ethylene profile

Plastipore: high density polyethylene sponge biocompatible material; used as posts in dental bridges [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	6325
CHEMBL ID	117822
CHEBI ID	18153
MeSH ID	M0110502

Synonym
r-1150
CHEBI:18153 ,
ch2=ch2
h2c=ch2
aethen
aethylen
c2h4
plastipore
un1038
athylen [german]
un1962
ethylene, pure
einecs 200-815-3
ethylene, compressed [un1962] [flammable gas]
caswell no. 436
un 1038
etileno
elayl
athylen
liquid ethylene
un 1962
epa pesticide chemical code 041901
ethylene (8ci)
olefiant gas
hsdb 168
ethene (9ci)
cmc_13849
acetene
bicarburretted hydrogen
ethene
C06547
ethylene
74-85-1
ethylene, 99.99%
ethylene, >=99.5%
9002-88-4
ldpe
ETHYLENE-CMPD ,
CHEMBL117822
C19503
ethylene, refrigerated liquid (cryogenic liquid) [un1038] [flammable gas]
unii-91gw059kn7
ethylene, compressed [un1962] [flammable gas]
ec 200-815-3
ethylene, refrigerated liquid (cryogenic liquid)
ethylene, compressed
ethylene [nf]
91gw059kn7 ,
FT-0626287
ethylene [iarc]
ethylene [mi]
carboneum hydrogenisatum [hpus]
ethylene [hsdb]
carboneum hydrogenisatum
ethylene [ii]
AKOS015915514
eteno
liquid ethyene
DTXSID1026378 ,
ethylene, messer(r) cangas, 99.98%
mfcd00084423
ethylene, puriss., >=99.95% (gc)
ethylene, purum, >=99.9%
ethylene, >=99.9%
ethene, 9ci
Q151313
Q27286698
ethylene (trans-1,2-d2)
heavy carburetted hydrogen
dtxcid605931
ethylene (ii)
usepa/opp pesticide code: 041901
ethene (ethylene)
ethylene-d3 (gas)
ethylene (iarc)
polyethylene, low density, 500 micron

Excerpt	Reference	Relevance
"Ethylene serves as an important cellular signal to mediate root system architecture adaptation, N uptake and translocation, ammonium toxicity, anthocyanin accumulation, and premature senescence, thereby adapting plant growth and development to external N status."	( Interplay between ethylene and nitrogen nutrition: How ethylene orchestrates nitrogen responses in plants. Chu, C; Hu, B; Ma, B; Ma, T; Xian, W, 2023)	1.97
"Ethylene is a key phytohormone that regulates the ripening of climacteric fruits, and methionine is an indirect precursor of ethylene. "	( A Hydrogen-Sulfide-Repressed Methionine Synthase Geng, ZK; Hu, KD; Li, WJ; Ma, L; Rong, YL; Yao, GF; Zhang, H, 2022)	2.16
"Ethylene is a gaseous phytohormone with an important role in plant development and multiple stress responses."	( The role of ethylene in plant temperature stress response. Bürger, M; Chory, J; Huang, J; Wang, X; Zhao, X, 2023)	2.01
"Ethylene is a plant hormone that causes flower senescence. "	( 1-MCP prevents ultrastructural changes in the organelles of Dendrobium petals that are induced by exogenous ethylene. Ketsa, S; Kirasak, K; Kunyamee, S, 2023)	2.57
"Ethylene is an ideal CO"	( Al-Doped Octahedral Cu Gao, X; Li, S; Peng, J; Sha, X, 2023)	2.35
"Ethylene is a key element of plant physiology, thus ethylene research is important for both, fundamental research and agriculture. "	( Different regulatory modules of two mango ERS1 promoters modulate specific gene expression in response to phytohormones in transgenic model plants. Hagemann, MH; Winterhagen, P; Wünsche, JN, 2019)	1.96
"Ethylene is a major factor affecting the post-harvest storage quality of pomegranates, and functions mainly through the ethylene signal transduction pathway."	( Molecular cloning and characterization of genes related to the ethylene signal transduction pathway in pomegranate ( Guan, XW; Huang, R; Li, W; Xie, B; Zhang, SM, 2019)	1.47
"Ethylene is a gaseous phytohormone that is perceived by two-component histidine kinase-type receptors. "	( Choline transporter-like 1 (CTL1) positively regulates apical hook development in etiolated Arabidopsis seedlings. Cai, G; Lan, W; Luan, S; Wang, Y; Yan, W, 2020)	2
"Ethylene is an important plant hormone that controls growth, development, aging and stress responses. "	( Protein Phosphatases Type 2C Group A Interact with and Regulate the Stability of ACC Synthase 7 in Arabidopsis. Cieśla, A; Janicki, M; Kasprowicz-Maluśki, A; Kubiak, P; Ludwików, A; Marczak, M, 2020)	2
"Ethylene is a gaseous phytohormone and the first of this hormone class to be discovered. "	( Ethylene signaling in plants. Binder, BM, 2020)	3.44
"Ethylene is a key plant hormone controlling the ripening of climacteric fruits, and several transcription factors acting as important regulators of fruit ripening have been identified in tomato (Solanum lycopersicum), a model for climacteric fruits. "	( Tomato transcriptional repressor MYB70 directly regulates ethylene-dependent fruit ripening. Cao, H; Chen, J; Cheng, Y; Gao, Y; Jian, W; Li, Z; Liu, Y; Song, B; Xu, C; Yue, M, 2020)	2.25
"Ethylene is a gaseous hormone which plays important roles in both plant growth and development and stress responses. "	( Ethylene signaling in rice and Arabidopsis: New regulators and mechanisms. Chen, SY; Ma, B; Yin, CC; Zhang, JS; Zhao, H, 2021)	3.51
"Ethylene is an important plant hormone that regulates plant growth, in which the master transcriptionactivator EIN3 (Ethylene Insensitive 3)-mediated transcriptional activation plays vital roles. "	( TREE1-EIN3-mediated transcriptional repression inhibits shoot growth in response to ethylene. Ko, EE; Qiao, H; Tran, J; Wang, L, 2020)	2.23
"Ethylene is a gas molecule that causes detrimental changes in produce."	( Ethylene-removing packaging: Basis for development and latest advances. Almenar, E; Awalgaonkar, G; Beaudry, R, 2020)	2.72
"Ethylene is a gaseous phytohormone involved in various physiological processes, including fruit ripening, senescence, root hair development and stress responses. "	( Distinct Functions of Ethylene and ACC in the Basal Land Plant Marchantia polymorpha. Kanda, A; Katayose, A; Kubo, Y; Motose, H; Takahashi, T, 2021)	2.38
"Ethylene is an important phytohormone with pleotropic roles in plant growth, development, and stress responses. "	( EIN2-directed histone acetylation requires EIN3-mediated positive feedback regulation in response to ethylene. Hernandez, FV; Huang, A; Qiao, H; Shao, Z; Tran, J; Wang, L; Zhang, F; Zhang, Z; Zhao, B, 2021)	2.28
"Ethylene is an important factor affecting the quality of cut roses during transportation and storage."	( Rose (Rosa hybrida) Ethylene Responsive Factor 3 Promotes Rose Flower Senescence via Direct Activation of the Abscisic Acid Synthesis-Related 9-CIS-EPOXYCAROTENOID DIOXYGENASE Gene. Cao, S; Chan, ZL; Chen, S; Li, R; Luo, J; Wang, C; Zhang, T, 2021)	1.67
"Ethylene (ET) is an important gaseous plant hormone. "	( An Activity-Based Sensing Fluorogenic Probe for Monitoring Ethylene in Living Cells and Plants. Chen, Y; Guo, D; Jing, M; Li, J; Li, Y; Liu, H; Wang, B; Wei, L; Yan, W; Ye, Y; Yu, N; Zhao, J; Zheng, Y, 2021)	2.31
"Ethylene is an important regulatory phytohormone for sex differentiation and flower development. "	( Systematic genome-wide analysis of the ethylene-responsive ACS gene family: Contributions to sex form differentiation and development in melon and watermelon. Cheng, D; Wang, Z; Wei, C; Yadav, V; Yan, X; Zhang, X, 2021)	2.33
"Ethylene is a gaseous plant hormone involved in defense, adaptations to environmental stress and fruit ripening. "	( Non-invasive quantification of ethylene in attached fruit headspace at 1 p.p.b. by gas chromatography-mass spectrometry. Garcia-Mas, J; Pereira, L; Phillips, MA; Pujol, M, 2017)	2.18
"Ethylene is an important phytohormone that promotes the ripening of fruits and senescence of flowers thereby reducing their shelf lives. "	( Pyrazinamide and derivatives block ethylene biosynthesis by inhibiting ACC oxidase. Du, S; Guo, H; He, W; Ji, C; Li, H; Li, Y; Raikhel, N; Sun, X; Wang, Y; Xia, P; Xiao, J, 2017)	2.17
"Ethylene is a major plant hormone mediating developmental processes and stress responses to stimuli such as infection. "	( Ethylene, an early marker of systemic inflammation in humans. Beest, MT; Bendix, MB; Cristescu, SM; Dingjan, I; Harren, FJM; Kox, M; Marczin, N; Neerincx, AH; Paardekooper, LM; Pickkers, P; Risby, T; van den Bogaart, G, 2017)	3.34
"Ethylene is a gaseous plant hormone perceived by a family of receptors in Arabidopsis ("	( Ethylene Receptors Signal via a Noncanonical Pathway to Regulate Abscisic Acid Responses. Bakshi, A; Binder, BM; Chervin, C; Fernandez, JC; Hewezi, T; Piya, S, 2018)	3.37
"Ethylene acts as an inhibitor of the nodulation process of leguminous plants. "	( The expression of an exogenous ACC deaminase by the endophyte Serratia grimesii BXF1 promotes the early nodulation and growth of common bean. Glick, BR; Nascimento, FX; Rossi, MJ; Tavares, MJ, 2018)	1.92
"Ethylene is an essential component for plant growth and development and in response to drought."	( Molecular Insights into the Involvement of a Never Ripe Receptor in the Interaction Between Two Beneficial Soil Bacteria and Tomato Plants Under Well-Watered and Drought Conditions. Aroca, R; Ibort, P; Molina, S; Ruiz-Lozano, JM, 2018)	1.2
"Ethylene is a phytohormone involved in the regulation of several aspects of plant development and in responses to biotic and abiotic stress. "	( The FBH family of bHLH transcription factors controls ACC synthase expression in sugarcane. Alessio, VM; Cavaçana, N; Dantas, LLB; Hotta, CT; Imaizumi, T; Lee, N; Menossi, M, 2018)	1.92
"Ethylene is a natural aging hormone in plants, and controlling its concentration has long been a subject of research aimed at reducing wastage during packaging, transport, and storage. "	( Absorption of Ethylene on Membranes Containing Potassium Permanganate Loaded into Alumina-Nanoparticle-Incorporated Alumina/Carbon Nanofibers. Han, D; Steckl, AJ; Tirgar, A, 2018)	2.28
"Ethylene is an important plant hormone that controls many physiological processes in plants. "	( Parallel online determination of ethylene release rate by Shaken Parsley cell cultures using a modified RAMOS device. Büchs, J; Conrath, U; Korona, A; Krömke, H; Nolten, J; Schillheim, B; Schilling, JV; Schulte, A; Vennekötter, JB; Wessling, M, 2018)	2.2
"Ethylene is a phytohormone that has gained importance through its role in stress tolerance and fruit ripening. "	( Functional characterization of 1-aminocyclopropane-1-carboxylic acid oxidase gene in Arabidopsis thaliana and its potential in providing flood tolerance. Basu, C; Gupta, D; Joshee, N; Ramadoss, N; Vaidya, BN, 2018)	1.92
"Ethylene is an important plant hormone that is involved in a variety of developmental processes including agriculturally important ripening of certain fruits. "	( Olefin Metathesis-Based Fluorescent Probes for the Selective Detection of Ethylene in Live Cells. Calkins, RT; Lee, S; Michel, BW; Toussaint, SNW, 2018)	2.15
"Ethylene is a gas and a plant hormone with wide ranging effects and a well defined signaling pathway. "	( An Evolutionary Perspective on Ethylene Sensing in Microorganisms. Binder, BM; Papon, N, 2019)	2.24
"Ethylene acts as a major regulator of the nodulation process of leguminous plants. "	( ACC deaminase plays a major role in Pseudomonas fluorescens YsS6 ability to promote the nodulation of Alpha- and Betaproteobacteria rhizobial strains. Ali, S; Franck, J; Glick, BR; Nascimento, FX; Rossi, MJ; Tavares, MJ, 2019)	1.96
"Ethylene is a volatile alkene which is used in large commercial scale as a precursor in plastic industry, and is currently derived from petroleum refinement. "	( Enhanced stable production of ethylene in photosynthetic cyanobacterium Synechococcus elongatus PCC 7942. Aro, EM; Carbonell, V; Kallio, P; Vuorio, E, 2019)	2.25
"Ethylene is an important plant hormone that regulates developmental processes in plants. "	( A type III ACC synthase, ACS7, is involved in root gravitropism in Arabidopsis thaliana. Chang, CL; Chang, IF; Hsu, PH; Huang, SJ; Tsai, MC; Wang, PH, 2013)	1.83
"Ethylene is an important plant hormone that regulates numerous cellular processes and stress responses. "	( Stable isotope metabolic labeling-based quantitative phosphoproteomic analysis of Arabidopsis mutants reveals ethylene-regulated time-dependent phosphoproteins and putative substrates of constitutive triple response 1 kinase. Cheng, H; Guo, G; Hu, Q; Lam, H; Li, J; Li, N; Liu, CY; Xue, Y; Yang, Z; Zhang, M, 2013)	2.04
"Ethylene is a well-known inducer of senescence, including fruit ripening and flower and leaf senescence."	( Ethylene-insensitive3 is a senescence-associated gene that accelerates age-dependent leaf senescence by directly repressing miR164 transcription in Arabidopsis. Guo, H; Li, Z; Peng, J; Wen, X, 2013)	2.55
"Ethylene is a classical plant hormone involved in the control of senescence and abscission, but its role in nitrogen-dependent leaf longevity is largely unknown."	( Linking ethylene to nitrogen-dependent leaf longevity of grass species in a temperate steppe. Chen, S; Han, X; Huang, J; Jiang, L; Ren, H; Wang, L; Xu, Z; Zhang, W, 2013)	1.55
"Ethylene is a key signal in the regulation of plant defense responses. "	( GDSL LIPASE1 modulates plant immunity through feedback regulation of ethylene signaling. Chung, JH; Guo, H; Jang, YJ; Kim, HG; Kwon, SJ; Na, YC; Nam, MH; Park, OK, 2013)	2.07
"Ethylene is a hormone that affects many processes important for plant growth, development, and responses to stresses. "	( How plants sense ethylene gas--the ethylene receptors. Binder, BM; Lacey, RF, 2014)	2.18
"Ethylene is an essential plant hormone also known as a stress hormone because its synthesis is accelerated by induction of a variety of biotic and abiotic stress. "	( Recent developments in use of 1-aminocyclopropane-1-carboxylate (ACC) deaminase for conferring tolerance to biotic and abiotic stress. Gontia-Mishra, I; Sasidharan, S; Tiwari, S, 2014)	1.85
"Ethylene is a gaseous ripening phytohormone of fruits and plants. "	( Ethylene detection in fruit supply chains. Bauersfeld, ML; Blanke, M; Janssen, S; Lang, W; Schmitt, K; Wöllenstein, J, 2014)	3.29
"Ethylene is an industrially important compound, but more sustainable production methods are desirable. "	( Engineered platform for bioethylene production by a cyanobacterium expressing a chimeric complex of plant enzymes. Hosoda, A; Ito, Y; Jindou, S; Mito, N; Tamura, H; Uematsu, K, 2014)	2.14
"This ethylene burst serves as a signal to ensure water recovery in flowers, and promotes flower opening by influencing the expression of a set of rehydration-responsive genes."	( Precise spatio-temporal modulation of ACC synthase by MPK6 cascade mediates the response of rose flowers to rehydration. Ali Khan, M; Gao, J; Li, N; Liu, X; Ma, N; Meng, Y; Su, Z; Wu, L; You, Q; Zhang, Q, 2014)	0.86
"Ethylene is a key hormone in plant development, mediating plant responses to abiotic environmental stress, and interactions with attackers and mutualists. "	( The evolution of ethylene signaling in plant chemical ecology. Groen, SC; Whiteman, NK, 2014)	2.18
"Ethylene is a stress hormone with contrasting effects on herbivore resistance. "	( Contrasting effects of ethylene biosynthesis on induced plant resistance against a chewing and a piercing-sucking herbivore in rice. Erb, M; Ju, H; Li, J; Liu, X; Lou, Y; Lu, J; Wang, X, 2014)	2.16
"Ethylene is a regulator of multiple plant processes, and is affected by many biotic and abiotic stresses."	( Cadmium-induced ethylene production and responses in Arabidopsis thaliana rely on ACS2 and ACS6 gene expression. Cuypers, A; Prinsen, E; Remans, T; Schellingen, K; Van Der Straeten, D; Vandenbussche, F; Vangronsveld, J, 2014)	1.47
"Ethylene is a plant hormone widely used to ripen fruit. "	( Ethylene-producing bacteria that ripen fruit. Aor, B; Avi, D; Del Bianco, C; Digiacomo, F; Dorigato, A; Ferrentino, G; Girelli, G; Jousson, O; Mansy, SS; Marchioretti, C; Pedrotti, M; Perli, T; Tonon, E; Torre, P; Valentini, V, 2014)	3.29
"Ethylene is a key factor regulating sex expression in cucurbits. "	( Effect of CRC::etr1-1 transgene expression on ethylene production, sex expression, fruit set and fruit ripening in transgenic melon (Cucumis melo L.). Beaudry, RM; Grumet, R; Switzenberg, JA, 2015)	2.12
"Ethylene is a trigger and usually accelerates the senescence rate, while cytokinins are known to delay it."	( Effect of cytokinins on delaying petunia flower senescence: a transcriptome study approach. Cocetta, G; Ferrante, A; Mensuali-Sodi, A; Trivellini, A; Vernieri, P, 2015)	1.14
"Ethylene is a gaseous hormone that regulates many processes involved in plant growth, development and stress responses. "	( Tobacco ankyrin protein NEIP2 interacts with ethylene receptor NTHK1 and regulates plant growth and stress responses. Cao, YR; Chen, HW; Chen, SY; Li, ZG; Ma, B; Tao, JJ; Zhang, JS; Zhang, WK, 2015)	2.12
"Ethylene is an important factor that stimulates Hevea brasiliensis to produce natural rubber. "	( Isolation and molecular characterization of 1-aminocyclopropane-1-carboxylic acid synthase genes in Hevea brasiliensis. Chang, WJ; Xu, J; Zhang, ZL; Zhu, JH, 2015)	1.86
"Ethylene is an essential element in controlling latex production."	( Ethylene Response Factors Are Controlled by Multiple Harvesting Stresses in Hevea brasiliensis. Bonnot, F; Chaidamsari, T; Dessailly, F; Duan, C; Herlinawati, E; Hu, S; Leclercq, J; Montoro, P; Pirrello, J; Piyatrakul, P; Putranto, RA; Rio, M; Tang, C, 2015)	2.58
"Ethylene is an important phytohormone in the regulation of plant growth, development, and stress response throughout the lifecycle. "	( Tobacco Translationally Controlled Tumor Protein Interacts with Ethylene Receptor Tobacco Histidine Kinase1 and Enhances Plant Growth through Promotion of Cell Proliferation. Cao, YR; Chen, HW; Chen, SY; Li, QT; Ma, B; Tao, JJ; Wei, W; Zhang, JS; Zhang, WK, 2015)	2.1
"Ethylene is a gaseous plant hormone that most likely became a functional hormone during the evolution of charophyte green algae, prior to land colonization. "	( Ethylene and Hormonal Cross Talk in Vegetative Growth and Development. Smet, D; Van de Poel, B; Van Der Straeten, D, 2015)	3.3
"Ethylene is a phytohormone known for inducing a triple response in seedlings, leaf abscission and other responses to various stresses. "	( Implications of ethylene biosynthesis and signaling in soybean drought stress tolerance. Albuquerque, EV; Arraes, FB; Beneventi, MA; Grossi-de-Sa, MF; Lisei de Sa, ME; Marin, SR; Nepomuceno, AL; Paixao, JF; Purgatto, E, 2015)	2.21
"Ethylene is a stimulant to increase natural rubber latex. "	( Comprehensive Proteomics Analysis of Laticifer Latex Reveals New Insights into Ethylene Stimulation of Natural Rubber Production. Chang, L; Huang, Q; Jin, X; Meng, X; Sun, Y; Tong, Z; Wang, D; Wang, L; Wang, X; Yang, Q, 2015)	2.09
"Ethylene (ET) is an important hormone in plant responses to microbial pathogens and herbivorous insects, and in the interaction of plants with beneficial microbes and insects. "	( Ethylene: Traffic Controller on Hormonal Crossroads to Defense. Broekgaarden, C; Caarls, L; Pieterse, CM; Van Wees, SC; Vos, IA, 2015)	3.3
"Ethylene is a gaseous phytohormone that plays vital roles in plant growth and development. "	( EIN2-directed translational regulation of ethylene signaling in Arabidopsis. An, F; Feng, Y; Guo, H; Li, H; Li, M; Li, W; Ma, M; Ma, Y; Wang, Y, 2015)	2.12
"Ethylene gas is a major plant hormone that influences diverse processes in plant growth, development and stress responses throughout the plant life cycle. "	( Q&A: How do plants respond to ethylene and what is its importance? Chang, C, 2016)	2.17
"Ethylene (ET) is a gaseous plant hormone that plays essential roles in biotic and abiotic stress responses in plants. "	( Ethylene positively regulates cold tolerance in grapevine by modulating the expression of ETHYLENE RESPONSE FACTOR 057. Chen, L; Fang, L; Gan, S; Karungo, SK; Li, S; Ren, X; Sun, X; Wang, Y; Xin, H; Zhao, T, 2016)	3.32
"Ethylene is a plant hormone that plays a crucial role in the growth and development of plants. "	( Ethylene Regulates the Physiology of the Cyanobacterium Synechocystis sp. PCC 6803 via an Ethylene Receptor. Binder, BM; Lacey, RF, 2016)	3.32
"Ethylene is an essential hormone in plants that is involved in low-oxygen and reoxygenation responses. "	( Ethylene-Regulated Glutamate Dehydrogenase Fine-Tunes Metabolism during Anoxia-Reoxygenation. Lin, CY; Shih, MC; Ting, CY; Tsai, KJ, 2016)	3.32
"Ethylene is an important phytohormone in the regulation of plant growth, development and stress response."	( LcMKK, a MAPK kinase from Lycium chinense, confers cadmium tolerance in transgenic tobacco by transcriptional upregulation of ethylene responsive transcription factor gene. Guan, C; Ji, J; Jin, C; Li, X; Wang, G, 2016)	1.36
"Ethylene is thought to be a strong inhibitor of flowering in short day plants (SDPs), whereas the involvement of abscisic acid (ABA) in the regulation of flowering of plants is not well understood."	( Ethylene and ABA interactions in the regulation of flower induction in Pharbitis nil. Kesy, J; Kopcewicz, J; Wilmowicz, E, 2008)	2.51
"Ethylene is an important regulator of plant growth, development and responses to environmental stresses. "	( Involvement of RTE1 in conformational changes promoting ETR1 ethylene receptor signaling in Arabidopsis. Chang, C; Resnick, JS; Rivarola, M, 2008)	2.03
"Ethylene is a simple gaseous hormone in plants. "	( Genetic basis of ethylene perception and signal transduction in Arabidopsis. Guo, H; Zhu, Z, 2008)	2.13
"Ethylene signaling is a component of the plant's response to low potassium that stimulates the production of reactive oxygen species and is important for changes in root morphology and whole plant tolerance to low potassium conditions."	( Ethylene mediates response and tolerance to potassium deprivation in Arabidopsis. Jung, JY; Schachtman, DP; Shin, R, 2009)	2.52
"Ethylene (C(2)H(4)) is a unique plant-signaling molecule that regulates numerous developmental processes. "	( A combinatorial interplay among the 1-aminocyclopropane-1-carboxylate isoforms regulates ethylene biosynthesis in Arabidopsis thaliana. Alonso, JM; Ecker, JR; Gao, S; Jin, H; Theologis, A; Tsuchisaka, A; Yu, G; Zhang, X, 2009)	2.02
"Ethylene is a gaseous plant hormone used in many physiological studies examining its role in plant growth and development. "	( Preparation of ethylene gas and comparison of ethylene responses induced by ethylene, ACC, and ethephon. Wen, CK; Zhang, W, 2010)	2.16
"Ethylene serves as an important hormone controlling several aspects of plant growth and development, including fruit ripening and leaf and petal senescence. "	( Regulated ethylene insensitivity through the inducible expression of the Arabidopsis etr1-1 mutant ethylene receptor in tomato. Gallie, DR, 2010)	2.21
"Ethylene is an essential regulator of flower development in Cucurbita pepo, controlling the sexual expression, and the differentiation and maturation of floral organs. "	( Cloning and characterisation of two CTR1-like genes in Cucurbita pepo: regulation of their expression during male and female flower development. Garrido, D; Gómez, P; Jamilena, M; Manzano, S; Martínez, C, 2010)	1.8
"Ethylene signaling is a complex pathway that has been intensively analyzed partly due to its importance to the manifestation of horticultural phenomena, including fruit ripening and tissue senescence. "	( FERONIA is a key modulator of brassinosteroid and ethylene responsiveness in Arabidopsis hypocotyls. Deslauriers, SD; Larsen, PB, 2010)	2.06
"Ethylene is an important plant gas hormone, and the amino acid Glu is emerging as a messenger molecule in plants. "	( Alleviation of salt stress-induced inhibition of seed germination in cucumber (Cucumis sativus L.) by ethylene and glutamate. Chang, C; Duo, L; Li, Y; Shi, L; Wang, B; Zhang, W, 2010)	2.02
"Ethylene is a gaseous hormone important for adaptation and survival in plants. "	( Identification of novel inhibitors of 1-aminocyclopropane-1-carboxylic acid synthase by chemical screening in Arabidopsis thaliana. Hsu, JH; Lin, LC; Wang, LC, 2010)	1.8
"Ethylene (ET) is a volatile hormone that modulates fruit ripening, plant growth, development and stress responses. "	( Proteomic responses in Arabidopsis thaliana seedlings treated with ethylene. Binder, BM; Chang, C; Chen, R; Cooper, B; Garrett, WM; Tucker, ML, 2011)	2.05
"Ethylene is a gaseous hormone whose sensitivity is a key factor to limiting its response in target cells."	( In silico characterization of putative members of the coffee (Coffea arabica) ethylene signaling pathway. Chalfun-Júnior, A; Lima, AA; Paiva, LV; Ságio, SA, 2011)	1.32
"Ethylene is an essential plant gaseous hormone that controls many aspects of plant growth and development, especially the fruit ripening. "	( Detecting adaptive evolution and functional divergence in aminocyclopropane-1-carboxylate synthase (ACS) gene family. Qiao, Q; Zhang, TC; Zhong, Y, 2012)	1.82
"Ethylene is an attractive alternative feedstock, as it can be derived from renewable biomass resources or harnessed from large domestic shale gas deposits."	( Synthesis of p-xylene from ethylene. Brookhart, M; Findlater, M; Guironnet, D; Lyons, TW, 2012)	1.4
"Ethylene (ET) is a gaseous phytohormone that participates in various plant physiological processes and essentially contributes to plant immunity. "	( Ethylene in mutualistic symbioses. Khatabi, B; Schäfer, P, 2012)	3.26
"Ethylene is a major plant hormone that plays an important role in regulating bolting, although the underlying molecular mechanism is not well understood. "	( Functional phosphoproteomic analysis reveals that a serine-62-phosphorylated isoform of ethylene response factor110 is involved in Arabidopsis bolting. Li, N; Li, Y; Liu, D; Zhu, L, 2013)	2.05
"Ethylene is a key regulator of this process and, in Arabidopsis thaliana, hyponasty is induced by this phytohormone via promotion of epidermal cell expansion in a proximal zone of the abaxial side of the petiole."	( Ethylene promotes hyponastic growth through interaction with ROTUNDIFOLIA3/CYP90C1 in Arabidopsis. Peeters, AJ; Pierik, R; Polko, JK; Strnad, M; Tarkowská, D; van Zanten, M; Voesenek, LA, 2013)	2.55
"Ethylene is an important hormonal regulator of plant growth that acts by regulating gene expression. "	( SCF-mediated proteolysis and negative regulation in ethylene signaling. Kepinski, S; Leyser, O, 2003)	2.01
"Ethylene (74-85-1) is an important petrochemical and is produced endogenously. "	( The effect of ethylene exposure on ethylene oxide in blood and on hepatic cytochrome p450 in Fischer rats. Fennell, TR; James, RA; Murphy, J; Parkinson, C; Snyder, RW, 2004)	2.13
"Ethylene is a plant hormone that promotes leaf damage in O3-exposed plants."	( Salicylic acid accumulation under O3 exposure is regulated by ethylene in tobacco plants. Aono, M; Ioki, M; Kamada, H; Kanna, M; Kubo, A; Nakajima, N; Ogawa, D; Saji, H; Sano, T; Tamaoki, M, 2005)	1.29
"Ethylene oxide (EO) is an important industrial chemical that is classified as a known human carcinogen (IARC, Group 1). "	( Effects of ethylene oxide and ethylene inhalation on DNA adducts, apurinic/apyrimidinic sites and expression of base excision DNA repair genes in rat brain, spleen, and liver. Asakura, S; Koc, H; Kosyk, O; Li, Y; Nakamura, J; Rusyn, I; Swenberg, JA; Upton, PB, 2005)	2.16
"Ethylene is a gaseous plant hormone involved in several important physiological processes throughout a plant's life cycle. "	( Molecular mechanisms of ethylene signaling in Arabidopsis. Alonso, JM; Benavente, LM, 2006)	2.08
"Ethylene is a gaseous plant growth regulator that controls a multitude of developmental and stress responses. "	( ETHYLENE-INSENSITIVE5 encodes a 5'-->3' exoribonuclease required for regulation of the EIN3-targeting F-box proteins EBF1/2. Aguilar-Henonin, L; An, F; Ecker, JR; Gregory, BD; Guo, H; Guzman, P; Li, H; Nourizadeh, SD; Olmedo, G, 2006)	3.22
"Ethylene is a plant hormone that regulates many aspects of growth and development. "	( Ethylene-induced stomatal closure in Arabidopsis occurs via AtrbohF-mediated hydrogen peroxide synthesis. Desikan, R; Hancock, JT; Harrett-Williams, R; Harter, K; Hooley, R; Last, K; Neill, SJ; Tagliavia, C, 2006)	3.22
"Ethylene is a plant hormone controlling a wide range of physiological processes in plants. "	( Tools to maintain postharvest fruit and vegetable quality through the inhibition of ethylene action: a review. Bailén, G; Castillo, S; Guillén, F; Martínez-Romero, D; Serrano, M; Valero, D; Valverde, JM; Zapata, P, 2007)	2.01
"Ethylene is a strong controller of root development, and it has been suggested that it is involved in the increase of lateral root development in nutrient-rich soil patches (selective root placement). "	( Evidence that ethylene signalling is not involved in selective root placement by tobacco plants in response to nutrient-rich soil patches. Bögemann, GM; Bouma, TJ; De Bruin, S; De Kroon, H; Smeets, M; Visser, EJW, 2008)	2.15
"Ethylene is an important plant growth regulator perceived by membrane-bound ethylene receptors. "	( Subcellular co-localization of Arabidopsis RTE1 and ETR1 supports a regulatory role for RTE1 in ETR1 ethylene signaling. Chang, C; Dong, CH; Maggin, BD; Resnick, JS; Rivarola, M, 2008)	2
"Ethylene is a plant hormone important in many aspects of plant growth and development such as germination, fruit ripening, and senescence. "	( The nature of O2 activation by the ethylene-forming enzyme 1-aminocyclopropane-1-carboxylic acid oxidase. Klinman, JP; Mirica, LM, 2008)	2.07
"Ethylene is a gaseous plant hormone involved in many physiological processes including senescence, fruit ripening, and defence. "	( Tissue-specific PhBPBT expression is differentially regulated in response to endogenous ethylene. Clark, DG; Dexter, RJ; Schmelz, EA; Shibuya, K; Underwood, BA; Verdonk, JC, 2008)	2.01
"Ethylene (C2H4) is a gaseous hormone that affects many aspects of plant growth and development. "	( A dominant mutant receptor from Arabidopsis confers ethylene insensitivity in heterologous plants. Bleecker, AB; Chang, C; Clark, DG; Klee, HJ; Lanahan, MB; Meyerowitz, EM; Wilkinson, JQ, 1997)	1.99
"Ethylene is a potent inhibitor of cortical cell division, an effect that can be counteracted by applying silver ions (Ag+) or aminoethoxy-vinylglycine (AVG)."	( Ethylene provides positional information on cortical cell division but is not involved in Nod factor-induced root hair tip growth in Rhizobium-legume interaction. Bisseling, T; Emons, AM; Heidstra, R; Peck, S; van Kammen, A; Yalcin, Y; Yang, WC, 1997)	2.46
"Ethylene is an important regulator of plant growth. "	( RESPONSIVE-TO-ANTAGONIST1, a Menkes/Wilson disease-related copper transporter, is required for ethylene signaling in Arabidopsis. Alonso, JM; Dailey, WP; Dancis, A; Ecker, JR; Guzman, P; Hirayama, N; Hirayama, T; Kieber, JJ; Kogan, M; Nourizadeh, S, 1999)	1.96
"Ethylene (ET) is a gaseous olefin of considerable industrial importance. "	( A physiological toxicokinetic model for exogenous and endogenous ethylene and ethylene oxide in rat, mouse, and human: formation of 2-hydroxyethyl adducts with hemoglobin and DNA. Baur, C; Csanády, GA; Denk, B; Filser, JG; Gargas, ML; Kessler, W; Kreuzer, PE; Pütz, C, 2000)	1.99
"Ethylene is a widely distributed alkene product which is formed enzymatically (e.g., in plants) or by photochemical reactions (e.g., in the upper oceanic layers from dissolved organic carbon). "	( Modulation of intracellular calcium and proliferative activity of invertebrate and vertebrate cells by ethylene. Gamulin, V; Müller, WE; Perovic, S; Schröder, HC; Seack, J, 2001)	1.97
"Ethylene is a plant hormone involved in a large number of developmental processes."	( The ethylene pathway: a paradigm for plant hormone signaling and interaction. Alonso, JM; Ecker, JR, 2001)	1.59

Excerpt	Reference	Relevance
"As ethylene has an antagonistic effect on ABA-induced stomatal closure, the possibility that the antagonistic effects of these phytohormones on ABA were mediated through ethylene biosynthesis was investigated."	( Cytokinin and auxin inhibit abscisic acid-induced stomatal closure by enhancing ethylene production in Arabidopsis. Hasezawa, S; Kondo, N; Nakajima, N; Sano, T; Tamaoki, M; Tanaka, Y, 2006)	1.07
"Ethylene has long been used to promote flowering in pineapple production. "	( Integrated DNA methylome and transcriptome analysis reveals the ethylene-induced flowering pathway genes in pineapple. Ao, M; Fu, Y; Lei, M; Li, Z; Wang, J; Xu, L; Zhao, J, 2017)	2.14
"Ethylene has long been considered as a key regulator of the abscission process."	( Re-evaluation of the ethylene-dependent and -independent pathways in the regulation of floral and organ abscission. Meir, S; Patterson, SE; Philosoph-Hadas, S; Riov, J; Roberts, JA; Tucker, ML, 2019)	1.55
"Ethylene has long been considered the key regulator of ripening in climacteric fruit. "	( TIR1-like auxin-receptors are involved in the regulation of plum fruit development. Bouzayen, M; El-Sharkawy, I; Jayasankar, S; Jones, B; Kumar, PP; Mila, I; Sherif, SM, 2014)	1.85
"Ethylene has been regarded as a stress hormone to regulate myriad stress responses. "	( Salt-induced stabilization of EIN3/EIL1 confers salinity tolerance by deterring ROS accumulation in Arabidopsis. Guo, H; Li, W; Li, Z; Peng, J; Shi, H; Wen, X; Yang, L; Zhu, H, 2014)	1.85
"Ethylene has been shown to also regulate many other hormones' signaling pathways including auxin, abscisic acid and jasmonic acid, implying the existence of complicated signaling networks in the growth, development and defense responses of various plants."	( Genetic basis of ethylene perception and signal transduction in Arabidopsis. Guo, H; Zhu, Z, 2008)	1.41
"Ethylene receptors have been identified and are known to be negative regulators of ethylene signalling."	( Apple ethylene receptor protein concentrations are affected by ethylene, and differ in cultivars that have different storage life. Hayama, H; Nakamura, Y; Tatsuki, M, 2009)	1.56
"Ethylene biosynthesis has been implicated to be important for blast resistance; however, the individual roles of ethylene and cyanide, which are produced from the precursor 1-aminocyclopropane-1-carboxylic acid, remain unevaluated."	( Cyanide, a coproduct of plant hormone ethylene biosynthesis, contributes to the resistance of rice to blast fungus. Feng, J; Hasegawa, M; Iwai, T; Mitsuhara, I; Ohashi, Y; Seo, S, 2011)	1.36
"Ethylene has been found to suppress hypocotyl elongation in darkness while promoting it in light."	( A molecular framework of light-controlled phytohormone action in Arabidopsis. Deng, XW; Guo, H; Li, J; Quail, PH; Shi, H; Wang, L; Xi, Y; Xue, C; Zhong, S, 2012)	1.1
"Ethylene has long been recognized as a growth inhibitor, but evidence is accumulating that ethylene can also promote growth."	( The Janus face of ethylene: growth inhibition and stimulation. Pierik, R; Poorter, H; Tholen, D; Visser, EJ; Voesenek, LA, 2006)	1.39
"As ethylene has an antagonistic effect on ABA-induced stomatal closure, the possibility that the antagonistic effects of these phytohormones on ABA were mediated through ethylene biosynthesis was investigated."	( Cytokinin and auxin inhibit abscisic acid-induced stomatal closure by enhancing ethylene production in Arabidopsis. Hasezawa, S; Kondo, N; Nakajima, N; Sano, T; Tamaoki, M; Tanaka, Y, 2006)	1.07
"Ethylene has been regarded as a stress hormone involved in many stress responses. "	( Expression of tobacco ethylene receptor NTHK1 alters plant responses to salt stress. Cao, WH; Cao, YR; Chen, SY; Du, BX; Liu, J; Zhang, JS; Zheng, SF; Zhou, QY, 2006)	2.09
"Ethylene has been hypothesised to be a regulator of root nodule development in legumes, but its molecular mechanisms of action remain unclear. "	( Identification of ethylene-mediated protein changes during nodulation in Medicago truncatula using proteome analysis. Imin, N; Mathesius, U; Prayitno, J; Rolfe, BG, 2006)	2.11
"Ethylene signaling has been implicated in the induction of these chemical defenses."	( Aminocyclopropane carboxylic acid synthase is a regulated step in ethylene-dependent induced conifer defense. Full-length cDNA cloning of a multigene family, differential constitutive, and wound- and insect-induced expression, and cellular and subcellular Bohlmann, J; Franceschi, VR; Hudgins, JW; Jancsik, S; Ralph, SG, 2007)	1.3
"Ethylene has long been regarded as the main regulator of ripening in climacteric fruits. "	( The involvement of auxin in the ripening of climacteric fruits comes of age: the hormone plays a role of its own and has an intense interplay with ethylene in ripening peaches. Casadoro, G; Tadiello, A; Trainotti, L, 2007)	1.98
"Ethylene has been shown to promote early plant senescence while controlled atmospheres (CA; reduced O2 levels and elevated CO2 levels) can delay its onset and/or severity."	( The effects of ethylene, depressed oxygen and elevated carbon dioxide on antioxidant profiles of senescing spinach leaves. Forney, CF; Hodges, DM, 2000)	1.38
"Ethylene has no effect on the expression of the auxin-induced mRNAs."	( Molecular cloning of cDNAs for auxin-induced mRNAs and developmental expression of the auxin-inducible genes. Jena, PK; Mukherjee, SK; Poovaiah, BW; Reddy, AS, 1990)	1

Excerpt	Reference	Relevance
"Ethylene plays essential roles in adaptive growth of rice (Oryza sativa). "	( Rice EIL1 interacts with OsIAAs to regulate auxin biosynthesis mediated by the tryptophan aminotransferase MHZ10/OsTAR2 during root ethylene responses. Chen, SY; Chu, JF; Hu, Y; Huang, YH; Ma, B; Tao, JJ; Wei, W; Xin, PY; Yin, CC; Zhang, JS; Zhang, WK; Zhou, Y, 2022)	2.37
"Ethylene plays a crucial role in regulating fruit ripening, quality, and defense response. "	( Comparative proteomic analysis of wild-type and a SlETR-3 (Nr) mutant reveals an ethylene-induced physiological regulatory network in fresh-cut tomatoes. Gao, LP; Liu, J; Shi, JY; Wang, Q; Zheng, SF; Zuo, JH, 2022)	2.39
"Ethylene plays an important role in plant growth and development, including the determination of plant height."	( Citrus ACC synthase CiACS4 regulates plant height by inhibiting gibberellin biosynthesis. Chu, LL; Hu, CG; Liu, HQ; Sheng, XX; Wang, QY; Yan, Z; Zeng, RF; Zhang, JZ, 2023)	1.63
"Ethylene (ETH) plays important roles in various development programs and stress responses in plants. "	( Dissecting the effect of ethylene in the transcriptional regulation of chilling treatment in grapevine leaves. Gong, L; Hou, Y; Li, Q; Liang, J; Liang, Z; Ren, H; Wang, Q; Wong, DCJ; Xin, H; Zhou, H; Zhu, Z, 2023)	2.66
"Ethylene plays a pivotal role in a wide range of developmental, physiological, and defense processes in plants. "	( Role of EIN2-mediated ethylene signaling in regulating petal senescence, abscission, reproductive development, and hormonal crosstalk in tobacco. Bharti, S; Chakrabarti, M, 2023)	2.67
"Ethylene plays essential roles in rice growth, development and stress adaptation. "	( A translational regulator MHZ9 modulates ethylene signaling in rice. Cao, WQ; Chen, SY; Han, JQ; Huang, YH; Li, XK; Ma, B; Qian, W; Tao, JJ; Wei, W; Xiong, Q; Yang, C; Yin, CC; Zhang, JS; Zhang, WK; Zhang, X; Zhao, H; Zhao, R; Zhou, Y, 2023)	2.62
"Ethylene plays an essential role in the development of cotton fibres. "	( GhXB38D represses cotton fibre elongation through ubiquitination of ethylene biosynthesis enzymes GhACS4 and GhACO1. Du, C; Gao, W; Song, Q; Sun, W; Wang, J; Zuo, K, 2023)	2.59
"Ethylene plays important roles in plant growth and development, but the regulation of ethylene signaling is largely unclear, especially in crops such as rice ("	( The GDSL Lipase MHZ11 Modulates Ethylene Signaling in Rice Roots. Chen, SY; Chu, JF; Duan, KX; Li, XK; Lu, X; Ma, B; Man Lam, S; Shui, GH; Tao, JJ; Wei, W; Xin, PY; Yin, CC; Zhang, JS; Zhang, WK; Zhao, H, 2020)	2.28
"Ethylene plays an important role in stress adaptation and fruit ripening. "	( Overexpression of Guo, T; Jiang, Q; Li, Y; Liu, C; Ma, F; Wang, N; Wu, J; Zhang, X, 2020)	2
"Ethylene plays a critical regulatory role in the cold stress response, but the underlying molecular mechanisms remain elusive."	( Ethylene increases the cold tolerance of apple via the MdERF1B-MdCIbHLH1 regulatory module. Chen, X; Jiang, H; Jiang, S; Liu, W; Mao, Z; Su, M; Wang, N; Wang, Y; Xu, H; Zhang, J; Zhang, Z, 2021)	2.79
"Ethylene plays critical roles in plant development and biotic stress response, but the mechanism of ethylene in host antiviral response remains unclear. "	( A viral protein promotes host SAMS1 activity and ethylene production for the benefit of virus infection. Hong, W; Ji, S; Li, Y; Wang, Y; Wei, C; Wu, J; Zhang, J; Zhao, S; Zhu, S, 2017)	2.15
"Ethylene plays pleiotropic roles in plant growth, plant development, and stress responses. "	( Histone Deacetylases SRT1 and SRT2 Interact with ENAP1 to Mediate Ethylene-Induced Transcriptional Repression. Ko, EE; Qiao, H; Shao, K; Wang, L; Zhang, F, 2018)	2.16
"Ethylene signaling plays a major role in the regulation of plant growth, but its cross-talk with other phytohormones is still poorly understood. "	( Ethylene signaling cross-talk with other hormones in Arabidopsis thaliana exposed to contrasting phosphate availability: Differential effects in roots, leaves and fruits. Müller, M; Munné-Bosch, S; Simancas, B, 2018)	3.37
"Ethylene plays an important role in the grape rachis, where its production can be 10 times higher than in the berry. "	( Expression of grape ACS1 in tomato decreases ethylene and alters the balance between auxin and ethylene during shoot and root formation. An, D; Cheng, J; Feng, J; Fu, M; Li, J; Liu, Y; Tan, B; Wang, W; Ye, X; Zheng, X, 2018)	2.18
"Ethylene can enhance reddening of apple (Malus × domestica), but the regulatory mechanism is poorly understood."	( The ethylene response factor MdERF1B regulates anthocyanin and proanthocyanidin biosynthesis in apple. Chen, X; Fang, H; Jiang, S; Su, M; Wang, N; Wang, Y; Xu, H; Xu, L; Yang, G; Zhang, J; Zhang, Z, 2018)	1.76
"Ethylene plays a critical role in many diverse processes in plant development. "	( Ectopic expression of ARGOS8 reveals a role for ethylene in root-lodging resistance in maize. Beatty, M; Brugire, N; Drummond, BJ; Habben, JE; Hakimi, SM; Lafitte, HR; Mo, H; O'Neill, D; Schussler, JR; Shi, J; Weers, BP; Zastrow-Hayes, G, 2019)	2.21
"Ethylene promotes fruit ripening whereas 1-methylcyclopropene (1-MCP), a non-toxic antagonist of ethylene, delays fruit ripening via the inhibition of ethylene receptor. "	( Transcriptomic analysis reveals key factors in fruit ripening and rubbery texture caused by 1-MCP in papaya. Chen, W; Ding, X; Gao, Q; Huang, J; Li, X; Tan, Q; Xiao, S; Ye, L; Zhu, X, 2019)	1.96
"Ethylene plays an important role in ripening and senescence in many climacteric fruit."	( A proteomic investigation of apple fruit during ripening and in response to ethylene treatment. Campbell-Palmer, L; Cui, Y; Li, L; Li, X; Song, J; Thompson, K; Walker, B; Zheng, Q, 2013)	1.34
"Ethylene plays an important role in fruit tolerance to environmental stress."	( LeMAPK4 participated in cold-induced ethylene production in tomato fruit. Lv, S; Shen, L; Sheng, J; Xie, H; Yu, M; Zhao, R; Zheng, Y, 2013)	1.38
"Ethylene plays an important role in regulating petal cell expansion during rose flower opening."	( Integrative analysis of miRNA and mRNA profiles in response to ethylene in rose petals during flower opening. Chen, J; Fei, Z; Gao, J; Li, J; Ma, N; Pei, H; Tian, J; Zhang, S; Zheng, Y, 2013)	1.35
"Ethylene plays essential roles in adaptive growth of rice plants in water-saturating environment; however, ethylene signaling pathway in rice is largely unclear. "	( Identification of rice ethylene-response mutants and characterization of MHZ7/OsEIN2 in distinct ethylene response and yield trait regulation. Chen, H; Chen, HW; Chen, SY; Duan, KX; He, SJ; Lu, TG; Lu, X; Ma, B; Song, QX; Xiong, Q; Yang, C; Yin, CC; Zhang, JS; Zhang, WK, 2013)	2.14
"Ethylene plays a pivotal role in the growth of seedlings under light or dark during early development."	( A chemical genetics approach reveals a role of brassinolide and cellulose synthase in hypocotyl elongation of etiolated Arabidopsis seedlings. Chen, IJ; Cheuh, CM; Chuang, JY; Fan, YS; Lin, LC; Lo, WS; Wang, LC; Wu, SJ, 2013)	1.11
"Ethylene plays an important role in organ growth. "	( A DELLA gene, RhGAI1, is a direct target of EIN3 and mediates ethylene-regulated rose petal cell expansion via repressing the expression of RhCesA2. Chen, J; Gao, J; Li, J; Luo, J; Ma, N; Pei, H, 2013)	2.07
"Ethylene appeared to suppress an acceleration of both CgADH expression and fermentation, and alleviates ethanolic fermentation probably through by as a signal to acceleration of waterlogging-induced aerenchyma formation."	( Isolation of an alcohol dehydrogenase cDNA from and characterization of its expression in chrysanthemum under waterlogging. Ni, D; Song, L; Yin, D; Zhang, Z, 2013)	1.11
"Ethylene also plays a pivotal role in plant response or adaptation under biotic and abiotic stress conditions."	( Current understanding on ethylene signaling in plants: the influence of nutrient availability. Ferrante, A; Iqbal, N; Khan, NA; Masood, A; Trivellini, A, 2013)	1.41
"Ethylene plays important roles in plant growth, development and stress responses, and is perceived by a family of receptors that repress ethylene responses when ethylene is absent. "	( Association of cytochrome b5 with ETR1 ethylene receptor signaling through RTE1 in Arabidopsis. Chang, C; Chang, J; Clay, JM, 2014)	2.11
"Ethylene plays a crucial role in various biological processes and therefore its biosynthesis is strictly regulated by multiple mechanisms. "	( Arabidopsis protein phosphatase 2C ABI1 interacts with type I ACC synthases and is involved in the regulation of ozone-induced ethylene biosynthesis. Cieśla, A; Dąbrowski, M; Gałgański, Ł; Górska, A; Ibragimow, I; Kasprowicz-Maluśki, A; Kubiak, P; Ludwików, A; Małecka, A; Mituła, F; Piechalak, A; Sadowski, J; Szabat, M; Tajdel, M; Ziółkowski, PA, 2014)	2.05
"Ethylene, which promotes femaleness, is a key factor regulating sex expression."	( Floral primordia-targeted ACS (1-aminocyclopropane-1-carboxylate synthase) expression in transgenic Cucumis melo implicates fine tuning of ethylene production mediating unisexual flower development. Grumet, R; Hammar, SA; Little, HA; Switzenberg, JA, 2014)	1.33
"Ethylene regulates flower opening, together with at least gibberellins and auxin."	( Flower opening and closure: an update. Kamdee, C; van Doorn, WG, 2014)	1.12
"Ethylene seemed to inhibit growth, as the partially ethylene-insensitive genotype Never ripe (Nr) was much less sensitive to over-irrigation than the wild type."	( Inhibition of tomato shoot growth by over-irrigation is linked to nitrogen deficiency and ethylene. Dodd, IC; Fiebig, A, 2016)	1.38
"Ethylene plays an important role in flowers senescence."	( Functional characterization of PhGR and PhGRL1 during flower senescence in the petunia. Chen, G; Liu, J; Tan, Y; Tang, N; Yang, W; Yu, Y; Zhong, S, 2015)	1.14
"Ethylene plays important roles in plant growth, development, and stress responses. "	( MAOHUZI6/ETHYLENE INSENSITIVE3-LIKE1 and ETHYLENE INSENSITIVE3-LIKE2 Regulate Ethylene Response of Roots and Coleoptiles and Negatively Affect Salt Tolerance in Rice. Chen, H; Chen, SY; Duan, KX; He, SJ; Lu, X; Ma, B; Xiong, Q; Yang, C; Yin, CC; Zhang, JS, 2015)	2.28
"Ethylene plays critical roles in plant growth and development, including the regulation of cell expansion, senescence, and the response to biotic and abiotic stresses. "	( The ARGOS gene family functions in a negative feedback loop to desensitize plants to ethylene. Binder, BM; Bombyk, MM; Kim, HJ; Rai, MI; Schaller, GE; Shakeel, SN; Thibault, DM; Wang, X, 2015)	2.08
"Ethylene plays diverse roles in plant growth, development and stress responses. "	( Activation of ethylene signaling pathways enhances disease resistance by regulating ROS and phytoalexin production in rice. Cao, J; Chen, S; Chen, X; Huang, J; Jiang, L; Li, W; Liu, J; Liu, M; Meng, F; Miyamoto, K; Yamane, H; Yang, C; Yu, Y; Zhang, J; Zhang, Z, 2017)	2.26
"Ethylene plays a key role in various submergence responses of rice plants, but the mechanism of ethylene action remains largely unclear in rice. "	( Analysis of Growth and Molecular Responses to Ethylene in Etiolated Rice Seedlings. Ma, B; Zhang, JS, 2017)	2.16
"Ethylene plays a crucial role in apple fruit ripening. "	( Apple ethylene receptor protein concentrations are affected by ethylene, and differ in cultivars that have different storage life. Hayama, H; Nakamura, Y; Tatsuki, M, 2009)	2.28
"Ethylene plays a central role in hypoxic stress signaling, and G proteins have been recognized as crucial signal transducers in various hypoxic signaling pathways."	( G proteins as regulators in ethylene-mediated hypoxia signaling. Sauter, M; Steffens, B, 2010)	1.38
"This ethylene increase was accompanied by a loss of fruit firmness associated with chilling damage development."	( Temperature and ultra low oxygen effects and involvement of ethylene in chilling injury of 'Rojo Brillante' persimmon fruit. Lafuente, MT; Miranda, M; Orihuel-Iranzo, B; Zacarías, L, 2010)	1.06
"Ethylene plays a crucial role in the senescence of carnation (Dianthus caryophyllus L.) flowers."	( Transcriptional regulation of two RTE-like genes of carnation during flower senescence and upon ethylene exposure, wounding treatment and sucrose supply. Fu, Z; Liu, J; Wang, H; Wang, J; Yu, Y, 2011)	1.31
"Ethylene plays a key role in promoting fruit ripening, so altering its biosynthesis/signaling could be an important means to delay this process. "	( Nitric oxide counters ethylene effects on ripening fruits. Gupta, KJ; Lokesh, V; Manjunatha, G; Mur, LA; Neelwarne, B, 2012)	2.14
"• Ethylene plays a crucial role in plant resistance to necrotrophic pathogens, in which ETHYLENE RESPONSE FACTORs (ERFs) are often involved. "	( Arabidopsis RAP2.2 plays an important role in plant resistance to Botrytis cinerea and ethylene responses. Chen, Z; Gu, H; Qin, G; Qu, LJ; Wei, T; Yin, KQ; Zhao, Y, 2012)	1.32
"Ethylene levels were lower in the cultures treated with putrescine."	( Putrescine facilitated enhancement of capsaicin production in cell suspension cultures of Capsicum frutescens. Ravishankar, GA; Sudha, G, 2003)	1.04
"Ethylene also plays an important role in peg formation, but its relationship to auxin in this event is not understood."	( Possible involvement of CS-ACS1 and ethylene in auxin-induced peg formation of cucumber seedlings. Fujii, N; Saito, Y; Takahashi, H; Yamasaki, S, 2005)	1.32
"This ethylene increase may inhibit cell growth in the lower portion of the epicotyl and contribute to tip straightening and reduced overall curvature observed after the initial 60 min of curvature in etiolated pea epicotyls."	( Red light regulation of ethylene biosynthesis and gravitropism in etiolated pea stems. Harrison, MA; Steed, CL; Taylor, LK, 2004)	1.09
"Ethylene plays a critical role in initiation of rose flower senescence through regulating petal PCD."	( Involvement of ethylene and 1-aminocyclopropane-1-carboxylate synthase gene in regulation of programmed cell death during rose (Rosa x hybrida) flower development. Li, JH; Pan, HC; Wang, XZ, 2005)	1.4
"Ethylene promotes fruit ripening, including softening. "	( The involvement of 1-aminocyclopropane-1-carboxylic acid synthase isogene, Pp-ACS1, in peach fruit softening. Haji, T; Tatsuki, M; Yamaguchi, M, 2006)	1.78
"Ethylene may regulate flower opening mainly through expression of two ethylene receptor genes (Rh-ETR1 and Rh-ETR3) and two CTR (Rh-CTR1 and Rh-CTR2) genes."	( Transcriptional regulation of ethylene receptor and CTR genes involved in ethylene-induced flower opening in cut rose (Rosa hybrida) cv. Samantha. Gao, J; Li, Y; Liu, X; Ma, N; Tan, H; Xue, J, 2006)	1.34
"Ethylene signaling plays important roles in multiple aspects of plant growth and development. "	( Modulation of ethylene responses affects plant salt-stress responses. Cao, WH; Chen, SY; He, XJ; Liu, J; Mu, RL; Zhang, JS; Zhou, HL, 2007)	2.14
"Ethylene plays a key role in sex determination of cucumber flowers. "	( Correlation between development of female flower buds and expression of the CS-ACS2 gene in cucumber plants. Fujii, N; Fujita, Y; Matsuura, S; Miyazawa, Y; Mizusawa, H; Saito, S; Takahashi, H; Yamasaki, S, 2007)	1.78
"Ethylene did not produce statistically significant, exposure-related increases in the frequency of micronucleated PCE (MNPCE) in the bone marrow of either rats or mice when compared to air-exposed control animals."	( Effects of ethylene on micronucleus formation in the bone marrow of rats and mice following four weeks of inhalation exposure. Pritts, IM; Vergnes, JS, 1994)	1.4
"Ethylene induced an increase in the accumulation of 1-aminocyclopropane-1-carboxylate (ACC) oxidase transcript level and enzyme activity in the first internode of 5- to 6-day-old etiolated pea (Pisum sativum L.) seedlings. "	( Sequential induction of the ethylene biosynthetic enzymes by indole-3-acetic acid in etiolated peas. Kende, H; Peck, SC, 1995)	2.03
"Ethylene promotes the abscission of leaves and the ripening of fruits in pepper plants, and in both events an increase in cellulase activity is observed. "	( Differential ethylene-inducible expression of cellulase in pepper plants. Casadoro, G; Ferrarese, L; Moretto, P; Polverino de Laureto, P; Rascio, N; Trainotti, L, 1995)	2.1

Excerpt	Reference	Relevance
"Ethylene pretreatment alone altered the abundance of transcripts and proteins involved in hypoxia responses, root growth, translation, and reactive oxygen species (ROS) homeostasis."	( Ethylene augments root hypoxia tolerance via growth cessation and reactive oxygen species amelioration. Bailey-Serres, J; Bosman, F; de Deugd, F; Hartman, S; Hassall, KL; Hummel, M; Leeggangers, HACF; Liu, Z; Martopawiro, S; Rankenberg, T; Sasidharan, R; Su, P; Theodoulou, FL; van Veen, H; Voesenek, LACJ; Zhang, H, 2022)	2.89
"Upon ethylene treatment, the dephosphorylated Bβ mediates the formation of the A2-C4-Bβ protein complex to activate PP2A, resulting in the dephosphorylation of EIR1 to promote auxin transport in epidermis of elongation zone, leading to root growth inhibition."	( Phosphorylation status of Bβ subunit acts as a switch to regulate the function of phosphatase PP2A in ethylene-mediated root growth inhibition. Browning, KS; Burns, JG; Chen, X; Ke, M; Kotla, P; Qiao, H; Shao, Z; Tran, J; Zhao, B, 2022)	1.39
"Ethylene inhibitor treatment of soybean promotes flower bud differentiation and early flowering, suggested that there is a close relationship between ethylene signaling and soybean growth and development. "	( Multiplex CRISPR-Cas9 knockout of EIL3, EIL4, and EIN2L advances soybean flowering time and pod set. Cheng, Y; He, H; Li, Y; Liu, J; Yang, J; Yang, X; Zhang, X, 2023)	2.35
"Ethylene treatment resulted in a moderately more rapid flesh softening as a result of stronger expression of genes encoding expansin and cell wall hydrolases, especially xylosidase and galactosidase."	( Effect of Ethylene on Cell Wall and Lipid Metabolism during Alleviation of Postharvest Chilling Injury in Peach. Chen, K; Grierson, D; Wang, K; Wu, C; Xu, C; Yin, X; Zhang, B; Zhao, Y; Zhu, Y, 2019)	1.64
"Ethylene+H2S treatment also delayed the decreases in chlorophyll and total phenolics, and increased the accumulation of flavonoid, whereas decreased the contents of carotenoid, soluble protein in banana peel and reducing sugar in pulp compared with ethylene treatment alone."	( Hydrogen sulfide alleviates postharvest ripening and senescence of banana by antagonizing the effect of ethylene. Chen, XY; Ge, Y; Hu, KD; Hu, LY; Li, YH; Wang, SS; Yang, F; Yang, Y; Zhang, H, 2017)	1.39
"Ethylene treatment increased stem sucrose content but that occurred only in low-sugar genotype."	( Ethylene-mediated improvement in sucrose accumulation in ripening sugarcane involves increased sink strength. Chen, Z; Huang, D; Lakshmanan, P; Li, Y; Liao, F; Liao, Q; Liu, X; Long, M; Qin, C; Wang, M, 2019)	2.68
"Ethylene treatment increased a group of unique proteins that were not present during normal fruit ripening and have not been previously reported."	( A proteomic investigation of apple fruit during ripening and in response to ethylene treatment. Campbell-Palmer, L; Cui, Y; Li, L; Li, X; Song, J; Thompson, K; Walker, B; Zheng, Q, 2013)	1.34
"Ethylene treatment shortened the ripening of kiwifruits."	( Health-promoting effects of ethylene-treated kiwifruit 'Hayward' from conventional and organic crops in rats fed an atherogenic diet. Gorinstein, S; Jesion, I; Leontowicz, H; Leontowicz, M; Namiesnik, J; Park, YS; Rombolà, AD; Weisz, M, 2013)	1.41
"Upon ethylene treatment, etiolated MHZ7-overexpressing seedlings exhibit enhanced coleoptile elongation, increased mesocotyl growth and extremely twisted short roots, featuring enhanced ethylene-response phenotypes in rice."	( Identification of rice ethylene-response mutants and characterization of MHZ7/OsEIN2 in distinct ethylene response and yield trait regulation. Chen, H; Chen, HW; Chen, SY; Duan, KX; He, SJ; Lu, TG; Lu, X; Ma, B; Song, QX; Xiong, Q; Yang, C; Yin, CC; Zhang, JS; Zhang, WK, 2013)	1.16
"Ethylene treatments, alleviating NCPP, increased polyuronide solubility in the albedo and had a slight effect on the flavedo."	( Cell wall modifications and ethylene-induced tolerance to non-chilling peel pitting in citrus fruit. Goulas, V; Lafuente, MT; Manganaris, GA; Minas, IS; Vicente, AR, 2013)	1.41
"Ethylene treatment at or beyond 12h (threshold time) decreased the mRNA levels of the receptor genes (DcETR1, DcERS1, and DcERS2) and DcCTR genes, and increased the ethylene biosynthesis genes DcACS1 and DcACO1."	( Analysis of gene expression during the transition to climacteric phase in carnation flowers (Dianthus caryophyllus L.). Binder, BM; Falbel, TG; In, BC; Patterson, SE, 2013)	1.11
"Ethylene treatment provoked ROS generation in embryonic axis whereas ABA had no effect on their production."	( Reactive oxygen species, abscisic acid and ethylene interact to regulate sunflower seed germination. Bailly, C; Balzergue, S; Baudouin, E; Bazin, J; Cristescu, SM; El-Maarouf-Bouteau, H; Langlade, N; Sajjad, Y, 2015)	1.4
"Ethylene treatment failed to reverse the non-ripening phenotype and the expression of ethylene signaling and biosynthesis genes was strongly altered in SlARF2 down-regulated fruits."	( Auxin Response Factor SlARF2 Is an Essential Component of the Regulatory Mechanism Controlling Fruit Ripening in Tomato. Aharoni, A; Bouzayen, M; Breitel, D; Frasse, P; Fu, Y; Hao, Y; Hu, G; Liu, M; Mila, I; Zouine, M, 2015)	1.14
"Ethylene-treated fruits showed early and remarkable increase in the β-d-galactosidase transcripts while α-d-mannosidase transcript variants displayed early accumulation."	( Effect of postharvest ethylene treatment on sugar content, glycosidase activity and its gene expression in mango fruit. Chidley, HG; Deshpande, AB; Giri, AP; Gupta, VS; Oak, PS; Pujari, KH, 2017)	1.49
"Ethylene treatment cannot bypass the TIBA block of root formation."	( Hormonal control of root development on epiphyllous plantlets of Bryophyllum (Kalanchoe) marnierianum: role of auxin and ethylene. Kulka, RG, 2008)	1.28
"Ethylene treatment markedly affects GA(3) content; however, GA(3) did not significantly affect ethylene-related gene expression in regards to regulation of hypocotyl and root length, which suggests that ethylene acts upstream via gibberellin to regulate hypocotyls and root development."	( Reduced expression of CTR1 gene modulated by mitochondria causes enhanced ethylene response in cytoplasmic male-sterile Brassica juncea. Liu, X; Yang, J; Yang, X; Zhang, M; Zhao, X, 2012)	1.33
"Ethylene-treated fruits showed a comparable increase in LTB to that corresponding to 2-3 weeks of DS."	( The effects of fruit maturation, delayed storage and ethylene treatment on the incidence of low-temperature breakdown of 'Hayward' kiwifruit. Gerasopoulos, D; Koutsoflini, A; Vasilakakis, M, 2013)	1.36
"Ethylene treatment caused an increase of H2 S production and of AtD-/L-CDes activity in Arabidopsis leaves."	( Hydrogen sulfide regulates ethylene-induced stomatal closure in Arabidopsis thaliana. Hou, L; Hou, Z; Liu, J; Liu, X; Wang, L, 2013)	1.41
"Ethylene inhibitor treatment in pollinated flowers delayed the induction of PhATG8 homologues, and ethylene treatment rapidly upregulated PhATG8 homologues in petunia petals."	( Pollination induces autophagy in petunia petals via ethylene. Ichimura, K; Niki, T; Shibuya, K, 2013)	1.36
"Ethylene pretreatment induced expression of several pathogenesis-related protein genes before B."	( The role of ethylene and wound signaling in resistance of tomato to Botrytis cinerea. Díaz, J; ten Have, A; van Kan, JA, 2002)	1.41
"Ethylene treatment did not affect PAO activity, thus excluding an effect of auxin via increased ethylene biosynthesis."	( Polyamine oxidase, a hydrogen peroxide-producing enzyme, is up-regulated by light and down-regulated by auxin in the outer tissues of the maize mesocotyl. Angelini, R; Cenci, F; Cervelli, M; Cona, A; Federico, R; Mariottini, P; Moreno, S, 2003)	1.04
"Ethylene treatment induces RTE1 expression, and overexpression of RTE1 confers reduced ethylene sensitivity that partially depends on ETR1."	( REVERSION-TO-ETHYLENE SENSITIVITY1, a conserved gene that regulates ethylene receptor function in Arabidopsis. Chang, C; Resnick, JS; Shockey, JA; Wen, CK, 2006)	1.42
"When ethylene treatment was interrupted, the degree of softening was greatly reduced."	( Ethylene-regulation of fruit softening and softening-related genes in peach. Fujii, H; Hayama, H; Ito, A; Kashimura, Y; Shimada, T, 2006)	2.23
"The ethylene treatments against P. "	( Crop losses due to olive moth mediated by ethylene. Garrido, D; Ramos, JM; Ramos, P; Rosales, R; Sabouni, I, 2008)	1.17
"Ethylene treatment induces the expression of plant class I chitinases. "	( Class I chitinases, the panallergens responsible for the latex-fruit syndrome, are induced by ethylene treatment and inactivated by heating. Aragoncillo, C; Blanco, C; Carrillo, T; Collada, C; Perales, AD; Salcedo, G; Sánchez-Monge, R, 2000)	1.97
"Ethylene treatment of upright shoots inhibited elongation in 1.5 hours."	( Timing of growth inhibition following shoot inversion in Pharbitis nil. Abdel-Rahman, AM; Cline, MG, 1989)	0.9
"Treatment with ethylene resulted in 14,448 down-regulated and 6,303 up-regulated unigenes (absolute log"	( Proteomes and Ubiquitylomes Analysis Reveals the Involvement of Ubiquitination in Protein Degradation in Petunias. Chen, G; Guo, J; Liu, J; Ma, Y; Wang, R; Wei, Q; Yang, W; Yu, Y, 2017)	0.79
"Treatment with ethylene advanced the time to visible petal senescence, and hastened the changes in expression of each of the genes studied."	( Homologs of genes associated with programmed cell death in animal cells are differentially expressed during senescence of Ipomoea nil petals. Ichimura, K; Kanekatsu, M; van Doorn, WG; Yamada, T, 2009)	0.69
"When treated with ethylene, MaArf expression in banana fruit significantly increased in accordance with ethylene biosynthesis; the peak of MaArf was 3 d after harvest, 11 d earlier than for naturally ripened banana fruits."	( Cloning of an ADP-ribosylation factor gene from banana (Musa acuminata) and its expression patterns in postharvest ripening fruit. Jia, CH; Jin, ZQ; Liu, JH; Wang, Y; Wu, J; Xu, BY; Zhang, JB, 2010)	0.68
"Treatment with ethylene biosynthetic inhibitors, amino-oxyacetic acid and amino-ethoxyvinyl glycine, suppressed lethal symptoms and apoptotic changes, and also prolonged survival of hybrid seedlings."	( Overproduced ethylene causes programmed cell death leading to temperature-sensitive lethality in hybrid seedlings from the cross Nicotiana suaveolens x N. tabacum. Marubashi, W; Yamada, T, 2003)	1.03
"Treatment with ethylene gas resulted in the formation of submerged-type leaves on terrestrial shoots of L."	( Effects of ethylene and abscisic acid upon heterophylly in Ludwigia arcuata (Onagraceae). Ikegami, K; Koshiba, T; Kuwabara, A; Nagata, T, 2003)	1.05
"Treatment with ethylene counteracted the effect of NopL on chitinase (class I)."	( NopL, an effector protein of Rhizobium sp. NGR234, thwarts activation of plant defense reactions. Bartsev, AV; Boukli, NM; Broughton, WJ; Deakin, WJ; Malnoë, P; McAlvin, CB; Stacey, G; Staehelin, C, 2004)	0.66
"Treatment of ethylene or the ethylene precursor, 1-aminocyclopropane-1-carboxylic acid, resulted in increasing shikonin derivatives contents in cultured shoots."	( Ethylene induced shikonin biosynthesis in shoot culture of Lithospermum erythrorhizon. Ohashi, Y; Shimomura, K; Tamaoka, J; Touno, K, 2005)	2.12
"Treatment with ethylene precursors, like ACC (1-aminocyclopropane-1-carboxylic acid) or Ethephon (2-chloroethylphosphonic acid), resulted in increased CsHA1, CsFRO1 and CsIRT1 transcript levels and increased ferric reductase activity during early stages of Fe deficiency."	( Ethylene involvement in the regulation of the H(+)-ATPase CsHA1 gene and of the new isolated ferric reductase CsFRO1 and iron transporter CsIRT1 genes in cucumber plants. Alcántara, E; Jester, GG; Lucena, C; Pérez-Vicente, R; Rojas, CL; Romera, FJ; Waters, BM; Wynn, AN, 2007)	2.12
"Treatment with ethylene accelerated the abscission of branches of Azolla filiculoides plants. "	( Abscission of Azolla branches induced by ethylene and sodium azide. Nakamura, S; Uheda, E, 2000)	0.93
"Treatment with ethylene causes an increase in the steady-state level of this mRNA."	( Cellulase and polygalacturonase involvement in the abscission of leaf and fruit explants of peach. Bonghi, C; Casadoro, G; Ramina, A; Rascio, N, 1992)	0.62

Excerpt	Reference	Relevance
"Aerobic, co-metabolic bioremediation of trichloroethylene (TCE), cis-1,2-dichloroethylene (cis-DCE) and other chlorinated ethenes with monooxygenase-expressing microorganisms is limited by the toxic epoxides produced as intermediates."	( Metabolic pathway engineering to enhance aerobic degradation of chlorinated ethenes and to reduce their toxicity by cloning a novel glutathione S-transferase, an evolved toluene o-monooxygenase, and gamma-glutamylcysteine synthetase. Kwon, YM; Reardon, KF; Rui, L; Wood, TK, 2004)	0.58
" The aim of this study was to assess toxic potential of ethylene combustion condensates, containing both particulate and gaseous combustion by-products, by means of a recombinant bacterial assay called the SWITCH (Salmonella Weighting of Induced Toxicity (Genotoxicity) and Cytotoxicity for Human Health) test."	( Toxicity of ethylene combustion condensates is directly proportional to their carbon content. Baumstark-Khan, C; Grotheer, HH; Hellweg, CE; Hemmersbach, R; Kolanus, W; Reitz, G; Stojicic, N, 2010)	0.99
" Results suggested that: 1) The ethylene treatment caused sub-lethal stress since it induced stress-related responses and reduced peel damage; 2) 1-MCP induced ethylene-dependent and ethylene-independent responsive networks; 3) 1-MCP triggered ethylene overproduction, stress-related responses and metabolic shifts aimed to cope with cell toxicity, which mostly affected to the inner part of the peel (albedo); 4) 1-MCP increased respiration and drove metabolism reconfiguration for favoring energy conservation but up-regulated genes related to lipid and protein degradation and triggered the over-expression of genes associated with the plasma membrane cellular component; 5) Xenobiotics and/or reactive oxygen species (ROS) might act as signals for defense responses in the ethylene-treated fruit, while their uncontrolled generation would induce processes mimicking cell death and damage in 1-MCP-treated fruit; 6) ROS, the ethylene co-product cyanide and NO may converge in the toxic effects of 1-MCP."	( Inhibiting ethylene perception with 1-methylcyclopropene triggers molecular responses aimed to cope with cell toxicity and increased respiration in citrus fruits. Ballester, AR; Establés-Ortiz, B; González-Candelas, L; Lafuente, MT; Romero, P, 2016)	1.11
" The objective is to facilitate increasing insights into complex responses of plants to adverse factors common on acid soils, which can spur development of 'smart' cultivars with better root growth and higher yield on these globally distributed marginal soils."	( Phytohormone regulation of root growth triggered by P deficiency or Al toxicity. Liao, H; Sun, L; Tian, J; Zhang, H, 2016)	0.43
" This production of ethylene and auxin seems to be a component of a plant-response to toxic Al, resulting in cell wall modification or regulation of organic acid release."	( Role of phytohormones in aluminium rhizotoxicity. Kopittke, PM, 2016)	0.76
" subtilis was classified as a non-human pathogenic strain, reassuring the safe application of this plant growth-promoting bacterium as a crop inoculum."	( Effect of microorganisms on reducing cadmium uptake and toxicity in rice (Oryza sativa L.). Dhurakit, P; Khaksar, G; Thiravetyan, P; Treesubsuntorn, C, 2018)	0.48
"Aluminium (Al) is one of the most abundant metals in earth crust, which becomes toxic to the plants growing in acidic soil."	( Phytohormone signalling and cross-talk to alleviate aluminium toxicity in plants. Bishi, SK; Lal, SK; Ranjan, A; Singh, AK; Sinha, R, 2021)	0.62

Excerpt	Reference	Relevance
" By analyzing published data on ethylene oxide in man its half-life was estimated to be 42 min."	( Pharmacokinetics of ethylene in man; body burden with ethylene oxide and hydroxyethylation of hemoglobin due to endogenous and environmental ethylene. Denk, B; Ehrenberg, L; Filser, JG; Kessler, W; Törnqvist, M, 1992)	0.89
" Concentration-time data are analyzed using a two-compartment and a physiologically based pharmacokinetic (PBPK) model."	( Pharmacokinetics of ethylene in man by on-line laser photoacoustic detection. Berkelmans, HW; Bominaar, J; Harren, FJ; Moeskops, BW; Scheepers, PT, 2003)	0.64

Excerpt	Reference	Relevance
" The five members of the ethylene receptor family can physically interact and form complexes, which implies that cooperativity for signaling may exist among the receptors."	( Arabidopsis ETR1 and ERS1 differentially repress the ethylene response in combination with other ethylene receptor genes. Liu, Q; Wen, CK, 2012)	0.93
"A transition-density-fragment interaction (TDFI) combined with a transfer integral (TI) method is proposed."	( Transition-density-fragment interaction combined with transfer integral approach for excitation-energy transfer via charge-transfer states. Fujimoto, KJ, 2012)	0.38

Excerpt	Reference	Relevance
" It describes uptake of ET and EO following inhalation and intraperitoneal administration, endogenous production of ET, enzyme-mediated oxidation of ET to EO, bioavailability of EO, EO metabolism, and formation of 2-hydroxyethyl adducts of hemoglobin and DNA."	( A physiological toxicokinetic model for exogenous and endogenous ethylene and ethylene oxide in rat, mouse, and human: formation of 2-hydroxyethyl adducts with hemoglobin and DNA. Baur, C; Csanády, GA; Denk, B; Filser, JG; Gargas, ML; Kessler, W; Kreuzer, PE; Pütz, C, 2000)	0.54
"Low bioavailability of phosphorus (P) and iron (Fe) induces morphogenetic changes in roots that lead to a higher surface-to-volume ratio."	( Different pathways are involved in phosphate and iron stress-induced alterations of root epidermal cell development. Schikora, A; Schmidt, W, 2001)	0.31
"It is well documented that the bioavailability of hydrophobic organic chemicals (HOCs) can vary substantially among sediments."	( Characterization of polycyclic aromatic hydrocarbon bioavailability in estuarine sediments using thin-film extraction. Birch, GE; Gobas, FA; Golding, CJ, 2007)	0.34

Excerpt	Relevance	Reference
" In addition, we have measured gene expression as a function of ethylene concentration and have found that each gene displays a unique ethylene dose-response curve."	( Diverse mechanisms for the regulation of ethylene-inducible gene expression. Fischer, RL; Lincoln, JE, 1988)	0.78
" To the extent that the linearity hypothesis for dose-response relationships at low levels is accepted, exposure to ethene is therefore expected to lead to a risk increment."	( Is ambient ethene a cancer risk factor? Törnqvist, M, 1994)	0.29
" When combined with a NH3 dosage on a daily basis, a gradual increase of the volumetric removal rate of ethene could be observed."	( Enhancement of ethene removal from waste gas by stimulating nitrification. de heyder, B; van Elst, T; van Langenhove, H; Verstraete, W, 1997)	0.3
" Increased dosage of wild-type alleles in triploid lines led to the partial recovery of ethylene sensitivity, indicating that dominant ethylene insensitivity may involve either interactions between wild-type and mutant receptors or competition between mutant and wild-type receptors for downstream effectors."	( The relationship between ethylene binding and dominant insensitivity conferred by mutant forms of the ETR1 ethylene receptor. Bleecker, AB; Chen, QG; Findell, JL; Hall, AE; Schaller, GE, 1999)	0.83
" The time-course and dose-response of ABA accumulation closely correlated with reductions in stomatal aperture and CO(2) assimilation and increased levels of hydrogen peroxide (H(2)O(2)), deoxyribonuclease (DNase) activity and chlorophyll loss."	( Auxin herbicides induce H(2)O(2) overproduction and tissue damage in cleavers (Galium aparine L.). Grossmann, K; Kwiatkowski, J; Tresch, S, 2001)	0.31
" Dose-response analyses show efficient 1G4 staining of ART-expressing cells at micromolar etheno-NAD concentrations."	( Flow cytometric and immunoblot assays for cell surface ADP-ribosylation using a monoclonal antibody specific for ethenoadenosine. Haag, F; Koch-Nolte, F; Koestner, W; Krebs, C; Leiter, EH; Malavasi, F; Nissen, M; Parusel, I; Santella, RM; Welge, V, 2003)	0.32
" Commercial pyrazine standards were purchased, assayed for purity, and tested in dose-response studies on hamster oviducts."	( Pyrazine derivatives in cigarette smoke inhibit hamster oviductal functioning. Arey, J; Riveles, K; Roza, R; Talbot, P, 2004)	0.32
" Our model allows the effect of different ethylene concentrations in eliciting contrasting genetic and phenotypic responses to be evaluated allows the effect of different ethylene concentrations in eliciting contrasting genetic and phenotypic responses to be evaluated and seems to consider key components of the ethylene pathway because the ERF1 dose-response curve that we predict has the same qualitative form as the phenotypic dose-response curves obtained experimentally."	( A model of the ethylene signaling pathway and its gene response in Arabidopsis thaliana: pathway cross-talk and noise-filtering properties. Alvarez-Buylla, ER; Díaz, J, 2006)	0.95
" At the highest dosage of ethephon, an ethylene-releasing agent, wild-type plants formed rosettes with an inability to flower and became dormant, but one transgenic line did not."	( Involvement of the ethylene response pathway in dormancy induction in chrysanthemum. Hisamatsu, T; Narumi, T; Satoh, S; Sumitomo, K, 2008)	0.94
" Our synthetic ethylene gave the same dose-response curve in Arabidopsis as gaseous ethylene."	( Preparation of ethylene gas and comparison of ethylene responses induced by ethylene, ACC, and ethephon. Wen, CK; Zhang, W, 2010)	1.07
" Modelling further reveals that a bell-shaped dose-response relationship between endogenous auxin and root length is established via PLS."	( Modelling and experimental analysis of hormonal crosstalk in Arabidopsis. Lindsey, K; Liu, J; Mehdi, S; Tarkowski, P; Topping, J, 2010)	0.36
"The limited data available suggest that fomepizole, using the same dosage regimen as that used for adults, is efficacious and well tolerated in pediatric patients."	( Fomepizole for the treatment of pediatric ethylene and diethylene glycol, butoxyethanol, and methanol poisonings. Brent, J, 2010)	0.62
" The promising catalytic results obtained with this catalytically modified membrane reactor are attributed to the combination of 1) the high activity, as a result of the high temperature and oxygen species diffusing through the membrane; 2) the control of oxygen dosing and the low concentration of molecules in the gas phase; and 3) suitable fluid dynamics, which enables appropriate feed contact with the membrane and the rapid removal of products."	( Ethylene production by ODHE in catalytically modified Ba(0.5)Sr(0.5)Co(0.8)Fe(0.2)O(3-δ) membrane reactors. Escolástico, S; Garcia-Fayos, J; Lobera, MP; Serra, JM, 2012)	1.82
" Kinetic and dose-response analyses support a model in which two opposing factors control levels of the ethylene receptor/CTR1 complexes."	( Ethylene Regulates Levels of Ethylene Receptor/CTR1 Signaling Complexes in Arabidopsis thaliana. Amir, M; Chen, YF; Gao, Z; Haq, NU; Rai, MI; Schaller, GE; Shakeel, SN, 2015)	2.07
" Solid dosage forms for longer term implantation require to be constructed from materials that will not degrade or erode over time and also offer the utmost biocompatibility and biostability."	( The Production of Solid Dosage Forms from Non-Degradable Polymers. Fuenmayor, E; Major, I; McConville, C, 2016)	0.43
" Ni(II) ions initial concentration, pH, contact time and adsorbent dosage were optimized by response surface methodology (RSM) approach."	( Nickel adsorption onto polyurethane ethylene and vinyl acetate sorbents. Abbas, M; Ali, A; Ali, Z; Hussain, F; Iqbal, M; Nisar, J; Qamar, MA, 2017)	0.73
" Thus, this study aims to establish Thap Maeo fruit's physical, biochemical, and physiological aspects, defining the best ethylene dosage for treatment considering fruit ripening parameters."	( Thap Maeo bananas: Fast ripening and full ethylene perception at low doses. Castelan, FP; Cordenunsi-Lysenko, BR; Gomes, BL; Purgatto, E; Saraiva, LA, 2018)	0.95
" Further investigations based on controlled metal dosing reveal that the trace metals commonly present in cast iron or recycled metal scraps, such as Cu and Ni, can act as adventitious catalysts for cis-DCE reduction."	( Reactions of chlorinated ethenes with surface-sulfidated iron materials: reactivity enhancement and inhibition effects. Han, Y; Islam, S; Yan, W, 2020)	0.56
" The distinctive phenotypes of single and double mutants for four etr mutations have demonstrated that the final level of ethylene insensitivity depends upon the strength and dosage of mutant alleles for at least three cooperating ETR genes, and that the level of ethylene insensitivity determines the final sex phenotype of the plant."	( Two androecious mutations reveal the crucial role of ethylene receptors in the initiation of female flower development in Cucurbita pepo. Aguado, E; García, A; Garrido, D; Jamilena, M; Martínez, C, 2020)	1.02

Role	Description
plant hormone	A plant growth regulator that modulates the formation of stems, leaves and flowers, as well as the development and ripening of fruit. The term includes endogenous and non-endogenous compounds (e.g. active compounds produced by bacteria on the leaf surface) as well as semi-synthetic and fully synthetic compounds.
refrigerant	A substance used in a thermodynamic heat pump cycle or refrigeration cycle that undergoes a phase change from a gas to a liquid and back. Refrigerants are used in air-conditioning systems and freezers or refrigerators and are assigned a "R" number (by ASHRAE - formerly the American Society of Heating, Refrigerating and Air Conditioning Engineers), which is determined systematically according to their molecular structure.
[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
alkene	An acyclic branched or unbranched hydrocarbon having one carbon-carbon double bond and the general formula CnH2n. Acyclic branched or unbranched hydrocarbons having more than one double bond are alkadienes, alkatrienes, etc.
gas molecular entity	Any main group molecular entity that is gaseous at standard temperature and pressure (STP; 0degreeC and 100 kPa).
[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
Metabolism	1496	1108
Biological oxidations	150	276
Phase I - Functionalization of compounds	69	175
Cytochrome P450 - arranged by substrate type	30	110
Xenobiotics	4	50
ethene biosynthesis I (plants)	0	15
ethylene biosynthesis II (microbes)	0	15
6-methoxymellein biosynthesis	0	22
ethylene biosynthesis I (plants)	4	15
terminal olefins biosynthesis I	0	6
tetrachloroethene degradation	1	13
ethylene biosynthesis IV (engineered)	2	18
leucopelargonidin and leucocyanidin biosynthesis	7	20
ethene and chloroethene degradation	5	21
ethylene biosynthesis II (microbes)	1	19
ethylene biosynthesis III (microbes)	0	15
ethylene biosynthesis V (engineered)	78	42
ethylene biosynthesis I (plants)	8	15
ethylene biosynthesis	8	15
Ethylene signaling pathway	0	3
Genetic interactions between sugar and hormone signaling	0	5
Ethylene biosynthesis and signaling	11	16
Ethene biosynthesis from methionine	1	14
Ethylene mediated signaling	10	4

Assay ID	Title	Year	Journal	Article
AID1100823	Induction of disease resistance in Oryza sativa Nipponbare (rice) assessed as increase in momilactone level in press-injured leaves at 5 to 25% after 48 hr by HPLC-MS-MS analysis	2000	Bioscience, biotechnology, and biochemistry, Mar, Volume: 64, Issue:3	Methionine-induced phytoalexin production in rice leaves.
AID603952	In-vitro blood to lung partition coefficients of the compound, logP(lung) (human/rat)	2008	European journal of medicinal chemistry, Mar, Volume: 43, Issue:3	Air to lung partition coefficients for volatile organic compounds and blood to lung partition coefficients for volatile organic compounds and drugs.
AID603950	In-vitro air to lung partition coefficients of the compound, logK(lung) (human/rat)	2008	European journal of medicinal chemistry, Mar, Volume: 43, Issue:3	Air to lung partition coefficients for volatile organic compounds and blood to lung partition coefficients for volatile organic compounds and drugs.
AID603951	In-vitro air to blood partition coefficients of the compound, logK(blood) (human/rat)	2008	European journal of medicinal chemistry, Mar, Volume: 43, Issue:3	Air to lung partition coefficients for volatile organic compounds and blood to lung partition coefficients for volatile organic compounds and drugs.
AID1100825	Induction of disease resistance in three-leaf (rice) assessed as increase in sakuranetin level in press-injured leaves at 5 to 25% after 48 hr by HPLC-MS-MS analysis	2000	Bioscience, biotechnology, and biochemistry, Mar, Volume: 64, Issue:3	Methionine-induced phytoalexin production in rice leaves.
AID23443	Partition coefficient (logP)	1985	Journal of medicinal chemistry, Mar, Volume: 28, Issue:3	Use of physicochemical parameters in distance geometry and related three-dimensional quantitative structure-activity relationships: a demonstration using Escherichia coli dihydrofolate reductase inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	366 (6.38)	18.7374
1990's	577 (10.06)	18.2507
2000's	1711 (29.84)	29.6817
2010's	2513 (43.83)	24.3611
2020's	566 (9.87)	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	22 (0.38%)	5.53%
Reviews	396 (6.76%)	6.00%
Case Studies	58 (0.99%)	4.05%
Observational	1 (0.02%)	0.25%
Other	5,379 (91.85%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Trial	Phase	Enrollment	Study Type	Start Date	Status
Randomized Comparison to Freeze Human Embryos by Either Vitrification or Slow Freezing Protocols [NCT00910390]		584 participants (Actual)	Interventional	2009-04-30	Completed
The Effect of Dynamic Impression Insoles on Plantar Pressure and Pain in Persons With Metatarsal Pain [NCT01629173]	Early Phase 1	50 participants (Actual)	Interventional	2011-04-30	Completed
Feasibility of Prostatic Arterial Embolization With SQUID (Ethylene Vinyl Alcohol Copolymer ) in Symptomatic Patients With Benign Prostatic Hyperplasia: Monocentric Pilot Study [NCT05395299]		10 participants (Anticipated)	Interventional	2022-06-01	Not yet recruiting
Early eNdovascular Embolization for Chronic subduraL hematOma After SUrgery and Prevention of REcurrence (ENCLOSURE) [NCT05220826]		280 participants (Anticipated)	Interventional	2022-02-11	Recruiting
A Phase I Pilot Study of Samarium-153 Combined With Neoadjuvant Hormonal Therapy and Radiation Therapy in Men With Locally Advanced Prostate Cancer [NCT00328614]	Phase 1	32 participants (Actual)	Interventional	2003-03-31	Completed
A Randomized, 4-Sequence, Double-Blind Study to Test the Safety of Combined Dosing With Aminophylline and Ambrisentan in Exercising Healthy Human Volunteers at Simulated High Altitude [NCT01794078]	Phase 1	92 participants (Actual)	Interventional	2013-09-30	Completed
Comparing the Dentin Conditioning Effect of Different Single and Combination Chelating Agents on Sealer Penetration and Dentin Erosion [NCT05778227]		100 participants (Actual)	Interventional	2021-11-16	Completed
Ethanolic Extract of Sapindus Mukorossi as the Final Endodontic Irrigant. [NCT05038059]		90 participants (Actual)	Interventional	2020-04-02	Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Trial	Outcome
NCT00328614 (1) [back to overview]	Maximum Tolerated Dose of Samarium-153

Intervention	mCi/kg (Number)
Samarium-153	2.0

Substance	Relationship Strength	Studies	Trials	Classes	Roles
monoisopropanolamine monoisopropanolamine: possible industrial pollutant; structure. 1-aminopropan-2-ol : Any amino alcohol that is propan-2-ol substituted by an amino group at position 1.	1.96	1	0	amino alcohol; secondary alcohol	Escherichia coli metabolite
ethylene dichloride ethylene dichloride: RN given refers to 1,2-isomer; structure given in first source. 1,2-dichloroethane : A member of the class of chloroethanes substituted by two chloro groups at positions 1 and 2.	4	14	0	chloroethanes	hepatotoxic agent; mutagen; non-polar solvent
1,2,4-trichlorobenzene 1,2,4-trichlorobenzene : A trichlorobenzene with chloro substituents at positions 1, 2 and 4.	2.15	1	0	trichlorobenzene
ethylene chlorohydrin Ethylene Chlorohydrin: Used as a solvent, in the manufacture of insecticides, and for treating sweet potatoes before planting. May cause nausea, vomiting, pains in head and chest, stupefaction. Irritates mucous membranes and causes kidney and liver degeneration.. chloroethanol : An organochlorine compound that is ethanol substituted by at least one chloro group.	1.92	1	0	chloroethanol	xenobiotic metabolite
phosphoserine Phosphoserine: The phosphoric acid ester of serine.	2.07	1	0	non-proteinogenic alpha-amino acid; O-phosphoamino acid; serine derivative	human metabolite
gamma-aminobutyric acid gamma-Aminobutyric Acid: The most common inhibitory neurotransmitter in the central nervous system.. gamma-aminobutyric acid : A gamma-amino acid that is butanoic acid with the amino substituent located at C-4.	8.86	11	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
aminolevulinic acid Aminolevulinic Acid: A compound produced from succinyl-CoA and GLYCINE as an intermediate in heme synthesis. It is used as a PHOTOCHEMOTHERAPY for actinic KERATOSIS.. 5-aminolevulinic acid : The simplest delta-amino acid in which the hydrogens at the gamma position are replaced by an oxo group. It is metabolised to protoporphyrin IX, a photoactive compound which accumulates in the skin. Used (in the form of the hydrochloride salt)in combination with blue light illumination for the treatment of minimally to moderately thick actinic keratosis of the face or scalp.	3.53	2	0	4-oxo monocarboxylic acid; amino acid zwitterion; delta-amino acid	antineoplastic agent; dermatologic drug; Escherichia coli metabolite; human metabolite; mouse metabolite; photosensitizing agent; plant metabolite; prodrug; Saccharomyces cerevisiae metabolite
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.	8.46	2	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.	8.49	8	0	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
acetaldehyde Acetaldehyde: A colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis.. acetaldehyde : The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.. aldehyde : A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.. acetyl group : A group, formally derived from acetic acid by dehydroxylation, which is fundamental to the biochemistry of all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.	8.76	10	0	aldehyde	carcinogenic agent; EC 3.5.1.4 (amidase) inhibitor; electron acceptor; Escherichia coli metabolite; human metabolite; mouse metabolite; mutagen; oxidising agent; Saccharomyces cerevisiae metabolite; teratogenic agent
acetamide acetimidic acid : A carboximidic acid that is acetic acid in which the carbonyl oxygen is replaced by an imino group.	2.03	1	0	acetamides; carboximidic acid; monocarboxylic acid amide; N-acylammonia
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	3.8	11	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]	7.14	16	1	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
adipic acid adipic acid : An alpha,omega-dicarboxylic acid that is the 1,4-dicarboxy derivative of butane.	2.6	1	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	food acidity regulator; human xenobiotic metabolite
agmatine Agmatine: Decarboxylated arginine, isolated from several plant and animal sources, e.g., pollen, ergot, herring sperm, octopus muscle.	2.61	2	0	guanidines; primary amino compound	Escherichia coli metabolite; mouse metabolite
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	7.48	23	1	azane; gas molecular entity; mononuclear parent hydride	EC 3.5.1.4 (amidase) inhibitor; metabolite; mouse metabolite; neurotoxin; NMR chemical shift reference compound; nucleophilic reagent; refrigerant
anthranilic acid anthranilic acid: RN given refers to parent cpd; structure in Negwer, 5th ed, #565. anthranilic acid : An aminobenzoic acid that is benzoic acid having a single amino substituent located at position 2. It is a metabolite produced in L-tryptophan-kynurenine pathway in the central nervous system.	2.06	1	0	aminobenzoic acid	human metabolite; mouse metabolite
arsenic acid arsenic acid: RN given refers to orthoarsenic acid(H3AsO4); see also sodium arsenate. arsenic acid : An arsenic oxoacid comprising one oxo group and three hydroxy groups attached to a central arsenic atom.	2.81	3	0	arsenic oxoacid	Escherichia coli metabolite
benzaldehyde [no description available]	7.8	3	0	benzaldehydes	EC 3.1.1.3 (triacylglycerol lipase) inhibitor; EC 3.5.5.1 (nitrilase) inhibitor; flavouring agent; fragrance; odorant receptor agonist; plant metabolite
benzene [no description available]	6.32	28	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.	8.01	4	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.	2.08	1	0	benzyl alcohols	antioxidant; fragrance; metabolite; solvent
betaine glycine betaine : The amino acid betaine derived from glycine.	8.61	2	0	amino-acid betaine; glycine derivative	fundamental metabolite
bromide Bromides: Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	7.34	2	0	halide anion; monoatomic bromine
butyraldehyde [no description available]	2.04	1	0	butanals	biomarker; Escherichia coli metabolite; mouse metabolite
1-butanol 1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.	3.09	5	0	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
butyric acid Butyric Acid: A four carbon acid, CH3CH2CH2COOH, with an unpleasant odor that occurs in butter and animal fat as the glycerol ester.. butyrate : A short-chain fatty acid anion that is the conjugate base of butyric acid, obtained by deprotonation of the carboxy group.. butyric acid : A straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group.	2.05	1	0	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
cadaverine [no description available]	2.5	2	0	alkane-alpha,omega-diamine	Daphnia magna metabolite; Escherichia coli metabolite; mouse metabolite; plant metabolite
carbamates [no description available]	2.04	1	0	amino-acid anion
carbon monoxide Carbon Monoxide: Carbon monoxide (CO). A poisonous colorless, odorless, tasteless gas. It combines with hemoglobin to form carboxyhemoglobin, which has no oxygen carrying capacity. The resultant oxygen deprivation causes headache, dizziness, decreased pulse and respiratory rates, unconsciousness, and death. (From Merck Index, 11th ed). carbon monoxide : A one-carbon compound in which the carbon is joined only to a single oxygen. It is a colourless, odourless, tasteless, toxic gas.	7.32	43	0	carbon oxide; gas molecular entity; one-carbon compound	biomarker; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; human metabolite; ligand; metabolite; mitochondrial respiratory-chain inhibitor; mouse metabolite; neurotoxin; neurotransmitter; P450 inhibitor; probe; signalling molecule; vasodilator agent
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.	3.67	9	0	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
aminooxyacetic acid Aminooxyacetic Acid: A compound that inhibits aminobutyrate aminotransferase activity in vivo, thereby raising the level of gamma-aminobutyric acid in tissues.. (aminooxy)acetic acid : A member of the class of hydroxylamines that is acetic acid substituted at postion 2 by an aminooxy group. It is a compound which inhibits aminobutyrate aminotransferase activity in vivo, resulting in increased levels of gamma-aminobutyric acid in tissues.	4.21	17	0	amino acid; hydroxylamines; monocarboxylic acid	anticonvulsant; EC 2.6.1.19 (4-aminobutyrate--2-oxoglutarate transaminase) inhibitor; EC 4.2.1.22 (cystathionine beta-synthase) inhibitor; nootropic agent
carnitine [no description available]	4.06	2	0	amino-acid betaine	human metabolite; mouse metabolite
catechol [no description available]	2.04	1	0	catechols	allelochemical; genotoxin; plant metabolite
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).	10.02	99	1	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
chloroacetic acid chloroacetic acid: urinary metabolite of vinyl chloride; RN given refers to parent cpd; structure. chloroacetic acid : A chlorocarboxylic acid that is acetic acid carrying a 2-chloro substituent.	2.02	1	0	chlorocarboxylic acid; haloacetic acid	alkylating agent; herbicide
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.	6.59	8	2	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.	5.64	24	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.	3.13	5	0	chlorine molecular entity; gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
coumarin 2H-chromen-2-one: coumarin derivative	7.59	2	0	coumarins	fluorescent dye; human metabolite; plant metabolite
salicylic acid Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).	11.66	416	0	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
3-cresol 3-cresol: RN given refers to parent cpd. m-cresol : A cresol with the methyl substituent at position 3. It is a minor urinary metabolite of toluene.	1.96	1	0	cresol	human xenobiotic 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.	2.01	1	0	benzenetriol; phenolic donor	algal metabolite
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	1.97	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
hydrogen sulfide Hydrogen Sulfide: A flammable, poisonous gas with a characteristic odor of rotten eggs. It is used in the manufacture of chemicals, in metallurgy, and as an analytical reagent. (From Merck Index, 11th ed). hydrogen sulfide : A sulfur hydride consisting of a single sulfur atom bonded to two hydrogen atoms. A highly poisonous, flammable gas with a characteristic odour of rotten eggs, it is often produced by bacterial decomposition of organic matter in the absence of oxygen.. thiol : An organosulfur compound in which a thiol group, -SH, is attached to a carbon atom of any aliphatic or aromatic moiety.	5.55	12	0	gas molecular entity; hydracid; mononuclear parent hydride; sulfur hydride	Escherichia coli metabolite; genotoxin; metabolite; signalling molecule; toxin; vasodilator agent
nornicotine nornicotine: agricultural or horticultural insecticide; RN given refers to (+-)-isomer; structure	2.21	1	0
hippuric acid hippuric acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #4591. N-benzoylglycine : An N-acylglycine in which the acyl group is specified as benzoyl.	1.97	1	0	N-acylglycine	human blood serum metabolite; uremic toxin
2-keto-4-methylthiobutyric acid 2-keto-4-methylthiobutyric acid: RN given refers to parent cpd; structure. 4-methylthio-2-oxobutanoic acid : A 2-oxo monocarboxylic acid derived from L-methionine via the action of methionine transaminase.	4.13	16	0	omega-(methylthio)-2-oxocarboxylic acid
malic acid malic acid : A 2-hydroxydicarboxylic acid that is succinic acid in which one of the hydrogens attached to a carbon is replaced by a hydroxy group.. 2-hydroxydicarboxylic acid : Any dicarboxylic acid carrying a hydroxy group on the carbon atom at position alpha to the carboxy group.	3.21	5	0	2-hydroxydicarboxylic acid; C4-dicarboxylic acid	food acidity regulator; fundamental metabolite
propionaldehyde propionaldehyde: may cause respiratory irritation; RN given refers to parent cpd; structure. propanal : An aldehyde that consists of ethane bearing a formyl substituent. The parent of the class of propanals.	2.45	2	0	alpha-CH2-containing aldehyde; propanals	Escherichia coli metabolite
1-aminocyclopropane-1-carboxylic acid 1-aminocyclopropanecarboxylic acid : A non-proteinogenic alpha-amino acid consisting of cyclopropane having amino and carboxy substituents both at the 1-position.	6.77	227	0	amino acid zwitterion; monocarboxylic acid; non-proteinogenic alpha-amino acid	ethylene releasers; plant metabolite
cytosine [no description available]	2.17	1	0	aminopyrimidine; pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	3.11	5	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna 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.	2.38	2	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	4.36	20	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]	5.58	69	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
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	5.93	7	1	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
alpha-glycerophosphoric acid [no description available]	2.04	1	0	glycerol monophosphate	algal metabolite; human metabolite
glyoxylic acid glyoxylic acid: RN given refers to parent cpd. glyoxylic acid : A 2-oxo monocarboxylic acid that is acetic acid bearing an oxo group at the alpha carbon atom.	2.25	1	0	2-oxo monocarboxylic acid; aldehydic acid	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae 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	10.19	15	0	hydracid; one-carbon compound	Escherichia coli metabolite; human metabolite; poison
hydrogen carbonate Bicarbonates: Inorganic salts that contain the -HCO3 radical. They are an important factor in determining the pH of the blood and the concentration of bicarbonate ions is regulated by the kidney. Levels in the blood are an index of the alkali reserve or buffering capacity.. hydrogencarbonate : The carbon oxoanion resulting from the removal of a proton from carbonic acid.	4.51	4	0	carbon oxoanion	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
histamine [no description available]	4.85	2	1	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
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.	8.77	59	1	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
hydroquinone [no description available]	2.43	2	0	benzenediol; hydroquinones	antioxidant; carcinogenic agent; cofactor; Escherichia coli metabolite; human xenobiotic metabolite; mouse metabolite; skin lightening agent
hydroxylamine amino alcohol : An alcohol containing an amino functional group in addition to the alcohol-defining hydroxy group.	2.4	2	0	hydroxylamines	algal metabolite; bacterial xenobiotic metabolite; EC 1.1.3.13 (alcohol oxidase) inhibitor; EC 4.2.1.22 (cystathionine beta-synthase) inhibitor; EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor; nitric oxide donor; nucleophilic reagent
imidazole imidazole: RN given refers to parent cpd. 1H-imidazole : An imidazole tautomer which has the migrating hydrogen at position 1.	2.69	3	0	imidazole
indole [no description available]	2.73	3	0	indole; polycyclic heteroarene	Escherichia coli metabolite
indole-3-acetaldehyde indoleacetaldehyde : An aldehyde that is acetaldehyde substituted by an indolyl group.. indol-3-ylacetaldehyde : An indoleacetaldehyde that is acetaldehyde in which one of the methyl hydrogens are replaced by a indol-3-yl group. It is an intermediate metabolite in the metabolism of tryptophan.	2.11	1	0	indoleacetaldehyde	bacterial metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
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.	8.44	110	0	indole-3-acetic acids; monocarboxylic acid	auxin; human metabolite; mouse metabolite; plant hormone; plant metabolite
indol-3-yl pyruvic acid 3-(indol-3-yl)pyruvic acid : A 2-oxo monocarboxylic acid that is pyruvic acid substituted by a 1H-indol-3-yl group at position 3. It has been found in Lycopersicon esculentum	3.48	7	0	2-oxo monocarboxylic acid; indol-3-yl carboxylic acid	plant metabolite; Saccharomyces cerevisiae 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..	2.36	2	0	diatomic iodine	nutrient
kynurenine Kynurenine: A metabolite of the essential amino acid tryptophan metabolized via the tryptophan-kynurenine pathway.. kynurenine : A ketone that is alanine in which one of the methyl hydrogens is substituted by a 2-aminobenzoyl group.	7.06	1	0	aromatic ketone; non-proteinogenic alpha-amino acid; substituted aniline	human metabolite
pipecolic acid pipecolic acid: RN given refers to cpd without isomeric designation. pipecolic acid : A piperidinemonocarboxylic acid in which the carboxy group is located at position C-2.. pipecolate : A piperidinecarboxylate that is the conjugate base of pipecolic acid.	3.66	2	0	piperidinemonocarboxylic acid
thioctic acid Thioctic Acid: An octanoic acid bridged with two sulfurs so that it is sometimes also called a pentanoic acid in some naming schemes. It is biosynthesized by cleavage of LINOLEIC ACID and is a coenzyme of oxoglutarate dehydrogenase (KETOGLUTARATE DEHYDROGENASE COMPLEX). It is used in DIETARY SUPPLEMENTS.	2.03	1	0	dithiolanes; heterocyclic fatty acid; thia fatty acid	fundamental metabolite; geroprotector
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.	2.48	2	0	alpha,omega-dicarboxylic acid	human 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.	5.54	21	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
inositol Inositol: An isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1379) Inositol phospholipids are important in signal transduction.. inositol : Any cyclohexane-1,2,3,4,5,6-hexol.. 1D-chiro-inositol : Belonging to the inositol family of compounds, D-chiro-inositol (DCI) is an isomer of glucose. It is an important secondary messenger in insulin signal transduction.. muco-inositol : An inositol that is cyclohexane-1,2,3,4,5,6-hexol having a (1R,2R,3r,4R,5S,6r)-configuration.	2.91	3	0	cyclitol; hexol
melatonin [no description available]	4.85	8	0	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
naphthalene [no description available]	3.09	5	0	naphthalenes; ortho-fused bicyclic arene	apoptosis inhibitor; carcinogenic agent; environmental contaminant; mouse metabolite; plant metabolite; volatile oil component
nickel Nickel: A trace element with the atomic symbol Ni, atomic number 28, and atomic weight 58.69. It is a cofactor of the enzyme UREASE.. nickel ion : A nickel atom having a net electric charge.. nickel atom : Chemical element (nickel group element atom) with atomic number 28.	6.34	28	0	metal allergen; nickel group element atom	epitope; micronutrient
niacinamide nicotinamide : A pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group.	2.07	1	0	pyridine alkaloid; pyridinecarboxamide; vitamin B3	anti-inflammatory agent; antioxidant; cofactor; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; Escherichia coli metabolite; geroprotector; human urinary metabolite; metabolite; mouse metabolite; neuroprotective agent; Saccharomyces cerevisiae metabolite; Sir2 inhibitor
niacin Niacin: A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has PELLAGRA-curative, vasodilating, and antilipemic properties.. vitamin B3 : Any member of a group of vitamers that belong to the chemical structural class called pyridines that exhibit biological activity against vitamin B3 deficiency. Vitamin B3 deficiency causes a condition known as pellagra whose symptoms include depression, dermatitis and diarrhea. The vitamers include nicotinic acid and nicotinamide (and their ionized and salt forms).. nicotinic acid : A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group.	6.93	1	0	pyridine alkaloid; pyridinemonocarboxylic acid; vitamin B3	antidote; antilipemic drug; EC 3.5.1.19 (nicotinamidase) inhibitor; Escherichia coli metabolite; human urinary metabolite; metabolite; mouse metabolite; plant metabolite; vasodilator agent
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	8.83	35	1	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
nitric acid Nitric Acid: Nitric acid (HNO3). A colorless liquid that is used in the manufacture of inorganic and organic nitrates and nitro compounds for fertilizers, dye intermediates, explosives, and many different organic chemicals. Continued exposure to vapor may cause chronic bronchitis; chemical pneumonitis may occur. (From Merck Index, 11th ed). nitric acid : A nitrogen oxoacid of formula HNO3 in which the nitrogen atom is bonded to a hydroxy group and by equivalent bonds to the remaining two oxygen atoms.	2.8	3	0	nitrogen oxoacid	protic solvent; reagent
nitroxyl nitroxyl: hydroxamic acid oxidized to nitroxyl free radical. nitroxyl : A nitrogen oxoacid consisting of an oxygen atom double-bonded to an NH group.	2.21	1	0	nitrogen oxoacid
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)	6.53	8	1	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
nitrous oxide Nitrous Oxide: Nitrogen oxide (N2O). A colorless, odorless gas that is used as an anesthetic and analgesic. High concentrations cause a narcotic effect and may replace oxygen, causing death by asphyxia. It is also used as a food aerosol in the preparation of whipping cream.. dinitrogen oxide : A nitrogen oxide consisting of linear unsymmetrical molecules with formula N2O. While it is the most used gaseous anaesthetic in the world, its major commercial use, due to its solubility under pressure in vegetable fats combined with its non-toxicity in low concentrations, is as an aerosol spray propellant and aerating agent for canisters of 'whipped' cream.	4.04	15	0	gas molecular entity; nitrogen oxide	analgesic; bacterial metabolite; food packaging gas; food propellant; general anaesthetic; greenhouse gas; inhalation anaesthetic; NMDA receptor antagonist; raising agent; refrigerant; vasodilator agent
hydroxide ion [no description available]	2.36	2	0	oxygen hydride	mouse metabolite
oxalic acid Oxalic Acid: A strong dicarboxylic acid occurring in many plants and vegetables. It is produced in the body by metabolism of glyoxylic acid or ascorbic acid. It is not metabolized but excreted in the urine. It is used as an analytical reagent and general reducing agent.. oxalic acid : An alpha,omega-dicarboxylic acid that is ethane substituted by carboxyl groups at positions 1 and 2.	7.98	4	0	alpha,omega-dicarboxylic acid	algal metabolite; human metabolite; plant 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.	2.17	1	0	aminobenzoic acid; aromatic amino-acid zwitterion	allergen; Escherichia coli metabolite; plant metabolite
phenanthrene phenanthrene : A polycyclic aromatic hydrocarbon composed of three fused benzene rings which takes its name from the two terms 'phenyl' and 'anthracene.'	2.77	3	0	ortho-fused polycyclic arene; ortho-fused tricyclic hydrocarbon; phenanthrenes	environmental contaminant; mouse metabolite
phenol [no description available]	3.33	6	0	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse 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.	5.16	3	1	glycol; propane-1,2-diols	allergen; human xenobiotic metabolite; mouse metabolite; protic solvent
1-propanol 1-Propanol: A colorless liquid made by oxidation of aliphatic hydrocarbons that is used as a solvent and chemical intermediate.. propan-1-ol : The parent member of the class of propan-1-ols that is propane in which a hydrogen of one of the methyl groups is replaced by a hydroxy group.	2.68	3	0	propan-1-ols; short-chain primary fatty alcohol	metabolite; protic solvent
pteridines [no description available]	2.03	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; pteridines
putrescine [no description available]	6.24	25	0	alkane-alpha,omega-diamine	antioxidant; fundamental metabolite
pyrazinamide pyrazinecarboxamide : A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of pyrazinoic acid (pyrazine-2-carboxylic acid) with ammonia. A prodrug for pyrazinoic acid, pyrazinecarboxamide is used as part of multidrug regimens for the treatment of tuberculosis.	7.58	2	0	monocarboxylic acid amide; N-acylammonia; pyrazines	antitubercular agent; prodrug
pyrazole 1H-pyrazole : The 1H-tautomer of pyrazole.	2.08	1	0	pyrazole
pyridine azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.	8.38	7	0	azaarene; mancude organic heteromonocyclic parent; monocyclic heteroarene; pyridines	environmental contaminant; NMR chemical shift reference compound
pyridoxal phosphate Pyridoxal Phosphate: This is the active form of VITAMIN B 6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (PYRIDOXAMINE).. pyridoxal 5'-phosphate : The monophosphate ester obtained by condensation of phosphoric acid with the primary hydroxy group of pyridoxal.	2.71	3	0	methylpyridines; monohydroxypyridine; pyridinecarbaldehyde; vitamin B6 phosphate	coenzyme; cofactor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
pyridoxamine [no description available]	2.01	1	0	aminoalkylpyridine; hydroxymethylpyridine; monohydroxypyridine; vitamin B6	Escherichia coli metabolite; human metabolite; iron chelator; mouse metabolite; nephroprotective agent; plant metabolite; Saccharomyces cerevisiae metabolite
pyridoxine 4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol: structure in first source. vitamin B6 : Any member of the group of pyridines that exhibit biological activity against vitamin B6 deficiency. Vitamin B6 deficiency is associated with microcytic anemia, electroencephalographic abnormalities, dermatitis with cheilosis (scaling on the lips and cracks at the corners of the mouth) and glossitis (swollen tongue), depression and confusion, and weakened immune function. Vitamin B6 consists of the vitamers pyridoxine, pyridoxal, and pyridoxamine and their respective 5'-phosphate esters (and includes their corresponding ionized and salt forms).	2.01	1	0	hydroxymethylpyridine; methylpyridines; monohydroxypyridine; vitamin B6	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
pyruvic acid Pyruvic Acid: An intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed). pyruvic acid : A 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis.	3.09	5	0	2-oxo monocarboxylic acid	cofactor; fundamental metabolite
dimethyl sulfide dimethyl sulfide: structure. dimethyl sulfide : A methyl sulfide in which the sulfur atom is substituted by two methyl groups. It is produced naturally by some marine algae.. methyl sulfide : Any aliphatic sulfide in which at least one of the organyl groups attached to the sulfur is a methyl group.	2.03	1	0	aliphatic sulfide	algal metabolite; bacterial xenobiotic metabolite; EC 3.5.1.4 (amidase) inhibitor; Escherichia coli metabolite; marine metabolite
thiosulfates Thiosulfates: Inorganic salts of thiosulfuric acid possessing the general formula R2S2O3.. thiosulfate(2-) : A divalent inorganic anion obtained by removal of both protons from thiosulfuric acid.	4.28	18	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion	human metabolite
dithionite Dithionite: Dithionite. The dithionous acid ion and its salts.	1.97	1	0	sulfur oxide; sulfur oxoanion
sarcosine cocobetaine: N-alkyl-betaine; cause of shampoo dermatitis	2.15	1	0	N-alkylglycine zwitterion; N-alkylglycine; N-methyl-amino acid; N-methylglycines	Escherichia coli metabolite; glycine receptor agonist; glycine transporter 1 inhibitor; human metabolite; mouse metabolite
selenic acid Selenic Acid: A strong dibasic acid with the molecular formula H2SeO4. Included under this heading is the acid form, and inorganic salts of dihydrogen selenium tetraoxide.	2.58	2	0	selenium oxoacid
selenious acid Selenious Acid: A selenium compound with the molecular formula H2SO3. It used as a source of SELENIUM, especially for patients that develop selenium deficiency following prolonged PARENTERAL NUTRITION.	2.52	2	0	selenium oxoacid
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).	3.35	1	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion
spermidine [no description available]	6.02	20	0	polyazaalkane; triamine	autophagy inducer; fundamental metabolite; geroprotector
spermine [no description available]	6.35	15	0	polyazaalkane; tetramine	antioxidant; fundamental metabolite; immunosuppressive agent
succinic acid Succinic Acid: A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawley's Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851). succinic acid : An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.	3.84	3	0	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
sulfuric acid sulfuric acid : A sulfur oxoacid that consists of two oxo and two hydroxy groups joined covalently to a central sulfur atom.	2.72	3	0	sulfur oxoacid	catalyst
sulfur dioxide Sulfur Dioxide: A highly toxic, colorless, nonflammable gas. It is used as a pharmaceutical aid and antioxidant. It is also an environmental air pollutant.	5.93	7	1	sulfur oxide	Escherichia coli metabolite; food bleaching agent; refrigerant
taurine [no description available]	2.04	1	0	amino sulfonic acid; zwitterion	antioxidant; Escherichia coli metabolite; glycine receptor agonist; human metabolite; mouse metabolite; nutrient; radical scavenger; Saccharomyces cerevisiae metabolite
thiamine thiamine(1+) : A primary alcohol that is 1,3-thiazol-3-ium substituted by (4-amino-2-methylpyrimidin-5-yl)methyl, methyl and 2-hydroxyethyl groups at positions 3, 4 and 5, respectively.	8.55	2	0	primary alcohol; vitamin B1	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
2-mercaptoacetate [no description available]	1.96	1	0	sulfur-containing carboxylic acid
thymine [no description available]	7.75	3	0	pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	3.92	13	0	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
trimethylamine [no description available]	2.13	1	0	methylamines; tertiary amine	Escherichia coli metabolite; human xenobiotic metabolite
tryptamine [no description available]	3.27	1	0	aminoalkylindole; aralkylamino compound; indole alkaloid; tryptamines	human metabolite; mouse metabolite; plant 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.	1.99	1	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.	9.48	7	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
xanthine 7H-xanthine : An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-7 is protonated.. 9H-xanthine : An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-9 is protonated.	2.38	2	0	xanthine	Saccharomyces cerevisiae metabolite
2,4-methanoglutamate 2,4-methanoglutamate: structure given in first source; selective N-methyl-D-aspartate receptor agonist; inhibits high affinity L-glutamic acid uptake into rat cortical synaptosomes; RN given for (trans)-isomer	2.04	1	0
1,10-phenanthroline 1,10-phenanthroline: RN given refers to parent cpd; inhibits Zn-dependent metalloproteinases	2.06	1	0	phenanthroline	EC 2.7.1.1 (hexokinase) inhibitor; EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor
1,2-dimethylhydrazine 1,2-Dimethylhydrazine: A DNA alkylating agent that has been shown to be a potent carcinogen and is widely used to induce colon tumors in experimental animals.. 1,2-dimethylhydrazine : A member of the class of hydrazines that is hydrazine in which one of the hydrogens attached to each nitrogen is replaced by a methyl group. A powerful DNA alkylating agent and carcinogen, it is used to induce colon cancer in laboratory rats and mice.	1.97	1	0	hydrazines	alkylating agent; carcinogenic agent
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.	3.33	6	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
2,4-dichlorophenoxyacetic acid 2,4-Dichlorophenoxyacetic Acid: An herbicide with irritant effects on the eye and the gastrointestinal system.. 2,4-D : A chlorophenoxyacetic acid that is phenoxyacetic acid in which the ring hydrogens at postions 2 and 4 are substituted by chlorines.	9.46	22	0	chlorophenoxyacetic acid; dichlorobenzene	agrochemical; defoliant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; environmental contaminant; phenoxy herbicide; synthetic auxin
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
amitrole Amitrole: A non-selective post-emergence, translocated herbicide. According to the Seventh Annual Report on Carcinogens (PB95-109781, 1994) this substance may reasonably be anticipated to be a carcinogen. (From Merck Index, 12th ed) It is an irreversible inhibitor of CATALASE, and thus impairs activity of peroxisomes.. amitrole : A member of the class of triazoles that is 1H-1,2,4-triazole substituted by an amino group at position 3. Used to control annual grasses and aquatic weeds (but not on food crops because it causes cancer in laboratory animals). Its use within the EU was banned from September 2017 on the grounds of potential groundwater contamination and risks to aquatic life; there have also been concerns about its endocrine-disrupting properties.	2.07	1	0	aromatic amine; triazoles	carotenoid biosynthesis inhibitor; EC 1.11.1.6 (catalase) inhibitor; herbicide
phenytoin [no description available]	2.04	1	0	imidazolidine-2,4-dione	anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent
2,2'-azobis(2-amidinopropane) 2,2'-azobis(2-amidinopropane): water-soluble free-radical initiator	2.05	1	0	monoazo compound
acebutolol Acebutolol: A cardioselective beta-1 adrenergic antagonist with little effect on the bronchial receptors. The drug has stabilizing and quinidine-like effects on cardiac rhythm, as well as weak inherent sympathomimetic action.. acebutolol : An ether that is the 2-acetyl-4-(butanoylamino)phenyl ether of the primary hydroxy group of 3-(propan-2-ylamino)propane-1,2-diol.	2.04	1	0	aromatic amide; ethanolamines; ether; monocarboxylic acid amide; propanolamine; secondary amino compound	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; sympathomimetic agent
acetaminophen Acetaminophen: Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage.. paracetamol : A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.	1.99	1	0	acetamides; phenols	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; cyclooxygenase 3 inhibitor; environmental contaminant; ferroptosis inducer; geroprotector; hepatotoxic agent; human blood serum metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
alprazolam Alprazolam: A triazolobenzodiazepine compound with antianxiety and sedative-hypnotic actions, that is efficacious in the treatment of PANIC DISORDERS, with or without AGORAPHOBIA, and in generalized ANXIETY DISORDERS. (From AMA Drug Evaluations Annual, 1994, p238). alprazolam : A member of the class of triazolobenzodiazepines that is 4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine carrying methyl, phenyl and chloro substituents at positions 1, 6 and 8 respectively. Alprazolam is only found in individuals that have taken this drug.	2.04	1	0	organochlorine compound; triazolobenzodiazepine	anticonvulsant; anxiolytic drug; GABA agonist; muscle relaxant; sedative; xenobiotic
amantadine amant: an antiviral compound consisting of an adamantane derivative chemically linked to a water-solube polyanioic matrix; structure in first source	1.99	1	0	adamantanes; primary aliphatic amine	analgesic; antiparkinson drug; antiviral drug; dopaminergic agent; NMDA receptor antagonist; non-narcotic analgesic
theophylline [no description available]	2.04	1	0	dimethylxanthine	adenosine receptor antagonist; anti-asthmatic drug; anti-inflammatory agent; bronchodilator agent; drug metabolite; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; fungal metabolite; human blood serum metabolite; immunomodulator; muscle relaxant; vasodilator agent
2-amino-4-phosphonobutyric acid 2-amino-4-phosphonobutyric acid: glutamate antagonist in locust muscle; structure; do not confuse with L-AP4, which is the propionic acid version	2.02	1	0
aspirin Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.	2.02	1	0	benzoic acids; phenyl acetates; salicylates	anticoagulant; antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; EC 1.1.1.188 (prostaglandin-F synthase) inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; plant activator; platelet aggregation inhibitor; prostaglandin antagonist; teratogenic agent
atenolol Atenolol: A cardioselective beta-1 adrenergic blocker possessing properties and potency similar to PROPRANOLOL, but without a negative inotropic effect.. atenolol : An ethanolamine compound having a (4-carbamoylmethylphenoxy)methyl group at the 1-position and an N-isopropyl substituent.	7.43	2	0	ethanolamines; monocarboxylic acid amide; propanolamine	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; sympatholytic agent; xenobiotic
atrazine [no description available]	7.03	1	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.	7.49	2	0	azobenzenes
2,2-bis(4-glycidyloxyphenyl)propane 2,2-bis(4-glycidyloxyphenyl)propane: structure	1.96	1	0	diarylmethane
barbital 5,5-diethylbarbituric acid : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by two ethyl groups. Formerly used as a hypnotic (sleeping aid).	7.36	2	0	barbiturates	drug allergen
benzyl benzoate benzyl benzoate: structure; acarosan, a moist powder composed of wetted cellulose and benzyl benzoate, is used on carpets as an acaricide. benzyl benzoate : A benzoate ester obtained by the formal condensation of benzoic acid with benzyl alcohol. It has been isolated from the plant species of the genus Polyalthia.	2.04	1	0	benzoate ester; benzyl ester	acaricide; plant metabolite; scabicide
benzyl isothiocyanate benzyl isothiocyanate: inhibits carcinogen-induced neoplasia; structure in Negwer, 5th ed, #715; also promotes urinary bladder carcinoma	2.04	1	0	benzenes; isothiocyanate	antibacterial drug
betaxolol [no description available]	2.04	1	0	propanolamine	antihypertensive agent; beta-adrenergic antagonist; sympatholytic agent
biperiden Biperiden: A muscarinic antagonist that has effects in both the central and peripheral nervous systems. It has been used in the treatment of arteriosclerotic, idiopathic, and postencephalitic parkinsonism. It has also been used to alleviate extrapyramidal symptoms induced by phenothiazine derivatives and reserpine.. biperiden : A member of the class of piperidines that is N-propylpiperidine in which the methyl hydrogens have been replaced by hydroxy, phenyl, and 5-norbornen-2-yl groups. A muscarinic antagonist affecting both the central and peripheral nervous systems, it is used in the treatment of all forms of Parkinson's disease.	2.04	1	0	piperidines; tertiary alcohol; tertiary amino compound	antidote to sarin poisoning; antidyskinesia agent; antiparkinson drug; muscarinic antagonist; parasympatholytic
bisoprolol Bisoprolol: A cardioselective beta-1 adrenergic blocker. It is effective in the management of HYPERTENSION and ANGINA PECTORIS.	2.04	1	0	secondary alcohol; secondary amine	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; sympatholytic agent
verapamil Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.	2.73	3	0	aromatic ether; nitrile; polyether; tertiary amino compound
camphor, (+-)-isomer [no description available]	2.06	1	0	bornane monoterpenoid; cyclic monoterpene ketone	plant metabolite
chlorpromazine Chlorpromazine: The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class chlorpromazine's antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking DOPAMINE RECEPTORS. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup.. chlorpromazine : A substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropanamine moiety.	2.04	1	0	organochlorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; phenothiazine antipsychotic drug
platinum tetrachloride platinum chloride: RN given refers to cpd with unspecified MF; structure in first source: K2PtCl; see also platinum tetrachloride. platinum dichloride : A platinum coordination entity consisting of platinum(II) bound to two chlorine atoms.	1.98	1	0	platinum coordination entity	catalyst; reagent
clofibric acid Clofibric Acid: An antilipemic agent that is the biologically active metabolite of CLOFIBRATE.. clofibric acid : A monocarboxylic acid that is isobutyric acid substituted at position 2 by a p-chlorophenoxy group. It is a metabolite of the drug clofibrate.	2.02	1	0	aromatic ether; monocarboxylic acid; monochlorobenzenes	anticholesteremic drug; antilipemic drug; antineoplastic agent; herbicide; marine xenobiotic metabolite; PPARalpha agonist
clomipramine Clomipramine: A tricyclic antidepressant similar to IMIPRAMINE that selectively inhibits the uptake of serotonin in the brain. It is readily absorbed from the gastrointestinal tract and demethylated in the liver to form its primary active metabolite, desmethylclomipramine.. clomipramine : A dibenzoazepine that is 10,11-dihydro-5H-dibenzo[b,f]azepine which is substituted by chlorine at position 3 and in which the hydrogen attached to the nitrogen is replaced by a 3-(dimethylamino)propyl group. One of the more sedating tricyclic antidepressants, it is used as the hydrochloride salt for the treatment of depression as well as obsessive-compulsive disorder and phobias.	2.04	1	0	dibenzoazepine	anticoronaviral agent; antidepressant; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; serotonergic antagonist; serotonergic drug; serotonin uptake inhibitor
clotiazepam clotiazepam: was heading 1975-94 (see under AZEPINES 1978-90; was Y 6047 see under AZEPINES 1975-77); Y 6047 was see CLOTIAZEPAM 1978-94; use AZEPINES to search CLOTIAZEPAM 1975-94; thienodiazepine derivative with actions similar to those of benzodiazepines	2.04	1	0	organic molecular entity
4-cresol 4-cresol: RN given refers to parent cpd. p-cresol : A cresol that consists of toluene substituted by a hydroxy group at position 4. It is a metabolite of aromatic amino acid metabolism produced by intestinal microflora in humans and animals.	2.1	1	0	cresol	Escherichia coli metabolite; human metabolite; uremic toxin
cycloleucine Cycloleucine: An amino acid formed by cyclization of leucine. It has cytostatic, immunosuppressive and antineoplastic activities.. 1-aminocyclopentanecarboxylic acid : A non-proteinogenic alpha-amino acid that is cyclopentane substituted at position 1 by amino and carboxy groups.	1.98	1	0	non-proteinogenic alpha-amino acid	EC 2.5.1.6 (methionine adenosyltransferase) inhibitor
deferoxamine Deferoxamine: Natural product isolated from Streptomyces pilosus. It forms iron complexes and is used as a chelating agent, particularly in the mesylate form.. desferrioxamine B : An acyclic desferrioxamine that is butanedioic acid in which one of the carboxy groups undergoes formal condensation with the primary amino group of N-(5-aminopentyl)-N-hydroxyacetamide and the second carboxy group undergoes formal condensation with the hydroxyamino group of N(1)-(5-aminopentyl)-N(1)-hydroxy-N(4)-[5-(hydroxyamino)pentyl]butanediamide. It is a siderophore native to Streptomyces pilosus biosynthesised by the DesABCD enzyme cluster as a high affinity Fe(III) chelator.	1.96	1	0	acyclic desferrioxamine	bacterial metabolite; ferroptosis inhibitor; iron chelator; siderophore
diazepam Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.	2.04	1	0	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; 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.	2.68	3	0	diester; phthalate ester	EC 3.2.1.20 (alpha-glucosidase) inhibitor; environmental contaminant; metabolite; plasticiser; teratogenic agent
dicamba Dicamba: A chlorinated organic herbicide.. dicamba : A methoxybenzoic acid that is O-methylsalicylic acid substituted by chloro groups at positions 3 and 6.	2.76	3	0	dichlorobenzene; methoxybenzoic acid	agrochemical; environmental contaminant; herbicide; synthetic auxin; xenobiotic
diclofenac Diclofenac: A non-steroidal anti-inflammatory agent (NSAID) with antipyretic and analgesic actions. It is primarily available as the sodium salt.. diclofenac : A monocarboxylic acid consisting of phenylacetic acid having a (2,6-dichlorophenyl)amino group at the 2-position.	2.02	1	0	amino acid; aromatic amine; dichlorobenzene; monocarboxylic acid; secondary amino compound	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
dichlorodiphenyl dichloroethylene Dichlorodiphenyl Dichloroethylene: An organochlorine pesticide, it is the ethylene metabolite of DDT.	2.41	1	0	chlorophenylethylene; monochlorobenzenes	human xenobiotic metabolite; persistent organic pollutant
ddt 1,1-bis(p-chlorophenyl)-2,2,2-trichloroethane: structure in first source	2.41	1	0	benzenoid aromatic compound; chlorophenylethane; monochlorobenzenes; organochlorine insecticide	bridged diphenyl acaricide; carcinogenic agent; endocrine disruptor; persistent organic pollutant
diethyl pyrocarbonate Diethyl Pyrocarbonate: Preservative for wines, soft drinks, and fruit juices and a gentle esterifying agent.. diethyl pyrocarbonate : The diethyl ester of dicarbonic acid.	2	1	0	acyclic carboxylic anhydride
diphenyleneiodonium diphenyleneiodonium: structure in first source; NADPH oxidase inhibitor. dibenziodolium : An organic cation that is fluorene in which the methylene group is replaced by a positively charged iodine.	3.77	10	0	organic cation
valproic acid Valproic Acid: A fatty acid with anticonvulsant and anti-manic properties that is used in the treatment of EPILEPSY and BIPOLAR DISORDER. The mechanisms of its therapeutic actions are not well understood. It may act by increasing GAMMA-AMINOBUTYRIC ACID levels in the brain or by altering the properties of VOLTAGE-GATED SODIUM CHANNELS.. valproic acid : A branched-chain saturated fatty acid that comprises of a propyl substituent on a pentanoic acid stem.	2.04	1	0	branched-chain fatty acid; branched-chain saturated fatty acid	anticonvulsant; antimanic drug; EC 3.5.1.98 (histone deacetylase) inhibitor; GABA agent; neuroprotective agent; psychotropic drug; teratogenic agent
endothall endothall: minor descriptor (72-82); online & Index Medicus search DICARBOXYLIC ACIDS (72-82)	2.7	3	0
enflurane Enflurane: An extremely stable inhalation anesthetic that allows rapid adjustments of anesthesia depth with little change in pulse or respiratory rate.. enflurane : An ether in which the oxygen atom is connected to 2-chloro-1,1,2-trifluoroethyl and difluoromethyl groups.	2.04	1	0	ether; organochlorine compound; organofluorine compound	anaesthetic
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.	2.52	2	0
ethenzamide ethenzamide: structure	2.04	1	0	organic molecular entity
ether Ether: A mobile, very volatile, highly flammable liquid used as an inhalation anesthetic and as a solvent for waxes, fats, oils, perfumes, alkaloids, and gums. It is mildly irritating to skin and mucous membranes.. ether : An organooxygen compound with formula ROR, where R is not hydrogen.. diethyl ether : An ether in which the oxygen atom is linked to two ethyl groups.	8.97	14	0	ether; volatile organic compound	inhalation anaesthetic; non-polar solvent; refrigerant
ethylenediamine ethylenediamine: RN given refers to parent cpd; edamine is the recommended contraction for the ethylenediamine radical. ethylenediamine : An alkane-alpha,omega-diamine in which the alkane is ethane.	1.92	1	0	alkane-alpha,omega-diamine	GABA agonist
fentanyl Fentanyl: A potent narcotic analgesic, abuse of which leads to habituation or addiction. It is primarily a mu-opioid agonist. Fentanyl is also used as an adjunct to general anesthetics, and as an anesthetic for induction and maintenance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1078). fentanyl : A monocarboxylic acid amide resulting from the formal condensation of the aryl amino group of N-phenyl-1-(2-phenylethyl)piperidin-4-amine with propanoic acid.	2.04	1	0	anilide; monocarboxylic acid amide; piperidines	adjuvant; anaesthesia adjuvant; anaesthetic; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic
fluoxetine Fluoxetine: The first highly specific serotonin uptake inhibitor. It is used as an antidepressant and often has a more acceptable side-effects profile than traditional antidepressants.. fluoxetine : A racemate comprising equimolar amounts of (R)- and (S)-fluoxetine. A selective serotonin reuptake inhibitor (SSRI), it is used (generally as the hydrochloride salt) for the treatment of depression (and the depressive phase of bipolar disorder), bullimia nervosa, and obsessive-compulsive disorder.. N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine : An aromatic ether consisting of 4-trifluoromethylphenol in which the hydrogen of the phenolic hydroxy group is replaced by a 3-(methylamino)-1-phenylpropyl group.	2.04	1	0	(trifluoromethyl)benzenes; aromatic ether; secondary amino compound
fomepizole Fomepizole: A pyrazole and competitive inhibitor of ALCOHOL DEHYDROGENASE that is used for the treatment of poisoning by ETHYLENE GLYCOL or METHANOL.. fomepizole : A member of the class of pyrazoles that is 1H-pyrazole substituted by a methyl group at position 4.	8.15	1	0	pyrazoles	antidote; EC 1.1.1.1 (alcohol dehydrogenase) inhibitor; protective agent
furazolidone Furazolidone: A nitrofuran derivative with antiprotozoal and antibacterial activity. Furazolidone acts by gradual inhibition of monoamine oxidase. (From Martindale, The Extra Pharmacopoeia, 30th ed, p514). furazolidone : A member of the class of oxazolidines that is 1,3-oxazolidin-2-one in which the hydrogen attached to the nitrogen is replaced by an N-{[(5-nitro-2-furyl)methylene]amino} group. It has antibacterial and antiprotozoal properties, and is used in the treatment of giardiasis and cholera.	1.97	1	0	nitrofuran antibiotic; oxazolidines	antibacterial drug; antiinfective agent; antitrichomonal drug; EC 1.4.3.4 (monoamine oxidase) inhibitor
2,5-dihydroxybenzoic acid 2,5-dihydroxybenzoic acid: RN given refers to parent cpd; a oxidative product of saligenin. 2,5-dihydroxybenzoic acid : A dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions.	2.01	1	0	dihydroxybenzoic acid	EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; fungal metabolite; human metabolite; MALDI matrix material; mouse metabolite
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.	2.04	1	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.	7.74	3	0	carboxamidine; guanidines; one-carbon compound
1-(5-isoquinolinesulfonyl)-2-methylpiperazine 1-(5-Isoquinolinesulfonyl)-2-Methylpiperazine: A specific protein kinase C inhibitor, which inhibits superoxide release from human neutrophils (PMN) stimulated with phorbol myristate acetate or synthetic diacylglycerol.. 1-(5-isoquinolinesulfonyl)-2-methylpiperazine : A member of the class of N-sulfonylpiperazines that is 2-methylpiperazine substituted at position 1 by a 5-isoquinolinesulfonyl group.	1.99	1	0	isoquinolines; N-sulfonylpiperazine	EC 2.7.11.13 (protein kinase C) inhibitor
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.	2.39	2	0	aromatic ketone; hydroxypiperidine; monochlorobenzenes; organofluorine compound; tertiary alcohol	antidyskinesia agent; antiemetic; dopaminergic antagonist; first generation antipsychotic; serotonergic antagonist
halothane [no description available]	3.33	7	0	haloalkane; organobromine compound; organochlorine compound; organofluorine compound	inhalation anaesthetic
hexestrol [no description available]	1.93	1	0	stilbenoid
hexobarbital Hexobarbital: A barbiturate that is effective as a hypnotic and sedative.. hexobarbital : A member of the class of barbiturates taht is barbituric acid substituted at N-1 by methyl and at C-5 by methyl and cyclohex-1-enyl groups.	2.04	1	0	barbiturates
beta-thujaplicin beta-thujaplicin: structure. beta-thujaplicin : A monoterpenoid that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2 and an isopropyl group at position 4. Isolated from Thuja plicata and Chamaecyparis obtusa, it exhibits antimicrobial activities.	7.02	1	0	cyclic ketone; enol; monoterpenoid	antibacterial agent; antifungal agent; antineoplastic agent; antiplasmodial drug; plant metabolite
ethidium Ethidium: A trypanocidal agent and possible antiviral agent that is widely used in experimental cell biology and biochemistry. Ethidium has several experimentally useful properties including binding to nucleic acids, noncompetitive inhibition of nicotinic acetylcholine receptors, and fluorescence among others. It is most commonly used as the bromide.. ethidium : The fluorescent compound widely used in experimental cell biology and biochemistry to reveal double-stranded DNA and RNA.	2.01	1	0	phenanthridines	fluorochrome; intercalator
hydroxyurea [no description available]	2	1	0	one-carbon compound; ureas	antimetabolite; antimitotic; antineoplastic agent; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; genotoxin; immunomodulator; radical scavenger; teratogenic agent
hydroxyzine Hydroxyzine: A histamine H1 receptor antagonist that is effective in the treatment of chronic urticaria, dermatitis, and histamine-mediated pruritus. Unlike its major metabolite CETIRIZINE, it does cause drowsiness. It is also effective as an antiemetic, for relief of anxiety and tension, and as a sedative.. hydroxyzine : A N-alkylpiperazine that is piperzine in which the nitrogens atoms are substituted by 2-(2-hydroxyethoxy)ethyl and (4-chlorophenyl)(phenyl)methyl groups respectively.	2.04	1	0	hydroxyether; monochlorobenzenes; N-alkylpiperazine	anticoronaviral agent; antipruritic drug; anxiolytic drug; dermatologic drug; H1-receptor antagonist
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	2.81	3	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
lidocaine Lidocaine: A local anesthetic and cardiac depressant used as an antiarrhythmia agent. Its actions are more intense and its effects more prolonged than those of PROCAINE but its duration of action is shorter than that of BUPIVACAINE or PRILOCAINE.. lidocaine : The monocarboxylic acid amide resulting from the formal condensation of N,N-diethylglycine with 2,6-dimethylaniline.	2.04	1	0	benzenes; monocarboxylic acid amide; tertiary amino compound	anti-arrhythmia drug; drug allergen; environmental contaminant; local anaesthetic; xenobiotic
imipramine Imipramine: The prototypical tricyclic antidepressant. It has been used in major depression, dysthymia, bipolar depression, attention-deficit disorders, agoraphobia, and panic disorders. It has less sedative effect than some other members of this therapeutic group.. imipramine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine substituted by a 3-(dimethylamino)propyl group at the nitrogen atom.	2.04	1	0	dibenzoazepine	adrenergic uptake inhibitor; antidepressant; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
iodoacetamide [no description available]	2.03	1	0
indolepropionic acid indolepropionic acid: structure in third source. 3-(1H-indol-3-yl)propanoic acid : An indol-3-yl carboxylic acid that is propionic acid substituted by a 1H-indol-3-yl group at position 3.	2.03	1	0	indol-3-yl carboxylic acid	auxin; human metabolite; plant metabolite
isoflurane Isoflurane: A stable, non-explosive inhalation anesthetic, relatively free from significant side effects.	5.21	3	1	organofluorine compound	inhalation anaesthetic
2-propanol 2-Propanol: An isomer of 1-PROPANOL. It is a colorless liquid having disinfectant properties. It is used in the manufacture of acetone and its derivatives and as a solvent. Topically, it is used as an antiseptic.. propan-2-ol : A secondary alcohol that is propane in which one of the hydrogens attached to the central carbon is substituted by a hydroxy group.	2.04	1	0	secondary alcohol; secondary fatty alcohol	protic solvent
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.	2.08	1	0	catechols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; sympathomimetic agent
staurosporine aglycone staurosporine aglycone: metabolite from culture broth of Nocardiopsis sp.; a neurotrophin antag; inhibits BDNF TrkB receptor	2.41	2	0
ketamine Ketamine: A cyclohexanone derivative used for induction of anesthesia. Its mechanism of action is not well understood, but ketamine can block NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE) and may interact with sigma receptors.. ketamine : A member of the class of cyclohexanones in which one of the hydrogens at position 2 is substituted by a 2-chlorophenyl group, while the other is substituted by a methylamino group.	4.61	1	1	cyclohexanones; monochlorobenzenes; secondary amino compound	analgesic; environmental contaminant; intravenous anaesthetic; neurotoxin; NMDA receptor antagonist; xenobiotic
kinetin Kinetin: A furanyl adenine found in PLANTS and FUNGI. It has plant growth regulation effects.. cytokinin : A phytohormone that promote cell division, or cytokinesis, in plant roots and shoots.. kinetin : A member of the class of 6-aminopurines that is adenine carrying a (furan-2-ylmethyl) substituent at the exocyclic amino group.	4.21	17	0	6-aminopurines; furans	cytokinin; geroprotector
lauric acid dodecanoic acid : A straight-chain, twelve-carbon medium-chain saturated fatty acid with strong bactericidal properties; the main fatty acid in coconut oil and palm kernel oil.	2.05	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; antibacterial agent; plant metabolite
lorazepam Lorazepam: A benzodiazepine used as an anti-anxiety agent with few side effects. It also has hypnotic, anticonvulsant, and considerable sedative properties and has been proposed as a preanesthetic agent.	2.04	1	0	benzodiazepine
mechlorethamine nitrogen mustard : Compounds having two beta-haloalkyl groups bound to a nitrogen atom, as in (X-CH2-CH2)2NR.	1.92	1	0	nitrogen mustard; organochlorine compound	alkylating agent
memantine [no description available]	4.92	2	1	adamantanes; primary aliphatic amine	antidepressant; antiparkinson drug; dopaminergic agent; neuroprotective agent; NMDA receptor antagonist
methadone Methadone: A synthetic opioid that is used as the hydrochloride. It is an opioid analgesic that is primarily a mu-opioid agonist. It has actions and uses similar to those of MORPHINE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1082-3). methadone : A racemate comprising equimolar amounts of dextromethadone and levomethadone. It is a opioid analgesic which is used as a painkiller and as a substitute for heroin in the treatment of heroin addiction.. 6-(dimethylamino)-4,4-diphenylheptan-3-one : A ketone that is heptan-3-one substituted by a dimethylamino group at position 6 and two phenyl groups at position 4.	4.61	1	1	benzenes; diarylmethane; ketone; tertiary amino compound
methoxyflurane Methoxyflurane: An inhalation anesthetic. Currently, methoxyflurane is rarely used for surgical, obstetric, or dental anesthesia. If so employed, it should be administered with NITROUS OXIDE to achieve a relatively light level of anesthesia, and a neuromuscular blocking agent given concurrently to obtain the desired degree of muscular relaxation. (From AMA Drug Evaluations Annual, 1994, p180). methoxyflurane : An ether in which the two groups attached to the central oxygen atom are methyl and 2,2-dichloro-1,1-difluoroethyl.	2.86	4	0	ether; organochlorine compound; organofluorine compound	hepatotoxic agent; inhalation anaesthetic; nephrotoxic agent; non-narcotic analgesic
methyl salicylate methyl salicylate: used in over-the-counter liniments, ointments, lotions for relief of musculoskeletal aches and pains; has hemolytic effect on human & sheep erythrocytes; RN given refers to parent cpd; structure in Merck Index, 9th ed, #5990. methyl salicylate : A benzoate ester that is the methyl ester of salicylic acid.	2.08	1	0	benzoate ester; methyl ester; salicylates	flavouring agent; insect attractant; metabolite
methylphenidate Methylphenidate: A central nervous system stimulant used most commonly in the treatment of ATTENTION DEFICIT DISORDER in children and for NARCOLEPSY. Its mechanisms appear to be similar to those of DEXTROAMPHETAMINE. The d-isomer of this drug is referred to as DEXMETHYLPHENIDATE HYDROCHLORIDE.. methylphenidate : A racemate comprising equimolar amounts of the two threo isomers of methyl phenyl(piperidin-2-yl)acetate. A central stimulant and indirect-acting sympathomimetic, is used (generally as the hydrochloride salt) in the treatment of hyperactivity disorders in children and for the treatment of narcolepsy.. methyl phenyl(piperidin-2-yl)acetate : A amino acid ester that is methyl phenylacetate in which one of the hydrogens alpha to the carbonyl group is replaced by a piperidin-2-yl group.	2.04	1	0	beta-amino acid ester; methyl ester; piperidines
metoprolol Metoprolol: A selective adrenergic beta-1 blocking agent that is commonly used to treat ANGINA PECTORIS; HYPERTENSION; and CARDIAC ARRHYTHMIAS.. metoprolol : A propanolamine that is 1-(propan-2-ylamino)propan-2-ol substituted by a 4-(2-methoxyethyl)phenoxy group at position 1.	2.04	1	0	aromatic ether; propanolamine; secondary alcohol; secondary amino compound	antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; geroprotector; xenobiotic
metronidazole Metronidazole: A nitroimidazole used to treat AMEBIASIS; VAGINITIS; TRICHOMONAS INFECTIONS; GIARDIASIS; ANAEROBIC BACTERIA; and TREPONEMAL INFECTIONS.. metronidazole : A member of the class of imidazoles substituted at C-1, -2 and -5 with 2-hydroxyethyl, nitro and methyl groups respectively. It has activity against anaerobic bacteria and protozoa, and has a radiosensitising effect on hypoxic tumour cells. It may be given by mouth in tablets, or as the benzoate in an oral suspension. The hydrochloride salt can be used in intravenous infusions. Metronidazole is a prodrug and is selective for anaerobic bacteria due to their ability to intracellularly reduce the nitro group of metronidazole to give nitroso-containing intermediates. These can covalently bind to DNA, disrupting its helical structure, inducing DNA strand breaks and inhibiting bacterial nucleic acid synthesis, ultimately resulting in bacterial cell death.	1.96	1	0	C-nitro compound; imidazoles; primary alcohol	antiamoebic agent; antibacterial drug; antimicrobial agent; antiparasitic agent; antitrichomonal drug; environmental contaminant; prodrug; radiosensitizing agent; xenobiotic
metyrapone Metyrapone: An inhibitor of the enzyme STEROID 11-BETA-MONOOXYGENASE. It is used as a test of the feedback hypothalamic-pituitary mechanism in the diagnosis of CUSHING SYNDROME.. metyrapone : An aromatic ketone that is 3,3-dimethylbutan-2-one in which the methyl groups at positions 1 and 4 are replaced by pyridin-3-yl groups. A steroid 11beta-monooxygenase (EC 1.14.15.4) inhibitor, it is used in the diagnosis of adrenal insufficiency.	1.96	1	0	aromatic ketone	antimetabolite; diagnostic agent; EC 1.14.15.4 (steroid 11beta-monooxygenase) inhibitor
midazolam Midazolam: A short-acting hypnotic-sedative drug with anxiolytic and amnestic properties. It is used in dentistry, cardiac surgery, endoscopic procedures, as preanesthetic medication, and as an adjunct to local anesthesia. The short duration and cardiorespiratory stability makes it useful in poor-risk, elderly, and cardiac patients. It is water-soluble at pH less than 4 and lipid-soluble at physiological pH.. midazolam : An imidazobenzodiazepine that is 4H-imidazo[1,5-a][1,4]benzodiazepine which is substituted by a methyl, 2-fluorophenyl and chloro groups at positions 1, 6 and 8, respectively.	2.04	1	0	imidazobenzodiazepine; monofluorobenzenes; organochlorine compound	anticonvulsant; antineoplastic agent; anxiolytic drug; apoptosis inducer; central nervous system depressant; GABAA receptor agonist; general anaesthetic; muscle relaxant; sedative
monodansylcadaverine monodansylcadaverine: inhibits cross linkage of fibrin. monodansylcadaverine : A sulfonamide obtained by formal condensation of the sulfo group of 5-(dimethylamino)naphthalene-1-sulfonic acid with one of the amino groups of cadaverine.	2.08	1	0	aminonaphthalene; primary amino compound; sulfonamide; tertiary amino compound	EC 2.3.2.13 (protein-glutamine gamma-glutamyltransferase) inhibitor; fluorochrome; protective agent
deet N,N-diethyl-m-toluamide : A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of m-toluic acid with the nitrogen of diethylamine. First developed by the U.S. Army in 1946 for use by military personnel in insect-infested areas, it is the most widely used insect repellent worldwide.	1.94	1	0	benzamides; monocarboxylic acid amide	environmental contaminant; insect repellent; xenobiotic
nalidixic acid [no description available]	2.04	1	0	1,8-naphthyridine derivative; monocarboxylic acid; quinolone antibiotic	antibacterial drug; antimicrobial agent; DNA synthesis inhibitor
netropsin Netropsin: A basic polypeptide isolated from Streptomyces netropsis. It is cytotoxic and its strong, specific binding to A-T areas of DNA is useful to genetics research.	6.99	1	0
nitrazepam Nitrazepam: A benzodiazepine derivative used as an anticonvulsant and hypnotic.. nitrazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one which is substituted at positions 5 and 7 by phenyl and nitro groups, respectively. It is used as a hypnotic for the short-term management of insomnia and for the treatment of epileptic spasms in infants (West's syndrome).	2.04	1	0	1,4-benzodiazepinone; C-nitro compound	anticonvulsant; antispasmodic drug; drug metabolite; GABA modulator; sedative
nitroglycerin Nitroglycerin: A volatile vasodilator which relieves ANGINA PECTORIS by stimulating GUANYLATE CYCLASE and lowering cytosolic calcium. It is also sometimes used for TOCOLYSIS and explosives.. nitroglycerol : A nitrate ester that is glycerol in which nitro group(s) replace the hydrogen(s) attached to one or more of the hydroxy groups.. nitroglycerin : A nitroglycerol that is glycerol in which the hydrogen atoms of all three hydroxy groups are replaced by nitro groups. It acts as a prodrug, releasing nitric oxide to open blood vessels and so alleviate heart pain.	1.93	1	0	nitroglycerol	explosive; muscle relaxant; nitric oxide donor; prodrug; tocolytic agent; vasodilator agent; xenobiotic
omeprazole Omeprazole: A 4-methoxy-3,5-dimethylpyridyl, 5-methoxybenzimidazole derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits an H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS.. omeprazole : A racemate comprising equimolar amounts of (R)- and (S)-omeprazole.. 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole : A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted by a [4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl group at position 2 and a methoxy group at position 5.	2.17	1	0	aromatic ether; benzimidazoles; pyridines; sulfoxide
oxprenolol Oxprenolol: A beta-adrenergic antagonist used in the treatment of hypertension, angina pectoris, arrhythmias, and anxiety.	2.04	1	0	aromatic ether
quinone benzoquinone : The simplest members of the class of benzoquinones, consisting of cyclohexadiene which is substituted by two oxo groups.. 1,4-benzoquinone : The simplest member of the class of 1,4-benzoquinones, obtained by the formal oxidation of hydroquinone to the corresponding diketone. It is a metabolite of benzene.. quinone : Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included).	2.1	1	0	1,4-benzoquinones	cofactor; human xenobiotic metabolite; mouse metabolite
pargyline Pargyline: A monoamine oxidase inhibitor with antihypertensive properties.	2.03	1	0	aromatic amine
pd 98059 2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one: inhibits MAP kinase kinase (MEK) activity, p42 MAPK and p44 MAPK; structure in first source. 2-(2-amino-3-methoxyphenyl)chromen-4-one : A member of the class of monomethoxyflavones that is 3'-methoxyflavone bearing an additional amino substituent at position 2'.	2.7	3	0	aromatic amine; monomethoxyflavone	EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector
pentobarbital Pentobarbital: A short-acting barbiturate that is effective as a sedative and hypnotic (but not as an anti-anxiety) agent and is usually given orally. It is prescribed more frequently for sleep induction than for sedation but, like similar agents, may lose its effectiveness by the second week of continued administration. (From AMA Drug Evaluations Annual, 1994, p236). pentobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and sec-pentyl groups.	7.34	2	0	barbiturates	GABAA receptor agonist
phenobarbital Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.	2.39	2	0	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
pindolol Pindolol: A moderately lipophilic beta blocker (ADRENERGIC BETA-ANTAGONISTS). It is non-cardioselective and has intrinsic sympathomimetic actions, but little membrane-stabilizing activity. (From Martindale, The Extra Pharmocopoeia, 30th ed, p638). pindolol : A member of the class of indols which is the 2-hydroxy-3-(isopropylamino)propyl ether derivative of 1H-indol-4-ol.	2.04	1	0	indoles; secondary amine	antiglaucoma drug; antihypertensive agent; beta-adrenergic antagonist; serotonergic antagonist; vasodilator agent
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.	2.44	2	0	inorganic chloride; inorganic potassium salt; potassium salt	fertilizer
potassium iodide Potassium Iodide: An inorganic compound that is used as a source of iodine in thyrotoxic crisis and in the preparation of thyrotoxic patients for thyroidectomy. (From Dorland, 27th ed). potassium iodide : A metal iodide salt with a K(+) counterion. It is a scavenger of hydroxyl radicals.	2.7	3	0	potassium salt	expectorant; radical scavenger
practolol Practolol: A beta-1 adrenergic antagonist that has been used in the emergency treatment of CARDIAC ARRYTHMIAS.. practolol : N-(4-Hydroxyphenyl)acetamide in which the hydrogen of the phenolic hydroxy group is substituted by a 3-(isopropylaminoamino)-2-hydroxypropyl group. A selective beta blocker, it has been used in the emergency treatment of cardiac arrhythmias.	2.04	1	0	acetamides; ethanolamines; propanolamine; secondary alcohol; secondary amino compound	anti-arrhythmia drug; beta-adrenergic antagonist
propranolol Propranolol: A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs.. propranolol : A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.	2.04	1	0	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic
propyl gallate Propyl Gallate: Antioxidant for foods, fats, oils, ethers, emulsions, waxes, and transformer oils.	2.41	2	0	trihydroxybenzoic acid
safrole Safrole: A member of the BENZODIOXOLES that is a constituent of several VOLATILE OILS, notably SASSAFRAS oil. It is a precursor in the synthesis of the insecticide PIPERONYL BUTOXIDE and the drug N-methyl-3,4-methylenedioxyamphetamine (MDMA).. safrole : A member of the class of benzodioxoles that is 1,3-benzodioxole which is substituted by an allyl group at position 5. It is found in several plants, including black pepper, cinnamon and nutmeg, and is present in several essential oils, notably that of sassafras. It has insecticidal properties and has been used as a topical antiseptic. Although not thought to pose a significant carcinogenic risk to humans, findings of weak carcinogenicity in rats have resulted in the banning of its (previously widespread) use in perfumes and soaps, and as a food additive.	7.37	2	0	benzodioxoles	flavouring agent; insecticide; metabolite; plant metabolite
sevoflurane Sevoflurane: A non-explosive inhalation anesthetic used in the induction and maintenance of general anesthesia. It does not cause respiratory irritation and may also prevent PLATELET AGGREGATION.. sevoflurane : An ether compound having fluoromethyl and 1,1,1,3,3,3-hexafluoroisopropyl as the two alkyl groups.	2.04	1	0	ether; organofluorine compound	central nervous system depressant; inhalation anaesthetic; platelet aggregation inhibitor
ponalrestat [no description available]	2.21	1	0	phthalazines
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.	1.99	1	0	long-chain fatty acid; saturated fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; human metabolite; plant metabolite
succinylcholine Succinylcholine: A quaternary skeletal muscle relaxant usually used in the form of its bromide, chloride, or iodide. It is a depolarizing relaxant, acting in about 30 seconds and with a duration of effect averaging three to five minutes. Succinylcholine is used in surgical, anesthetic, and other procedures in which a brief period of muscle relaxation is called for.. succinylcholine : A quaternary ammonium ion that is the bis-choline ester of succinic acid.	1.94	1	0	quaternary ammonium ion; succinate ester	drug allergen; muscle relaxant; neuromuscular agent
tegafur [no description available]	2.04	1	0	organohalogen compound; pyrimidines
tetraethylammonium Tetraethylammonium: A potassium-selective ion channel blocker. (From J Gen Phys 1994;104(1):173-90)	2.47	2	0	quaternary ammonium ion
krypton Krypton: A noble gas that is found in the atmosphere. It has the atomic symbol Kr, atomic number 36, atomic weight 83.80, and has been used in electric bulbs.	1.93	1	0	monoatomic krypton; noble gas atom; p-block element atom
thioridazine Thioridazine: A phenothiazine antipsychotic used in the management of PHYCOSES, including SCHIZOPHRENIA.. thioridazine : A phenothiazine derivative having a methylsulfanyl subsitituent at the 2-position and a (1-methylpiperidin-2-yl)ethyl] group at the N-10 position.	2.04	1	0	phenothiazines; piperidines	alpha-adrenergic antagonist; dopaminergic antagonist; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; first generation antipsychotic; H1-receptor antagonist; serotonergic antagonist
tolbutamide Tolbutamide: A sulphonylurea hypoglycemic agent with actions and uses similar to those of CHLORPROPAMIDE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p290). tolbutamide : An N-sulfonylurea that consists of 1-butylurea having a tosyl group attached at the 3-position.	2.04	1	0	N-sulfonylurea	human metabolite; hypoglycemic agent; insulin secretagogue; potassium channel blocker
trifluoperazine [no description available]	2.04	1	0	N-alkylpiperazine; N-methylpiperazine; organofluorine compound; phenothiazines	antiemetic; calmodulin antagonist; dopaminergic antagonist; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor; phenothiazine antipsychotic drug
trihexyphenidyl Trihexyphenidyl: One of the centrally acting MUSCARINIC ANTAGONISTS used for treatment of PARKINSONIAN DISORDERS and drug-induced extrapyramidal movement disorders and as an antispasmodic.	2.04	1	0	amine
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.	1.96	1	0	aminopyrimidine; methoxybenzenes	antibacterial drug; diuretic; drug allergen; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; environmental contaminant; xenobiotic
tripelennamine Tripelennamine: A histamine H1 antagonist with low sedative action but frequent gastrointestinal irritation. It is used to treat ASTHMA; HAY FEVER; URTICARIA; and RHINITIS; and also in veterinary applications. Tripelennamine is administered by various routes, including topically.	1.92	1	0	aromatic amine
tyramine [no description available]	2.72	3	0	monoamine molecular messenger; primary amino compound; tyramines	EC 3.1.1.8 (cholinesterase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter
urethane [no description available]	2.35	2	0	carbamate ester	fungal metabolite; mutagen
vesamicol vesamicol: RN given refers to parent cpd; structure	1.98	1	0	piperidines
sorbitol D-glucitol : The D-enantiomer of glucitol (also known as D-sorbitol).	2.97	4	0	glucitol	cathartic; Escherichia coli metabolite; food humectant; human metabolite; laxative; metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite; sweetening agent
thymidine [no description available]	2.75	3	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
triethylenemelamine Triethylenemelamine: Toxic alkylating agent used in industry; also as antineoplastic and research tool to produce chromosome aberrations and cancers.	2.34	2	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.	2.7	3	0	4-hydroxyproline; L-alpha-amino acid zwitterion	human metabolite; mouse metabolite; plant metabolite
idoxuridine [no description available]	2.01	1	0	organoiodine compound; pyrimidine 2'-deoxyribonucleoside	antiviral drug; DNA synthesis inhibitor
diethylnitrosamine Diethylnitrosamine: A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties.. N-nitrosodiethylamine : A nitrosamine that is N-ethylethanamine substituted by a nitroso group at the N-atom.	2	1	0	nitrosamine	carcinogenic agent; hepatotoxic agent; mutagen
carbon tetrachloride Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.	3.38	7	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
cantharidin Cantharidin: A toxic compound, isolated from the Spanish fly or blistering beetle (Lytta (Cantharis) vesicatoria) and other insects. It is a potent and specific inhibitor of protein phosphatases 1 (PP1) and 2A (PP2A). This compound can produce severe skin inflammation, and is extremely toxic if ingested orally.. cantharidin : A monoterpenoid with an epoxy-bridged cyclic dicarboxylic anhydride structure secreted by many species of blister beetle, and most notably by the Spanish fly, Lytta vesicatoria. Natural toxin inhibitor of protein phosphatases 1 and 2A.	3.28	6	0	cyclic dicarboxylic anhydride; monoterpenoid	EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; herbicide
alanine Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.	2.03	1	0	alanine zwitterion; alanine; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid	EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor; fundamental metabolite
serine Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.	8.02	4	0	L-alpha-amino acid; proteinogenic amino acid; serine family amino acid; serine zwitterion; serine	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
benz(a)anthracene benz(a)anthracene: 4 fused rings of which one is angular in contrast to the linear NAPHTHACENES. tetraphene : An angular ortho-fused polycyclic arene consisting of four fused benzene rings.	1.94	1	0	ortho-fused polycyclic arene; tetraphenes
aspartic acid Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.	5.14	8	0	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
glutamine Glutamine: A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from GLUTAMIC ACID and AMMONIA. It is the principal carrier of NITROGEN in the body and is an important energy source for many cells.. L-glutamine : An optically active form of glutamine having L-configuration.. glutamine : An alpha-amino acid that consists of butyric acid bearing an amino substituent at position 2 and a carbamoyl substituent at position 4.	4.49	7	0	amino acid zwitterion; glutamine family amino acid; glutamine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
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.	3.27	6	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
allyl isothiocyanate allyl isothiocyanate: used in the manufacture of flavors, war gases; medical use as a counterirritant; structure. allyl isothiocyanate : An isothiocyanate with the formula CH2=CHCH2N=C=S. A colorless oil with boiling point 152degreeC, it is responsible for the pungent taste of mustard, horseradish, and wasabi.	2.15	1	0	alkenyl isothiocyanate; isothiocyanate	antimicrobial agent; antineoplastic agent; apoptosis inducer; lachrymator; 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.	6.35	21	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.	5.31	50	0	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
tubocurarine Tubocurarine: A neuromuscular blocker and active ingredient in CURARE; plant based alkaloid of Menispermaceae.. tubocurarine : A benzylisoquinoline alkaloid muscle relaxant which constitutes the active component of curare.. isoquinoline alkaloid : Any alkaloid that has a structure based on an isoquinoline nucleus. They are derived from the amino acids like tyrosine and phenylalanine.	1.94	1	0	bisbenzylisoquinoline alkaloid	drug allergen; muscle relaxant; nicotinic antagonist
aminopyrine Aminopyrine: A pyrazolone with analgesic, anti-inflammatory, and antipyretic properties but has risk of AGRANULOCYTOSIS. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of CYTOCHROME P-450 metabolic activity in LIVER FUNCTION TESTS.. aminophenazone : A pyrazolone that is 1,2-dihydro-3H-pyrazol-3-one substituted by a dimethylamino group at position 4, methyl groups at positions 1 and 5 and a phenyl group at position 2. It exhibits analgesic, anti-inflammatory, and antipyretic properties.	1.96	1	0	pyrazolone; tertiary amino compound	antipyretic; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	2.05	1	0	adenosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite; human metabolite
triphenylethylene [no description available]	2.33	2	0	stilbenoid
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	1	0	tetrachlorophenol	xenobiotic metabolite
uridine [no description available]	2.25	1	0	uridines	drug metabolite; fundamental metabolite; human metabolite
uridine diphosphate Uridine Diphosphate: A uracil nucleotide containing a pyrophosphate group esterified to C5 of the sugar moiety.	2.54	2	0	pyrimidine ribonucleoside 5'-diphosphate; uridine 5'-phosphate	Escherichia coli metabolite; mouse metabolite
kanamycin a Kanamycin: Antibiotic complex produced by Streptomyces kanamyceticus from Japanese soil. Comprises 3 components: kanamycin A, the major component, and kanamycins B and C, the minor components.. kanamycin : Kanamycin is a naturally occurring antibiotic complex from Streptomyces kanamyceticus that consists of several components: kanamycin A, the major component (also usually designated as kanamycin), and kanamycins B, C, D and X the minor components.	2.01	1	0	kanamycins	bacterial metabolite
bromodeoxyuridine Bromodeoxyuridine: A nucleoside that substitutes for thymidine in DNA and thus acts as an antimetabolite. It causes breaks in chromosomes and has been proposed as an antiviral and antineoplastic agent. It has been given orphan drug status for use in the treatment of primary brain tumors.	2.11	1	0	pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent
galactose galactopyranose : The pyranose form of galactose.	3.59	8	0	D-galactose; galactopyranose	Escherichia coli metabolite; mouse metabolite
carbostyril Quinolones: A group of derivatives of naphthyridine carboxylic acid, quinoline carboxylic acid, or NALIDIXIC ACID.. quinolin-2(1H)-one : A quinolone that is 1,2-dihydroquinoline substituted by an oxo group at position 2.	2.51	2	0	monohydroxyquinoline; quinolone	bacterial xenobiotic metabolite
phenylephrine Phenylephrine: An alpha-1 adrenergic agonist used as a mydriatic, nasal decongestant, and cardiotonic agent.. phenylephrine : A member of the class of the class of phenylethanolamines that is (1R)-2-(methylamino)-1-phenylethan-1-ol carrying an additional hydroxy substituent at position 3 on the phenyl ring.	2.08	1	0	phenols; phenylethanolamines; secondary amino compound	alpha-adrenergic agonist; cardiotonic drug; mydriatic agent; nasal decongestant; protective agent; sympathomimetic agent; vasoconstrictor agent
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.	3.21	6	0	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
phenylethyl alcohol Phenylethyl Alcohol: An antimicrobial, antiseptic, and disinfectant that is used also as an aromatic essence and preservative in pharmaceutics and perfumery.. 2-phenylethanol : A primary alcohol that is ethanol substituted by a phenyl group at position 2.	2.13	1	0	benzenes; primary alcohol	Aspergillus metabolite; fragrance; plant growth retardant; plant metabolite; Saccharomyces cerevisiae metabolite
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	7.69	3	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
acepromazine Acepromazine: A phenothiazine that is used in the treatment of PSYCHOSES.. acepromazine : A member of the class of phenothiazines that is 10H-phenothiazine substituted by an acetyl group at position 2 and a 3-(dimethylamino)propyl group at position 10.	2.06	1	0	aromatic ketone; methyl ketone; phenothiazines; tertiary amino compound	phenothiazine antipsychotic drug
4-toluenesulfonic acid 4-toluenesulfonic acid: RN given refers to parent cpd; other RNs in 9th CI Form Index. toluene-4-sulfonic acid : An arenesulfonic acid that is benzenesulfonic acid in which the hydrogen at position 4 is replaced by a methyl group.	2.06	1	0	arenesulfonic acid; toluenes
leucine Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.	2.97	4	0	amino acid zwitterion; L-alpha-amino acid; leucine; proteinogenic amino acid; pyruvate family amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
ethyl methanesulfonate Ethyl Methanesulfonate: An antineoplastic agent with alkylating properties. It also acts as a mutagen by damaging DNA and is used experimentally for that effect.. ethyl methanesulfonate : A methanesulfonate ester resulting from the formal condensation of methanesulfonic acid with ethanol.	2.95	4	0	methanesulfonate ester	alkylating agent; antineoplastic agent; carcinogenic agent; genotoxin; mutagen; teratogenic agent
aniline [no description available]	1.96	1	0	anilines; primary arylamine
2-aminoisobutyric acid 2-aminoisobutyric acid: RN given refers to unlabeled cpd. 2-aminoisobutyric acid : A rare, non-protein amino acid and end-product of pyrimidine metabolism, excreted in urine and found in some antibiotics of fungal origin. With the exception of a few bacteria, it is non-metabolisable, and therefore used in bioassays.	3.56	8	0	2,2-dialkylglycine zwitterion; 2,2-dialkylglycine
dimethylnitrosamine Dimethylnitrosamine: A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties. It causes serious liver damage and is a hepatocarcinogen in rodents.	1.96	1	0	nitrosamine	geroprotector; mutagen
methionine Methionine: A sulfur-containing essential L-amino acid that is important in many body functions.. methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4.	7.59	41	0	aspartate family amino acid; L-alpha-amino acid; methionine zwitterion; methionine; proteinogenic amino acid	antidote to paracetamol poisoning; human metabolite; micronutrient; mouse metabolite; nutraceutical
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.	1.99	1	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.	8.44	7	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
gallamine triethiodide Gallamine Triethiodide: A synthetic nondepolarizing blocking drug. The actions of gallamine triethiodide are similar to those of TUBOCURARINE, but this agent blocks the cardiac vagus and may cause sinus tachycardia and, occasionally, hypertension and increased cardiac output. It should be used cautiously in patients at risk from increased heart rate but may be preferred for patients with bradycardia. (From AMA Drug Evaluations Annual, 1992, p198)	1.94	1	0
n-hexanal [no description available]	2.06	1	0	medium-chain fatty aldehyde; n-alkanal; saturated fatty aldehyde	human urinary metabolite
cycloheximide Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.	3.95	13	0	antibiotic fungicide; cyclic ketone; dicarboximide; piperidine antibiotic; piperidones; secondary alcohol	anticoronaviral agent; bacterial metabolite; ferroptosis inhibitor; neuroprotective agent; protein synthesis inhibitor
egtazic acid Egtazic Acid: A chelating agent relatively more specific for calcium and less toxic than EDETIC ACID.. ethylene glycol bis(2-aminoethyl)tetraacetic acid : A diether that is ethylene glycol in which the hydrogens of the hydroxy groups have been replaced by 2-[bis(carboxymethyl)amino]ethyl group respectively.	2.91	4	0	diether; tertiary amino compound; tetracarboxylic acid	chelator
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.	2.31	1	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.	8.97	14	0	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
hexachloroethane [no description available]	2.05	1	0	chlorocarbon; chloroethanes	carcinogenic agent; refrigerant
bromoacetate [no description available]	1.96	1	0
hexachloro-4-xylene hexachloro-4-xylene: structure	2.41	1	0
tubercidin Tubercidin: An antibiotic purine ribonucleoside that readily substitutes for adenosine in the biological system, but its incorporation into DNA and RNA has an inhibitory effect on the metabolism of these nucleic acids.. tubercidin : An N-glycosylpyrrolopyrimidine that is adenosine in which the in the 5-membered ring that is not attached to the ribose moiety is replaced by a carbon. Tubercidin is produced in the culture broth of Streptomyces tubericidus.	2.05	1	0	antibiotic antifungal agent; N-glycosylpyrrolopyrimidine; ribonucleoside	antimetabolite; antineoplastic agent; bacterial metabolite
mannitol [no description available]	8.42	7	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
asparagine Asparagine: A non-essential amino acid that is involved in the metabolic control of cell functions in nerve and brain tissue. It is biosynthesized from ASPARTIC ACID and AMMONIA by asparagine synthetase. (From Concise Encyclopedia Biochemistry and Molecular Biology, 3rd ed). asparagine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 2-amino-2-oxoethyl group.	7.6	1	0	amino acid zwitterion; asparagine; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
histidine Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.	7.24	12	1	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
n-pentanol n-pentanol: RN given refers to parent cpd. pentan-1-ol : A short-chain primary fatty alcohol that is pentane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It has been isolated from Melicope ptelefolia.	2.1	1	0	pentanol; short-chain primary fatty alcohol	human metabolite; plant metabolite
1,1,1-trichloroethane Trichloroethanes: Chlorinated ethanes which are used extensively as industrial solvents. They have been utilized in numerous home-use products including spot remover preparations and inhalant decongestant sprays. These compounds cause central nervous system and cardiovascular depression and are hepatotoxic. Include 1,1,1- and 1,1,2-isomers.. 1,1,1-trichloroethane : A member of the class of chloroethanes carrying three chloro substituents at position 1.	3.28	6	0	chloroethanes	polar solvent
valine Valine: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.. valine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group.. L-valine : The L-enantiomer of valine.	8.6	9	0	L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid; valine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
threonine Threonine: An essential amino acid occurring naturally in the L-form, which is the active form. It is found in eggs, milk, gelatin, and other proteins.. threonine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 1-hydroxyethyl group.	2.01	1	0	amino acid zwitterion; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid; threonine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
tryptophan Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.	8.25	6	0	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
isoleucine Isoleucine: An essential branched-chain aliphatic amino acid found in many proteins. It is an isomer of LEUCINE. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels.. isoleucine : A 2-amino-3-methylpentanoic acid having either (2R,3R)- or (2S,3S)-configuration.. L-isoleucine : The L-enantiomer of isoleucine.	3.32	6	0	aspartate family amino acid; isoleucine; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
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.	9.25	5	0	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
methyl bromide methyl bromide: used in ionization chambers, degreasing wool, extracting oils; insect fumigant; high concentrations can produce pulmonary edema,narcosis; chronic exposure can cause CNS depression,kidney injury; RN given refers to parent cpd; structure. bromomethane : A one-carbon compound in which the carbon is attached by single bonds to three hydrogen atoms and one bromine atom. It is produced naturally by marine algae.	2.35	2	0	bromohydrocarbon; bromomethanes; methyl halides	algal metabolite; fumigant insecticide; marine metabolite
ethane Ethane: A two carbon alkane with the formula H3C-CH3.. ethane : An alkane comprising of two carbon atoms.	6.56	61	0	alkane; gas molecular entity	plant metabolite; refrigerant
acetylene [no description available]	7.79	92	0	alkyne; gas molecular entity; terminal acetylenic compound
methyl chloride Methyl Chloride: A hydrocarbon used as an industrial solvent. It has been used as an aerosal propellent, as a refrigerant and as a local anesthetic. (From Martindale, The Extra Pharmacopoeia, 31st ed, p1403). chlorocarbon : Compounds consisting wholly of chlorine and carbon.. chloromethane : A one-carbon compound that is methane in which one of the hydrogens is replaced by a chloro group.	2.66	3	0	chloromethanes; methyl halides	marine metabolite; mutagen; refrigerant
methyl iodide methyl iodide: RN given refers to unlabeled cpd with MF of CH3-I. iodomethane : A member of the class of iodomethanes that is methane in which one of the hydrogens is replaced by iodine.	1.96	1	0	iodomethanes; methyl halides	fumigant insecticide
methylamine methyl group : An alkyl group that is the univalent group derived from methane by removal of a hydrogen atom.	2.68	3	0	methylamines; one-carbon compound; primary aliphatic amine	mouse metabolite
boranes Boranes: The collective name for the boron hydrides, which are analogous to the alkanes and silanes. Numerous boranes are known. Some have high calorific values and are used in high-energy fuels. (From Grant & Hackh's Chemical Dictionary, 5th ed). borane : The simplest borane, consisting of a single boron atom carrying three hydrogens.. boranes : The molecular hydrides of boron.	3.32	6	0	boranes; mononuclear parent hydride
propane Propane: A three carbon alkane with the formula H3CCH2CH3.	3.97	13	0	alkane; gas molecular entity	food propellant
methylacetylene methylacetylene: structure	3.5	2	0	alkyne; gas molecular entity; terminal acetylenic compound
ethyl chloride Ethyl Chloride: A gas that condenses under slight pressure. Because of its low boiling point ethyl chloride sprayed on skin produces an intense cold by evaporation. Cold blocks nerve conduction. Ethyl chloride has been used in surgery but is primarily used to relieve local pain in sports medicine.. chloroethane : The simplest and least toxic member of the class of chloroethanes, that is ethane in which a single hydrogen is substituted by a chlorine. A colourless gas at room temperature and pressure (boiling point 12degreeC), it is used as a mild topical anaesthetic to numb the skin prior to ear piercing, skin biopsies, etc., and is also used in the treatment of sports injuries. It was formerly used in the production of tetraethyllead.	3.67	10	0	chloroethanes	antipruritic drug; inhalation anaesthetic; local anaesthetic
vinyl chloride Vinyl Chloride: A gas that has been used as an aerosol propellant and is the starting material for polyvinyl resins. Toxicity studies have shown various adverse effects, particularly the occurrence of liver neoplasms.. chloroethene : A monohaloethene that is ethene in which one of the hydrogens has been replaced by a chloro group.	6.88	83	0	chloroethenes; gas molecular entity; monohaloethene	carcinogenic agent
vinyl fluoride [no description available]	2.36	2	0	gas molecular entity; monohaloethene
ethylamine ethylamine : A two-carbon primary aliphatic amine.	1.96	1	0	primary aliphatic amine	human metabolite
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.	8.11	5	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
methylene chloride Methylene Chloride: A chlorinated hydrocarbon that has been used as an inhalation anesthetic and acts as a narcotic in high concentrations. Its primary use is as a solvent in manufacturing and food technology.. dichloromethane : A member of the class of chloromethanes that is methane in which two of the hydrogens have been replaced by chlorine. A dense, non-flammible colourless liquid at room temperature (b.p. 40degreeC, d = 1.33) which is immiscible with water, it is widely used as a solvent, a paint stripper, and for the removal of caffeine from coffee and tea.	2.39	2	0	chloromethanes; volatile organic compound	carcinogenic agent; polar aprotic solvent; refrigerant
difluoromethane difluoromethane: structure given in first source	1.96	1	0	fluoromethanes	refrigerant
isocyanic acid isocyanic acid: structure. isocyanic acid : A colourless, volatile, poisonous inorganic compound with the formula HNCO; the simplest stable chemical compound that contains carbon, hydrogen, nitrogen, and oxygen, the four most commonly-found elements in organic chemistry and biology.	2.46	2	0	hydracid; one-carbon compound
carbon disulfide Carbon Disulfide: A colorless, flammable, poisonous liquid, CS2. It is used as a solvent, and is a counterirritant and has local anesthetic properties but is not used as such. It is highly toxic with pronounced CNS, hematologic, and dermatologic effects.	2.39	2	0	one-carbon compound; organosulfur compound
cyclopropane cyclopropane : A cycloalkane composed of three carbon atoms to form a ring.	3.83	12	0	cycloalkane; cyclopropanes	inhalation anaesthetic
ethylene oxide Ethylene Oxide: A colorless and flammable gas at room temperature and pressure. Ethylene oxide is a bactericidal, fungicidal, and sporicidal disinfectant. It is effective against most micro-organisms, including viruses. It is used as a fumigant for foodstuffs and textiles and as an agent for the gaseous sterilization of heat-labile pharmaceutical and surgical materials. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p794). oxirane : A saturated organic heteromonocyclic parent that is a three-membered heterocycle of two carbon atoms and one oxygen atom.	6.92	39	0	gas molecular entity; oxacycle; saturated organic heteromonocyclic parent	allergen; mouse metabolite; mutagen
boron trifluoride [no description available]	2.05	1	0	boron fluoride	NMR chemical shift reference compound
2-propylamine 2-propylamine: RN given refers to parent cpd	1.96	1	0	alkylamines; primary aliphatic amine
1,1-dichloroethane [no description available]	2.4	2	0	organochlorine compound
1,1-difluoroethane [no description available]	2.39	2	0
1,1-difluoroethylene 1,1-difluoroethylene: structure	2.38	2	0	olefinic compound; organofluorine compound
dichlorofluoromethane [no description available]	1.96	1	0
fluorocarbon 22 [no description available]	1.96	1	0	hydrochlorofluorocarbon
nitromethane nitromethane: structure. nitromethane : A primary nitroalkane that is methane in which one of the hydrogens is replace by a nitro group. A polar solvent (b.p. 101 degreeC), it is an important starting material in organic synthesis. It is also used as a fuel for rockets and radio-controlled models.	1.96	1	0	primary nitroalkane; volatile organic compound	EC 4.3.1.3 (histidine ammonia-lyase) inhibitor; explosive; NMR chemical shift reference compound; polar aprotic solvent
propylene oxide propylene oxide: structure. 1,2-epoxypropane : An epoxide that is oxirane substituted by a methyl group at position 2.	8.48	2	0	epoxide
tert-butyl alcohol tert-Butyl Alcohol: An isomer of butanol that contains a tertiary butyl group that consists of three methyl groups, each separately attached to a central (tertiary) carbon.. tert-butanol : A tertiary alcohol alcohol that is isobutane substituted by a hydroxy group at position 2.	1.97	1	0	tertiary alcohol	human xenobiotic metabolite
dichlorodifluoromethane dichlorodifluoromethane: refrigerant,aerosol propellant	1.99	1	0
methanesulfonic acid [no description available]	2.46	2	0	alkanesulfonic acid; one-carbon compound	Escherichia coli metabolite
tribromoethanol tribromoethanol: major descriptor (66-90); on-line search ETHANOL (66-90); INDEX MEDICUS search TRIBROMOETHANOL (66-90)	1.94	1	0	alcohol; organobromine compound
acetone cyanohydrin acetone cyanohydrin: RN given refers to unlabeled cpd; structure	6.93	1	0	cyanohydrin
1,1,1-trifluoro-2-chloroethane 1,1,1-trifluoro-2-chloroethane: volatile metabolite of halothane	2.04	1	0	organofluorine compound
trifluoroethanol Trifluoroethanol: A non-aqueous co-solvent that serves as tool to study protein folding. It is also used in various pharmaceutical, chemical and engineering applications.	1.96	1	0	fluoroalcohol
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.	2.68	3	0	monocarboxylic acid; organochlorine compound	carcinogenic agent; metabolite; mouse metabolite
1,1,2-trichloro-1,2,2-trifluoroethane [no description available]	2.21	1	0	chlorofluorocarbon; haloalkane	NMR solvent; refrigerant
freon 114 Freon 114: InChIKey: DDMOUSALMHHKOS-UHFFFAOYSA-N	1.96	1	0
perfluoroethane [no description available]	1.96	1	0	fluoroalkane; fluorocarbon	refrigerant
gibberellic acid gibberellic acid: RN given refers to (1alpha,2beta,4aalpha,4bbeta,10beta)-isomer; structure. gibberellin A3 : A C19-gibberellin that is a pentacyclic diterpenoid responsible for promoting growth and elongation of cells in plants. Initially identified in Gibberella fujikuroi,it differs from gibberellin A1 in the presence of a double bond between C-3 and C-4.	8.15	59	0	C19-gibberellin; gibberellin monocarboxylic acid; lactone; organic heteropentacyclic compound	mouse metabolite; plant metabolite
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.	2.04	1	0	benzenes; piperidines	anaesthetic; neurotoxin; NMDA receptor antagonist; psychotropic drug
butobarbital butobarbital: Butobarbital should be distinguished from Butabarbital (a synonym for Secbutabarbital)	2.04	1	0	barbiturates
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)	2.17	1	0	primary amino compound; triol	buffer
linalool linalool: RN given refers to parent cpd without isomeric designation; structure. linalool : A monoterpenoid that is octa-1,6-diene substituted by methyl groups at positions 3 and 7 and a hydroxy group at position 3. It has been isolated from plants like Ocimum canum.	2.02	1	0	monoterpenoid; tertiary alcohol	antimicrobial agent; fragrance; plant metabolite; volatile oil component
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.	6.02	25	1	alkadiene; hemiterpene; volatile organic compound	plant metabolite
isobutyl alcohol isobutyl alcohol: RN given refers to parent cpd	2.04	1	0	alkyl alcohol; primary alcohol	Saccharomyces cerevisiae metabolite
2-butanol 2-butanol: RN given is for parent cpd without isomeric designation. butan-2-ol : A secondary alcohol that is butane substituted by a hydroxy group at position 2.	1.96	1	0	secondary alcohol
methylethyl ketone methylethyl ketone: solvent; colorless synthetic resins, smokeless powders; may be irritating to eyes, mucous membranes; may be toxic in high concentrations; structure. butanone : Any ketone that is butane substituted by an oxo group at unspecified position.. butan-2-one : A dialkyl ketone that is a four-carbon ketone carrying a single keto- group at position C-2.	2.39	2	0	butanone; dialkyl ketone; methyl ketone; volatile organic compound	bacterial metabolite; polar aprotic solvent
1,1,2-trichloroethane 1,1,2-trichloroethane: RN given refers to cpd with locants as specified. 1,1,2-trichloroethane : A member of the class of chloroethanes that is ethane substituted by chloro groups at positions 1, 1 and 2.	2.48	2	0	chloroethanes
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.	5.73	80	0	chloroethenes	inhalation anaesthetic; mouse metabolite
dichloroacetaldehyde [no description available]	1.96	1	0	organochlorine compound
acrylamide [no description available]	1.98	1	0	acrylamides; N-acylammonia; primary carboxamide	alkylating agent; carcinogenic agent; Maillard reaction product; mutagen; neurotoxin
acrylic acid acrylic acid: RN given refers to parent cpd. acrylic acid : A alpha,beta-unsaturated monocarboxylic acid that is ethene substituted by a carboxy group.	7.71	3	0	alpha,beta-unsaturated monocarboxylic acid	metabolite
n-methylacetamide N-methylacetamide: RN given refers to parent cpd. N-methylacetamide : A monocarboxylic acid amide that is the N-methyl derivative of acetamide.	1.96	1	0	acetamides; monocarboxylic acid amide	metabolite
methyl acetate methyl acetate : An acetate ester resulting from the formal condensation of acetic acid with methanol. A low-boiling (57 degreeC) colourless, flammable liquid, it is used as a solvent for many resins and oils.	1.96	1	0	acetate ester; methyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; fragrance; polar aprotic solvent
nitroethane nitroethane : A nitroalkane that is ethane substituted by a nitro group.	1.96	1	0	primary nitroalkane
1,1,2,2-tetrachloroethane 1,1,2,2-tetrachloroethane: see also record for tetrachloroethane. 1,1,2,2-tetrachloroethane : A member of the class of chloroethanes that is ethane substituted by chloro groups at positions 1, 1, 2 and 2.	2.44	2	0	chloroethanes
camphene camphene : A monoterpene with a bicyclic skeleton that is bicyclo[2.2.1]heptane substituted by geminal methyl groups at position 2 and a methylidene group at position 3. It is a widespread natural product found in many essential oils.	2.11	1	0	carbobicyclic compound; monoterpene	fragrance; plant metabolite
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.	3.27	5	0	bisphenol	endocrine disruptor; environmental contaminant; xenobiotic; xenoestrogen
alpha-pinene [no description available]	2.57	2	0	pinene	plant metabolite
methylmethacrylate Methylmethacrylate: The methyl ester of methacrylic acid. It polymerizes easily to form POLYMETHYL METHACRYLATE. It is used as a bone cement.. methyl methacrylate : An enoate ester having methacrylic acid as the carboxylic acid component and methanol as the alcohol component.	3.48	8	0	enoate ester; methyl ester	allergen; polymerisation monomer
pyocyanine Pyocyanine: Antibiotic pigment produced by Pseudomonas aeruginosa.. pyocyanine : An iminium betaine that is 5-methylphenazin-5-ium which is substituted at position 1 by an oxidanidyl group. An antibiotic pigment produced by Pseudomonas aeruginosa.	2.1	1	0	iminium betaine; phenazines	antibacterial agent; bacterial metabolite; biological pigment; virulence factor
n-nitrosodiphenylamine N-nitrosodiphenylamine: RN given refers to parent cpd; structure in first source	2.04	1	0	phenylhydrazines
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.	3.98	13	0	naphthylacetic acid	synthetic auxin
penicillin v Penicillin V: A broad-spectrum penicillin antibiotic used orally in the treatment of mild to moderate infections by susceptible gram-positive organisms.. phenoxymethylpenicillin : A penicillin compound having a 6beta-(phenoxyacetyl)amino side-chain.	2.04	1	0	penicillin allergen; penicillin
symclosene trichloroisocyanuric acid: structure in first source	2.6	1	0	1,3,5-triazinanes; organochlorine compound
2-furoic acid 2-furoic acid: RN given refers to parent cpd. furoic acid : A monocarboxylic acid that consists of a furan ring having a single carboxylic acid group on any ring position and derivatives thereof.. 2-furoic acid : A furoic acid having the carboxylic acid group located at position 2.	2.1	1	0	furoic acid	bacterial xenobiotic metabolite; human xenobiotic metabolite; inhibitor; plant metabolite; Saccharomyces cerevisiae metabolite
2,3,5-triiodobenzoic acid 2,3,5-triiodobenzoic acid: inhibitor of auxin transport; RN given refers to parent cpd. 2,3,5-triiodobenzoic acid : A member of the class of benzoic acids that is benzoic acid in which the hydrogens at positions 2, 3 and 5 are replaced by iodine atoms. It is an auxin polar transport inhibitor.	3.65	9	0	benzoic acids; organoiodine compound	antiauxins
thymol Thymol: A phenol obtained from thyme oil or other volatile oils used as a stabilizer in pharmaceutical preparations, and as an antiseptic (antibacterial or antifungal) agent.. thymol : A phenol that is a natural monoterpene derivative of cymene.	2.8	3	0	monoterpenoid; phenols	volatile oil component
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	4.61	1	1	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
isatin tribulin: endogenous MONOAMINE OXIDASE inhibitory activity extractable into ethyl acetate found in brain and many mammalian tissues and fluids; ISATIN is a major component; produced in excess following alcohol withdrawal;	2.91	3	0	indoledione	EC 1.4.3.4 (monoamine oxidase) inhibitor; plant metabolite
phenidone phenidone: photographic developer; RN given refers to parent cpd; structure	2.08	1	0
methyleugenol methyleugenol: structure	2.11	1	0	phenylpropanoid
1-phenylpropanol 1-phenylpropanol: structure in first source	3.04	4	0	organic molecular entity
methyl benzoate methyl benzoate : A benzoate ester obtained by condensation of benzoic acid and methanol.	2.45	2	0	benzoate ester; methyl ester	insect attractant; metabolite
dihydrosafrole [no description available]	6.93	1	0	benzodioxoles
indene indene: structure in first source. 1H-indene : An ortho-fused bicyclic arene comprising of benzene and cyclopentene rings.	2.03	1	0	indene; ortho-fused bicyclic arene
benzotriazole benzotriazole: inhibitor of atmospheric metal corrosion; also component of motion picture film & Neva brake fluid. benzotriazole : The simplest member of the class of benzotriazoles that consists of a benzene nucleus fused to a 1H-1,2,3-triazole ring.	7.08	1	0	benzotriazoles	environmental contaminant; xenobiotic
benzothiophene [no description available]	2.31	1	0	1-benzothiophenes; benzothiophene
2-xylene 2-xylene: RN given refers to parent cpd. o-xylene : A xylene substituted by methyl groups at positions 1 and 2.	2.44	2	0	xylene
dilactide dilactide: structure given in first source	2.08	1	0	dioxanes
styrene oxide styrene oxide: structure. styrene oxide : An epoxide that is oxirane in which one of the hydrogens has been replaced by a phenyl group.	1.99	1	0	epoxide	human xenobiotic metabolite
3-methylpentane 3-methylpentane : An alkane that is pentane which is substituted by a methyl group at position 3. It is used as a solvent in organic synthesis, as a lubricant and as a raw material for producing carbon black.	2.46	2	0	alkane; volatile organic compound	allelochemical; human metabolite; non-polar solvent
methyl acrylate [no description available]	2.73	3	0	enoate ester
methylcyclopentane methylcyclopentane: toxic; RN 96-37-7. methylcyclopentane : A cycloalkane that is cyclopentane substituted by a single methyl group.	2.04	1	0	cycloalkane; volatile organic compound	human metabolite; plant metabolite
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.	2.1	1	0	aldehyde; furans	Maillard reaction product; metabolite
benzenesulfonamide [no description available]	1.96	1	0	sulfonamide
butylphen butylphen: irritant; structure. 4-tert-butylphenol : A member of the class of phenols that is phenol substituted with a tert-butyl group at position 4.	7.03	1	0	phenols	allergen
4-chloro-alpha,alpha,alpha-trifluorotoluene 4-chloro-alpha,alpha,alpha-trifluorotoluene: RN given refers to cpd with specified locants for chloride & trifluoromethyl moieties; structure given in first source	2.04	1	0
nitrobenzene nitrobenzene : A nitroarene consisting of benzene carrying a single nitro substituent. An industrial chemical used widely in the production of aniline.	1.96	1	0	nitroarene; nitrobenzenes
3-nitrotoluene [no description available]	1.96	1	0	mononitrotoluene
trehalose alpha,alpha-trehalose : A trehalose in which both glucose residues have alpha-configuration at the anomeric carbon.	3	4	0	trehalose	Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
dicloran 2,6-dichloro-4-nitroaniline : A nitroaniline that is 4-nitroaniline in which the hydrogens at positions 2 and 6 are replaced by chlorines. An agricultural fungicide, it is not approved for use in the European Union.	1.99	1	0	aromatic fungicide; dichlorobenzene; nitroaniline	antifungal agrochemical
carvone carvone: an oxidized derivative of limonene; RN given refers to cpd without isomeric designation; L-carvone has spearmint flavor, D-carvone has dill/caraway flavor. carvone : A p-menthane monoterpenoid that consists of cyclohex-2-enone having methyl and isopropenyl substituents at positions 2 and 5, respectively.	2.15	1	0	botanical anti-fungal agent; carvones	allergen
3-dinitrobenzene dinitrobenzene : Any member of the class of nitrobenzenes that consists of a benzene ring substituted by two nitro groups. A closed class.. 1,3-dinitrobenzene : A dinitrobenzene that is benzene disubstituted at positions 1 and 3 with nitro groups.	1.96	1	0	dinitrobenzene	neurotoxin
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.	8.95	3	0	benzenedicarboxylic acid
ethylbenzene [no description available]	2.06	1	0	alkylbenzene
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.	5.16	14	0	styrenes; vinylarene; volatile organic compound	mouse metabolite; mutagen; plant metabolite
cyclohexylmethanol cyclohexylmethanol: structure	2.03	1	0
phenylhydrazine [no description available]	1.96	1	0	phenylhydrazines	xenobiotic
anisole anisole : A monomethoxybenzene that is benzene substituted by a methoxy group.	1.96	1	0	monomethoxybenzene	plant metabolite
methylphenylsulfide thioanisole : An aryl sulfide that is thiophenol in which the hydrogen of the thiol group has been replaced by a methyl group.	1.96	1	0	aryl sulfide; benzenes
phenyl ether diphenyl ether : An aromatic ether in which the oxygen is attached to two phenyl substituents. It has been found in muscat grapes and vanilla.	2.02	1	0	aromatic ether	plant metabolite
boric acid [no description available]	2.53	2	0	boric acids	astringent
n-propylbenzene n-propylbenzene: RN given refers to parent cpd. propylbenzene : An alkylbenzene that is benzene having one of its aromatic hydrogens substituted by a propyl group.	1.93	1	0	alkylbenzene
2-ethylhexanol [no description available]	2.03	1	0	primary alcohol	plant metabolite; volatile oil component
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.	4.97	2	1	caprolactams	human blood serum metabolite
4-xylene p-xylene : A xylene with methyl groups at positions 1 and 4.	2.48	2	0	xylene
glycidyl methacrylate glycidyl methacrylate: RN given refers to monomer. glycidyl methacrylate : An enoate ester obtained by formal condensation of the carboxy group of methacrylic acid with the hydroxy group of glycidol.	2.75	3	0	enoate ester; epoxide
ethylene dibromide Ethylene Dibromide: An effective soil fumigant, insecticide, and nematocide. In humans, it causes severe burning of skin and irritation of the eyes and respiratory tract. Prolonged inhalation may cause liver necrosis. It is also used in gasoline. Members of this group have caused liver and lung cancers in rodents. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), 1,2-dibromoethane may reasonably be anticipated to be a carcinogen.. 1,2-dibromoethane : A bromoalkane that is ethane carrying bromo substituents at positions 1 and 2. It is produced by marine algae.	6.94	1	0	bromoalkane; bromohydrocarbon	algal metabolite; carcinogenic agent; fumigant; marine metabolite; mouse metabolite; mutagen
butane butane : A straight chain alkane composed of 4 carbon atoms.	2.94	4	0	alkane; gas molecular entity	food propellant; refrigerant
1-butene but-1-ene : A butene with unsaturation at position 1.	3.5	8	0	butene
1,3-butadiene buta-1,3-diene : A butadiene with unsaturation at positions 1 and 3.	3.96	13	0	butadiene	carcinogenic agent; mutagen
acrolein [no description available]	2.43	2	0	enal	herbicide; human xenobiotic metabolite; toxin
propylamine propylamine : A member of the class of alkylamines that is propane substituted by an amino group at C-1.	1.96	1	0	alkylamines
acrylonitrile [no description available]	8.22	6	0	aliphatic nitrile; volatile organic compound	antifungal agent; carcinogenic agent; fungal metabolite; mutagen; polar aprotic solvent
propargyl alcohol propargyl alcohol: irreversibly inactivates alcohol oxidase; RN given refers to parent cpd. prop-2-yn-1-ol : A terminal acetylenic compound that is prop-2-yne substituted by a hydroxy group at position 1.	2.03	1	0	propynol; terminal acetylenic compound; volatile organic compound	antifungal agent; Saccharomyces cerevisiae metabolite
glyoxal [no description available]	7.41	1	0	dialdehyde	agrochemical; allergen; pesticide; plant growth regulator
methyl formate methyl formate: RN given refers to parent cpd. methyl formate : A formate ester resulting from the formal condensation of formic acid with methanol. A low-boiling (31.5 degreeC) colourless, flammable liquid, it has been used as a fumigant and larvicide for tobacco and food crops.	2.03	1	0	formate ester; methyl ester; volatile organic compound	fumigant; insecticide; polar aprotic solvent; refrigerant
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	2.04	1	0	alkane
isoamylamine isoamylamine: RN given refers to parent cpd. isopentylamine : A primary aliphatic amine that is butan-1-amine carrying a methyl substituent at position 3.	2.01	1	0	primary aliphatic amine	bacterial metabolite; plant metabolite
3-hydroxybutanal [no description available]	3.59	2	0
vinyl acetate [no description available]	5.05	12	0	acetate ester
maleic anhydride Maleic Anhydrides: Used in copolymerization reactions, in the Diels-Alder(diene)synthesis, in the preparation of resins, pharmaceuticals and agricultural chemicals. It is a powerful irritant and causes burns.. maleic anhydride : A cyclic dicarboxylic anhydride that is the cyclic anhydride of maleic acid.	2.98	4	0	cyclic dicarboxylic anhydride; furans	allergen
3-chloroaniline 3-chloroaniline: RN given refers to parent cpd	1.96	1	0
melamine melamine: RN given refers to parent cpd; structure. melamine : A trimer of cyanamide, with a 1,3,5-triazine skeleton.	2.84	4	0	triamino-1,3,5-triazine	xenobiotic metabolite
bromobenzene [no description available]	1.96	1	0	bromoarene; bromobenzenes; volatile organic compound	hepatotoxic agent; mouse metabolite; non-polar solvent
chlorobenzene [no description available]	3.8	3	0	monochlorobenzenes	solvent
cyclohexanol Cyclohexanols: Monohydroxy derivatives of cyclohexanes that contain the general formula R-C6H11O. They have a camphorlike odor and are used in making soaps, insecticides, germicides, dry cleaning, and plasticizers.. cyclohexanols : An alcohol in which one or more hydroxy groups are attached to a cyclohexane skeleton.	2.03	1	0	cyclohexanols; secondary alcohol	solvent
thiophenol thiophenol : A thiol in which the sulfanyl group is attached to a phenyl group.	1.96	1	0	aryl thiol
triethylene glycol dimethacrylate [no description available]	2.05	1	0
propyl acetate propyl acetate: affects aggression without affecting motor activity; RN given refers to parent cpd. propyl acetate : An acetate ester obtained by the formal condensation of acetic acid with propanol.	2.02	1	0	acetate ester	fragrance; plant metabolite
pentane Pentanes: Five-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives.. pentane : A straight chain alkane consisting of 5 carbon atoms.	3.45	7	0	alkane; volatile organic compound	non-polar solvent; refrigerant
1-pentene 1-pentene: structure in first source	2.1	1	0
allyl cyanide TL 350: structure given in first source. allyl cyanide : An aliphatic nitrile that is hydrogen cyanide in which the hydrogen has been replaced by an allyl group.	2.1	1	0	aliphatic nitrile; olefinic compound	antifeedant; neurotoxin; plant metabolite
dicyanmethane malononitrile : A dinitrile that is methane substituted by two cyano groups.	3.41	1	0	aliphatic nitrile; dinitrile
hydracrylonitrile hydracrylonitrile: structure	1.93	1	0
ethyl vinyl ether ethyl vinyl ether: structure	1.96	1	0
vinyl ether vinyl ether: major descriptor (65-85); on-line search VINYL COMPOUNDS (66-85); Index Medicus search VINYL ETHER (65-85)	1.94	1	0	ether
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.	3.41	7	0	pyrrole; secondary amine
tetrahydrofuran oxolane : A cyclic ether that is butane in which one hydrogen from each methyl group is substituted by an oxygen.	7.02	1	0	cyclic ether; oxolanes; saturated organic heteromonocyclic parent; volatile organic compound	polar aprotic solvent
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	6.23	10	1	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
isopropyl myristate isopropyl myristate: used for microemulsions; structure	4.61	1	1	fatty acid ester
n-hexane hexane : An unbranched alkane containing six carbon atoms.	2.04	1	0	alkane; volatile organic compound	neurotoxin; non-polar solvent
1,4-butanediol butane-1,4-diol : A butanediol that is butane in which one hydrogen of each of the methyl groups is substituted by a hydroxy group. A colourless, water-miscible, viscous liquid at room temperature (m.p. 16degreeC) with a high boiling point (230degreeC), it is mainly used for the production of other organic chemicals, particularly the solvent oxolane (also known as tetrahydrofuran or THF).	2.05	1	0	butanediol; glycol	neurotoxin; prodrug; protic solvent
2-ethoxyethanol 2-ethoxyethanol : A hydroxyether that is the ethyl ether derivative of ethylene glycol.	1.96	1	0	glycol ether; primary alcohol	protic solvent; teratogenic agent
cyclohexane Cyclohexane: C6H12. cyclohexane : An alicyclic hydrocarbon comprising a ring of six carbon atoms; the cyclic form of hexane, used as a raw material in the manufacture of nylon.	2.76	3	0	cycloalkane; volatile organic compound	non-polar solvent
cyclohexene cyclohexene : A cycloalkene that is cylohexane with a single double bond.	2.07	1	0	cycloalkene
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.	3.55	8	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.	3.82	3	0	hydroxyether
1-octene 1-octene: RN given refers to parent cpd. 1-octene : An octene with an unsaturation C-1.	3.06	4	0	octene
propylene propylene: structure	7.6	75	0	alkene; gas molecular entity	refrigerant; xenobiotic
dimethyl ether dimethyl ether : An ether in which the oxygen atom is connected to two methyl groups.	2.71	3	0	ether
isobutylene 2-methylprop-1-ene : An alkene that is prop-1-ene substituted by a methyl group at position 2.	2.65	3	0	alkene; gas molecular entity
2,2,2-trichloroethanol [no description available]	1.96	1	0	chloroethanol	mouse metabolite
tetrafluoroethylene tetrafluoroethylene: RN given refers to parent cpd; structure	7.72	3	0	fluorocarbon
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.	2.39	2	0	diester; phthalate ester	androstane receptor agonist; apoptosis inhibitor; plasticiser
trinitrotoluene Trinitrotoluene: A 2,4,6-trinitrotoluene, which is an explosive chemical that can cause skin irritation and other toxic consequences.. 2,4,6-trinitrotoluene : A trinitrotoluene having the nitro groups at positions 2, 4 and 6.	1.92	1	0	trinitrotoluene	explosive
tetralin tetralin: structure given in first source. tetralin : An ortho-fused bicyclic hydrocarbon that is 1,2,3,4-tetrahydro derivative of naphthalene.	2.15	1	0	ortho-fused bicyclic hydrocarbon; tetralins
anthracene acene : A polycyclic aromatic hydrocarbon consisting of fused benzene rings in a rectilinear arrangement.. acenes : Polycyclic aromatic hydrocarbons consisting of fused benzene rings in a rectilinear arrangement and their substitution derivatives.	7.91	4	0	acene; anthracenes; ortho-fused tricyclic hydrocarbon
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.	2.1	1	0	diester; methyl ester; phthalate ester
sulfoxide sulfoxide: synergistic insecticide for use with pyrethrum, allethrin, rotenone, ryania, etc.; RN given refers to parent cpd; structure. sulfoxide : An organosulfur compound having the structure R2S=O or R2C=S=O (R =/= H).	2.05	1	0	benzodioxoles
2,5-norbornadiene [no description available]	3.79	11	0
sulfan blue sulfan blue: widely used to visualize lymph vessels for lymphography; structure	2.03	1	0	organic molecular entity
alpha-naphthylphthalamic acid alpha-naphthylphthalamic acid: RN given refers to parent cpd; structure. naptalam : A dicarboxylic acid monoamide which results from addition of one equivalent of 1-naphthylamine to phthalic anhydride.	4.17	16	0	carboxylic acid; dicarboxylic acid monoamide; N-(1-naphthyl)carboxamide	herbicide
indolebutyric acid indolebutyric acid: RN given refers to parent cpd. indole-3-butyric acid : A indol-3-yl carboxylic acid that is butanoic acid carrying a 1H-indol-3-yl substituent at position 1.	3.12	5	0	indol-3-yl carboxylic acid	auxin; plant hormone; plant metabolite
1-naphthylamine 1-Naphthylamine: A suspected industrial carcinogen (and listed as such by OSHA). Its N-hydroxy metabolite is strongly carcinogenic and mutagenic.. naphthylamine : A primary arylamine that is naphthalene substituted by an amino group at unspecified position.. 1-naphthylamine : A naphthylamine that is naphthalene substituted by an amino group at position 1.	2.08	1	0	naphthylamine	human xenobiotic metabolite
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.	2.07	1	0	naphthol	antinematodal drug; genotoxin; human urinary metabolite; human xenobiotic metabolite; mouse metabolite; radical scavenger
estragole estragole : A phenylpropanoid that is chavicol in which the hydroxy group is replaced by a methoxy group.	2.11	1	0	alkenylbenzene; monomethoxybenzene; phenylpropanoid	carcinogenic agent; flavouring agent; genotoxin; insect attractant; plant metabolite
ethyl acrylate [no description available]	1.98	1	0	enoate ester
n-butyl acrylate butyl acrylate : An acrylate ester obtained by the formal condensation of the hydroxy group of butan-1-ol with the carboxy group of acrylic acid.	7.47	2	0	acrylate ester
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	2.42	2	0	acetate ester; ethyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; metabolite; polar aprotic solvent; Saccharomyces cerevisiae metabolite
2-hydroxypyridine hydroxypyridine : Any member of the class of pyridines with at least one hydroxy substituent.. pyridin-2-ol : A monohydroxypyridine that is pyridine substituted by a hydroxy group at position 2.	2.07	1	0	monohydroxypyridine	plant metabolite
hexanoic acid hexanoic acid : A C6, straight-chain saturated fatty acid.	2.06	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	human metabolite; plant metabolite
iminodiacetic acid iminodiacetic acid: used as hepatobiliary imaging agent when labeled with Tc; RN given refers to parent cpd; structure. iminodiacetic acid : An amino dicarboxylic acid that is glycine in which one of the hydrogens attached to the nitrogen is substituted by a carboxymethyl group.	6.92	1	0	amino dicarboxylic acid; glycine derivative; non-proteinogenic alpha-amino acid	chelator
n-heptane Heptanes: Seven-carbon alkanes with the formula C7H16.. heptane : A straight-chain alkane with seven carbon atoms. It has been found in Jeffrey pine (Pinus jeffreyi).	2.04	1	0	alkane; volatile organic compound	non-polar solvent; plant metabolite
decylamine decylamine: structure	2.07	1	0	alkylamine
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.	2.42	2	0	cyanide salt; one-carbon compound; sodium salt	EC 1.15.1.1 (superoxide dismutase) inhibitor
ditiocarb Ditiocarb: A chelating agent that has been used to mobilize toxic metals from the tissues of humans and experimental animals. It is the main metabolite of DISULFIRAM.. diethyldithiocarbamic acid : A member of the class of dithiocarbamic acids that is diethylcarbamic acid in which both of the oxygens are replaced by sulfur.	1.96	1	0	dithiocarbamic acids	chelator; copper chelator
potassium cyanide [no description available]	2.44	2	0	cyanide salt; one-carbon compound; potassium salt	EC 1.15.1.1 (superoxide dismutase) inhibitor; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; neurotoxin
aziridine [no description available]	3.43	8	0	azacycloalkane; aziridines; saturated organic heteromonocyclic parent	alkylating agent
cycloguanil cycloguanil: the active metabolite of proguanil; antifolate drug; structure in first source. cycloguanil : A triazine in which a 1,6-dihydro-1,3,5-triazine ring is substituted at N-1 by a 4-chlorophenyl group, at C-2 and -4 by amino groups and at C-6 by gem-dimethyl groups. A dihydrofolate reductase inhibitor, it is a metabolite of the antimalarial drug proguanil.	1.96	1	0	triazines	antifolate; antiinfective agent; antimalarial; antiparasitic agent; antiprotozoal drug; EC 1.5.1.3 (dihydrofolate reductase) inhibitor
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.	2.6	1	0	catechin	antioxidant; plant metabolite
coronene coronene: structure. coronene : A ortho- and peri-fused polycyclic arene that consists of six peri-fused benzene rings.	2.05	1	0	ortho- and peri-fused polycyclic arene
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.	2.76	3	0	ortho- and peri-fused polycyclic arene; perylenes
quinazolines Quinazolines: A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.. quinazoline : A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.. quinazolines : Any organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.	2.1	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
acridines Acridines: Compounds that include the structure of acridine.. acridine : A polycyclic heteroarene that is anthracene in which one of the central CH groups is replaced by a nitrogen atom.	2.37	2	0	acridines; mancude organic heterotricyclic parent; polycyclic heteroarene	genotoxin
benzoxazoles 1,3-benzoxazole : A benzoxazole in which the benzene ring is fused to a 1,3-oxazole ring across positions 4 and 5.. benzoxazole : Compounds based on a fused 1,2- or 1,3-oxazole and benzene bicyclic ring skeleton.	4.61	1	1	1,3-benzoxazoles; mancude organic heterobicyclic parent
triethylenediamine triethylenediamine: RN given refers to parent cpd. triethylenediamine : An organic heterobicylic compound that is piperazine with an ethane-1,2-diyl group forming a bridge between N1 and N4. It is typically used as a catalyst in polymerization reactions.	1.99	1	0	bridged compound; diamine; saturated organic heterobicyclic parent; tertiary amino compound	antioxidant; catalyst; reagent
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	12.5	630	0	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
oxazoles Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.	2.49	2	0	1,3-oxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiazoles [no description available]	7.71	28	1	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.	7.07	1	0	diazine; pyrimidines	Daphnia magna metabolite
pyrazines Pyrazines: A heterocyclic aromatic organic compound with the chemical formula C4H4N2.. pyrazine : A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms.	2.02	1	0	diazine; pyrazines	Daphnia magna metabolite
thiocyanate thiocyanate: RN given refers to parent cpd. thiocyanate : A pseudohalide anion obtained by deprotonation of the thiol group of thiocyanic acid.	2.01	1	0	pseudohalide anion; sulfur molecular entity	human metabolite
pentamine pentamine: RN given refers to parent cpd; structure in Merck	2.13	1	0
perfluorodecalin perfluorodecalin: RN given refers to parent cpd without isomeric designation. perfluorodecalin : A fluorocarbon that is decalin in which every hydrogen is replaced by fluorine. Capable of dissolving large quantities of oxygen, it has been used as the basis of an artificial blood substitute.	2.1	1	0	fluorocarbon	blood substitute; solvent
azacitidine Azacitidine: A pyrimidine analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent.. 5-azacytidine : An N-glycosyl-1,3,5-triazine that is 4-amino-1,3,5-triazin-2(1H)-one substituted by a beta-D-ribofuranosyl residue via an N-glycosidic linkage. An antineoplastic agent, it is used in the treatment of myeloid leukaemia.	2.08	1	0	N-glycosyl-1,3,5-triazine; nucleoside analogue	antineoplastic agent
perfluorooctanoic acid perfluorooctanoic acid: RN given refers to parent cpd. perfluorooctanoic acid : A fluoroalkanoic acid that is perfluorinated octanoic acid.	2.6	1	0	fluoroalkanoic acid	carcinogenic agent; endocrine disruptor; environmental contaminant; surfactant; xenobiotic
diethyl sulfide ethyl sulfide : An aliphatic sulfide in which the sulfur atom is bonded to at least one ethyl group.. diethyl sulfide : An ethyl sulfide compound having two ethyl groups attached to a sulfur atom.	1.96	1	0	ethyl sulfide
2-fluoroethanol [no description available]	1.96	1	0
fluroxene fluroxene: was heading 1973-94; use ETHERS to search FLUROXENE 1973-94	2.34	2	0	organofluorine compound
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.	2.46	2	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.	2.05	1	0	dinitrile; pseudohalogen
fluorobenzenes Fluorobenzenes: Derivatives of BENZENE that contain FLUORINE.. monofluorobenzene : The simplest member of the class of monofluorobenzenes that is benzene carrying a single fluoro substituent.. fluorobenzenes : Any fluoroarene that is a benzene or a substituted benzene carrying at least one fluoro group.	2.39	2	0	monofluorobenzenes	NMR chemical shift reference compound
propadiene [no description available]	1.96	1	0	allenes
ketene ketene: structure. ketene : Carbonyl compounds where the C=O bond is conjugated to an alkylidene group.	2.98	4	0	ketene
glycyrrhetinic acid [no description available]	2.04	1	0	cyclic terpene ketone; hydroxy monocarboxylic acid; pentacyclic triterpenoid	immunomodulator; plant metabolite
cdta CDTA: RN given refers to parent cpd; structure	1.99	1	0	organooxygen compound
dithiol dithiol: structure	7.03	1	0
sodium carbonate sodium carbonate: used topically for dermatitides, mouthwash, vaginal douche; veterinary use as emergency emetic; RN given refers to carbonic acid, di-Na salt; structure	2.03	1	0	carbonate salt; organic sodium salt
2-norbornene norbornene : A bridged compound that is cyclohexane with a methylene bridge between carbons 1 and 4 and a double bond at position 2.	2.88	3	0
carvacrol carvacrol : A phenol that is a natural monoterpene derivative of cymene. An inhibitor of bacterial growth, it is used as a food additive. Potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1).	2.07	1	0	botanical anti-fungal agent; p-menthane monoterpenoid; phenols	agrochemical; antimicrobial agent; flavouring agent; TRPA1 channel agonist; volatile oil component
2,4-pyridinedicarboxylic acid lutidinic acid : A pyridinedicarboxylic acid carrying carboxy groups at positions 2 and 4.	2.05	1	0	pyridinedicarboxylic acid
cycloheptanone cycloheptanone: structure	2.21	1	0
dimethylacetylene dimethylacetylene: structure in source	3.5	2	0
alpha-aminopyridine alpha-aminopyridine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #485. aminopyridine : Compounds containing a pyridine skeleton substituted by one or more amine groups.	7.05	1	0
hesperidin Hesperidin: A flavanone glycoside found in CITRUS fruit peels.. hesperidin : A disaccharide derivative that consists of hesperetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.31	1	0	3'-hydroxyflavanones; 4'-methoxyflavanones; dihydroxyflavanone; disaccharide derivative; flavanone glycoside; monomethoxyflavanone; rutinoside	mutagen
tropolone Tropolone: A seven-membered aromatic ring compound. It is structurally related to a number of naturally occurring antifungal compounds (ANTIFUNGAL AGENTS).. tropolone : A cyclic ketone that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2. It is a toxin produced by the agricultural pathogen Burkholderia plantarii.	2.02	1	0	alpha-hydroxy ketone; cyclic ketone; enol	bacterial metabolite; fungicide; toxin
phenylacetylene phenylacetylene: can polymerize into DENDRIMERS	2.07	1	0	benzenes
1,2-dichloroethylene 1,2-dichloroethylene: RN given refers to cpd without isomeric designation	8.94	12	0	chloroethenes
3-aminobutyric acid 3-aminobutyric acid: GABA uptake inhibitor. 3-aminobutanoic acid : A beta-amino acid that is butyric acid which is substituted by an amino group at position 3.	4.09	4	0	amino acid zwitterion; beta-amino acid; monocarboxylic acid	metabolite
maleimide [no description available]	2.08	1	0	dicarboximide; maleimides	EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
muscone muscone: structure in first source	4.61	1	1
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.	5.01	37	0	dialdehyde	biomarker
3-hexen-1-ol 3-hexen-1-ol: RN given refers to (Z)-isomer; a green odor chemical. hex-3-en-1-ol : A primary alcohol that is hex-3-ene substituted by a hydroxy group at position 1.	7.75	3	0	alkenyl alcohol; homoallylic alcohol; primary alcohol; volatile organic compound	plant metabolite
n-hexadecane n-hexadecane: structure. hexadecane : A straight-chain alkane with 16 carbon atoms. It is a component of essential oil isolated from long pepper.	2.02	1	0	long-chain alkane	non-polar solvent; plant metabolite; volatile oil component
4,4'-bipyridyl 4,4'-bipyridine : A bipyridine in which the two pyridine moieties are linked by a bond between positions C-4 and C-4'.	2.11	1	0	bipyridine
perfluorocyclopentene perfluorocyclopentene: structure in first source	3.15	1	0
chlorotrianisene Chlorotrianisene: A powerful synthetic, non-steroidal estrogen.	1.93	1	0	chloroalkene	antineoplastic agent; estrogen receptor modulator; xenoestrogen
3-hydroxyflavone 3-hydroxyflavone: structure given in first source. flavonol : A monohydroxyflavone that is the 3-hydroxy derivative of flavone.	3.05	4	0	flavonols; monohydroxyflavone
anatabine anatabine: alkaloid found in tobacco; structure	2.21	1	0	bipyridines
nitrosobenzene [no description available]	1.96	1	0	benzenes; nitroso compound	xenobiotic metabolite
diphenylamine Diphenylamine: In humans it may be irritating to mucous membranes. Methemoglobinemia has been produced experimentally. In veterinary use, it is one of active ingredients in topical agents for prevention and treatment of screwworm infestation. An indicator in tests for nitrate poisoning.. diphenylamine : An aromatic amine containing two phenyl substituents. It has been used as a fungicide for the treatment of superficial scald in apples and pears, but is no longer approved for this purpose within the European Union.	8.15	5	0	aromatic amine; bridged diphenyl fungicide; secondary amino compound	antifungal agrochemical; antioxidant; carotogenesis inhibitor; EC 1.3.99.29 [phytoene desaturase (zeta-carotene-forming)] inhibitor; ferroptosis inhibitor; radical scavenger
iodobenzene iodobenzene: RN given refers to unlabeled parent cpd	1.96	1	0
1-hexene 1-hexene: structure in first source. 1-hexene : An alkene that is hexane carrying a double bond at position 1.	3.56	8	0	alkene
fluoromethane fluoromethane: RN given refers to parent cpd. fluorocarbon : Compounds consisting wholly of fluorine and carbon.. fluoromethane : A member of the class of fluoromethanes that is methane in which a single hydrogen is substituted by a fluorine atom.	2.4	2	0	fluorohydrocarbon; fluoromethanes; methyl halides	refrigerant
vinyl bromide vinyl bromide: structure	1.96	1	0	bromoalkene; monohaloethene
1-methylcyclopropane 1-methylcyclopropane: do not confuse with MCP cpd (1-methylcyclopropene)	4.42	21	0
1,1-dimethylurea [no description available]	2.05	1	0
diisopropylnitrosamine [no description available]	1.96	1	0
triphenylphosphine triphenylphosphine: RN given refers to parent cpd. triphenylphosphine : A member of the class of tertiary phosphines that is phosphane in which the three hydrogens are replaced by phenyl groups.	2.47	2	0	benzenes; tertiary phosphine	NMR chemical shift reference compound; reducing agent
5-methylbenzimidazole 5-methylbenzimidazole: structure in first source. 5-methyl-1H-benzimidazole : A member of the class of imidazoles that is 1H-benzimidazole in which the hydrogen at position 5 is substituted by a methyl group.	2.13	1	0	imidazoles
2-hydrazinobenzothiazole [no description available]	2.13	1	0
methyl carbonate methyl carbonate: RN given refers to unlabeled parent cpd; structure. dimethyl carbonate : A carbonate ester that is carbonic acid in which both hydrogens are replaced by methyl groups. A flammable, colourless liquid (m.p. 2-4degreeC, b.p. 90degreeC) with a characterstic ester-like odour, it is used as a 'green' methylating agent and as a solvent.	7.17	1	0	carbonate ester	reagent; solvent
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	2.46	2	0	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
hexamethylene glycol hexane-1,6-diol : A diol that is hexane substituted by hydroxy groups at positions 1 and 6.	2.05	1	0	diol; primary alcohol
pentadecane pentadecane : A straight-chain alkane with 15 carbon atoms. It is a component of volatile oils isolated from plants species like Scandix balansae.	2.06	1	0	long-chain alkane	animal metabolite; plant metabolite; volatile oil component
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.	2.03	1	0
erythromycin Erythromycin: A bacteriostatic antibiotic macrolide produced by Streptomyces erythreus. Erythromycin A is considered its major active component. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins.. erythromycin : Any of several wide-spectrum macrolide antibiotics obtained from actinomycete Saccharopolyspora erythraea (formerly known as Streptomyces erythraeus).. erythromycin A : An erythromycin that consists of erythronolide A having 2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl and 3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl residues attahced at positions 4 and 6 respectively.	2.04	1	0	cyclic ketone; erythromycin
homoserine homoserine : An alpha-amino acid that is glycine substituted at the alpha-position by a 2-hydroxyethyl group.. L-homoserine : The L-enantiomer of homoserine.	2.17	1	0	amino acid zwitterion; homoserine	algal metabolite; Escherichia coli metabolite; human metabolite; Saccharomyces cerevisiae metabolite
methylnitrosourea Methylnitrosourea: A nitrosourea compound with alkylating, carcinogenic, and mutagenic properties.. N-methyl-N-nitrosourea : A member of the class of N-nitrosoureas that is urea in which one of the nitrogens is substituted by methyl and nitroso groups.	1.96	1	0	N-nitrosoureas	alkylating agent; carcinogenic agent; mutagen; teratogenic agent
diphenyliodonium diphenyliodonium: RN given refers to the parent coumpound; inhibitor of neutrophil superoxide generating oxidase; structure has been determined	2.05	1	0
hydroxyethyl methacrylate hydroxyethyl methacrylate: many of cited refs are for gel which refers to polymeric form of above cpd: POLYHYDROXYETHYL METHACRYLATE. 2-hydroxyethyl methacrylate : An enoate ester that is the monomethacryloyl derivative of ethylene glycol.	1.98	1	0	enoate ester	allergen; polymerisation monomer
3,4-epoxy-1-butene 3,4-epoxy-1-butene: RN given refers to monomer	1.96	1	0
deoxycytidine [no description available]	4.61	1	1	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
chlormequat Chlormequat: A plant growth regulator that is commonly used on ornamental plants.. chlormequat : A quaternary ammonium ion that is choline in which the hydroxy group has been replaced by a chlorine. Its salts (particularly the chloride salt, known as chlormequat chloride) are used as plant growth retardants.	2.06	1	0	quaternary ammonium ion	plant growth retardant
methyl phenyl sulfoxide (methylsulfinyl)benzene : A sulfoxide resulting from the formal oxidation of the sulfur atom of thioanisole.	1.96	1	0	benzenes; sulfoxide
durapatite Durapatite: The mineral component of bones and teeth; it has been used therapeutically as a prosthetic aid and in the prevention and treatment of osteoporosis.. hydroxylapatite : A phosphate mineral with the formula Ca5(PO4)3(OH).	3.23	6	0
sodium hydroxide Sodium Hydroxide: A highly caustic substance that is used to neutralize acids and make sodium salts. (From Merck Index, 11th ed)	2.11	1	0	alkali metal hydroxide
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.	3.21	1	0	zinc molecular entity
beta-pinene beta-pinene: alpha-pinene is also available. beta-pinene : An isomer of pinene with an exocyclic double bond. It is a component of essential oils from many plants.	2.11	1	0	pinene	plant metabolite
vancomycin Vancomycin: Antibacterial obtained from Streptomyces orientalis. It is a glycopeptide related to RISTOCETIN that inhibits bacterial cell wall assembly and is toxic to kidneys and the inner ear.. vancomycin : A complex glycopeptide from Streptomyces orientalis. It inhibits a specific step in the synthesis of the peptidoglycan layer in the Gram-positive bacteria Staphylococcus aureus and Clostridium difficile.	1.98	1	0	glycopeptide	antibacterial drug; antimicrobial agent; bacterial metabolite
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.	3.25	6	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
tocopherols [no description available]	4.1	4	0
1,2-epoxyhexane [no description available]	4.61	1	1
selenomethionine [no description available]	2.71	3	0	selenoamino acid; selenomethionines	plant metabolite
1,3-xylenediamine 1,3-xylenediamine: structure given in first source	2.21	1	0
bisphenol a-glycidyl methacrylate Bisphenol A-Glycidyl Methacrylate: The reaction product of bisphenol A and glycidyl methacrylate that undergoes polymerization when exposed to ultraviolet light or mixed with a catalyst. It is used as a bond implant material and as the resin component of dental sealants and composite restorative materials.	2.05	1	0	diarylmethane
methyl tert-butyl ether methyl tert-butyl ether: used to dissolve gallstones; gasoline additive. methyl tert-butyl ether : An ether having methyl and tert-butyl as the two alkyl components.	2.43	2	0	ether	fuel additive; metabolite; non-polar solvent
bromoxynil bromoxynil: RN given refers to parent cpd; structure. 3,5-dibromo-4-hydroxybenzonitrile : A dibromobenzene that is 2,6-dibromophenol substituted by a cyano group at position 4.	2.02	1	0	dibromobenzene; hydroxynitrile; phenols	environmental contaminant; herbicide; xenobiotic
2,5-dihydrofuran 2,5-dihydrofuran: structure in first source	1.96	1	0
decane decane : A straight-chain alkane with 10 carbon atoms.	2.6	1	0	alkane
cyclopropanecarboxylic acid cyclopropanecarboxylic acid: 0	2.47	2	0	cyclopropanes; monocarboxylic acid
paraquat Paraquat: A poisonous dipyridilium compound used as contact herbicide. Contact with concentrated solutions causes irritation of the skin, cracking and shedding of the nails, and delayed healing of cuts and wounds.. paraquat : An organic cation that consists of 4,4'-bipyridine bearing two N-methyl substituents loctated at the 1- and 1'-positions.	3.96	13	0	organic cation	geroprotector; herbicide
tetrabutylammonium tetrabutylammonium: lipophilic probe; RN given refers to parent cpd	2.03	1	0	quaternary ammonium ion
azetidyl-2-carboxylic acid azetidyl-2-carboxylic acid: a proline analog (with 4-membered ring in place of 5); a toxic non-protein amino acid that is misincorporated into protein in place of proline; induces nonfunctional heat-shock proteins; inhibits acquired thermotolerance; RN given refers to (L)-isomer; found in beets and Liliaceae. (S)-azetidine-2-carboxylic acid : The (S)-enantiomer of azetidine-2-carboxylic acid.. azetidinecarboxylic acid : A member of the class of azetidines that is azetidine substituted by at least one carboxy group at unspecified position.	4.35	3	0	azetidine-2-carboxylic acid
2,4-diacetylphloroglucinol 2,4-diacetylphloroglucinol: produced by Pseudomonas aurantiaca. 2,4-diacetylphloroglucinol : A benzenetriol that is phloroglucinol in which two of the ring hydrogens are replaced by acetyl groups.	2.01	1	0	aromatic ketone; benzenetriol; diketone; methyl ketone	antifungal agent; bacterial metabolite
diallyl disulfide diallyl disulfide: major constituent of garlic oil. diallyl disulfide : An organic disulfide where the organic group specified is allyl. It has been isolated from garlic and other species of the genus Allium.	2.08	1	0	organic disulfide	antifungal agent; antineoplastic agent; plant metabolite
1,3,5-hexatriene 1,3,5-hexatriene: structure in first source	2.08	1	0
phenethyl isothiocyanate phenethyl isothiocyanate: a dietary liver aldehyde dehydrogenase inhibitor; promotes urinary bladder carcinoma. phenethyl isothiocyanate : An isothiocyanate having a phenethyl group attached to the nitrogen. It is a naturally occurring compound found in some cruciferous vegetables (e.g. watercress) and is known to possess anticancer properties.	2.15	1	0	isothiocyanate	antineoplastic agent; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; 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.	2.03	1	0	2-benzofurans; gamma-lactone; organic heteropentacyclic compound; oxaspiro compound; polyphenol; xanthene dye	fluorescent dye; radioopaque medium
benzyl acetone benzyl acetone: a dominant floral attractant	2.07	1	0	ketone
sulfur hexafluoride Sulfur Hexafluoride: Sulfur hexafluoride. An inert gas used mainly as a test gas in respiratory physiology. Other uses include its injection in vitreoretinal surgery to restore the vitreous chamber and as a tracer in monitoring the dispersion and deposition of air pollutants.. sulfur hexafluoride : A sulfur coordination entity consisting of six fluorine atoms attached to a central sulfur atom. It is the most potent greenhouse gas currently known, with a global warming potential of 23,900 times that of CO2 over a 100 year period (SF6 has an estimated lifetime in the atmosphere of between 800 and 3,000 years).	2.04	1	0	sulfur coordination entity	greenhouse gas; NMR chemical shift reference compound; ultrasound contrast agent
1,2-benzisothiazoline-3-one 1,2-benzisothiazoline-3-one: a preservative in water-based solutions such as paints, cutting fluids, printing inks, cleaning agents, polyvinyl chloride gloves, etc.. benzo[d]isothiazol-3-one : An organic heterobicyclic compound based on a fused 1,2-thiazole and benzene bicyclic ring skeleton, with the S atom positioned adjacent to one of the positions of ring fusion.	2.05	1	0	organic heterobicyclic compound; organonitrogen heterocyclic compound	disinfectant; drug allergen; environmental contaminant; platelet aggregation inhibitor; sensitiser; xenobiotic
sulfuryl fluoride sulfuryl fluoride: fumigant	2.13	1	0	sulfuryl halide	fumigant insecticide
toliprolol toliprolol: was MH 1975-92 (see under PROPANOLAMINES 1981-90, was DOBEROL see under PROPANOLAMINES 1975-80); KOE 592 was see TOLIPROLOL 1975-92; use PROPANOLAMINES to search TOLIPROLOL 1975-92; beta adrenergic blockader with some stimulant action; it has been proposed for angina pectoris	2.04	1	0	aromatic ether
uridine diphosphate galactose Uridine Diphosphate Galactose: A nucleoside diphosphate sugar which can be epimerized into UDPglucose for entry into the mainstream of carbohydrate metabolism. Serves as a source of galactose in the synthesis of lipopolysaccharides, cerebrosides, and lactose.. UDP-alpha-D-galactose : A UDP-D-galactose in which the anomeric centre of the galactose moiety has alpha-configuration.	2.02	1	0	UDP-D-galactose	mouse metabolite
dicloxacillin Dicloxacillin: One of the PENICILLINS which is resistant to PENICILLINASE.. dicloxacillin : A penicillin that is 6-aminopenicillanic acid in which one of the amino hydrogens is replaced by a 3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]formyl group.	2.04	1	0	dichlorobenzene; penicillin	antibacterial drug
methional [no description available]	2.89	4	0	aliphatic sulfide	prostaglandin antagonist
2,2-bis(bromomethyl)-1,3-propanediol 2,2-bis(bromomethyl)-1,3-propanediol: structure given in first source	3.27	6	0	primary alcohol
mannose mannopyranose : The pyranose form of mannose.	2.44	2	0	D-aldohexose; D-mannose; mannopyranose	metabolite
carbonates Carbonates: Salts or ions of the theoretical carbonic acid, containing the radical CO2(3-). Carbonates are readily decomposed by acids. The carbonates of the alkali metals are water-soluble; all others are insoluble. (From Grant & Hackh's Chemical Dictionary, 5th ed). carbonates : Organooxygen compounds that are salts or esters of carbonic acid, H2CO3.	3.3	6	0	carbon oxoanion
4,6-diamino-2,2-dimethyl-1,2-dihydro-1-phenyl-s-triazine 4,6-diamino-2,2-dimethyl-1,2-dihydro-1-phenyl-s-triazine: structure in first source	1.96	1	0
buthionine sulfoximine Buthionine Sulfoximine: A synthetic amino acid that depletes glutathione by irreversibly inhibiting gamma-glutamylcysteine synthetase. Inhibition of this enzyme is a critical step in glutathione biosynthesis. It has been shown to inhibit the proliferative response in human T-lymphocytes and inhibit macrophage activation. (J Biol Chem 1995;270(33):1945-7). 2-amino-4-(S-butylsulfonimidoyl)butanoic acid : A non-proteinogenic alpha-amino acid that is homocysteine in which the thiol group carries an oxo, imino and butyl groups.. S-butyl-DL-homocysteine (S,R)-sulfoximine : A sulfoximide that is the sulfoximine derivative of an analogue of DL-methionine in which the S-methyl group is replaced by S-butyl.	2.08	1	0	diastereoisomeric mixture; homocysteines; non-proteinogenic alpha-amino acid; sulfoximide	EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor; ferroptosis inducer
octyl dodecanol octyl dodecanol: structure in first source	2.03	1	0
diaveridine diaveridine: RN given refers to parent cpd; structure. diaveridine : An aminopyrimidine in which the pyrimidine ring carries amino substituents at C-2 and C-4 and a 3,4-dimethoxybenzyl group at C-5. A folic acid antagonist, it is used as a synergist with sulfonamides against the parasitic Eimeria species.	1.96	1	0	aminopyrimidine	antiparasitic agent; drug allergen
limonene Limonene: A naturally-occurring class of MONOTERPENES which occur as a clear colorless liquid at room temperature. Limonene is the major component in the oil of oranges which has many uses, including as flavor and fragrance. It is recognized as safe in food by the Food and Drug Administration (FDA).. limonene : A monoterpene that is cyclohex-1-ene substituted by a methyl group at position 1 and a prop-1-en-2-yl group at position 4 respectively.	2.11	1	0	cycloalkene; p-menthadiene	human metabolite
ammonium nitrate ammonium nitrate: structure. ammonium nitrate : The ammonium salt of nitric acid.	2.1	1	0	ammonium salt; inorganic molecular entity; inorganic nitrate salt	explosive; fertilizer; oxidising agent
sodium metasilicate sodium metasilicate: RN given refers to silicic acid, di-Na salt. sodium silicate : An inorganic sodium salt having silicate as the counterion.	2.06	1	0	inorganic sodium salt
dysprosium Dysprosium: An element of the rare earth family that has the atomic symbol Dy, atomic number 66, and atomic weight 162.50. Dysprosium is a silvery metal used primarily in the form of various salts.	1.94	1	0	f-block element atom; lanthanoid atom
iridium Iridium: A metallic element with the atomic symbol Ir, atomic number 77, and atomic weight 192.22.	3.01	4	0	cobalt group element atom; platinum group metal atom
lanthanum [no description available]	8.38	7	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.	3.39	7	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.	8.14	5	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.	8.27	6	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.	2.37	2	0	f-block element atom; lanthanoid atom
neon Neon: A noble gas with the atomic symbol Ne, atomic number 10, and atomic weight 20.18. It is found in the earth's crust and atmosphere as an inert, odorless gas and is used in vacuum tubes and incandescent lamps.	1.93	1	0	monoatomic neon; noble gas atom; p-block element atom
niobium Niobium: A metal element atomic number 41, atomic weight 92.906, symbol Nb.	2.44	2	0	vanadium group element atom
osmium Osmium: A very hard, gray, toxic, and nearly infusible metal element, atomic number 76, atomic weight 190.2, symbol Os.	2.49	2	0	iron group element atom; platinum group metal 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.	6.16	23	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.	4.31	18	0	elemental platinum; nickel group element atom; platinum group metal atom
rhenium Rhenium: A metal, atomic number 75, atomic weight 186.207, symbol Re.	2.44	2	0	manganese group element atom
rhodium Rhodium: A hard and rare metal of the platinum group, atomic number 45, atomic weight 102.905, symbol Rh.. rhodium atom : A cobalt group element atom of atomic number 45.	3.47	7	0	cobalt group element 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.	8.77	10	0	iron group element atom; platinum group metal atom
samarium Samarium: An element of the rare earth family of metals. It has the atomic symbol Sm, atomic number 62, and atomic weight 150.36. The oxide is used in the control rods of some nuclear reactors.	2	1	0	f-block element atom; lanthanoid atom
scandium Scandium: An element of the rare earth family of metals. It has the atomic symbol Sc, atomic number 21, and atomic weight 45.	2.75	3	0	d-block element atom; rare earth metal atom; scandium group element 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.	7.25	30	1	copper group element atom; elemental silver	Escherichia coli metabolite
technetium Technetium: The first artificially produced element and a radioactive fission product of URANIUM. Technetium has the atomic symbol Tc, and atomic number 43. All technetium isotopes are radioactive. Technetium 99m (m=metastable) which is the decay product of Molybdenum 99, has a half-life of about 6 hours and is used diagnostically as a radioactive imaging agent. Technetium 99 which is a decay product of technetium 99m, has a half-life of 210,000 years.	3.38	1	1	manganese group element atom
thorium Thorium: A radioactive element of the actinide series of metals. It has an atomic symbol Th, atomic number 90, and atomic weight 232.04. It is used as fuel in nuclear reactors to produce fissionable uranium isotopes. Because of its radioopacity, various thorium compounds are used to facilitate visualization in roentgenography.	2.03	1	0	actinoid atom; f-block element atom
thulium Thulium: An element of the rare earth family of metals. It has the atomic symbol Tm, atomic number 69, and atomic weight 168.93.	4.61	1	1	f-block element atom; lanthanoid atom
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.	9.37	42	1	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.	2.45	2	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.	8.25	6	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.	5.98	31	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.	2.91	4	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.	4.95	11	0	chromium group element atom; metal allergen	micronutrient
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.	2.03	1	0	f-block element atom; lanthanoid atom
gadolinium Gadolinium: An element of the rare earth family of metals. It has the atomic symbol Gd, atomic number 64, and atomic weight 157.25. Its oxide is used in the control rods of some nuclear reactors.	2.37	2	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.	4.45	21	0	copper group element atom; elemental gold
helium Helium: A noble gas with the atomic symbol He, atomic number 2, and atomic weight 4.003. It is a colorless, odorless, tasteless gas that is not combustible and does not support combustion. It was first detected in the sun and is now obtained from natural gas. Medically it is used as a diluent for other gases, being especially useful with oxygen in the treatment of certain cases of respiratory obstruction, and as a vehicle for general anesthetics.	3.09	5	0	monoatomic helium; noble gas atom; s-block element atom	food packaging gas
uranium Uranium: A radioactive element of the actinide series of metals. It has an atomic symbol U, atomic number 92, and atomic weight 238.03. U-235 is used as the fissionable fuel in nuclear weapons and as fuel in nuclear power reactors.	5.17	3	1	actinoid atom; f-block element atom; monoatomic uranium
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.	7.97	4	0	elemental vanadium; vanadium group element atom	micronutrient
xenon Xenon: A noble gas with the atomic symbol Xe, atomic number 54, and atomic weight 131.30. It is found in the earth's atmosphere and has been used as an anesthetic.	2.63	3	0	monoatomic xenon; noble gas atom; p-block element 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.	2.37	2	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.	4.85	10	0	titanium group element atom
aluminum chloride Aluminum Chloride: A compound with the chemical formula AlCl3; the anhydrous salt is used as a catalyst in organic chemical synthesis, and hydrated salts are used topically as antiperspirants, and for the management of HYPERHYDROSIS.	2.45	2	0	aluminium coordination entity	Lewis acid
cupric chloride cupric chloride: RN given refers to unlabeled parent cpd. copper(II) chloride : An inorganic chloride of copper in which the metal is in the +2 oxidation state.	2.42	2	0	copper molecular entity; inorganic chloride	EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor
mercuric chloride Mercuric Chloride: Mercury chloride (HgCl2). A highly toxic compound that volatizes slightly at ordinary temperature and appreciably at 100 degrees C. It is corrosive to mucous membranes and used as a topical antiseptic and disinfectant.. mercury dichloride : A mercury coordination entity made up of linear triatomic molecules in which a mercury atom is bonded to two chlorines. Water-soluble, it is highly toxic. Once used in a wide variety of applications, including preserving wood and anatomical specimens, embalming and disinfecting, as an intensifier in photography, as a mordant for rabbit and beaver furs, and freeing gold from lead, its use has markedly declined as less toxic alternatives have been developed.	2.4	2	0	mercury coordination entity	sensitiser
titanium tetrachloride titanium tetrachloride: RN given refers to TiCl4	2.06	1	0
cesium chloride cesium chloride: RN given refers to unlabeled cpd. caesium chloride : The inorganic chloride salt of caesium; each caesium ion is coordinated by eight chlorine ions.	2.05	1	0	inorganic caesium salt; inorganic chloride	phase-transfer catalyst; vasoconstrictor agent
camptothecin NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source	2.01	1	0	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
ferric chloride ferric chloride: RN given refers to cpd with MF of Fe-Cl3; used to induce experimental arterial thrombosis to evaluate antithrombotic agents	2.01	1	0	iron coordination entity	astringent; Lewis acid
nickel chloride nickel chloride: RN given refers to cpd with MF of Ni-Cl2. nickel dichloride : A compound of nickel and chloride in which the ratio of nickel (in the +2 oxidation state) to chloride is 1:2.	2.05	1	0	nickel coordination entity	calcium channel blocker; hapten
ferrous sulfate ferrous sulfate: Ferro-Gradumet is ferrous sulfate in controlled release form; RN given refers to Fe(+2)[1:1] salt. iron(2+) sulfate (anhydrous) : A compound of iron and sulfate in which the ratio of iron(2+) to sulfate ions is 1:1. Various hydrates occur naturally - most commonly the heptahydrate, which loses water to form the tetrahydrate at 57degreeC and the monohydrate at 65degreeC.	2.68	3	0	iron molecular entity; metal sulfate	reducing agent
phosphine phosphane : The simplest phosphine, consisting of a single phosphorus atom with three hydrogens attached.. phosphine : Phosphane (PH3) and compounds derived from it by substituting one, two or three hydrogen atoms by hydrocarbyl groups: RPH2, R2PH, R3P (R =/= H) are called primary, secondary and tertiary phosphines, respectively. A specific phosphine is preferably named as a substituted phosphane.	4.54	7	0	mononuclear parent hydride; phosphanes; phosphine	carcinogenic agent; fumigant insecticide
isopentenyladenosine Isopentenyladenosine: N(6)-[delta(3)-isopentenyl]adenosine. Isopentenyl derivative of adenosine which is a member of the cytokinin family of plant growth regulators.. N(6)-(Delta(2)-isopentenyl)adenosine : A nucleoside analogue in which adenosine has been modified by substitution at the 6-amino nitrogen by a Delta(2)-isopentenyl group.	2.59	2	0	N-ribosyl-N(6)-isopentenyladenine; nucleoside analogue	antineoplastic agent; plant growth regulator; plant metabolite
bromine Bromine: A halogen with the atomic symbol Br, atomic number 35, and atomic weight 79.904. It is a volatile reddish-brown liquid that gives off suffocating vapors, is corrosive to the skin, and may cause severe gastroenteritis if ingested.	2.03	1	0	diatomic bromine
potassium nitrate potassium nitrate: RN given refers to cpd with MF of K-HNO3; when combined with charcoal and sulfur it can form EXPLOSIVE AGENTS. potassium nitrate : The inorganic nitrate salt of potassium.	2.44	2	0	inorganic nitrate salt; potassium salt	fertilizer
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.	2.25	1	0	calcium phosphate
copper sulfate Copper Sulfate: A sulfate salt of copper. It is a potent emetic and is used as an antidote for poisoning by phosphorus. It also can be used to prevent the growth of algae.. copper(II) sulfate : A metal sulfate compound having copper(2+) as the metal ion.	3.41	7	0	metal sulfate	emetic; fertilizer; sensitiser
tungstate [no description available]	2	1	0	divalent inorganic anion; tungsten oxoanion
silver nitrate Silver Nitrate: A silver salt with powerful germicidal activity. It has been used topically to prevent OPHTHALMIA NEONATORUM.	4.78	31	0	inorganic nitrate salt; silver salt	astringent
chloroethylene oxide chloroethylene oxide: postulated metabolite of vinyl chloride; structure	2.01	1	0	organochlorine compound
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	3.27	6	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.	2.73	3	0	diatomic fluorine; gas molecular entity	NMR chemical shift reference compound
chlorine Chlorine: An element with atomic symbol Cl, atomic number 17, and atomic weight 35, and member of the halogen family.	11.03	35	0	diatomic chlorine; gas molecular entity	bleaching agent
nitrous acid Nitrous Acid: Nitrous acid (HNO2). A weak acid that exists only in solution. It can form water-soluble nitrites and stable esters. (From Merck Index, 11th ed)	2.42	2	0	nitrogen oxoacid
bromine trifluoride bromine trifluoride: a nucleophilic fluorinating agent	2.15	1	0
galactose aldohexose : A hexose with a (potential) aldehyde group at one end.	5.44	4	1
poloxalene Poloxalene: A copolymer of polyethylene and polypropylene ether glycol. It is a non-ionic polyol surface-active agent used medically as a fecal softener and in cattle for prevention of bloat.. pluronic : A triblock copolymer composed of a central hydrophobic chain of poly(propylene oxide) flanked by two hydrophilic chains of poly(ethylene oxide).	1.98	1	0	epoxide
zirconium chloride zirconium tetrachloride : A zirconium coordination entity comprising four chlorine atoms bound to a central zirconium atom.	2.45	2	0	inorganic chloride; zirconium coordination entity	catalyst
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.	9.41	53	1	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
radon Radon: A naturally radioactive element with atomic symbol Rn, and atomic number 86. It is a member of the noble gas family found in soil, and is released during the decay of RADIUM.. radon(0) : A monoatomic radon that has an oxidation state of zero.	1.98	1	0	monoatomic radon; noble gas atom; p-block element atom
chlorine dioxide chlorine dioxide: equal or superior to chlorine when used as wastewater disinfectant	7.05	1	0	chlorine dioxide
sodium selenite disodium selenite : An inorganic sodium salt composed of sodium and selenite ions in a 2:1 ratio.	2.04	1	0	inorganic sodium salt; selenite salt	nutraceutical
cadmium sulfate cadmium sulfate: RN given refers to cpd with MF of Cd-H2SO4	2.73	3	0	cadmium salt
cobaltous nitrate cobaltous nitrate: RN given refers to Co(+2) salt. cobalt dinitrate : A cobalt salt in which the cobalt metal is in the +2 oxidation state and the counter-anion is nitrate.	2.03	1	0	cobalt salt; inorganic nitrate salt
nitrogen tetroxide nitrogen tetroxide: toxic irritant in rocket fuel; structure	7.33	2	0	nitrogen oxide	oxidising 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.	2.66	3	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.	11.11	22	0	titanium oxides	food colouring
sodium tungstate(vi) sodium tungstate(VI): inactivates molybdoenzymes in Anabaena; RN given refers to tungstic acid [H2WO4], di-Na salt. sodium tungstate : An inorganic sodium salt having tungstate as the counterion. Combines with hydrogen peroxide for the oxidation of secondary amines to nitrones.	2.46	2	0	inorganic sodium salt	reagent
salen disalicylaldehyde ethylenediamine: reagents for determination of iron	2.01	1	0
tiletamine hydrochloride Cyclohexanones: Cyclohexane ring substituted by one or more ketones in any position.. cyclohexanones : Any alicyclic ketone based on a cyclohexane skeleton and its substituted derivatives thereof.	2.07	1	0
n'-nitrosonornicotine N'-nitrosonornicotine: structure; a potent carcinogen in laboratory animals	2.03	1	0	pyridines; pyrrolidines
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	2.46	2	0	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
ethephon (2-chloroethyl)phosphonic acid: structure in first source. (2-chloroethyl)phosphonic acid : A phosphonic acid compound having a 2-chloroethyl substituent attached to the P-atom.	6	104	0	phosphonic acids	plant growth regulator
gold tetrachloride, acid gold tetrachloride, acid: used in root canal therapy; RN given refers to (SP-4-1)	2.05	1	0
fluorides [no description available]	4.68	9	0	halide anion; monoatomic fluorine
homocitric acid [no description available]	2	1	0	tricarboxylic acid
tomatine alpha-tomatine: in tomato fruits and vegetative plant tissues; structure in first source	2.05	1	0	alkaloid antibiotic; glycoalkaloid; glycoside; steroid alkaloid; tetrasaccharide derivative	antifungal agent; immunological adjuvant; phytotoxin
cresyl violet cresyl violet: RN given refers to chloride. cresyl violet : A cationic heterotetracyclic fluorescent dye derived from benzo[a]phenoxazine.	2.05	1	0
chromium chromium hexavalent ion: a human respiratory carcinogen	2.49	2	0	chromium cation; monoatomic hexacation
keracyanin cyanidin 3-rutinoside: an anthocyanin compound. cyanidin 3-O-rutinoside chloride : A member of the class of anthocyanin chlorides that has cyanidin 3-O-rutinoside as the cationic counterpart.	2.13	1	0	anthocyanin chlorides
oryzalin oryzalin: a dinitroaniline; preemergence herbicide; structure. oryzalin : A sulfonamide that is benzenesulfonamide substituted at positions 3 and 5 by nitro groups and at position 4 by a dipropylamino group.	2.74	3	0	aromatic amine; C-nitro compound; sulfonamide; tertiary amino compound	agrochemical; antimitotic; herbicide
iodine [no description available]	2.33	2	0	halide anion; monoatomic iodine	human metabolite
osmium tetroxide Osmium Tetroxide: (T-4)-Osmium oxide (OsO4). A highly toxic and volatile oxide of osmium used in industry as an oxidizing agent. It is also used as a histological fixative and stain and as a synovectomy agent in arthritic joints. Its vapor can cause eye, skin, and lung damage.. osmium tetroxide : An osmium coordination entity consisting of four oxygen atoms bound to a central osmium atom via covalent double bonds.	6.92	1	0	osmium coordination entity	fixative; histological dye; oxidising agent; poison
phosphotyrosine Phosphotyrosine: An amino acid that occurs in endogenous proteins. Tyrosine phosphorylation and dephosphorylation plays a role in cellular signal transduction and possibly in cell growth control and carcinogenesis.. O(4)-phospho-L-tyrosine : A non-proteinogenic L-alpha-amino acid that is L-tyrosine phosphorylated at the phenolic hydroxy group.	2	1	0	L-tyrosine derivative; non-proteinogenic L-alpha-amino acid; O(4)-phosphotyrosine	Escherichia coli metabolite; immunogen
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.	8.3	149	0	benzenes; phenyl acetates
2,5-dimethylpyrazine [no description available]	2.02	1	0	pyrazines
pyrrolidine [no description available]	2.05	1	0	azacycloalkane; pyrrolidines; saturated organic heteromonocyclic parent
butyl acetate butyl acetate: structure. butyl acetate : The acetate ester of butanol.	2.42	2	0	acetate ester	metabolite
1,4-dioxane 1,4-dioxane: dehydrating agent; polar solvent miscible both with water & most organic solvents. dioxane : Any member of the class of dioxanes that is a cyclohexane in which two carbon atoms are replaced by oxygen atoms.. 1,4-dioxane : A dioxane with oxygen atoms at positions 1 and 4.	2.37	2	0	dioxane; volatile organic compound	carcinogenic agent; metabolite; NMR chemical shift reference compound; non-polar solvent
chloroprene Chloroprene: Toxic, possibly carcinogenic, monomer of neoprene, a synthetic rubber; causes damage to skin, lungs, CNS, kidneys, liver, blood cells and fetuses. Synonym: 2-chlorobutadiene.	3.82	2	1	chloroolefin
tetrachloroethylene Tetrachloroethylene: A chlorinated hydrocarbon used as an industrial solvent and cooling liquid in electrical transformers. It is a potential carcinogen.	5.16	45	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.	2.04	1	0	ortho- and peri-fused polycyclic arene	fluorescent probe; persistent organic pollutant
alkenes [no description available]	8.64	135	0
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.	3.62	9	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
cefazolin Cefazolin: A semisynthetic cephalosporin analog with broad-spectrum antibiotic action due to inhibition of bacterial cell wall synthesis. It attains high serum levels and is excreted quickly via the urine.. cefazolin : A first-generation cephalosporin compound having [(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl and (1H-tetrazol-1-ylacetyl)amino side-groups at positions 3 and 7 respectively.	2.4	2	0	beta-lactam antibiotic allergen; cephalosporin; tetrazoles; thiadiazoles	antibacterial drug
sodium azide Sodium Azide: A cytochrome oxidase inhibitor which is a nitridizing agent and an inhibitor of terminal oxidation. (From Merck Index, 12th ed). sodium azide : The sodium salt of hydrogen azide (hydrazoic acid).	7.42	2	0	inorganic sodium salt	antibacterial agent; explosive; mitochondrial respiratory-chain inhibitor; mutagen
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	2.69	3	0	pseudohalide anion	mitochondrial respiratory-chain inhibitor
timolol (S)-timolol (anhydrous) : The (S)-(-) (more active) enantiomer of timolol. A beta-adrenergic antagonist, both the hemihydrate and the maleate salt are used in the mangement of glaucoma, hypertension, angina pectoris and myocardial infarction, and for the prevention of migraine.	2.04	1	0	timolol	anti-arrhythmia drug; antiglaucoma drug; antihypertensive agent; beta-adrenergic antagonist
norflurazone norflurazone: structure. norflurazon : A pyridazinone that is pyridazin-3(2H)-one which is substituted at positions 2, 4, and 5 by m-(trifluoromethyl)phenyl, chloro, and methylamino groups, respectively. A pre-emergence herbicide used to control grasses and broad-leafed weeds in a variety of crops. Not approved for use within the European Union.	2.06	1	0	(trifluoromethyl)benzenes; organochlorine compound; pyridazinone; secondary amino compound	agrochemical; carotenoid biosynthesis inhibitor; herbicide
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).	5.98	4	1	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
miloxacin miloxacin: structure in second source	2.04	1	0	quinolines
ng-nitroarginine methyl ester NG-Nitroarginine Methyl Ester: A non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.	2.15	1	0	alpha-amino acid ester; L-arginine derivative; methyl ester; N-nitro compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor
deoxynivalenol deoxynivalenol : A trichothecene mycotoxin produced by Fusarium to which wheat, barley, maize (corn) and their products are susceptible to contamination.	2.05	1	0	cyclic ketone; enone; primary alcohol; secondary alpha-hydroxy ketone; trichothecene; triol	mycotoxin
thidiazuron [no description available]	8.14	4	0	ureas
chlorodiphenyl (54% chlorine) Chlorodiphenyl (54% Chlorine): A mixture of polychlorinated biphenyls that induces hepatic microsomal UDP-glucuronyl transferase activity towards thyroxine.. Aroclor 1254 : A mixture of polychlorobiphenyls of unspecified composition, containing 54% chlorine (X = Cl or H).	1.96	1	0
decamethrin decamethrin: pyrethroid insecticide; RN given refers to cpd without isomeric designation; structure	2.01	1	0	aromatic ether; cyclopropanecarboxylate ester; nitrile; organobromine compound	agrochemical; antifeedant; calcium channel agonist; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; pyrethroid ester insecticide
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid [no description available]	2.42	2	0	chromanol; monocarboxylic acid; phenols	antioxidant; ferroptosis inhibitor; neuroprotective agent; radical scavenger; Wnt signalling inhibitor
ethylene glycol dinitrate [no description available]	1.93	1	0
enkephalin, methionine Enkephalin, Methionine: One of the endogenous pentapeptides with morphine-like activity. It differs from LEU-ENKEPHALIN by the amino acid METHIONINE in position 5. Its first four amino acid sequence is identical to the tetrapeptide sequence at the N-terminal of BETA-ENDORPHIN.	1.99	1	0
fluridone [no description available]	5.01	12	0	phenylpyridine	carotenoid biosynthesis inhibitor
acifluorfen [no description available]	2.01	1	0	aromatic ether; benzoic acids; C-nitro compound; monocarboxylic acid; organochlorine compound; organofluorine compound	agrochemical; EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor; herbicide
4-(n-methyl-n-nitrosamino)-1-(3-pyridyl)-1-butanone 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone: structure; from tobacco smoke	2.03	1	0	nitrosamine; pyridines
alfentanil Alfentanil: A short-acting opioid anesthetic and analgesic derivative of FENTANYL. It produces an early peak analgesic effect and fast recovery of consciousness. Alfentanil is effective as an anesthetic during surgery, for supplementation of analgesia during surgical procedures, and as an analgesic for critically ill patients.. alfentanil : A member of the class of piperidines that is piperidine having a 2-(4-ethyl-5-oxo-4,5-dihydro-1H-tetrazol-1-yl)ethyl group at the 1-position as well as N-phenylpropanamido- and methoxymethyl groups at the 4-position.	2.04	1	0	monocarboxylic acid amide; piperidines	central nervous system depressant; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic; peripheral nervous system drug
fura-2 Fura-2: A fluorescent calcium chelating agent which is used to study intracellular calcium in tissues.	2	1	0
gemcitabine gemcitabine : A 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer.	4.61	1	1	organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; environmental contaminant; immunosuppressive agent; photosensitizing agent; prodrug; radiosensitizing agent; xenobiotic
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	2.48	2	0	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
n-butyllithium [no description available]	7.05	1	0
trichloroacetamide [no description available]	1.96	1	0
octyl gallate [no description available]	1.97	1	0	gallate ester	food antioxidant; hypoglycemic agent; plant metabolite
vanadates Vanadates: Oxyvanadium ions in various states of oxidation. They act primarily as ion transport inhibitors due to their inhibition of Na(+)-, K(+)-, and Ca(+)-ATPase transport systems. They also have insulin-like action, positive inotropic action on cardiac ventricular muscle, and other metabolic effects.. vanadate(3-) : A vanadium oxoanion that is a trianion with formula VO4 in which the vanadium is in the +5 oxidation state and is attached to four oxygen atoms.	2.43	2	0	trivalent inorganic anion; vanadium oxoanion	EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor
florisil Florisil: hard, porous, granular substance used in vitamin analysis, chromatography, & antibiotic processing	2.02	1	0
dimethylhydrazines Dimethylhydrazines: Hydrazines substituted with two methyl groups in any position.	1.97	1	0
1,3-pentadiene 1,3-pentadiene: a linear 5-carbon alkene; RN given refers to cpd with unspecified isomeric designation. (E)-1,3-pentadiene : An alkadiene consisting of pentane with the two double bonds located at positions 1 and 3.	2.15	1	0	alkadiene
benzylaminopurine benzylaminopurine: a plant growth regulator. N-benzyladenine : A member of the class of 6-aminopurines that is adenine in which one of the hydrogens of the amino group is replaced by a benzyl group.	4.21	17	0	6-aminopurines	cytokinin; plant metabolite
trifluoromethanesulfonic acid trifluoromethanesulfonic acid: deblocking reagent for peptide synthesis; RN given refers to parent cpd. triflic acid : A one-carbon compound that is methanesulfonic acid in which the hydrogens attached to the methyl carbon have been replaced by fluorines.	2.05	1	0	one-carbon compound; perfluoroalkanesulfonic acid
ethylenesulfonic acid [no description available]	1.92	1	0
sodium persulfate sodium persulfate: RN given refers to peroxydisulfuric acid, di-Na salt	2.21	1	0
2-butene 2-butene: RN given refers to cpd without isomeric designation	2.42	2	0	but-2-ene
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	4.35	19	0	D-glucopyranose	epitope; mouse metabolite
lanthanum chloride lanthanum chloride: RN given refers to parent cpd	3.11	5	0
cyclam cyclam: RN given refers to parent cpd; structure given in first source	2.77	3	0	azacycloalkane; crown amine; saturated organic heteromonocyclic parent
baicalin [no description available]	4.61	1	1	dihydroxyflavone; glucosiduronic acid; glycosyloxyflavone; monosaccharide derivative	antiatherosclerotic agent; antibacterial agent; anticoronaviral agent; antineoplastic agent; antioxidant; cardioprotective agent; EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; ferroptosis inhibitor; neuroprotective agent; non-steroidal anti-inflammatory drug; plant metabolite; prodrug
oseltamivir Oseltamivir: An acetamido cyclohexene that is a structural homolog of SIALIC ACID and inhibits NEURAMINIDASE.. oseltamivir : A cyclohexenecarboxylate ester that is the ethyl ester of oseltamivir acid. An antiviral prodrug (it is hydrolysed to the active free carboxylic acid in the liver), it is used to slow the spread of influenza.	2.05	1	0	acetamides; amino acid ester; cyclohexenecarboxylate ester; primary amino compound	antiviral drug; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; environmental contaminant; prodrug; xenobiotic
thionine thionine: do not confuse with the thionins which is a class of polypeptides; RN above is for the chloride;. thionine : An organic chloride salt composed of 3,7-diaminophenothiazin-5-ium and chloride ions in a 1:1 ratio. A strongly metachromatic dye, useful for the staining of acid mucopolysaccharides. It is also a common nuclear stain and can be used for the demonstration of Nissl substance in nerve cells of the CNS.	2.05	1	0
diacetylfluorescein [no description available]	2.13	1	0
1,3-oxathiolane 1,3-oxathiolane: structure	7.05	1	0
phosphoramidic acid phosphoramidic acid: urease inhibitor; RN given refers to parent cpd; structure; do not confuse with phosphoramidites, which are organophosphorus compounds	2.17	1	0	phosphoric acid derivative
peroxynitric acid [no description available]	3.82	4	0	nitrogen oxoacid
glutathione disulfide Glutathione Disulfide: A GLUTATHIONE dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized.	3.91	3	0	glutathione derivative; organic disulfide	Escherichia coli metabolite; mouse metabolite
cephalosporin c cephalosporin C: RN given refers to parent cpd; structure in Merck, 9th ed, #1937. cephalosporin C : A cephalosporin antibiotic carrying a 3-acetoxymethyl substituent and a 6-oxo-N(6)-L-lysino group at position 7.	3.1	1	0	cephalosporin	fungal metabolite
tomatidine tomatidine: RN given refers to (3beta,5alpha,22beta,25S)-isomer; structure. tomatidine : A 3beta-hydroxy steroid resulting from the substitution of the 3beta-hydrogen of tomatidane by a hydroxy group.	2.06	1	0	3beta-hydroxy steroid; azaspiro compound; oxaspiro compound
dicarbine dicarbine: minor descriptor (77-84); on-line & Index Medicus search CARBOLINES (77-84); RN given refers to parent cpd without isomeric designation	1.97	1	0
inaperisone inaperisone: structure given in first source; RN given refers to parent cpd without isomeric designation	2.04	1	0	aromatic ketone
naphthalimides Naphthalimides: Compounds with three fused rings that appear like a naphthalene fused to piperidone or like a benz(de)isoquinoline-1,3-dione (not to be confused with BENZYLISOQUINOLINES which have a methyl separating the naphthyl from the benzyl rings). Members are CYTOTOXINS.	2.04	1	0
anthraquinone-2,6-disulfonate anthraquinone-2,6-disulfonate: structure in first source. anthraquinone-2,6-disulfonic acid : A member of the class of anthraquinones that is 9,10-anthraquinone substituted at positions 2 and 6 by sulfo groups.	2.49	2	0	anthraquinone; arenesulfonic acid
salicylhydroxamic acid [no description available]	2.03	1	0	hydroxamic acid; phenols	antibacterial drug; EC 1.11.2.2 (myeloperoxidase) inhibitor; EC 3.5.1.5 (urease) inhibitor; trypanocidal drug
4-phenylbenzoic acid 4-phenylbenzoic acid: RN given refers to 4-carboxylic cpd	2.04	1	0
1,7-phenanthroline [no description available]	2.76	3	0	phenanthroline
benzo-1,2,3-thiadiazole [no description available]	3.75	10	0
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.	4.07	15	0	1,2,3-triazole
trifluoroacetamide [no description available]	1.96	1	0
delphinidin Paraffin: A mixture of solid hydrocarbons obtained from petroleum. It has a wide range of uses including as a stiffening agent in ointments, as a lubricant, and as a topical anti-inflammatory. It is also commonly used as an embedding material in histology.. delphinidin chloride : An anthocyanidin chloride that has delphinidin as the cationic counterpart.	3.63	2	0	anthocyanidin chloride
artemisinin (+)-artemisinin : A sesquiterpene lactone obtained from sweet wormwood, Artemisia annua, which is used as an antimalarial for the treatment of multi-drug resistant strains of falciparum malaria.	3.1	1	0	organic peroxide; sesquiterpene lactone	antimalarial; plant metabolite
5-iodouracil 5-iodouracil: RN given refers to parent cpd. 5-iodouracil : An organoiodine compound consisting of uracil having an iodo substituent at the 5-position.	1.96	1	0	organoiodine compound	antimetabolite
dapoxetine [no description available]	4.61	1	1	naphthalenes
masoprocol Masoprocol: A potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. The compound also inhibits formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase to a lesser extent. It also serves as an antioxidant in fats and oils.. masoprocol : The meso-form of nordihydroguaiaretic acid. An antioxidant found in the creosote bush, Larrea divaricata, it is a potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. It also inhibits (though to a lesser extent) formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase.	3.03	4	0	nordihydroguaiaretic acid	antineoplastic agent; hypoglycemic agent; lipoxygenase inhibitor; metabolite
voriconazole Voriconazole: A triazole antifungal agent that specifically inhibits STEROL 14-ALPHA-DEMETHYLASE and CYTOCHROME P-450 CYP3A.. voriconazole : A triazole-based antifungal agent used for the treatment of esophageal candidiasis, invasive pulmonary aspergillosis, and serious fungal infections caused by Scedosporium apiospermum and Fusarium spp. It is an inhibitor of cytochrome P450 2C9 (CYP2C9) and CYP3A4.	4.61	1	1	conazole antifungal drug; difluorobenzene; pyrimidines; tertiary alcohol; triazole antifungal drug	P450 inhibitor
narciclasine narciclasine: antitumor alkaloid from bulbs of Narcissus species	2.1	1	0	phenanthridines	metabolite
alkannin alkannin: a naphthazarin used to promote wound healing, from the plant Alkanna tinctoria; RN given refers to (S)-isomer; structure	2.1	1	0	hydroxy-1,4-naphthoquinone
serpentine (alkaloid) serpentine (alkaloid): do not confuse with mineral serpentine; RN given refers to (19alpha)-isomer; structure	2.17	1	0	carboxylic ester; iminium betaine; indole alkaloid; quinolizines; zwitterion
tosyllysine chloromethyl ketone Tosyllysine Chloromethyl Ketone: An inhibitor of SERINE ENDOPEPTIDASES. Acts as an alkylating agent and is known to interfere with the translation process.	2.01	1	0	sulfonic acid derivative
bes 2-[bis(2-hydroxyethyl)amino]ethanesulfonic acid : A Good's buffer substance, pKa = 7.15 at 20 degreeC.	1.97	1	0	1,1-diunsubstituted alkanesulfonate; amino sulfonic acid; BES
sakuranetin sakuranetin: major rice phytoalexin; RN given for ((S)-(-))-isomer; structure in first source. sakuranetin : A flavonoid phytoalexin that is (S)-naringenin in which the hydroxy group at position 7 is replaced by a methoxy group.	2	1	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; flavonoid phytoalexin; monomethoxyflavanone	antimycobacterial drug; plant metabolite
isoxaben isoxaben : A benzamide obtained by formal condensation of the carboxy group of 2,6-dimethoxybenzoic acid and the amino group of 3-(3-methylpentan-3-yl)-1,2-oxazol-5-amine.	2.44	2	0	benzamides; isoxazoles	cellulose synthesis inhibitor; herbicide
2,2'-dipicolylamine 2,2'-dipicolylamine: structure in first source	2.02	1	0
oxazolidin-2-one Oxazolidinones: Derivatives of oxazolidin-2-one. They represent an important class of synthetic antibiotic agents.. oxazolidin-2-one : An oxazolidinone that is 1,3-oxazolidine with an oxo substituent at position 2.. oxazolidinone : An oxazolidine containing one or more oxo groups.	2.01	1	0	carbamate ester; oxazolidinone	metabolite
ceric oxide ceric oxide: RN given refers to cpd with MF CeO2. ceric oxide : A metal oxide with formula CeO2. It is used for polishing glass, in coatings for infra-red filters to prevent reflection, and as an oxidant and catalyst in organic synthesis.	2.49	2	0	cerium molecular entity; metal oxide
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.	2.6	1	0	perfluoroalkanesulfonic acid	antilipemic drug; persistent organic pollutant
9-oxononanoic acid 9-oxononanoic acid: effects lipogenesis in rat liver. 9-oxononanoic acid : A medium-chain oxo-fatty acid that is the 9-oxo derivative of nonanoic acid.	2.06	1	0	aldehydic acid; medium-chain fatty acid; omega-oxo fatty acid	EC 6.4.1.2 (acetyl-CoA carboxylase) inhibitor
octadecyl palmitate octadecyl palmitate: found in psoriatic nail, but not in normal nails. stearyl palmitate : A palmitate ester resulting from the formal condensation of the carboxy group of palmitic acid with the hydroxy group of stearyl alcohol.	2.48	2	0	hexadecanoate ester; wax ester	coral metabolite; cosmetic
1-naphthoxyacetic acid [no description available]	2.01	1	0	naphthyloxyacetic acid
2',7'-dichlorodihydrofluorescein diacetate [no description available]	2.1	1	0
3-methylthiopropylamine 3-methylthiopropylamine : A derivative of propylamine having a methylmercapto group at the 3-position.	2.01	1	0	organic sulfide; primary amino compound
trifluoromethyl hypofluorite trifluoromethyl hypofluorite: reagent in fluorination of nucleosides; structure	2.1	1	0
2,4-diamino-5-benzylpyrimidine 2,4-diamino-5-benzylpyrimidine: structure given in first source	1.96	1	0
s-methyl benzo(1,2,3)thiadiazole-7-carbothioate S-methyl benzo(1,2,3)thiadiazole-7-carbothioate: induces system acquired resistance in wheat; structure in first source. acibenzolar-S-methyl : A benzothiadiazole that is the S-methyl thioester derivative of acibenzolar. A profungicide (by hydrolysis of the thioester group to give the corresponding carboxylic acid), it is used as a fungicide and plant activator on a variety of crops, including cotton, chili peppers, lettuce, onions, spinach, tobacco, and tomatoes.	2.46	2	0	benzothiadiazole; thioester	antifungal agrochemical; plant activator; profungicide
titanium hydroxide titanium hydroxide: RN given refers to cpd with unknown MF	2.02	1	0
nicotine (S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.	6.47	13	1	3-(1-methylpyrrolidin-2-yl)pyridine	anxiolytic drug; biomarker; immunomodulator; mitogen; neurotoxin; nicotinic acetylcholine receptor agonist; peripheral nervous system drug; phytogenic insecticide; plant metabolite; psychotropic drug; teratogenic agent; xenobiotic
1-aminocyclobutanecarboxylic acid 1-aminocyclobutanecarboxylic acid: RN given refers to unlabeled cpd	1.99	1	0	L-alpha-amino acid
fibrinogen Fibrinogen: Plasma glycoprotein clotted by thrombin, composed of a dimer of three non-identical pairs of polypeptide chains (alpha, beta, gamma) held together by disulfide bonds. Fibrinogen clotting is a sol-gel change involving complex molecular arrangements: whereas fibrinogen is cleaved by thrombin to form polypeptides A and B, the proteolytic action of other enzymes yields different fibrinogen degradation products.. D-iditol : The D-enantiomer of iditol.	2.37	2	0	iditol	fungal metabolite
2,2-dimethoxy-2-phenylacetophenone [no description available]	2.05	1	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.	2.21	1	0	amino acid zwitterion; homocysteine; serine family amino acid	fundamental metabolite; mouse metabolite
oryzemate oryzemate: induces disease resistance against rice blast fungus in rice; structure in first source. probenazole : A member of the class of 1,2-benzothiazoles that is 1,2-benzothiazole 1,1-dioxide substituted at position 3 by an allyloxy group. A fungicide used to control rice blast.	2	1	0	1,2-benzisothiazole; aromatic ether; benzothiazole fungicide; sulfone	antifungal agrochemical; plant activator
coronatine coronatine: consists of a coronafacic acid joined by an amide bond to coronamic acid by coronafacate ligase; phytotoxin produced by Pseudomonas syringae; RN given refers to (3aS-(3aalpha,4(1R,2R),6beta,7alpha))-isomer;	3.41	7	0	N-acyl-amino acid
quinclorac quinclorac: an herbicide. quinclorac : A quinolinemonocarboxylic acid that is quinoline-8-carboxylic acid in which the hydrogens at positions 3 and 7 have been replaced by chlorines. It is used (particularly as its dimethylamine salt, known as quinclorac-dimethylammonium) as a (rather persistent) herbicide for the post-emergence control of weeds in rice, grass and turf. It is not approved for use within the European Union.	8.19	5	0	monocarboxylic acid; organochlorine compound; quinolinemonocarboxylic acid	agrochemical; herbicide; synthetic auxin
prosulfuron prosulfuron: structure in first source	2.02	1	0	triazines
halosulfuron methyl halosulfuron methyl: an herbicide; structure in first source	2.15	1	0	pyrazoles
primisulfuron primisulfuron: structure in first source	2.02	1	0	benzoic acids
lopinavir [no description available]	4.61	1	1	amphetamines; dicarboxylic acid diamide	anticoronaviral agent; antiviral drug; HIV protease inhibitor
gamma-tocopherol gamma-Tocopherol: A natural tocopherol with less antioxidant activity than ALPHA-TOCOPHEROL. It exhibits antioxidant activity by virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus. As in BETA-TOCOPHEROL, it also has three methyl groups on the 6-chromanol nucleus but at different sites.. gamma-tocopherol : A tocopherol in which the chroman-6-ol core is substituted by methyl groups at positions 7 and 8. It is found particularly in maize (corn) oil and soya bean (soybean) oils.	2.06	1	0	tocopherol; vitamin E	algal metabolite; food antioxidant; plant metabolite
glycidyl nitrate glycidyl nitrate: a nitric oxide donor; structure in first source. peptidoglycan : A peptidoglycosaminoglycan formed by alternating residues of beta-(1->4)-linked N-acetylglucosamine and N-acetylmuramic acid {2-amino-3-O-[(S)-1-carboxyethyl]-2-deoxy-D-glucose} residues. Attached to the carboxy group of the muramic acid is a peptide chain of three to five amino acids.	2.05	1	0
n-(2-chloro-4-pyridyl)-n'-phenylurea forchlorfenuron : A member of the class of phenylureas that is urea substituted by a phenyl group and a 2-chloropyridin-4-yl group at positions 1 and 3 respectively. It is a plant growth regulator widely used in agriculture for improving fruit quality and fruit size.	2.44	2	0	monochloropyridine; phenylureas	plant growth regulator
glucuronic acid Glucuronic Acid: A sugar acid formed by the oxidation of the C-6 carbon of GLUCOSE. In addition to being a key intermediate metabolite of the uronic acid pathway, glucuronic acid also plays a role in the detoxification of certain drugs and toxins by conjugating with them to form GLUCURONIDES.. D-glucuronic acid : The D-enantiomer of glucuronic acid.. D-glucopyranuronic acid : A D-glucuronic acid in cyclic pyranose form.	2.46	2	0	D-glucuronic acid	algal metabolite
2,6-dichloroisonicotinic acid 2,6-dichloroisonicotinic acid: an ascorbate peroxidase antagonist; RN given refers to parent cpd. 2,6-dichloroisonicotinic acid : A member of the class of pyridines that is isonicotinic acid which is substituted by chlorine at positions 2 and 6.	2.01	1	0	monocarboxylic acid; organochlorine compound; pyridines	EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor
1-phenazinecarboxylic acid 1-phenazinecarboxylic acid: from Streptomyces cinnamonensis; RN given refers to parent cpd; structure given in first source. phenazine-1-carboxylic acid : An aromatic carboxylic acid that is phenazine substituted at C-1 with a carboxy group.	2.1	1	0	aromatic carboxylic acid; monocarboxylic acid; phenazines	antifungal agent; antimicrobial agent; bacterial metabolite
tetrathiafulvalene tetrathiafulvalene: used in carbon paste amperometric enzyme electrode for the determination of glucose in flowing systems. tetrathiafulvalene : A member of the class of fulvalenes that is ethene substituted by 1,3-dithiol-2-ylidene groups at positions 1 and 2.	2.05	1	0	fulvalenes; organosulfur heterocyclic compound
diosgenin [no description available]	7.02	1	0	3beta-sterol; hexacyclic triterpenoid; sapogenin; spiroketal	antineoplastic agent; antiviral agent; apoptosis inducer; metabolite
combretastatin combretastatin: cytotoxic principle from South African tree COMBRETUM caffrum; structure given in first source; acts at COLCHICINE site of TUBULIN	7.02	1	0
4-chloroindole-3-acetic acid [no description available]	7.15	1	0	chloroindole-3-acetic acid	auxin
4,8-dimethyl-1,3,7-nonatriene 4,8-dimethyl-1,3,7-nonatriene: structure in first source	2.46	2	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.	5.82	29	0	cobalt group element atom; metal allergen	micronutrient
hydrogen sulfite [no description available]	3.35	1	0	sulfur oxoanion	human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
1-amino-1,3-dicarboxycyclopentane 1-amino-1,3-dicarboxycyclopentane: RN given refers to (cis)-isomer	1.98	1	0
arginyl-glycyl-aspartic acid arginyl-glycyl-aspartic acid: amino acid sequence of basic unit of widespread cellular recognition system	2.07	1	0	oligopeptide
vitamin b 6 Vitamin B 6: VITAMIN B 6 refers to several PICOLINES (especially PYRIDOXINE; PYRIDOXAL; & PYRIDOXAMINE) that are efficiently converted by the body to PYRIDOXAL PHOSPHATE which is a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, and aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into PYRIDOXAMINE phosphate. Although pyridoxine and Vitamin B 6 are still frequently used as synonyms, especially by medical researchers, this practice is erroneous and sometimes misleading (EE Snell; Ann NY Acad Sci, vol 585 pg 1, 1990). Most of vitamin B6 is eventually degraded to PYRIDOXIC ACID and excreted in the urine.	2.42	2	0
s-nitrosoglutathione [no description available]	2.06	1	0	glutathione derivative; nitrosothio compound	bronchodilator agent; nitric oxide donor; platelet aggregation inhibitor; signalling molecule
1,n(6)-ethenoadenine 1,N(6)-ethenoadenine: biologically active fluorescent derivatives of this cpd potentially valuable in studies concerning interactions between adenine cpds & various enzymes for which they serve as substrates or co-factors; structure	4.61	1	1	imidazo[2,1-i]purine	mutagen
fructose 2,6-diphosphate fructose 2,6-diphosphate: phosphofructokinase activator synthesized via Mg-ATP & fructose-6-P. beta-D-fructofuranose 2,6-bisphosphate : A D-fructofuranose 2,6-bisphosphate with a beta-configuration at the anomeric centre.	1.97	1	0	D-fructofuranose 2,6-bisphosphate	human metabolite; mouse metabolite
cyanates Cyanates: Organic salts of cyanic acid containing the -OCN radical.. cyanates : Salts and esters of cyanic acid, HOC#N; compounds carrying the cyanate functional group -O-C#N.. isocyanates : Organonitrogen compounds that are derivatives of isocyanic acid; compounds containing the isocyanate functional group -N=C=O (as opposed to the cyanate group, -O-C#N).	2.97	4	0
thiamethoxam Thiamethoxam: A nitro-oxazine and thiazole derivative that is used as a broad spectrum neonicotinoid insecticide.. thiamethoxam : An oxadiazane that is tetrahydro-N-nitro-4H-1,3,5-oxadiazin-4-imine bearing (2-chloro-1,3-thiazol-5-yl)methyl and methyl substituents at positions 3 and 5 respectively.	4.61	1	1	1,3-thiazoles; 2-nitroguanidine derivative; organochlorine compound; oxadiazane	antifeedant; carcinogenic agent; environmental contaminant; neonicotinoid insectide; xenobiotic
aceanthrylene aceanthrylene: structure given in first source	1.99	1	0	ortho- and peri-fused polycyclic arene
procyanidin Proanthocyanidins: Dimers and oligomers of flavan-3-ol units (CATECHIN analogs) linked mainly through C4 to C8 bonds to leucoanthocyanidins. They are structurally similar to ANTHOCYANINS but are the result of a different fork in biosynthetic pathways.	2.52	2	0	proanthocyanidin
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.	2.75	3	0	phosphite ion; trivalent inorganic anion
2-hydroxyethylvaline 2-hydroxyethylvaline: RN given refers to (DL)-isomer; RN for cpd without isomeric designation not available 11/88	3.5	8	0
daidzin daidzin: a potent, selective, and reversible inhibitor of human mitochondrial aldehyde dehydrogenase. daidzein 7-O-beta-D-glucoside : A glycosyloxyisoflavone that is daidzein attached to a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. It is used in the treatment of alcohol dependency (antidipsotropic).	2.13	1	0	7-hydroxyisoflavones 7-O-beta-D-glucoside; hydroxyisoflavone; monosaccharide derivative	plant metabolite
proanthocyanidin proanthocyanidin: RN given refers to proanthocyanidin A; Cannabinoid Receptor CB1 antagonist. proanthocyanidin : A flavonoid oligomer obtained by the the condensation of two or more units of hydroxyflavans.	7.17	1	0
tanshinone tanshinone: from root of Salvia miltiorrhiza Bunge; RN given refers to tanshinone I; cardioprotective agent and neuroprotective agent	2.61	2	0	abietane diterpenoid	anticoronaviral agent
pumiliotoxin c pumiliotoxin C: isolated from skin of Dendrobates pumilio (frog); see also records for pumiliotoxin A, pumiliotoxin B & pumiliotoxins	3.12	1	0
brassinolide brassinolide: plant growth promoting steroidal lactone from rape pollen; RN given refers to (2alpha,3alpha,5alpha,22R,23R,24S)-isomer; structure in first source	4.52	23	0	22-hydroxy steroid; 23-hydroxy steroid; 2alpha-hydroxy steroid; 3alpha-hydroxy steroid; brassinosteroid	plant growth stimulator; plant hormone
1,2-dioxetane [no description available]	2.07	1	0
benzoyl-coenzyme a benzoyl-coenzyme A: RN given refers to unlabeled cpd	1.98	1	0
phenoxy radical phenoxy radical : An organic radical generated from phenol.	2.5	2	0	organic radical
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).	3.14	5	0	carbene; methanediyl
cyclopropene cyclopropene: structure. cyclopropene : A cycloalkene that consists of cyclopropane having a double bond in the ring. The parent of the class of cyclopropenes.	2.06	1	0	cycloalkene; cyclopropenes
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
peroxynitrous acid Peroxynitrous Acid: A potent oxidant synthesized by the cell during its normal metabolism. Peroxynitrite is formed from the reaction of two free radicals, NITRIC OXIDE and the superoxide anion (SUPEROXIDES).	5.46	4	1	nitrogen oxoacid
fullerene c60 Fullerenes: A polyhedral CARBON structure composed of around 60-80 carbon atoms in pentagon and hexagon configuration. They are named after Buckminster Fuller because of structural resemblance to geodesic domes. Fullerenes can be made in high temperature such as arc discharge in an inert atmosphere.. fullerene : A compound composed solely of an even number of carbon atoms, which form a cage-like fused-ring polycyclic system with twelve five-membered rings and the rest six-membered rings. The term has been broadened to include any closed cage structure consisting entirely of three-coordinate carbon atoms.	2.74	3	0	fullerene	geroprotector
imatinib mesylate imatinib methanesulfonate : A methanesulfonate (mesylate) salt that is the monomesylate salt of imatinib. Used for treatment of chronic myelogenous leukemia and gastrointestinal stromal tumours.	4.61	1	1	methanesulfonate salt	anticoronaviral agent; antineoplastic agent; apoptosis inducer; tyrosine kinase inhibitor
gefitinib [no description available]	4.61	1	1	aromatic ether; monochlorobenzenes; monofluorobenzenes; morpholines; quinazolines; secondary amino compound; tertiary amino compound	antineoplastic agent; epidermal growth factor receptor antagonist
ribulose-1,5 diphosphate ribulose-1,5 diphosphate: RN given refers to cpd without isomeric designation. D-ribulose 1,5-bisphosphate : A ribulose phosphate that is D-ribulose attached to phosphate groups at positions 1 and 5. It is an intermediate in photosynthesis.	2.1	1	0	ribulose phosphate	Escherichia coli metabolite; plant metabolite
cholesterol hydroperoxide cholesterol hydroperoxide: RN given refers to (3beta,5beta)-isomer	1.98	1	0
cyclic adp-ribose Cyclic ADP-Ribose: A pyridine nucleotide that mobilizes CALCIUM. It is synthesized from nicotinamide adenine dinucleotide (NAD) by ADP RIBOSE CYCLASE.	2.07	1	0	cyclic purine nucleotide; nucleotide-sugar	metabolite; ryanodine receptor agonist
ferric bleomycin iron bleomycin: iron-bleomycin complexes	1.96	1	0
1,2,3,4-tetrahydroxy-nor-tropane calystegine B(2): RN given for (2-endo,3-exo,4-endo)-isomer; structure in first source	2.05	1	0
chrysobactin chrysobactin: from Erwinia chrysanthemi; has siderophore activity; structure given in first source. chrysobactin : A catechol-type siderophore with a structure of D-lysyl-L-serine substituted on N(2) of the lysyl residue by a 2,3-dihydroxybenzoyl group. It is produced by the Gram-negative bacillus Dickeya dadantii (previously known as Erwinia chrysanthem). Only the catecholate hydroxyl groups participate in metal coordination, so chrysobactin cannot provide full 1:1 coordination of Fe(III); at neutral pH and concentrations of about 0.1 mM, ferric chrysobactin exists as a mixture of bis and tris complexes.	2.05	1	0	catechols; dipeptide; monocarboxylic acid; primary alcohol; primary amino compound	bacterial metabolite; siderophore
2-hydroxypropylvaline 2-hydroxypropylvaline: RN given refers to (DL)-isomer; RN for cpd without isomeric designation not available 11/88	1.97	1	0
1-amino-2-ethylcyclopropane-1-carboxylic acid 1-amino-2-ethylcyclopropane-1-carboxylic acid: an ethylcyclopropyl amino-acid derived from isoleucine; it may be coupled to coronafacic acid by coronafacate ligase to form coronatine; substrate of malonyltransferase & inhibitor of 1-aminocyclopropane-1-carboxylic acid malonyltransferase; RN given refers to cpd without isomeric designation	2.06	1	0	amino monocarboxylic acid
carbapenems [no description available]	3.12	1	0
calcium borate calcium borate: RN given refers to cpd with MF CaB4O7	4.61	1	1
beta-lactams 2-azetidinone: structure in first source. azetidin-2-one : An unsubstituted beta-lactam compound.. beta-lactam : A lactam in which the amide bond is contained within a four-membered ring, which includes the amide nitrogen and the carbonyl carbon.	3.55	2	0	beta-lactam antibiotic allergen; beta-lactam
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.	4.37	19	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
cdri 81-470 [no description available]	2.04	1	0
docetaxel anhydrous Docetaxel: A semisynthetic analog of PACLITAXEL used in the treatment of locally advanced or metastatic BREAST NEOPLASMS and NON-SMALL CELL LUNG CANCER.. docetaxel anhydrous : A tetracyclic diterpenoid that is paclitaxel with the N-benzyloxycarbonyl group replaced by N-tert-butoxycarbonyl, and the acetoxy group at position 10 replaced by a hydroxy group.	4.61	1	1	secondary alpha-hydroxy ketone; tetracyclic diterpenoid	antimalarial; antineoplastic agent; photosensitizing agent
1-methylcyclopropene 1-methylcyclopropene: do not confuse with 1-methylcyclopropane. 1-methylcyclopropene : A member of the class of cyclopropenes that is cyclopropene in which the hydrogen at position 1 has been replaced by a methyl group. A gas at room temperture and pressure, it is a (synthetic) ethylene perception inhibitor and is used to prolong the life of cut and potted flowers, other ornamental plants, and fruit.	8	150	0	cycloalkene; cyclopropenes	agrochemical; plant growth regulator
2-keto-4-mercaptobutyric acid 2-keto-4-mercaptobutyric acid: homocysteine metabolite; structure given in first source	3.07	5	0
salicylic acid glucoside salicylic acid glucoside: structure given in first source; induces pathogenesis-related protein expression in tobacco; involved in systemic acquired resistance. 2-(D-glucosyloxy)benzoic acid : A monosaccharide derivative that is salicylic acid in which the phenolic hydrogen is replaced by a D-glucosyl residue.	2.03	1	0	benzoic acids; D-glucoside; monosaccharide derivative
vinylglycine vinylglycine: irreversible inhibitor of aspartate aminotransferase; structure. L-vinylglycine : A non-proteinogenic L-alpha-amino acid with a structure in which a vinyl group is bonded to the alpha-carbon of glycine.	2.05	1	0	glycine derivative; L-alpha-amino acid zwitterion; non-proteinogenic L-alpha-amino acid	EC 4.4.1.14 (1-aminocyclopropane-1-carboxylate synthase) inhibitor
naproxen Naproxen: An anti-inflammatory agent with analgesic and antipyretic properties. Both the acid and its sodium salt are used in the treatment of rheumatoid arthritis and other rheumatic or musculoskeletal disorders, dysmenorrhea, and acute gout.. naproxen : A methoxynaphthalene that is 2-methoxynaphthalene substituted by a carboxy ethyl group at position 6. Naproxen is a non-steroidal anti-inflammatory drug commonly used for the reduction of pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, kidney stones, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis, bursitis, and for the treatment of primary dysmenorrhea. It works by inhibiting both the COX-1 and COX-2 enzymes.	2	1	0	methoxynaphthalene; monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; gout suppressant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	5.23	16	0	oxygen hydride; oxygen radical; reactive oxygen species
adenosine 3'-phosphate-5'-phosphate adenosine 3',5'-bismonophosphate : An adenosine bisphosphate having two monophosphate groups at the 3'- and 5'-positions.	2.05	1	0	adenosine bisphosphate	Escherichia coli metabolite; mouse metabolite
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.	8.31	6	0	chalcogen; monoatomic oxygen; nonmetal atom	macronutrient
silver phosphate silver phosphate: for chloride analysis in cystic fibrosis patch test	2.1	1	0
fenton's reagent Fenton's reagent: used for oxidizing sugars & alcohols	1.98	1	0
carbodiimides Carbodiimides: Compounds with the general formula RN=C=NR, where R is a hydrocarbyl group.. methanediimine : A carbodiimide in which both nitrogens are unsubstituted.	7.4	2	0	carbodiimide
zirconium phosphate zirconium phosphate: reagent for carcinoembryonic antigen determination in plasma from patients having benign or malignant disease; RN given refers to cpd with unspecified ratio	3.21	1	0
capsidiol capsidiol: isolated from cultured cells of Nicotiana silvestris; structure given in first source. capsidiol : An eremophilane sesquiterpenoid that is (+)-5-epi-aristolochene bearing additional 1beta- and 3alpha-hydroxy substituents. It is a phytoalexin produced in Nicotiana and Capsicum plant species in response to pathogen attack.	2.1	1	0	eremophilane sesquiterpenoid; octahydronaphthalenes; sesquiterpene phytoalexin	antifungal agent; plant metabolite
momilactone a momilactone A: RN given for (3aR-(3aalpha,5aalpha,8beta,10abeta,10bbeta,10calpha))-isomer	2	1	0	diterpene lactone; pimarane diterpenoid
sclareol sclareol: structure given in first source. sclareol : A labdane diterpenoid that is labd-14-ene substituted by hydroxy groups at positions 8 and 13. It has been isolated from Salvia sclarea.	7.96	4	0	labdane diterpenoid	antifungal agent; antimicrobial agent; apoptosis inducer; fragrance; plant metabolite
alpha-aminooxy-beta-phenylpropionic acid alpha-aminooxy-beta-phenylpropionic acid: inhibits phenylalanine ammonia-lyase; RN given refers to (S)-isomer	2	1	0
magnesium-pyridoxal-5'-phosphate glutamate [no description available]	1.98	1	0
lignin Lignin: The most abundant natural aromatic organic polymer found in all vascular plants. Lignin together with cellulose and hemicellulose are the major cell wall components of the fibers of all wood and grass species. Lignin is composed of coniferyl, p-coumaryl, and sinapyl alcohols in varying ratios in different plant species. (From Merck Index, 11th ed). lignin : A polyphenylpropanoid derived from three monolignol monomers: trans-p-coumaryl alcohol, coniferol and trans-sinapyl alcohol. There is extensive cross-linking and no defined primary structure.	5.1	41	0
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	2.46	2	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.	2.05	1	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
4,8,12-trimethyl-1,3,7,11-tridecatetraene 4,8,12-trimethyl-1,3,7,11-tridecatetraene: released by lima bean plants upon predation by T. urticae	2.07	1	0
erythritol 4-phosphate D-erythritol 4-phosphate : A tetritol phosphate consisting of D-erythritol having the phosphate at the 4-position.	2.11	1	0	alditol 4-phosphate; tetritol phosphate
thermospermine thermospermine: polyamine extracted from an extreme thermopile, Thermus thermophilus; structure. thermospermine : Propane-1,3-diamine in which a hydrogen attached to one nitrogen is substituted by a 3-aminoprop-1-yl group, and a hydrogen attached to the other nitrogen is substituted by a 4-aminobut-1-yl group. A polyamine natural product, its name arises from its similarity to spermine and the fact that it was first isolated from the extreme thermophile, Thermus thermophilus.	3.18	1	0	polyazaalkane; tetramine
cucurbit(6)uril cucurbit(6)uril: a macrocyclic cavitand comprising six GLYCOLURIL units; can be used for creating ROTAXANES. cucurbituril : A macrocycle consisting of repeating 2,5-dioxodihydroimidazo[4,5-d]imidazole-1,3,4,6-tetrayl (glycoluril) units linked by methylene groups. The number of glycoluril units in the macrocycle is denoted by the "n" in cucurbit[n]uril name.	2.06	1	0
chlorite [no description available]	2.15	1	0	chlorine oxoanion; monovalent inorganic anion
yh 1885 YH 1885: proton pump inhibitor; structure in first source	2.04	1	0
anabasine Anabasine: A piperidine botanical insecticide.. (S)-anabasine : The (S)-enantiomer of anabasine.. anabasine : A pyridine alkaloid that is pyridine substituted by a piperidin-2-yl group at position 3.	2.21	1	0	anabasine
erythritol [no description available]	2.49	2	0	butane-1,2,3,4-tetrol	antioxidant; human metabolite; plant metabolite
deoxycholic acid Deoxycholic Acid: A bile acid formed by bacterial action from cholate. It is usually conjugated with glycine or taurine. Deoxycholic acid acts as a detergent to solubilize fats for intestinal absorption, is reabsorbed itself, and is used as a choleretic and detergent.. deoxycholic acid : A bile acid that is 5beta-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 12 respectively.	2	1	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human blood serum metabolite
delrin delrin: linear polyoxymethylene type acetal resin made by polymerization of formaldehyde; RN refers to multi-polymer	1.98	1	0
3-nitrotyrosine 3-nitrotyrosine: RN given refers to parent cpd without isomeric designation. 3-nitrotyrosine : A nitrotyrosine comprising tyrosine having a nitro group at the 3-position on the phenyl ring.	2.03	1	0	2-nitrophenols; C-nitro compound; nitrotyrosine; non-proteinogenic alpha-amino acid
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.	7.1	1	0	arenecarbaldehyde; furans; primary alcohol	indicator; Maillard reaction product
propargylamine propargylamine: RN given refers to parent cpd; structure	7.03	1	0
lanosterol [no description available]	2.15	1	0	14alpha-methyl steroid; 3beta-sterol; tetracyclic triterpenoid	bacterial metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
pheophorbide a pheophorbide a: split product of chlorophyll obtained by saponification of pheophytin	2.13	1	0
lupeol [no description available]	2.17	1	0	pentacyclic triterpenoid; secondary alcohol	anti-inflammatory drug; plant metabolite
fusicoccin fusicoccin: phytotoxic glycoside from Fusicoccum amydali; structure	2.69	3	0
homoharringtonine Homoharringtonine: Semisynthetic derivative of harringtonine that acts as a protein synthesis inhibitor and induces APOPTOSIS in tumor cells. It is used in the treatment of MYELOID LEUKEMIA, CHRONIC.. omacetaxine mepesuccinate : A cephalotaxine-derived alkaloid ester obtained from Cephalotaxus harringtonia; used for the treatment of chronic or accelerated phase chronic myeloid leukaemia.	3.12	1	0	alkaloid ester; enol ether; organic heteropentacyclic compound; tertiary alcohol	anticoronaviral agent; antineoplastic agent; apoptosis inducer; protein synthesis inhibitor
2-oxindole 2-oxindole: RN given refers to parent cpd; structure. indolin-2-one : An indolinone carrying an oxo group at position 2.	2.45	2	0	gamma-lactam; indolinone
indole-3-acetonitrile indole-3-acetonitrile: occurs in edible cruciferous vegetables. indole-3-acetonitrile : A nitrile that is acetonitrile where one of the methyl hydrogens is substituted by a 1H-indol-3-yl group.	2.05	1	0	indoles; nitrile	auxin; human xenobiotic metabolite; plant hormone; plant metabolite
australine australine: RN & structure given in first source; inhibits amyloglucosidase & glycoprotein processing	7.03	1	0
ritonavir Ritonavir: An HIV protease inhibitor that works by interfering with the reproductive cycle of HIV. It also inhibits CYTOCHROME P-450 CYP3A.. ritonavir : An L-valine derivative that is L-valinamide in which alpha-amino group has been acylated by a [(2-isopropyl-1,3-thiazol-4-yl)methyl]methylcarbamoyl group and in which a hydrogen of the carboxamide amino group has been replaced by a (2R,4S,5S)-4-hydroxy-1,6-diphenyl-5-{[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}hexan-2-yl group. A CYP3A inhibitor and antiretroviral drug from the protease inhibitor class used to treat HIV infection and AIDS, it is often used as a fixed-dose combination with another protease inhibitor, lopinavir. Also used in combination with dasabuvir sodium hydrate, ombitasvir and paritaprevir (under the trade name Viekira Pak) for treatment of chronic hepatitis C virus genotype 1 infection as well as cirrhosis of the liver.	4.61	1	1	1,3-thiazoles; carbamate ester; carboxamide; L-valine derivative; ureas	antiviral drug; environmental contaminant; HIV protease inhibitor; xenobiotic
germine germine: alkamine; present in many polyester alkaloids which occur in Veratrum & Zydadenus species; may be used medically as an antihypertensive agent; minor descriptor (75-83); on-line & Index Medicus search CEVANES (75-83); RN given refers to parent cpd; structure	2.48	2	0
permanganate [no description available]	4.61	1	1	manganese oxoacid
leupeptins Leupeptins: A group of acylated oligopeptides produced by Actinomycetes that function as protease inhibitors. They have been known to inhibit to varying degrees trypsin, plasmin, KALLIKREINS, papain and the cathepsins.	2.52	2	0
carboplatin [no description available]	4.61	1	1
1,3,5-triaminocyclohexane 1,3,5-triaminocyclohexane: forms a complex with copper than can hydrolyze phosphoric esters; structure in first source	2.08	1	0
lithium chloride Lithium Chloride: A salt of lithium that has been used experimentally as an immunomodulator.. lithium chloride : A metal chloride salt with a Li(+) counterion.	2.96	4	0	inorganic chloride; lithium salt	antimanic drug; geroprotector
s-adenosylhomocysteine S-Adenosylhomocysteine: 5'-S-(3-Amino-3-carboxypropyl)-5'-thioadenosine. Formed from S-adenosylmethionine after transmethylation reactions.. S-adenosyl-L-homocysteine : An organic sulfide that is the S-adenosyl derivative of L-homocysteine.	2.08	1	0	adenosines; amino acid zwitterion; homocysteine derivative; homocysteines; organic sulfide	cofactor; EC 2.1.1.72 [site-specific DNA-methyltransferase (adenine-specific)] inhibitor; EC 2.1.1.79 (cyclopropane-fatty-acyl-phospholipid synthase) inhibitor; epitope; fundamental metabolite
5'-methylthioadenosine 5'-methylthioadenosine: structure. 5'-S-methyl-5'-thioadenosine : Adenosine with the hydroxy group at C-5' substituted with a methylthio (methylsulfanyl) group.	2.49	2	0	thioadenosine	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
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
arabinose [no description available]	2.05	1	0	L-arabinose	Escherichia coli metabolite; mouse metabolite
fibrin Fibrin: A protein derived from FIBRINOGEN in the presence of THROMBIN, which forms part of the blood clot.	6.92	1	0	peptide
polygalacturonic acid galacturonic acid: N1 same as NM; RN given refers to parent cpd with unspecified isomeric designation. D-galactopyranuronic acid : The pyranose form of D-galacturonic acid. D-galacturonic acid : The D-enantiomer of galacturonic acid. It is the main component of pectin.	2.71	3	0	D-galacturonic acid
mevalonic acid Mevalonic Acid: A dihydroxy monocarboxylic acid and precursor in the biosynthetic pathway known as the mevalonate pathway, which produces terpenes and steroids that are vital for diverse cellular functions.. mevalonic acid : A racemate composed of equimolar amounts of (R)- and (S)-mevalonic acid.. (R)-mevalonic acid : The (R)-enantiomer of mevalonic acid.	2.54	2	0	3,5-dihydroxy-3-methylpentanoic acid
ouabain Ouabain: A cardioactive glycoside consisting of rhamnose and ouabagenin, obtained from the seeds of Strophanthus gratus and other plants of the Apocynaceae; used like DIGITALIS. It is commonly used in cell biological studies as an inhibitor of the NA(+)-K(+)-EXCHANGING ATPASE.. cardiac glycoside : Steroid lactones containing sugar residues that act on the contractile force of the cardiac muscles.. ouabain : A steroid hormone that is a multi-hydroxylated alpha-L-rhamnosyl cardenoloide. It binds to and inhibits the plasma membrane Na(+)/K(+)-ATPase (sodium pump). It has been isolated naturally from Strophanthus gratus.	1.94	1	0	11alpha-hydroxy steroid; 14beta-hydroxy steroid; 5beta-hydroxy steroid; alpha-L-rhamnoside; cardenolide glycoside; steroid hormone	anti-arrhythmia drug; cardiotonic drug; EC 2.3.3.1 [citrate (Si)-synthase] inhibitor; EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; ion transport inhibitor; plant metabolite
allose [no description available]	2.04	1	0	allopyranose; D-allose	antioxidant
protochlorophyllide Protochlorophyllide: A photo-active pigment localized in prolamellar bodies occurring within the proplastids of dark-grown bean leaves. In the process of photoconversion, the highly fluorescent protochlorophyllide is converted to chlorophyll.. protochlorophyllide : An analogue of chlorophyll that lacks the phytol side-chain. The parent of the protochlorophyllide class.	2.1	1	0
fructans (2->6)-beta-D-fructan : A fructan compound consisting of repeating (2->6)-beta-linked fructofuranose units.	2.6	1	0
cellulase Cellulase: An endocellulase with specificity for the hydrolysis of 1,4-beta-glucosidic linkages in CELLULOSE, lichenin, and cereal beta-glucans.. beta-cellotriose : A cellotriose with a beta-configuration at the anomeric position.	4.36	20	0	cellotriose
psicose, (d)-isomer [no description available]	2.17	1	0	monosaccharide
strychnine Strychnine: An alkaloid found in the seeds of STRYCHNOS NUX-VOMICA. It is a competitive antagonist at glycine receptors and thus a convulsant. It has been used as an analeptic, in the treatment of nonketotic hyperglycinemia and sleep apnea, and as a rat poison.. strychnine : A monoterpenoid indole alkaloid that is strychnidine bearing a keto substituent at the 10-position.	3.12	1	0	monoterpenoid indole alkaloid; organic heteroheptacyclic compound	avicide; cholinergic antagonist; glycine receptor antagonist; neurotransmitter agent; rodenticide
quinidine Quinidine: An optical isomer of quinine, extracted from the bark of the CHINCHONA tree and similar plant species. This alkaloid dampens the excitability of cardiac and skeletal muscles by blocking sodium and potassium currents across cellular membranes. It prolongs cellular ACTION POTENTIALS, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission.. quinidine : A cinchona alkaloid consisting of cinchonine with the hydrogen at the 6-position of the quinoline ring substituted by methoxy.	2.04	1	0	cinchona alkaloid	alpha-adrenergic antagonist; anti-arrhythmia drug; antimalarial; drug allergen; EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor; EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor; muscarinic antagonist; P450 inhibitor; potassium channel blocker; sodium channel blocker
cefoxitin Cefoxitin: A semisynthetic cephamycin antibiotic resistant to beta-lactamase.. cefoxitin : A semisynthetic cephamycin antibiotic which, in addition to the methoxy group at the 7alpha position, has 2-thienylacetamido and carbamoyloxymethyl side-groups. It is resistant to beta-lactamase.	1.96	1	0	beta-lactam antibiotic allergen; cephalosporin; cephamycin; semisynthetic derivative	antibacterial drug
terconazole terconazole: structure & RN for (cis)-isomer from first source. terconazole : A racemate consisting of equimolar amounts of (2R,4S)- and (2S,4R)-terconazole. It has broad-spectrum antifungal activitiy and is used for the treatment of vaginal yeast infections (Candida).. (2R,4S)-terconazole : A 1-(4-{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-isopropylpiperazine in which positions 2 and 4 of the 1,3-dioxolane moiety have R and S configuration, respectively.	2.62	3	0	1-(4-{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-isopropylpiperazine
linezolid [no description available]	7.01	1	0	acetamides; morpholines; organofluorine compound; oxazolidinone	antibacterial drug; protein synthesis inhibitor
canaline canaline: structure	1.96	1	0	amino acid zwitterion; non-proteinogenic L-alpha-amino acid	antimetabolite; antineoplastic agent; phytogenic insecticide; plant metabolite
lenticin lenticin: found in extracts of lentils. hypaphorine : An amino acid betaine obtaine by exhaustive methylation of the alpha-amino group of L-tryptophan with concomitant deprotonation of the carboxy group.	2	1	0	amino-acid betaine; indole alkaloid; L-tryptophan derivative	fungal metabolite; plant metabolite; xenobiotic
altholactone altholactone: structure in first source	7.03	1	0	furopyran
lignans Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	2.21	1	0
2-c-methylerythritol 4-phosphate 2-C-methylerythritol 4-phosphate: structure in first source	2.49	2	0	tetritol phosphate	Escherichia coli metabolite
n-formylmethionine leucyl-phenylalanine N-Formylmethionine Leucyl-Phenylalanine: A formylated tripeptide originally isolated from bacterial filtrates that is positively chemotactic to polymorphonuclear leucocytes, and causes them to release lysosomal enzymes and become metabolically activated.. N-formyl-L-methionyl-L-leucyl-L-phenylalanine : A tripeptide composed of L-Met, L-Leu and L-Phe in a linear sequence with a formyl group at the amino terminus. It acts as a potent inducer of leucocyte chemotaxis and macrophage activator as well as a ligand for the FPR receptor.	2.05	1	0	tripeptide
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2.47	2	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.	4.32	2	2	butenedioic acid	algal metabolite; mouse metabolite; plant metabolite
e-z cinnamic acid cinnamic acid : A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.. trans-cinnamic acid : The E (trans) isomer of cinnamic acid	2	1	0	cinnamic acid	plant metabolite
ergosterol [no description available]	2.25	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; ergostanoid; phytosterols	fungal metabolite; Saccharomyces cerevisiae metabolite
trichostatin a trichostatin A: chelates zinc ion in the active site of histone deacetylases, resulting in preventing histone unpacking so DNA is less available for transcription; do not confuse with TRICHOSANTHIN which is a protein; found in STREPTOMYCES	2.08	1	0	antibiotic antifungal agent; hydroxamic acid; trichostatin	bacterial metabolite; EC 3.5.1.98 (histone deacetylase) inhibitor; geroprotector
tretinoin Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.	4.61	1	1	retinoic acid; vitamin A	anti-inflammatory agent; antineoplastic agent; antioxidant; AP-1 antagonist; human metabolite; keratolytic drug; retinoic acid receptor agonist; retinoid X receptor agonist; signalling molecule
alpha-cyclodextrin alpha-cyclodextrin : A cycloamylose composed of six alpha-(1->4) linked D-glucopyranose units.	2.13	1	0	cyclodextrin
fumaric acid fumaric acid: see also record for ferrous fumarate; use FUMARATES for general fumaric acid esters. fumaric acid : A butenedioic acid in which the C=C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle.	2.01	1	0	butenedioic acid	food acidity regulator; fundamental metabolite; geroprotector
3-hydroxy-3-methylglutaryl-coenzyme a 3-hydroxy-3-methylglutaryl-coenzyme A: RN given refers to cpd without isomeric designation. 3-hydroxy-3-methylglutaryl-CoA : An alpha,omega dicarboxyacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with one of the carboxy groups of 3-hydroxy-3-methylglutaric acid.. (3S)-3-hydroxy-3-methylglutaryl-CoA : A 3-hydroxy-3-methylglutaryl-CoA where the 3-hydroxy-3-methylglutaryl component has (S)-configuration.	2.15	1	0	3-hydroxy-3-methylglutaryl-CoA; 3-hydroxy fatty acyl-CoA	human metabolite; mouse metabolite
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	2.44	2	0	resveratrol	antioxidant; phytoalexin; plant metabolite; quorum sensing inhibitor; radical scavenger
retinol Vitamin A: Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of CAROTENOIDS found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.. vitamin A : Any member of a group of fat-soluble retinoids produced via metabolism of provitamin A carotenoids that exhibit biological activity against vitamin A deficiency. Vitamin A is involved in immune function, vision, reproduction, and cellular communication.. all-trans-retinol : A retinol in which all four exocyclic double bonds have E- (trans-) geometry.. retinol : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraen-1-ol substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).	1.93	1	0	retinol; vitamin A	human metabolite; mouse metabolite; plant 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.	2.4	2	0	octadec-9-enoic acid	antioxidant; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; mouse metabolite; plant metabolite; solvent
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	2.74	3	0	ferulic acids	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; MALDI matrix material; plant metabolite
pectins Pectins: High molecular weight polysaccharides present in the cell walls of all plants. Pectins cement cell walls together. They are used as emulsifiers and stabilizers in the food industry. They have been tried for a variety of therapeutic uses including as antidiarrheals, where they are now generally considered ineffective, and in the treatment of hypercholesterolemia.. alpha-D-galacturonic acid : The alpha-anomer of D-galacturonic acid.	5.74	24	0	D-galactopyranuronic acid
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.	2.04	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
eicosapentaenoic acid icosapentaenoic acid : Any straight-chain, C20 polyunsaturated fatty acid having five C=C double bonds.. all-cis-5,8,11,14,17-icosapentaenoic acid : An icosapentaenoic acid having five cis-double bonds at positions 5, 8, 11, 14 and 17.	2.46	2	0	icosapentaenoic acid; omega-3 fatty acid	anticholesteremic drug; antidepressant; antineoplastic agent; Daphnia galeata metabolite; fungal metabolite; micronutrient; mouse metabolite; nutraceutical
lycopene [no description available]	4.57	24	0	acyclic carotene	antioxidant; plant metabolite
zithromax Azithromycin: A semi-synthetic macrolide antibiotic structurally related to ERYTHROMYCIN. It has been used in the treatment of Mycobacterium avium intracellulare infections, toxoplasmosis, and cryptosporidiosis.. azithromycin : A macrolide antibiotic useful for the treatment of bacterial infections.	2.04	1	0	macrolide antibiotic	antibacterial drug; environmental contaminant; xenobiotic
violaxanthin violaxanthin: a carotene epoxide that is precursor to capsanthin; one of 3 xanthophylls involved in evolution of plastids of green plants (oxygen evolution); 3 (violaxanthin, zeaxanthin & antheraxanthin) participate in series of photo-induced interconversions known as ''violaxanthin cycle''; structure; cleavage of 9-cis-epoxycarotenoids (violaxanthin) to xanthoxin, catalyzed by 9-cis-epoxycarotenoid dioxygenase, is the key regulatory step of ABSCISIC ACID biosynthesis. violaxanthin : An epoxycarotenol that is 5,5',6,6'-tetrahydro-5,6:5',6'-diepoxy-beta,beta-carotene substituted by hydroxy groups at positions 3 and 3'. It is the naturally occurring xanthophyll pigment found in a variety of plants.. all-trans-violaxanthin : The all-trans-stereoisomer of violaxanthin.	2.11	1	0	violaxanthin	food colouring
diethylstilbestrol Diethylstilbestrol: A synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen. (Merck, 11th ed). diethylstilbestrol : An olefinic compound that is trans-hex-3-ene in which the hydrogens at positions 3 and 4 have been replaced by p-hydroxyphenyl groups.	1.93	1	0	olefinic compound; polyphenol	antifungal agent; antineoplastic agent; autophagy inducer; calcium channel blocker; carcinogenic agent; EC 1.1.1.146 (11beta-hydroxysteroid dehydrogenase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; endocrine disruptor; xenoestrogen
zeatin Zeatin: An aminopurine factor in plant extracts that induces cell division. (Grant & Hackh's Chemical Dict, 5th ed)	2.95	4	0	zeatin	plant metabolite
imidazolidines [no description available]	2.73	3	0	azacycloalkane; imidazolidines; saturated organic heteromonocyclic parent
iridoids Iridoids: A type of MONOTERPENES, derived from geraniol. They have the general form of cyclopentanopyran, but in some cases, one of the rings is broken as in the case of secoiridoid. They are different from the similarly named iridals (TRITERPENES).	2.03	1	0
dactinomycin Dactinomycin: A compound composed of a two CYCLIC PEPTIDES attached to a phenoxazine that is derived from STREPTOMYCES parvullus. It binds to DNA and inhibits RNA synthesis (transcription), with chain elongation more sensitive than initiation, termination, or release. As a result of impaired mRNA production, protein synthesis also declines after dactinomycin therapy. (From AMA Drug Evaluations Annual, 1993, p2015)	2.39	2	0	actinomycin	mutagen
gamma-sitosterol clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.	2.06	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols	marine metabolite; plant metabolite
aphidicolin Aphidicolin: An antiviral antibiotic produced by Cephalosporium aphidicola and other fungi. It inhibits the growth of eukaryotic cells and certain animal viruses by selectively inhibiting the cellular replication of DNA polymerase II or the viral-induced DNA polymerases. The drug may be useful for controlling excessive cell proliferation in patients with cancer, psoriasis or other dermatitis with little or no adverse effect upon non-multiplying cells.. aphidicolin : A tetracyclic diterpenoid that has an tetradecahydro-8,11a-methanocyclohepta[a]naphthalene skeleton with two hydroxymethyl substituents at positions 4 and 9, two methyl substituents at positions 4 and 11b and two hydroxy substituents at positions 3 and 9. An antibiotic with antiviral and antimitotical properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication.	2.41	2	0	tetracyclic diterpenoid	antimicrobial agent; antimitotic; antineoplastic agent; antiviral drug; apoptosis inducer; Aspergillus metabolite; DNA synthesis inhibitor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; fungal metabolite
benzyloxycarbonylleucyl-leucyl-leucine aldehyde benzyloxycarbonylleucyl-leucyl-leucine aldehyde: proteasome inhibitor. N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal : A tripeptide that is L-leucyl-L-leucyl-L-leucine in which the C-terminal carboxy group has been reduced to the corresponding aldehyde and the N-terminal amino group is protected as its benzyloxycarbonyl derivative.	2.52	2	0	amino aldehyde; carbamate ester; tripeptide	proteasome inhibitor
shikonin shikonin: a naphthazarin; has antineoplastic and angiogenesis inhibiting activities	2.98	4	0	hydroxy-1,4-naphthoquinone
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).	2.4	2	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
2,3-bis(bromomethyl)quinoxaline-1,4-dioxide conoidin A: inhibits the peroxiredoxin TgPrx11; structure in first source	4.61	1	1
potassium permanganate Potassium Permanganate: Permanganic acid (HMnO4), potassium salt. A highly oxidative, water-soluble compound with purple crystals, and a sweet taste. (From McGraw-Hill Dictionary of Scientific and Technical Information, 4th ed)	2.99	4	0
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.	4.09	3	1	one-carbon compound; organic sodium salt	antacid; food anticaking agent
sodium benzoate Sodium Benzoate: The sodium salt of BENZOIC ACID. It is used as an antifungal preservative in pharmaceutical preparations and foods. It may also be used as a test for liver function.. sodium benzoate : An organic sodium salt resulting from the replacement of the proton from the carboxy group of benzoic acid by a sodium ion.	2.43	2	0	organic sodium salt	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
potassium fluoride potassium fluoride : A fluoride salt having K+ as the counterion.	2.03	1	0	fluoride salt; potassium salt	NMR chemical shift reference compound; poison
tris(perfluorophenyl)borane tris(perfluorophenyl)borane: structure in first source	2.11	1	0
camalexin camalexin : An indole phytoalexin that is indole substituted at position 3 by a 1,3-thiazol-2-yl group.	5.58	22	0	1,3-thiazoles; indole phytoalexin	metabolite
elaidic acid [no description available]	1.98	1	0	octadec-9-enoic acid	food component
geraniol [no description available]	2.08	1	0	3,7-dimethylocta-2,6-dien-1-ol; monoterpenoid; primary alcohol	allergen; fragrance; plant metabolite; volatile oil component
glycosides [no description available]	3.74	10	0
chalcone trans-chalcone : The trans-isomer of chalcone.	7.1	1	0	chalcone	EC 3.2.1.1 (alpha-amylase) inhibitor
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.	2.01	1	0	sinapic acid	MALDI matrix material; plant metabolite
citral citral: Xref geranial: geraniol is also available; Xref neral: nerol is also available; vitamin A antagonist; oxygenated monoterpene; inhibits cytosolic dehydrogenases; structure. citral : An enal that consists of octa-2,6-dienal bearing methyl substituents at positions 3 and 7. A mixture of the two geometric isomers geranial and neral, it is the major constituent (75-85%) of oil of lemon grass, the volatile oil of Cymbopogon citratus, or of C. flexuosus. It also occurs in oils of verbena, lemon, and orange.	7.08	1	0	enal; monoterpenoid; polyprenal	plant metabolite; volatile oil component
retinaldehyde Retinaldehyde: A diterpene derived from the carotenoid VITAMIN A which functions as the active component of the visual cycle. It is the prosthetic group of RHODOPSIN (i.e., covalently bonded to ROD OPSIN as 11-cis-retinal). When stimulated by visible light, rhodopsin transforms this cis-isomer of retinal to the trans-isomer (11-trans-retinal). This transformation straightens-out the bend of the retinal molecule and causes a change in the shape of rhodopsin triggering the visual process. A series of energy-requiring enzyme-catalyzed reactions convert the 11-trans-retinal back to the cis-isomer.. all-trans-retinal : A retinal in which all four exocyclic double bonds have E- (trans-) geometry.	1.93	1	0	retinal; vitamin A	gap junctional intercellular communication inhibitor; human metabolite; mouse metabolite
squalene Addavax: an oil-water nanoemulsion and adjuvant containing squalene, Tween 80, and sorbitane trioleate	2.59	2	0	triterpene	human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	3.87	12	0	stilbene
flavin-adenine dinucleotide Flavin-Adenine Dinucleotide: A condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972)	1.96	1	0	flavin adenine dinucleotide; vitamin B2	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; prosthetic group
cannabidiol Cannabidiol: Compound isolated from Cannabis sativa extract.. cannabidiol : An cannabinoid that is cyclohexene which is substituted by a methyl group at position 1, a 2,6-dihydroxy-4-pentylphenyl group at position 3, and a prop-1-en-2-yl group at position 4.	2.31	1	0	olefinic compound; phytocannabinoid; resorcinols	antimicrobial agent; plant metabolite
pyrophosphate Diphosphates: Inorganic salts of phosphoric acid that contain two phosphate groups.	4.32	2	2	diphosphate ion
glucobrassicin glucobrassicin: isolated from Brussels sprouts; structure given in first source. glucobrassicin : An indolylmethylglucosinolic acid that is 1-thio-beta-D-glucopyranose having a 2-(1H-indol-3-yl)-N-(sulfooxy)ethanimidoyl group attached to the anomeric sulfur.	2.45	2	0	indolyl carbohydrate; indolylmethylglucosinolic acid
4-methoxy-3-indolylmethyl glucosinolate 4-methoxy-3-indolylmethyl glucosinolate: from cabbage, cauliflower & brussels sprouts. 4-methoxyglucobrassicin : An indolylmethylglucosinolic acid that is glucobrassicin bearing a methoxy substituent at position 4 on the indole ring.	2.05	1	0	indolyl carbohydrate; indolylmethylglucosinolic acid
polidocanol Polidocanol: An alkyl polyglycol ether of LAURYL ALCOHOL, chemically defined as an alcohol ethoxylate having an average alkyl chain of 12–14 carbon atoms, and an ethylene oxide chain of 9 ethylene oxide units. It is used as a detergent, and medically as a local anesthetic, and as a sclerosing agent for the treatment of ESOPHAGEAL AND GASTRIC VARICES and VARICOSE VEINS.. polidocanol : A hydroxypolyether that is nonaethylene glycol in which one of the terminal hydroxy functions is substituted by a lauryl (dodecyl) group.	1.93	1	0	hydroxypolyether	hepatotoxic agent; nonionic surfactant; sclerotherapy agent
sesquiterpenes [no description available]	5.7	25	0
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	2.44	2	0	caffeic acid	geroprotector; mouse metabolite
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.	2.04	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.	2.02	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
pyrabactin pyrabactin: structure in first source. pyrabactin : A sulfonamide obtained by formal condensation of the sulfo group of 4-bromonaphthalene-1-sulfonic acid with the exocyclic amino group of 2-pyridylmethylamine. Mimics the action of the abscisic acid, a phytohormone.	2.11	1	0	naphthalenes; organobromine compound; pyridines; sulfonamide	abscisic acid receptor agonist; hormone; plant growth regulator
capsaicin ALGRX-4975: an injectable capsaicin (TRPV1 receptor agonist) formulation for longlasting pain relief. capsaicinoid : A family of aromatic fatty amides produced as secondary metabolites by chilli peppers.	2.01	1	0	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
terbinafine [no description available]	2.04	1	0	acetylenic compound; allylamine antifungal drug; enyne; naphthalenes; tertiary amine	EC 1.14.13.132 (squalene monooxygenase) inhibitor; P450 inhibitor; sterol biosynthesis inhibitor
coniferyl alcohol coniferyl alcohol: structure. coniferol : A phenylpropanoid that is one of the main monolignols, produced by the reduction of the carboxy functional group in cinnamic acid and the addition of a hydroxy and a methoxy substituent to the aromatic ring.	2.03	1	0	guaiacols; phenylpropanoid	animal metabolite; monolignol; mouse metabolite; pheromone; plant metabolite; volatile oil component
geranylacetone geranyl acetone : A monoterpene ketone in which an (E)-geranyl group is bonded to one of the alpha-methyls of acetone. It is a component of essential oils from various plants including Nelumbo nucifera.	2.04	1	0	monoterpene ketone	flavouring agent; fragrance; plant metabolite; volatile oil component
chlorogenic acid caffeoylquinic acid: Antiviral Agent; structure in first source. chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3.	2.52	2	0	cinnamate ester; tannin	food component; plant metabolite
thioguanine anhydrous Thioguanine: An antineoplastic compound which also has antimetabolite action. The drug is used in the therapy of acute leukemia.. tioguanine : A 2-aminopurine that is the 6-thiono derivative of 2-amino-1,9-dihydro-6H-purine. Incorporates into DNA and inhibits synthesis. Used in the treatment of leukaemia.	2.13	1	0	2-aminopurines	anticoronaviral agent; antimetabolite; antineoplastic agent
thiobarbituric acid thiobarbituric acid: RN given refers to parent cpd. 2-thiobarbituric acid : A barbiturate, the structure of which is that of barbituric acid in which the oxygen at C-2 is replaced by sulfur.	2.44	2	0	barbiturates	allergen; reagent
1,3-dimethylthiourea [no description available]	2.96	4	0
thiourea Thiourea: A photographic fixative used also in the manufacture of resins. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance may reasonably be anticipated to be a carcinogen (Merck Index, 9th ed). Many of its derivatives are ANTITHYROID AGENTS and/or FREE RADICAL SCAVENGERS.. thiourea : The simplest member of the thiourea class, consisting of urea with the oxygen atom substituted by sulfur.	3.28	6	0	one-carbon compound; thioureas; ureas	antioxidant; chromophore
D-fructopyranose [no description available]	3.31	6	0	cyclic hemiketal; D-fructose; fructopyranose	sweetening agent
thioacetamide Thioacetamide: A crystalline compound used as a laboratory reagent in place of HYDROGEN SULFIDE. It is a potent hepatocarcinogen.. thioacetamide : A thiocarboxamide consiting of acetamide having the oxygen replaced by sulfur.	2.01	1	0	thiocarboxamide	hepatotoxic agent
digoxin Digoxin: A cardiotonic glycoside obtained mainly from Digitalis lanata; it consists of three sugars and the aglycone DIGOXIGENIN. Digoxin has positive inotropic and negative chronotropic activity. It is used to control ventricular rate in ATRIAL FIBRILLATION and in the management of congestive heart failure with atrial fibrillation. Its use in congestive heart failure and sinus rhythm is less certain. The margin between toxic and therapeutic doses is small. (From Martindale, The Extra Pharmacopoeia, 30th ed, p666). digoxin : A cardenolide glycoside that is digitoxin beta-hydroxylated at C-12. A cardiac glycoside extracted from the foxglove plant, Digitalis lanata, it is used to control ventricular rate in atrial fibrillation and in the management of congestive heart failure with atrial fibrillation, but the margin between toxic and therapeutic doses is small.	2.04	1	0	cardenolide glycoside; steroid saponin	anti-arrhythmia drug; cardiotonic drug; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; epitope
fumonisin b1 fumonisin B1: isolated from Fusarium moniliforme MRC 826; structure given in first source; has cancer-promoting activity; inhibits ceramide synthase. fumonisin B1 : A diester that results from the condensation of the 1-carboxy groups of two molecules of propane-1,2,3-tricarboxylic acid with hydroxy groups at positions 14 and 15 of (2S,3S,5R,10R,12S,14S,15R,16R)-2-amino-12,16-dimethylicosane-3,5,10,14,15-pentol.	7.73	3	0	diester; fumonisin; primary amino compound; triol	carcinogenic agent; metabolite
1,3-dihydroxy-4,4,5,5-tetramethyl-2-(4-carboxyphenyl)tetrahydroimidazole 1,3-dihydroxy-4,4,5,5-tetramethyl-2-(4-carboxyphenyl)tetrahydroimidazole: intermediate in the synthesis of imidazolineoxyl N-oxides; partial structure given in first source	2.5	2	0	benzoic acid; imidazolines; organic radical	apoptosis inhibitor; radical scavenger
2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide: partial structure given in first source; endothelium-derived relaxing factor antagonist	2.08	1	0
nadp [no description available]	3.68	10	0
scandium triflate scandium triflate: structure in first source	2.03	1	0
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)	2.05	1	0
3,4-diaminocyclobut-3-ene-1,2-dione 3,4-diaminocyclobut-3-ene-1,2-dione: structure in first source	3.41	1	0
tetrachlorodecaoxide tetrachlorodecaoxide: stimulates wound healing; consists of chlorine, oxygen complexes	1.96	1	0
thiopental Thiopental: A barbiturate that is administered intravenously for the induction of general anesthesia or for the production of complete anesthesia of short duration.. thiopental : A barbiturate, the structure of which is that of 2-thiobarbituric acid substituted at C-5 by ethyl and sec-pentyl groups.	2.04	1	0	barbiturates	anticonvulsant; drug allergen; environmental contaminant; intravenous anaesthetic; sedative; xenobiotic
u 0126 U 0126: protein kinase kinase inhibitor; structure in first source	2.08	1	0	aryl sulfide; dinitrile; enamine; substituted aniline	antineoplastic agent; antioxidant; apoptosis inducer; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; osteogenesis regulator; vasoconstrictor agent
lithium Lithium: An element in the alkali metals family. It has the atomic symbol Li, atomic number 3, and atomic weight [6.938; 6.997]. Salts of lithium are used in treating BIPOLAR DISORDER.	3.29	6	0	alkali metal atom
n-ethylthiourea [no description available]	1.96	1	0	thioureas
cobaltous chloride cobaltous chloride: RN given refers to unlabeled cpd; RN in Chemline for cobalt trichloride: 10241-04-0; RN for 60-labeled cpd: 14543-09-0; RN for 57-labeled cpd: 164113-89-1; RN for 58-labeled cpd: 29377-09-1; structure. cobalt dichloride : A cobalt salt in which the cobalt metal is in the +2 oxidation state and the counter-anion is chloride. It is used as an indicator for water in desiccants.	3.95	13	0	cobalt salt; inorganic chloride	allergen; calcium channel blocker; sensitiser; two-colour indicator
nitrogen dioxide Nitrogen Dioxide: Nitrogen oxide (NO2). A highly poisonous gas. Exposure produces inflammation of lungs that may only cause slight pain or pass unnoticed, but resulting edema several days later may cause death. (From Merck, 11th ed) It is a major atmospheric pollutant that is able to absorb UV light that does not reach the earth's surface.	5.17	3	1	nitrogen oxide
quinine [no description available]	3.41	1	0	cinchona alkaloid	antimalarial; muscle relaxant; non-narcotic analgesic
methyl radical [no description available]	2.11	1	0	organic radical
mercuric perchlorate [no description available]	1.97	1	0
5-nitroso-salicylate 5-nitroso-salicylate: metabolite of 5-aminosalicylic acid	1.96	1	0	hydroxybenzoic acid
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.	2.02	1	0
amanitins Amanitins: Cyclic peptides extracted from carpophores of various mushroom species. They are potent inhibitors of RNA polymerases in most eukaryotic species, blocking the production of mRNA and protein synthesis. These peptides are important in the study of transcription. Alpha-amanitin is the main toxin from the species Amanitia phalloides, poisonous if ingested by humans or animals.	2.03	1	0
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	2.06	1	0
phosphonic acid phosphonic acid : A phosphorus oxoacid that consists of a single pentavalent phosphorus covalently bound via single bonds to a single hydrogen and two hydroxy groups and via a double bond to an oxygen. The parent of the class of phosphonic acids.	2.08	1	0
crocin crocin: a free radical scavenger	2.38	2	0
bemp phosphazene BEMP phosphazene: structure in first source	2.08	1	0
galactomannan galactomannan: a galectin inhibitor. galactomannan : A heteroglycan consisting of a mannan backbone with galactose side groups.	2.05	1	0	oligosaccharide
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.	1.94	1	0
niobium carbide niobium carbide: found in some gypsum-bonded dental investments	2.05	1	0
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	2.98	4	0
sodium borohydride sodium borohydride: RN given refers to parent cpd	2.06	1	0	inorganic sodium salt; metal tetrahydridoborate
alpha-carotene alpha-carotene: RN given refers to (all-E)-isomer; see also related record beta-carotene. alpha-carotene : A cyclic carotene with a beta- and an epsilon-ring at opposite ends respectively.	2.15	1	0	carotenoid beta-end derivative; cyclic carotene	plant metabolite; provitamin A
2-amino-4-(2-aminoethoxy)butanoic acid 2-amino-4-(2-aminoethoxy)butanoic acid: RN given refers to cpd without isomeric designation; structure	3.4	7	0
myelin basic protein Myelin Basic Protein: An abundant cytosolic protein that plays a critical role in the structure of multilamellar myelin. Myelin basic protein binds to the cytosolic sides of myelin cell membranes and causes a tight adhesion between opposing cell membranes.	2	1	0
9-mesityl-10-methylacridinium 9-mesityl-10-methylacridinium: structure in first source	2.07	1	0
sphingosine sphing-4-enine : A sphingenine in which the C=C double bond is located at the 4-position.. sphingenine : A 2-aminooctadecene-1,3-diol having (2S,3R)-configuration.. sphingoid : Sphinganine, its homologs and stereoisomers, and the hydroxy and unsaturated derivatives of these compounds.. 2-aminooctadec-4-ene-1,3-diol : A 2-aminooctadecene-1,3-diol having its double bond at position 4.	3.14	5	0	sphing-4-enine	human metabolite; mouse metabolite
quercetin [no description available]	2.53	2	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
12-oxophytodienoic acid 12-oxophytodienoic acid: structure given in first source; a jasmonate precursor that induces phytoalexin synthesis	3.43	7	0	carbocyclic fatty acid; olefinic fatty acid; oxo carboxylic acid
linoleic acid Linoleic Acid: A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed). linoleic acid : An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.	2.44	2	0	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
calcitriol dihydroxy-vitamin D3: as a major in vitro metabolite of 1alpha,25-dihydroxyvitamin D3, produced in primary cultures of neonatal human keratinocytes	2.13	1	0	D3 vitamins; hydroxycalciol; triol	antineoplastic agent; antipsoriatic; bone density conservation agent; calcium channel agonist; calcium channel modulator; hormone; human metabolite; immunomodulator; metabolite; mouse metabolite; nutraceutical
pinosylvin pinosylvin: phytoalexin found in pine and eucalyptus	2.01	1	0	pinosylvin
scopoletin [no description available]	2.07	1	0	hydroxycoumarin	plant growth regulator; plant metabolite
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.	1.96	1	0
beta carotene beta Carotene: A carotenoid that is a precursor of VITAMIN A. Beta carotene is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (PORPHYRIA, ERYTHROPOIETIC).. provitamin A : A provitamin that can be converted into vitamin A by enzymes from animal tissues.	3.47	7	0	carotenoid beta-end derivative; cyclic carotene	antioxidant; biological pigment; cofactor; ferroptosis inhibitor; human metabolite; mouse metabolite; plant metabolite; provitamin A
11-cis-retinal Rhodopsin: A purplish-red, light-sensitive pigment found in RETINAL ROD CELLS of most vertebrates. It is a complex consisting of a molecule of ROD OPSIN and a molecule of 11-cis retinal (RETINALDEHYDE). Rhodopsin exhibits peak absorption wavelength at about 500 nm.. 11-cis-retinal : A retinal having 2E,4Z,6E,8E-double bond geometry.	2.15	1	0	retinal	chromophore; human metabolite; mouse metabolite
coniferaldehyde coniferaldehyde: from aqueous extract of Senra incana. coniferyl aldehyde : A member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and a methoxy group at position 3.	2.03	1	0	cinnamaldehydes; guaiacols; phenylpropanoid	antifungal agent; plant metabolite
feruloyltyramine feruloyltyramine: structure given in first source; isolated from Cannabis sativa seeds, roots, leaves, and resin; induces hypothermia and motor incoordination in mice; moupinamide is (E)-isomer	2.49	2	0	tyramines	metabolite
(all-e) phytoene (all-E) phytoene: C40 carotenoid biosynthesized in bacteria; minor descriptor (75-84); EP to CAROTENOIDS (85); on-line & Index Medicus search CAROTENOIDS (75-85); RN given refers to (all-trans)-isomer; RN for cpd without isomeric designation. all-trans-phytoene : The all-trans-isomer of phytoene.	2.03	1	0	phytoene	plant metabolite
cholecalciferol Cholecalciferol: Derivative of 7-dehydroxycholesterol formed by ULTRAVIOLET RAYS breaking of the C9-C10 bond. It differs from ERGOCALCIFEROL in having a single bond between C22 and C23 and lacking a methyl group at C24.. calciol : A hydroxy seco-steroid that is (5Z,7E)-9,10-secocholesta-5,7,10(19)-triene in which the pro-S hydrogen at position 3 has been replaced by a hydroxy group. It is the inactive form of vitamin D3, being hydroxylated in the liver to calcidiol (25-hydroxyvitamin D3), which is then further hydroxylated in the kidney to give calcitriol (1,25-dihydroxyvitamin D3), the active hormone.	4.61	1	1	D3 vitamins; hydroxy seco-steroid; seco-cholestane; secondary alcohol; steroid hormone	geroprotector; human metabolite
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	2.47	2	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
kaempferol [no description available]	2.31	1	0	7-hydroxyflavonol; flavonols; tetrahydroxyflavone	antibacterial agent; geroprotector; human blood serum metabolite; human urinary metabolite; human xenobiotic metabolite; plant metabolite
zeaxanthin Zeaxanthins: Carotenoids found in fruits and vegetables. Zeaxanthin accumulates in the MACULA LUTEA.	2.55	2	0	carotenol	antioxidant; bacterial metabolite; cofactor
alpha-linolenic acid linolenic acid : A two-membered subclass of octadecatrienoic acid comprising the (9Z,12Z,15Z)- and (6Z,9Z,12Z)-isomers. Linolenic acids are nutrients essential to the formation of prostaglandins and are also used in making paints and synthetic resins.. linolenate : A polyunsaturated fatty acid anion obtained by deprotonation of the carboxy group of either alpha- or gamma-linolenic acid.	4.38	6	0	linolenic acid; omega-3 fatty acid	micronutrient; mouse metabolite; nutraceutical
genistein [no description available]	2.49	2	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
clavulanic acid Clavulanic Acid: A beta-lactam antibiotic produced by the actinobacterium Streptomyces clavuligerus. It is a suicide inhibitor of bacterial beta-lactamase enzymes. Administered alone, it has only weak antibacterial activity against most organisms, but given in combination with other beta-lactam antibiotics it prevents antibiotic inactivation by microbial lactamase.. clavulanate : The conjugate base of clavulanic acid.. clavulanic acid : Antibiotic isolated from Streptomyces clavuligerus. It acts as a suicide inhibitor of bacterial beta-lactamase enzymes.	3.1	1	0	oxapenam	antibacterial drug; anxiolytic drug; bacterial metabolite; EC 3.5.2.6 (beta-lactamase) inhibitor
pulmicort Budesonide: A glucocorticoid used in the management of ASTHMA, the treatment of various skin disorders, and allergic RHINITIS.. budesonide : A glucocorticoid steroid having a highly oxygenated pregna-1,4-diene structure. It is used mainly in the treatment of asthma and non-infectious rhinitis and for treatment and prevention of nasal polyposis.	2.04	1	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; cyclic acetal; glucocorticoid; primary alpha-hydroxy ketone	anti-inflammatory drug; bronchodilator agent; drug allergen
jasmonic acid jasmonic acid: a derivative of alpha-linolenic acid that has a role in plant response to herbivory analogous to the role of prostanoids in inflammation in mammals;. jasmonic acid : An oxo monocarboxylic acid that is (3-oxocyclopentyl)acetic acid substituted by a (2Z)-pent-2-en-1-yl group at position 2 of the cyclopentane ring.	12.28	519	0	oxo monocarboxylic acid	jasmonates; plant metabolite
2-hexenal, z-isomer 2-hexenal: product of lipid peroxidation in the rat liver; a green odor chemical; do not confuse with the hexabarbital synonym, hexenal; RN given refers to cpd without isomeric designation. 2-hexenal : A hexenal having the double bond at the 2-position.. (2E)-hexenal : A 2-hexenal in which the olefinic double bond has E configuration. It occurs naturally in a wide range of fruits, vegetables, and spices.	2.04	1	0	2-hexenal	antibacterial agent; flavouring agent; plant metabolite
astaxanthine astaxanthine: a keto form of carotene; pigment in flesh of Scottish salmon (Salmo salar) crustacoa-lobster (Homarus gammarus, flamingo feathers; structure; a carotenoid without vitamin A activity, has shown anti-oxidant and anti-inflammatory activities. astaxanthin : A carotenone that consists of beta,beta-carotene-4,4'-dione bearing two hydroxy substituents at positions 3 and 3' (the 3S,3'S diastereomer). A carotenoid pigment found mainly in animals (crustaceans, echinoderms) but also occurring in plants. It can occur free (as a red pigment), as an ester, or as a blue, brown or green chromoprotein.	2.87	3	0	carotenol; carotenone	animal metabolite; anticoagulant; antioxidant; food colouring; plant metabolite
cryptoxanthins Cryptoxanthins: Mono-hydroxylated xanthophylls formed from the hydroxylation of BETA-CAROTENE. Isomers include: beta-cryptoxanthin, alpha-cryptoxanthin, and zeinoxanthin. The alpha- and beta-cryptoxanthin are provitamin A precursors.. beta-cryptoxanthin : A carotenol that exhibits antioxidant activity. It has been isolated from fruits such as papaya and oranges.	2.08	1	0	carotenol	antioxidant; biomarker; plant metabolite; provitamin A
lutein Lutein: A xanthophyll found in the major LIGHT-HARVESTING PROTEIN COMPLEXES of plants. Dietary lutein accumulates in the MACULA LUTEA.. xanthophyll : A subclass of carotenoids consisting of the oxygenated carotenes.	2.05	1	0	carotenol	food colouring; plant metabolite
genistin genistin: glycoside of soy bean isoflavone, gentistein	2.13	1	0	7-hydroxyisoflavones 7-O-beta-D-glucoside
strigol strigol: a strigolactone from roots of various PLANTS; it stimulates seed germination of parasitic STRIGA and OROBANCHE; structure in first source. strigol : A strigolactone in which the tricyclic lactone moiety bears a hydroxy substitutuent at the position para to the gem-dimethyl group.	7.11	1	0	indenofuran; secondary alcohol; strigolactone
esculin [no description available]	2.25	1	0	beta-D-glucoside; hydroxycoumarin	antioxidant; metabolite
alpha-farnesene alpha-farnesene: structure given in first source. alpha-farnesene : A farnesene that is 1,3,6,10-tetraene substituted by methyl groups at positions 3, 7 and 11 respectively.. farnesene : A sesquiterpene that is any of the four possible isomers of 3,7,11-trimethyl-1,3,6,10-dodecatetraene (alpha-farnesene) or of the two possible isomers of 7,11-dimethyl-3-methylene-1,6,10-dodecatriene.	8.29	6	0	alpha-farnesene
oleuropein oleuropein: iridoid isolated from leaves and fruit of Olea and Ligustrum (Oleaceae). oleuropein : A secoiridoid glycoside that is the methyl ester of 3,4-dihydro-2H-pyran-5-carboxylic acid which is substituted at positions 2, 3, and 4 by hydroxy, ethylidene, and carboxymethyl groups, respectively and in which the anomeric hydroxy group at position 2 has been converted into its beta-D-glucoside and the carboxylic acid moiety of the carboxymethyl substituent has been converted to the corresponding 3,4-dihydroxyphenethyl ester (the 2S,3E,4S stereoisomer). The most important phenolic compound present in olive cultivars.	2.03	1	0	beta-D-glucoside; catechols; diester; methyl ester; pyrans; secoiridoid glycoside	anti-inflammatory agent; antihypertensive agent; antineoplastic agent; antioxidant; apoptosis inducer; NF-kappaB inhibitor; nutraceutical; plant metabolite; radical scavenger
baicalein [no description available]	4.61	1	1	trihydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antibacterial agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antioxidant; apoptosis inducer; EC 1.13.11.31 (arachidonate 12-lipoxygenase) inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; EC 4.1.1.17 (ornithine decarboxylase) inhibitor; ferroptosis inhibitor; geroprotector; hormone antagonist; plant metabolite; prostaglandin antagonist; radical scavenger
mangiferin shamimin: isolated from the leaves of Bombax ceiba; structure in first source	2.17	1	0	C-glycosyl compound; xanthones	anti-inflammatory agent; antioxidant; hypoglycemic agent; plant metabolite
daidzein [no description available]	2.13	1	0	7-hydroxyisoflavones	antineoplastic agent; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; phytoestrogen; plant metabolite
feruloylputrescine feruloylputrescine: structure given in first source	2.25	1	0	hydroxycinnamic acid
menaquinone 6 menaquinone 6: RN given refers to (all-E)-isomer	4.61	1	1
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.	4.61	1	1	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
menaquinone 7 menaquinone-7 : A menaquinone whose side-chain contains seven isoprene units in an all-trans-configutation.	4.61	1	1	menaquinone	bone density conservation agent; cofactor; Escherichia coli metabolite; human blood serum metabolite; Mycoplasma genitalium metabolite
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.	2.05	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
pyoverdin pyoverdin: a partly cyclic octapeptide linked to a chromophore, derived from 2,3-diamino-6,7-dihydroxyquinoline, which confers color and fluorescence to the molecule; yellow-green pigment produced by Pseudomonas aeruginosa; pyoverdin Pf from P. fluorescens; structure has been determined	2.13	1	0
lysophosphatidylcholines lysophosphatidylcholine : An acylglycerophosphocholine resulting from partial hydrolysis of a phosphatidylcholine, which removes one of the fatty acyl groups. The structure is depicted in the image where R1 = acyl, R2 = H or where R1 = H, R2 = acyl.	2.1	1	0	1-O-acyl-sn-glycero-3-phosphocholine
cytochalasin b Cytochalasin B: A cytotoxic member of the CYTOCHALASINS.. cytochalasin B : An organic heterotricyclic compound, that is a mycotoxin which is cell permeable an an inhibitor of cytoplasmic division by blocking the formation of contractile microfilaments.	2.05	1	0	cytochalasin; lactam; lactone; organic heterotricyclic compound	actin polymerisation inhibitor; metabolite; mycotoxin; platelet aggregation inhibitor
1,2-oleoylphosphatidylcholine 1,2-oleoylphosphatidylcholine: RN given refers to (Z,Z)-isomer. dioleoyl phosphatidylcholine : A phosphatidylcholine in which the phosphatidyl acyl groups are both oleoyl.	1.99	1	0	phosphatidylcholine(1+)
biliverdine [no description available]	2.76	3	0
nerolidol nerolidol: sesquiterpene; RN given refers to cpd without isomeric designation; nerol is also available. nerolidol : A farnesane sesquiterpenoid that is dodeca-1,6,10-triene which carries methyl groups at positions 3, 7 and 11 and a hydroxy group at position 3. It is a natural product that is present in various flowers and plants with a floral odor. Chemically, it exists in two geometric isomers, trans and cis forms. It is widely used in cosmetics (e.g. shampoos and perfumes), in non-cosmetic products (e.g. detergents and cleansers) and also as a food flavoring agent.. (6Z)-nerolidol : A nerolidol in which the double bond at position 6 adopts a cis-configuration.	2.02	1	0	nerolidol
caryophyllene caryophyllene: RN given refers to cpd without isomeric designation; structure given in first source	2.07	1	0
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.	2.17	1	0	7,8-dimethylbenzo[g]pteridine-2,4-dione	plant metabolite
sclareolide sclareolide: has antineoplastic activity; synthesized by oxidation of sclareol; a minor constituent of Arnica angustifolia and Sideritis nutans; structure in first source	2.01	1	0
mitoguazone Mitoguazone: Antineoplastic agent effective against myelogenous leukemia in experimental animals. Also acts as an inhibitor of animal S-adenosylmethionine decarboxylase.. mitoguazone : A hydrazone obtained by formal condensation of the two carbonyl groups of methylglyoxal with the primary amino groups of two molecules of aminoguanidine.	2.07	1	0	guanidines; hydrazone	antineoplastic agent; apoptosis inducer; EC 4.1.1.50 (adenosylmethionine decarboxylase) inhibitor
fosbretabulin fosbretabulin: a microtubule destabilizing agent isolated from Combretum caffrum; structure in first source	2.04	1	0
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	5.54	4	1	carbon group element atom; elemental lead; metal atom	neurotoxin
tin [no description available]	7.98	4	0	carbon group element atom; elemental tin; metal atom	micronutrient
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	1	0	metalloid atom; pnictogen
cesium Cesium: A member of the alkali metals. It has an atomic symbol Cs, atomic number 50, and atomic weight 132.91. Cesium has many industrial applications, including the construction of atomic clocks based on its atomic vibrational frequency.	2.05	1	0	alkali metal atom
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.	2.02	1	0	alkali metal atom
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	6.36	19	0	boron group element atom; elemental aluminium; metal atom
strontium Strontium: An element of the alkaline earth family of metals. It has the atomic symbol Sr, atomic number 38, and atomic weight 87.62.	2.07	1	0	alkaline earth metal atom
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)	10.54	4	1	metalloid atom; pnictogen	micronutrient
indium Indium: A metallic element, atomic number 49, atomic weight 114.818, symbol In. It is named from its blue line in the spectrum.. indium atom : A metallic element first identified and named from the brilliant indigo (Latin indicum) blue line in its flame spectrum.	7.75	3	0	boron group element atom
naltrexone Naltrexone: Derivative of noroxymorphone that is the N-cyclopropylmethyl congener of NALOXONE. It is a narcotic antagonist that is effective orally, longer lasting and more potent than naloxone, and has been proposed for the treatment of heroin addiction. The FDA has approved naltrexone for the treatment of alcohol dependence.. naltrexone : An organic heteropentacyclic compound that is naloxone substituted in which the allyl group attached to the nitrogen is replaced by a cyclopropylmethyl group. A mu-opioid receptor antagonist, it is used to treat alcohol dependence.	2.05	1	0	cyclopropanes; morphinane-like compound; organic heteropentacyclic compound	antidote to opioid poisoning; central nervous system depressant; environmental contaminant; mu-opioid receptor antagonist; xenobiotic
gallium Gallium: A rare, metallic element designated by the symbol, Ga, atomic number 31, and atomic weight 69.72.. gallium atom : A metallic element predicted as eka-aluminium by Mendeleev in 1870 and discovered by Paul-Emile Lecoq de Boisbaudran in 1875. Named in honour of France (Latin Gallia) and perhaps also from the Latin gallus cock, a translation of Lecoq.	2.75	3	0	boron group element atom
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.	6.96	29	0	chalcogen; nonmetal atom	macronutrient
lewisite lewisite: RN given refers to cpd without isomeric designation	2.05	1	0
puerarin [no description available]	2.05	1	0	C-glycosyl compound; isoflavonoid
catharanthine [no description available]	2.05	1	0	alkaloid ester; bridged compound; methyl ester; monoterpenoid indole alkaloid; organic heteropentacyclic compound; tertiary amino compound
deoxyribose [no description available]	7.42	2	0	deoxypentose	human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
fumarates Fumarates: Compounds based on fumaric acid.. fumarate(2-) : A C4-dicarboxylate that is the E-isomer of but-2-enedioate(2-)	2.7	3	0	butenedioate; C4-dicarboxylate	human metabolite; metabolite; Saccharomyces cerevisiae metabolite
phycocyanobilin phycocyanobilin: tetrapyrrole prosthetic group of phycocyanin protein. phycocyanobilin : A bilin that consists of 8,12-bis(2-carboxyethyl)-18-ethyl-3-ethylidene-2,7,13,17-tetramethyl-2,3-dihydrobilin bearing two oxo substituents at positions 1 and 19.	2	1	0
beryllium Beryllium: An element with the atomic symbol Be, atomic number 4, and atomic weight 9.01218. Short exposure to this element can lead to a type of poisoning known as BERYLLIOSIS.. beryllium atom : Alkaline earth metal atom with atomic number 4.	2.1	1	0	alkaline earth metal atom; elemental beryllium; metal allergen	adjuvant; carcinogenic agent; epitope
tyrosine [no description available]	2.02	1	0	alpha-amino-acid radical
turanose turanose : A glycosylfructose isolated from Daphnia magna.	2.02	1	0	glycosylfructose	Daphnia magna metabolite
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.	4.91	11	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].	3.78	10	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.	8.47	27	1	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.	4.93	11	0	boron group element atom; metalloid atom; nonmetal atom	micronutrient
lycopodine [no description available]	3.12	1	0	quinolizidine alkaloid
metaproterenol 1-methoxy-3-indolylmethylglucosinolate: isolated from Moricandia arvensis (Cruciferae); structure given in first source. neoglucobrassicin : An indolyl carbohydrate that is glucobrassicin methoxy substituted at position 1 of the indole moiety.	2.08	1	0
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.	12.09	465	0	2-trans-abscisic acid
abienol abienol: isolated from tobacco Nicotiana tabacum; structure in first source	2.07	1	0
mastoparan [no description available]	7.05	1	0	mastoparans; peptidyl amide	antimicrobial agent
germanium Germanium: A rare metal element with a blue-gray appearance and atomic symbol Ge, atomic number 32, and atomic weight 72.63.	2.06	1	0	carbon group element atom; metalloid atom; nonmetal atom
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.	3.35	6	0	chalcogen; nonmetal atom	micronutrient
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.	2.03	1	0
clinoptilolite clinoptilolite: clinoptilolite was SY to zeolite (NM); use zeolites (NM) to search through 1993; RN is for cpd with unknown MF	2.55	2	0
raubasine raubasine: RN given refers to (19alpha)-isomer; structure	2.49	2	0	yohimban alkaloid
antimycin a Antimycin A: An antibiotic substance produced by Streptomyces species. It inhibits mitochondrial respiration and may deplete cellular levels of ATP. Antimycin A1 has been used as a fungicide, insecticide, and miticide. (From Merck Index, 12th ed). antimycin A : A nine-membered bis-lactone having methyl substituents at the 2- and 6-positions, an n-hexyl substituent at the 8-position, an acyloxy substituent at the 7-position and an aroylamido substituent at the 3-position. It is produced by Streptomyces bacteria and has found commercial use as a fish poison.	2.03	1	0	amidobenzoic acid
aminoethoxyvinylglycine aminoethoxyvinylglycine: RN given for (S-(E))-isomer	10.48	62	0
rhizobitoxine rhizobitoxine: toxic substance found in extracts of R. japonicum; believed to be helpful in protecting soybean roots from M. phaseolina infection	3.51	2	0
2-chlorovinylarsonous acid 2-chlorovinylarsonous acid: major metabolite of lewisite; structure in first source	2.05	1	0
bacteriochlorophylls Bacteriochlorophylls: Pyrrole containing pigments found in photosynthetic bacteria.	1.97	1	0
zeatin riboside zeatin riboside: RN given refers to parent cpd. 9-ribosyl-trans-zeatin : A 9-ribosylzeatin having trans-zeatin as the nucleobase.	2.1	1	0	9-ribosylzeatin; nucleoside analogue	cytokinin; plant metabolite
axitinib [no description available]	4.61	1	1	aryl sulfide; benzamides; indazoles; pyridines	antineoplastic agent; tyrosine kinase inhibitor; vascular endothelial growth factor receptor antagonist
sorgoleone sorgoleone: Sorgoleone refers to a group of benzoquinones from Sorghum bicolor having 2-hydroxy and 5-methoxy substitutions and either a 15- or 17-carbon chain with one, two, or three double bonds at position 3; The name sorgoleone was first given to 5-methoxy-3-(8'Z,11'Z)-pentadeca-8'11'14'-trienylbenzene-1,2,4-triol but this is unstable and is easily oxidized to the quinone, sorgoleone-358, which is the major constituent of the root exudate; binds at PLASTOQUINONE site of PSII. sorgoleone : A member of the family of benzoquinones, sorgoleone is 2-hydroxy-5-methoxy-1,4-benzoquinone in which the hydrogen at position 3 is substituted by a (4Z,7Z)-pentadeca-1,4,7-trien-15-yl group.	2.02	1	0	monohydroxy-1,4-benzoquinones
paclobutrazol paclobutrazol: RN given refers to (R,R)-(+-)-isomer. paclobutrazol : A racemate comprising equimolar amounts of (2R,3R)- and (2S,3S)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentan-3-ol. It acts as a plant-growth retardant and fungicide via inhibition of gibberellin biosynthesis.	3.54	8	0
beta-escin [no description available]	3.29	6	0
glucoraphanin glucoraphanin: precursor of sulforaphane. glucoraphanin : A thia-glucosinolic acid that is glucoerucin in which the sulfur atom of the methyl thioether group has been oxidised to the corresponding sulfoxide.	2.08	1	0	sulfoxide; thia-alkylglucosinolic acid
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.	1.96	1	0	imidazolidine-2,4-dione; nitrofuran antibiotic; organonitrogen heterocyclic antibiotic; organooxygen heterocyclic antibiotic	antibacterial drug; antiinfective agent; hepatotoxic agent
shellac shellac: RN given refers to parent cpd	2.31	1	0
staurosporine staurosporinium : Conjugate acid of staurosporine.	3.11	5	0	ammonium ion derivative
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).	5.63	23	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
nicotianamine nicotianamine: an angiotensin I-converting enzyme inhibitor from soy sauce. (S,S,S)-nicotianamine : The (S,S,S)-stereoisomer of nicotianamine.	3.55	2	0	amino acid zwitterion; nicotianamine	chelator; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; plant metabolite
6''-o-malonyldaidzin 6''-O-malonyldaidzin: structure in first source. malonyldaidzin : A glycosyloxyisoflavone that is daidzein substituted by a 6-O-(carboxyacetyl)-beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage.	2.13	1	0	glycosyloxyisoflavone; hydroxyisoflavone; malonate ester; monosaccharide derivative	plant metabolite
sorbitan monooleate [no description available]	4.61	1	1	fatty acid ester
zeolites [no description available]	4.6	24	0
pitolisant pitolisant: functions as both inverse agonist and antagonist of histamine H3 receptors; structure in first source	4.61	1	1	organochlorine compound
aluminum oxide Aluminum Oxide: An oxide of aluminum, occurring in nature as various minerals such as bauxite, corundum, etc. It is used as an adsorbent, desiccating agent, and catalyst, and in the manufacture of dental cements and refractories.	3.83	11	0
actein actein: a cyclolanostane from the Chinese drug Shoma; structure in first source	2.13	1	0	triterpenoid	metabolite
methionine sulfoxide methionine sulfoxide: RN given refers to cpd without isomeric designation. L-methionine (R)-S-oxide : The (R)-oxido diastereomer of L-methionine S-oxide.	2	1	0	amino acid zwitterion; L-methionine S-oxide	Escherichia coli metabolite
phosphoramidite phosphoramidite: structure in first source. phosphoramidite : A compound with the general formula (RO)2PNR2. Phosphoramidites can be regarded as phosphites that have an NR2 instead of an OH group, or as amides of phosphorous acid.	2.25	1	0
vitamin u Vitamin U: A vitamin found in green vegetables. It is used in the treatment of peptic ulcers, colitis, and gastritis and has an effect on secretory, acid-forming, and enzymatic functions of the intestinal tract.. S-methyl-L-methioninate : A sulfonium betaine that is a conjugate base of S-methyl-L-methionine obtained by the deprotonation of the carboxy group.	2.01	1	0	methyl-L-methionine; sulfonium betaine
oxadiazoles Oxadiazoles: Compounds containing five-membered heteroaromatic rings containing two carbons, two nitrogens, and one oxygen atom which exist in various regioisomeric forms.	2.07	1	0
sch 442416 SCH 442416: an adenosine A2A receptor ligand	2.04	1	0	triazolopyrimidines
apicularen a apicularen A: isolated from Chondromyces; structure in first source	7.03	1	0
digalactosyldiacylglycerol digalactosyldiacylglycerol: two Galactoses bound to diacylglycerol; the mono Gal MGDG is also available; constitutes 20% of plant chloroplast lipids; see also 1,2-distearoyldigalactosyldiglyceride	2.13	1	0
esculeoside a esculeoside A: a major component contained in the ripe tomato Lycopersicon esculentum fruits; structure in first source. esculeoside A : A steroid saponin that is spirosolane-3,23,27-triol in which the hydroxy group at position 23 is acetylated and the hydroxy groups at positions 3 and 27 are glycosylated by lycotetraosyl and a beta-D-glucopyranosyl moieties respectively. Isolated from the fruits of Lycopersicon esculentum, it exhibits cytotoxic activity.	7.05	1	0	azaspiro compound; oxaspiro compound; saponin; steroid alkaloid; steroid saponin	antineoplastic agent; metabolite
ribose ribopyranose : The pyranose form of ribose.	2.17	1	0	D-ribose; ribopyranose
acebutolol alpha-D-glucosyl-(1->4)-alpha-D-mannose : An alpha-D-glucosyl-(1->4)-D-mannopyranose in which the anomeric hydroxy group has alpha configuration.	2.02	1	0	alpha-D-glucosyl-(1->4)-D-mannopyranose
mugineic acid mugineic acid: RN refers to (2S-(1(alphaR(R),betaR),2R))-isomer; structure in first source. mugineic acid : An azetidinecarboxylic acid that is the parent of the class of mugineic acids.	3.17	1	0	mugineic acids
karrikinolide karrikinolide: a seed germination stimulant formed during burning of plant material; structure in first source	2.11	1	0
n-coumaroyldopamine N-coumaroyldopamine: structure in first source	2.03	1	0
2,4,3',5'-tetrahydroxystilbene oleocanthal: newly pressed extra-virgin olive oil contains oleocanthal, acting as a natural anti-inflammatory compound that has a potency and profile strikingly similar to that of ibuprofen; structure in first source. oleocanthal : A carboxylic ester that is the 2-(p-hydroxyphenyl)ethyl ester of (3S)-4-formyl-3-(2-oxoethyl)hex-4-enoic acid. Oleocanthal is found in olive oil but it is not clear whether the natural product is a mixture of E/Z isomers or a single isomer as the two isomers readily interconvert in solution; most pharmacological studies will have been performed using a mixture.	2.03	1	0
n-(2-cyanoethyl)valine N-(2-cyanoethyl)valine: structure given in first source	2.1	1	0
myrigalone a myrigalone A: a phytotoxin isolated from the fruit of Myrica gale; structure in first source	2.07	1	0	monoterpenoid
calcimycin Calcimycin: An ionophorous, polyether antibiotic from Streptomyces chartreusensis. It binds and transports CALCIUM and other divalent cations across membranes and uncouples oxidative phosphorylation while inhibiting ATPase of rat liver mitochondria. The substance is used mostly as a biochemical tool to study the role of divalent cations in various biological systems.	1.96	1	0	benzoxazole
phytosterols Phytosterols: A class of organic compounds known as sterols or STEROIDS derived from plants.. phytosterols : Sterols similar to cholesterol which occur in plants and vary only in carbon side chains and/or presence or absence of a double bond.	3.32	6	0
titanocene titanocene: C10-H10-Ti. titanocene : A bis(eta(5)-cyclopentadienyl)metal(II) having Ti(II) as the metal(II) species. The parent of the class of titanonocenes.	7.46	2	0
acid phosphatase Acid Phosphatase: An enzyme that catalyzes the conversion of an orthophosphoric monoester and water to an alcohol and orthophosphate. EC 3.1.3.2.	8.18	5	0
2-aminoindan-2-phosphonic acid 2-aminoindan-2-phosphonic acid: inhibits salicylic acid synthesis	2.08	1	0
3-oxetanone [no description available]	2.11	1	0
methampicillin brassinazole: a triazole-type brassinosteroid biosynthesis inhibitor; structure in first source. brassinazole : A member of the class of triazoles that is butan-2-ol which is substituted at positions 2, 3, and 4 by phenyl, 1H-1,2,4-triazol-1-yl and p-chlorophenyl groups, respectively. An inhibitor of brassinosteroid biosynthesis.	2.51	2	0	monochlorobenzenes; tertiary alcohol; triazoles	brassinosteroid biosynthesis inhibitor
n-(2-chloro-4-pyridyl)-n-phenylurea [no description available]	2.21	1	0
malonylgenistin malonylgenistin: structure in first source. malonylgenistin : A glycosyloxyisoflavone that is genistin in which the hydroxy hydrogen at position 6'' has been replaced by a malonyl group.	2.13	1	0	beta-D-glucoside; glycosyloxyisoflavone; hydroxyisoflavone; malonate ester; monosaccharide derivative	plant metabolite
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	2.37	2	0	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
cytochrome c-t Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.	2.73	3	0
feruloyldopamine feruloyldopamine: a dopamine metabolite isolated from tomatoes after infection by Pseudomonas syringae; structure in first source	2.03	1	0
glucagon Glucagon: A 29-amino acid pancreatic peptide derived from proglucagon which is also the precursor of intestinal GLUCAGON-LIKE PEPTIDES. Glucagon is secreted by PANCREATIC ALPHA CELLS and plays an important role in regulation of BLOOD GLUCOSE concentration, ketone metabolism, and several other biochemical and physiological processes. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1511). glucagon : A 29-amino acid peptide hormone consisting of His, Ser, Gln, Gly, Thr, Phe, Thr, Ser, Asp, Tyr, Ser, Lys, Tyr, Leu, Asp, Ser, Arg, Arg, Ala, Gln, Asp, Phe, Val, Gln, Trp, Leu, Met, Asn and Thr residues joined in sequence.	4.61	1	1	peptide hormone
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.	3.51	7	0
oligonucleotides [no description available]	5	12	0
r18 peptide R18 peptide: a 20-mer peptide, derived from a phage library, that binds 14-3-3 tau protein; amino acid sequence in first source	2.08	1	0
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	7.63	25	1	glycoside
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	2.7	3	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.	12.13	104	0	chlorophyll; methyl ester	cofactor
adenosine kinase Adenosine Kinase: An enzyme that catalyzes the formation of ADP plus AMP from adenosine plus ATP. It can serve as a salvage mechanism for returning adenosine to nucleic acids. EC 2.7.1.20.	2.08	1	0
sodium salicylate [no description available]	7.65	3	0	organic molecular entity
sapogenins Sapogenins: The aglucon moiety of a saponin molecule. It may be triterpenoid or steroid, usually spirostan, in nature.	2.05	1	0
triazacyclononane triazacyclononane: structure in first source	2.05	1	0
chitosan [no description available]	11.76	9	1
volicitin volicitin: an elicitor that triggers emission of volatile from plants	8.81	3	0
mesna Mesna: A sulfhydryl compound used to prevent urothelial toxicity by inactivating metabolites from ANTINEOPLASTIC AGENTS, such as IFOSFAMIDE or CYCLOPHOSPHAMIDE.	2.03	1	0	organosulfonic acid
methyl orange methyl orange: indictor of pH with strong acids & bases; also used as reagent to form ion pairs with, and thereby isolate, certain compounds from biological material; minor descriptor (75-86); on-line & INDEX MEDICUS search AZO COMPOUNDS (75-86); file maintained to Azo cpds	2.25	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	2.04	1	0
methyl jasmonate [no description available]	8.21	135	0
s-adenosylmethionine (R)-S-adenosyl-L-methionine : An S-adenosyl-L-methionine that has R-configuration.. S-adenosyl-L-methionine zwitterion : A zwitterionic tautomer of S-adenosyl-L-methionine arising from shift of the proton from the carboxy group to the amino group.. (R)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has R-configuration; major species at pH 7.3.. (S)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has S-configuration; major species at pH 7.3.. S-adenosyl-L-methionine : A sulfonium compound that is the S-adenosyl derivative of L-methionine. It is an intermediate in the metabolic pathway of methionine.	6.59	20	0	organic cation; sulfonium compound	coenzyme; cofactor; human metabolite; micronutrient; Mycoplasma genitalium metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
ethyl cellulose [no description available]	2.03	1	0	glycoside
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [no description available]	2.07	1	0	BODIPY compound
systemin systemin: amino acid sequence given in first source; a mobile 18 amino acid polypeptide, induces proteinase inhibitor synthesis; from Lycopersicon esculentum (tomato)	5.05	5	0
mannans [no description available]	2.05	1	0
nitrogenase Nitrogenase: An enzyme system that catalyzes the fixing of nitrogen in soil bacteria and blue-green algae (CYANOBACTERIA). EC 1.18.6.1.	4.49	23	0
phosphinothricin phosphinothricin: RN given refers to parent cpd with unspecified isomeric designation; structure. phosphinothricin(1-) : Conjugate base of phosphinothricin arising from deprotonation of the phosphinate function.	2.02	1	0	organic anion
phytochromobilin phytochromobilin: structure given in first source; this bilin is a pigment derived from phycoerythrobilin-containing proteins. phytochromobilin : A member of the class of bilins which functions as the chromophore of light-sensing phytochromes in plants.. (3Z)-phytochromobilin(2-) : Dicarboxylate anion of (3Z)-phytochromobilin.	2.76	3	0
peptones Peptones: Derived proteins or mixtures of cleavage products produced by the partial hydrolysis of a native protein either by an acid or by an enzyme. Peptones are readily soluble in water, and are not precipitable by heat, by alkalis, or by saturation with ammonium sulfate. (Dorland, 28th ed)	2.04	1	0
glycolipids [no description available]	4.99	2	1
piperidines Piperidines: A family of hexahydropyridines.	5.43	4	1
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.	4.61	1	1
5-(4-amino-1-propan-2-yl-3-pyrazolo[3,4-d]pyrimidinyl)-1,3-benzoxazol-2-amine sapanisertib: an mTOR inhibitor	4.61	1	1	benzoxazole
fructose-1,6-diphosphate fructose-1,6-diphosphate: RN refers to (D)-isomer	1.97	1	0
heme Heme: The color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins.. ferroheme : Any iron(II)--porphyrin coordination complex.. ferroheme b : Heme b in which the iron has oxidation state +2.. heme : A heme is any tetrapyrrolic chelate of iron.	10.92	4	1
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.	7.09	43	0	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
salicylates Salicylates: The salts or esters of salicylic acids, or salicylate esters of an organic acid. Some of these have analgesic, antipyretic, and anti-inflammatory activities by inhibiting prostaglandin synthesis.. hydroxybenzoate : Any benzoate derivative carrying a single carboxylate group and at least one hydroxy substituent.. salicylates : Any salt or ester arising from reaction of the carboxy group of salicylic acid, or any ester resulting from the condensation of the phenolic hydroxy group of salicylic acid with an organic acid.. salicylate : A monohydroxybenzoate that is the conjugate base of salicylic acid.	6.24	26	0	monohydroxybenzoate	plant metabolite
mobiflex tenoxicam : A thienothiazine-derived monocarboxylic acid amide obtained by formal condensation of the carboxy group of 4-hydroxy-2-methylthieno[2,3-e][1,2]thiazine-3-carboxylic acid 1,1-dioxide with the amino group of 2-aminopyridine. Used for the treatment of pain and inflammation in osteoarthritis and rheumatoid arthritis. It is also indicated for short term treatment of acute musculoskeletal disorders including strains, sprains and other soft-tissue injuries.	2.04	1	0	heteroaryl hydroxy compound; monocarboxylic acid amide; pyridines; thienothiazine	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
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.	4.02	4	0	benzenes; hydroxycoumarin; methyl ketone
dihydroxyfumarate dihydroxyfumarate: RN given refers to ((E)-isomer); structure. dihydroxyfumaric acid : A 2-hydroxydicarboxylic acid consisting of fumaric acid having two hydroxy groups at the 2- and 3-positions.	1.97	1	0	2-hydroxydicarboxylic acid; C4-dicarboxylic acid
grn163 GRN163: inhibitor of telomerase RNA in human multiple myeloma cells.	2.03	1	0
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.	3.24	5	0
lead radioisotopes Lead Radioisotopes: Unstable isotopes of lead that decay or disintegrate emitting radiation. Pb atoms with atomic weights 194-203, 205, and 209-214 are radioactive lead isotopes.	1.98	1	0
transforming growth factor beta Transforming Growth Factor beta: A factor synthesized in a wide variety of tissues. It acts synergistically with TGF-alpha in inducing phenotypic transformation and can also act as a negative autocrine growth factor. TGF-beta has a potential role in embryonal development, cellular differentiation, hormone secretion, and immune function. TGF-beta is found mostly as homodimer forms of separate gene products TGF-beta1, TGF-beta2 or TGF-beta3. Heterodimers composed of TGF-beta1 and 2 (TGF-beta1.2) or of TGF-beta2 and 3 (TGF-beta2.3) have been isolated. The TGF-beta proteins are synthesized as precursor proteins.	1.99	1	0
okadaic acid Okadaic Acid: A specific inhibitor of phosphoserine/threonine protein phosphatase 1 and 2a. It is also a potent tumor promoter. It is produced by DINOFLAGELLATES and causes diarrhetic SHELLFISH POISONING.. okadaic acid : A polycyclic ether that is produced by several species of dinoflagellates, and is known to accumulate in both marine sponges and shellfish. A polyketide, polyether derivative of a C38 fatty acid, it is one of the primary causes of diarrhetic shellfish poisoning (DSP). It is a potent inhibitor of specific protein phosphatases and is known to have a variety of negative effects on cells.	2.07	1	0	ketal
pyrethrins [no description available]	2.01	1	0
agar Agar: A complex sulfated polymer of galactose units, extracted from Gelidium cartilagineum, Gracilaria confervoides, and related red algae. It is used as a gel in the preparation of solid culture media for microorganisms, as a bulk laxative, in making emulsions, and as a supporting medium for immunodiffusion and immunoelectrophoresis.. agar : A complex mixture of polysaccharides extracted from species of red algae. Its two main components are agarose and agaropectin. Agarose is the component responsible for the high-strength gelling properties of agar, while agaropectin provides the viscous properties.	2.47	2	0
crotogoudin crotogoudin: has antineoplastic activity; structure in first source	2.15	1	0
ganoderic acid ganoderic acid: from the fruiting body of Ganoderma; structure in first source	7.15	1	0
lysophosphatidylethanolamine lysophosphatidylethanolamine : A glycerophosphoethanolamine resulting from partial hydrolysis of a phosphatidylethanolamine, which removes one of the fatty acid groups. The structure is depicted in the image where R(1) = acyl, R(2) = H or where R(1) = H, R(2) = acyl.	2.52	2	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.	1.94	1	0
chromosaponin i chromosaponin I: structure given in first source; isolated from Pisum sativum	7.7	3	0
asbestos, crocidolite Asbestos, Crocidolite: A lavender, acid-resistant asbestos.	1.96	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.	2.11	1	0	phthalocyanines; tetrapyrrole fundamental parent
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	1.93	1	0
mesembrine [no description available]	3.12	1	0
gibberellins [no description available]	11.1	193	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.	2.66	3	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.	7.05	1	0
lactoferrin Lactoferrin: An iron-binding protein that was originally characterized as a milk protein. It is widely distributed in secretory fluids and is found in the neutrophilic granules of LEUKOCYTES. The N-terminal part of lactoferrin possesses a serine protease which functions to inactivate the TYPE III SECRETION SYSTEM used by bacteria to export virulence proteins for host cell invasion.	7.11	1	0
catalpol catalpol: component of dihuang; RN given refers to (1aS-(1aalpha,1bbeta,2beta,5abeta,6beta,6aalpha))-isomer; RN for cpd without isomeric designation not avail 12/92	4.61	1	1
tomatine Tomatine: An alkaloid that occurs in the extract of leaves of wild tomato plants. It has been found to inhibit the growth of various fungi and bacteria. It is used as a precipitating agent for steroids. (From The Merck Index, 11th ed). tomatine : A steroid alkaloid that is tomatidine in which the hydroxy group at position 3 is linked to lycotetraose, a tetrasaccharide composed of two units of D-glucose, one unit of D-xylose, and one unit of D-galactose.	2.46	2	0
orabase Orabase: used in therapy of oral mucosal ulcers	2.46	2	0
apyrase Apyrase: A calcium-activated enzyme that catalyzes the hydrolysis of ATP to yield AMP and orthophosphate. It can also act on ADP and other nucleoside triphosphates and diphosphates. EC 3.6.1.5.	2.44	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.	2.38	2	0
perlite Perlite: siliceous volcanic rock composed of silicon dioxide & aluminum oxide	2.08	1	0
cyclic gmp Cyclic GMP: Guanosine cyclic 3',5'-(hydrogen phosphate). A guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger. Its levels increase in response to a variety of hormones, including acetylcholine, insulin, and oxytocin and it has been found to activate specific protein kinases. (From Merck Index, 11th ed). 3',5'-cyclic GMP : A 3',5'-cyclic purine nucleotide in which the purine nucleobase is specified as guanidine.	2.49	2	0	3',5'-cyclic purine nucleotide; guanyl ribonucleotide	Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
guanosine triphosphate Guanosine Triphosphate: Guanosine 5'-(tetrahydrogen triphosphate). A guanine nucleotide containing three phosphate groups esterified to the sugar moiety.	2.41	2	0	guanosine 5'-phosphate; purine ribonucleoside 5'-triphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor
guanine [no description available]	7.93	4	0	2-aminopurines; oxopurine; purine nucleobase	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanosine ribonucleoside : Any nucleoside where the sugar component is D-ribose.	2.51	2	0	guanosines; purines D-ribonucleoside	fundamental metabolite
folic acid folcysteine: used to promote fertility in chickens. vitamin B9 : Any B-vitamin that exhibits biological activity against vitamin B9 deficiency. Vitamin B9 refers to the many forms of folic acid and its derivatives, including tetrahydrofolic acid (the active form), methyltetrahydrofolate (the primary form found in blood), methenyltetrahydrofolate, folinic acid amongst others. They are present in abundance in green leafy vegetables, citrus fruits, and animal products. Lack of vitamin B9 leads to anemia, a condition in which the body cannot produce sufficient number of red blood cells. Symptoms of vitamin B9 deficiency include fatigue, muscle weakness, and pale skin.	2.82	3	0	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
3-methyladenine N3-methyladenine: structure in first source	2.05	1	0
pheophytin a pheophytin a: structure given in first source; RN given refers to (3S-(3alpha(2E,7S,11S),4beta,21beta))-isomer	3.46	7	0
olanzapine Olanzapine: A benzodiazepine derivative that binds SEROTONIN RECEPTORS; MUSCARINIC RECEPTORS; HISTAMINE H1 RECEPTORS; ADRENERGIC ALPHA-1 RECEPTORS; and DOPAMINE RECEPTORS. It is an antipsychotic agent used in the treatment of SCHIZOPHRENIA; BIPOLAR DISORDER; and MAJOR DEPRESSIVE DISORDER; it may also reduce nausea and vomiting in patients undergoing chemotherapy.. olanzapine : A benzodiazepine that is 10H-thieno[2,3-b][1,5]benzodiazepine substituted by a methyl group at position 2 and a 4-methylpiperazin-1-yl group at position 4.	2.04	1	0	benzodiazepine; N-arylpiperazine; N-methylpiperazine	antiemetic; dopaminergic antagonist; histamine antagonist; muscarinic antagonist; second generation antipsychotic; serotonergic antagonist; serotonin uptake inhibitor
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.	3.48	8	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
guanylyl imidodiphosphate Guanylyl Imidodiphosphate: A non-hydrolyzable analog of GTP, in which the oxygen atom bridging the beta to the gamma phosphate is replaced by a nitrogen atom. It binds tightly to G-protein in the presence of Mg2+. The nucleotide is a potent stimulator of ADENYLYL CYCLASES.. guanosine 5'-[beta,gamma-imido]triphosphate : A nucleoside triphosphate analogue that is GTP in which the oxygen atom bridging the beta- to the gamma- phosphate is replaced by a nitrogen atom A non-hydrolyzable analog of GTP, it binds tightly to G-protein in the presence of Mg(2+).	2.03	1	0	nucleoside triphosphate analogue
8-bromocyclic gmp 8-bromo-3',5'-cyclic GMP : A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic GMP bearing an additional bromo substituent at position 8 on the guanine ring. A membrane permeable cGMP analogue that activates protein kinase G (PKG). It is 4.3-fold more potent than cGMP in activating PKG1alpha and promotes relaxation of tracheal and vascular smooth muscle tissue in vitro.	2.1	1	0	3',5'-cyclic purine nucleotide; organobromine compound	muscle relaxant; protein kinase G agonist
trypan blue Trypan Blue: A diazo-naphthalene sulfonate that is widely used as a stain.. trypan blue : An organosulfonate salt that is the tetrasodium salt of 3,3'-[(3,3'-dimethylbiphenyl-4,4'-diyl)didiazene-2,1-diyl]bis(5-amino-4-hydroxynaphthalene-2,7-disulfonic acid).	2.07	1	0
5-methyltetrahydrofolate 5-methyltetrahydrofolate : A group of heterocyclic compounds based on the 5-methyl-5,6,7,8-tetrahydropteroic acid skeleton conjugated with one or more L-glutamic acid or L-glutamate units.	2.03	1	0
n(7)-hydroxyethylguanine [no description available]	2.42	2	0
p-hydroxybenzylideneimidazolinone p-hydroxybenzylideneimidazolinone: structure in first source	2.1	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.	4.61	1	1
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.	9.61	8	0
dinitrobenzenes Dinitrobenzenes: Benzene derivatives which are substituted with two nitro groups in the ortho, meta or para positions.	2.74	3	0
pyrimidinones Pyrimidinones: Heterocyclic compounds known as 2-pyrimidones (or 2-hydroxypyrimidines) and 4-pyrimidones (or 4-hydroxypyrimidines) with the general formula C4H4N2O.	2.44	2	0
filipin Filipin: A complex of polyene antibiotics obtained from Streptomyces filipinensis. Filipin III alters membrane function by interfering with membrane sterols, inhibits mitochondrial respiration, and is proposed as an antifungal agent. Filipins I, II, and IV are less important.	2.1	1	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.	2.77	3	0

ethylene

Description

Cross-References

Synonyms (76)

Research Excerpts

Overview

Effects

Actions

Treatment

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Roles (2)

Drug Classes (2)

Pathways (22)

Bioassays (6)

Research

Studies (5,733)

Market Indicators

Research Demand Index: 117.44

Study Types

Clinical Trials (8)

Trial Overview

Trial Outcomes

Maximum Tolerated Dose of Samarium-153

ethylene

Description

Cross-References

Synonyms (76)

Research Excerpts

Overview

Effects

Actions

Treatment

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Roles (2)

Drug Classes (2)

Pathways (22)

Bioassays (6)

Research

Studies (5,733)

Market Indicators

Research Demand Index: 117.44

Study Types

Clinical Trials (8)

Trial Overview

Trial Outcomes

Maximum Tolerated Dose of Samarium-153

Related Drugs (1,253)

Related Conditions (531)