melamine profile

Melamine is a synthetic organic compound with the formula C3H6N6. It is a white, crystalline, organic base. Melamine is a trimer of cyanamide, and it is produced by the trimerization of cyanamide in the presence of a catalyst, such as ammonia. Melamine is used to produce melamine resins, which are strong, rigid, and resistant to heat and chemicals. Melamine resins are used in a wide variety of applications, including laminates, adhesives, molding compounds, and fire retardants. Melamine is also used to produce melamine-formaldehyde (MF) resins, which are used in a variety of consumer products, such as kitchen countertops, dinnerware, and floor tiles. Melamine is a non-toxic compound, but it can be harmful if ingested in large quantities. Melamine is studied because it is an important industrial chemical, and because it is used in a variety of consumer products. Research on melamine is focused on understanding its properties, its potential health risks, and its applications in different industries.'

melamine: RN given refers to parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

melamine : A trimer of cyanamide, with a 1,3,5-triazine skeleton. [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]

ID Source	ID
PubMed CID	7955
CHEMBL ID	1231106
CHEBI ID	27915
SCHEMBL ID	12192199
SCHEMBL ID	25853
MeSH ID	M0058547

Synonym
BIDD:ER0287
AKOS005448714
ax2 ,
CHEMBL1231106
1,5-triazine-2,4,6-triamine
nci-c50715
teoharn
2,6-triaminotriazine
isomelamine
2,6-triamino-s-triazine
s-triazinetriamine
cyanuramide
s-triazine,4,6-triamino-
cymel
cyanurotriamide
cyanurotriamine
1,5-triazine-2,4,6(1h,3h,5h)-triimine
2,6-triamino-1,3,5-triazine
hicophor pr
nsc2130
theoharn
virset 656-4
nsc-2130
wln: t6n cn enj bz dz fz
sym-triaminotriazine
CHEBI:27915 ,
triaminotriazine
cyanuric triamide
2,4,6-triamino-s-triazine
s-triaminotriazine
1,3,5-triazine-2,4,6(1h,3h,5h)triimine
aero
2,4,6-triamino sym-triazine
2,4,6-triaminotriazine
nsc8152
5432-64-4
nsc-8152
1,3,5-triazine-2,4,6-triamine
mark zs 27
dg 002
einecs 203-615-4
dg 002 (amine)
brn 0124341
pluragard
s-triazine, 2,4,6-triamino-
adk stab zs 27
spinflam ml 94m
nsc 2130
pluragard c 133
hsdb 2648
ai3-14883
1,3,5-triazine-2,4,6(1h,3h,5h)-triimine
ccris 373
zs 27
yukamelamine
C08737
2,4,6-triamino-1,3,5-triazine
108-78-1
melamine
melamine, 99%
NCGC00164014-01
STK378738
melamine-13c3,15n3
2,4,6-triamino-1,3,5-triazine monomer
melamine monomer
T0337
NCGC00164014-02
BBL000010
4-26-00-01253 (beilstein handbook reference)
unii-n3gp2ysd88
ec 203-615-4
n3gp2ysd88 ,
NCGC00258057-01
dtxsid6020802 ,
tox21_200503
dtxcid40802
cas-108-78-1
SCHEMBL12192199
S9212
FT-0670983
FT-0670982
FT-0609833
metformin hydrochloride impurity d [ep impurity]
melamine [usp-rs]
melamine [mi]
melamine [iarc]
melamine [hsdb]
melamine [inci]
melamin
[1,3,5]triazine-2,4,6-triamine
SCHEMBL25853
AC-34715
s-triazine, 4,6-diamino-1,2-dihydro-2-imino-
cymel (salt/mix)
cyanurtriamide
1246816-14-7
1,3,5-triazinane-2,4,6-triimine
J-002191
triamino-s-triazine
mfcd00006055
melamine, >=95.0% (hplc), pharmaceutical impurity standard
melamine, united states pharmacopeia (usp) reference standard
melamine, analytical standard
1,3,5-triazine-2,4,6-triamine monomer
melamine, pharmaceutical secondary standard; certified reference material
1,3,5-triazine-2,4,6-triamine; metformin hydrochloride imp. d (ep); melamine; metformin imp. d (ep); metformin hydrochloride impurity d; metformin impurity d
melamine 1.0 mg/ml in dimethyl sulfoxide
1,3,5-triazine-2,4,6-triamine (melamine)
1,3, 5-triazine-2,4,6-triamine
4,6-diamino-1,2-dihydro-2-imino-s-triazine
2,4, 6-triamino-1,3,5-triazine
1,3,5-triazine-2,4,6-triamine (acd/name 4.0)
E76265
VS-00405
metformin ep impurity d
melamine; 1,3,5-triazine-2,4,6-triamine
melamine 100 microg/ml in acetonitrile/water
Q212553
2,4,6-triamino-1,3,5-triazine;melamine;1,3,5-triazine-2,4,6-triamine;[1,3,5]triazine-2,4,6-triamine;s-triazine, 4,6-diamino-1,2-dihydro-2-imino-;2,4,6-triamino-1,3,5-triazine melamine 1,3,5-triazine-2,4,6-triamine [1,3,5]triazine-2,4,6-triamine s-triazine
CCG-266105
HY-Y1117
CS-0016866
melamine 100 microg/ml in water
2,4,6-triamino-1,3,5-triazine, sym-triaminotriazine
EN300-71605
Z1142688822
metformin hydrochloride impurity d (ep impurity)
melamine (iarc)
cyanurtriamine
melamine (usp-rs)
ma-1-h2o

Research Excerpts

Overview

Melamine is a nitrogenous organic compound containing high amounts of nitrogen, which is interpreted as high protein in various standard protein measuring tests. It is a weak fluorescent substance, it is difficult to detect melamine directly by fluorescence spectroscopy.

Excerpt	Reference	Relevance
"Melamine foam (MF) is a widely used commercial product and exhibits wide applications in many fields ranging from building, transportation to daily chemical product. "	( Polydopamine-assisted polyethylenimine grafting melamine foam and the application in wastewater purification. Cao, S; Huang, T; Lei, YZ; Luo, D; Wang, Y; Zhang, N, 2022)	2.42
"Melamine is an important chemical raw material used in industries, which has potential health risks to animals and humans. "	( Melamine induced changes in histopathology of the main organs and transcriptional levels of MAPK signaling genes in kidneys of female mice. Chen, S; Liang, C; Ren, C; Tian, X; Wang, J; Yang, W; Zhang, J; Zhang, X, 2022)	3.61
"Melamine is a nephrotoxic industrial chemical. "	( Associations of Dietary Intake with Urinary Melamine and Derivative Concentrations among Children in the GAPPS Cohort. Day, DB; de Boer, IH; Flynn, JT; Fretts, AM; Kannan, K; Melough, MM; Sathyanarayana, S; Wang, S; Zhu, H, 2022)	2.43
"Melamine contamination is a recent public health problem emerging globally. "	( Presence of melamine in human milk and the evaluation of the effects on mother-infant pairs in a cohort study. Güneş, B; Yalçin, S; Yalçin, SS, 2020)	2.38
"Melamine (ML) is a common food adulterant and contaminant. "	( Prevention of melamine-induced hepatorenal impairment by an ethanolic extract of Moringa oleifera: Changes in KIM-1, TIMP-1, oxidative stress, apoptosis, and inflammation-related genes. Abd-Elhakim, YM; Ali, HA; El Bohi, KM; Mahmoud, FA; Mohamed, WAM; Saber, TM, 2021)	2.42
"Melamine is a nitrogenous organic compound containing high amounts of nitrogen, which is interpreted as high protein in various standard protein measuring tests, therefore added to foods to boost the protein content. "	( Melamine contamination and associated health risks: Gut microbiota does make a difference. Bhattacharya, R; Gupta, S; Rajpoot, M; Sharma, AK; Sharma, S; Sharma, V, 2021)	3.51
"Melamine is a high-production-volume chemical and a kidney toxicant. "	( Dietary Sources of Melamine Exposure among US Children and Adults in the National Health and Nutrition Examination Survey 2003-2004. Foster, D; Melough, MM; Sathyanarayana, S, 2020)	2.33
"As melamine is a weak fluorescent substance, it is difficult to detect melamine directly by fluorescence spectroscopy."	( A Lanthanide Complex Fluorescent Probe for the Detection of Melamine. Chen, G; Gao, H; Gu, J; Guo, S; Li, L; Li, X; Ma, C; Wang, G; Wang, Z; Wei, Y; Wu, Y; Zhu, C, 2021)	1.38
"Melamine is a compound commonly used in the manufacturing of plastic and flame retardant products, but due to its solubility on water and high nitrogen content, it is also used to adulterate milk to mask adulteration by dilution in protein content tests. "	( Determination of melamine in milk by fluorescence spectroscopy and second-order calibration. Barreto, MC; Braga, RG; Fragoso, WD; Lemos, SG, 2021)	2.4
"Melamine is a chemical substance used as a food adulterant because of its high nitrogen content; it is known to induce neurotoxicity, thereby adversely affecting the central nervous system. "	( The ameliorative effect of nanoselenium on histopathological and biochemical alterations induced by melamine toxicity on the brain of adult male albino rats. Abou-El-Sherbini, KS; Ahmed, YH; Bashir, DW; Drweesh, EA; El-Leithy, EMM; Elzahany, EAM; Rashad, MM, 2021)	2.28
"Melamine is a nitrogen-containing heterocyclic organic compound with a triazine skeleton, which has been widely applied in industrial and chemical fields. "	( Reproductive toxicity of melamine against male mice and the related mechanism. Huang, J; Xia, F; Yang, G; Zhang, S, 2018)	2.23
"Melamine (MEL) is a widespread food contaminant and adulterant. "	( Palliative effects of Moringa olifera ethanolic extract on hemato-immunologic impacts of melamine in rats. Abd-Elhakim, YM; Abd-Elmotal, SM; El Bohi, KM; El Sayed, S; Hassan, SK, 2018)	2.15
"Melamine is a nitrogen-containing organic compound that is used in a wide range of products, including paints, plastics, and paper, as a flame retardant. "	( Melamine and its derivatives in dog and cat urine: An exposure assessment study. Bollapragada, R; Kannan, K; Karthikraj, R, 2018)	3.37
"Melamine is a nitrogen-rich (67% nitrogen by mass) heterocyclic aromatic compound that could significantly increase effluent total nitrogen concentrations. "	( Fate and toxicity of melamine in activated sludge treatment systems after a long-term sludge adaptation. Bernards, M; Hu, Z; Sims, A; Xu, S; Zhang, Y, 2013)	2.15
"Melamine is a wildly used compound in manufactures of plastics and resins. "	( Melamine activates NFκB/COX-2/PGE2 pathway and increases NADPH oxidase-dependent ROS production in macrophages and human embryonic kidney cells. Kuo, FC; Lo, YC; Tseng, YT; Wu, MT; Wu, SR, 2013)	3.28
"Melamine is a nitrogenous chemical substance used principally as a starting material for the manufacture of synthetic resins. "	( Rapid detection of melamine adulteration in dairy milk by SB-ATR-Fourier transform infrared spectroscopy. Jawaid, S; Khaskheli, AA; Nizamani, SM; Sherazi, ST; Talpur, FN, 2013)	2.16
"Melamine is thought to be an endocrine disrupter that affects physiology in cells. "	( Effect of melamine on [Ca(2+)]i and viability in PC3 human prostate cancer cells. Chang, HT; Chen, FA; Cheng, JS; Chou, CT; Jan, CR; Kuo, CC; Kuo, DH; Liang, WZ; Shieh, P; Sun, TK; Tseng, HW; Wang, JL; Yu, CC, 2014)	2.25
"Melamine is an organic nitrogenous compound whose acute toxicity was generally thought to be low in animals. "	( The toxic effects of melamine on spleen lymphocytes with or without cyanuric acid in mice. Bai, WL; Han, J; Han, XH; Han, XR; He, JB; Li, HS; Liu, BS; Liu, J; Wang, WC; Wang, X; Yin, RH; Yin, RL, 2014)	2.16
"Melamine is a raw material in the chemical industry. "	( Effect of melamine toxicity on Tetrahymena thermophila proliferation and metallothionein expression. Li, H; Li, W; Tian, X; Zhang, J, 2015)	2.26
"Melamine is a chemical compound that is widely used during the manufacture of amino resins and plastics. "	( Melamine negatively affects oocyte architecture, oocyte development and fertility in mice. Dai, XX; Duan, X; Liu, HL; Sun, SC; Wang, T, 2015)	3.3
"Melamine is an industrial chemical that can cause central nervous system disorders including excitotoxicity and cognitive impairment. "	( Melamine Alters Glutamatergic Synaptic Transmission of CA3-CA1 Synapses Presynaptically Through Autophagy Activation in the Rat Hippocampus. Wang, H; Xiao, X; Zhang, H; Zhang, T, 2016)	3.32
"Melamine is a nitrogen heterocyclic triazine compound which is widely used as an industrial chemical. "	( Melamine Induces Oxidative Stress in Mouse Ovary. Cui, XS; Dai, XX; Duan, X; Kim, NH; Sun, SC; Xiong, B, 2015)	3.3
"Melamine is a heterocyclic, aromatic amine and nitrogen-enriched environmental toxicant, found in not only adulterated foodstuffs but also industrial household tableware and paints. "	( Adverse reproductive effects of maternal low-dose melamine exposure during pregnancy in rats. Chu, CY; Fung, KP; Li, L; Shum, AS; Tang, LY; Wang, CC, 2017)	2.15
"Melamine is an organic nitrogenous compound widely used as an industrial chemical, and it has been recently reported by us that melamine has a toxic effect on the female reproductive system in mice, and renders females subfertile; the molecular basis, however, has not been adequately assessed. "	( Melamine Impairs Female Fertility via Suppressing Protein Level of Juno in Mouse Eggs. Dai, X; Lu, Y; Miao, Y; Sun, S; Xiong, B; Zhang, M; Zhou, C, 2015)	3.3
"Melamine is an industrial chemical with high nitrogen content. "	( The effects of melamine on humoral immunity with or without cyanuric acid in mice. Bai, WL; Dong, Q; Han, XH; He, JB; Li, HS; Li, XT; Liu, BS; Liu, J; Wang, WC; Wang, X; Yin, RH; Yin, RL; Yuan, J, 2016)	2.23
"Melamine is a synthetic chemical used in the manufacture of resins, pigments, and superplasticizers. "	( A Review of Methods for Detecting Melamine in Food Samples. Lee, NA; Li, M; Liu, G; Lu, Y; Pan, M; Wang, S; Xia, Y, 2017)	2.18
"Melamine (MA) is a significant raw material for industry and home furnishing, and an intermediate for pharmacy. "	( The behavior of melamine in biological wastewater treatment system. An, H; Chen, F; Li, X; Wang, D; Xie, T; Xu, Q; Yang, Q; Yuan, Y; Zeng, G; Zhao, J; Zhong, Y, 2017)	2.24
"Melamine is a noxious nitrogen-rich substance and has been illegally adulterated in milk to boost the protein content. "	( Detection of melamine adulteration in milk by near-infrared spectroscopy and one-class partial least squares. Chen, H; Lin, Z; Tan, C; Wu, T, 2017)	2.27
"Melamine is a nitrogenous compound added to milk for mimicking proteins, consumption of which leads to kidney stones and renal failures."	( Rapid sensing of melamine in milk by interference green synthesis of silver nanoparticles. Gorthi, SS; Kiruba Daniel, SCG; Varun, S, 2017)	1.52
"Melamine is an industrial chemical used primarily as plastics stabilizer and fire retardant. "	( Melamine-contaminated milk products induced urinary tract calculi in children. Liu, AM; Wang, YP; Wu, LL; Zhang, L; Zhao, ZY; Zou, CC, 2009)	3.24
"Melamine is an organic nitrogenous compound used in the production of plastics, dyes, fertilizers, and fabrics."	( Melamine toxicity and the kidney. Hau, AK; Kwan, TH; Li, PK, 2009)	2.52
"Melamine intoxication is a present focus in global public health. "	( Energy fluctuation in the formation of melamine cyanurate reaction: a factor leading to acute renal failure in melamine toxicity. Wiwanitkit, V, 2009)	2.06
"Melamine is a chemical product that was sporadically mixed into animal feeds to boost protein content. "	( Screening and determination of melamine residues in tissue and body fluid samples. Gong, L; He, P; Li, Z; Ma, X; Wang, Z; Yang, W; Zhang, L, 2010)	2.09
"Melamine is a widely used industrial chemical not considered acutely toxic with a high LD(50) in animals."	( Melamine toxicity. Osterloh, JD; Skinner, CG; Thomas, JD, 2010)	2.52
"Melamine is a toxic triazine, illegally used as an additive in milk to apparently increase the amount of protein. "	( Development of an analytical methodology to quantify melamine in milk using micellar liquid chromatography and validation according to EU Regulation 2002/654/EC. Beltrán-Martinavarro, B; Esteve-Romero, J; Marco-Peiró, S; Peris-Vicente, J; Rambla-Alegre, M, 2010)	2.05
"Melamine is a widely-used chemical in industries. "	( Hemolysis of human erythrocytes induced by melamine-cyanurate complex. He, F; Huang, B; Qin, X; Wang, C; Zeng, C, 2010)	2.07
"Melamine is a category III carcinogen. "	( Melamine induces sperm DNA damage and abnormality, but not genetic toxicity. Li, JT; Li, WX; Yang, GY; Zhang, B; Zhang, QX; Zhu, W, 2011)	3.25
"Melamine is a nitrogen-rich industrial chemical which is occasionally used to increase the apparent protein content of different products destined for human and animal consumption. "	( Use of micellar mobile phases for the chromatographic determination of melamine in dietetic supplements. Beltrán-Martinavarro, B; Carda-Broch, S; Esteve-Romero, J; Marco-Peiró, S; Peris-Vicente, J; Rambla-Alegre, M, 2012)	2.05
"Melamine is an important and widely used organic industrial chemical. "	( Repeat oral dose toxicity studies of melamine in rats and monkeys. Early, RJ; Guo, L; He, B; Hu, E; Huang, H; Jiang, Y; Kong, Q; Mu, XP; Xu, H; Yang, X; Yu, H; Zhou, J, 2013)	2.11
"The melamine resin is a polymer of a hexamethylol melamine ether which can coat glass slides with an electron-transparent foil (approximately 80 nm thick) after polymerization by p-toluene sulphonic acid and warming. "	( A new technical approach for the ultrastructural analysis of hematopoietic cells using cell monolayers adherent to electron-transparent melamine resins. Beyer-Johannböke, E; Ganser, A; Gunsilius, E; Hartl, M; Heil, G; Krauter, J; Kurrle, E; Westphal-Frösch, C, 1993)	1.05

Effects

Melamine may have been an important prebiotic information carrier, but its excited-state dynamics, which determine its stability under UV radiation, have never been characterized. Melamine has become the focus of attention for the possible occurrence of nephrolithiasis and associated deaths.

Excerpt	Reference	Relevance
"Melamine, which has a multi-nitrogen heterocyclic ring, is prone to coordinate with Hg(2+)."	( Label-free turn-on fluorescent detection of melamine based on the anti-quenching ability of Hg 2+ to gold nanoclusters. Dai, H; Hu, J; Li, Z; Ni, P; Shi, Y; Sun, Y; Wang, Y, 2014)	1.38
"Melamine has received increasing public attention as a persistent, mobile and toxic (PMT) substance. "	( In situ measurement of an emerging persistent, mobile and toxic (PMT) substance - Melamine and related triazines in waters by diffusive gradient in thin-films. Cai, QS; Chen, CE; Cheng, S; Li, C; Liu, SS; Sweetman, AJ; Wang, Z; Yang, Y; Ying, GG, 2021)	2.29
"Melamine contamination has remained pervasive in the environment even after the 2008 toxic milk scandal. "	( Interrelationship of environmental melamine exposure, biomarkers of oxidative stress and early kidney injury. Chien, TM; Chou, YH; Hsieh, TJ; Huang, SP; Huang, TY; Lee, CH; Lee, YC; Li, CC; Liu, CC; Tsai, YC; Wen, SC; Wu, CF; Wu, MT; Wu, WJ, 2020)	2.28
"Melamine has been illegally adulterated in dairy food because of the rich nitrogen content and stable chemical properties in recent years. "	( A Lanthanide Complex Fluorescent Probe for the Detection of Melamine. Chen, G; Gao, H; Gu, J; Guo, S; Li, L; Li, X; Ma, C; Wang, G; Wang, Z; Wei, Y; Wu, Y; Zhu, C, 2021)	2.31
"Melamine toxicity has recently attracted worldwide attention as it causes renal failure and the death of humans and animals. "	( Colorimetric method for the detection of melamine using in-situ formed silver nanoparticles via tannic acid. Ahmed, S; Alam, MF; Laskar, AA; Shaida, MA; Younus, H, 2017)	2.16
"Melamine detection has attracted much attention since the discovery of the damage of melamine to human health. "	( Triplex DNA-based Bioanalytical Platform for Highly Sensitive Homogeneous Electrochemical Detection of Melamine. Li, F; Liu, X; Song, M, 2017)	2.11
"Melamine poisoning has become widely publicized after a recent occurrence of renal injury in infants and children exposed to melamine-tainted milk in China. "	( Melamine-induced renal toxicity is mediated by the gut microbiota. Bao, Y; Chi, Y; Jia, W; Li, H; Luther, M; Nicholson, JK; Su, M; Wang, C; Xie, G; Zhao, A; Zhao, L; Zheng, X, 2013)	3.28
"Melamine, which has a multi-nitrogen heterocyclic ring, is prone to coordinate with Hg(2+)."	( Label-free turn-on fluorescent detection of melamine based on the anti-quenching ability of Hg 2+ to gold nanoclusters. Dai, H; Hu, J; Li, Z; Ni, P; Shi, Y; Sun, Y; Wang, Y, 2014)	1.38
"Melamine has been reported for human harmful effects and detected from some crops, soil and water."	( Mineralization of melamine and cyanuric acid as sole nitrogen source by newly isolated Arthrobacter spp. using a soil-charcoal perfusion method. Fujii, K; Hatakeyama, T; Ito, K; Naokawa, T; Sakakibara, F; Takagi, K; Takasu, E; Yamazaki, K, 2015)	1.47
"Melamine has been reported to be responsible for the renal impairment in mammals, its toxicity on the reproductive system, however, has not been adequately assessed."	( Melamine Induces Oxidative Stress in Mouse Ovary. Cui, XS; Dai, XX; Duan, X; Kim, NH; Sun, SC; Xiong, B, 2015)	2.58
"Melamine may have been an important prebiotic information carrier, but its excited-state dynamics, which determine its stability under UV radiation, have never been characterized. "	( Excited-State Dynamics of Melamine and Its Lysine Derivative Investigated by Femtosecond Transient Absorption Spectroscopy. Beckstead, AA; Bong, D; Hu, Y; Kohler, B; Piao, X; Zhang, Y, 2016)	2.18
"Melamine has become the focus of attention for the possible occurrence of nephrolithiasis and associated deaths, because it was added to foods to increase the apparent protein content by unethical manufacturers. "	( Hydrophilic interaction chromatography/tandem mass spectrometry for the determination of melamine in royal jelly and royal jelly lyophilized powder. Chen, F; Li, C; Li, Y; Mi, J; Wu, L; Xue, X; Zhang, J; Zhao, J; Zhou, J, 2009)	2.02
"Melamine ingestion has been implicated in stone formation when co-ingested with cyanuric acid, but will cause urinary stones in infants when large amounts of melamine alone are ingested."	( Melamine toxicity. Osterloh, JD; Skinner, CG; Thomas, JD, 2010)	2.52
"Melamine has been the main factor leading to infant urinary calculi occurring on a rather wide scale in China in 2008, which were the results of a rapid aggradation of metabolites such as cyanuric acid diamide, cyanuric acid, etc., causing uric acid stone to accumulate. "	( Melamine-induced infant urinary calculi: a report on 24 cases and a 1-year follow-up. Bai, J; Jiang, B; Ma, J; Ma, P; Wan, J; Zhang, X, 2010)	3.25
"Melamine (MEL) has been involved in several food recalls after the discovery of severe kidney damages in children and pets poisoned by melamine-adulterated food. "	( Preparation of monoclonal antibody for melamine and development of an indirect competitive ELISA for melamine detection in raw milk, milk powder, and animal feeds. Feng, C; He, F; Li, W; Liu, J; Liu, W; Lu, X; Meng, M; Wan, Y; Wang, S; Xi, R; Yin, W; Zhang, T, 2010)	2.07
"Melamine (M) sensing has been achieved through supramolecular assembly with riboflavin (R) via H-bonding in the platform of R stabilized gold nanoparticles (R-Au NPs), by colorimetric as well as UV-vis techniques."	( Melamine sensing through riboflavin stabilized gold nanoparticles. Nandi, AK; Roy, B; Saha, A, 2011)	3.25
"Melamine molecule has multiple -NH(2) groups."	( Selective determination of melamine in milk samples using 3-mercapto-1-propanesulfonate-modified gold nanoparticles as colorimetric probe. Ai, S; Bian, P; Fan, H; Liu, J; Su, H; Wu, N, 2011)	1.39
"Melamine has recently been recognized as a food contaminant with adverse human health effects. "	( Biodegradation of melamine and its hydroxy derivatives by a bacterial consortium containing a novel Nocardioides species. Fujii, K; Harada, N; Iwasaki, A; Takagi, K; Yamazaki, K, 2012)	2.16
"Melamine has been used for the adulteration of cereal flours in order to increase their apparent protein content. "	( High-performance liquid chromatographic method for the simultaneous detection of the adulteration of cereal flours with melamine and related triazine by-products ammeline, ammelide, and cyanuric acid. Ehling, S; Ho, IP; Tefera, S, 2007)	1.99

Actions

Melamine can cause urinary stones related to nephropathy of the kidney and hyperplasia or carcinoma of the bladder. Melamine that can cause serious damage to the organs was found to bind to polythymine via hydrogen bonding.

Excerpt	Reference	Relevance
"Melamine overdose can cause an increased risk of developing kidney stones in children. "	( The clinical analysis of young children's urolithiasis due to melamine-tainted infant formula. Feng, H; Sun, DQ; Yang, YH; Zhang, L; Zhang, XF, 2010)	2.04
"Melamine that can cause serious damage to the organs of animal or human beings was found to bind to polythymine via hydrogen bonding. "	( Visual detection of melamine in milk samples based on label-free and labeled gold nanoparticles. Feng, Y; He, Z; Huang, H; Li, L; Liu, Z; Ma, Q; Tinnefeld, P; Zeng, G; Zhou, G, 2011)	2.14
"Melamine can cause urinary stones related to nephropathy of the kidney and hyperplasia or carcinoma of the bladder, but the mechanism of stone formation is not well understood. "	( Proteome of melamine urinary bladder stones and implication for stone formation. Hu, JJ; Huang, HY; Liu, JD; Liu, JJ; Tao, GH; Wu, DS; Xu, XY; Yang, LQ; Yang, XF; Yuan, JH; Zhou, L; Zhuang, ZX, 2012)	2.2

Treatment

Melamine-treatment of the fish caused degenerative changes in the pigment granules and also the other cytoplasmic organelles of the leucophores. Rats treated with melamine developed adverse health effects compared to the controls, including decrease in body weight and kidney damage.

Excerpt	Reference	Relevance
"Melamine-cyanuric acid-treated rats showed marked kidney swelling, vacuolization and necrosis in the proximal tubules, and numerous polarizable crystals were located in the distal segments, causing increases in kidney weight, serum BUN and creatinine."	( Effects of sodium citrate on melamine-cyanuric acid mixture-induced urolithiasis in rats. Chang, SC; Chen, YT; Chien, MS; Chou, CC; Hsuan, SL; Jiann, BP; Lee, WC; Lee, YF; Liao, JW; Tsai, FJ, 2013)	1.4
"Melamine-treated rats presented a marked decrease in learning and memory in the Morris water maze (MWM) as well as a reduced efficiency to find the platform in the reversal learning task."	( Vitamins C and E reverse melamine-induced deficits in spatial cognition and hippocampal synaptic plasticity in rats. An, L; Zhang, T, 2014)	1.43
"All melamine-treated animals experienced adverse effects; however, pregnant rats were most sensitive as indicated by increased SCr, BUN, and kidney weights, decreased body weight, and presence of renal crystals."	( Use of urinary renal biomarkers to evaluate the nephrotoxic effects of melamine or cyanuric acid in non-pregnant and pregnant rats. Bandele, OJ; Black, T; Crosby, TC; Evans, ER; Ferguson, M; Keltner, Z; Olejnik, N; Reimschuessel, R; Sprando, RL; Stine, CB, 2014)	1.12
"In melamine-treated groups, milk melamine concentration increased quickly and reached a stable level by d 4 and was at similar levels on d 8 and 12 after the first administration of melamine."	( Residues of melamine and cyanuric acid in milk and tissues of dairy cows fed different doses of melamine. Shen, JS; Sun, P; Wang, JQ; Wei, HY, 2011)	1.26
"Melamine-treatment of the fish caused degenerative changes in the pigment granules and also the other cytoplasmic organelles of the leucophores, whereas the other kinds of chromatophores, including the iridiophores, remained intact."	( Electron microscopy of two types of reflecting chromatophores (iridophores and leucophores) in the guppy, Lebistes reticulatus Peters. Takeuchi, IK, 1976)	0.98
"Rats treated with melamine developed adverse health effects compared to the controls, including decrease in body weight and kidney damage."	( An NMR-based metabonomic investigation of the subacute effects of melamine in rats. Li, W; Liang, YJ; Sun, YJ; Wang, HP; Wu, YJ; Yang, L, 2012)	0.94
"Oral treatment with melamine (5 and 25mg/kg) 1h before behavioral tests significantly decreased the immobility time of the forced swim test in 2-3month-old rats and had no effect on locomotor activity in the open field test in both P21-28 and 2-3month-old rats."	( Acute low-dose melamine affects hippocampal synaptic plasticity and behavior in rats. Cao, J; Mao, RR; Wang, LP; Xiong, GJ; Xu, L; Yang, Y; Yu, DF, 2012)	1.05

Toxicity

Melamine is a widely used industrial chemical not considered acutely toxic with a high LD(50) in animals. Future studies should consider uric acid together with melamine when examining adverse effects in humans.

Excerpt	Reference	Relevance
" These results establish the causal link between the contaminated gluten and the adverse effects and provide a mechanistic explanation for how two apparently innocuous compounds could have adverse effects in combination, that is, by forming an insoluble precipitate in renal tubules leading to progressive tubular blockage and degeneration."	( Identification and characterization of toxicity of contaminants in pet food leading to an outbreak of renal toxicity in cats and dogs. Baker, TR; Bigalow-Kern, AS; Cambron, RT; Daston, GP; Dobson, RL; Fix, A; Motlagh, S; Overmann, G; Pullen, AM; Quijano, M; Regg, BT; Reimschuessel, R; Shan, Y; Vennard, T, 2008)	0.35
"This article discusses the 2007 recall of canned pet food because of concerns about adverse effects on kidney function of cats and dogs."	( Melamine and cyanuric acid-induced crystalluria, uroliths, and nephrotoxicity in dogs and cats. Albasan, H; Koehler, LA; Lulich, JP; Osborne, CA; Sauer, L; Schubert, G; Ulrich, LK, 2009)	1.8
" A variety of toxic effects from melamine, including nephrolithiasis, chronic kidney inflammation, and bladder carcinoma, all have been studied in animals."	( Melamine toxicity and the kidney. Hau, AK; Kwan, TH; Li, PK, 2009)	2.08
" Melamine is the latest in a growing list of diverse potentially toxic compounds about which nephrologists and other health-care providers responsible for the diagnosis and management of kidney disease must now be aware."	( Melamine nephrotoxicity: an emerging epidemic in an era of globalization. Bhalla, V; Chertow, GM; Grimm, PC; Pao, AC, 2009)	2.71
" Melamine is a widely used industrial chemical not considered acutely toxic with a high LD(50) in animals."	( Melamine toxicity. Osterloh, JD; Skinner, CG; Thomas, JD, 2010)	2.71
" Dietary melamine had no adverse effects on laying performance."	( Toxicity of dietary melamine to laying ducks: biochemical and histopathological changes and residue in eggs. Fan, ZY; Gao, CQ; Ji, F; Liu, FZ; Liu, QS; Qi, GH; Wu, SG; Yue, HY; Zhang, HJ, 2010)	1.1
" Limited toxicological data indicate that MEL+CYA toxicity occurs at levels lower than the toxic doses of the single compounds."	( Using urinary solubility data to estimate the level of safety concern of low levels of melamine (MEL) and cyanuric acid (CYA) present simultaneously in infant formulas. Constable, A; Dominguez-Estevez, M; Mazzatorta, P; Renwick, AG; Schilter, B, )	0.35
" The observed adverse effect level (8."	( Dose-response assessment of nephrotoxicity from a 7-day combined exposure to melamine and cyanuric acid in F344 rats. Beland, FA; Gamboa da Costa, G; Hattan, DG; Jacob, CC; Olson, GR; Reimschuessel, R; Von Tungeln, LS; Warbritton, AR, 2011)	0.6
" CYA alone and the combination of MEL and CYA had adverse effects on the performance, but MEL alone had no effects on the performance."	( Toxicity of melamine and cyanuric acid in broilers and residues in tissues. Bai, SP; Ding, XM; Wang, L; Zhang, KY, 2012)	0.76
" And melamine can pass through the placental and blood-brain barrier, and then exerts toxic effects on the central nervous system."	( [Progress in mechanisms underlying melamine toxicity in central nervous system]. An, L; Yang, JJ; Yang, Z; Zhang, T, 2012)	1.17
" Our results illustrate the ability of both methods to detect and differentiate the severity of adverse effects in the staggered and consecutive gavage groups at much lower doses than previously observed in animals co-exposed to the compounds in feed."	( Performance of urinary and gene expression biomarkers in detecting the nephrotoxic effects of melamine and cyanuric acid following diverse scenarios of co-exposure. Bandele, O; Black, T; Camacho, L; Ferguson, M; Gamboa da Costa, G; Keltner, Z; Olejnik, N; Reimschuessel, R; Scott, M; Sprando, R; Stine, C, 2013)	0.61
"A rapid and sensitive method has been developed for the simultaneous detection of cyromazine and melamine in chicken eggs using the quick, easy, cheap, effective, rugged and safe (QuEChERS) method coupled with liquid chromatography-tandem mass spectrometry (LC-MS/MS)."	( Determination of cyromazine and melamine in chicken eggs using quick, easy, cheap, effective, rugged and safe (QuEChERS) extraction coupled with liquid chromatography-tandem mass spectrometry. Chen, CY; Chou, CC; Lee, MR; Lee, RJ; Wang, PC, 2012)	0.88
" Toxic effects on the gills manifested as epithelial hyperplasia of the primary and secondary lamellae."	( Toxicity of melamine, an adulterant in fish feeds: experimental assessment of its effects on tilapia. Boonyaratpalin, M; Kiron, V; Nuntapong, N; Phromkunthong, W, 2013)	0.77
" The combined exposure to melamine and cyanuric acid was revealed to have certain toxic effects on testis of male mice at a relative low dose (each at 1 mg/kg/day)."	( The reproductive toxicity of melamine in the absence and presence of cyanuric acid in male mice. Bai, WL; He, JB; Li, C; Liu, BS; Liu, J; Wang, XZ; Wu, CD; Yin, RH; Yin, RL, 2013)	0.98
" Melamine supplementation at a dose of 20000 ppm in the diet for 28 days induced adverse effects on the liver, decreased serum total protein and increased liver enzyme: alanine aminotransferase, aspartate aminotransferase, and alkaline phosphatase."	( Bees' honey protects the liver of male rats against melamine toxicity. Al-Seeni, MN; Al-Solamy, SM; El Rabey, HA, 2013)	1.55
" Since then, animal studies have revealed the possible target organs of the melamine toxicity and the extent of the adverse effects of the contaminant."	( Toxicity of melamine: the public health concern. Chu, CY; Wang, CC, 2013)	1
"Screening of the toxic effect of a high oral melamine dose (30,000 ppm supplemented in the diet) was performed for 28 days on male rats."	( Screening of the toxic effects of a high melamine dose on the biochemical hematological and histopathological investigations in male rats. Al-Sieni, AI; El Rabey, HA; Majami, AA, 2014)	0.93
"This study examined the adverse effects of feed-delivered melamine (MEL) and cyanuric acid (CYA) in red tilapia."	( Pathophysiological changes associated with dietary melamine and cyanuric acid toxicity in red tilapia. Boonyaratpalin, M; Choochuay, P; Kiron, V; Nuntapong, N; Phromkunthong, W, 2015)	0.91
"Melamine in combination with cyanuric acid has been considered to be more toxic than either melamine or cyanuric acid alone."	( An evaluation of genotoxicity and cytotoxicity of melamine in combination with cyanuric acid at three mass ratios. Gong, ZY; Huang, da W; Jia, XW; Liu, X; Wu, KJ; Wu, YN, 2014)	2.1
" In conclusion, this study revealed that natural bee honey protects the kidney against the adverse effects induced by melamine toxicity in male albino rats."	( The protective role of bee honey against the toxic effect of melamine in the male rat kidney. Al-Seeni, MN; Al-Solamy, SM; El Rabey, HA, 2015)	0.87
" All melamine-treated animals experienced adverse effects; however, pregnant rats were most sensitive as indicated by increased SCr, BUN, and kidney weights, decreased body weight, and presence of renal crystals."	( Use of urinary renal biomarkers to evaluate the nephrotoxic effects of melamine or cyanuric acid in non-pregnant and pregnant rats. Bandele, OJ; Black, T; Crosby, TC; Evans, ER; Ferguson, M; Keltner, Z; Olejnik, N; Reimschuessel, R; Sprando, RL; Stine, CB, 2014)	1.15
" These results provided useful information for assessing the toxicity of melamine on immune system of mammals, and contributed to the existing toxic profile of melamine."	( The toxic effects of melamine on spleen lymphocytes with or without cyanuric acid in mice. Bai, WL; Han, J; Han, XH; Han, XR; He, JB; Li, HS; Liu, BS; Liu, J; Wang, WC; Wang, X; Yin, RH; Yin, RL, 2014)	0.95
" Future studies should consider uric acid together with melamine when examining adverse effects in humans."	( Melamine Nephrotoxicity is Mediated by Hyperuricemia. Li, HT; Liu, JM; Trachtman, H; Trasande, L; Wang, LL; Wang, PX; Zhang, L, 2015)	2.11
" In wildlife risk assessments, TRVs are thresholds represented by a dose or concentration associated with a specified adverse response."	( Benchmark dose analysis framework for developing wildlife toxicity reference values. Mayfield, DB; Skall, DG, 2018)	0.48
"Melamine is recalcitrant and toxic to bacteria in conventional activated sludge systems."	( Biodegradation and toxicity of melamine at high activated sludge concentrations in a membrane bioreactor. Hu, Z; Sun, M; Thompson, A; Xu, S, 2018)	2.21
" Two major genetic factors that are discussed include genetic polymorphisms in plasma membrane transporters that catalyze uptake and accumulation or efflux and elimination of environmental chemicals, and genetic polymorphisms in bioactivation enzymes that generate toxic and reactive metabolites."	( Environmental and Genetic Factors Influencing Kidney Toxicity. Lash, LH, 2019)	0.51
"The melamine and cyanuric acid (CA) complex has been suggested to cause the toxic effects observed in melamine-contaminated food or milk."	( Evaluation of the cytotoxic and genotoxic effects by melamine and cyanuric acid co-exposure in human embryonic kidney 293 cells. Gan, T; Lu, J; Sheng, H; Xu, X; Xu, Y; Yang, J; Zhang, J; Zhang, L; Zhu, X, 2020)	1.37
" The elevated concentrations of these compounds cause adverse effects in humans and animals."	( Protective effect of starch-stabilized selenium nanoparticles against melamine-induced hepato-renal toxicity in male albino rats. Abou-El-Sherbini, KS; Ahmed, ZSO; Drweesh, EA; Elnagar, MM; Elzahany, EAM; Galal, MK; Yasin, NAE, 2021)	0.86
" Former evidences implied that ML could induce a variety of toxic effects including neurotoxicity and cognitive impairment."	( Sesquiterpene nootkatone counteracted the melamine-induced neurotoxicity via repressing of oxidative stress, inflammatory, and apoptotic trajectories. Abdeen, A; Abdelkader, A; Abdelrahaman, D; Atwa, AM; Behairy, A; El-Hanafy, AA; El-Mosallamy, SA; Elgameel, D; Fericean, L; Ghamry, HI; Habotta, OA; Hasan, T; Ibrahim, SF; Imbrea, F; Mahdi, MR; Yassin, N, 2023)	1.17

Pharmacokinetics

There is little or no information concerning the pharmacokinetics of melamine in livestock. To establish an appropriate withdrawal interval, a physiologically based pharmacokinetic (PBPK) model for melamine was developed for rats and extrapolated to pigs.

Excerpt	Reference	Relevance
" There is little or no information concerning the pharmacokinetics of melamine in livestock, and the aim of this study was to obtain pharmacokinetic parameters for this contaminant in pigs."	( Pharmacokinetics of melamine in pigs following intravenous administration. Barlow, BM; Barrett, E; Baynes, RE; Mason, SE; Riviere, JE; Smith, G, 2008)	0.9
" To establish an appropriate withdrawal interval, a physiologically based pharmacokinetic (PBPK) model for melamine was developed for rats and extrapolated to pigs."	( Estimating meat withdrawal times in pigs exposed to melamine contaminated feed using a physiologically based pharmacokinetic model. Baynes, RE; Buur, JL; Riviere, JE, 2008)	0.81
"The objective of the study was to obtain pharmacokinetic parameters for melamine and blend of melamine (MEL) and cyanuric acid (CYA) in rainbow trout (Oncorhynchus mykiss)."	( Plasma pharmacokinetics of melamine and a blend of melamine and cyanuric acid in rainbow trout (Oncorhynchus mykiss). Qin, Y; Qiu, J; Wang, J; Wang, Q; Wu, X; Xue, M; Zheng, Y, 2011)	0.9
" Given this mode of action, a good understanding of the pharmacokinetic profiles of melamine and cyanuric acid and their combinations is essential to define properly the risk associated with different exposure scenarios."	( Pharmacokinetics of melamine and cyanuric acid and their combinations in F344 rats. Beland, FA; Gamboa da Costa, G; Jacob, CC; Vanlandingham, M; Von Tungeln, LS, 2012)	0.93
" In order to assess the pharmacokinetic profile of CYR, chickens were administered 1 or 10 mg/kg (single oral doses), whereas residue studies were conducted in chickens fed CYR alone (5 or 10 mg/kg) or CYR (5 mg/kg) and MEL (5 mg/kg) for a period of 14 days."	( Plasma pharmacokinetics and tissue depletion of cyromazine and its metabolite melamine following oral administration in laying chickens. Chang, SK; Chou, CC; Li, KP; Ou, SC; Rairat, T; Vickroy, TW, 2017)	0.68

Compound-Compound Interactions

Melamine in combination with cyanuric acid has been considered to be more toxic than either melamine or cyanurIC acid alone. The purpose of this study was to characterize the pathological lesions of the liver caused by melamine alone or in conjunction with CA.

Excerpt	Reference	Relevance
"An electrochemiluminescence (ECL) enhancement method combined with solid-phase extraction has been developed for the determination of melamine in dairy products."	( Determination of melamine in dairy products by an electrochemiluminescent method combined with solid-phase extraction. Gai, P; Gan, N; Guo, Z; Hao, T; Wang, S; Wei, D, 2011)	0.91
"The rapid qualitative and quantitative analysis of melamine in pet food was realized by surface-enhanced Raman spectroscopy in combination with Ag nanoparticle."	( [Rapid determination of melamine in pet food by surface enhanced Raman spectroscopy in combination with Ag nanoparticles]. Cheng, J; Su, XO, 2011)	0.93
" Therefore, feed contaminated with both MEL and CYA could be problematic for fish, as MEL administered to trout, individually or in combination with CYA, may facilitate the onset of oxidative damage in trout."	( Antioxidant responses and renal crystal formation in rainbow trout treated with melamine administered individually or in combination with cyanuric acid. Abete, MC; Andersen, W; Brizio, P; Dörr, AJ; Elia, AC; Gasco, L; Pacini, N; Prearo, M; Reimschuessel, R; Righetti, M, 2013)	0.62
"Melamine in combination with cyanuric acid has been considered to be more toxic than either melamine or cyanuric acid alone."	( An evaluation of genotoxicity and cytotoxicity of melamine in combination with cyanuric acid at three mass ratios. Gong, ZY; Huang, da W; Jia, XW; Liu, X; Wu, KJ; Wu, YN, 2014)	2.1
" The experimental groups of MEL100 and CA100 were orally administered with MEL and CA at 100 mg/kg/d for 7 d, respectively."	( Nephrotoxic potential and toxicokinetics of melamine combined with cyanuric acid in rats. Jeong, HG; Jeong, TC; Kang, MJ; Kang, W; Kim, GH; Kim, H; Kim, HS; Lee, KY; Noh, K; Oh, DG, 2014)	0.66
" In this research, near-infrared (NIR) hyperspectral imaging technique combined with regression coefficient of partial least squares regression (PLSR) model was used to detect melamine particles in milk powders easily and quickly."	( Detection of melamine in milk powders using near-infrared hyperspectral imaging combined with regression coefficient of partial least square regression model. Baek, I; Chao, K; Cho, BK; Fu, X; Kim, G; Kim, MS; Lim, J; Mo, C; Qin, J, 2016)	1
" The purpose of this study was to characterize the pathological lesions of the liver caused by melamine alone or in combination with CA."	( The pathologic lesions of liver caused by melamine alone or in combination with cyanuric acid in mice. Chang, L; She, R; Tong, D; Wu, Q, 2021)	1.1

Bioavailability

High-performance liquid chromatography with tandem mass spectrometry (HPLC/MS/MS) was used to determine melamine oral bioavailability (BA) and urinary excretion. The oral coadministration of 1 mg/kg body weight of melamine and cyanuric acid did not alter significantly the pharmacokinetic profiles in relation to those determined upon individual oral administration of each compound. Administration of equal amounts of each triazine as the preformed melamine cyanurate complex significantly altered the pharmacodynamics.

Excerpt	Reference	Relevance
"High-performance liquid chromatography with tandem mass spectrometry (HPLC/MS/MS) was used to determine melamine oral bioavailability (BA) and urinary excretion."	( Oral bioavailability, urinary excretion and organ distribution of melamine in Sprague-Dawley rats by high-performance liquid chromatography with tandem mass spectrometry. Chiu, TF; Ho, WA; Huang, CM; Lin, CC; Lin, CH; Lin, LC; Tarng, DC; Tsai, TH; Wu, YT, 2010)	0.81
" Although the oral coadministration of 1 mg/kg body weight of melamine and cyanuric acid did not alter significantly the pharmacokinetic profiles in relation to those determined upon individual oral administration of each compound, the administration of equal amounts of each triazine as the preformed melamine cyanurate complex significantly altered the pharmacokinetics, with reduced bioavailability of both compounds, lower observed maximum serum concentrations, delayed peak concentrations, and prolonged elimination half lives."	( Pharmacokinetics of melamine and cyanuric acid and their combinations in F344 rats. Beland, FA; Gamboa da Costa, G; Jacob, CC; Vanlandingham, M; Von Tungeln, LS, 2012)	0.94
" The knowledge of bioavailability of a contaminant in soil can be useful to conduct environmental risk assessment."	( Sorption characteristics of cyromazine and its metabolite melamine in typical agricultural soils of China. Dong, YH; Tang, LL; Toor, G; Wang, H; Wang, HY; Zhao, L, 2014)	0.65
" The absolute oral bioavailability (F) was 95."	( Toxicokinetics and absolute oral bioavailability of melamine in broiler chickens. Arreesrisom, P; Isariyodom, S; Klangkaew, N; Kumagai, S; Poapolathep, A; Poapolathep, S; Sugita-Konishi, Y, 2015)	0.67
" bioavailability was 90."	( Dispositions and tissue depletion of melamine in ducks. Giorgi, M; Isariyodom, S; Jermnak, U; Kumagai, S; Poapolathep, A; Poapolathep, S; Suknikom, P, 2016)	0.71
" Considering the effective role of Klonopin (KNP) in the treatment of epilepsy, KNP quantification in its production process for dose adjustments and checking the purity and also after its usage by patents for bioavailability testing and effectiveness assay is vital."	( Klonopin assay using modified electrode with multiwalled carbon nanotubes and poly melamine nanocomposite. Ghalkhani, M; Khaloo, SS; Mirzaie, RA, 2019)	0.74
" Finally, the study of theoretical physicochemical properties, the observation of low toxicity (hemolysis assay), and the evaluation of oral bioavailability of the TP derivative showed that it is a possible anti-inflammatory drug candidate."	( Castro, RI; Morales-Quintana, L; Valenzuela-Riffo, F, 2019)	0.51

Dosage Studied

Melamine is embryo-/fetotoxic at a maternotoxic dose, but not teratogenic in rats. Melamine was dosed continuously from day 125 in both activated sludge treatment systems at an influent concentration of 3 mg/L for about 100 days. During the entire 30 d exposure, the maximum melamine concentrations in eggs were 0·162, 0·998 and 1·784 mg/kg.

Excerpt	Relevance	Reference
" The dose-response curves for the induction of urolithiasis in weanling rats were extremely steep, consistent with the fact that the formation calculi can occur in urine that is supersaturated, but not in urine that is undersaturated with respect to the stone components."	( The induction of bladder stones by terephthalic acid, dimethyl terephthalate, and melamine (2,4,6-triamino-s-triazine) and its relevance to risk assessment. Heck, HD; Tyl, RW, 1985)	0.49
" Radioactivity in plasma or urine co-chromatographed with that of the dosing solution, indicating that melamine is not metabolized in the male Fischer 344 rat."	( Metabolism, disposition and excretion of [14C]melamine in male Fischer 344 rats. Friedman, MA; Jeffcoat, AR; Kraska, RC; Mast, RW; Sadler, BM, 1983)	0.74
" Acute and chronic inflammation and epithelial hyperplasia of the urinary bladder were found in increased incidence in dosed male mice (2250 and 4500 ppm) in the chronic study."	( Urolithiasis and bladder carcinogenicity of melamine in rodents. Boorman, GA; Haseman, JK; Huff, J; Melnick, RL; Montali, RJ, 1984)	0.53
" Cats dosed with a combination were euthanized at 48 hours after dosing because of acute renal failure."	( Assessment of melamine and cyanuric acid toxicity in cats. Filigenzi, MS; Lowenstine, LJ; Pesavento, PA; Poppenga, RH; Puschner, B, 2007)	0.7
" Chronic oral dosing (3."	( Estimating meat withdrawal times in pigs exposed to melamine contaminated feed using a physiologically based pharmacokinetic model. Baynes, RE; Buur, JL; Riviere, JE, 2008)	0.6
"Fish and pigs were fed a target dosage of melamine (400 mg/kg), cyanuric acid (400 mg/kg), or melamine and cyanuric acid (400 mg of each compound/kg) daily for 3 days and were euthanatized 1, 3, 6, 10, or 14 days after administration ceased."	( Evaluation of the renal effects of experimental feeding of melamine and cyanuric acid to fish and pigs. Andersen, WC; Bataller, N; Boehmer, J; Crowe, JB; de Alwis, GK; Gieseker, CM; Heller, DN; Karbiwnyk, CM; Miller, RA; Nochetto, C; Reimschuessel, R; Reinhard, MK; Roberts, JF; Rummel, N; Satzger, RD; Turnipseed, SB; Ward, J; Wilber, NR; Witkowski, MR, 2008)	0.85
" A higher dosage of melamine in the diet corresponded to higher concentrations in tissues and eggs."	( Tissue deposition and residue depletion in laying hens exposed to melamine-contaminated diets. Bai, F; Bai, S; Bai, X; Li, Y; Lin, S; Lv, X; Qin, Y; Zhang, K, 2010)	0.92
" The cows of treatments 1 to 4 were dosed with melamine at 0 (control), 90 (treatment 1), 270 (treatment 2), and 450 (treatment 3) mg/d per cow, respectively."	( Transfer efficiency of melamine from feed to milk in lactating dairy cows fed with different doses of melamine. Bu, DP; Shen, JS; Sun, P; Wang, JQ; Wei, HY; Zhou, LY, 2010)	0.93
" To determine the dose-response for nephrotoxicity upon coadministration of melamine and cyanuric acid, groups of male and female F344 rats (six animals per sex per group) were fed 0 (control), 7, 23, 69, 229, or 694 ppm of both melamine and cyanuric acid; 1388 ppm melamine; or 1388 ppm cyanuric acid in the diet for 7 days."	( Dose-response assessment of nephrotoxicity from a 7-day combined exposure to melamine and cyanuric acid in F344 rats. Beland, FA; Gamboa da Costa, G; Hattan, DG; Jacob, CC; Olson, GR; Reimschuessel, R; Von Tungeln, LS; Warbritton, AR, 2011)	0.83
" To conduct a safety assessment for melamine in infant formula, we established a dose-response relationship based on 13 nephrolithiasis cases selected from 932 children, all of whom were under 5 years of age and had potentially been exposed to contaminated milk in China or Taiwan."	( A hierarchical Bayesian approach for risk assessment of melamine in infant formula based on cases of related nephrolithiasis in children. Chan, CC; Chen, CC; Chen, PC; Leonardi, G; Wang, IJ; Wu, KY, 2011)	0.89
"91) with melamine dosing levels."	( Residues of melamine and cyanuric acid in milk and tissues of dairy cows fed different doses of melamine. Shen, JS; Sun, P; Wang, JQ; Wei, HY, 2011)	1.17
" These results show that 15-day repeated oral dosing of melamine is embryo-/fetotoxic at a maternotoxic dose, but not teratogenic in rats."	( Effects of melamine on pregnant dams and embryo-fetal development in rats. Kim, HC; Kim, JC; Kim, SH; Lee, IC; Lim, JH; Moon, C; Park, SC; Shin, IS, 2011)	1.01
" Peak concentrations of MM are reached in the livers and lungs at 12 h after dosing and in hearts, spleens, kidneys, bladders, feces, urine, and plasma at 24 h after dosing."	( Characterization of the disposition of melamine in female Sprague-Dawley rats using ultra-performance liquid chromatography-tandem mass spectrometry. Huang, H; Liu, J; Wu, D; Xu, X; Yang, L; Yuan, J; Zhao, Q; Zhou, L; Zhuang, Z, 2011)	0.64
" Four late-lactation dairy cows (body weight=524±17 kg, days in milk=265±14 d) fitted with ruminal cannulas were dosed with melamine (purity ≥99."	( Pathway for the elimination of melamine in lactating dairy cows. Shen, JS; Sun, P; Wang, JQ; Wei, HY, 2012)	0.87
" During the entire 30 d exposure, the maximum melamine concentrations in eggs were 0·162, 0·998 and 1·784 mg/kg for the 10, 50 and 100 mg/kg treatment groups, respectively, which demonstrated a linear dose-response relationship."	( Melamine residues in eggs of quails fed on diets containing different levels of melamine. Guo, YM; Wang, L; Zhang, BK, 2012)	2.08
" Clinical chemistry and histopathology indicated male rats were slightly more affected than female rats following dosing with the 120 and 180 ppm formulations; hydroxyproline excretion also supports this finding."	( Metabolomics evaluation of hydroxyproline as a potential marker of melamine and cyanuric acid nephrotoxicity in male and female Fischer F344 rats. Beger, RD; Bhattacharyya, S; Gamboa da Costa, G; Pence, LM; Schnackenberg, LK; Sun, J, 2012)	0.62
"Effects of the dosing matrix and timing on the onset of renal crystal formation were evaluated in male and non-pregnant female rats (Fisher 344) exposed to both melamine (MEL) and cyanuric acid (CYA) for 28 days."	( Timing and route of exposure affects crystal formation in melamine and cyanuric exposed male and female rats: gavage vs. feeding. Bandele, O; Black, T; Crosby, T; Evans, E; Ferguson, M; Gamboa da Costa, G; Keltner, Z; Loukotková, L; Nemser, SM; Olejnik, N; Reimschuessel, R; Scott, M; Sprando, RL; Stine, CB; Tkachenko, A; Woodling, K, 2012)	0.82
" The biomarkers were also evaluated for the ability to differentiate the effects of the compounds when co-administered using diverse dosing schedules (i."	( Performance of urinary and gene expression biomarkers in detecting the nephrotoxic effects of melamine and cyanuric acid following diverse scenarios of co-exposure. Bandele, O; Black, T; Camacho, L; Ferguson, M; Gamboa da Costa, G; Keltner, Z; Olejnik, N; Reimschuessel, R; Scott, M; Sprando, R; Stine, C, 2013)	0.61
" Melamine was dosed continuously from day 125 in both activated sludge treatment systems at an influent concentration of 3 mg/L for about 100 days."	( Fate and toxicity of melamine in activated sludge treatment systems after a long-term sludge adaptation. Bernards, M; Hu, Z; Sims, A; Xu, S; Zhang, Y, 2013)	1.62
" When dosed individually, melamine and cyanuric acid kidney residues depleted much faster than those in fish given both compounds together."	( Depletion of melamine and cyanuric acid in kidney of catfish Ictalurus punctatus and trout Oncorhynchus mykiss. Evans, ER; Gieseker, CM; Girard, L; Hasbrouck, NR; Mayer, TD; Nochetto, C; Reimschuessel, R; Stine, CB, 2013)	1.06
" Fish muscle residues of MEL exhibited a dose-response relationship."	( Antioxidant responses and renal crystal formation in rainbow trout treated with melamine administered individually or in combination with cyanuric acid. Abete, MC; Andersen, W; Brizio, P; Dörr, AJ; Elia, AC; Gasco, L; Pacini, N; Prearo, M; Reimschuessel, R; Righetti, M, 2013)	0.62
" Both control (CT-SAL) group and pair-fed (CT-VIT) group received the same dosage of CMC and vitamin complex, respectively."	( Vitamins C and E reverse melamine-induced deficits in spatial cognition and hippocampal synaptic plasticity in rats. An, L; Zhang, T, 2014)	0.71
" In groups dosed with MEL-CA mixtures, melamine and cyanuric acid (1:1) were simultaneously administered at 4, 20, or 100 mg/kg/d for 7 d (i."	( Nephrotoxic potential and toxicokinetics of melamine combined with cyanuric acid in rats. Jeong, HG; Jeong, TC; Kang, MJ; Kang, W; Kim, GH; Kim, H; Kim, HS; Lee, KY; Noh, K; Oh, DG, 2014)	0.93
" Pigs dosed with 33 mg/kg bw/day of MEL + CYA for 7 days contained residues above the level of concern only in kidney."	( Investigation of melamine and cyanuric acid deposition in pig tissues using LC-MS/MS methods. Bomba, M; Clark, J; Guag, J; Knutson, N; Nemser, SM; Reimschuessel, R; Rhodes, B; Tkachenko, A; Wallace, B; Yacopucci, M, 2015)	0.76
" Current practices such as process sterilization or antibiotic dosage carry excess costs or encourage the development of antibiotic resistance."	( Metabolic engineering of microbial competitive advantage for industrial fermentation processes. Brevnova, EE; Consiglio, A; Greenhagen, E; Hamilton, M; Lam, FH; LaTouf, WG; MacEwen, K; Shaw, AJ; South, CR; Stephanopoulos, G; van Dijken, H, 2016)	0.43
" Histopathological changes were significant in females dosed with ≥240 ppm MEL&CYA and in males dosed with ≥180 ppm MEL&CYA; however, the nephrotoxicity biomarkers blood urea nitrogen (BUN) and serum creatinine (SCr) were increased only by ≥240 ppm MEL&CYA."	( Effects of a 28-day dietary co-exposure to melamine and cyanuric acid on the levels of serum microRNAs in male and female Fisher 344 rats. Camacho, L; Chang, CW; Gamboa da Costa, G; Porter-Gill, P; Silva, CS; Williams, D, 2016)	0.7
" A BMD is derived using the full dose-response relationship from all experimental doses and may represent a user-specified response level (e."	( Benchmark dose analysis framework for developing wildlife toxicity reference values. Mayfield, DB; Skall, DG, 2018)	0.48
" Melamine was dosed at 3 mg/L for about 100 days."	( Biodegradation and toxicity of melamine at high activated sludge concentrations in a membrane bioreactor. Hu, Z; Sun, M; Thompson, A; Xu, S, 2018)	1.68
" Dose-response relationship was determined by utilizing cumulative occupational exposure dose and DNA damage."	( Estimation of formaldehyde occupational exposure limit based on genetic damage in some Iranian exposed workers using benchmark dose method. Sedghi, R; Vahabi, M; Zendehdel, R, 2018)	0.48
"0229 across the dosage levels."	( Evaluation of cyromazine transferred from feed to chicken products and subsequent assessment of dietary risks to Chinese consumers. Ji, X; Lyu, W; Qian, M; Wang, J; Wang, X; Yang, H, 2020)	0.56

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Role	Description
xenobiotic metabolite	Any metabolite produced by metabolism of a xenobiotic compound.
[role 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]

Class	Description
triamino-1,3,5-triazine
[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
melamine degradation	2	9

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
glucocorticoid receptor [Homo sapiens]	Homo sapiens (human)	Potency	0.0251	0.0002	14.3764	60.0339	AID588532
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	44 (3.33)	18.7374
1990's	23 (1.74)	18.2507
2000's	241 (18.26)	29.6817
2010's	823 (62.35)	24.3611
2020's	189 (14.32)	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	15 (1.11%)	5.53%
Reviews	51 (3.76%)	6.00%
Case Studies	12 (0.88%)	4.05%
Observational	0 (0.00%)	0.25%
Other	1,278 (94.25%)	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
ethylene glycol Ethylene Glycol: A colorless, odorless, viscous dihydroxy alcohol. It has a sweet taste, but is poisonous if ingested. Ethylene glycol is the most important glycol commercially available and is manufactured on a large scale in the United States. It is used as an antifreeze and coolant, in hydraulic fluids, and in the manufacture of low-freezing dynamites and resins.. ethanediol : Any diol that is ethane or substituted ethane carrying two hydroxy groups.. ethylene glycol : A 1,2-glycol compound produced via reaction of ethylene oxide with water.	3.85	3	0	ethanediol; glycol	metabolite; mouse metabolite; solvent; toxin
acetic acid Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.	2.77	3	0	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	2.54	2	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]	9.1	4	0	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
benzene [no description available]	2.21	1	0	aromatic annulene; benzenes; volatile organic compound	carcinogenic agent; environmental contaminant; non-polar solvent
benzoic acid Benzoic Acid: A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid.. benzoic acid : A compound comprising a benzene ring core carrying a carboxylic acid substituent.. aromatic carboxylic acid : Any carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.	3.59	2	0	benzoic acids	algal metabolite; antimicrobial food preservative; drug allergen; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; human xenobiotic metabolite; plant metabolite
benzyl alcohol Benzyl Alcohol: A colorless liquid with a sharp burning taste and slight odor. It is used as a local anesthetic and to reduce pain associated with LIDOCAINE injection. Also, it is used in the manufacture of other benzyl compounds, as a pharmaceutic aid, and in perfumery and flavoring.. hydroxytoluene : Any member of the class of toluenes carrying one or more hydroxy substituents.. benzyl alcohol : An aromatic alcohol that consists of benzene bearing a single hydroxymethyl substituent.. aromatic alcohol : Any alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.. aromatic primary alcohol : Any primary alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.	2.11	1	0	benzyl alcohols	antioxidant; fragrance; metabolite; solvent
carbamates [no description available]	2.25	1	0	amino-acid anion
formic acid formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.	2.05	1	0	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
methane Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).	4.22	15	0	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
citric acid, anhydrous Citric Acid: A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability.. citric acid : A tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms.	3.82	10	0	tricarboxylic acid	antimicrobial agent; chelator; food acidity regulator; fundamental metabolite
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	2.6	1	0	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
hydrochloric acid Hydrochloric Acid: A strong corrosive acid that is commonly used as a laboratory reagent. It is formed by dissolving hydrogen chloride in water. GASTRIC ACID is the hydrochloric acid component of GASTRIC JUICE.. hydrogen chloride : A mononuclear parent hydride consisting of covalently bonded hydrogen and chlorine atoms.	2.5	2	0	chlorine molecular entity; gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
phloroglucinol Phloroglucinol: A trinitrobenzene derivative with antispasmodic properties that is used primarily as a laboratory reagent.. phloroglucinol : A benzenetriol with hydroxy groups at position 1, 3 and 5.	7.15	1	0	benzenetriol; phenolic donor	algal metabolite
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	7.11	1	0	trihydroxybenzoic acid	antineoplastic agent; antioxidant; apoptosis inducer; astringent; cyclooxygenase 2 inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; geroprotector; human xenobiotic metabolite; plant metabolite
3,4-dihydroxyphenylacetic acid 3,4-Dihydroxyphenylacetic Acid: A deaminated metabolite of LEVODOPA.. (3,4-dihydroxyphenyl)acetic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine.. dihydroxyphenylacetic acid : A dihydroxy monocarboxylic acid consisting of phenylacetic acid having two phenolic hydroxy substituents.	7.05	1	0	catechols; dihydroxyphenylacetic acid	human metabolite
creatine [no description available]	3.23	1	0	glycine derivative; guanidines; zwitterion	geroprotector; human metabolite; mouse metabolite; neuroprotective agent; nutraceutical
dimethylamine [no description available]	2.17	1	0	methylamines; secondary aliphatic amine	metabolite
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	3.16	1	0	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
formaldehyde paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy	7.23	70	0	aldehyde; one-carbon compound	allergen; carcinogenic agent; disinfectant; EC 3.5.1.4 (amidase) inhibitor; environmental contaminant; Escherichia coli metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
glycine [no description available]	3.63	2	0	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical
glyceraldehyde Glyceraldehyde: An aldotriose containing the propionaldehyde structure with hydroxy groups at the 2- and 3-positions. It is involved in the formation of ADVANCED GLYCOSYLATION END PRODUCTS.. glyceraldehyde : An aldotriose comprising propanal having hydroxy groups at the 2- and 3-positions. It plays role in the formation of advanced glycation end-products (AGEs), a deleterious accompaniment to ageing.. aldose : Aldehydic parent sugars (polyhydroxy aldehydes H[CH(OH)]nC(=O)H, n >= 2) and their intramolecular hemiacetals.	2.08	1	0	aldotriose	fundamental metabolite
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	2.06	1	0	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
glycocyamine glycocyamine: RN given refers to parent cpd; structure. guanidinoacetate : A monocarboxylic acid anion that is the conjugate base of guanidinoacetic acid, obtained by deprotonation of the carboxy group.. guanidinoacetic acid : The N-amidino derivative of glycine.	3.23	1	0	guanidinoacetic acids; zwitterion	bacterial metabolite; human metabolite; mouse metabolite; nutraceutical; rat 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	3.11	3	0	hydracid; one-carbon compound	Escherichia coli metabolite; human metabolite; poison
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.	8.48	6	0	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
hydroquinone [no description available]	2.05	1	0	benzenediol; hydroquinones	antioxidant; carcinogenic agent; cofactor; Escherichia coli metabolite; human xenobiotic metabolite; mouse metabolite; skin lightening agent
indoleacetic acid indoleacetic acid: RN given refers to unlabeled parent cpd; structure in Merck Index, 9th ed, #4841. auxin : Any of a group of compounds, both naturally occurring and synthetic, that induce cell elongation in plant stems (from Greek alphaupsilonxialphanuomega, "to grow").. indole-3-acetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.	2.17	1	0	indole-3-acetic acids; monocarboxylic acid	auxin; human metabolite; mouse metabolite; plant hormone; plant metabolite
iodine Iodine: A nonmetallic element of the halogen group that is represented by the atomic symbol I, atomic number 53, and atomic weight of 126.90. It is a nutritionally essential element, especially important in thyroid hormone synthesis. In solution, it has anti-infective properties and is used topically.. diiodine : Molecule comprising two covalently bonded iodine atoms with overall zero charge..	2.1	1	0	diatomic iodine	nutrient
malonic acid malonic acid : An alpha,omega-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group.. dicarboxylic acid : Any carboxylic acid containing two carboxy groups.	2.15	1	0	alpha,omega-dicarboxylic acid	human metabolite
pyruvaldehyde Pyruvaldehyde: An organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.. methylglyoxal : A 2-oxo aldehyde derived from propanal.	2.08	1	0	2-oxo aldehyde; propanals	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
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.	8.48	7	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
phytic acid Phytic Acid: Complexing agent for removal of traces of heavy metal ions. It acts also as a hypocalcemic agent.. myo-inositol hexakisphosphate : A myo-inositol hexakisphosphate in which each hydroxy group of myo-inositol is monophosphorylated.	2.13	1	0	inositol phosphate
melatonin [no description available]	3.16	1	0	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	4.28	5	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
nitrites Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)	2.54	2	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
hydroxide ion [no description available]	3.35	1	0	oxygen hydride	mouse metabolite
orotic acid Orotic Acid: An intermediate product in PYRIMIDINE synthesis which plays a role in chemical conversions between DIHYDROFOLATE and TETRAHYDROFOLATE.. orotic acid : A pyrimidinemonocarboxylic acid that is uracil bearing a carboxy substituent at position C-6.	7.06	1	0	pyrimidinemonocarboxylic acid	Escherichia coli metabolite; metabolite; mouse metabolite
4-aminobenzoic acid 4-Aminobenzoic Acid: An aminobenzoic acid isomer that combines with pteridine and GLUTAMIC ACID to form FOLIC ACID. The fact that 4-aminobenzoic acid absorbs light throughout the UVB range has also resulted in its use as an ingredient in SUNSCREENS.. 4-ammoniobenzoate : A zwitterion obtained by transfer of a proton from the carboxy to the amino group of 4-aminobenzoic acid.. 4-aminobenzoic acid : An aminobenzoic acid in which the amino group is para to the carboxy group.	2.1	1	0	aminobenzoic acid; aromatic amino-acid zwitterion	allergen; Escherichia coli metabolite; plant metabolite
4-nitrophenol 4-nitrophenol: RN given refers to parent cpd. mononitrophenol : A nitrophenol that is phenol carrying a single nitro substituent at unspecified position.. 4-nitrophenol : A member of the class of 4-nitrophenols that is phenol in which the hydrogen that is para to the hydroxy group has been replaced by a nitro group.	7.57	2	0	4-nitrophenols	human xenobiotic metabolite; mouse metabolite
triphosphoric acid triphosphoric acid: used as water softener, peptizing agent, emulsifier & dispersing agent; ingredient of cleansers; meat preservative; RN given refers to parent cpd; structure	2.15	1	0	acyclic phosphorus acid anhydride; phosphorus oxoacid
phenol [no description available]	2.54	2	0	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
phthalic acid phthalic acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7178. phthalic acid : A benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions.	4.31	5	0	benzenedicarboxylic acid	human xenobiotic metabolite
propylene glycol Propylene Glycol: A clear, colorless, viscous organic solvent and diluent used in pharmaceutical preparations.. propane-1,2-diol : The simplest member of the class of propane-1,2-diols, consisting of propane in which a hydrogen at position 1 and a hydrogen at position 2 are substituted by hydroxy groups. A colourless, viscous, hygroscopic, low-melting (-59degreeC) and high-boiling (188degreeC) liquid with low toxicity, it is used as a solvent, emulsifying agent, and antifreeze.	2.06	1	0	glycol; propane-1,2-diols	allergen; human xenobiotic metabolite; mouse metabolite; protic solvent
sulfites Sulfites: Inorganic salts of sulfurous acid.. sulfites : Any sulfurous acid derivative that is a salt or an ester of sulfurous acid.. organosulfonate oxoanion : An organic anion obtained by deprotonation of the sufonate group(s) of any organosulfonic acid.. sulfite : A sulfur oxoanion that is the conjugate base of hydrogen sulfite (H2SO3).	2.07	1	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion
sulfuric acid sulfuric acid : A sulfur oxoacid that consists of two oxo and two hydroxy groups joined covalently to a central sulfur atom.	2.11	1	0	sulfur oxoacid	catalyst
thymine [no description available]	3.95	12	0	pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	7.81	3	0	pyrimidine nucleobase; pyrimidone	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; prodrug; Saccharomyces cerevisiae metabolite
uric acid Uric Acid: An oxidation product, via XANTHINE OXIDASE, of oxypurines such as XANTHINE and HYPOXANTHINE. It is the final oxidation product of purine catabolism in humans and primates, whereas in most other mammals URATE OXIDASE further oxidizes it to ALLANTOIN.. uric acid : An oxopurine that is the final oxidation product of purine metabolism.. 6-hydroxy-1H-purine-2,8(7H,9H)-dione : A tautomer of uric acid having oxo groups at C-2 and C-8 and a hydroxy group at C-6.. 7,9-dihydro-1H-purine-2,6,8(3H)-trione : An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8.	5.68	23	0	uric acid	Escherichia coli metabolite; human metabolite; mouse metabolite
urea pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.	6.04	33	0	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	2.25	1	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
2,2'-dipyridyl 2,2'-Dipyridyl: A reagent used for the determination of iron.. 2,2'-bipyridine : A bipyridine in which the two pyridine moieties are linked by a bond between positions C-2 and C-2'.	2.48	2	0	bipyridine	chelator; ferroptosis inhibitor
2,4-dinitrophenol 2,4-Dinitrophenol: A toxic dye, chemically related to trinitrophenol (picric acid), used in biochemical studies of oxidative processes where it uncouples oxidative phosphorylation. It is also used as a metabolic stimulant. (Stedman, 26th ed). dinitrophenol : Members of the class of nitrophenol carrying two nitro substituents.. 2,4-dinitrophenol : A dinitrophenol having the nitro groups at the 2- and 4-positions.	6.93	1	0	dinitrophenol	allergen; antiseptic drug; bacterial xenobiotic metabolite; geroprotector; oxidative phosphorylation inhibitor
albuterol Albuterol: A short-acting beta-2 adrenergic agonist that is primarily used as a bronchodilator agent to treat ASTHMA. Albuterol is prepared as a racemic mixture of R(-) and S(+) stereoisomers. The stereospecific preparation of R(-) isomer of albuterol is referred to as levalbuterol.. albuterol : A member of the class of phenylethanolamines that is 4-(2-amino-1-hydroxyethyl)-2-(hydroxymethyl)phenol having a tert-butyl group attached to the nirogen atom. It acts as a beta-adrenergic agonist used in the treatment of asthma and chronic obstructive pulmonary disease (COPD).	2.08	1	0	phenols; phenylethanolamines; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; environmental contaminant; xenobiotic
2-aminothiazole 2-aminothiazole: RN given refers to parent cpd; structure. 1,3-thiazol-2-amine : A primary amino compound that is 1,3-thiazole substituted by an amino group at position 2.	7.01	1	0	1,3-thiazoles; primary amino compound
acetovanillone apocynin : An aromatic ketone that is 1-phenylethanone substituted by a hydroxy group at position 4 and a methoxy group at position 3.	2.11	1	0	acetophenones; aromatic ketone; methyl ketone	antirheumatic drug; EC 1.6.3.1. [NAD(P)H oxidase (H2O2-forming)] inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug; plant metabolite
aristolochic acid i aristolochic acid I: phospholipase A inhibitor. aristolochic acid A : An aristolochic acid that is phenanthrene-1-carboxylic acid that is substituted by a methylenedioxy group at the 3,4 positions, by a methoxy group at position 8, and by a nitro group at position 10. It is the most abundant of the aristolochic acids and is found in almost all Aristolochia (birthworts or pipevines) species. It has been tried in a number of treatments for inflammatory disorders, mainly in Chinese and folk medicine. However, there is concern over their use as aristolochic acid is both carcinogenic and nephrotoxic.	9.5	3	0	aristolochic acids; aromatic ether; C-nitro compound; cyclic acetal; monocarboxylic acid; organic heterotetracyclic compound	carcinogenic agent; metabolite; mutagen; nephrotoxin; toxin
atrazine [no description available]	7.76	3	0	chloro-1,3,5-triazine; diamino-1,3,5-triazine	environmental contaminant; herbicide; xenobiotic
azobenzene azobenzene: photosensor molecule known to undergo reversible isomerization from trans to cis on illumination with photons of appropriate wavelength; RN given refers to cpd without isomeric designation; structure. (E)-azobenzene : The (E)-isomer of azobenzene.. (Z)-azobenzene : The (Z)-isomer of azobenzene.. azobenzene : A molecule whose structure comprises two phenyl rings linked by a N=N double bond; the parent compound of the azobenzene class of compounds.	7.42	2	0	azobenzenes
benzamidine benzamidine: RN given refers to parent cpd. benzamidine : A carboxamidine that is benzene carrying an amidino group.	2.07	1	0	benzenes; carboxamidine	serine protease inhibitor
benzyl isothiocyanate benzyl isothiocyanate: inhibits carcinogen-induced neoplasia; structure in Negwer, 5th ed, #715; also promotes urinary bladder carcinoma	2.1	1	0	benzenes; isothiocyanate	antibacterial drug
berberine [no description available]	2.54	2	0	alkaloid antibiotic; berberine alkaloid; botanical anti-fungal agent; organic heteropentacyclic compound	antilipemic drug; antineoplastic agent; antioxidant; EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor; EC 1.21.3.3 (reticuline oxidase) inhibitor; EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.1.4 (phospholipase A2) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; geroprotector; hypoglycemic agent; metabolite; potassium channel blocker
caffeine [no description available]	2.21	1	0	purine alkaloid; trimethylxanthine	adenosine A2A receptor antagonist; adenosine receptor antagonist; adjuvant; central nervous system stimulant; diuretic; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; environmental contaminant; food additive; fungal metabolite; geroprotector; human blood serum metabolite; mouse metabolite; mutagen; plant metabolite; psychotropic drug; ryanodine receptor agonist; xenobiotic
cetylpyridinium Cetylpyridinium: Cationic bactericidal surfactant used as a topical antiseptic for skin, wounds, mucous membranes, instruments, etc.; and also as a component in mouthwash and lozenges.	2.6	1	0	pyridinium ion
ciprofloxacin Ciprofloxacin: A broad-spectrum antimicrobial carboxyfluoroquinoline.. ciprofloxacin : A quinolone that is quinolin-4(1H)-one bearing cyclopropyl, carboxylic acid, fluoro and piperazin-1-yl substituents at positions 1, 3, 6 and 7, respectively.	2.02	1	0	aminoquinoline; cyclopropanes; fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone; zwitterion	antibacterial drug; antiinfective agent; antimicrobial agent; DNA synthesis inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; environmental contaminant; topoisomerase IV inhibitor; xenobiotic
clenbuterol Clenbuterol: A substituted phenylaminoethanol that has beta-2 adrenomimetic properties at very low doses. It is used as a bronchodilator in asthma.. clenbuterol : A substituted aniline that is 2,6-dichloroaniline in which the hydrogen at position 4 has been replaced by a 2-(tert-butylamino)-1-hydroxyethyl group.	3	4	0	amino alcohol; dichlorobenzene; ethanolamines; primary arylamine; secondary amino compound; substituted aniline	beta-adrenergic agonist; bronchodilator agent; sympathomimetic agent
clonazepam Clonazepam: An anticonvulsant used for several types of seizures, including myotonic or atonic seizures, photosensitive epilepsy, and absence seizures, although tolerance may develop. It is seldom effective in generalized tonic-clonic or partial seizures. The mechanism of action appears to involve the enhancement of GAMMA-AMINOBUTYRIC ACID receptor responses.. clonazepam : 1,3-Dihydro-2H-1,4-benzodiazepin-2-one in which the hydrogens at positions 5 and 7 are substituted by 2-chlorophenyl and nitro groups, respectively. It is used in the treatment of all types of epilepsy and seizures, as well as myoclonus and associated abnormal movements, and panic disorders. However, its use can be limited by the development of tolerance and by sedation.	7.53	2	0	1,4-benzodiazepinone; monochlorobenzenes	anticonvulsant; anxiolytic drug; GABA modulator
clorprenaline clorprenaline : A racemate comprise of equimolar amounts of (R)- and (S)-clorprenaline. It is a beta2-adrenergic receptor agonist and a bronchodilator.. 1-(2-chlorophenyl)-2-isopropylaminoethanol : A member of the class of monochlorobenzenes that is chlorobenzene which is substituted by a 1-hydroxy-2-[(propan-2-yl)amino]ethyl group at position 2.	7.15	1	0	ethanolamines; monochlorobenzenes; secondary amino compound
eflornithine Eflornithine: An inhibitor of ORNITHINE DECARBOXYLASE, the rate limiting enzyme of the polyamine biosynthetic pathway.. eflornithine : A fluoroamino acid that is ornithine substituted by a difluoromethyl group at position 2.	2.05	1	0	alpha-amino acid; fluoroamino acid	trypanocidal drug
diazinon Diazinon: A cholinesterase inhibitor that is used as an organothiophosphorus insecticide.. diazinon : A member of the class of pyrimidines that is pyrimidine carrying an isopropyl group at position 2, a methyl group at position 6 and a (diethoxyphosphorothioyl)oxy group at position 4.	2.25	1	0	organic thiophosphate; pyrimidines	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; environmental contaminant; nematicide; xenobiotic
dibutyl phthalate Dibutyl Phthalate: A plasticizer used in most plastics and found in water, air, soil, plants and animals. It may have some adverse effects with long-term exposure.. dibutyl phthalate : A phthalate ester that is the diester obtained by the formal condensation of the carboxy groups of phthalic acid with two molecules of butan-1-ol. Although used extensively as a plasticiser, it is a ubiquitous environmental contaminant that poses a risk to humans.	2.54	2	0	diester; phthalate ester	EC 3.2.1.20 (alpha-glucosidase) inhibitor; environmental contaminant; metabolite; plasticiser; teratogenic agent
domperidone Domperidone: A specific blocker of dopamine receptors. It speeds gastrointestinal peristalsis, causes prolactin release, and is used as antiemetic and tool in the study of dopaminergic mechanisms.. domperidone : 1-[3-(Piperidin-1-yl)propyl]-1,3-dihydro-2H-benzimidazol-2-one in which the 4-position of the piperidine ring is substituted by a 5-chloro-1,3-dihydro-2H-benzimidazol-2-on-1-yl group. A dopamine antagonist, it is used as an antiemetic for the short-term treatment of nausea and vomiting, and to control gastrointestinal effects of dopaminergic drugs given in the management of parkinsonism. The free base is used in oral suspensions, while the maleate salt is used in tablet preparations.	7.11	1	0	benzimidazoles; heteroarylpiperidine	antiemetic; dopaminergic antagonist
erythrosine Fluoresceins: A family of spiro(isobenzofuran-1(3H),9'-(9H)xanthen)-3-one derivatives. These are used as dyes, as indicators for various metals, and as fluorescent labels in immunoassays.	2.21	1	0
fluorouracil Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.	2.08	1	0	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
gentamicin Gentamicins: A complex of closely related aminoglycosides obtained from MICROMONOSPORA purpurea and related species. They are broad-spectrum antibiotics, but may cause ear and kidney damage. They act to inhibit PROTEIN BIOSYNTHESIS.	2.21	1	0
glutaral Glutaral: One of the protein CROSS-LINKING REAGENTS that is used as a disinfectant for sterilization of heat-sensitive equipment and as a laboratory reagent, especially as a fixative.. glutaraldehyde : A dialdehyde comprised of pentane with aldehyde functions at C-1 and C-5.	7.59	2	0	dialdehyde	cross-linking reagent; disinfectant; fixative
guanidine Guanidine: A strong organic base existing primarily as guanidium ions at physiological pH. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed) It is also used in the treatment of myasthenia and as a fluorescent probe in HPLC.. guanidine : An aminocarboxamidine, the parent compound of the guanidines.	2.11	1	0	carboxamidine; guanidines; one-carbon compound
haloperidol Haloperidol: A phenyl-piperidinyl-butyrophenone that is used primarily to treat SCHIZOPHRENIA and other PSYCHOSES. It is also used in schizoaffective disorder, DELUSIONAL DISORDERS, ballism, and TOURETTE SYNDROME (a drug of choice) and occasionally as adjunctive therapy in INTELLECTUAL DISABILITY and the chorea of HUNTINGTON DISEASE. It is a potent antiemetic and is used in the treatment of intractable HICCUPS. (From AMA Drug Evaluations Annual, 1994, p279). haloperidol : A compound composed of a central piperidine structure with hydroxy and p-chlorophenyl substituents at position 4 and an N-linked p-fluorobutyrophenone moiety.	3.1	5	0	aromatic ketone; hydroxypiperidine; monochlorobenzenes; organofluorine compound; tertiary alcohol	antidyskinesia agent; antiemetic; dopaminergic antagonist; first generation antipsychotic; serotonergic antagonist
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	2.41	1	0	monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; radical scavenger; xenobiotic
isoproterenol Isoproterenol: Isopropyl analog of EPINEPHRINE; beta-sympathomimetic that acts on the heart, bronchi, skeletal muscle, alimentary tract, etc. It is used mainly as bronchodilator and heart stimulant.. isoprenaline : A secondary amino compound that is noradrenaline in which one of the hydrogens attached to the nitrogen is replaced by an isopropyl group. A sympathomimetic acting almost exclusively on beta-adrenergic receptors, it is used (mainly as the hydrochloride salt) as a bronghodilator and heart stimulant for the management of a variety of cardiac disorders.	2.15	1	0	catechols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; sympathomimetic agent
malathion Malathion: A wide spectrum aliphatic organophosphate insecticide widely used for both domestic and commercial agricultural purposes.. malathion : A racemate comprising equimolar amounts of (R) and (S)-malathion. It is a broad spectrum organophosphate proinsecticide used to control a wide range of pests including Coleoptera, Diptera, fruit flies, mosquitos and spider mites.. diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate : A diester that is diethyl succinate in which position 2 is substituted by a (dimethoxyphosphorothioyl)thio group.	2.07	1	0	diester; ethyl ester; organic thiophosphate
mechlorethamine nitrogen mustard : Compounds having two beta-haloalkyl groups bound to a nitrogen atom, as in (X-CH2-CH2)2NR.	2.36	2	0	nitrogen mustard; organochlorine compound	alkylating agent
metformin Metformin: A biguanide hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. Metformin improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. (From Martindale, The Extra Pharmacopoeia, 30th ed, p289). metformin : A member of the class of guanidines that is biguanide the carrying two methyl substituents at position 1.	7.6	1	0	guanidines	environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic
methacrylic acid methacrylic acid: RN given refers to parent cpd. methacrylic acid : An alpha,beta-unsaturated monocarboxylic acid that is acrylic acid in which the hydrogen at position 2 is substituted by a methyl group.	3	4	0	alpha,beta-unsaturated monocarboxylic acid
methyl parathion Methyl Parathion: The methyl homolog of parathion. An effective, but highly toxic, organothiophosphate insecticide and cholinesterase inhibitor.. parathion-methyl : A C-nitro compound that is 4-nitrophenol substituted by a (dimethoxyphosphorothioyl)oxy group at position 4.	7.41	1	0	C-nitro compound; organic thiophosphate; organothiophosphate insecticide	acaricide; agrochemical; antifungal agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; environmental contaminant; genotoxin
oxonic acid Oxonic Acid: Antagonist of urate oxidase.	2.11	1	0	1,3,5-triazines; monocarboxylic acid
oxidopamine Oxidopamine: A neurotransmitter analogue that depletes noradrenergic stores in nerve endings and induces a reduction of dopamine levels in the brain. Its mechanism of action is related to the production of cytolytic free-radicals.. oxidopamine : A benzenetriol that is phenethylamine in which the hydrogens at positions 2, 4, and 5 on the phenyl ring are replaced by hydroxy groups. It occurs naturally in human urine, but is also produced as a metabolite of the drug DOPA (used for the treatment of Parkinson's disease).	2	1	0	benzenetriol; catecholamine; primary amino compound	drug metabolite; human metabolite; neurotoxin
pamidronate [no description available]	3.16	1	0	phosphonoacetic acid
4-chlorophenol 4-chlorophenol: used as a root canal irrigant. 4-chlorophenol : A monochlorophenol substituted at the pare position by a chlorine atom.	2.21	1	0	monochlorophenol
phenindione Phenindione: An indandione that has been used as an anticoagulant. Phenindione has actions similar to WARFARIN, but it is now rarely employed because of its higher incidence of severe adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p234)	3.16	1	0	aromatic ketone; beta-diketone	anticoagulant
potassium chloride Potassium Chloride: A white crystal or crystalline powder used in BUFFERS; FERTILIZERS; and EXPLOSIVES. It can be used to replenish ELECTROLYTES and restore WATER-ELECTROLYTE BALANCE in treating HYPOKALEMIA.. potassium chloride : A metal chloride salt with a K(+) counterion.	7.6	1	0	inorganic chloride; inorganic potassium salt; potassium salt	fertilizer
resorcinol resorcinol: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7951. resorcinol : A benzenediol that is benzene dihydroxylated at positions 1 and 3.	9.29	5	0	benzenediol; phenolic donor; resorcinols	erythropoietin inhibitor; sensitiser
roxarsone Roxarsone: An arsenic derivative which has anticoccidial action and promotes growth in animals.. roxarsone : An organoarsonic acid where the organyl group is 4-hydroxy-3-nitrophenyl.	2.17	1	0	2-nitrophenols; organoarsonic acid	agrochemical; animal growth promotant; antibacterial drug; coccidiostat
simazine Simazine: A triazine herbicide.. simazine : A diamino-1,3,5-triazine that is N,N'-diethyl-1,3,5-triazine-2,4-diamine substituted by a chloro group at position 6.	1.96	1	0	chloro-1,3,5-triazine; diamino-1,3,5-triazine	environmental contaminant; herbicide; xenobiotic
stearic acid octadecanoic acid : A C18 straight-chain saturated fatty acid component of many animal and vegetable lipids. As well as in the diet, it is used in hardening soaps, softening plastics and in making cosmetics, candles and plastics.	2.41	1	0	long-chain fatty acid; saturated fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; human metabolite; plant metabolite
sulfamethazine Sulfamethazine: A sulfanilamide anti-infective agent. It has a spectrum of antimicrobial action similar to other sulfonamides.. sulfamethazine : A sulfonamide consisting of pyrimidine with methyl substituents at the 4- and 6-positions and a 4-aminobenzenesulfonamido group at the 2-position.	2.15	1	0	pyrimidines; sulfonamide antibiotic; sulfonamide	antibacterial drug; antiinfective agent; antimicrobial agent; carcinogenic agent; drug allergen; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; ligand; xenobiotic
terbutaline Terbutaline: A selective beta-2 adrenergic agonist used as a bronchodilator and tocolytic.. terbutaline : A member of the class of phenylethanolamines that is catechol substituted at position 5 by a 2-(tert-butylamino)-1-hydroxyethyl group.	2.15	1	0	phenylethanolamines; resorcinols	anti-asthmatic drug; beta-adrenergic agonist; bronchodilator agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; hypoglycemic agent; sympathomimetic agent; tocolytic agent
theobromine Theobromine: 3,7-Dimethylxanthine. The principle alkaloid in Theobroma cacao (the cacao bean) and other plants. A xanthine alkaloid that is used as a bronchodilator and as a vasodilator. It has a weaker diuretic activity than THEOPHYLLINE and is also a less powerful stimulant of smooth muscle. It has practically no stimulant effect on the central nervous system. It was formerly used as a diuretic and in the treatment of angina pectoris and hypertension. (From Martindale, The Extra Pharmacopoeia, 30th ed, pp1318-9). theobromine : A dimethylxanthine having the two methyl groups located at positions 3 and 7. A purine alkaloid derived from the cacao plant, it is found in chocolate, as well as in a number of other foods, and is a vasodilator, diuretic and heart stimulator.	7.21	1	0	dimethylxanthine	adenosine receptor antagonist; bronchodilator agent; food component; human blood serum metabolite; mouse metabolite; plant metabolite; vasodilator agent
thiabendazole Tresaderm: dermatologic soln containing dexamethasone, thiabendazole & neomycin sulfate	7.25	1	0	1,3-thiazoles; benzimidazole fungicide; benzimidazoles	antifungal agrochemical; antinematodal drug
thiram Thiram: A dithiocarbamate chemical, used commercially in the rubber processing industry and as a fungicide. In vivo studies indicate that it inactivates the enzyme GLUTATHIONE REDUCTASE. It has mutagenic activity and may induce chromosomal aberrations.. thiram : An organic disulfide that results from the formal oxidative dimerisation of N,N-dimethyldithiocarbamic acid. It is widely used as a fungicidal seed treatment.	2.9	3	0	organic disulfide	antibacterial drug; antifungal agrochemical; antiseptic drug
triamterene Triamterene: A pteridinetriamine compound that inhibits SODIUM reabsorption through SODIUM CHANNELS in renal EPITHELIAL CELLS.. triamterene : Pteridine substituted at positions 2, 4 and 7 with amino groups and at position 6 with a phenyl group. A sodium channel blocker, it is used as a diuretic in the treatment of hypertension and oedema.	2.79	3	0	pteridines	diuretic; sodium channel blocker
trimethoprim Trimethoprim: A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM, SULFAMETHOXAZOLE DRUG COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported.. trimethoprim : An aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge.	2.52	2	0	aminopyrimidine; methoxybenzenes	antibacterial drug; diuretic; drug allergen; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; environmental contaminant; xenobiotic
urethane [no description available]	3.46	2	0	carbamate ester	fungal metabolite; mutagen
thymidine [no description available]	7.41	1	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
benzimidazole 1H-benzimidazole : The 1H-tautomer of benzimidazole.	2.1	1	0	benzimidazole; polycyclic heteroarene
triethylenemelamine Triethylenemelamine: Toxic alkylating agent used in industry; also as antineoplastic and research tool to produce chromosome aberrations and cancers.	3.43	8	0	1,3,5-triazines	alkylating agent; insect sterilant
hydroxyproline Hydroxyproline: A hydroxylated form of the imino acid proline. A deficiency in ASCORBIC ACID can result in impaired hydroxyproline formation.. hydroxyproline : A proline derivative that is proline substituted by at least one hydroxy group.	7.47	2	0	4-hydroxyproline; L-alpha-amino acid zwitterion	human metabolite; mouse metabolite; plant metabolite
thyroxine Thyroxine: The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (MONOIODOTYROSINE) and the coupling of iodotyrosines (DIIODOTYROSINE) in the THYROGLOBULIN. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form TRIIODOTHYRONINE which exerts a broad spectrum of stimulatory effects on cell metabolism.. thyroxine : An iodothyronine compound having iodo substituents at the 3-, 3'-, 5- and 5'-positions.	1.93	1	0	2-halophenol; iodophenol; L-phenylalanine derivative; non-proteinogenic L-alpha-amino acid; thyroxine zwitterion; thyroxine	antithyroid drug; human metabolite; mouse metabolite; thyroid hormone
lysine Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.	7.13	1	0	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
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.	1.93	1	0	pseudohalide anion	EC 1.9.3.1 (cytochrome c oxidase) inhibitor
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	9.2	4	0	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
2,3,4,6-tetrachlorophenol 2,3,4,6-tetrachlorophenol: RN given refers to parent cpd; see also record for tetrachlorophenol with locants for chloro groups not specified. 2,3,4,6-tetrachlorophenol : A tetrachlorophenol in which the chlorines are located at positions 2, 3, 4, and 6.	2.21	1	0	tetrachlorophenol	xenobiotic metabolite
galactose galactopyranose : The pyranose form of galactose.	2.08	1	0	D-galactose; galactopyranose	Escherichia coli metabolite; mouse metabolite
edetic acid Edetic Acid: A chelating agent that sequesters a variety of polyvalent cations such as CALCIUM. It is used in pharmaceutical manufacturing and as a food additive.	2.17	1	0	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
cysteamine Cysteamine: A mercaptoethylamine compound that is endogenously derived from the COENZYME A degradative pathway. The fact that cysteamine is readily transported into LYSOSOMES where it reacts with CYSTINE to form cysteine-cysteamine disulfide and CYSTEINE has led to its use in CYSTINE DEPLETING AGENTS for the treatment of CYSTINOSIS.. cysteamine : An amine that consists of an ethane skeleton substituted with a thiol group at C-1 and an amino group at C-2.	2.78	3	0	amine; thiol	geroprotector; human metabolite; mouse metabolite; radiation protective agent
methylene blue Methylene Blue: A compound consisting of dark green crystals or crystalline powder, having a bronze-like luster. Solutions in water or alcohol have a deep blue color. Methylene blue is used as a bacteriologic stain and as an indicator. It inhibits GUANYLATE CYCLASE, and has been used to treat cyanide poisoning and to lower levels of METHEMOGLOBIN.. methylene blue : An organic chloride salt having 3,7-bis(dimethylamino)phenothiazin-5-ium as the counterion. A commonly used dye that also exhibits antioxidant, antimalarial, antidepressant and cardioprotective properties.	3.25	5	0	organic chloride salt	acid-base indicator; antidepressant; antimalarial; antimicrobial agent; antioxidant; cardioprotective agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 4.6.1.2 (guanylate cyclase) inhibitor; fluorochrome; histological dye; neuroprotective agent; physical tracer
lactose Lactose: A disaccharide of GLUCOSE and GALACTOSE in human and cow milk. It is used in pharmacy for tablets, in medicine as a nutrient, and in industry.. lactose : A glycosylglucose disaccharide, found most notably in milk, that consists of D-galactose and D-glucose fragments bonded through a beta-1->4 glycosidic linkage. The glucose fragment can be in either the alpha- or beta-pyranose form, whereas the galactose fragment can only have the beta-pyranose form.. beta-lactose : The beta-anomer of lactose.	9.46	6	0	lactose
1,2-dipalmitoylphosphatidylcholine 1,2-Dipalmitoylphosphatidylcholine: Synthetic phospholipid used in liposomes and lipid bilayers to study biological membranes. It is also a major constituent of PULMONARY SURFACTANTS.	2.44	2	0
phenylalanine Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.	2.05	1	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; phenylalanine; proteinogenic amino acid	algal metabolite; EC 3.1.3.1 (alkaline phosphatase) inhibitor; Escherichia coli metabolite; human xenobiotic metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
barbituric acid barbituric acid: RN given refers to parent cpd; structure from Merck Index, 9th ed, #966. barbituric acid : A barbiturate, the structure of which is that of perhydropyrimidine substituted at C-2, -4 and -6 by oxo groups. Barbituric acid is the parent compound of barbiturate drugs, although it is not itself pharmacologically active.	3.55	8	0	barbiturates	allergen; xenobiotic
chloroform Chloroform: A commonly used laboratory solvent. It was previously used as an anesthetic, but was banned from use in the U.S. due to its suspected carcinogenicity.. chloroform : A one-carbon compound that is methane in which three of the hydrogens are replaced by chlorines.	2.05	1	0	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
dimethyl sulfone [no description available]	3.16	1	0	sulfone
sodium citrate, anhydrous Sodium Citrate: Sodium salts of citric acid that are used as buffers and food preservatives. They are used medically as anticoagulants in stored blood, and for urine alkalization in the prevention of KIDNEY STONES.. sodium citrate : The trisodium salt of citric acid.	2.08	1	0	organic sodium salt	anticoagulant; flavouring agent
ampicillin Ampicillin: Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.. ampicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group.	2.21	1	0	beta-lactam antibiotic; penicillin allergen; penicillin	antibacterial drug
mannitol [no description available]	2.25	1	0	mannitol	allergen; antiglaucoma drug; compatible osmolytes; Escherichia coli metabolite; food anticaking agent; food bulking agent; food humectant; food stabiliser; food thickening agent; hapten; metabolite; osmotic diuretic; sweetening agent
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.	7.21	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
arginine Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.	2.06	1	0	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
ethylene Plastipore: high density polyethylene sponge biocompatible material; used as posts in dental bridges	2.84	4	0	alkene; gas molecular entity	plant hormone; refrigerant
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	3.33	6	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
ethanethiol ethanethiol: RN given refers to parent cpd; structure. ethanethiol : An alkanethiol that is ethane substituted by a thiol group at position 1. It is added to odorless gaseous products such as liquefied petroleum gas (LPG) to provide a garlic scent which helps warn of gas leaks.	2.05	1	0	alkanethiol	rodenticide
trimethylchlorosilane trimethylsilyl chloride: structure in first source. chlorotrimethylsilane : A silyl chloride consisting of a central silicon atom covalently bound to one chloro and three methyl groups. Chlorotrimethylsilane is a derivatisation agent used in gas chromatography/mass spectrometry applications.	2.05	1	0	silyl chloride	chromatographic reagent
trichloroacetic acid Trichloroacetic Acid: A strong acid used as a protein precipitant in clinical chemistry and also as a caustic for removing warts.. trichloroacetic acid : A monocarboxylic acid that is acetic acid in which all three methyl hydrogens are substituted by chlorine.	3.16	5	0	monocarboxylic acid; organochlorine compound	carcinogenic agent; metabolite; mouse metabolite
trifluoroacetic acid Trifluoroacetic Acid: A very strong halogenated derivative of acetic acid. It is used in acid catalyzed reactions, especially those where an ester is cleaved in peptide synthesis.. trifluoroacetic acid : A monocarboxylic acid that is the trifluoro derivative of acetic acid.	2.05	1	0	fluoroalkanoic acid	human xenobiotic metabolite; NMR chemical shift reference compound; reagent
phencyclidine Phencyclidine: A hallucinogen formerly used as a veterinary anesthetic, and briefly as a general anesthetic for humans. Phencyclidine is similar to KETAMINE in structure and in many of its effects. Like ketamine, it can produce a dissociative state. It exerts its pharmacological action through inhibition of NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE). As a drug of abuse, it is known as PCP and Angel Dust.. phencyclidine : A member of the class of piperidines that is piperidine in which the nitrogen is substituted with a 1-phenylcyclohexyl group. Formerly used as an anaesthetic agent, it exhibits both hallucinogenic and neurotoxic effects.	2.94	3	0	benzenes; piperidines	anaesthetic; neurotoxin; NMDA receptor antagonist; psychotropic drug
tromethamine Tromethamine: An organic amine proton acceptor. It is used in the synthesis of surface-active agents and pharmaceuticals; as an emulsifying agent for cosmetic creams and lotions, mineral oil and paraffin wax emulsions, as a biological buffer, and used as an alkalizer. (From Merck, 11th ed; Martindale, The Extra Pharmacopoeia, 30th ed, p1424)	2.07	1	0	primary amino compound; triol	buffer
tetraethoxysilane [no description available]	2.1	1	0
azobis(isobutyronitrile) azobis(isobutyronitrile): blowing agent for elastomers & plastics; initiator for free radical reactions; structure	2.52	2	0
isoprene isoprene: used in manufacture of ''synthetic'' rubber, butyl rubber; copolymer in production of elastomers; structure. isoprene : A hemiterpene with the formula CH2=C(CH3)CH=CH2; the monomer of natural rubber and a common structure motif to the isoprenoids, a large class of other naturally occurring compounds.	2.45	2	0	alkadiene; hemiterpene; volatile organic compound	plant metabolite
trichloroethylene Trichloroethylene: A highly volatile inhalation anesthetic used mainly in short surgical procedures where light anesthesia with good analgesia is required. It is also used as an industrial solvent. Prolonged exposure to high concentrations of the vapor can lead to cardiotoxicity and neurological impairment.. triol : A chemical compound containing three hydroxy groups.	3.31	1	0	chloroethenes	inhalation anaesthetic; mouse metabolite
acrylamide [no description available]	2.53	2	0	acrylamides; N-acylammonia; primary carboxamide	alkylating agent; carcinogenic agent; Maillard reaction product; mutagen; neurotoxin
bisphenol a 4,4'-isopropylidene diphenol: stimulates proliferative responses and cytokine productions of murine spleen cells and thymus cells in vitro. bisphenol : By usage, the methylenediphenols, HOC6H4CH2C6H4OH, commonly p,p-methylenediphenol, and their substitution products (generally derived from condensation of two equivalent amounts of a phenol with an aldehyde or ketone). The term also includes analogues in the the methylene (or substituted methylene) group has been replaced by a heteroatom.. bisphenol A : A bisphenol that is 4,4'-methanediyldiphenol in which the methylene hydrogens are replaced by two methyl groups.	7.54	2	0	bisphenol	endocrine disruptor; environmental contaminant; xenobiotic; xenoestrogen
rhodamine b rhodamine B: RN & N1 from 9th CI Form Index; RN given refers to parent cpd; structure in Merck Index, 9th ed, #7973; TETRAETHYLRHODAMINE was see RHODAMINES 1975-93; use RHODAMINES to search TETRAETHYLRHODAMINE 1975-93. rhodamine B : An organic chloride salt having N-[9-(2-carboxyphenyl)-6-(diethylamino)-3H-xanthen-3-ylidene]-N-ethylethanaminium as the counterion. An amphoteric dye commonly used as a fluorochrome.	7.78	3	0	organic chloride salt; xanthene dye	fluorescent probe; fluorochrome; histological dye
acenaphthene [no description available]	2.41	1	0	acenaphthenes
1-naphthaleneacetic acid 1-naphthaleneacetic acid: a plant growth regulator; RN given refers to parent cpd. naphthylacetic acid : A monocarboxylic acid that is naphthalene substituted by a carboxymethyl group at any position.. 1-naphthaleneacetic acid : A naphthylacetic acid substituted by a carboxymethyl group at position 1.	2.17	1	0	naphthylacetic acid	synthetic auxin
n-vinyl-2-pyrrolidinone N-vinyl-2-pyrrolidinone: monomer of POVIDONE; structure given in first source	2.1	1	0	pyrrolidin-2-ones
tolonium chloride Tolonium Chloride: A phenothiazine that has been used as a hemostatic, a biological stain, and a dye for wool and silk. Tolonium chloride has also been used as a diagnostic aid for oral and gastric neoplasms and in the identification of the parathyroid gland in thyroid surgery.. tolonium chloride : An organic chloride salt having 3-amino-7-(dimethylamino)-2-methylphenothiazin-5-ium (tolonium) as the counterion. It is a blue nuclear counterstain that can be used to demonstrate Nissl substance and is also useful for staining mast cell granules, both in metachromatic and orthochromatic techniques.	2.11	1	0
pyronine Pyronine: Xanthene dye used as a bacterial and biological stain. Synonyms: Pyronin; Pyronine G; Pyronine Y. Use also for Pyronine B. which is diethyl-rather than dimethylamino-.. pyronin Y : An organic chloride salt having 6-(dimethylamino)-N,N-dimethyl-3H-xanthen-3-iminium as the cation. Used with methyl green to selectively demonstrate RNA (red) in contrast to DNA (green) with the Unna-Pappenheim method.	1.97	1	0	iminium salt; organic chloride salt	histological dye
xanthenes Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.	2.25	1	0	xanthene
propylparaben Parabens: Methyl, propyl, butyl, and ethyl esters of p-hydroxybenzoic acid. They have been approved by the FDA as antimicrobial agents for foods and pharmaceuticals. (From Hawley's Condensed Chemical Dictionary, 11th ed, p872)	2.41	1	0	benzoate ester; paraben; phenols	antifungal agent; antimicrobial agent
2-toluidine 2-toluidine: RN given refers to parent cpd. o-toluidine : An aminotoluene in which the amino substituent is ortho to the methyl group.	2.41	1	0	aminotoluene	carcinogenic agent
3,4-dichloroaniline 3,4-dichloroaniline : A dichloroaniline having the two chloro-substituents at the 3- and 4-positions.	2.41	1	0	dichloroaniline	epitope; xenobiotic
2,4-diaminotoluene 2,4-diaminotoluene: RN given refers to unlabeled parent cpd; structure. 2,4-diaminotoluene : An aminotoluene that is para-toluidine with an additional amino group at position 2.	2.05	1	0	aminotoluene	metabolite
ethylene dimethacrylate ethylene glycol dimethacrylate : The enoate ester that is the 1,2-bis(methacryloyl) derivative of ethylene glycol.	3.01	4	0	enoate ester	allergen; cross-linking reagent; polymerisation monomer
furaldehyde Furaldehyde: A heterocyclic compound consisting of a furan where the hydrogen at position 2 is substituted by a formyl group.. furfural : An aldehyde that is furan with the hydrogen at position 2 substituted by a formyl group.	3.86	3	0	aldehyde; furans	Maillard reaction product; metabolite
alpha-resorcylic acid alpha-resorcylic acid: RN given refers to parent cpd. 3,5-dihydroxybenzoic acid : A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 5.	2.05	1	0	dihydroxybenzoic acid; resorcinols	metabolite
3,5-dinitrobenzoic acid 3,5-dinitrobenzoic acid : A member of the class of benzoic acids that is benzoic acid in which the hydrogens at positions 3 and 5 are replaced by nitro groups.	7.1	1	0	benzoic acids; C-nitro compound
4-nitroaniline [no description available]	2.05	1	0	nitroaniline	bacterial xenobiotic metabolite
terephthalic acid terephthalic acid: RN given refers to 1,4-benzenedicarboxylic acid. terephthalic acid : A benzenedicarboxylic acid carrying carboxy groups at positions 1 and 4. One of three possible isomers of benzenedicarboxylic acid, the others being phthalic and isophthalic acids.	8.06	1	0	benzenedicarboxylic acid
styrene Styrene: A colorless, toxic liquid with a strong aromatic odor. It is used to make rubbers, polymers and copolymers, and polystyrene plastics.. styrene : A vinylarene that is benzene carrying a vinyl group. It has been isolated from the benzoin resin produced by Styrax species.	2.53	2	0	styrenes; vinylarene; volatile organic compound	mouse metabolite; mutagen; plant metabolite
4,4'-diaminodiphenylmethane 4,4'-diaminodiphenylmethane: RN given refers to parent cpd; structure. 4,4'-diaminodiphenylmethane : An aromatic amine that is diphenylmethane substituted at the 4-position of each benzene ring by an amino group.	2.52	2	0	aromatic amine	allergen; carcinogenic agent
boric acid [no description available]	2.01	1	0	boric acids	astringent
methylhexaneamine [no description available]	3.23	1	0	alkylamine
caprolactam Caprolactam: Cyclic amide of caproic acid used in manufacture of synthetic fibers of the polyamide type. Can cause local irritation.. epsilon-caprolactam : A member of the class of caprolactams that is azepane substituted by an oxo group at position 2.	7.1	1	0	caprolactams	human blood serum metabolite
4-phenylenediamine 4-phenylenediamine: agent hair dye responsible for contact dermatitis; RN given refers to parent cpd. 1,4-phenylenediamine : A phenylenediamine in which the amino functions are at positions 1 and 4 of the benzene nucleus.	2.25	1	0	phenylenediamine	allergen; dye; hapten; reagent
epichlorohydrin Epichlorohydrin: A chlorinated epoxy compound used as an industrial solvent. It is a strong skin irritant and carcinogen.. epichlorohydrin : An epoxide that is 1,2-epoxypropene in which one of the methyl hydrogens is substituted by chlorine.	2.17	1	0	epoxide; organochlorine compound
glyoxal [no description available]	2.08	1	0	dialdehyde	agrochemical; allergen; pesticide; plant growth regulator
3-toluidine 3-toluidine: RN given refers to parent cpd	2.41	1	0
cyanuric chloride cyanuric chloride : A chloro-1,3,5-triazine in which the triazine ring is substituted on each carbon by chlorine. Its main use is in the preparation of the triazine-class pesticides.	2.44	2	0	chloro-1,3,5-triazine; organochlorine compound	cross-linking reagent
cyanuric acid cyanuric acid: RN given refers to parent cpd. isocyanuric acid : The keto tautomer of cyanuric acid.. cyanuric acid : The enol tautomer of isocyanuric acid.	11.02	169	4	1,3,5-triazinanes; 1,3,5-triazines; heteroaryl hydroxy compound	xenobiotic
n-butylamine n-butylamine: RN given refers to parent cpd. butan-1-amine : A primary aliphatic amine that is butane substituted by an amino group at position 1.	1.98	1	0	primary aliphatic amine
pyrroles 1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.	3.16	1	0	pyrrole; secondary amine
furan furan : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing four carbons and one oxygen, with formula C4H4O. It is a toxic, flammable, low-boiling (31degreeC) colourless liquid.	7.05	1	0	furans; mancude organic heteromonocyclic parent; monocyclic heteroarene	carcinogenic agent; hepatotoxic agent; Maillard reaction product
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	2.76	3	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
n,n'-methylenebisacrylamide [no description available]	2.15	1	0
piperidine [no description available]	2.13	1	0	azacycloalkane; piperidines; saturated organic heteromonocyclic parent; secondary amine	base; catalyst; human metabolite; non-polar solvent; plant metabolite; protic solvent; reagent
1-hexanol 1-hexanol: RN given refers to parent cpd. hexanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of six carbon atoms.. hexan-1-ol : A primary alcohol that is hexane substituted by a hydroxy group at position 1.	2.13	1	0	hexanol; primary alcohol	alarm pheromone; antibacterial agent; fragrance; plant metabolite
diethylene glycol glycol ether : A hydroxyether which contains both an ether and alcohol functional groups. It is one of the most versatile classes of organic solvents which are commonly used in paints, cleaners, adhesives, pharmaceuticals and cosmetics.	2.96	4	0	hydroxyether
dodecylmercaptan dodecylmercaptan: used in polymerization of neoprenes; structure	2.07	1	0
pentaerythritol pentaerythritol: RN given refers to parent cpd; structure in Merck Index, 9th ed, #6904. pentaerythritol : A tetrol that is neopentane in which one of the methyl hydrogens of all four methyl groups are replaced by hydroxy groups. It is a chemical intermediate used in the production of explosives, plastics, paints, appliances, and cosmetics.	2.57	2	0	primary alcohol; tetrol	flame retardant; laxative
diethylhexyl phthalate Diethylhexyl Phthalate: An ester of phthalic acid. It appears as a light-colored, odorless liquid and is used as a plasticizer for many resins and elastomers.. bis(2-ethylhexyl) phthalate : A phthalate ester that is the bis(2-ethylhexyl) ester of benzene-1,2-dicarboxylic acid.	9.41	6	0	diester; phthalate ester	androstane receptor agonist; apoptosis inhibitor; plasticiser
framycetin Framycetin: A component of NEOMYCIN that is produced by Streptomyces fradiae. On hydrolysis it yields neamine and neobiosamine B. (From Merck Index, 11th ed). framycetin : A tetracyclic antibacterial agent derived from neomycin, being a glycoside ester of neamine and neobiosamine B.	1.92	1	0	aminoglycoside	allergen; antibacterial drug; Escherichia coli metabolite
dimethyl 4-phthalate dimethyl 4-phthalate: solvent; structure. dimethyl terephthalate : A diester resulting from the formal condensation of the carboxy groups of terephthalic acid with methanol. It is a primary ingredient widely used in the manufacture of polyesters and industrial plastics.	3.06	1	0	diester; methyl ester; phthalate ester
2-naphthol 2-naphthol: RN given refers to parent cpd. 2-naphthol : A naphthol carrying a hydroxy group at position 2.. naphthols : Any hydroxynaphthalene derivative that has a single hydroxy substituent.	2.1	1	0	naphthol	antinematodal drug; genotoxin; human urinary metabolite; human xenobiotic metabolite; mouse metabolite; radical scavenger
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	2.11	1	0	acetate ester; ethyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; metabolite; polar aprotic solvent; Saccharomyces cerevisiae metabolite
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.	6.93	1	0	cyanide salt; one-carbon compound; sodium salt	EC 1.15.1.1 (superoxide dismutase) inhibitor
diphenhydramine hydrochloride Antitussive Agents: Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally.. diphenhydramine hydrochloride : The hydrochloride salt of diphenhydramine.	2.04	1	0	hydrochloride; organoammonium salt	anti-allergic agent; antiemetic; antiparkinson drug; antipruritic drug; H1-receptor antagonist; local anaesthetic; muscarinic antagonist; sedative
aziridine [no description available]	1.92	1	0	azacycloalkane; aziridines; saturated organic heteromonocyclic parent	alkylating agent
catechin Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.	7.11	1	0	catechin	antioxidant; plant metabolite
perylene Perylene: A 20-carbon dibenz(de,kl)anthracene that can be viewed as a naphthalene fused to a phenalene or as dinaphthalene. It is used as fluorescent lipid probe in the cytochemistry of membranes and is a polycyclic hydrocarbon pollutant in soil and water. Derivatives may be carcinogenic.. perylene : An ortho- and peri-fused polycyclic arene comprising of five benzene rings that is anthracene in which the d,e and k,l sides are fused to benzene rings.	8.54	8	0	ortho- and peri-fused polycyclic arene; perylenes
acenaphthylene acenaphthylene: RN given refers to parent cpd. acenaphthylene : A ortho- and peri-fused tricyclic hydrocarbon that occurs in coal tar.	2.41	1	0	acenaphthylenes; ortho- and peri-fused polycyclic arene; ortho- and peri-fused tricyclic hydrocarbon
thiazoles [no description available]	3.83	3	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
pyrimidine pyrimidine : The parent compound of the pyrimidines; a diazine having the two nitrogens at the 1- and 3-positions.	3.12	1	0	diazine; pyrimidines	Daphnia magna metabolite
hydrazine diamine : Any polyamine that contains two amino groups.	2.1	1	0	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
perfluorooctanoic acid perfluorooctanoic acid: RN given refers to parent cpd. perfluorooctanoic acid : A fluoroalkanoic acid that is perfluorinated octanoic acid.	7.25	1	0	fluoroalkanoic acid	carcinogenic agent; endocrine disruptor; environmental contaminant; surfactant; xenobiotic
cyanamide Cyanamide: A cyanide compound which has been used as a fertilizer, defoliant and in many manufacturing processes. It often occurs as the calcium salt, sometimes also referred to as cyanamide. The citrated calcium salt is used in the treatment of alcoholism.. cyanamide : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by an amino group.	7.73	3	0	nitrile; one-carbon compound	EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor
cyanogen cyanogen: structure. oxalonitrile : A dinitrile that is ethane substituted by two cyano groups.	3.95	11	0	dinitrile; pseudohalogen
dicyandiamido dicyandiamido: RN given refers to parent cpd; structure. cyanoguanidine : A guanidine in which one of the amino hydrogens of guanidine itself is substituted by a cyano group. It is used in the manufacture of fertilizers, pharmaceuticals, explosives, oil well drilling muds, and dyestuffs.	3.82	10	0	guanidines; nitrile	curing agent; explosive; fertilizer; flame retardant; nitrification inhibitor
cyanogen bromide Cyanogen Bromide: Cyanogen bromide (CNBr). A compound used in molecular biology to digest some proteins and as a coupling reagent for phosphoroamidate or pyrophosphate internucleotide bonds in DNA duplexes.	1.99	1	0
luminol Luminol: 5-Amino-2,3-dihydro-1,4-phthalazinedione. Substance that emits light on oxidation. It is used in chemical determinations.	7.05	1	0
methoxyhydroxyphenylglycol Methoxyhydroxyphenylglycol: Synthesized from endogenous epinephrine and norepinephrine in vivo. It is found in brain, blood, CSF, and urine, where its concentrations are used to measure catecholamine turnover.	2.06	1	0	methoxybenzenes; phenols
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	3.71	9	0	dialdehyde	biomarker
hematoporphyrin Hematoporphyrins: Iron-free derivatives of heme with 4 methyl groups, 2 hydroxyethyl groups and 2 propionic acid groups attached to the pyrrole rings. Some of these PHOTOSENSITIZING AGENTS are used in the PHOTOTHERAPY of malignant NEOPLASMS.. hematoporphyrin : A dicarboxylic acid that is protoporphyrin in which the vinyl groups at positions 7 and 12 are replaced by 1-hydroxyethyl groups.	2.11	1	0
3-nitrophenol [no description available]	2.1	1	0	3-nitrophenols
trimesic acid trimesic acid: RN given refers to parent cpd. benzene-1,3,5-tricarboxylic acid : A tricarboxylic acid that consists of benzene substituted by carboxy groups at positions 1, 3 and 5.	2.52	2	0	benzoic acids; tricarboxylic acid
glycidol glycidol: structure given in first source	2.1	1	0	epoxide; primary alcohol
malachite green malachite green: RN given refers to parent cpd; structure. malachite green : An organic chloride salt that is the monochloride salt of malachite green cation. Used as a green-coloured dye, as a counter-stain in histology, and for its anti-fungal properties in aquaculture.	2.21	1	0	organic chloride salt	antibacterial agent; antifungal drug; carcinogenic agent; environmental contaminant; fluorochrome; histological dye; teratogenic agent
c.i. 42510 Rosaniline Dyes: Compounds that contain the triphenylmethane aniline structure found in rosaniline. Many of them have a characteristic magenta color and are used as COLORING AGENTS.. basic fuchsin : A four-component mixture of chemically related dyes comprising pararosanilin, rosanilin, magenta II and new fuchsin in varying amounts. rosanilin : A hydrochloride that is the monohydrochloride of 4-[(4-aminophenyl)(4-iminocyclohexa-2,5-dien-1-ylidene)methyl]-2-methylaniline. One of the major constituents of Basic fuchsin, together with pararosanilin, magenta II and new fuchsin.	2.59	2	0
ammelide ammelide: structure given in first source; RN given refers to parent cpd	4.22	16	0	dihydroxy-1,3,5-triazine; monoamino-1,3,5-triazine
tetramethoxysilane [no description available]	2.17	1	0
ethylnitrosourea Ethylnitrosourea: A nitrosourea compound with alkylating, carcinogenic, and mutagenic properties.. N-ethyl-N-nitrosourea : A member of the class of N-nitrosoureas that is urea in which one of the nitrogens is substituted by ethyl and nitroso groups.	2.11	1	0	N-nitrosoureas	alkylating agent; carcinogenic agent; genotoxin; mutagen
1-phenylazo-2-naphthol 1-phenylazo-2-naphthol: RN given refers to cpd without isomeric designation	2.1	1	0
potassium citrate Potassium Citrate: A powder that dissolves in water, which is administered orally, and is used as a diuretic, expectorant, systemic alkalizer, and electrolyte replenisher.. potassium citrate (anhydrous) : The anhydrous form of the tripotassium salt of citric acid.	2.47	2	0	potassium salt	diuretic
rhodamine 6g rhodamine 6G: RN given refers to HCl	3.49	7	0
2,4,6-triaminopyrimidine 2,4,6-triaminopyrimidine: see also 2,4,6-triaminopyridinium (cation). 2,4,6-triaminopyrimidine : An aminopyrimidine in which a pyrimidine core carries amino substituents at positions 2, 4 and 6.	2.11	1	0	aminopyrimidine
methyltrimethoxysilane [no description available]	2.49	2	0
4-aminothiophenol [no description available]	2.11	1	0
cadmium sulfide [no description available]	2.07	1	0	cadmium molecular entity
manganese dioxide [no description available]	2.13	1	0	manganese molecular entity; metal oxide
zinc oxide Zinc Oxide: A mild astringent and topical protectant with some antiseptic action. It is also used in bandages, pastes, ointments, dental cements, and as a sunblock.	2.91	3	0	zinc molecular entity
molybdenum disulfide [no description available]	7.57	2	0	sulfide salt
ammonium hydroxide Ammonium Hydroxide: The hydroxy salt of ammonium ion. It is formed when AMMONIA reacts with water molecules in solution.. ammonium hydroxide : A solution of ammonia in water.	2.05	1	0	inorganic hydroxy compound	food acidity regulator
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	2.5	2	0	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
n-(1-naphthyl)ethylenediamine N-(1-naphthyl)ethylenediamine : An N-substituted ethylenediamine compound having 1-naphthyl as the substituent.	2.13	1	0	N-substituted diamine
spectinomycin Spectinomycin: An antibiotic produced by Streptomyces spectabilis. It is active against gram-negative bacteria and used for the treatment of GONORRHEA.. spectinomycin dihydrochloride : A hydrochloride obtained by combining spectinomycin with two molar equivalents of hydrochloric acid. An antibiotic that is active against gram-negative bacteria and used (as its pentahydrate) to treat gonorrhea.. spectinomycin : A pyranobenzodioxin and antibiotic that is active against gram-negative bacteria and used (as its dihydrochloride pentahydrate) to treat gonorrhea. It is produced by the bacterium Streptomyces spectabilis.	7.17	1	0	cyclic acetal; cyclic hemiketal; cyclic ketone; pyranobenzodioxin; secondary alcohol; secondary amino compound	antibacterial drug; antimicrobial agent; bacterial metabolite
fluorescein Fluorescein: A phthalic indicator dye that appears yellow-green in normal tear film and bright green in a more alkaline medium such as the aqueous humor.. fluorescein (lactone form) : A xanthene dye that is highly fluorescent, detectable even when present in minute quantities. Used forensically to detect traces of blood, in analytical chemistry as an indicator in silver nitrate titrations and in microscopy.	2.49	2	0	2-benzofurans; gamma-lactone; organic heteropentacyclic compound; oxaspiro compound; polyphenol; xanthene dye	fluorescent dye; radioopaque medium
3-(trimethoxysilyl)propyl methacrylate 3-(trimethoxysilyl)propyl methacrylate: structure in first source	2.11	1	0
octogen octogen: an explosive compound, contaminant in waste water; structure given in third source. octogen : A tetrazocane that is 1,3,5,7-tetrazocane in which the hydrogen atom attached to each of the nitrogens is replaced by a nitro group.	2.41	1	0	N-nitro compound; tetrazocane	explosive
1,12-dodecamethylenediamine 1,12-dodecamethylenediamine: RN given refers to parent cpd. dodecane-1,12-diamine : An alkane-alpha,omega-diamine that is dodecane substituted by amino groups at positions 1 and 12.	2.06	1	0	alkane-alpha,omega-diamine
2-(dimethylamino)ethyl methacrylate 2-(dimethylamino)ethyl methacrylate: reducing agent; structure given in first source	2.31	1	0
ici resin fs3798 [no description available]	2.05	1	0
sudan red [no description available]	2.07	1	0
2,2-bis(bromomethyl)-1,3-propanediol 2,2-bis(bromomethyl)-1,3-propanediol: structure given in first source	2.1	1	0	primary alcohol
fluorescein-5-isothiocyanate Fluorescein-5-isothiocyanate: Fluorescent probe capable of being conjugated to tissue and proteins. It is used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.. fluorescein 5-isothiocyanate : The 5-isomer of fluorescein isothiocyanate. Acts as a fluorescent probe capable of being conjugated to tissue and proteins; used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.	2.47	2	0	fluorescein isothiocyanate
dithiothreitol 1,4-dimercaptobutane-2,3-diol : A glycol that is butane-2,3-diol in which a hydrogen from each of the methyl groups is replaced by a thiol group.. 1,4-dithiothreitol : The threo-diastereomer of 1,4-dimercaptobutane-2,3-diol.	2.44	2	0	1,4-dimercaptobutane-2,3-diol; butanediols; dithiol; glycol; thiol	chelator; human metabolite; reducing agent
butylhydroxybutylnitrosamine Butylhydroxybutylnitrosamine: A substituted carcinogenic nitrosamine.. N-butyl-N-(4-hydroxybutyl)nitrosamine : A nitrosamine that has butyl and 4-hydroxybutyl substituents. In mice, it causes high-grade, invasive cancers in the urinary bladder, but not in any other tissues.	2.74	3	0	nitrosamine; primary alcohol	carcinogenic agent
mono-(2-ethylhexyl)phthalate mono-(2-ethylhexyl)phthalate: RN given refers to parent cpd. mono(2-ethylhexyl) phthalate : The mono(2-ethylhexyl) ester of benzene-1,2-dicarboxylic acid.	2.41	1	0	phthalic acid monoester
coralyne coralyne: RN given refers to parent cpd; at this time it is not known for which salt NSC-154890 is synonym; structure; DNA topoisomerse antagonist	7.1	1	0	isoquinolines
lanthanum [no description available]	2.11	1	0	f-block element atom; lanthanoid atom; scandium group element atom
manganese Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.	2.11	1	0	elemental manganese; manganese group element atom	Escherichia coli metabolite; micronutrient
mercury Mercury: A silver metallic element that exists as a liquid at room temperature. It has the atomic symbol Hg (from hydrargyrum, liquid silver), atomic number 80, and atomic weight 200.59. Mercury is used in many industrial applications and its salts have been employed therapeutically as purgatives, antisyphilitics, disinfectants, and astringents. It can be absorbed through the skin and mucous membranes which leads to MERCURY POISONING. Because of its toxicity, the clinical use of mercury and mercurials is diminishing.. mercury(0) : Elemental mercury of oxidation state zero.	3.76	9	0	elemental mercury; zinc group element atom	neurotoxin
molybdenum Molybdenum: A metallic element with the atomic symbol Mo, atomic number 42, and atomic weight 95.95. It is an essential trace element, being a component of the enzymes xanthine oxidase, aldehyde oxidase, and nitrate reductase.	7.57	2	0	chromium group element atom	micronutrient
neodymium Neodymium: An element of the rare earth family of metals. It has the atomic symbol Nd, atomic number 60, and atomic weight 144.24, and is used in industrial applications.	2.05	1	0	f-block element atom; lanthanoid atom
palladium Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.	2.1	1	0	metal allergen; nickel group element atom; platinum group metal atom
platinum Platinum: A heavy, soft, whitish metal, resembling tin, with atomic number 78, atomic weight 195.084, symbol Pt. It is used in manufacturing equipment for laboratory and industrial use. It occurs as a black powder (platinum black) and as a spongy substance (spongy platinum) and may have been known in Pliny's time as alutiae.	3.56	2	0	elemental platinum; nickel group element atom; platinum group metal atom
ruthenium Ruthenium: A hard, brittle, grayish-white rare earth metal with an atomic symbol Ru, atomic number 44, and atomic weight 101.07. It is used as a catalyst and hardener for PLATINUM and PALLADIUM.	2.06	1	0	iron group element atom; platinum group metal atom
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.	5.54	60	0	copper group element atom; elemental silver	Escherichia coli metabolite
titanium Titanium: A dark-gray, metallic element of widespread distribution but occurring in small amounts with atomic number, 22, atomic weight, 47.867 and symbol, Ti; specific gravity, 4.5; used for fixation of fractures.	8.27	5	0	titanium group element atom
tungsten Tungsten: A metallic element with the atomic symbol W, atomic number 74, and atomic weight 183.85. It is used in many manufacturing applications, including increasing the hardness, toughness, and tensile strength of steel; manufacture of filaments for incandescent light bulbs; and in contact points for automotive and electrical apparatus.	2.06	1	0	chromium group element atom	micronutrient
argon Argon: A noble gas with the atomic symbol Ar, atomic number 18, and atomic weight 39.948. It is used in fluorescent tubes and wherever an inert atmosphere is desired and nitrogen cannot be used.	2.1	1	0	monoatomic argon; noble gas atom; p-block element atom	food packaging gas; neuroprotective agent
cadmium Cadmium: An element with atomic symbol Cd, atomic number 48, and atomic weight 112.41. It is a metal and ingestion will lead to CADMIUM POISONING.. elemental cadmium : An element in the zinc group of the periodic table with atomic number 48, atomic mass 112, M.P. 321degreeC, and B.P. 765degreeC). An odourless, tasteless, and highly poisonous soft, ductile, lustrous metal with electropositive properties. It has eight stable isotopes: (106)Cd, (108)Cd,(110)Cd, (111)Cd, (112)Cd, (113)Cd, (114)Cd and (116)Cd, with (112)Cd and (114)Cd being the most common.	3.88	3	0	cadmium molecular entity; zinc group element atom
cerium Cerium: An element of the rare earth family of metals. It has the atomic symbol Ce, atomic number 58, and atomic weight 140.12. Cerium is a malleable metal used in industrial applications.	2.15	1	0	f-block element atom; lanthanoid atom
chromium Chromium: A trace element that plays a role in glucose metabolism. It has the atomic symbol Cr, atomic number 24, and atomic weight 52. According to the Fourth Annual Report on Carcinogens (NTP85-002,1985), chromium and some of its compounds have been listed as known carcinogens.. chromium ion : An chromium atom having a net electric charge.. chromium atom : A chromium group element atom that has atomic number 24.	2.05	1	0	chromium group element atom; metal allergen	micronutrient
erbium Erbium: Erbium. An element of the rare earth family of metals. It has the atomic symbol Er, atomic number 68, and atomic weight 167.26.	2.1	1	0	f-block element atom; lanthanoid atom
europium Europium: An element of the rare earth family of metals. It has the atomic symbol Eu, atomic number 63, and atomic weight 152. Europium is used in the form of its salts as coatings for cathode ray tubes and in the form of its organic derivatives as shift reagents in NMR spectroscopy.	2.15	1	0	f-block element atom; lanthanoid atom
gold Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.	6	97	0	copper group element atom; elemental gold
vanadium Vanadium: A metallic element with the atomic symbol V, atomic number 23, and atomic weight 50.94. It is used in the manufacture of vanadium steel. Prolonged exposure can lead to chronic intoxication caused by absorption usually via the lungs.	7.15	1	0	elemental vanadium; vanadium group element atom	micronutrient
ytterbium Ytterbium: An element of the rare earth family of metals. It has the atomic symbol Yb, atomic number 70, and atomic weight 173. Ytterbium has been used in lasers and as a portable x-ray source.	2.1	1	0	f-block element atom; lanthanoid atom
yttrium Yttrium: An element of the rare earth family of metals. It has the atomic symbol Y, atomic number 39, and atomic weight 88.91. In conjunction with other rare earths, yttrium is used as a phosphor in television receivers and is a component of the yttrium-aluminum garnet (YAG) lasers.	2.1	1	0	d-block element atom; rare earth metal atom; scandium group element atom
zirconium Zirconium: A rather rare metallic element with atomic number 40, atomic weight 91.224, and symbol Zr.	2.78	3	0	titanium group element atom
californium Californium: A man-made radioactive actinide with atomic symbol Cf, atomic number 98, and atomic weight 251. Its valence can be +2 or +3. Californium has medical use as a radiation source for radiotherapy.	2.02	1	0	actinoid atom; f-block element atom
acetylglucosamine Acetylglucosamine: The N-acetyl derivative of glucosamine.. N-acetyl-beta-D-glucosamine : An N-acetyl-D-glucosamine having beta-configuration at the anomeric centre.	2.02	1	0	N-acetyl-D-glucosamine	epitope
phosphoric acid, trisodium salt [no description available]	2.05	1	0	sodium phosphate
hypochlorous acid Hypochlorous Acid: An oxyacid of chlorine (HClO) containing monovalent chlorine that acts as an oxidizing or reducing agent.. hypochlorous acid : A chlorine oxoacid with formula HOCl; a weak, unstable acid, it is the active form of chlorine in water.	2.44	2	0	chlorine oxoacid; reactive oxygen species	EC 2.5.1.18 (glutathione transferase) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; human metabolite
barium sulfate Barium Sulfate: A compound used as an x-ray contrast medium that occurs in nature as the mineral barite. It is also used in various manufacturing applications and mixed into heavy concrete to serve as a radiation shield.. barium sulfate : A metal sulfate with formula BaO4S. Virtually insoluble in water at room temperature, it is mostly used as a component in oil well drilling fluid it occurs naturally as the mineral barite.	2.25	1	0	barium salt; inorganic barium salt; metal sulfate	radioopaque medium
zinc sulfate Zinc Sulfate: A compound given in the treatment of conditions associated with zinc deficiency such as acrodermatitis enteropathica. Externally, zinc sulfate is used as an astringent in lotions and eye drops. (Reynolds JEF(Ed): Martindale: The Extra Pharmacopoeia (electronic version). Micromedex, Inc, Englewood, CO, 1995). zinc sulfate : A metal sulfate compound having zinc(2+) as the counterion.	2.1	1	0	metal sulfate; zinc molecular entity	fertilizer
sodium sulfate [no description available]	2.05	1	0	inorganic sodium salt
bromic acid [no description available]	2.15	1	0	bromine oxoacid
tricalcium phosphate tricalcium phosphate: a form of tricalcium phosphate used as bioceramic bone replacement material; see also records for alpha-tricalcium phosphate, beta-tricalcium phosphate, calcium phosphate; apatitic tricalcium phosphate Ca9(HPO4)(PO4)5(OH) is the calcium orthophosphate leading to beta tricalcium phosphate Ca3(PO4)2 (b-TCP). calcium phosphate : A calcium salt composed of calcium and phosphate/diphosphate ions; present in milk and used for the mineralisation of calcified tissues.	2.21	1	0	calcium phosphate
calcium sulfate Calcium Sulfate: A calcium salt that is used for a variety of purposes including: building materials, as a desiccant, in dentistry as an impression material, cast, or die, and in medicine for immobilizing casts and as a tablet excipient. It exists in various forms and states of hydration. Plaster of Paris is a mixture of powdered and heat-treated gypsum.	2.69	3	0	calcium salt; inorganic calcium salt
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	2.05	1	0	dihydrogen
fluorine Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.	2.41	1	0	diatomic fluorine; gas molecular entity	NMR chemical shift reference compound
fluorosulfonic acid perfluorosulfonic acid: sulfonated tetrafluoroethylene-based fluoropolymer–copolymer	2.84	3	0	sulfur oxoacid	NMR solvent
ozone Ozone: The unstable triatomic form of oxygen, O3. It is a powerful oxidant that is produced for various chemical and industrial uses. Its production is also catalyzed in the ATMOSPHERE by ULTRAVIOLET RAY irradiation of oxygen or other ozone precursors such as VOLATILE ORGANIC COMPOUNDS and NITROGEN OXIDES. About 90% of the ozone in the atmosphere exists in the stratosphere (STRATOSPHERIC OZONE).. ozone : An elemental molecule with formula O3. An explosive, pale blue gas (b.p. -112degreeC) that has a characteristic, pungent odour, it is continuously produced in the upper atmosphere by the action of solar ultraviolet radiation on atmospheric oxygen. It is an antimicrobial agent used in the production of bottled water, as well as in the treatment of meat, poultry and other foodstuffs.	2.07	1	0	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
ferric nitrate ferric nitrate: RN given refers to Fe(+3) salt	2.07	1	0
carbendazim carbendazim: carcinogen when combined with sodium nitrite; principle metabolite of thiophanate methyl & benomyl; structure. carbendazim : A member of the class of benzimidazoles that is 2-aminobenzimidazole in which the primary amino group is substituted by a methoxycarbonyl group. A fungicide, carbendazim controls Ascomycetes, Fungi Imperfecti, and Basidiomycetes on a wide variety of crops, including bananas, cereals, cotton, fruits, grapes, mushrooms, ornamentals, peanuts, sugarbeet, soybeans, tobacco, and vegetables.	7.25	1	0	benzimidazole fungicide; benzimidazoles; benzimidazolylcarbamate fungicide; carbamate ester	antifungal agrochemical; antinematodal drug; metabolite; microtubule-destabilising agent
ammonium chloride Ammonium Chloride: An acidifying agent that has expectorant and diuretic effects. Also used in etching and batteries and as a flux in electroplating.. ammonium chloride : An inorganic chloride having ammonium as the counterion.	2.21	1	0	ammonium salt; inorganic chloride	ferroptosis inhibitor
titanium dioxide titanium dioxide: used medically as protectant against externally caused irritation & sunlight; high concentrations of dust may cause irritation to respiratory tract; RN given refers to titanium oxide (TiO2); structure. titanium dioxide : A titanium oxide with the formula TiO2. A naturally occurring oxide sourced from ilmenite, rutile and anatase, it has a wide range of applications.	2.82	3	0	titanium oxides	food colouring
salen disalicylaldehyde ethylenediamine: reagents for determination of iron	7.05	1	0
fluorides [no description available]	3.64	2	0	halide anion; monoatomic fluorine
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	2.73	3	0	benzenes; phenyl acetates
tetrachloroethylene Tetrachloroethylene: A chlorinated hydrocarbon used as an industrial solvent and cooling liquid in electrical transformers. It is a potential carcinogen.	3.31	1	0	chlorocarbon; chloroethenes	nephrotoxic agent
pyrene pyrene: structure in Merck Index, 9th ed, #7746. pyrene : An ortho- and peri-fused polycyclic arene consisting of four fused benzene rings, resulting in a flat aromatic system.	2.53	2	0	ortho- and peri-fused polycyclic arene	fluorescent probe; persistent organic pollutant
calcium oxalate Calcium Oxalate: The calcium salt of oxalic acid, occurring in the urine as crystals and in certain calculi.. calcium oxalate : The calcium salt of oxalic acid, which in excess in the urine may lead to formation of oxalate calculi (kidney stones).	8.32	6	0	organic calcium salt
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	2.5	2	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	2.41	1	0	pseudohalide anion	mitochondrial respiratory-chain inhibitor
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	7.04	1	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid [no description available]	2.07	1	0	chromanol; monocarboxylic acid; phenols	antioxidant; ferroptosis inhibitor; neuroprotective agent; radical scavenger; Wnt signalling inhibitor
3,3',5,5'-tetramethylbenzidine T1023: radioprotective NO-Synthase Inhibitor	2.15	1	0
captopril Captopril: A potent and specific inhibitor of PEPTIDYL-DIPEPTIDASE A. It blocks the conversion of ANGIOTENSIN I to ANGIOTENSIN II, a vasoconstrictor and important regulator of arterial blood pressure. Captopril acts to suppress the RENIN-ANGIOTENSIN SYSTEM and inhibits pressure responses to exogenous angiotensin.. captopril : A L-proline derivative in which L-proline is substituted on nitrogen with a (2S)-2-methyl-3-sulfanylpropanoyl group. It is used as an anti-hypertensive ACE inhibitor drug.	2.01	1	0	alkanethiol; L-proline derivative; N-acylpyrrolidine; pyrrolidinemonocarboxylic acid	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
cyromazine cyromazine: RN given refers to parent cpd	4.92	34	0	triamino-1,3,5-triazine	mouse metabolite; triazine insecticide
metsulfuron methyl metsulfuron methyl : A N-sulfonylurea in which the sulfonyl group is attached to a 2-(methoxycarbonyl)phenyl group while a (4-methoxy-6-methyl-1,3,5-triazin-2-yl group replaces one of the amino hydrogens of the remaining urea group.	1.92	1	0	1,3,5-triazines; benzoate ester; N-sulfonylurea	environmental contaminant; herbicide; xenobiotic
bambuterol bambuterol: selective inhibitor of butyrylcholinesterase & acetylcholinesterase. bambuterol : A carbamate ester that is terbutaline in which both of the phenolic hydroxy groups have been protected as the corresponding N,N-dimethylcarbamates. A long acting beta-adrenoceptor agonist used in the treatment of asthma, it is a prodrug for terbutaline.	7.15	1	0	carbamate ester; phenylethanolamines	anti-asthmatic drug; beta-adrenergic agonist; bronchodilator agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; prodrug; sympathomimetic agent; tocolytic agent
ractopamine ractopamine: veterinary growth stimulant. ractopamine : A diastereoisomeric mixture of approximately equal amounts of all four possible diastereoisomers of 4-(1-hydroxy-2-{[4-(4-hydroxyphenyl)butan-2-yl]amino}ethyl)phenol. A beta-adrenergic agonist, it is used (generally as the hydrochloride salt) as a feed additive for use in pigs and other livestock to promote protein deposition, resulting in leaner meat. The R,R diastereoisomer, butopamine, is responsible for most of the leanness-enhancing effects. While use of ractopamine has been banned in over 120 countries including throughout the EU, in the US it used in an estimated 80% of all beef, pork and turkey production.. 4-(1-hydroxy-2-{[4-(4-hydroxyphenyl)butan-2-yl]amino}ethyl)phenol : A secondary amino compound that is 4-(2-amino-1-hydroxyethyl)phenol in which one of the hydrogens attached to the nitrogen is replaced by a 4-(p-hydroxyphenyl)butan-2-yl group.	7.49	2	0	benzyl alcohols; polyphenol; secondary alcohol; secondary amino compound
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	7.47	2	0	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
florisil Florisil: hard, porous, granular substance used in vitamin analysis, chromatography, & antibiotic processing	7.25	1	0
urea formaldehyde foam urea formaldehyde foam: widely used foam insulation	2.44	2	0
tris(2,2'-bipyridine)ruthenium(II) tris(2,2'-bipyridyl)ruthenium(II): a fluorescent dye; structure in first source	2.49	2	0	ruthenium coordination entity	fluorochrome
n,n-bis(trimethylsilyl)-2,2,2-trifluoroacetamide [no description available]	2.05	1	0
2-acrylamido-2-methylpropanesulfonate 2-acrylamido-2-methylpropanesulfonate: for detection of alkaline phosphatase; RN given refers to parent cpd; do not confuse with AMPS cpd	2.49	2	0	organosulfonic acid
boron nitride [no description available]	2.47	2	0	nitride
benzeneboronic acid [no description available]	2.17	1	0	boronic acids
porphine porphine: structure given in first source	2.13	1	0
3,4,9,10-perylenetetracarboxylic dianhydride [no description available]	2.05	1	0
leucomalachite green [no description available]	2.17	1	0	benzenoid aromatic compound
1,7-phenanthroline [no description available]	2.04	1	0	phenanthroline
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	2.08	1	0	1,2,3-triazole
perfluoro-n-heptanoic acid perfluoroheptanoic acid : A fluoroalkanoic acid that is perfluorinated heptanoic acid.	2.05	1	0	fluoroalkanoic acid	environmental contaminant; xenobiotic
fluindione fluindione: structure	3.16	1	0	cyclic ketone; indanones
enrofloxacin Enrofloxacin: A fluoroquinolone antibacterial and antimycoplasma agent that is used in veterinary practice.. enrofloxacin : A quinolinemonocarboxylic acid that is 1,4-dihydroquinoline-3-carboxylic acid substituted by an oxo group at position 4, a fluoro group at position 6, a cyclopropyl group at position 1 and a 4-ethylpiperazin-1-yl group at position 7. It is a veterinary antibacterial agent used for the treatment of pets.	2.21	1	0	cyclopropanes; N-alkylpiperazine; N-arylpiperazine; organofluorine compound; quinolinemonocarboxylic acid; quinolone	antibacterial agent; antimicrobial agent; antineoplastic agent
6-chlorouracil 6-chlorouracil: radiolabelled with 36Cl	2.11	1	0
perfluorooctane sulfonic acid perfluorooctane-1-sulfonic acid : A perfluoroalkanesulfonic acid that is octane-1-sulfonic acid in which all seventeen of the hydrogens that are attached to carbons hvae been replaced by fluorines.	2.25	1	0	perfluoroalkanesulfonic acid	antilipemic drug; persistent organic pollutant
6-carboxyfluorescein 6-carboxyfluorescein: originally sold as 6-carboxyfluorescein, but commercial product is a mixture of two isomers; correct name is 5(6)-carboxyfluorescein	2.21	1	0	monocarboxylic acid
ribose-5-phosphate ribose-5-phosphate: RN given refers to cpd without isomeric designation	2.13	1	0	D-ribose 5-phosphate
propylsulfonic acid propylsulfonic acid: RN given refers to cpd without locant for propyl moiety	2.06	1	0
3-methyluracil 3-methyluracil : A pyrimidone that is uracil with a methyl group at position 3.	2.11	1	0	nucleobase analogue; pyrimidone	metabolite
t 1982 1,3,4,6,7,8-hexahydro-2H-pyrimido(1,2-a)pyrimidine: structure in first source	2.11	1	0	pyrimidines
cadmium telluride cadmium telluride: used in radiation monitoring device	3	4	0
homocysteine Homocysteine: A thiol-containing amino acid formed by a demethylation of METHIONINE.. homocysteine : A sulfur-containing amino acid consisting of a glycine core with a 2-mercaptoethyl side-chain.. L-homocysteine : A homocysteine that has L configuration.	2.06	1	0	amino acid zwitterion; homocysteine; serine family amino acid	fundamental metabolite; mouse metabolite
melamine cyanurate melamine cyanurate: structure given in first source. melamine cyanurate : A crystalline complex formed from a 1:1 mixture of melamine and cyanuric (isocyanuric) acid, held together by an extensive two-dimensional network of hydrogen bonds between the two compounds.	3.46	7	0
melamine formaldehyde [no description available]	8.18	5	0
mercury cadmium telluride [no description available]	2.17	1	0
1,1'-oxalyldiimidazole 1,1'-oxalyldiimidazole: structure in first source	7.05	1	0
cobalt Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.	2.31	1	0	cobalt group element atom; metal allergen	micronutrient
phosphites Phosphites: Inorganic salts or organic esters of phosphorous acid that contain the (3-)PO3 radical. (From Grant & Hackh's Chemical Dictionary, 5th ed). phosphite(3-) : A trivalent inorganic anion obtained by removal of all three protons from phosphorous acid.	2.13	1	0	phosphite ion; trivalent inorganic anion
5-hydroxydopamine 5-hydroxydopamine: RN given refers to parent cpd	2	1	0	catecholamine
higenamine higenamine: structure; RN given refers to (+-)-isomer	3.23	1	0	norcoclaurine
caprylates Caprylates: Derivatives of caprylic acid. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain a carboxy terminated eight carbon aliphatic structure.. octanoate : A straight-chain saturated fatty acid anion that is the conjugate base of octanoic acid (caprylic acid); believed to block adipogenesis.	2.25	1	0	fatty acid anion 8:0; straight-chain saturated fatty acid anion	human metabolite; Saccharomyces cerevisiae metabolite
carbene carbene: electrically neutral species H2C: and its derivatives, in which the carbon is covalently bonded to two univalent groups of any kind or a divalent group and bears two nonbonding electrons; carbene is the name of the parent hydride :CH2 ; hence, the name dichlorocarbene for :CCl2. However, names for acyclic and cyclic hydrocarbons containing one or more divalent carbon atoms are derived from the name of the corresponding all-4-hydrocarbon using the suffix -ylidene; methylene carbene also available. carbene : The electrically neutral species H2C(2.) and its derivatives, in which the carbon is covalently bonded to two univalent groups of any kind or a divalent group and bears two nonbonding electrons, which may be spin-paired (singlet state) or spin-non-paired (triplet state).	2.04	1	0	carbene; methanediyl
phosphoramide phosphoramide: RN given refers to triamide. phosphoramide : A compound in which one or more of the OH groups of phosphoric acid have been replaced with an amino or substituted amino group. The term is commonly confined to the phosphoric triamides, P(=O)(NR2)3, since replacement of one or two OH groups produces phosphoramidic acids: P(=O)(OH)(NR2)2 , P(=O)(OH)2(NR2).	6.93	1	0
perchlorate perchlorate: the explosive component of rocket fuel; an environmental contaminant that disrupts THYROID HORMONES. perchlorate : A monovalent inorganic anion obtained by deprotonation of perchloric acid.	2.08	1	0	chlorine oxoanion; monovalent inorganic anion
4-mercaptobutyramidine [no description available]	2.13	1	0
ethynylpyridine ethynylpyridine: structure in first source	7.13	1	0
proline Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.	2.47	2	0	amino acid zwitterion; glutamine family amino acid; L-alpha-amino acid; proline; proteinogenic amino acid	algal metabolite; compatible osmolytes; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
aspartylglycine Asp-Gly : A dipeptide composed of L-aspartic acid and glycine joined by a peptide linkage.	2.06	1	0	dipeptide	metabolite
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	2.05	1	0	oxygen hydride; oxygen radical; reactive oxygen species
naphthalenediimide naphthalenediimide: structure in first source	2.04	1	0
3-sulfopropyl methacrylate [no description available]	2.1	1	0
singlet oxygen Singlet Oxygen: An excited state of molecular oxygen generated photochemically or chemically. Singlet oxygen reacts with a variety of biological molecules such as NUCLEIC ACIDS; PROTEINS; and LIPIDS; causing oxidative damages.	7.15	1	0	chalcogen; monoatomic oxygen; nonmetal atom	macronutrient
peroxymonosulfate peroxymonosulfate: oxidizing agent in prevention of tooth discoloration; RN given refers to ion(2-)	2.72	2	0	sulfur oxide; sulfur oxoanion
zinc hematoporphyrin [no description available]	2.06	1	0
tartrazine Tartrazine: An anionic, hydrophilic azo dye with an orange-yellow color used in fabrics, foods and cosmetics, and as a biological stain.. tartrazine : An organic sodium salt which is the trisodium salt of tartrazine acid. A synthetic lemon yellow azo dye used as a food colouring.	7.25	1	0
biotin vitamin B7 : Any member of a group of vitamers that belong to the chemical structural class called biotins that exhibit biological activity against vitamin B7 deficiency. Vitamin B7 deficiency is very rare in individuals who take a normal balanced diet. Foods rich in biotin are egg yolk, liver, cereals, vegetables (spinach, mushrooms) and rice. Symptoms associated with vitamin B7 deficiency include thinning hair, scaly skin rashes around eyes, nose and mouth, and brittle nails. The vitamers include biotin and its ionized and salt forms.	2.06	1	0	biotins; vitamin B7	coenzyme; cofactor; Escherichia coli metabolite; fundamental metabolite; human metabolite; mouse metabolite; nutraceutical; prosthetic group; Saccharomyces cerevisiae metabolite
angiotensin ii Giapreza: injectable form of angiotensin II used to increase blood pressure in adult patients with septic or other distributive shock. Ile(5)-angiotensin II : An angiotensin II that acts on the central nervous system (PDB entry: 1N9V).	2.17	1	0	amino acid zwitterion; angiotensin II	human metabolite
sb 203580 [no description available]	2.07	1	0	imidazoles; monofluorobenzenes; pyridines; sulfoxide	EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector; Hsp90 inhibitor; neuroprotective agent
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	3.16	1	0	divalent inorganic anion; phosphite ion
aflatoxin b1 Aflatoxin B1: A potent hepatotoxic and hepatocarcinogenic mycotoxin produced by the Aspergillus flavus group of fungi. It is also mutagenic, teratogenic, and causes immunosuppression in animals. It is found as a contaminant in peanuts, cottonseed meal, corn, and other grains. The mycotoxin requires epoxidation to aflatoxin B1 2,3-oxide for activation. Microsomal monooxygenases biotransform the toxin to the less toxic metabolites aflatoxin M1 and Q1.. aflatoxin B1 : An aflatoxin having a tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4 and 11.	7.11	1	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
cortisone [no description available]	6.92	1	0	11-oxo steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	human metabolite; mouse metabolite
pyrene-1-aldehyde pyrene-1-aldehyde: RN given refers to cpd with aldehyde group in position 1	2.08	1	0
5-hydroxymethylfurfural 5-hydroxymethylfurfural: has antisickling activity; HMF is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo. 5-hydroxymethylfurfural : A member of the class of furans that is furan which is substituted at positions 2 and 5 by formyl and hydroxymethyl substituents, respectively. Virtually absent from fresh foods, it is naturally generated in sugar-containing foods during storage, and especially by drying or cooking. It is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo.	8.61	2	0	arenecarbaldehyde; furans; primary alcohol	indicator; Maillard reaction product
glycogen glycogen : A polydisperse, highly branched glucan composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage, joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some cumulative alpha(1->6) links also may occur. The branches in glycogen typically contain 8 to 12 glucose residues.	2.15	1	0
hexacyanoferrate iii hexacyanoferrate III: RN given refers to parent cpd	2.05	1	0
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2.91	3	0	cyclodextrin
maleic acid maleic acid: RN given refers to parent cpd(Z)-isomer which is maleic acid; all RR's given refer to (Z)-isomer; (E)-isomer is fumaric acid. maleic acid : A butenedioic acid in which the double bond has cis- (Z)-configuration.	2.08	1	0	butenedioic acid	algal metabolite; mouse metabolite; plant metabolite
arachidonic acid icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.	7.15	1	0	icosa-5,8,11,14-tetraenoic acid; long-chain fatty acid; omega-6 fatty acid	Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite; mouse metabolite
oleic acid Oleic Acid: An unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed). oleic acid : An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.	2.31	1	0	octadec-9-enoic acid	antioxidant; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; mouse metabolite; plant metabolite; solvent
cocaine Cocaine: An alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake.. cocaine : A tropane alkaloid obtained from leaves of the South American shrub Erythroxylon coca.	2.25	1	0	benzoate ester; methyl ester; tertiary amino compound; tropane alkaloid	adrenergic uptake inhibitor; central nervous system stimulant; dopamine uptake inhibitor; environmental contaminant; local anaesthetic; mouse metabolite; plant metabolite; serotonin uptake inhibitor; sodium channel blocker; sympathomimetic agent; vasoconstrictor agent; xenobiotic
benzene-1,3,5-tricarboxamide benzene-1,3,5-tricarboxamide: structure in first source	3.17	1	0
tenofovir tenofovir (anhydrous) : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens is replaced by a [(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(isopropyloxycarbonyloxymethyl) ester (disoproxil ester) prodrug is used as the fumaric acid salt in combination therapy for the treatment of HIV infection.	3.16	1	0	nucleoside analogue; phosphonic acids	antiviral drug; drug metabolite; HIV-1 reverse transcriptase inhibitor
riboflavin vitamin B2 : Any member of a group of vitamers that belong to the chemical structural class called flavins that exhibit biological activity against vitamin B2 deficiency. Symptoms associated with vitamin B2 deficiency include glossitis, seborrhea, angular stomaitis, cheilosis and photophobia. The vitamers include riboflavin and its phosphate derivatives (and includes their salt, ionised and hydrate forms).	3.16	5	0	flavin; vitamin B2	anti-inflammatory agent; antioxidant; cofactor; Escherichia coli metabolite; food colouring; fundamental metabolite; human urinary metabolite; mouse metabolite; photosensitizing agent; plant metabolite
sodium thiocyanate sodium thiocyanate: RN given refers to thiocyanic acid, Na salt. sodium thiocyanate : An organic sodium salt which is the monosodium salt of thiocyanic acid.	2.15	1	0	organic sodium salt
sodium bicarbonate Sodium Bicarbonate: A white, crystalline powder that is commonly used as a pH buffering agent, an electrolyte replenisher, systemic alkalizer and in topical cleansing solutions.	7.48	2	0	one-carbon compound; organic sodium salt	antacid; food anticaking agent
11-mercaptoundecanoic acid [no description available]	7.05	1	0
6-mercapto-1-hexanol [no description available]	2.13	1	0
calix(4)arene calix(4)arene: a cyclophane consisting of four phenolic units linked by methylene groups; structure in first source	2.93	4	0
sinapinic acid sinapinic acid: a matrix for matrix-assisted laser desorption technique for protein MW determination; a constituent of propolis. trans-sinapic acid : A sinapic acid in which the double bond has trans-configuration.	2.06	1	0	sinapic acid	MALDI matrix material; plant metabolite
sesquiterpenes [no description available]	2.6	1	0
cotinine Cotinine: The N-glucuronide conjugate of cotinine is a major urinary metabolite of NICOTINE. It thus serves as a biomarker of exposure to tobacco SMOKING. It has CNS stimulating properties.. (-)-cotinine : An N-alkylpyrrolidine that consists of N-methylpyrrolidinone bearing a pyridin-3-yl substituent at position C-5 (the 5S-enantiomer). It is an alkaloid commonly found in Nicotiana tabacum.	2.41	1	0	N-alkylpyrrolidine; pyridines; pyrrolidin-2-ones; pyrrolidine alkaloid	antidepressant; biomarker; human xenobiotic metabolite; plant metabolite
curcumin Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.	7.25	1	0	aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger
nootkatone nootkatone: RN given refers to cpd without isomeric designation; structure given in first source. (+)-nootkatone : A sesquiterpenoid that is 4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one which is substituted by methyl groups at positions 4 and 4a, and by an isopropenyl group at position 6 (the 4R,4aS,6R stereoisomer).	7.6	1	0	carbobicyclic compound; enone; sesquiterpenoid	fragrance; insect repellent; plant metabolite
4-thiopyridine 4-thiopyridine: RN given refers to 4-thiopyridine cpd	2.06	1	0
potassium oxonate potassium oxonate: used to induce hyperuricemia in mice	2.11	1	0	organic molecular entity
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	2.21	1	0
dasatinib N-(2-chloro-6-methylphenyl)-2-((6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-yl)amino)-1,3-thiazole-5-carboxamide: a dasatinib prodrug; structure in first source. dasatinib (anhydrous) : An aminopyrimidine that is 2-methylpyrimidine which is substituted at position 4 by the primary amino group of 2-amino-1,3-thiazole-5-carboxylic acid and at position 6 by a 4-(2-hydroxyethyl)piperazin-1-yl group, and in which the carboxylic acid group has been formally condensed with 2-chloro-6-methylaniline to afford the corresponding amide. A multi-targeted kinase inhibitor, it is used, particularly as the monohydrate, for the treatment of chronic, accelerated, or myeloid or lymphoid blast phase chronic myeloid leukemia. Note that the name 'dasatinib' is used to refer to the monohydrate (USAN) as well as to anhydrous dasatinib (INN).	3.16	1	0	1,3-thiazoles; aminopyrimidine; monocarboxylic acid amide; N-(2-hydroxyethyl)piperazine; N-arylpiperazine; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antineoplastic agent; tyrosine kinase inhibitor
calixarenes Calixarenes: Phenolic metacyclophanes derived from condensation of PHENOLS and ALDEHYDES. The name derives from the vase-like molecular structures. A bracketed [n] indicates the number of aromatic rings.. calixarenes : Originally macrocyclic compounds capable of assuming a basket (or "calix") shaped conformation. They are formed from p-hydrocarbyl phenols and formaldehyde. The term now applies to a variety of derivatives by substitution of the hydrocarbon cyclo{oligo[(1,3-phenylene)methylene]}.. calixarene : A macrocycle composed of 1,3-phenylene groups linked by methylene groups. The number of 1,3-phenylene units in the macrocycle is denoted by the "n" in calix[n]arene name.	3.41	7	0
ru 42173 RU 42173: structure given in first source	2.17	1	0	benzazepine
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	7.77	3	0
sodium dodecyl sulfate Sodium Dodecyl Sulfate: An anionic surfactant, usually a mixture of sodium alkyl sulfates, mainly the lauryl; lowers surface tension of aqueous solutions; used as fat emulsifier, wetting agent, detergent in cosmetics, pharmaceuticals and toothpastes; also as research tool in protein biochemistry.. sodium dodecyl sulfate : An organic sodium salt that is the sodium salt of dodecyl hydrogen sulfate.	2.77	3	0	organic sodium salt	detergent; protein denaturant
alpha-chymotrypsin Chymotrypsin: A serine endopeptidase secreted by the pancreas as its zymogen, CHYMOTRYPSINOGEN and carried in the pancreatic juice to the duodenum where it is activated by TRYPSIN. It selectively cleaves aromatic amino acids on the carboxyl side.	2.05	1	0
sodium borohydride sodium borohydride: RN given refers to parent cpd	2.11	1	0	inorganic sodium salt; metal tetrahydridoborate
2-mercaptoacetate 2-mercaptoacetate: RN given refers to parent cpd	2.81	3	0	monocarboxylic acid anion
quercetin [no description available]	2.21	1	0	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	2.47	2	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
vitamin k semiquinone radical vitamin K semiquinone radical: found in active preparations of vitamin K-dependent carboxylase. vitamin K : Any member of a group of fat-soluble 2-methyl-1,4-napthoquinones that exhibit biological activity against vitamin K deficiency. Vitamin K is required for the synthesis of prothrombin and certain other blood coagulation factors.	2.06	1	0
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	2.17	1	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
genistein [no description available]	2.11	1	0	7-hydroxyisoflavones	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; human urinary metabolite; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
ubiquinone 8 [no description available]	2.1	1	0	ubiquinones	biomarker
sirolimus Sirolimus: A macrolide compound obtained from Streptomyces hygroscopicus that acts by selectively blocking the transcriptional activation of cytokines thereby inhibiting cytokine production. It is bioactive only when bound to IMMUNOPHILINS. Sirolimus is a potent immunosuppressant and possesses both antifungal and antineoplastic properties.. sirolimus : A macrolide lactam isolated from Streptomyces hygroscopicus consisting of a 29-membered ring containing 4 trans double bonds, three of which are conjugated. It is an antibiotic, immunosupressive and antineoplastic agent.	2.54	2	0	antibiotic antifungal drug; cyclic acetal; cyclic ketone; ether; macrolide lactam; organic heterotricyclic compound; secondary alcohol	antibacterial drug; anticoronaviral agent; antineoplastic agent; bacterial metabolite; geroprotector; immunosuppressive agent; mTOR inhibitor
morphine Meconium: The thick green-to-black mucilaginous material found in the intestines of a full-term fetus. It consists of secretions of the INTESTINAL GLANDS; BILE PIGMENTS; FATTY ACIDS; AMNIOTIC FLUID; and intrauterine debris. It constitutes the first stools passed by a newborn.	2.08	1	0	morphinane alkaloid; organic heteropentacyclic compound; tertiary amino compound	anaesthetic; drug allergen; environmental contaminant; geroprotector; mu-opioid receptor agonist; opioid analgesic; plant metabolite; vasodilator agent; xenobiotic
7,8-dimethylalloxazine 7,8-dimethylalloxazine: structure. 7,8-dimethylisoalloxazine : A 7,8-dimethylbenzo[g]pteridine-2,4-dione that is isoalloxazine substituted by methyl groups at positions 7 and 8.. lumichrome : A compound showing blue fluorescence, formed by a photolysis of riboflavin in acid or neutral solution.	2.05	1	0	7,8-dimethylbenzo[g]pteridine-2,4-dione	plant metabolite
su 11248 [no description available]	3.61	2	0	monocarboxylic acid amide; pyrroles	angiogenesis inhibitor; antineoplastic agent; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; immunomodulator; neuroprotective agent; vascular endothelial growth factor receptor antagonist
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	3.48	7	0	carbon group element atom; elemental lead; metal atom	neurotoxin
antimony Antimony: A metallic element that has the atomic symbol Sb, atomic number 51, and atomic weight 121.75. It is used as a metal alloy and as medicinal and poisonous salts. It is toxic and an irritant to the skin and the mucous membranes.	2.41	2	0	metalloid atom; pnictogen
rubidium Rubidium: An element that is an alkali metal. It has an atomic symbol Rb, atomic number 37, and atomic weight 85.47. It is used as a chemical reagent and in the manufacture of photoelectric cells.	2.08	1	0	alkali metal atom
bismuth Bismuth: A metallic element that has the atomic symbol Bi, and atomic number 83. Its principal isotope is Bismuth 209.	2.07	1	0	metal atom; pnictogen
arsenic Arsenic: A shiny gray element with atomic symbol As, atomic number 33, and atomic weight 75. It occurs throughout the universe, mostly in the form of metallic arsenides. Most forms are toxic. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), arsenic and certain arsenic compounds have been listed as known carcinogens. (From Merck Index, 11th ed)	3.31	1	0	metalloid atom; pnictogen	micronutrient
sulfur Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.	2.41	1	0	chalcogen; nonmetal atom	macronutrient
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	7.11	1	0	cysteinium	fundamental metabolite
silicon Silicon: A trace element that constitutes about 27.6% of the earth's crust in the form of SILICON DIOXIDE. It does not occur free in nature. Silicon has the atomic symbol Si, atomic number 14, and atomic weight [28.084; 28.086].	3.89	3	0	carbon group element atom; metalloid atom; nonmetal atom
phosphorus Phosphorus: A non-metal element that has the atomic symbol P, atomic number 15, and atomic weight 31. It is an essential element that takes part in a broad variety of biochemical reactions.	3.78	3	0	monoatomic phosphorus; nonmetal atom; pnictogen	macronutrient
boron Boron: A trace element with the atomic symbol B, atomic number 5, and atomic weight [10.806; 10.821]. Boron-10, an isotope of boron, is used as a neutron absorber in BORON NEUTRON CAPTURE THERAPY.	3.66	2	0	boron group element atom; metalloid atom; nonmetal atom	micronutrient
abscisic acid Abscisic Acid: Abscission-accelerating plant growth substance isolated from young cotton fruit, leaves of sycamore, birch, and other plants, and from potatoes, lemons, avocados, and other fruits.. (S)-2-trans-abscisic acid : A 2-trans-abscisic acid with (S)-configuration at the chiral centre.. (+)-abscisic acid : The naturally occurring (1'S)-(+) enantiomer of abscisic acid. It is an important sesquiterpenoid plant hormone which acts as a regulator of plant responses to environmental stresses such as drought and cold.	2.17	1	0	2-trans-abscisic acid
ammonium sulfate Ammonium Sulfate: Sulfuric acid diammonium salt. It is used in CHEMICAL FRACTIONATION of proteins.. ammonium sulfate : An inorganic sulfate salt obtained by reaction of sulfuric acid with two equivalents of ammonia. A high-melting (decomposes above 280degreeC) white solid which is very soluble in water (70.6 g/100 g water at 0degreeC; 103.8 g/100 g water at 100degreeC), it is widely used as a fertilizer for alkaline soils.	2.52	2	0	ammonium salt; inorganic sulfate salt	fertilizer
selenium Selenium: An element with the atomic symbol Se, atomic number 34, and atomic weight 78.97. It is an essential micronutrient for mammals and other animals but is toxic in large amounts. Selenium protects intracellular structures against oxidative damage. It is an essential component of GLUTATHIONE PEROXIDASE.	2.89	3	0	chalcogen; nonmetal atom	micronutrient
tellurium Tellurium: An element that is a member of the chalcogen family. It has the atomic symbol Te, atomic number 52, and atomic weight 127.60. It has been used as a coloring agent and in the manufacture of electrical equipment. Exposure may cause nausea, vomiting, and CNS depression.	3.18	5	0	chalcogen; metalloid atom
oxalates Oxalates: Derivatives of OXALIC ACID. Included under this heading are a broad variety of acid forms, salts, esters, and amides that are derived from the ethanedioic acid structure.	3.89	3	0
pyroantimonate pyroantimonate: RN from 9th CI, Chem Subs Index & given refers to ion; see also potassium antimonate: 16210-51-8, sodium antimonate: 20602-01-1	1.98	1	0
dizocilpine maleate Dizocilpine Maleate: A potent noncompetitive antagonist of the NMDA receptor (RECEPTORS, N-METHYL-D-ASPARTATE) used mainly as a research tool. The drug has been considered for the wide variety of neurodegenerative conditions or disorders in which NMDA receptors may play an important role. Its use has been primarily limited to animal and tissue experiments because of its psychotropic effects.. dizocilpine maleate : A maleate salt obtained by reaction of dizocilpine with one equivalent of maleic acid.	2.13	1	0	maleate salt; tetracyclic antidepressant	anaesthetic; anticonvulsant; neuroprotective agent; nicotinic antagonist; NMDA receptor antagonist
1-palmitoyl-2-oleoylphosphatidylcholine 1-palmitoyl-2-oleoylphosphatidylcholine: RN given refers to (Z)-isomer	2.04	1	0
nitrofurantoin Nitrofurantoin: A urinary anti-infective agent effective against most gram-positive and gram-negative organisms. Although sulfonamides and antibiotics are usually the agents of choice for urinary tract infections, nitrofurantoin is widely used for prophylaxis and long-term suppression.. nitrofurantoin : An imidazolidine-2,4-dione that is hydantoin substituted at position 1 by a [(5-nitro-2-furyl)methylene]amino group. An antibiotic that damages bacterial DNA.	7.21	1	0	imidazolidine-2,4-dione; nitrofuran antibiotic; organonitrogen heterocyclic antibiotic; organooxygen heterocyclic antibiotic	antibacterial drug; antiinfective agent; hepatotoxic agent
mannich bases Mannich Bases: Ketonic amines prepared from the condensation of a ketone with formaldehyde and ammonia or a primary or secondary amine. A Mannich base can act as the equivalent of an alpha,beta unsaturated ketone in synthesis or can be reduced to form physiologically active amino alcohols.	2.47	2	0
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).	3.19	5	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
zeolites [no description available]	2.6	1	0
oxadiazoles Oxadiazoles: Compounds containing five-membered heteroaromatic rings containing two carbons, two nitrogens, and one oxygen atom which exist in various regioisomeric forms.	2.05	1	0
empagliflozin [no description available]	2.6	1	0	aromatic ether; C-glycosyl compound; monochlorobenzenes; tetrahydrofuryl ether	hypoglycemic agent; sodium-glucose transport protein subtype 2 inhibitor
ammonium citrate [no description available]	2.07	1	0	ammonium salt; citrate salt	buffer; food emulsifier
perylenetetracarboxylic diimide perylenetetracarboxylic diimide: structure in first source	2.98	4	0
aflatoxin m1 Aflatoxin M1: A 4-hydroxylated metabolite of AFLATOXIN B1, one of the MYCOTOXINS from ASPERGILLUS tainted food. It is associated with LIVER damage and cancer resulting from its P450 activation to the epoxide which alkylates DNA. Toxicity depends on the balance of liver enzymes that activate it (CYTOCHROME P-450) and others that detoxify it (GLUTATHIONE S TRANSFERASE) (Pharmac Ther 50.443 1991). Primates & rat are sensitive while mouse and hamster are tolerant (Canc Res 29.236 1969).. aflatoxin M1 : A member of the class of aflatoxins that is aflatoxin B1 in which the hydrogen at position 9a is replaced by a hydroxy group.	7.13	1	0	aflatoxin; aromatic ether; aromatic ketone; tertiary alcohol	Aspergillus metabolite; human xenobiotic metabolite; mammalian metabolite
tannins Tannins: Polyphenolic compounds with molecular weights of around 500-3000 daltons and containing enough hydroxyl groups (1-2 per 100 MW) for effective cross linking of other compounds (ASTRINGENTS). The two main types are HYDROLYZABLE TANNINS and CONDENSED TANNINS. Historically, the term has applied to many compounds and plant extracts able to render skin COLLAGEN impervious to degradation. The word tannin derives from the Celtic word for OAK TREE which was used for leather processing.	3.99	3	0
oligonucleotides [no description available]	7.81	3	0
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	3.33	5	0	glycoside
perovskite calcium titanate : A calcium salt with the formula CaTiO3, generally obtained in the form of the mineral perovskite.	7.25	1	0
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	2.04	1	0	1,2-diacyl-sn-glycero-3-phosphocholine
chlorophyll a Chlorophyll: Porphyrin derivatives containing magnesium that act to convert light energy in photosynthetic organisms.. chlorophyll : A family of magnesium porphyrins, defined by the presence of a fifth ring beyond the four pyrrole-like rings. The rings can have various side chains which usually include a long phytol chain.	2	1	0	chlorophyll; methyl ester	cofactor
ubiquinone Ubiquinone: A lipid-soluble benzoquinone which is involved in ELECTRON TRANSPORT in mitochondrial preparations. The compound occurs in the majority of aerobic organisms, from bacteria to higher plants and animals.	2.1	1	0
chitosan [no description available]	3.86	10	0
potassium borohydride [no description available]	2.1	1	0
merocyanine dye merocyanine dye: fluorescent dye used for studying axons 2 position on pyrimidine ring may be S or O; RN given refers to Na salt; structure	7.01	1	0
canagliflozin canagliflozin hydrate : A hydrate that is the hemihydrate form of canagliflozin. Used for treatment of type II diabetes via inhibition of sodium-glucose transport protein subtype 2.	2.6	1	0	C-glycosyl compound; organofluorine compound; thiophenes	hypoglycemic agent; sodium-glucose transport protein subtype 2 inhibitor
piperidines Piperidines: A family of hexahydropyridines.	2.13	1	0
interleukin-8 Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.	2.48	2	0
lanthanide nitrate [no description available]	2.11	1	0
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	2.78	3	0	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
tetracycline Tetracycline: A naphthacene antibiotic that inhibits AMINO ACYL TRNA binding during protein synthesis.. tetracycline : A broad-spectrum polyketide antibiotic produced by the Streptomyces genus of actinobacteria.	7.9	2	0
oxytetracycline, anhydrous Oxytetracycline: A TETRACYCLINE analog isolated from the actinomycete STREPTOMYCES RIMOSUS and used in a wide variety of clinical conditions.. oxytetracycline : A tetracycline used for treatment of infections caused by a variety of Gram positive and Gram negative microorganisms including Mycoplasma pneumoniae, Pasteurella pestis, Escherichia coli, Haemophilus influenzae (respiratory infections), and Diplococcus pneumoniae.	2.25	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.	2.21	1	0	benzenes; hydroxycoumarin; methyl ketone
clay Clay: A naturally-occurring rock or soil constituent characterized by particles with a diameter of less than 0.005 mm. It is composed primarily of hydrous aluminum silicates, trace amounts of metal OXIDES, and organic matter.	7.03	1	0
sybr green i SYBR Green I: binds to double stranded DNA of less than 20 pg following agarose or polyacrylamide gel electrophoresis; excited at 497 nm and emits at 520 nm. SYBR Green I : A benzothiazolium ion resulting from the methylation of the nitrogen of the benzothiazole group of N-[4-(1,3-benzothiazol-2-ylmethylene)-1-phenyl-1,4-dihydroquinolin-2-yl]-N',N'-dimethyl-N-propylpropane-1,3-diamine. A cationic unsymmetrical cyanine dye that binds to double-stranded DNA and is used as a nucleic acid stain in molecular biology.	2.61	2	0	benzothiazolium ion; cyanine dye; quinolines; tertiary amine	fluorescent dye
araldite araldite: induces experimental asthma in immunized guinea pigs; RN given refers to araldite; see also record for araldite B	6.98	1	0
caseins Caseins: A mixture of related phosphoproteins occurring in milk and cheese. The group is characterized as one of the most nutritive milk proteins, containing all of the common amino acids and rich in the essential ones.	2.21	1	0
phthalocyanine phthalocyanine : A tetrapyrrole fundamental parent that consists of four isoindole-type units, with the connecting carbon atoms in the macrocycle replaced by nitrogen.	2.13	1	0	phthalocyanines; tetrapyrrole fundamental parent
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	2.92	4	0
vitamin b 12 Vitamin B 12: A cobalt-containing coordination compound produced by intestinal micro-organisms and found also in soil and water. Higher plants do not concentrate vitamin B 12 from the soil and so are a poor source of the substance as compared with animal tissues. INTRINSIC FACTOR is important for the assimilation of vitamin B 12.	2.05	1	0
flavin mononucleotide Flavin Mononucleotide: A coenzyme for a number of oxidative enzymes including NADH DEHYDROGENASE. It is the principal form in which RIBOFLAVIN is found in cells and tissues.	2.17	1	0
orabase Orabase: used in therapy of oral mucosal ulcers	2.59	2	0
muramidase Muramidase: A basic enzyme that is present in saliva, tears, egg white, and many animal fluids. It functions as an antibacterial agent. The enzyme catalyzes the hydrolysis of 1,4-beta-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrin. EC 3.2.1.17.	2.53	2	0
polident Polident: contains sodium perborate & potassium monopersulfate	2.08	1	0
chondroitin sulfates Chondroitin Sulfates: Derivatives of chondroitin which have a sulfate moiety esterified to the galactosamine moiety of chondroitin. Chondroitin sulfate A, or chondroitin 4-sulfate, and chondroitin sulfate C, or chondroitin 6-sulfate, have the sulfate esterified in the 4- and 6-positions, respectively. Chondroitin sulfate B (beta heparin; DERMATAN SULFATE) is a misnomer and this compound is not a true chondroitin sulfate.	2.47	2	0
deoxyguanosine [no description available]	2.05	1	0	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanine [no description available]	3.16	1	0	2-aminopurines; oxopurine; purine nucleobase	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
hypoxanthine [no description available]	2.06	1	0	nucleobase analogue; oxopurine; purine nucleobase	fundamental metabolite
3-methyladenine N3-methyladenine: structure in first source	2.52	2	0
allopurinol Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.	7.31	1	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
ammeline ammeline: causes retinal degeneration	4.37	19	0	diamino-1,3,5-triazine; monohydroxy-1,3,5-triazine
pemetrexed pemetrexed disodium : An organic sodium salt that is the disodium salt of N-{4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acid. Inhibits thymidylate synthase (TS), 421 dihydrofolate reductase (DHFR), and glycinamide ribonucleotide formyltransferase (GARFT).	3.16	1	0	N-acyl-L-glutamic acid; pyrrolopyrimidine	antimetabolite; antineoplastic agent; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; EC 2.1.1.45 (thymidylate synthase) inhibitor; EC 2.1.2.2 (phosphoribosylglycinamide formyltransferase) inhibitor
8-hydroxy-2'-deoxyguanosine 8-Hydroxy-2'-Deoxyguanosine: Common oxidized form of deoxyguanosine in which C-8 position of guanine base has a carbonyl group.. 8-hydroxy-2'-deoxyguanosine : Guanosine substituted at the purine 8-position by a hydroxy group. It is used as a biomarker of oxidative DNA damage.	2.05	1	0	guanosines	biomarker
2-naphthol orange 2-naphthol orange: structure; see also record for C.I. Solvent Orange 2	2.15	1	0
acetylcellulose acetylcellulose: coating compound. cellulose acetate : A glucan derivative obtained through the esterification of cellulose by acetic anhydride or acetic acid, resulting in the substitution of some of the hydroxy groups of cellulose by acetyl groups. It is used in a variety of applications including base material for photographic film, clothing, membrane filters, coatings, food packaging, and as a frame material for eyeglasses.	2.15	1	0
metallothionein Metallothionein: A low-molecular-weight (approx. 10 kD) protein occurring in the cytoplasm of kidney cortex and liver. It is rich in cysteinyl residues and contains no aromatic amino acids. Metallothionein shows high affinity for bivalent heavy metals.	7.11	1	0
pyrimidinones Pyrimidinones: Heterocyclic compounds known as 2-pyrimidones (or 2-hydroxypyrimidines) and 4-pyrimidones (or 4-hydroxypyrimidines) with the general formula C4H4N2O.	3.54	2	0
phenanthrenes Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.	2.41	1	0

Condition	Relationship Strength	Studies	Trials
Acute Liver Injury, Drug-Induced [description not available]	3.49	7	0
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	3.49	7	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	5.7	28	0
Kidney Failure A severe irreversible decline in the ability of kidneys to remove wastes, concentrate URINE, and maintain ELECTROLYTE BALANCE; BLOOD PRESSURE; and CALCIUM metabolism.	4.59	24	0
Cyst [description not available]	2.41	1	0
Renal Insufficiency Conditions in which the KIDNEYS perform below the normal level in the ability to remove wastes, concentrate URINE, and maintain ELECTROLYTE BALANCE; BLOOD PRESSURE; and CALCIUM metabolism. Renal insufficiency can be classified by the degree of kidney damage (as measured by the level of PROTEINURIA) and reduction in GLOMERULAR FILTRATION RATE.	4.59	24	0
Albuminuria The presence of albumin in the urine, an indicator of KIDNEY DISEASES.	2.41	1	0
Kidney Stones [description not available]	8.4	50	1
Kidney Calculi Stones in the KIDNEY, usually formed in the urine-collecting area of the kidney (KIDNEY PELVIS). Their sizes vary and most contains CALCIUM OXALATE.	13.4	50	1
Delayed Effects, Prenatal Exposure [description not available]	3.62	8	0
Bladder Calculi [description not available]	5.2	11	0
Birth Weight The mass or quantity of heaviness of an individual at BIRTH. It is expressed by units of pounds or kilograms.	2.25	1	0
Disease Resistance The capacity of an organism to defend itself against pathological processes or the agents of those processes. This most often involves innate immunity whereby the organism responds to pathogens in a generic way. The term disease resistance is used most frequently when referring to plants.	7.25	1	0
Fish Diseases Diseases of freshwater, marine, hatchery or aquarium fish. This term includes diseases of both teleosts (true fish) and elasmobranchs (sharks, rays and skates).	2.54	2	0
Bacterial Infections, Gram-Negative [description not available]	2.25	1	0
Gram-Negative Bacterial Infections Infections caused by bacteria that show up as pink (negative) when treated by the gram-staining method.	2.25	1	0
Bladder Cancer [description not available]	4.76	7	0
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	4.76	7	0
Cancer of Colon [description not available]	2.25	1	0
Colonic Neoplasms Tumors or cancer of the COLON.	2.25	1	0
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)	10.34	52	0
Urinary Lithiasis [description not available]	6.64	34	0
Urolithiasis Formation of stones in any part of the URINARY TRACT, usually in the KIDNEY; URINARY BLADDER; or the URETER.	6.64	34	0
Rhabdomyolysis Necrosis or disintegration of skeletal muscle often followed by myoglobinuria.	7.31	1	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	3.79	10	0
Innate Inflammatory Response [description not available]	3.38	6	0
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	3.38	6	0
Cognition Disorders Disorders characterized by disturbances in mental processes related to learning, thinking, reasoning, and judgment.	3.62	8	0
Encephalopathy, Toxic [description not available]	3.94	2	0
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	8.56	32	1
Polyuria Urination of a large volume of urine with an increase in urinary frequency, commonly seen in diabetes (DIABETES MELLITUS; DIABETES INSIPIDUS).	7.17	1	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	4.64	25	0
Testicular Diseases Pathological processes of the TESTIS.	2.53	2	0
Bone Stress Reaction [description not available]	2.17	1	0
Chronic Kidney Diseases [description not available]	4.56	3	0
Renal Insufficiency, Chronic Conditions in which the KIDNEYS perform below the normal level for more than three months. Chronic kidney insufficiency is classified by five stages according to the decline in GLOMERULAR FILTRATION RATE and the degree of kidney damage (as measured by the level of PROTEINURIA). The most severe form is the end-stage renal disease (CHRONIC KIDNEY FAILURE). (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002)	4.56	3	0
Acute Kidney Failure [description not available]	6.52	24	0
Glomerular Necrosis [description not available]	3.12	1	0
Acute Kidney Injury Abrupt reduction in kidney function. Acute kidney injury encompasses the entire spectrum of the syndrome including acute kidney failure; ACUTE KIDNEY TUBULAR NECROSIS; and other less severe conditions.	6.52	24	0
Extravascular Hemolysis [description not available]	2.99	4	0
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	2.99	4	0
Infections, Klebsiella [description not available]	2.08	1	0
Klebsiella Infections Infections with bacteria of the genus KLEBSIELLA.	2.08	1	0
Urinary Calculi Low-density crystals or stones in any part of the URINARY TRACT. Their chemical compositions often include CALCIUM OXALATE, magnesium ammonium phosphate (struvite), CYSTINE, or URIC ACID.	8.14	39	1
Blood Poisoning [description not available]	2.08	1	0
Food Poisoning [description not available]	5.47	10	0
Nephritis Inflammation of any part of the KIDNEY.	7.78	3	0
Sepsis Systemic inflammatory response syndrome with a proven or suspected infectious etiology. When sepsis is associated with organ dysfunction distant from the site of infection, it is called severe sepsis. When sepsis is accompanied by HYPOTENSION despite adequate fluid infusion, it is called SEPTIC SHOCK.	2.08	1	0
Anoxemia [description not available]	2.08	1	0
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	7.08	1	0
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.	2.4	2	0
Hyperplasia An increase in the number of cells in a tissue or organ without tumor formation. It differs from HYPERTROPHY, which is an increase in bulk without an increase in the number of cells.	2.94	4	0
Malnourishment [description not available]	2.08	1	0
Benign Neoplasms [description not available]	3.19	6	0
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.	8.19	6	0
Malnutrition An imbalanced nutritional status resulting from insufficient intake of nutrients to meet normal physiological requirement.	2.08	1	0
Botulism, Infantile [description not available]	2.1	1	0
Botulism A disease caused by potent protein NEUROTOXINS produced by CLOSTRIDIUM BOTULINUM which interfere with the presynaptic release of ACETYLCHOLINE at the NEUROMUSCULAR JUNCTION. Clinical features include abdominal pain, vomiting, acute PARALYSIS (including respiratory paralysis), blurred vision, and DIPLOPIA. Botulism may be classified into several subtypes (e.g., food-borne, infant, wound, and others). (From Adams et al., Principles of Neurology, 6th ed, p1208)	2.1	1	0
Stunted Growth [description not available]	2.1	1	0
Growth Disorders Deviations from the average values for a specific age and sex in any or all of the following: height, weight, skeletal proportions, osseous development, or maturation of features. Included here are both acceleration and retardation of growth.	2.1	1	0
Diabetic Glomerulosclerosis [description not available]	2.1	1	0
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	1	0
Cancer of Prostate [description not available]	2.1	1	0
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	2.1	1	0
Nephrolithiasis Formation of stones in the KIDNEY.	6.06	19	0
Malignant Melanoma [description not available]	2.11	1	0
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	2.11	1	0
Disease Exacerbation [description not available]	3.04	1	0
Dysuria Painful URINATION. It is often associated with infections of the lower URINARY TRACT.	3.04	1	0
Stillbirth The event that a FETUS is born dead or stillborn.	2.15	1	0
Acrania [description not available]	2.15	1	0
Cardiac Septal Defect [description not available]	2.15	1	0
Neural Tube Defects Congenital malformations of the central nervous system and adjacent structures related to defective neural tube closure during the first trimester of pregnancy generally occurring between days 18-29 of gestation. Ectodermal and mesodermal malformations (mainly involving the skull and vertebrae) may occur as a result of defects of neural tube closure. (From Joynt, Clinical Neurology, 1992, Ch55, pp31-41)	2.15	1	0
Weight Gain Increase in BODY WEIGHT over existing weight.	2.5	2	0
Tooth Discoloration Any change in the hue, color, or translucency of a tooth due to any cause. Restorative filling materials, drugs (both topical and systemic), pulpal necrosis, or hemorrhage may be responsible. (Jablonski, Dictionary of Dentistry, 1992, p253)	2.11	1	0
Hyperuricemia Excessive URIC ACID or urate in blood as defined by its solubility in plasma at 37 degrees C; greater than 0.42mmol per liter (7.0mg/dL) in men or 0.36mmol per liter (6.0mg/dL) in women. This condition is caused by overproduction of uric acid or impaired renal clearance. Hyperuricemia can be acquired, drug-induced or genetically determined (LESCH-NYHAN SYNDROME). It is associated with HYPERTENSION and GOUT.	7.11	1	0
Electrolytes Substances that dissociate into two or more ions, to some extent, in water. Solutions of electrolytes thus conduct an electric current and can be decomposed by it (ELECTROLYSIS). (Grant & Hackh's Chemical Dictionary, 5th ed)	7.96	4	0
Weight Reduction [description not available]	3.04	1	0
Weight Loss Decrease in existing BODY WEIGHT.	3.04	1	0
Drug Overdose Accidental or deliberate use of a medication or street drug in excess of normal dosage.	3.04	1	0
Cancer of the Urinary Tract [description not available]	4.53	5	0
Canine Diseases [description not available]	5.44	14	0
Cat Diseases Diseases of the domestic cat (Felis catus or F. domesticus). This term does not include diseases of the so-called big cats such as CHEETAHS; LIONS; tigers, cougars, panthers, leopards, and other Felidae for which the heading CARNIVORA is used.	5.37	13	0
Ureteral Calculi Stones in the URETER that are formed in the KIDNEY. They are rarely more than 5 mm in diameter for larger renal stones cannot enter ureters. They are often lodged at the ureteral narrowing and can cause excruciating renal colic.	2.04	1	0
Hematuria Presence of blood in the urine.	2.45	2	0
Poisoning Used with drugs, chemicals, and industrial materials for human or animal poisoning, acute or chronic, whether the poisoning is accidental, occupational, suicidal, by medication error, or by environmental exposure.	4.07	5	0
Trypanosomiasis Infection with protozoa of the genus TRYPANOSOMA.	2.05	1	0
Swine Diseases Diseases of domestic swine and of the wild boar of the genus Sus.	2.45	2	0
Chronic Kidney Failure [description not available]	2.46	2	0
Cancer of Kidney [description not available]	2.05	1	0
Vesicoureteral Reflux [description not available]	2.05	1	0
Kidney Failure, Chronic The end-stage of CHRONIC RENAL INSUFFICIENCY. It is characterized by the severe irreversible kidney damage (as measured by the level of PROTEINURIA) and the reduction in GLOMERULAR FILTRATION RATE to less than 15 ml per min (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002). These patients generally require HEMODIALYSIS or KIDNEY TRANSPLANTATION.	2.46	2	0
Kidney Neoplasms Tumors or cancers of the KIDNEY.	2.05	1	0
Vesico-Ureteral Reflux Retrograde flow of urine from the URINARY BLADDER into the URETER. This is often due to incompetence of the vesicoureteral valve leading to ascending bacterial infection into the KIDNEY.	2.05	1	0
Adverse Drug Event [description not available]	2.05	1	0
Drug-Related Side Effects and Adverse Reactions Disorders that result from the intended use of PHARMACEUTICAL PREPARATIONS. Included in this heading are a broad variety of chemically-induced adverse conditions due to toxicity, DRUG INTERACTIONS, and metabolic effects of pharmaceuticals.	2.05	1	0
Proteinuria The presence of proteins in the urine, an indicator of KIDNEY DISEASES.	7.75	3	0
Orphan Diseases Rare diseases that have not been well studied.	2.05	1	0
Hydronephrosis Abnormal enlargement or swelling of a KIDNEY due to dilation of the KIDNEY CALICES and the KIDNEY PELVIS. It is often associated with obstruction of the URETER or chronic kidney diseases that prevents normal drainage of urine into the URINARY BLADDER.	2.46	2	0
Animal Diseases Diseases that occur in VERTEBRATE animals.	2.05	1	0
Chronic Illness [description not available]	2.05	1	0
Abnormalities, Urogenital [description not available]	2.05	1	0
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	2.05	1	0
Anuria Absence of urine formation. It is usually associated with complete bilateral ureteral (URETER) obstruction, complete lower urinary tract obstruction, or unilateral ureteral obstruction when a solitary kidney is present.	2.05	1	0
Hyperpotassemia [description not available]	2.05	1	0
Blood Pressure, High [description not available]	2.05	1	0
Oliguria Decreased URINE output that is below the normal range. Oliguria can be defined as urine output of less than or equal to 0.5 or 1 ml/kg/hr depending on the age.	2.05	1	0
Hyperkalemia Abnormally high potassium concentration in the blood, most often due to defective renal excretion. It is characterized clinically by electrocardiographic abnormalities (elevated T waves and depressed P waves, and eventually by atrial asystole). In severe cases, weakness and flaccid paralysis may occur. (Dorland, 27th ed)	2.05	1	0
Hypertension Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.	2.05	1	0
African Sleeping Sickness [description not available]	2.44	2	0
Trypanosomiasis, African A disease endemic among people and animals in Central Africa. It is caused by various species of trypanosomes, particularly T. gambiense and T. rhodesiense. Its second host is the TSETSE FLY. Involvement of the central nervous system produces African sleeping sickness. Nagana is a rapidly fatal trypanosomiasis of horses and other animals.	2.44	2	0
Acute Disease Disease having a short and relatively severe course.	2.05	1	0
Preterm Birth [description not available]	2.05	1	0
Premature Birth CHILDBIRTH before 37 weeks of PREGNANCY (259 days from the first day of the mother's last menstrual period, or 245 days after FERTILIZATION).	2.05	1	0
Poultry Diseases Diseases of birds which are raised as a source of meat or eggs for human consumption and are usually found in barnyards, hatcheries, etc. The concept is differentiated from BIRD DISEASES which is for diseases of birds not considered poultry and usually found in zoos, parks, and the wild.	4.42	2	2
Disease, Pulmonary [description not available]	2.06	1	0
Lung Diseases Pathological processes involving any part of the LUNG.	2.06	1	0
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.	2.06	1	0
Abnormalities, Autosome [description not available]	2.06	1	0
Chromosome-Defective Micronuclei [description not available]	2.06	1	0
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	3.86	2	1
Body Weight, Fetal [description not available]	2.06	1	0
Jet Lag [description not available]	2.98	1	0
Icterus [description not available]	2.07	1	0
Liver Dysfunction [description not available]	2.07	1	0
Jaundice A clinical manifestation of HYPERBILIRUBINEMIA, characterized by the yellowish staining of the SKIN; MUCOUS MEMBRANE; and SCLERA. Clinical jaundice usually is a sign of LIVER dysfunction.	2.07	1	0
Liver Diseases Pathological processes of the LIVER.	2.07	1	0
Cirrhosis [description not available]	2.07	1	0
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	2.07	1	0
Carcinoma, Bronchial [description not available]	1.93	1	0
Cancer of Lung [description not available]	1.93	1	0
Carcinoma, Bronchogenic Malignant neoplasm arising from the epithelium of the BRONCHI. It represents a large group of epithelial lung malignancies which can be divided into two clinical groups: SMALL CELL LUNG CANCER and NON-SMALL-CELL LUNG CARCINOMA.	1.93	1	0
Lung Neoplasms Tumors or cancer of the LUNG.	1.93	1	0
Reproductive Sterility [description not available]	1.93	1	0
Infertility A reduced or absent capacity to reproduce.	1.93	1	0
Granuloma, Hodgkin [description not available]	2.62	3	0
Leucocythaemia [description not available]	2.63	3	0
Germinoblastoma [description not available]	1.93	1	0
Hodgkin Disease A malignant disease characterized by progressive enlargement of the lymph nodes, spleen, and general lymphoid tissue. In the classical variant, giant usually multinucleate Hodgkin's and REED-STERNBERG CELLS are present; in the nodular lymphocyte predominant variant, lymphocytic and histiocytic cells are seen.	2.62	3	0
Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)	7.63	3	0
Lymphoma A general term for various neoplastic diseases of the lymphoid tissue.	1.93	1	0
Allergic Contact Dermatitis [description not available]	2.41	2	0
Dermatitis, Occupational A recurrent contact dermatitis caused by substances found in the work place.	2.69	3	0
Dermatitis, Allergic Contact A contact dermatitis due to allergic sensitization to various substances. These substances subsequently produce inflammatory reactions in the skin of those who have acquired hypersensitivity to them as a result of prior exposure.	2.41	2	0
Blast Injuries Injuries resulting when a person is struck by particles impelled with violent force from an explosion. Blast causes pulmonary concussion and hemorrhage, laceration of other thoracic and abdominal viscera, ruptured ear drums, and minor effects in the central nervous system. (From Dorland, 27th ed)	2.02	1	0
Caliciviridae Infections Virus diseases caused by CALICIVIRIDAE. They include HEPATITIS E; VESICULAR EXANTHEMA OF SWINE; acute respiratory infections in felines, rabbit hemorrhagic disease, and some cases of gastroenteritis in humans.	2.02	1	0
Gastroenteritis INFLAMMATION of any segment of the GASTROINTESTINAL TRACT from ESOPHAGUS to RECTUM. Causes of gastroenteritis are many including genetic, infection, HYPERSENSITIVITY, drug effects, and CANCER.	2.02	1	0
Condition, Preneoplastic [description not available]	2.42	2	0
Precancerous Conditions Pathological conditions that tend eventually to become malignant.	2.42	2	0
Carcinoma, Transitional Cell A malignant neoplasm derived from TRANSITIONAL EPITHELIAL CELLS, occurring chiefly in the URINARY BLADDER; URETERS; or RENAL PELVIS.	2.67	3	0
Contact Dermatitis [description not available]	7.37	2	0
Dermatitis, Contact A type of acute or chronic skin reaction in which sensitivity is manifested by reactivity to materials or substances coming in contact with the skin. It may involve allergic or non-allergic mechanisms.	2.37	2	0
Acute Lymphoid Leukemia [description not available]	1.98	1	0
B-Cell Chronic Lymphocytic Leukemia [description not available]	1.98	1	0
Acute Myelogenous Leukemia [description not available]	2.38	2	0
Leukemia, Lymphocytic, Chronic, B-Cell A chronic leukemia characterized by abnormal B-lymphocytes and often generalized lymphadenopathy. In patients presenting predominately with blood and bone marrow involvement it is called chronic lymphocytic leukemia (CLL); in those predominately with enlarged lymph nodes it is called small lymphocytic lymphoma. These terms represent spectrums of the same disease.	1.98	1	0
Leukemia, Myeloid, Acute Clonal expansion of myeloid blasts in bone marrow, blood, and other tissue. Myeloid leukemias develop from changes in cells that normally produce NEUTROPHILS; BASOPHILS; EOSINOPHILS; and MONOCYTES.	2.38	2	0
Precursor Cell Lymphoblastic Leukemia-Lymphoma A neoplasm characterized by abnormalities of the lymphoid cell precursors leading to excessive lymphoblasts in the marrow and other organs. It is the most common cancer in children and accounts for the vast majority of all childhood leukemias.	1.98	1	0
Muscle Contraction A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.	1.99	1	0
Idiopathic Parkinson Disease [description not available]	2	1	0
Parkinson Disease A progressive, degenerative neurologic disease characterized by a TREMOR that is maximal at rest, retropulsion (i.e. a tendency to fall backwards), rigidity, stooped posture, slowness of voluntary movements, and a masklike facial expression. Pathologic features include loss of melanin containing neurons in the substantia nigra and other pigmented nuclei of the brainstem. LEWY BODIES are present in the substantia nigra and locus coeruleus but may also be found in a related condition (LEWY BODY DISEASE, DIFFUSE) characterized by dementia in combination with varying degrees of parkinsonism. (Adams et al., Principles of Neurology, 6th ed, p1059, pp1067-75)	2	1	0
Carcinoma, Intraepithelial [description not available]	2	1	0
Carcinoma in Situ A lesion with cytological characteristics associated with invasive carcinoma but the tumor cells are confined to the epithelium of origin, without invasion of the basement membrane.	2	1	0
Papilloma, Squamous Cell [description not available]	2.38	2	0
Papilloma A circumscribed benign epithelial tumor projecting from the surrounding surface; more precisely, a benign epithelial neoplasm consisting of villous or arborescent outgrowths of fibrovascular stroma covered by neoplastic cells. (Stedman, 25th ed)	2.38	2	0
Blast Phase [description not available]	1.97	1	0
Blast Crisis An advanced phase of chronic myelogenous leukemia, characterized by a rapid increase in the proportion of immature white blood cells (blasts) in the blood and bone marrow to greater than 30%.	1.97	1	0

melamine

Description

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Synonyms (131)

Research Excerpts

Overview

Effects

Actions

Treatment

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

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Roles (1)

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Studies (1,320)

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Research Demand Index: 64.52

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melamine

Description

Cross-References

Synonyms (131)

Research Excerpts

Overview

Effects

Actions

Treatment

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Roles (1)

Drug Classes (1)

Pathways (1)

Protein Targets (1)

Potency Measurements

Research

Studies (1,320)

Market Indicators

Research Demand Index: 64.52

Study Types

Related Drugs (460)

Related Conditions (167)