM2) intereaction	2016	Journal of biomolecular screening, Jul, Volume: 21, Issue:6	A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	20 (20.20)	18.7374
1990's	19 (19.19)	18.2507
2000's	21 (21.21)	29.6817
2010's	35 (35.35)	24.3611
2020's	4 (4.04)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	1 (0.93%)	5.53%
Reviews	8 (7.48%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	1 (0.93%)	0.25%
Other	97 (90.65%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	1.94	1	0	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
adenine [no description available]	2.04	1	0	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
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.	2.06	1	0	carbon 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
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	2.41	2	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
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	5.2	9	0	hydracid; one-carbon compound	Escherichia coli metabolite; human metabolite; poison
hydroxylamine amino alcohol : An alcohol containing an amino functional group in addition to the alcohol-defining hydroxy group.	1.98	1	0	hydroxylamines	algal metabolite; bacterial xenobiotic metabolite; EC 1.1.3.13 (alcohol oxidase) inhibitor; EC 4.2.1.22 (cystathionine beta-synthase) inhibitor; EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor; nitric oxide donor; nucleophilic reagent
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	1.98	1	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
thiamine thiamine(1+) : A primary alcohol that is 1,3-thiazol-3-ium substituted by (4-amino-2-methylpyrimidin-5-yl)methyl, methyl and 2-hydroxyethyl groups at positions 3, 4 and 5, respectively.	1.96	1	0	primary alcohol; vitamin B1	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
diethyl pyrocarbonate Diethyl Pyrocarbonate: Preservative for wines, soft drinks, and fruit juices and a gentle esterifying agent.. diethyl pyrocarbonate : The diethyl ester of dicarbonic acid.	1.98	1	0	acyclic carboxylic anhydride
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.	7.86	24	1	pseudohalide anion	EC 1.9.3.1 (cytochrome c oxidase) inhibitor
asparagine Asparagine: A non-essential amino acid that is involved in the metabolic control of cell functions in nerve and brain tissue. It is biosynthesized from ASPARTIC ACID and AMMONIA by asparagine synthetase. (From Concise Encyclopedia Biochemistry and Molecular Biology, 3rd ed). asparagine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 2-amino-2-oxoethyl group.	2.02	1	0	amino acid zwitterion; asparagine; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
histidine Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.	1.98	1	0	amino acid zwitterion; histidine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
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.	2.36	2	0	L-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.	2.36	2	0	aspartate 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
acetone cyanohydrin acetone cyanohydrin: RN given refers to unlabeled cpd; structure	2.52	2	0	cyanohydrin
sodium cyanide Sodium Cyanide: A highly poisonous compound that is an inhibitor of many metabolic processes and is used as a test reagent for the function of chemoreceptors. It is also used in many industrial processes.. sodium cyanide : A cyanide salt containing equal numbers of sodium cations and cyanide anions.	1.99	1	0	cyanide salt; one-carbon compound; sodium salt	EC 1.15.1.1 (superoxide dismutase) inhibitor
1,2-dihydroxybenzene-3,5-disulfonic acid disodium salt 1,2-Dihydroxybenzene-3,5-Disulfonic Acid Disodium Salt: A colorimetric reagent for iron, manganese, titanium, molybdenum, and complexes of zirconium. (From Merck Index, 11th ed)	2.04	1	0	organic molecular entity
potassium cyanide [no description available]	2.67	3	0	cyanide salt; one-carbon compound; potassium salt	EC 1.15.1.1 (superoxide dismutase) inhibitor; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; neurotoxin
isoxazoles Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.	1.98	1	0	isoxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiocyanate thiocyanate: RN given refers to parent cpd. thiocyanate : A pseudohalide anion obtained by deprotonation of the thiol group of thiocyanic acid.	11.71	10	1	pseudohalide anion; sulfur molecular entity	human metabolite
cyanogen cyanogen: structure. oxalonitrile : A dinitrile that is ethane substituted by two cyano groups.	9.75	9	0	dinitrile; pseudohalogen
luminol Luminol: 5-Amino-2,3-dihydro-1,4-phthalazinedione. Substance that emits light on oxidation. It is used in chemical determinations.	2	1	0
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	2.04	1	0	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
2'-deoxyadenosine 2'-deoxyformycin A: RN not in Chemline 9/85; RN and structure given in first source	2.08	1	0	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
silver Silver: An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.	1.96	1	0	copper group element atom; elemental silver	Escherichia coli metabolite
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.	6.97	31	0	D-glucopyranose	epitope; mouse metabolite
n-ethyl-5-phenylisoxazolium-3'-sulfonate N-ethyl-5-phenylisoxazolium-3'-sulfonate: reagent for rapid modification of carboxyl groups in proteins; structure	1.98	1	0
4-nitrophenyl beta-d-glucoside 4-nitrophenyl beta-D-glucoside: RN given refers to (beta)-anomer; see also (alpha)-anomer: 3767-28-0; cpd with unspecified anomer: 5779-46-4. 4-nitrophenyl beta-D-glucoside : A beta-D-glucoside that is beta-D-glucopyranose in which the anomeric hydroxy hydrogen is replaced by a 4-nitrophenyl group.	2.03	1	0	beta-D-glucoside; C-nitro compound	chromogenic compound
cyanates Cyanates: Organic salts of cyanic acid containing the -OCN radical.. cyanates : Salts and esters of cyanic acid, HOC#N; compounds carrying the cyanate functional group -O-C#N.. isocyanates : Organonitrogen compounds that are derivatives of isocyanic acid; compounds containing the isocyanate functional group -N=C=O (as opposed to the cyanate group, -O-C#N).	2.06	1	0
prunasin prunasin: cyanogenic glycoside; RN given refers to cpd without isomeric designation	2.37	2	0	prunasin
linustatin linustatin: cyanogenic glucoside from linseed oil; structure	2.74	3	0	cyanogenic glycoside
neolinustatin neolinustatin: cyanogenic glucoside from linseed oil; related to amygdalin; structure	2.43	2	0	cyanogenic glycoside
carbodiimides Carbodiimides: Compounds with the general formula RN=C=NR, where R is a hydrocarbyl group.. methanediimine : A carbodiimide in which both nitrogens are unsubstituted.	1.98	1	0	carbodiimide
scopolin [no description available]	3.56	2	0	beta-D-glucoside; coumarins; monosaccharide derivative	plant metabolite
lotaustralin lotaustralin: higher homologue of linamarin from flax; a cyanogenic glycoside; RN given refers to (R)-isomer; structure	6.06	22	0	cyanogenic glycoside
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)	2.51	2	0
gamma-sitosterol clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.	2.05	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols	marine metabolite; plant metabolite
sodium cyanate sodium cyanate: used in treatment of sickle cell anemia; RN given refers to cyanic acid, Na salt	2.06	1	0	cyanate salt; one-carbon compound
glycosides [no description available]	7.03	25	1
amygdalin [no description available]	8.41	7	0
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	2.05	1	0
scopoletin [no description available]	3.56	2	0	hydroxycoumarin	plant growth regulator; plant metabolite
beta carotene beta Carotene: A carotenoid that is a precursor of VITAMIN A. Beta carotene is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (PORPHYRIA, ERYTHROPOIETIC).. provitamin A : A provitamin that can be converted into vitamin A by enzymes from animal tissues.	2.05	1	0	carotenoid beta-end derivative; cyclic carotene	antioxidant; biological pigment; cofactor; ferroptosis inhibitor; human metabolite; mouse metabolite; plant metabolite; provitamin A
esculetin esculetin: used in filters for absorption of ultraviolet light; structure. esculetin : A hydroxycoumarin that is umbelliferone in which the hydrogen at position 6 is substituted by a hydroxy group. It is used in filters for absorption of ultraviolet light.	3.56	2	0	hydroxycoumarin	antioxidant; plant metabolite; ultraviolet filter
esculin [no description available]	2.05	1	0	beta-D-glucoside; hydroxycoumarin	antioxidant; metabolite
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.	2.11	1	0	macrolide; resorcinols	fungal metabolite; mycoestrogen
cytochalasin b Cytochalasin B: A cytotoxic member of the CYTOCHALASINS.. cytochalasin B : An organic heterotricyclic compound, that is a mycotoxin which is cell permeable an an inhibitor of cytoplasmic division by blocking the formation of contractile microfilaments.	2.01	1	0	cytochalasin; lactam; lactone; organic heterotricyclic compound	actin polymerisation inhibitor; metabolite; mycotoxin; platelet aggregation inhibitor
corrin corrin : A tetrapyrrole fundamental parent that is the core macrocycle of vitamin B12.	2.05	1	0
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.	7.02	1	0	aliphatic nitrile; beta-D-glucoside; cyanogenic glycoside; monosaccharide derivative	anti-allergic agent; metabolite
mocetinostat mocetinostat: undergoing phase II clinical trials for treatment of cancer. mocetinostat : A benzamide obtained by formal condensation of the carboxy group of 4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid with one of the amino groups of benzene-1,2-diamine. It is an orally active and isotype-selective HDAC inhibitor which exhibits antitumour activity (IC50 = 0.15, 0.29, 1.66 and 0.59 muM for HDAC1, HDAC2, HDAC3 and HDAC11).	2	1	0	aminopyrimidine; benzamides; pyridines; secondary amino compound; secondary carboxamide; substituted aniline	antineoplastic agent; apoptosis inducer; autophagy inducer; cardioprotective agent; EC 3.5.1.98 (histone deacetylase) inhibitor; hepatotoxic agent
secoisolariciresinol diglucoside secoisolariciresinol diglucoside: major precursor of mammalian lignans; structure given in first source; RN given refers to B-D-GLUCO isomer	2.13	1	0
tachioside tachioside: from the linseed meal; structure in first source	2.08	1	0
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	3.56	2	0	benzenes; hydroxycoumarin; methyl ketone
deoxyguanosine [no description available]	2.08	1	0	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
3-methyladenine N3-methyladenine: structure in first source	2.04	1	0

Condition	Relationship Strength	Studies
Benign Neoplasms [description not available]	3.67	3
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	3.67	3
Anemia, Fanconi [description not available]	2.13	1
Fanconi Anemia Congenital disorder affecting all bone marrow elements, resulting in ANEMIA; LEUKOPENIA; and THROMBOPENIA, and associated with cardiac, renal, and limb malformations as well as dermal pigmentary changes. Spontaneous CHROMOSOME BREAKAGE is a feature of this disease along with predisposition to LEUKEMIA. There are at least 7 complementation groups in Fanconi anemia: FANCA, FANCB, FANCC, FANCD1, FANCD2, FANCE, FANCF, FANCG, and FANCL. (from Online Mendelian Inheritance in Man, http://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=227650, August 20, 2004)	2.13	1
Diathesis [description not available]	2.31	1
Anterior Horn Cell Disease [description not available]	4.09	5
Motor Neuron Disease Diseases characterized by a selective degeneration of the motor neurons of the spinal cord, brainstem, or motor cortex. Clinical subtypes are distinguished by the major site of degeneration. In AMYOTROPHIC LATERAL SCLEROSIS there is involvement of upper, lower, and brainstem motor neurons. In progressive muscular atrophy and related syndromes (see MUSCULAR ATROPHY, SPINAL) the motor neurons in the spinal cord are primarily affected. With progressive bulbar palsy (BULBAR PALSY, PROGRESSIVE), the initial degeneration occurs in the brainstem. In primary lateral sclerosis, the cortical neurons are affected in isolation. (Adams et al., Principles of Neurology, 6th ed, p1089)	4.09	5
Nervous System Disorders [description not available]	3.62	3
Nervous System Diseases Diseases of the central and peripheral nervous system. This includes disorders of the brain, spinal cord, cranial nerves, peripheral nerves, nerve roots, autonomic nervous system, neuromuscular junction, and muscle.	3.62	3
Dyskinesia, Medication-Induced [description not available]	2.13	1
Dyskinesia, Drug-Induced Abnormal movements, including HYPERKINESIS; HYPOKINESIA; TREMOR; and DYSTONIA, associated with the use of certain medications or drugs. Muscles of the face, trunk, neck, and extremities are most commonly affected. Tardive dyskinesia refers to abnormal hyperkinetic movements of the muscles of the face, tongue, and neck associated with the use of neuroleptic agents (see ANTIPSYCHOTIC AGENTS). (Adams et al., Principles of Neurology, 6th ed, p1199)	2.13	1
Benign Neoplasms, Brain [description not available]	2.94	4
Cell Transformation, Neoplastic Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.	2.04	1
Astrocytoma, Grade IV [description not available]	2.42	2
Brain Neoplasms Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.	2.94	4
Glioblastoma A malignant form of astrocytoma histologically characterized by pleomorphism of cells, nuclear atypia, microhemorrhage, and necrosis. They may arise in any region of the central nervous system, with a predilection for the cerebral hemispheres, basal ganglia, and commissural pathways. Clinical presentation most frequently occurs in the fifth or sixth decade of life with focal neurologic signs or seizures.	2.42	2
Adenovirus Infections [description not available]	2.05	1
Hepatocellular Carcinoma [description not available]	2.45	2
Experimental Hepatoma [description not available]	2.05	1
Adenoviridae Infections Virus diseases caused by the ADENOVIRIDAE.	2.05	1
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	2.45	2
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	2.05	1
Disease Exacerbation [description not available]	2.06	1
Encephalopathy, Toxic [description not available]	2.98	1
Lower Extremity Weakness, Spastic [description not available]	3.35	2
Ataxia Impairment of the ability to perform smoothly coordinated voluntary movements. This condition may affect the limbs, trunk, eyes, pharynx, larynx, and other structures. Ataxia may result from impaired sensory or motor function. Sensory ataxia may result from posterior column injury or PERIPHERAL NERVE DISEASES. Motor ataxia may be associated with CEREBELLAR DISEASES; CEREBRAL CORTEX diseases; THALAMIC DISEASES; BASAL GANGLIA DISEASES; injury to the RED NUCLEUS; and other conditions.	2.98	1
Cochlear Hearing Loss [description not available]	2.98	1
Polyneuropathy, Acquired [description not available]	2.98	1
Deficiency, Thiamine [description not available]	3.32	2
Hearing Loss, Sensorineural Hearing loss resulting from damage to the COCHLEA and the sensorineural elements which lie internally beyond the oval and round windows. These elements include the AUDITORY NERVE and its connections in the BRAINSTEM.	2.98	1
Optic Atrophy Atrophy of the optic disk which may be congenital or acquired. This condition indicates a deficiency in the number of nerve fibers which arise in the RETINA and converge to form the OPTIC DISK; OPTIC NERVE; OPTIC CHIASM; and optic tracts. GLAUCOMA; ISCHEMIA; inflammation, a chronic elevation of intracranial pressure, toxins, optic nerve compression, and inherited conditions (see OPTIC ATROPHIES, HEREDITARY) are relatively common causes of this condition.	2.98	1
Polyneuropathies Diseases of multiple peripheral nerves simultaneously. Polyneuropathies usually are characterized by symmetrical, bilateral distal motor and sensory impairment with a graded increase in severity distally. The pathological processes affecting peripheral nerves include degeneration of the axon, myelin or both. The various forms of polyneuropathy are categorized by the type of nerve affected (e.g., sensory, motor, or autonomic), by the distribution of nerve injury (e.g., distal vs. proximal), by nerve component primarily affected (e.g., demyelinating vs. axonal), by etiology, or by pattern of inheritance.	2.98	1
Thiamine Deficiency A nutritional condition produced by a deficiency of THIAMINE in the diet, characterized by anorexia, irritability, and weight loss. Later, patients experience weakness, peripheral neuropathy, headache, and tachycardia. In addition to being caused by a poor diet, thiamine deficiency in the United States most commonly occurs as a result of alcoholism, since ethanol interferes with thiamine absorption. In countries relying on polished rice as a dietary staple, BERIBERI prevalence is very high. (From Cecil Textbook of Medicine, 19th ed, p1171)	3.32	2
Glial Cell Tumors [description not available]	2.46	2
Glioma Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)	7.46	2
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.39	2
Cancer of Liver [description not available]	2.04	1
Liver Neoplasms Tumors or cancer of the LIVER.	2.04	1
Anoxemia [description not available]	2.9	1
Bleeding [description not available]	2.9	1
Insulin Sensitivity [description not available]	2.9	1
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	2.9	1
Diabetes Mellitus A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.	2.9	1
Hemorrhage Bleeding or escape of blood from a vessel.	2.9	1
Insulin Resistance Diminished effectiveness of INSULIN in lowering blood sugar levels: requiring the use of 200 units or more of insulin per day to prevent HYPERGLYCEMIA or KETOSIS.	2.9	1
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	2.9	1
Central Hypothyroidism [description not available]	1.98	1
Hypothyroidism A syndrome that results from abnormally low secretion of THYROID HORMONES from the THYROID GLAND, leading to a decrease in BASAL METABOLIC RATE. In its most severe form, there is accumulation of MUCOPOLYSACCHARIDES in the SKIN and EDEMA, known as MYXEDEMA. It may be primary or secondary due to other pituitary disease, or hypothalamic dysfunction.	1.98	1
Proteinuria The presence of proteins in the urine, an indicator of KIDNEY DISEASES.	1.98	1
Abnormal Deep Tendon Reflex [description not available]	2	1
Familial Spastic Paraparesis, Htlv-1-Associated [description not available]	2	1
Reflex, Abnormal An abnormal response to a stimulus applied to the sensory components of the nervous system. This may take the form of increased, decreased, or absent reflexes.	2	1
Paraparesis, Tropical Spastic A subacute paralytic myeloneuropathy occurring endemically in tropical areas such as the Caribbean, Colombia, India, and Africa, as well as in the southwestern region of Japan; associated with infection by HUMAN T-CELL LEUKEMIA VIRUS I. Clinical manifestations include a slowly progressive spastic weakness of the legs, increased reflexes, Babinski signs, incontinence, and loss of vibratory and position sensation. On pathologic examination inflammatory, demyelination, and necrotic lesions may be found in the spinal cord. (Adams et al., Principles of Neurology, 6th ed, p1239)	2	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2	1
Alloxan Diabetes [description not available]	2	1
Diabetic Glomerulosclerosis [description not available]	2	1
Weight Reduction [description not available]	2	1
Diabetic Nephropathies KIDNEY injuries associated with diabetes mellitus and affecting KIDNEY GLOMERULUS; ARTERIOLES; KIDNEY TUBULES; and the interstitium. Clinical signs include persistent PROTEINURIA, from microalbuminuria progressing to ALBUMINURIA of greater than 300 mg/24 h, leading to reduced GLOMERULAR FILTRATION RATE and END-STAGE RENAL DISEASE.	2	1
Weight Loss Decrease in existing BODY WEIGHT.	2	1
Arrhythmia [description not available]	1.97	1
Arrhythmias, Cardiac Any disturbances of the normal rhythmic beating of the heart or MYOCARDIAL CONTRACTION. Cardiac arrhythmias can be classified by the abnormalities in HEART RATE, disorders of electrical impulse generation, or impulse conduction.	1.97	1
Acquired Encephalocele [description not available]	1.96	1
Complications, Pregnancy [description not available]	1.96	1
Abnormalities, Drug-Induced Congenital abnormalities caused by medicinal substances or drugs of abuse given to or taken by the mother, or to which she is inadvertently exposed during the manufacture of such substances. The concept excludes abnormalities resulting from exposure to non-medicinal chemicals in the environment.	1.96	1
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	1.96	1

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