lignin profile

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) [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

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. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

ID Source	ID
PubMed CID	175586
MeSH ID	M0012517

Synonym
lignin
disodium 4-(acetylamino)-5-hydroxy-6-(phenylazo)naphthalene-1,7-disulphonate
einecs 302-591-3
94113-57-2

Excerpt	Reference	Relevance
"Lignin is a naturally occurring polymer that is considered to be an important part of soil carbon cycling."	( Cd and Pb immobilisation with iron oxide/lignin composite and the bacterial community response in soil. Chen, Z; Huang, F; Liu, Q; Luo, J; Tang, J; Wang, P; Xiao, R, 2022)	1.71
"Lignin is an aromatic polymer that constitutes up to 30 wt% of woody biomass and is considered the largest source of renewable aromatics. "	( Oxidative cleavage of C-C bonds in lignin. Johnsson, M; Marquez-Medina, MD; Rukkijakan, T; Samec, JSM; Subbotina, E; Yu, X, 2021)	2.34
"Lignin is a waste by-product of bio-refineries and paper-pulp industries. "	( Hydrothermal oxidative valorisation of lignin into functional chemicals: A review. Bhaskar, T; Biswas, B; Kaur, R; Krishna, BB; Kumar, A, 2021)	2.33
"Lignin is a potential source of valuable chemicals, but its chemical depolymerization results in a heterogeneous mixture of aromatics and other products. "	( Aromatic Dimer Dehydrogenases from Donohue, TJ; Kontur, WS; Linz, AM; Ma, Y; Myers, KS; Noguera, DR; Perez, JM, 2021)	2.06
"Lignin is a robust and underutilized aromatic heteropolymer on earth. "	( Construction of a p-coumaric and ferulic acid auto-regulatory system in Pseudomonas putida KT2440 for protocatechuate production from lignin-derived aromatics. Li, J; Shang, Y; Wei, W; Ye, BC; Yue, C; Zhang, P, 2022)	2.37
"Lignin is an abundant and sustainable source of aromatic compounds that can be converted to value-added products. "	( Microbial assimilation of lignin-derived aromatic compounds and conversion to value-added products. Allemann, MN; Azubuike, CC; Michener, JK, 2022)	2.46
"Lignin is an abundant plant-based biopolymer that has found applications in a variety of industries from construction to bioethanol production. "	( Lignin degradation by microorganisms: A review. Atiwesh, G; Banoub, J; Le, TT; Parrish, CC, 2022)	3.61
"Lignin is an important structural component of terrestrial plants and is readily generated during biomass fractionation in lignocellulose processing facilities. "	( Guiding stars to the field of dreams: Metabolically engineered pathways and microbial platforms for a sustainable lignin-based industry. Kohlstedt, M; Weiland, F; Wittmann, C, 2022)	2.37
"Lignin is a rich renewable source of aromatics present in lignocellulosic biomass (LCB). "	( Microwave-assisted extraction of lignin from coconut coir using deep eutectic solvents and its valorization to aromatics. Mankar, AR; Pandey, A; Pant, KK, 2022)	2.45
"Lignin is a complex phenylpropanoid polymer deposited in the secondary cell walls of vascular plants. "	( Deficiency in flavonoid biosynthesis genes CHS, CHI, and CHIL alters rice flavonoid and lignin profiles. Chen, MX; Lam, PY; Liu, H; Lo, C; Lui, ACW; Takeda-Kimura, Y; Tobimatsu, Y; Umezawa, T; Wang, L; Zhang, J; Zhu, FY, 2022)	2.39
"Lignin is a phenolic polymer deposited in the plant cell wall, and is mainly polymerized from three canonical monomers (monolignols), i.e. "	( Rerouting of the lignin biosynthetic pathway by inhibition of cytosolic shikimate recycling in transgenic hybrid aspen. Boerjan, W; Goeminne, G; Hishiyama, S; Hu, S; Kajita, S; Kamimura, N; Kim, H; Liu, S; Masai, E; Mitsuda, N; Nagano, S; Ralph, J; Sakamoto, S; Takata, N; Uesugi, M; Vanholme, R; Yamamoto, M, 2022)	2.5
"Lignin is a major by-product of pulp and paper industries, and is resistant to depolymerization due to its heterogeneous structure. "	( Degradation of lignin by Bacillus altitudinis SL7 isolated from pulp and paper mill effluent. Ahmed, S; Badshah, M; Belduz, AO; Çanakçi, S; Farman, M; Hasan, F; Khan, S; Khan, SI; Shah, AA; Zarin, A, 2022)	2.52
"Lignin is a natural renewable biomass resource with great potential for applications, while its development into high value-added molecules or materials is rare. "	( Lignin-Based Nonviral Gene Carriers Functionalized by Poly[2-(Dimethylamino)ethyl Methacrylate]: Effect of Grafting Degree and Cationic Chain Length on Transfection Efficiency. Li, J; Liu, X; Song, X; Yin, H; Zhang, Z, 2022)	3.61
"Lignin is a highly complex phenolic polymer which is essential for plants, but also makes it difficult for industrial processing. "	( Crystal structure of the plant feruloyl-coenzyme A monolignol transferase provides insights into the formation of monolignol ferulate conjugates. Dai, S; Feng, Y; Li, D; Liu, J; Liu, X; Zhang, J; Zhang, Y; Zhao, Q; Zhou, Y; Zhu, Y, 2022)	2.16
"Lignin is a promising renewable biopolymer being investigated worldwide as an environmentally benign substitute of fossil-based aromatic compounds, e.g. "	( Benchtop versus high field NMR: Comparable performance found for the molecular weight determination of lignin. Burger, R; Diehl, BWK; Do, XT; Lindner, S; Monakhova, YB; Rehahn, M; Rumpf, J; Schulze, M, 2022)	2.38
"Lignin is a heterogeneous aromatic polymer and major component of plant cell walls. "	( Isolation and characterization of microorganisms capable of cleaving the ether bond of 2-phenoxyacetophenone. Furuya, T; Habe, H; Nakagawa, H; Oya, S; Tonegawa, S, 2022)	2.16
"Lignin is a technological bottleneck to convert polysaccharides into fermentable sugars, and different strategies of genetic-based metabolic engineering have been applied to improve biomass saccharification. "	( Inhibiting tricin biosynthesis improves maize lignocellulose saccharification. Bossoni, GEB; Constantin, RP; Dos Santos, WD; Ferrarese-Filho, O; Marchiosi, R; Mendes, GGM; Mota, TR; Oliveira, DM, 2022)	2.16
"Lignin separation is an important procedure that benefits multiple industries and in particular biomass transformation efforts. "	( Efficient separation of bagasse lignin by freeze-thaw-assisted p-toluenesulfonic acid pretreatment. Huang, C; Li, J; Li, M; Li, X; Liang, C; Liu, B; Peng, M; Qin, C; Yao, S; Zeng, H, 2022)	2.45
"Lignin is an abundant natural polymer obtained from lignocellulosic biomass and rich in aromatic substructures. "	( Technology Overview of Fast Pyrolysis of Lignin: Current State and Potential for Scale-Up. Puente-Urbina, A; Singh-Morgan, A; van Bokhoven, JA, 2022)	2.43
"Lignin is a largely untapped source for the bioproduction of value-added chemicals. "	( Engineering Pseudomonas putida for improved utilization of syringyl aromatics. Feist, AM; Mueller, J; Niu, W; Willett, H, 2022)	2.16
"Lignin is a fascinating aromatic biopolymer with high valorization potentiality. "	( Lignin as a Natural Carrier for the Efficient Delivery of Bioactive Compounds: From Waste to Health. Behbahani, PJ; Canova, E; Cravotto, G; Gaudino, EC; Tabasso, S; Verdini, F, 2022)	3.61
"Lignin is a biopolymer with high carbon content, making lignin-based carbon fiber an important research direction. "	( Effect of pre-oxidation temperature and heating rate on the microstructure of lignin carbon fibers. Hu, Z; Innocent, MT; Jia, G; Wang, Q; Wang, S; Wang, X; Xiang, H; Zhou, Z; Zhu, M, 2022)	2.39
"Lignin is a promising alternative to petrochemical precursors for conversion to industrial-needed products. "	( Physicochemical characteristics of organosolv lignins from different lignocellulosic agricultural wastes. Champreda, V; Hararak, B; Laosiripojana, N; Pongchaiphol, S; Raita, M; Suriyachai, N, 2022)	2.42
"Lignin is a complex phenolic compound that can enhance the stiffness, hydrophobicity, and antioxidant capacity of the cell wall; it thus provides a critical barrier against pathogen and insect invaders. "	( Lignin biosynthesis regulated by CsCSE1 is required for Cucumis sativus defence to Podosphaera xanthii. Cui, N; Fan, H; Ma, L; Ma, Z; Meng, X; Tao, R; Yu, Y, 2022)	3.61
"Lignin is a renewable raw material with excellent adsorption, biodegradability, and non-toxicity. "	( Preparation, characterization and formation mechanism of size-controlled lignin nanoparticles. Wang, X; Xu, J; Yang, Y; Zhou, J, 2022)	2.4
"Lignin is an abundant renewable carbon source. "	( Simultaneous Generation of Methyl Esters and CO in Lignin Transformation. Dyson, PJ; Han, B; Liu, M, 2022)	2.42
"Lignin is a natural polymer containing diverse functional groups and displaying an affinity for metals. "	( Kraft lignin and its derivates - A study on the adsorption of mono and multielement metals, potential use for noble metal recycling and an alternative material for solid base catalyst. Akiba, N; Gaubeur, I; Omori, AT, 2022)	2.64
"Lignin is an important root chemical component that is widely used in biogeochemical models to predict root decomposition. "	( Characterizing natural variability of lignin abundance and composition in fine roots across temperate trees: a comparison of analytical methods. Blackwood, CB; Suseela, V; Tharayil, N; Valverde-Barrantes, OJ; Xia, M, 2022)	2.44
"Lignin is a major phenolic polymer from the plant biomass. "	( Application of lignin and lignin-based composites in different tissue engineering fields. Chen, ZS; Huang, C; Liu, Y; Pei, W; Teo, MJ; Wang, X; Wu, Q, 2022)	2.52
"Lignin is a natural and renewable aromatic polymer, but only about 2% of lignin is utilized with high added value. "	( An integral method for determining the molecular composition of lignin and its application. Ma, Q; Zhang, X, 2022)	2.4
"Lignin is a renewable biomacromolecule that can be used as precursors for carbon materials. "	( Construction of self-supporting ultra-micropores lignin-based carbon nanofibers with high areal desalination capacity. Hu, P; Li, M; Liang, C; Qu, W; Wang, J; Yin, L, 2023)	2.61
"Lignin is a major component of plant cell walls and a conserved basic defense mechanism in higher plants deposited in response to aphid infection. "	( Molecular module of CmMYB15-like-Cm4CL2 regulating lignin biosynthesis of chrysanthemum (Chrysanthemum morifolium) in response to aphid (Macrosiphoniella sanborni) feeding. Chen, F; Chen, S; Jiang, J; Li, F; Tian, C; Wang, L; Wang, X; Zhang, Y; Zhou, L, 2023)	2.6
"Lignin is an abundantly available natural polymer that can be selectively modified using a rapidly expanding toolkit of biocatalytic and chemical reactions to yield 'intelligent' theranostic-nanoprobes."	( Green synthesis of lignin-based nanoparticles as a bio-carrier for targeted delivery in cancer therapy. Jain, M; Pathania, K; Pawar, SV; Sah, SP; Salunke, DB; Yadav, AK; Yadav, VG, 2023)	1.96
"Lignin is an abundant and available biopolymer and one of the compounds present in the lignocellulosic waste."	( Nanogreen is the new future: the conversion of lignin and lignocellulosic wastes into nanomaterials. Dos Santos, DF; Gimenes, ML; Moreira, PVV; Moreira, WM; Vieira, MGA, 2023)	1.89
"Lignin is a major component of plant cell walls and is essential for plant growth and development. "	( PagERF81 regulates lignin biosynthesis and xylem cell differentiation in poplar. Chai, GH; Guo, W; Hu, MX; Liu, YL; Lu, MZ; Wang, D; Wang, Q; Zhao, ST; Zhao, XW; Zhou, GK, 2023)	2.68
"Lignin degradation is an effective means of achieving the high-value application of lignin, but degradation usually requires the use of high temperatures and harsh reaction-conditions. "	( Lignin Degradation via Chlorine Dioxide at Room Temperature: Chemical Groups and Structural Characterization. Bo, C; Feng, G; Hu, L; Hu, Y; Jia, P; Song, F; Weng, S; Zhang, G; Zhou, Y, 2023)	3.8
"Lignin is an aromatic polymer that constitutes approximately one-third of the total lignocellulosic biomass and is isolated in huge quantities as a waste material of biofuel and paper production."	( Opportunities and Challenges for Lignin Valorization in Food Packaging, Antimicrobial, and Agricultural Applications. Boarino, A; Klok, HA, 2023)	1.91
"Lignin is a potential renewable feedstock to produce value-added compounds, but the overwhelming bulk of it is either burned for energy or discarded as waste. "	( Exploring the Oxidative Effects of the Microbial Electro-Fenton Process on the Depolymerization of Lignin Extracted from Rice Straw in a Bio-Electrochemical System Coupled with Wastewater Treatment. Chang, C; Gupta, P, 2023)	2.57
"Lignin is a significant renewable carbon source that needs to be exploited to manufacture bio-ethanol and chemical feedstocks. "	( Bioprospecting of novel ligninolytic bacteria for effective bioremediation of agricultural by-product and synthetic pollutant dyes. Bhojiya, AA; Jain, D; Mohanty, SR; Navariya, JK; Singh, A; Upadhyay, SK, 2023)	2.66
"Lignin is an essential metabolite for plant growth but negatively affects the quality of forage barley. "	( Transcriptome analysis identifies differentially expressed genes involved in lignin biosynthesis in barley. Chen, X; Ji, C; Sun, H; Wang, R; Zhao, B; Zhu, B, 2023)	2.58
"Lignin is a crucial component in the wound tissue of tubers. "	( Meyerozyma guilliermondii promoted the deposition of GSH type lignin by activating the biosynthesis and polymerization of monolignols at the wounds of potato tubers. Bi, Y; Long, H; Oyom, W; Prusky, D; Pu, L; Yang, R; Zhang, X; Zhao, J; Zheng, X, 2023)	2.59
"Lignin is a nontoxic and biocompatible biopolymer with many promising characteristics, including a high tensile strength and antioxidant properties. "	( Nano-Strategies for Lignin Biomaterials toward Cancer Therapy. Kai, D; Kai, J; Merzaban, J; Sathasivam, T; Soo, DXY; Sugiarto, S; Yu, Y; Zhu, Q, 2023)	2.68
"Lignin is an abundant and complex plant polymer that may limit litter decomposition, yet lignin is sometimes a minor constituent of soil organic carbon (SOC). "	( Contrasting geochemical and fungal controls on decomposition of lignin and soil carbon at continental scale. Hall, SJ; Hammel, KE; Howe, A; Huang, W; Lu, C; Raman, E; Timokhin, VI; Weintraub-Leff, SR; Yang, J; Yi, B; Yu, W, 2023)	2.59
"Lignin recalcitrance is a key issue in producing value-added products from lignocellulose biomass. "	( Isolation and Characterization of Potential Lignin Peroxidase-Producing Bacteria from Compost Samples at Richards Bay (South Africa). Aruleba, RT; Dube, SL; Jobe, ZZ; Mkhwanazi, LB; Mosa, RA; Ngcobo, BP; Opoku, AR; Osunsanmi, FO, 2023)	2.61
"Lignin is a biopolymer present in the biomass of plants, where it is intertwined and cross-linked with other polymers and macromolecules in the cell walls, generating a lignocellulosic material with potential applications."	( Lignocellulosic-Based Nanoparticles with Photoluminescent Properties for Bioimaging. Alexis, F; Anker, JN; Arcentales, M; Attia, MF; Debut, A; Deng, L; Hu, B; López, F; Martín-Sampedro, R; Romero, MP; Santos-Oliveira, R; Whitehead, DC; Zheng, Y, 2023)	1.63
"Lignin is a type of polyphenol, therefore, sulfonated polyphenol, such as tannic acid, is likely to have similar effects."	( Achieving high enzymatic hydrolysis sugar yield of sodium hydroxide-pretreated wheat straw with a low cellulase dosage by adding sulfomethylated tannic acid. Hu, S; Huang, C; Jiang, B; Jin, Y; Wei, W; Wu, W; Zhang, T, 2023)	1.63
"Lignin is a critical biopolymer for creating a large number of highly valuable biobased compounds. "	( Improved biotransformation of lignin-valorized vanillin into vanillylamine in a sustainable bioreaction medium. Fan, B; Gao, R; He, YC; Li, Q; Li, Y; Ma, C, 2023)	2.64
"Lignin is an important cell wall component that provides plants with mechanical support and improved tolerance to pathogen attacks. "	( Modification of lignin composition by ectopic expressing wheat TaF5H1 led to decreased salt tolerance in transgenic Arabidopsis plants. Bi, C; Cao, X; Guo, G; Jia, S; Li, X; Liu, W; Liu, X; Sun, C, 2023)	2.7
"Lignin is a complex biopolymer comprising phenolic monomers with different degrees of methoxylation and may potentially enhance the degradation of soil pollutants such as polycyclic aromatic hydrocarbons (PAHs) through co-metabolism. "	( Impact of lignin constituents on the bacterial community and polycyclic aromatic hydrocarbon co-metabolism in an agricultural soil. Christie, P; Gu, D; Lin, X; Rao, L; Wu, Y; Xiang, X; Zeng, J, 2023)	2.76
"Lignin is a non-digestible, major component of the seed coat with negative effect on sensory quality, bioavailability and usage of oilseed rape's protein."	( Homoeologous non-reciprocal translocation explains a major QTL for seed lignin content in oilseed rape (Brassica napus L.). Holtgräwe, D; Holzenkamp, K; Möllers, C; Schilbert, HM; Viehöver, P, 2023)	1.86
"Lignin is a natural polymer with abundant functional groups with great application prospects in lignin-based polyurethane elastomers with self-healing abilities. "	( Construction and mechanism study of lignin-based polyurethane with high strength and high self-healing properties. Du, J; Huang, Z; Lin, W; Lin, X; Liu, X; Wang, H; Wu, J; Yi, G; Yin, X, 2023)	2.63
"Lignin is a polymer with a complex structure. "	( Effect of Substituents on Molecular Reactivity during Lignin Oxidation by Chlorine Dioxide: A Density Functional Theory Study. Liang, C; Liu, B; Liu, L; Liu, Y; Mo, X; Qin, C; Qin, X; Yang, R; Yao, S, 2023)	2.6
"Lignin is a major terrestrial source of chromophoric dissolved organic matter (CDOM), and studying the phototransformation of lignin monomers and their related compounds can enhance our understanding of CDOM intramolecular interactions. "	( Phototransformation of Lignin-related Compounds in Chromophoric Dissolved Organic Matter Solutions. Liu, J; Zhang, X; Zhou, C; Zhou, R, 2023)	2.66
"Lignin is an aromatic polymer that makes up one-third of total lingo-cellulosic biomass and is separated into large amounts for biofuel and paper manufacture."	( A Comprehensive Mini-Review on Lignin-Based Nanomaterials for Food Applications: Systemic Advancement and Future Trends. Barathikannan, K; Chelliah, R; Liu, S; Oh, DH; Sultan, G; Vijayalakshmi, S; Wei, S, 2023)	1.92
"Lignin is a group of cell wall localised heterophenolic polymers varying in the chemistry of the aromatic and aliphatic parts of its units. "	( Bulk and In Situ Quantification of Coniferaldehyde Residues in Lignin. Bascik, Z; Blaschek, L; Champagne, A; Dimotakis, C; Kajita, S; Pesquet, E; Subbotina, E; Takahashi, J; Yamamoto, M, 2024)	3.12
"Lignin is a complex polymer that provides structure and toughness to the cell walls of numerous fruit plants."	( Contribution of the Huang, M; Khan, MKU; Liu, M; Ma, Z; Peng, J; Wang, X; Yang, C; Zhang, X, 2023)	1.63
"Lignin is a phenylpropanoid polymer produced in the secondary cell walls of vascular plants. "	( OsCAldOMT1 is a bifunctional O-methyltransferase involved in the biosynthesis of tricin-lignins in rice cell walls. Lam, PY; Lan, W; Lo, C; Matsumoto, N; Ralph, J; Sakamoto, M; Suzuki, S; Takeda, Y; Tobimatsu, Y; Umezawa, T; Yamamura, M, 2019)	2.18
"Lignin is an abundant aromatic polymer found in plant secondary cell walls. "	( Passive membrane transport of lignin-related compounds. Beckham, GT; Boerjan, W; Chen, F; Crowley, MF; Dixon, RA; Mansfield, SD; Ralph, J; Vermaas, JV, 2019)	2.25
"Lignin is a renewable source of aromatics, and the conversion of lignin to chemicals, fuels and materials is very attractive. "	( One-pot preparation and characterization of lignin-based cation exchange resin and its utilization in Pb (II) removal. Cao, X; Chen, X; Shi, Q; Sun, R; Sun, S; Wang, S; Wang, X; Wang, Y; Wen, J; Yuan, T, 2020)	2.26
"Lignin is a major component of lignocellulosic biomass. "	( Unassisted solar lignin valorisation using a compartmented photo-electro-biochemical cell. Jang, JW; Joo, SH; Kim, JH; Kim, YH; Ko, M; Nguyen, TVT; Oh, D; Pham, LTM; Ryu, J; Sa, YJ; Sharma, P; Shin, TJ; Woo, J, 2019)	2.3
"Lignin is a complex phenylpropanoid polymer deposited in plant cell walls. "	( Altered lignocellulose chemical structure and molecular assembly in CINNAMYL ALCOHOL DEHYDROGENASE-deficient rice. Koshiba, T; Kusumi, R; Lam, PY; Martin, AF; Matsumoto, N; Miyamoto, T; Sakamoto, M; Tobimatsu, Y; Umezawa, T; Yamamura, M, 2019)	1.96
"Lignin is a major component of secondarily thickened plant cell walls and is considered to be the second most abundant biopolymer on the planet. "	( Lignin biosynthesis: old roads revisited and new roads explored. Barros, J; Dixon, RA, 2019)	3.4
"Lignin (LIG) is a renewable biopolymer with well-known antimicrobial and antioxidant properties. "	( Lignin/poly(butylene succinate) composites with antioxidant and antibacterial properties for potential biomedical applications. Delgado-Aguilar, M; Domínguez-Robles, J; Fong, ML; Irwin, NJ; Larrañeta, E; Martin, NK; Mutjé, P; Tarrés, Q, 2020)	3.44
"Lignin is a phenylpropanoid-derived polymer that functions as a major component of cell walls in plant vascular tissues. "	( MYB20, MYB42, MYB43, and MYB85 Regulate Phenylalanine and Lignin Biosynthesis during Secondary Cell Wall Formation. Cao, Y; Fu, C; Geng, P; Han, X; He, H; Liu, J; Wu, J; Zhang, S; Zhao, C; Zhao, Q, 2020)	2.25
"Lignin is a complex phenolic biopolymer found mainly in the secondary cell walls of vascular plants, where it contributes to mechanical strength, water conduction, and plant defence. "	( Atypical lignification in eastern leatherwood (Dirca palustris). Gierlinger, N; Jeremic, D; Mansfield, SD; Master, ER; Mottiar, Y, 2020)	2
"Lignin is a major component of cell wall biomass and decisively affects biomass utilisation. "	( Fibre-specific regulation of lignin biosynthesis improves biomass quality in Populus. Cao, S; Gui, J; Huang, C; Lam, PY; Li, L; Sun, J; Tobimatsu, Y; Umezawa, T; Zhong, Y, 2020)	2.29
"Lignin is a highly complex, plant-derived natural biomass component, the analysis of which requires significant demands on the analytical platform. "	( Assessment of molecular diversity of lignin products by various ionization techniques and high-resolution mass spectrometry. Fu, P; Li, S; Liu, C; Ma, C; Qi, Y; Volmer, DA, 2020)	2.27
"Lignin is a good candidate for the polymerization and chemical modification to prepare sustainable chemicals and materials, but a relatively low hydroxyl content becomes an obstacle for the preparation of lignin-based polyurethane (PU) adhesives. "	( High-value utilization of hydroxymethylated lignin in polyurethane adhesives. Chen, Y; Fu, S; Zhang, H; Zhu, Z, 2020)	2.26
"Lignin is an abundant and recalcitrant component of plant cell walls. "	( Outer membrane vesicles catabolize lignin-derived aromatic compounds in Abraham, PE; Amore, A; Beckham, GT; Black, BA; Donohoe, BS; Giannone, RJ; Haugen, SJ; Hettich, RL; Katahira, R; Laible, PD; Michalska, M; Notonier, S; Pardo, I; Poudel, S; Purvine, SO; Ramirez, KJ; Salvachúa, D; Werner, AZ; Zink, EM, 2020)	2.28
"Lignin is a heterogeneous aromatic polymer responsible for cell wall stiffness and protection from pathogen attack. "	( Correlations between lignin content and structural robustness in plants revealed by X-ray ptychography. Barsi-Andreeta, M; Flores-Borges, DNA; Guizar-Sicairos, M; Holler, M; Mayer, JLS; Mazzafera, P; Meneau, F; Pereira, L; Polo, CC; Westfahl, H, 2020)	2.32
"Lignin, which is a naturally abundant polyphenol-rich biopolymer, can be utilized for the fabrication of sustainable antimicrobial materials."	( Lignin-Bimetallic Nanoconjugate Doped pH-Responsive Hydrogels for Laser-Assisted Antimicrobial Photodynamic Therapy. Bhaumik, J; Chandna, S; Kaur, R; Thakur, NS, 2020)	2.72
"Lignin is an aromatic biopolymer derived from lignocellulosic biomass. "	( Study of the Reactivity of Lignin Model Compounds to Fluorobenzylation Using Brochier-Salon, MC; Esakkimuthu, ES; Marlin, N; Mortha, G, 2020)	2.3
"Lignin is a unique biomacromolecule with three dimensional network structure, large molecular weight, and aromatic structure."	( Novel lignin-containing high-performance adhesive for extreme environment. Chen, T; Han, Y; Li, Y; Sun, G; Sun, Y; Zhang, H, 2020)	1.76
"Lignin is a natural, renewable resource with potential to be used in biomaterials. "	( Levulinic acid: A novel sustainable solvent for lignin dissolution. Antunes, FE; Filipe, A; Medronho, B; Melro, E; Norgren, M; Romano, A; Valente, AJM, 2020)	2.26
"Lignin is a potential biomass feedstock from plant material, but it is particularly difficult to economically process. "	( Improving the Yield and Rate of Acid-Catalyzed Deconstruction of Lignin by Mechanochemical Activation. East, ALL; Marx, D; Patel, DH, 2020)	2.24
"Lignin is an important renewable energy source as an excellent new battery fuel and ideal substitutes for the petrochemical industry. "	( Integrative analysis of wood biomass and developing xylem transcriptome provide insights into mechanisms of lignin biosynthesis in wood formation of Pinus massoniana. Chen, Y; Feng, Y; Han, X; Ni, Z; Xu, LA; Xu, M; Yang, Z, 2020)	2.21
"Lignin is a water-insoluble dietary fiber, but it is second only to cellulose in abundance."	( AgNAC1, a celery transcription factor, related to regulation on lignin biosynthesis and salt tolerance. Chen, LZ; Duan, AQ; Feng, K; Jia, LL; Li, T; Liu, JX; Su, XJ; Tan, GF; Tao, JP; Xiong, AS; Xu, ZS, 2020)	1.52
"Lignin is an aromatic-rich biomass polymer that is cheap, abundant, and sustainable. "	( Lignin-Based Solid Polymer Electrolytes: Lignin-Graft-Poly(ethylene glycol). Chung, H; Hallinan, D; Liu, H; Mulderrig, L, 2021)	3.51
"Lignin is a key target for modifying lignocellulosic biomass for efficient biofuel production. "	( Loss of COMT activity reduces lateral root formation and alters the response to water limitation in sorghum brown midrib (bmr) 12 mutant. Saluja, M; Sattler, SE; Walia, H; Yu, H; Zhu, F, 2021)	2.06
"Lignin is a recalcitrant macromolecule formed by three alcohols (monolignols) predominantly connected by β-aryl ether linkages and is one of the most abundant organic macromolecules in the biosphere. "	( Complete genome reveals genetic repertoire and potential metabolic strategies involved in lignin degradation by environmental ligninolytic Klebsiella variicola P1CD1. Bruce, T; de Abreu Roque, MR; Dos Santos Melo-Nascimento, AO; Gonçalves, CC; Mota Moitinho Sant Anna, B; Noronha, E; Parachin, N; Santos, G, 2020)	2.22
"C-lignin is a homo-biopolymer, being made up of caffeyl alcohol exclusively. "	( Selective hydrogenolysis of catechyl lignin into propenylcatechol over an atomically dispersed ruthenium catalyst. Li, H; Song, G; Wang, S; Xiao, LP; Zhang, K, 2021)	1.62
"Lignin is an under-explored natural biopolymer with multifaceted potential."	( Development of a light activatable lignin nanosphere based spray coating for bioimaging and antimicrobial photodynamic therapy. Bhaumik, J; Chandna, S; Paul, S; Reddy, YN; Thakur, NS, 2021)	1.62
"Lignin is a biopolymer found in plant cell walls that accounts for 30% of the organic carbon in the biosphere. "	( Intracellular pathways for lignin catabolism in white-rot fungi. Burnet, MC; Cheng, JF; Chu, RK; Del Cerro, C; Dong, T; Eder, EK; Erickson, E; Himmel, ME; Hoyt, DW; Katahira, R; Linger, JG; Markillie, LM; Mitchell, HD; Purvine, SO; Ramirez, KJ; Salvachúa, D; Subramanian, V; Weitz, KK; Wong, AR; Xiong, W, 2021)	2.36
"Lignin is a natural polymer interlaced with cellulose and hemicellulose in secondary cell walls (SCWs). "	( Advances in the role of auxin for transcriptional regulation of lignin biosynthesis. Chen, X; Cheng, X; Deng, X; Ji, W; Lv, Q; Peng, D; Qu, G; Yang, Y; Ye, T; Yu, Z; Zhou, B, 2021)	2.3
"Lignin is an abundant renewable natural biopolymer. "	( Lignin: Drug/Gene Delivery and Tissue Engineering Applications. Aadil, KR; Bunekar, N; Butreddy, A; Dutt, S; Kaushik, A; Kommineni, N; Kumar, R; Mishra, VK; Mishra, YK; Oupicky, D; Reddy, PG; Sarkar, C, 2021)	3.51
"Lignin is a complex polymer deposited in the cell wall of specialised plant cells, where it provides essential cellular functions. "	( Two chemically distinct root lignin barriers control solute and water balance. Boerjan, W; Boursiac, Y; Calvo-Polanco, M; Castrillo, G; Flis, P; Fujita, S; Geldner, N; George, MW; Lapierre, C; Love, A; Morreel, K; Ramakrishna, P; Reyt, G; Salas-González, I; Salt, DE; Tiemessen, D, 2021)	2.36
"Lignin is a complex phenolic biopolymer present in plant cell walls and a by-product of the cellulose pulping industry. "	( Safety aspects of kraft lignin fractions: Discussions on the in chemico antioxidant activity and the induction of oxidative stress on a cell-based in vitro model. Avelino, F; Cestari, MM; Gagosian, VSC; Leme, DM; Lomonaco, D; Magalhães, WLE; Matos, M; Rodrigues-Souza, I; Thá, EL, 2021)	2.37
"Lignin is an abundant natural plant aromatic biopolymer containing various functional groups that can be exploited for activating lignin for potential commercial applications. "	( Microbial demethylation of lignin: Evidence of enzymes participating in the removal of methyl/methoxyl groups. Dekker, RFH; Venkatesagowda, B, 2021)	2.36
"Lignin is a large molecule aromatic polymer and a major cell wall component."	( Comparative transcriptomic analysis of seed coats with high and low lignin contents reveals lignin and flavonoid biosynthesis in Brassica napus. Ding, Y; Li, J; Li, M; Liu, L; Qu, C; Wang, J; Yu, S, 2021)	1.58
"Lignin is an important component of the healing tissue in fruits. "	( Effects of nitric oxide treatment on lignin biosynthesis and texture properties at wound sites of muskmelons. Bi, Y; Han, Z; Li, Z; Prusky, D; Wang, B; Xue, S, 2021)	2.34
"Lignin is an abundant natural polyphenol that can be used to cure epoxies, but its poor water solubility has impeded the use of unmodified lignin in coatings in the past."	( Colloidal Lignin Particles and Epoxies for Bio-Based, Durable, and Multiresistant Nanostructured Coatings. Forsman, N; Henn, KA; Österberg, M; Zou, T, 2021)	1.75
"Lignin is a low-cost and environmental-friendly material and could increase the solubility of phosphorus (P) in soils. "	( Effect of alkaline lignin on immobilization of cadmium and lead in soils and the associated mechanisms. Dai, Z; He, L; Liu, X; Tang, C; Xu, J, 2021)	2.39
"Lignin is a promising renewable resource and its valorization could help to reduce our dependency on fossil carbon resources. "	( Separation of monomeric and dimeric phenolic compounds in lignosulphonate lignin on different stationary phases using ultrahigh-performance supercritical fluid chromatography. Palmer, S; Prothmann, J; Sandahl, M; Turner, C, 2021)	2.29
"Lignin is a natural polymer that is the second most abundant polymer on Earth after cellulose. "	( Estimation of Plant Biomass Lignin Content using Thioglycolic Acid (TGA). Dampanaboina, L; Mendu, V; Yuan, N, 2021)	2.36
"Lignin is a wasted renewable source of biomass-derived value-added chemicals. "	( Enzymatic bioconversion process of lignin: mechanisms, reactions and kinetics. Cajnko, MM; Grilc, M; Likozar, B; Oblak, J, 2021)	2.34
"Lignin engineering is a promising tool to reduce the energy input and the need of chemical pre-treatments for the efficient conversion of plant biomass into fermentable sugars for downstream applications. "	( Unravelling the impact of lignin on cell wall mechanics: a comprehensive study on young poplar trees downregulated for CINNAMYL ALCOHOL DEHYDROGENASE (CAD). Boerjan, W; Burgert, I; Cesarino, I; Gierlinger, N; Özparpucu, M; Rüggeberg, M; Vanholme, R, 2017)	2.2
"Lignin is a versatile plant metabolite challenging high-end industrial applications of several plant products including jute. "	( Morphological, Histobiochemical and Molecular Characterisation of Low Lignin Phloem Fibre (llpf) Mutant of Dark Jute (Corchorus olitorius L.). Anil Kumar, A; Choudhary, SB; Chowdhury, I; Jambhulkar, SJ; Karmakar, PG; Kumari, N; Pandey, SP; Sharma, HK; Singh, RK; Souframanien, J, 2017)	2.13
"Lignin is a biomass-derived aromatic polymer that has been identified as a potential renewable source of aromatic chemicals and other valuable compounds. "	( Multi-step biocatalytic depolymerization of lignin. Anders, N; Domínguez de María, P; Grande, PM; Klankermayer, J; Leitner, W; Liu, H; Picart, P; Schallmey, A; Schwaneberg, U; Zhu, L, 2017)	2.16
"Lignin is an important secondary metabolite possessing a great effect on plant growth and product quality."	( Identification of critical genes associated with lignin biosynthesis in radish (Raphanus sativus L.) by de novo transcriptome sequencing. Feng, H; Liu, L; Muleke, EM; Nie, S; Sun, X; Tang, M; Wang, Y; Xu, L; Zhang, W; Zhu, X, 2017)	1.43
"Lignin is a natural, renewable biopolymer synthesized by plants. "	( Softwood Lignin Self-Assembly for Nanomaterial Design. Salentinig, S; Schubert, M, 2017)	2.31
"Lignin is a polyphenolic polymer of the plant cell wall formed by the oxidative polymerization of 3 main monomers called monolignols that give rise to the lignin H-, G- and S-units. "	( BLISS: Shining a light on lignification in plants. Biot, C; Blervacq, AS; Guérardel, Y; Hawkins, S; Huss, B; Lion, C; Simon, C; Spriet, C, 2017)	1.9
"Lignin is an aromatic heteropolymer forming a physical barrier and it is a big challenge in biomass utilization. "	( Isolation, identification and characterization of lignin-degrading bacteria from Qinling, China. Gao, LN; Lü, X; Wang, T; Yang, CX; Yin, HJ, 2017)	2.15
"Lignin valorization is a pending issue for the integrated conversion of lignocellulose in consumer goods. "	( High-Throughput Screening Assay for Laccase Engineering toward Lignosulfonate Valorization. Camarero, S; de Salas, F; Pardo, I; Rodríguez-Escribano, D, 2017)	1.9
"Lignin is a major factor determining saccharification efficiency and, therefore, is a prime target to engineer."	( Different Routes for Conifer- and Sinapaldehyde and Higher Saccharification upon Deficiency in the Dehydrogenase CAD1. Boerjan, W; Déjardin, A; Desmet, S; Foster, C; Goeminne, G; Hoengenaert, L; Kim, H; Lapierre, C; Laurans, F; Légée, F; Morreel, K; Pilate, G; Ralph, J; Santoro, N; Van Acker, R; Vanholme, R, 2017)	1.18
"Lignin is a huge energy and carbon reserve but owing to its highly biologically recalcitrant nature it is commonly regarded as a waste in lignocellulosic biomass biorefinery. "	( Kraft lignin biorefinery: A perspective. Hu, J; Lee, DJ; Zhang, Q, 2018)	2.4
"Lignin is an important component of many plant secondary cell walls. "	( EjNAC3 transcriptionally regulates chilling-induced lignification of loquat fruit via physical interaction with an atypical CAD-like gene. Chen, KS; Ge, H; Grierson, D; Li, X; Yin, XR; Zhang, J; Zhang, YJ, 2017)	1.9
"Lignin is a vastly underutilized biomass resource. "	( Preparation of Lignin/Sodium Dodecyl Sulfate Composite Nanoparticles and Their Application in Pickering Emulsion Template-Based Microencapsulation. Huang, J; Lou, H; Luo, Y; Pang, Y; Qiu, X; Wang, S, 2017)	2.25
"Lignin is a complex, phenolic polymer found in plant cell walls that is essential for mechanical support, water and mineral transport, and defense in vascular plants. "	( The impact of lignin downregulation on alfalfa yield, chemical composition, and in vitro gas production. DePeters, EJ; Getachew, G; Laca, EA; McCaslin, M; Ortega, KP; Putnam, DH; Witte, D, 2018)	2.28
"Lignin is an important phenolic biopolymer that provides strength and rigidity to the secondary cell walls of tracheary elements, sclereids, and fibers in vascular plants. "	( Distribution, mobility, and anchoring of lignin-related oxidative enzymes in Arabidopsis secondary cell walls. Hoffmann, N; Samuels, AL; Schuetz, M; Sibout, R; Watanabe, Y; Yi Chou, E, 2018)	2.19
"Lignin is a natural phenylpropanoid polymer, commonly found in secondary cell walls of vascular plants."	( Host lignin composition affects haustorium induction in the parasitic plants Phtheirospermum japonicum and Striga hermonthica. Cui, S; Saucet, SB; Shirasu, K; Takano, T; Takeda, Y; Tobimatsu, Y; Umezawa, T; Wada, S; Yoshida, S, 2018)	1.72
"Lignin is a polymer present in the secondary cell walls of all vascular plants. "	( Assessing the impact of the 4CL enzyme complex on the robustness of monolignol biosynthesis using metabolic pathway analysis. Chiang, V; Ducoste, JJ; Naik, P; Sederoff, R; Wang, JP; Williams, C, 2018)	1.92
"Lignin is a main challenge in the conversion of cell wall sugars into ethanol."	( Optimization of RT-PCR reactions in studies with genes of lignin biosynthetic route in Saccharum spontaneum. Araújo, P; Llerena, JPP; Mazzafera, P, )	1.1
"Lignin is a complex natural polymer and it is one of the main constituent of the lignocellulosic biomass. "	( Lignin-based hydrogels with "super-swelling" capacities for dye removal. Domínguez-Robles, J; Jääskeläinen, AS; Larrañeta, E; Peresin, MS; Rodríguez, A; Tamminen, T, 2018)	3.37
"Lignin is an increasingly valuable raw material for industrial, pharmaceutical and the food industries; natural antioxidants are also being used more and more widely. "	( Structural characterization of Chinese quince fruit lignin pretreated with enzymatic hydrolysis. Liu, HM; Qin, GY; Qin, Z; Wang, DM; Wang, XD, 2018)	2.17
"Lignin is a complex and irregular biopolymer of crosslinked phenylpropanoid units in plant secondary cell walls. "	( The scaffold proteins of lignin biosynthetic cytochrome P450 enzymes. Gou, M; Liu, CJ; Martin, DW; Ran, X, 2018)	2.23
"As lignin is an important component of wood and the water transport system, we investigated its relationship with embolism resistance and the LL of several tree species in a seasonally dry tropical ecosystem."	( Lignin composition is related to xylem embolism resistance and leaf life span in trees in a tropical semiarid climate. Araújo, FS; Bittencourt, PRL; Carvalho, ECD; Costa, RC; Gomes-Filho, E; Lima, TRA; Martins, FR; Miranda, RS; Müller, CS; Oliveira, RS; Pereira, L; Sobczak, JCMSM, 2018)	2.44
"Lignin is an aromatic polymer that makes a network by intertwining between cellulose fibers in plant. "	( Screening of fungi for decomposition of lignin-derived products from Japanese cedar. Kawashima, M; Kikuchi, J; Makita, Y; Matsui, M; Matsumoto, T; Saito, Y; Tsuchida, H, 2018)	2.19
"Lignin is a polymer that significantly inhibits saccharification of plant feedstocks. "	( Dynamic modeling of subcellular phenylpropanoid metabolism in Arabidopsis lignifying cells. Chapple, C; Dudareva, N; Guo, L; Jaini, R; Morgan, JA; Wang, P, 2018)	1.92
"Lignin is a complex aromatic heteropolymer that plays essential roles in mechanical support, water transport, and response to biotic and abiotic stresses. "	( Identification of genes revealed differential expression profiles and lignin accumulation during leaf and stem development in tea plant (Camellia sinensis (L.) O. Kuntze). Shen, W; Teng, RM; Wang, WL; Wang, Y; Wang, YX; Zhuang, J, 2019)	2.19
"Lignin is an abundant biomass resource in aromatic structure with a low price in market, which can serve as renewable precursors of value-added products. "	( Lignin valorization for the production of renewable chemicals: State-of-the-art review and future prospects. Cao, L; Hunt, AJ; Liu, Y; Ok, YS; Ruan, X; Song, H; Tsang, DCW; Yu, IKM; Zhang, S, 2018)	3.37
"Lignin is a highly abundant polymer in plant cell walls that is essential for land plants' ability to stand upright and transport water. "	( The transport of monomers during lignification in plants: anything goes but how? Perkins, M; Samuels, L; Smith, RA, 2019)	1.96
"Lignin is a highly aromatic low value biomass residue, which can be utilized for chemicals, fuels and materials production. "	( Lignin materials for adsorption: Current trend, perspectives and opportunities. Hunt, AJ; Jetsrisuparb, K; Knijnenburg, JTN; Supanchaiyamat, N; Tsang, DCW, 2019)	3.4
"Lignin is an important secondary metabolite in plants. "	( The quest for transcriptional hubs of lignin biosynthesis: beyond the NAC-MYB-gene regulatory network model. Demura, T; Ohtani, M, 2019)	2.23
"Lignin is a byproduct in the pulp and paper industry and is considered as a promising alternative for the provision of energy and chemicals. "	( Bioconversion of lignin into bioplastics by Pandoraea sp. B-6: molecular mechanism. Chai, L; Deng, X; Liu, D; Min, X; Shi, Y; Si, M; Yan, X, 2019)	2.3
"Lignin is a high added-value product obtained from agrowastes through organosolv process to yield materials for technological applications. "	( Poly(methyl methacrylate) films reinforced with coconut shell lignin fractions to enhance their UV-blocking, antioxidant and thermo-mechanical properties. Avelino, F; de Oliveira, DR; Lomonaco, D; Mazzetto, SE, 2019)	2.2
"Lignin is a heterogeneous polymer of aromatic subunits that is a major component of lignocellulosic plant biomass. "	( A heterodimeric glutathione Beebe, ET; Donohue, TJ; Gall, DL; Karlen, SD; Kontur, WS; Niles, AV; Noguera, DR; Olmsted, CN; Vander Meulen, KA; Walters, KA; Yusko, LM, 2019)	1.96
"Lignin is a kind of natural fluorescent polymer material. "	( Lignosulfonate: A Convenient Fluorescence Resonance Energy Transfer Platform for the Construction of a Ratiometric Fluorescence pH-Sensing Probe. Ouyang, X; Qiu, X; Wan, Z; Xue, Y, 2019)	1.96
"Lignin is a complex aromatic biopolymer that strengthens and waterproofs plant secondary cell walls, enabling mechanical stability in trees and long-distance water transport in xylem. "	( Lignin-polysaccharide interactions in plant secondary cell walls revealed by solid-state NMR. Cosgrove, DJ; Dickwella Widanage, MC; Kang, X; Kirui, A; Mentink-Vigier, F; Wang, T, 2019)	3.4
"Lignin is a phenolic macromolecule, the principal biological source of aromatic structures, with a complex structure which varies depending on plant species and its isolation process."	( Valorization of lignin in polymer and composite systems for advanced engineering applications - A review. Collins, MN; Culebras, M; McLoughlin, A; Nechifor, M; Stróżyk, MA; Tanasă, F; Teacă, CA; Zănoagă, M, 2019)	1.58
"Lignin is a principal structural component of cell walls in higher terrestrial plants. "	( Lignin biosynthesis and its integration into metabolism. Boerjan, W; De Meester, B; Ralph, J; Vanholme, R, 2019)	3.4
"Lignin is a natural anti-UV active ingredient with great potential applications."	( Preparation of organic acid lignin submicrometer particle as a natural broad-spectrum photo-protection agent. Bian, J; Li, MF; Li, SX; Ma, MG; Peng, F; Wu, XF, 2019)	1.53
"Lignin is a heterogeneous aromatic biopolymer and a major constituent of lignocellulosic biomass, such as wood and agricultural residues. "	( Mapping the diversity of microbial lignin catabolism: experiences from the eLignin database. Brink, DP; Gorwa-Grauslund, MF; Lidén, G; Ravi, K, 2019)	2.23
"C-lignin is a linear polymer of caffeyl alcohol, found in the seed coats of several exotic plant species, with promising properties for generation of carbon fibers and high value chemicals. "	( Enzymatic basis for C-lignin monomer biosynthesis in the seed coat of Cleome hassleriana. Azad, R; Chen, F; Dixon, RA; Harkelroad, A; Pandey, R; Rao, X; Wang, X; Xiao, X; Zhuo, C, 2019)	1.55
"Root lignin is a key driver of root decomposition, which in turn is a fundamental component of the terrestrial carbon cycle and increasingly in the focus of ecologists and global climate change research."	( Fine root lignin content is well predictable with near-infrared spectroscopy. Elle, O; Richter, R; Vohland, M; Weigelt, A, 2019)	1.37
"Lignin is a cell wall component of vascular plants crucial for survival in terrestrial environments. "	( Proton Gradient-Dependent Transport of p-Glucocoumaryl Alcohol in Differentiating Xylem of Woody Plants. Fukushima, K; Kamei, I; Matsushita, Y; Takabe, K; Tsuyama, T; Yazaki, K, 2019)	1.96
"Lignin is a robust material that is considered useless because it has an inhibitory effect on microbes and acts as a physical barrier for cellulose degradation. "	( Studies of advanced lignin valorization based on various types of lignolytic enzymes and microbes. Han, SO; Hyeon, JE; Ko, YJ; Shin, SK, 2019)	2.28
"Lignin is a complex phenolic heteropolymer deposited in the secondarily thickened walls of specialized plant cells to provide strength for plants to stand upright and hydrophobicity to conducting cells for long-distance water transport. "	( Expression of SofLAC, a new laccase in sugarcane, restores lignin content but not S:G ratio of Arabidopsis lac17 mutant. Araújo, P; Berthet, S; Boerjan, W; Cesarino, I; Demedts, B; Mazzafera, P; Sampaio Mayer, JL; Vanholme, B; Vicentini, R, 2013)	2.08
"Lignin is a good candidate for photocatalytic cracking due to the presence of hydroxyl groups. "	( Effect of the photocatalytic activity of TiO₂ on lignin depolymerization. Erdocia, X; Labidi, J; Prado, R, 2013)	2.09
"Lignin is a major cell wall modification that often forms intricate subcellular patterns that are central to cellular function."	( A mechanism for localized lignin deposition in the endodermis. Alassimone, J; Geldner, N; Lee, Y; Rubio, MC, 2013)	1.41
"Lignin biosynthesis is an essential physiological activity of vascular plants if they are to survive under various environmental stresses on land. "	( Proton-dependent coniferin transport, a common major transport event in differentiating xylem tissue of woody plants. Fujita, M; Kawai, R; Matoh, T; Shitan, N; Sugiyama, J; Takabe, K; Tsuyama, T; Yazaki, K; Yoshinaga, A, 2013)	1.83
"Lignin is a constituent of plant cell walls and thus is classified as part of dietary fiber. "	( Interactions of a lignin-rich fraction from brewer's spent grain with gut microbiota in vitro. Aura, AM; Buchert, J; Faulds, CB; Mattila, I; Maukonen, J; Niemelä, K; Niemi, P; Poutanen, K; Smeds, AI; Tamminen, T, 2013)	2.17
"Lignin is a potential renewable material for the production of bio-sourced aromatic chemicals. "	( Aromatic chemicals by iron-catalyzed hydrotreatment of lignin pyrolysis vapor. Aubriet, F; Bettahar, M; Carré, V; Dufour, A; Fontana, S; Ghanbaja, J; Lardier, G; Olcese, RN; Petitjean, D, 2013)	2.08
"Lignin is a high-molecular amorphous material that forms plants together with cellulose and hemicelluloses, in which phenylpropane fundamental units are complexly condensed."	( Lignin Induces ES Cells to Differentiate into Neuroectodermal Cells through Mediation of the Wnt Signaling Pathway. Akamatsu, H; Date, Y; Hasegawa, S; Inoue, Y; Mizutani, H; Nakata, S; Yamada, T, 2013)	2.55
"Lignin is an abundant phenylpropanoid polymer produced by the oxidative polymerization of p-hydroxycinnamyl alcohols (monolignols). "	( Visualization of plant cell wall lignification using fluorescence-tagged monolignols. Anderson, N; Boerjan, W; Chapple, C; Dima, O; Donaldson, L; Kim, JI; Loque, D; Mitra, P; Niculaes, C; Ralph, J; Tobimatsu, Y; Wagner, A, 2013)	1.83
"Lignin is a significant barrier in the conversion of plant biomass to bioethanol. "	( Functional characterization of cinnamyl alcohol dehydrogenase and caffeic acid O-methyltransferase in Brachypodium distachyon. Hazen, SP; Lee, SJ; Matos, DA; Mockler, TC; Priest, HD; Saathoff, AJ; Sarath, G; Trabucco, GM, 2013)	1.83
"Lignin is a major component of plant secondary cell walls. "	( Caffeoyl shikimate esterase (CSE) is an enzyme in the lignin biosynthetic pathway in Arabidopsis. Araujo, P; Boerjan, W; Cesarino, I; Cross, J; Goeminne, G; Halpin, C; Haustraete, J; Kim, H; McClellan, C; Morreel, K; Ralph, J; Rataj, K; Simpson, GG; Sundin, L; Vanholme, B; Vanholme, R; Welsh, L; Xiao, Y, 2013)	2.08
"Lignin is a polyphenolic macromolecule considered resilient toward breakdown and utilization by colon microbiota, although some indications of release of small phenolic components from lignin in animals have been shown."	( Release of small phenolic compounds from brewer's spent grain and its lignin fractions by human intestinal microbiota in vitro. Aura, AM; Buchert, J; Faulds, C; Mattila, I; Niemelä, K; Niemi, P; Poutanen, K; Smeds, A; Tamminen, T, 2013)	1.35
"Lignin is a critical structural component of plants, providing vascular integrity and mechanical strength. "	( Neighboring parenchyma cells contribute to Arabidopsis xylem lignification, while lignification of interfascicular fibers is cell autonomous. Ellis, B; Mansfield, SD; Roach, M; Samuels, L; Schuetz, M; Smith, RA, 2013)	1.83
"Lignin is an aromatic plant compound that decomposes more slowly than other organic matter compounds; however, it was recently shown that lignin could decompose as fast as litter bulk carbon in minerals soils. "	( Lignin decomposition along an Alpine elevation gradient in relation to physicochemical and soil microbial parameters. Dignac, MF; Djukic, I; Duboc, O; Gerzabek, MH; Rumpel, C; Zehetner, F, 2014)	3.29
"Lignin is a complex, branched polymer that reinforces plant tissue. "	( Chemical factors that control lignin polymerization. Davis, MF; Davison, BH; Parks, JM; Sangha, AK; Smith, JC; Standaert, RF, 2014)	2.13
"Lignin is a plant component with important implications for various agricultural disciplines. "	( Lignin: characterization of a multifaceted crop component. Frei, M, 2013)	3.28
"Lignin is a phenylpropanoid-derived heteropolymer important for the strength and rigidity of the plant secondary cell wall. "	( Disruption of Mediator rescues the stunted growth of a lignin-deficient Arabidopsis mutant. Anderson, NA; Bonawitz, ND; Chapple, C; Ciesielski, PN; Donohoe, BS; Kim, JI; Ladisch, M; Maeda, J; Ralph, J; Tobimatsu, Y; Ximenes, E, 2014)	2.09
"Lignin pyrolysis is a promising method for the sustainable production of phenolic compounds from biomass. "	( In situ observation of radicals and molecular products during lignin pyrolysis. Bährle, C; Custodis, V; Jeschke, G; van Bokhoven, JA; Vogel, F, 2014)	2.09
"Lignin is an energy-dense, heterogeneous polymer comprised of phenylpropanoid monomers used by plants for structure, water transport, and defense, and it is the second most abundant biopolymer on Earth after cellulose. "	( Lignin valorization through integrated biological funneling and chemical catalysis. Beckham, GT; Chupka, G; Franden, MA; Guarnieri, MT; Hunsinger, GB; Johnson, CW; Karp, EM; Linger, JG; Pienkos, PT; Strathmann, TJ; Vardon, DR, 2014)	3.29
"Lignin is a heterogeneous aromatic biopolymer that accounts for nearly 30% of the organic carbon on Earth and is one of the few renewable sources of aromatic chemicals. "	( Formic-acid-induced depolymerization of oxidized lignin to aromatics. Coon, JJ; Rahimi, A; Stahl, SS; Ulbrich, A, 2014)	2.1
"Lignin is an abundant and essential polymer in land plants. "	( Development of a clickable designer monolignol for interrogation of lignification in plant cell walls. Anderson, CT; Bukowski, N; Doyle, L; Pandey, JL; Richard, TL; Zhu, Y, 2014)	1.85
"Lignin is a major part of the recalcitrant fraction of lignocellulose and in nature its degradation occurs through oxidative enzymes along with microbes mediated oxidative chemical actions. "	( Making lignin accessible for anaerobic digestion by wet-explosion pretreatment. Ahamed, A; Ahring, BK; Biswas, R; Teller, PJ; Uellendahl, H, 2015)	2.31
"Lignin is an aromatic polymer derived from the combinatorial coupling of monolignol radicals in the cell wall. "	( Small glycosylated lignin oligomers are stored in Arabidopsis leaf vacuoles. Boerjan, W; Dima, O; Kim, H; Morreel, K; Ralph, J; Vanholme, B, 2015)	2.19
"Lignin is a polyphenolic polymer that strengthens and waterproofs the cell wall of specialized plant cell types. "	( The cell biology of lignification in higher plants. Barros, J; Granlund, I; Pesquet, E; Serk, H, 2015)	1.86
"Lignin is a complex polyphenolic heteropolymer that is abundant in the secondary cell walls of plants and functions in growth and defence. "	( Imaging with the fluorogenic dye Basic Fuchsin reveals subcellular patterning and ecotype variation of lignification in Brachypodium distachyon. Anderson, CT; Barnes, WJ; Kapp, N; Richard, TL, 2015)	1.86
"Biolignin is a mixture of low molar mass compounds (Mn = 1660 g/mol) made up of S, G, and H units and of coumaric and ferulic acid units."	( Purification, structural characterization, and modification of organosolv wheat straw lignin. Duong, KL; Fradet, A; Le Morvan, C; Mbotchak, L; Rousseau, B; Tessier, M, 2015)	1.15
"Lignin is an important raw material for the sustainable biorefineries and also the forerunner of high-value added products, such as biocomposite for chemical, pharmaceutical and cement industries. "	( Lignin preparation from oil palm empty fruit bunches by sequential acid/alkaline treatment--A biorefinery approach. Kaur, BS; Medina, JD; Noseda, MD; Soccol, CR; Woiciechowski, A; Zandona Filho, A, 2015)	3.3
"Lignin is a major factor limiting the use of bagasse and other plant lignocellulosic materials to produce second-generation ethanol."	( Large-Scale Transcriptome Analysis of Two Sugarcane Genotypes Contrasting for Lignin Content. Bottcher, A; Brito, Mdos S; Cesarino, I; Creste, S; Dos Santos, AB; Landell, MG; Mazzafera, P; Vicentini, R, 2015)	1.37
"Lignin is an important factor affecting agricultural traits, biofuel production, and the pulping industry. "	( Roles of lignin biosynthesis and regulatory genes in plant development. An, G; Choi, H; Yoon, J, 2015)	2.28
"Lignin is a complex polymer that is a potential feedstock for aromatic compounds and carboxylic acids by cleaving the β-O-4 and 5-5' linkages. "	( Gas-Phase Partial Oxidation of Lignin to Carboxylic Acids over Vanadium Pyrophosphate and Aluminum-Vanadium-Molybdenum. Boffito, DC; Lotfi, S; Patience, GS, 2015)	2.15
"Lignin is a complex aromatic polymer found in plant cell walls that makes up 15 to 40% of plant biomass. "	( Phylogenetic and kinetic characterization of a suite of dehydrogenases from a newly isolated bacterium, strain SG61-1L, that catalyze the turnover of guaiacylglycerol-β-guaiacyl ether stereoisomers. Dellas, N; Oakeshott, JG; Palamuru, S; Pandey, G; Pearce, SL; Warden, AC, 2015)	1.86
"Lignin is a component of the cell wall that is essential for growth, development, structure and pathogen resistance in plants, but high lignin is an obstacle to the conversion of cellulose to ethanol for biofuel. "	( Co-downregulation of the hydroxycinnamoyl-CoA:shikimate hydroxycinnamoyl transferase and coumarate 3-hydroxylase significantly increases cellulose content in transgenic alfalfa (Medicago sativa L.). Dong, J; Li, H; Ma, L; Tong, Z; Wang, T; Zhang, R, 2015)	1.86
"Lignin is an essential polymer in vascular plants that plays key structural roles in vessels and fibers. "	( A MYB/ZML Complex Regulates Wound-Induced Lignin Genes in Maize. Caparros-Ruiz, D; Fornalé, S; Franco-Zorrilla, JM; Gray, J; Grotewold, E; López-Vidriero, I; Pagés, M; Riera, M; Salazar-Henao, JE; Schmidt, W; Solano, R; Vélez-Bermúdez, IC, 2015)	2.12
"Lignin is a highly abundant source of renewable carbon that can be considered as a valuable sustainable source of biobased materials. "	( Lignin-Derived Advanced Carbon Materials. Chatterjee, S; Saito, T, 2015)	3.3
"Lignin is a combinatorial polymer comprising monoaromatic units that are linked via covalent bonds. "	( Structural Basis of Stereospecificity in the Bacterial Enzymatic Cleavage of β-Aryl Ether Bonds in Lignin. Adams, PD; Bingman, C; Deng, K; Donohue, TJ; Gall, DL; Heins, RA; Helmich, KE; Holland, KC; McAndrew, RP; Noguera, DR; Pereira, JH; Phillips, GN; Ralph, J; Sale, KL; Simmons, BA, 2016)	2.09
"Lignin is an abundant biopolymer that has native interfacial functions but aggregates strongly in aqueous media. "	( Tunable Pickering emulsions with polymer-grafted lignin nanoparticles (PGLNs). Gupta, C; Silmore, KS; Washburn, NR, 2016)	2.13
"Lignin is a complex polyphenolic constituent of plant secondary cell walls. "	( Designer lignins: harnessing the plasticity of lignification. Boerjan, W; Mansfield, SD; Mottiar, Y; Ralph, J; Vanholme, R, 2016)	2.29
"Lignin is an important structural component of plant cell wall that confers mechanical strength and tolerance against biotic and abiotic stressors; however it affects the use of biomass such as wheat straw for some industrial applications such as biofuel production. "	( Lignin biosynthesis in wheat (Triticum aestivum L.): its response to waterlogging and association with hormonal levels. Ayele, BT; Jordan, MC; Levin, DB; Nguyen, TN; Son, S, 2016)	3.32
"Lignin is a complex polyphenyl aromatic compound which exists in tight associations with cellulose and hemicellulose to form plant primary and secondary cell wall. "	( Recent Developments in Using Advanced Sequencing Technologies for the Genomic Studies of Lignin and Cellulose Degrading Microorganisms. Kameshwar, AK; Qin, W, 2016)	2.1
"Lignin is a primary component of lignocellulosic biomass that is an underutilized feedstock in the growing biofuels industry. "	( Opportunities and challenges in biological lignin valorization. Beckham, GT; Johnson, CW; Karp, EM; Salvachúa, D; Vardon, DR, 2016)	2.14
"Lignin is a complex phenolic polymer that is deposited in the secondary cell wall of all vascular plants. "	( Lignification: Flexibility, Biosynthesis and Regulation. Zhao, Q, 2016)	1.88
"Lignin is an abundant aromatic plant cell wall polymer consisting of phenylpropanoid units in which the aromatic rings display various degrees of methoxylation. "	( Maize Tricin-Oligolignol Metabolites and Their Implications for Monocot Lignification. Boerjan, W; Carlos Del Río, J; Lan, W; Lu, F; Morreel, K; Ralph, J; Rencoret, J; Vermerris, W; Voorend, W, 2016)	1.88
"Lignin is an abundant biopolymer with a high carbon content and high aromaticity. "	( Paving the Way for Lignin Valorisation: Recent Advances in Bioengineering, Biorefining and Catalysis. Bruijnincx, PC; Clough, MT; Jastrzebski, R; Kennema, M; Ralph, J; Rinaldi, R; Weckhuysen, BM, 2016)	2.21
"Lignin is an attractive renewable feedstock for aromatic bulk and fine chemicals production, provided that suitable depolymerization procedures are developed. "	( Tandem Catalytic Depolymerization of Lignin by Water-Tolerant Lewis Acids and Rhodium Complexes. Bruijnincx, PC; Constant, S; Jastrzebski, R; Lancefield, CS; Weckhuysen, BM; Westwood, NJ, 2016)	2.15
"Lignin is a recalcitrant heteropolymer comprised of several complex stable bonds and linkages."	( Unleashing the potential of ligninolytic bacterial contributions towards pulp and paper industry: key challenges and new insights. Dasguptamandal, D; Kumar, A; Mandal, T; Priyadarshinee, R, 2016)	1.45
"Lignin is a major component of lignocellulosic biomass and as such, it is processed in enormous amounts in the pulp and paper industry worldwide. "	( Biological valorization of low molecular weight lignin. Abdelaziz, OY; Brink, DP; García-Hidalgo, J; Gorwa-Grauslund, MF; Hulteberg, CP; Lidén, G; Prothmann, J; Ravi, K; Sandahl, M; Sun, M; Turner, C, 2016)	2.13
"Lignin is a major polymer in the secondary plant cell wall and composed of hydrophobic interlinked hydroxyphenylpropanoid units. "	( Degradation of lignin β-aryl ether units in Arabidopsis thaliana expressing LigD, LigF and LigG from Sphingomonas paucimobilis SYK-6. Bjarnholt, N; Boerjan, W; Goeminne, G; Harholt, J; Jørgensen, B; Liu, S; Lu, F; Mnich, E; Motawie, MS; Møller, BL; Oyarce, P; Ralph, J; Ulvskov, P; Vanholme, R, 2017)	2.25
"Lignin is a phenolic heteropolymer that is deposited in secondary-thickened cell walls, where it provides mechanical strength. "	( Silencing CHALCONE SYNTHASE in Maize Impedes the Incorporation of Tricin into Lignin and Increases Lignin Content. Boerjan, W; Cesarino, I; Eloy, NB; Goeminne, G; Lan, W; Morreel, K; Nicomedes, J; Pallidis, A; Ralph, J; Saleme, ML; Smith, RA; Vanholme, R; Voorend, W, 2017)	2.13
"Lignin is a polyphenolic polymer specifically accumulating in the cell walls of xylem cells in higher vascular plants. "	( Analysis of Lignin Composition and Distribution Using Fluorescence Laser Confocal Microspectroscopy. Decou, R; Ménard, D; Pesquet, E; Serk, H, 2017)	2.28
"The lignin was found to be a good candidate for the liquefaction process, and biomass fractionation was necessary to maximize the yield of the liquid bio-fuel."	( Maximizing the liquid fuel yield in a biorefining process. Valentas, K; von Keitz, M; Zhang, B, 2008)	0.83
"Lignin is a complex polymer of hydroxylated and methoxylated phenylpropane units (monolignols) and lignification renders the cell wall more resistant to pathogen attack."	( Gene expression profiling and silencing reveal that monolignol biosynthesis plays a critical role in penetration defence in wheat against powdery mildew invasion. Bhuiyan, NH; King, J; Selvaraj, G; Wei, Y, 2009)	1.07
"Lignin is an abundant natural resource that is a potential source of valuable chemicals. "	( Computational study of bond dissociation enthalpies for lignin model compounds. Substituent effects in phenethyl phenyl ethers. Beste, A; Buchanan, AC, 2009)	2.04
"Lignin is a phenolic heteropolymer in secondary cell walls that plays a major role in the development of plants and their defense against pathogens. "	( The cinnamyl alcohol dehydrogenase gene family in Populus: phylogeny, organization, and expression. Bagniewska-Zadworna, A; Barakat, A; Carlson, JE; Choi, A; DiLoreto, DS; Plakkat, U; Yellanki, P, 2009)	1.8
"Lignin removal is a central issue in paper pulp manufacture, and production of other renewable chemicals, materials, and biofuels in future lignocellulose biorefineries. "	( Enzymatic delignification of plant cell wall: from nature to mill. Del Río, JC; Gutiérrez, A; Martínez, AT; Martínez, MJ; Ruiz-Dueñas, FJ, 2009)	1.8
"Lignin is a complex polymer derived from the oxidative coupling of three classical monolignols. "	( Engineering monolignol 4-O-methyltransferases to modulate lignin biosynthesis. Bhuiya, MW; Liu, CJ, 2010)	2.05
"Lignin is a key component in the biomass with a complex polymeric structure of the phenyl-C(3) alkyl units. "	( The pyrolytic degradation of wood-derived lignin from pulping process. Fang, MX; Gu, S; Luo, KH; Shen, DK; Wang, SR, 2010)	2.07
"Lignin is a polymer of phenylpropanoid compounds formed through a complex biosynthesis route, represented by a metabolic grid for which most of the genes involved have been sequenced in several plants, mainly in the model-plants Arabidopsis thaliana and Populus. "	( Abiotic and biotic stresses and changes in the lignin content and composition in plants. Bonine, CA; de Oliveira Fernandes Viana, J; Dornelas, MC; Mazzafera, P; Moura, JC, 2010)	2.06
"Lignin is a heteropolymer that is thought to form in the cell wall by combinatorial radical coupling of monolignols. "	( Modeling lignin polymerization. I. Simulation model of dehydrogenation polymers. Boerjan, W; Merks, RM; Morreel, K; Ralph, J; van Parijs, FR, 2010)	2.22
"Lignin is a main polymer component formed from three phenolic precursors containing none, one or two OMe groups, i.e."	( Theoretical and Raman spectroscopic studies of phenolic lignin model monomers. Barsberg, S; Larsen, KL, 2010)	1.33
"Lignin is a major component of plant secondary cell walls and is derived from p-hydroxyphenyl (H), guaiacyl (G), and syringyl (S) monolignols. "	( Syringyl lignin biosynthesis is directly regulated by a secondary cell wall master switch. Chen, F; Dixon, RA; Wang, H; Xu, Y; Yin, Y; Zhao, Q, 2010)	2.22
"Lignin engineering is a promising strategy to optimize lignocellulosic plant biomass for use as a renewable feedstock for agro-industrial applications. "	( Engineering traditional monolignols out of lignin by concomitant up-regulation of F5H1 and down-regulation of COMT in Arabidopsis. Akiyama, T; Boerjan, W; Christensen, JH; De Rycke, R; Kim, H; Lu, F; Morreel, K; Pazo, JR; Ralph, J; Rohde, A; Storme, V; Van Reusel, B; Vanholme, R, 2010)	2.07
"Lignin is a complex biopolymer derived primarily from the condensation of three monomeric precursors, the monolignols. "	( ATP-binding cassette-like transporters are involved in the transport of lignin precursors across plasma and vacuolar membranes. Liu, CJ; Miao, YC, 2010)	2.04
"Lignin is an aromatic heteropolymer and the second most abundant plant biopolymer after cellulose. "	( Transcriptional networks for lignin biosynthesis: more complex than we thought? Dixon, RA; Zhao, Q, 2011)	2.1
"Lignin is a main component of plant litter. "	( A new conceptual model for the fate of lignin in decomposing plant litter. Gatzek, C; Guggenberger, G; Kaiser, K; Kalbitz, K; Klotzbücher, T, 2011)	2.08
"Lignin is a main polymer formed from three phenolic presursors, containing none, one, or two OMe groups, i.e., H, G, and S units, respectively."	( Environmental effects on the lignin model monomer, vanillyl alcohol, studied by Raman spectroscopy. Barsberg, S; Larsen, KL, 2011)	1.38
"Lignin is a major component of certain plant cell walls. "	( Lignin variability in plant cell walls: contribution of new models. Neutelings, G, 2011)	3.25
"Lignin is a heterogeneous aromatic polymer found as 10-35% of lignocellulose, found in plant cell walls. "	( Pathways for degradation of lignin in bacteria and fungi. Ahmad, M; Bugg, TD; Hardiman, EM; Rahmanpour, R, 2011)	2.11
"Lignin is a major component of plant cell walls that is essential to their function. "	( Identification of grass-specific enzyme that acylates monolignols with p-coumarate. Kim, H; Lu, F; Ralph, J; Wilkerson, CG; Withers, S; Zhu, Y, 2012)	1.82
"Lignin is a complex phenolic plant cell wall polymer that is generated as a waste product from paper mills and biorefineries that process lignocellulosic biomass into fuels and chemicals."	( Template-mediated synthesis and bio-functionalization of flexible lignin-based nanotubes and nanowires. Caicedo, HM; Dempere, LA; Vermerris, W, 2012)	1.34
"Lignin is a component of lignocellulosic biomass and a promising matrix for recovering important renewable aromatic compounds. "	( Electro-catalytic oxidative cleavage of lignin in a protic ionic liquid. Hempelmann, R; Reichert, E; Volmer, DA; Wintringer, R, 2012)	2.09
"Lignin is an aromatic, hydrophobic and mildly branched polymer integrally associated with polysaccharides within the biomass, which negatively affects their extraction and hydrolysis during industrial processing."	( Biosynthesis and incorporation of side-chain-truncated lignin monomers to reduce lignin polymerization and enhance saccharification. Balzergue, S; Benke, PI; Cetinkol, OP; Chabout, S; Eudes, A; George, A; Holmes, BM; Keasling, JD; Kim, JS; Lapierre, C; Loqué, D; Mitra, P; Mouille, G; Mukerjee, P; Mukhopadhyay, A; Pollet, B; Ralph, J; Simmons, BA; Singh, S; Soubigou-Taconnat, L; Sun, L; Yang, F, 2012)	1.35
"Lignin is a complex, heterogeneous polymer in plant cell walls that provides mechanical strength to the plant stem and confers resistance to degrading microbes, enzymes, and chemicals. "	( Radical coupling reactions in lignin synthesis: a density functional theory study. Davis, M; Parks, JM; Sangha, AK; Smith, JC; Standaert, RF; Ziebell, A, 2012)	2.11
"Lignin is a polymer found in the cell wall of plants and is one of the main obstacles to the implementation of second-generation ethanol production because it confers the recalcitrance of the lignocellulosic material. "	( Analysis of soluble lignin in sugarcane by ultrahigh performance liquid chromatography-tandem mass spectrometry with a do-it-yourself oligomer database. Kiyota, E; Mazzafera, P; Sawaya, AC, 2012)	2.15
"Lignin engineering is an attractive strategy to improve lignocellulosic biomass quality for processing to biofuels and other bio-based products. "	( A systems biology view of responses to lignin biosynthesis perturbations in Arabidopsis. Boerjan, W; Christensen, JH; Goeminne, G; Halpin, C; Morreel, K; Rohde, A; Storme, V; Sundin, L; Vanholme, B; Vanholme, R, 2012)	2.09
"Lignin is an especially challenging substrate, but select microbes have evolved complex systems of enzymes for its breakdown through a radical-mediated oxidation process."	( Identification and characterization of a multifunctional dye peroxidase from a lignin-reactive bacterium. Barros, T; Brown, ME; Chang, MC, 2012)	1.33
"Lignin is a component of plant biomass that presents a significant obstacle to biofuel production. "	( Lignin-associated metagene expression in a lignocellulose-digesting termite. Buchman, GW; Kovaleva, ES; Scharf, ME; Sethi, A; Slack, JM, 2013)	3.28
"Lignin is a polymer in secondary cell walls of plants that is known to have negative impacts on forage digestibility, pulping efficiency, and sugar release from cellulosic biomass. "	( Functional analysis of metabolic channeling and regulation in lignin biosynthesis: a computational approach. Dixon, RA; Escamilla-Treviño, L; Lee, Y; Voit, EO, 2012)	2.06
"Lignin is a pollutant present in the mill process waters and such macromolecules can cause problems during biological treatment of process waters."	( Biodegradability enhancement by wet oxidation in alkaline media: delignification as a case study. Kallas, J; Verenich, S, 2002)	1.04
"Lignin is a major component of wood, the most widely used raw material for the production of pulp and paper. "	( Lignin: genetic engineering and impact on pulping. Baucher, M; Boerjan, W; Halpin, C; Petit-Conil, M, 2003)	3.2
"Lignin is an important and relatively recalcitrant structural biopolymer present in the majority of plant biomass."	( Identifying residues in natural organic matter through spectral prediction and pattern matching of 2D NMR datasets. Kelleher, B; Kingery, WL; Kvasha, M; Larin, N; Lefebvre, B; Moser, A; Simpson, AJ; Williams, A, 2004)	1.04
"Lignin is a highly branched polymer consisting of phenylpropane units, and it is one of the ingredients of the supporting matrix in plant cell walls. "	( Morphology of dry lignins and size and shape of dissolved kraft lignin particles by X-ray scattering. Gravitis, J; Hortling, B; Laine, J; Maximova, N; Serimaa, R; Simola, LK; Stenius, P; Vainio, U, 2004)	2.1
"Lignin is an aromatic heteropolymer, abundantly present in the walls of secondary thickened cells. "	( Profiling of oligolignols reveals monolignol coupling conditions in lignifying poplar xylem. Boerjan, W; Goeminne, G; Kim, H; Lu, F; Messens, E; Morreel, K; Ralph, J; Ralph, S, 2004)	1.77
"Lignin is a primary byproduct from the black liquor treatment in paper making industries, its application as micro-fertilizer in agricultural land might provide a promising alternative to sewage discharge. "	( Phyto-availability and speciation change of heavy metals in soils amended with lignin as micro-fertilizer. Mu, H; Shan, X; Wang, S; Zhang, S, 2005)	2
"Lignin is a major determinant of the decomposition of plant materials in soils. "	( Microbial community structure in soils with decomposing residues from plants with genetic modifications to lignin biosynthesis. Andreux, F; English, LC; Halpin, C; Hénault, C; Hopkins, DW, 2006)	1.99
"Lignin is a three-dimensional polymer with a high molecular weight, and it gives rigidity and mechanical resistance to the fibre and plant."	( Lignin deficiency in transgenic flax resulted in plants with improved mechanical properties. Oszmiański, J; Starzycki, M; Szopa, J; Wróbel-Kwiatkowska, M; Zebrowski, J, 2007)	2.5
"Lignin is an important component of secondarily thickened cell walls. "	( Molecular phenotyping of lignin-modified tobacco reveals associated changes in cell-wall metabolism, primary metabolism, stress metabolism and photorespiration. Boerjan, W; Boudet, AM; Dauwe, R; Gielen, B; Goeminne, G; Halpin, C; Kopka, J; Messens, E; Morreel, K; Ralph, J; Rochange, SF; Rohde, A; Van Beeumen, J, 2007)	2.09
"Lignin biosynthesis is a major carbon sink in gymnosperms and woody angiosperms. "	( Expression profiling of the lignin biosynthetic pathway in Norway spruce using EST sequencing and real-time RT-PCR. Alatalo, E; Fagerstedt, KV; Fossdal, CG; Kärkönen, A; Koutaniemi, S; Laakso, T; Paulin, L; Rudd, S; Saranpää, P; Simola, LK; Teeri, TH; Warinowski, T, 2007)	2.08
"Lignin is a durable aromatic network polymer that is second only to cellulose in natural abundance. "	( Lig-8, a highly bioactive lignophenol derivative from bamboo lignin, exhibits multifaceted neuroprotective activity. Akao, Y; Hara, H; Ito, Y; Nozawa, Y; Seki, N; Shimazawa, M, 2007)	2.02
"Lignin is an integral cell wall component of all vascular plants. "	( Purification and characterization of peroxidases correlated with lignification in poplar xylem. Bauw, G; Boerjan, W; Christensen, JH; Van Montagu, M; Welinder, KG, 1998)	1.74
"Lignin is a complex polymer formed by the oxidative polymerization of hydroxycinnamyl alcohol derivatives termed monolignols. "	( The biosynthesis of monolignols: a "metabolic grid", or independent pathways to guaiacyl and syringyl units? Chen, F; Dixon, RA; Guo, D; Parvathi, K, 2001)	1.75
"Lignin is a complex phenolic plant polymer that is essential for mechanical support, defense, and water transport in higher plants. "	( Transcriptional control of lignin biosynthesis by tobacco LIM protein. Ebinuma, H; Kawaoka, A, 2001)	2.05
"Lignin is a three-dimensionally branched aromatic polymer, composed of phenyl propane units, which is susceptible to bioconversion through the growth of the white rot fungus, Pluerotus ostreatus."	( Enzyme conversion of lignocellulosic plant materials for resource recovery in a Controlled Ecological Life Support System. Brewer, MA; Hendrickson, RL; Kohlmann, KL; Ladisch, MR; Sarikaya, A; Velayudhan, A; Weil, J; Westgate, P, 1996)	0.92
"Lignin is a major cellular component of higher plants. "	( Microgravity effects on plant growth and lignification. Cowles, JR; Jahns, G; Lemay, R, 1988)	1.72
"Lignin is a major byproduct in the biomass-to-ethanol process. "	( Production of oxychemicals from precipitated hardwood lignin. Lee, YY; Xiang, Q, 2001)	2
"Lignin is a heterogenous natural product composed of phenylpropane units and is usually associated with hemicellulose in its native state. "	( Stimulation of human peripheral blood polymorphonuclear cell iodination by lignin-related substances. Ichikawa, S; Inoue, Y; Kawazoe, Y; Kitajima, K; Konno, K; Oh-hara, T; Sakagami, H; Tanuma, S, 1991)	1.95
"Lignin is a key substrate which is extensively digested in goats fed on low-quality forage, with subsequent absorption of endproducts."	( Lignocellulose degradation and subsequent metabolism of lignin fermentation products by the desert black Bedouin goat fed on wheat straw as a single-component diet. Brosh, A; Silanikove, N, 1989)	1.24
"Lignin appeared to be an important component in the interaction with steroid hormones."	( In vitro binding of steroid hormones by natural and purified fibers. Howie, BJ; Shultz, TD, 1986)	0.99
"Lignin is a highly cross-linked complex polymer of phenylpropane units."	( Dietary fibre--definition, chemistry and analytical determination. Asp, NG, 1987)	0.99

Excerpt	Reference	Relevance
"Lignin has an immense potential for the production of lignin-based functional materials. "	( Multilamellar spherical micelles of alkali lignin: dissipative particle dynamics simulations. Li, Y; Shang, J; Wen, W; Yin, G; Zhu, G, 2023)	2.62
"Lignin has a complex structure built up from propylphenolic subunits; therefore, its valorization to value-added products (aromatics, phenolics, biogasoline, etc.) is highly desirable."	( Development of 'Lignin-First' Approaches for the Valorization of Lignocellulosic Biomass. Barta, K; Fridrich, B; Korányi, TI; Pineda, A, 2020)	1.63
"The lignin (LCMF) has a moderate level of mesoporosity before thermal treatment and a surface area of 63 m(2) g(-1) , which increases dramatically on pyrolysis at temperatures above 400 °C."	( Processed Lignin as a Byproduct of the Generation of 5-(Chloromethyl)furfural from Biomass: A Promising New Mesoporous Material. Budarin, VL; Clark, JH; Farmer, TJ; Henschen, J; Macquarrie, DJ; Mascal, M; Nagaraja, GK; Petchey, TH, 2015)	1.3
"Lignin has significant potential as an abundant and renewable source for commodity chemicals yet remains vastly underutilized. "	( A plant host, Nicotiana benthamiana, enables the production and study of fungal lignin-degrading enzymes. Deutsch, S; Khlystov, NA; Sattely, ES; Yoshikuni, Y, 2021)	2.29
"Lignin has been spotlighted as an abundant renewable bioresource for use in material technologies and applications such as biofuels, binders, composites, and nanomaterials for drug delivery. "	( pH-Dependent interaction mechanism of lignin nanofilms. Lee, DW; Lee, J; Lee, SY; Song, Y; Valtiner, M, 2021)	2.34
"Lignin has been recognized as a drop-in substitution to conventional aromatics, with its values gradually realized after tremendous research efforts in the recent five years."	( Recent advances of lignin valorization techniques toward sustainable aromatics and potential benchmarks to fossil refinery products. Guan, J; Ji, Y; Khan, RJ; Lam, CH; Lau, CY; Lee, DJ; Leu, SY; Wang, H; Xu, J; Zhao, J, 2022)	1.77
"Lignin has been used on its crude or modified forms for adsorption purposes. "	( Unraveling the adsorption mechanism of methylene blue onto selective pH precipitated Kraft lignins: Kinetic, equilibrium and thermodynamic aspects. Avelino, F; de Araújo, LFB; Lomonaco, D; Mazzetto, SE, 2022)	2.38
"Lignin has great potential as a natural, green, and sustainable broad-spectrum sunscreen active ingredient. "	( Revealing the relationship between molecular weight of lignin and its color, UV-protecting property. Li, K; Li, Y; Ragauskas, AJ; Song, X; Zhao, S, 2022)	2.41
"Lignin has many attractive features such as great biocompatibility, ultraviolet resistance, antioxidant property, and thermostability, making it a promising natural resource to be fabricated as functional structural color materials."	( Photonic Lignin with Tunable and Stimuli-Responsive Structural Color. Chen, W; Fang, Z; Liu, W; Qiu, X; Wang, J; Xiang, T; Yang, D, 2022)	1.86
"Lignin has been highlighted as a critical component for generating valuables, and its recovery prospects from solid and liquid PPI waste have been suggested."	( Challenges in developing strategies for the valorization of lignin-a major pollutant of the paper mill industry. Chanda, P; Majumdar, S; Mandal, DD; Singh, G, 2023)	1.87
"Lignin has an immense potential for the production of lignin-based functional materials. "	( Multilamellar spherical micelles of alkali lignin: dissipative particle dynamics simulations. Li, Y; Shang, J; Wen, W; Yin, G; Zhu, G, 2023)	2.62
"Lignin has valuable properties that make it a promising material for numerous applications, but it is far from being fully exploited."	( Opportunities and Challenges for Lignin Valorization in Food Packaging, Antimicrobial, and Agricultural Applications. Boarino, A; Klok, HA, 2023)	1.91
"Lignin has been suggested as a promising candidate for cosmetic applications due to its remarkable potential to absorb ultraviolet rays and distinctive antioxidant activity. "	( From sugarcane to skin: Lignin as a multifunctional ingredient for cosmetic application. Antunes, F; Costa, PS; Fangueiro, JF; Lopes, G; Mota, IF; Pintado, M, 2023)	2.66
"Lignin has the abilities to demonstrate broad-spectrum UV resistance and green antioxidant properties in advanced materials, taking advantage of its inherent chemical characteristics."	( Electrospray lignin nanoparticles as Pickering emulsions stabilizers with antioxidant activity, UV barrier properties and biological safety. He, D; Li, Q; Wang, X; Xin, H; Yu, M; Zhou, J; Zhu, C, 2023)	2
"Lignin has the potential to be used as an additive, coating agent, fertilizer, plant growth stimulator, and packaging material in the agroindustry due to its functional aromatic structure. "	( Current roles of lignin for the agroindustry: Applications, challenges, and opportunities. Ariyanta, HA; Aryana, N; Fatriasari, W; Kumar, A; Restu, WK; Sari, FP; Septiyanti, M; Sohail, A, 2023)	2.69
"Lignin has gained considerable interest owing to its attractive properties."	( Sustainable Biomass Lignin-Based Hydrogels: A Review on Properties, Formulation, and Biomedical Applications. Fatimi, A; Hachimi Alaoui, C; Réthoré, G; Weiss, P, 2023)	1.96
"Lignin has potential to serve as promising sunscreen agents as it has good ultraviolet (UV) absorption and antioxidant properties. "	( Construction of photo-responsive lignin as a broad-spectrum sunscreen agent. Chen, BK; Gao, J; Li, JH; Wu, Y, 2023)	2.63
"Lignin has emerged as a promising eco-friendly multifunctional ingredient for cosmetic applications, due to its ability to protect against ultraviolet radiation and its antioxidant and antimicrobial properties. "	( Sugarcane Light-Colored Lignin: A Renewable Resource for Sustainable Beauty. Antunes, F; Costa, CAE; Costa, PS; Fangueiro, JF; Mota, IF; Pintado, ME; Rodrigues, AE, 2023)	2.66
"Lignin has long been recognized as an important limiting factor for the polysaccharide-oriented biomass utilizations."	( Altered lignocellulose chemical structure and molecular assembly in CINNAMYL ALCOHOL DEHYDROGENASE-deficient rice. Koshiba, T; Kusumi, R; Lam, PY; Martin, AF; Matsumoto, N; Miyamoto, T; Sakamoto, M; Tobimatsu, Y; Umezawa, T; Yamamura, M, 2019)	1.24
"Lignin has been studied extensively by a range of different techniques, including anatomical and morphological analyses using dyes to characterize the polymer localization in situ."	( A rapid and quantitative safranin-based fluorescent microscopy method to evaluate cell wall lignification. Baldacci-Cresp, F; Baucher, M; Blervacq, AS; Hawkins, S; Neutelings, G; Spriet, C; Twyffels, L, 2020)	1.28
"Lignin has been considered as a crucial recalcitrance component in biomass utilization."	( The critical role of lignin in lignocellulosic biomass conversion and recent pretreatment strategies: A comprehensive review. Meng, X; Pu, Y; Ragauskas, AJ; Yoo, CG, 2020)	1.6
"Lignin valorization has been scarcely considered in the form of liquid crystalline polymer blends. "	( Lignin-Assisted Stabilization of an Oriented Liquid Crystalline Cellulosic Mesophase, Part B: Toward the Molecular Origin and Mechanism. Chen, Y; Friedrich, C; Gleuwitz, FR; Laborie, MG; Sivasankarapillai, G, 2020)	3.44
"Lignin has a complex structure built up from propylphenolic subunits; therefore, its valorization to value-added products (aromatics, phenolics, biogasoline, etc.) is highly desirable."	( Development of 'Lignin-First' Approaches for the Valorization of Lignocellulosic Biomass. Barta, K; Fridrich, B; Korányi, TI; Pineda, A, 2020)	1.63
"Lignin has enabled plants to colonize land, grow tall, transport water within their bodies, and protect themselves against various stresses. "	( High-order mutants reveal an essential requirement for peroxidases but not laccases in Casparian strip lignification. De Bellis, D; Emonet, A; Fujita, S; Geldner, N; Hématy, K; Lee, Y; Rojas-Murcia, N; Ursache, R, 2020)	2
"Lignin also has non-biomedical applications including dispersing agents, surfactants, detergent/ cleaning agents, energy storage, etc."	( Recent Advancements in Lignin Valorization and Biomedical Applications: A Patent Review. Ekielski, A; Mishra, PK; Prasad, V; Siddiqui, L; Talegaonkar, S, 2022)	1.75
"Lignin has been demonstrated to be green and effective for the modification of ZnO-based materials. "	( Fabrication of litchi-like lignin/zinc oxide composites with enhanced antibacterial activity and their application in polyurethane films. Li, Q; Li, Z; Liu, Y; Qiu, X; Wang, H; Wang, Y; Yan, M; Yang, D, 2021)	2.36
"Lignin has functional properties, such as antioxidant activity, that make it a potential natural active ingredient for health-care products."	( Safety aspects of kraft lignin fractions: Discussions on the in chemico antioxidant activity and the induction of oxidative stress on a cell-based in vitro model. Avelino, F; Cestari, MM; Gagosian, VSC; Leme, DM; Lomonaco, D; Magalhães, WLE; Matos, M; Rodrigues-Souza, I; Thá, EL, 2021)	1.65
"Lignin research has historically focused on lignin degradation techniques in the hope of converting lignin into useful aromatic carbon feedstocks."	( The study of the chromatographic behavior and a mass spectrometric approach to differentiating the diastereomer pair of the β-O-4 lignin dimer series. Asare, SO; Dean, KR; Lynn, BC, 2021)	1.55
"Lignin has been shown to contribute to stem mechanical strength."	( Genetic and transcriptomic analyses of lignin- and lodging-related traits in Brassica napus. Duan, X; Jian, H; Li, J; Li, W; Liu, L; Lu, K; Paterson, AH; Wang, J; Wang, R; Wei, L; Xu, X; Yin, N, 2017)	1.45
"Lignin engineering has been a useful tool to increase the knowledge on the mechanical function of lignin as it allows for modifications of lignin content and composition and the subsequent studying of the mechanical properties of these transgenics."	( The effect of altered lignin composition on mechanical properties of CINNAMYL ALCOHOL DEHYDROGENASE (CAD) deficient poplars. Boerjan, W; Burgert, I; Déjardin, A; Gierlinger, N; Özparpucu, M; Pilate, G; Rüggeberg, M; Van Acker, R; Vanholme, R, 2018)	1.52
"Lignin availability has increased significantly due to the commercialization of several processes for recovery and further development of alternatives for integration into Kraft pulp mills. "	( Quantification and Variability Analysis of Lignin Optical Properties for Colour-Dependent Industrial Applications. Ajao, O; Benali, M; Boumghar, Y; El Mehdi, N; Jeaidi, J; Restrepo, AM, 2018)	2.19
"Lignin valorization has gained increasing attention over the past decade. "	( Perspective on Lignin Oxidation: Advances, Challenges, and Future Directions. Renders, T; Schutyser, W; Sels, BF; Vangeel, T, 2018)	2.28
"Lignin modification has positive impacts on forage management."	( Development and commercialization of reduced lignin alfalfa. Barros, J; Dixon, RA; Temple, S, 2019)	1.49
"Lignin research has long been motivated by the outstanding importance of wood for human societies. "	( The Casparian strip-one ring to bring cell biology to lignification? Barbosa, ICR; Geldner, N; Rojas-Murcia, N, 2019)	1.96
"Lignin has been associated to the resistance for pest, disease and lodging."	( RcPAL, a key gene in lignin biosynthesis in Ricinus communis L. Chen, S; He, X; Li, W; Lu, J; Shi, Y; Wang, Y; Yin, X, 2019)	1.55
"Lignin has been recognized as a major recalcitrant factor negatively affecting the processing of plant biomass into bioproducts."	( The lignin toolbox of the model grass Setaria viridis. Carvalho, GG; Cesarino, I; de Lima, LGA; Ferreira, SS; Simões, MS; Svartman, RMA, 2019)	1.79
"Lignin derivatives have been shown to have several bioactive functions."	( Lignin Induces ES Cells to Differentiate into Neuroectodermal Cells through Mediation of the Wnt Signaling Pathway. Akamatsu, H; Date, Y; Hasegawa, S; Inoue, Y; Mizutani, H; Nakata, S; Yamada, T, 2013)	2.55
"Lignin has been extracted and purified for five types of Iraqi date palm using Klason lignin method."	( Characterization and determination of lignin in different types of Iraqi phoenix date palm pruning woods. Abdul Latif, MH; Abdullah, HM; Attiya, HG, 2013)	1.38
"Lignin modification has been a breeding target for the improvements of forage digestibility and energy yields in forage and bioenergy crops, but decreased lignin levels are often accompanied by reduced lodging resistance. "	( Increased lodging resistance in long-culm, low-lignin gh2 rice for improved feed and bioenergy production. Ebitani, T; Funada, R; Hirasawa, T; Inoue, K; Kanekatsu, M; Kato, H; Matsuoka, M; Motobayashi, T; Nakaba, S; Ookawa, T; Sugiyama, C; Takarada, T; Tojo, S; Toyota, K; Ueda, T; Vazirzanjani, M; Yamamoto, T; Yokoyama, T, 2014)	2.1
"Lignin has proven to be highly effective "green" multi-functional binding, complexing and reducing agents for silver cations as well as capping agents for the synthesis of silver nanoparticles on ultra-fine cellulose fibrous membranes. "	( Synthesis of surface bound silver nanoparticles on cellulose fibers using lignin as multi-functional agent. Hsieh, YL; Hu, S, 2015)	2.09
"The lignin (LCMF) has a moderate level of mesoporosity before thermal treatment and a surface area of 63 m(2) g(-1) , which increases dramatically on pyrolysis at temperatures above 400 °C."	( Processed Lignin as a Byproduct of the Generation of 5-(Chloromethyl)furfural from Biomass: A Promising New Mesoporous Material. Budarin, VL; Clark, JH; Farmer, TJ; Henschen, J; Macquarrie, DJ; Mascal, M; Nagaraja, GK; Petchey, TH, 2015)	1.3
"Lignin monophenols have been measured in the cupric oxide oxidation products from lichens of different systematic groups. "	( Lignin phenols derivatives in lichens. Belyaev, NA; Peresypkin, VI; Romankevich, EA; Ulyantzev, AS; Zavarzin, AA; Zavarzina, AG, 2015)	3.3
"Lignin has been used mostly as an energy source during paper production; however, recent interest in replacing fossil fuels with renewable resources has highlighted its potential value in providing aromatic chemicals."	( Discovery of 12-mer peptides that bind to wood lignin. Isozaki, K; Nakamura, M; Takaya, H; Watanabe, T; Yamaguchi, A, 2016)	1.41
"The lignin obtained has been characterized by FTIR (Fourier transform infrared), GPC (Gel permeation chromatography), and (1)H NMR (Nuclear magnetic resonance)."	( Isolation and characterization of wheat straw lignin with a formic acid process. Deng, H; Lin, L; Liu, S; Pan, C; Sun, Y; Zhang, J, 2010)	1.1
"Lignin has affinity with metal ions in the following order: Pb(II)>Cu(II)>Cd(II)>Zn(II)>Ni(II)."	( Adsorption of metal ions on lignin. Guo, X; Shan, XQ; Zhang, S, 2008)	1.36
"Lignin has been isolated by a modified mild acidolysis method and thoroughly characterized by functional group analysis, by a series of degradation techniques (nitrobenzene oxidation, permanganate oxidation, thioacidolysis, and Py-GC-MS), and (1)H and (13)C NMR spectroscopy."	( Comprehensive study on the chemical structure of dioxane lignin from plantation Eucalyptus globulus wood. Amado, FM; Domingues, PM; Evtuguin, DV; Faix, O; Neto, CP; Robert, D; Silva, AM, 2001)	1.28
"Lignin has no effect on bile acid metabolism."	( In vivo studies with fibre components. Fisher, A; Hillman, LC; Peters, S; Pomare, EW, 1987)	0.99

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"The lignin content may increase briquettes compressive strength produced in high temperatures."	( Briquettes of acai seeds: characterization of the biomass and influence of the parameters of production temperature and pressure in the physical-mechanical and energy quality. de Oliveira, PRS; de Oliveira, TJP; Trugilho, PF, 2022)	1.2
"Lignin plays a critical role in the cell wall extensibility and root elongation under stressed conditions."	( Boron-mediated lignin metabolism in response to aluminum toxicity in citrus (Poncirus trifoliata (L.) Raf.) root. Cheng, J; Jiang, C; Li, S; Yan, L; Zhang, Y, 2022)	1.8
"Lignin plays a central role in plant defense and its metabolism is regulated by light wavelength composition (light quality)."	( Enhanced lignin synthesis and ecotypic variation in defense-related gene expression in response to shade in Norway spruce. García-Gil, MR; Gorzsás, A; Ranade, SS; Seipel, G, 2022)	1.86
"Lignin could inhibit iron oxide dissolution and stabilize the combination of Cd/Pb and iron oxides in soil."	( Remediation of cadmium and lead contaminated soils using Fe-OM based materials. Chen, Z; Lin, Q; Liu, Q; Luo, J; Tang, J, 2022)	1.44
"Lignin displays a highly challenging renewable. "	( Systems metabolic engineering upgrades Corynebacterium glutamicum to high-efficiency cis, cis-muconic acid production from lignin-based aromatics. Barton, N; Becker, J; Kohlstedt, M; Weiland, F; Wittmann, C, 2023)	2.56
"Lignin plays a crucial role in cell wall structural integrity, stem strength, water transport, mechanical support and plant resistance to pathogens."	( A Joint Transcriptomic and Metabolomic Analysis Reveals the Regulation of Shading on Lignin Biosynthesis in Asparagus. He, M; Li, M; Li, X; Li, Y; Lu, W; Ma, J; Sun, B; Zheng, Y, 2023)	1.86
"Lignin removal plays a crucial role in the efficient bioconversion of lignocellulose to fermentable sugars. "	( Follow-up of solid-state fungal wood pretreatment by a novel near-infrared spectroscopy-based lignin calibration model. Broos, W; Cornet, I; Gergely, S; Slezsák, J; Vlaeminck, SE; Wittner, N, 2023)	2.57
"The lignin plays one of the most important roles in plant secondary metabolism. "	( CRISPR/Cas9 mutated p-coumaroyl shikimate 3'-hydroxylase 3 gene in Populus tomentosa reveals lignin functioning on supporting tree upright. Hui, W; Li, H; Li, Q; Liu, N; Lu, F; Wang, B; Wang, Z; Wu, AM; Yang, L; Yue, F; Zeng, Q; Zhang, K; Zhang, S; Zhang, W, 2023)	1.69
"Lignin displays attractive properties in peripheral nerve applications. "	( Application of electrospun polycaprolactone fibers embedding lignin nanoparticle for peripheral nerve regeneration: In vitro and in vivo study. Amini, S; Amirpour, N; Jahromi, M; Kazemi, M; Najafabadi, SS; Rafienia, M; Salehi, H; Saudi, A, 2020)	2.24
"Lignin plays an important role in plant growth and development, protects from biotic and abiotic stresses, and in the quality of animal fodder, the wood, and industrial lignin products."	( Estimation of Plant Biomass Lignin Content using Thioglycolic Acid (TGA). Dampanaboina, L; Mendu, V; Yuan, N, 2021)	1.64
"The lignin contents allow a greater thermal stability (<330°C) than the same size CNF (<250°C)."	( A comparative study of the suitability of different cereal straws for lignocellulose nanofibers isolation. Domínguez-Robles, J; Espinosa, E; Otero, R; Rodríguez, A; Sánchez, R, 2017)	0.94
"Lignin is the main cause of lignocellulosic biomass recalcitrance to industrial enzymatic hydrolysis. "	( Introducing curcumin biosynthesis in Arabidopsis enhances lignocellulosic biomass processing. Boerjan, W; De Meester, B; De Rycke, R; de Vries, L; Fonseca, F; Goeminne, G; Li, Y; Oyarce, P; Pallidis, A; Ralph, J; Sels, B; Tsuji, Y; Van den Bosch, S; Vanholme, R, 2019)	1.96
"Lignin plays important structural and functional roles in plants by forming a hydrophobic matrix in secondary cell walls that enhances mechanical strength and resists microbial decay. "	( A versatile click-compatible monolignol probe to study lignin deposition in plant cell walls. Anderson, CT; Chen, G; Diehl, BG; Pandey, JL; Richard, TL; Wang, B, 2015)	2.11
"Lignin plays an important role in plant structural support and water transport, and is considered one of the hallmarks of land plants. "	( Ancient origin of the biosynthesis of lignin precursors. Boucher, Y; Case, RJ; Labeeuw, L; Martone, PT, 2015)	2.13
"Lignin plays a vital role in plant adaptation to terrestrial environments. "	( Evolution of the Cinnamyl/Sinapyl Alcohol Dehydrogenase (CAD/SAD) gene family: the emergence of real lignin is associated with the origin of Bona Fide CAD. Guo, DM; Ran, JH; Wang, XQ, 2010)	2.02
"Lignin was 23% lower (P less than or equal to .01) and in vitro DM digestibility (IVDMD) was 4% higher (P less than or equal to .01) in BMR vs normal genotype forages."	( Digestibility and feeding value of pearl millet as influenced by the brown-midrib, low-lignin trait. Cherney, DJ; Johnson, KD; Patterson, JA, 1990)	1.22

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"Lignin was treated by mechanical activation (MA) in a customized stirring ball mill, and the structure and reactivity in further esterification were studied. "	( Effect of mechanical activation on structure changes and reactivity in further chemical modification of lignin. Chen, D; Feng, Z; Hu, H; Huang, A; Huang, K; Huang, Z; Qin, X; Yang, M; Zhang, Y; Zhao, X, 2016)	2.09
"Lignin in pretreated cellulosic biomass can non-productively adsorb cellulase, resulting in loss of a significant portion of this expensive protein. "	( Impact of surfactants on pretreatment of corn stover. Qing, Q; Wyman, CE; Yang, B, 2010)	1.8
"Lignin in the pretreatment liquor was precipitated and subjected to TGA and FTIR analyses."	( Investigation of biomass degradation mechanism in pretreatment of switchgrass by aqueous ammonia and sodium hydroxide. Gupta, R; Lee, YY, 2010)	1.08
"Lignins (native and treated) showed nonlinear sorption for all compounds studied, emphasizing their glassy character."	( Sorption of organic contaminants by biopolymers: role of polarity, structure and domain spatial arrangement. Cook, R; Tao, S; Wang, X; Xing, B, 2007)	1.06
"Lignin was treated with the iron-binding chelator and the changes in structure were investigated by 1H-NMR, 13C-NMR, difference spectrum caused by ionization under alkaline conditions and nitrobenzene oxidation."	( Function of the iron-binding chelator produced by Coriolus versicolor in lignin biodegradation. Chen, J; Gao, P; Huang, F; Wang, L; Yan, W, 2008)	1.3
"The treated lignin samples were used as additives, which not only improved the mechanical properties of PLA on the basis of retaining its thermal stability, but also granted excellent antimicrobial and biocompatibility properties."	( Utilization of lignin upon successive fractionation and esterification in polylactic acid (PLA)/lignin biocomposite. Li, C; Wang, Q; Yan, Y; Zhai, S; Zhang, L; Zhang, X; Zhao, X, 2022)	1.43
"The treated lignins are characterized by polysaccharide content, molecular weight, hydroxyl content, and Attenuated Total Reflection-Fourier Transform Infrared Spectroscopy (ATR-FTIR)."	( Strategies for the Removal of Polysaccharides from Biorefinery Lignins: Process Optimization and Techno Economic Evaluation. Corderi, S; De Roo, T; Elst, K; Renders, T; Servaes, K; Vanbroekhoven, K, 2021)	1.22
"ostreatus ligninolytic capacity under conditions mimicking its natural habitat."	( Inactivation of a Pleurotus ostreatus versatile peroxidase-encoding gene (mnp2) results in reduced lignin degradation. Hadar, Y; Knop, D; Levinson, D; Mabjeesh, SJ; Salame, TM; Yarden, O, 2014)	1
"The treated lignins are the purified Kraft lignin and the alkaline hydrolyzed Kraft lignin."	( Feasibility of incorporating treated lignins in fiberboards made from agricultural waste. El Mansouri, NE; Francesc, F; Mancera, C; Pelach, MA; Salvadó, J, 2012)	1.01

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" Comparison of HPLC profiles of the hydrolysates from both toxic and nontoxic fractions did not reveal differences between the phenolic acids released."	( Involvement of ligninlike compounds in toxicity of dietary alder leaf litter against mosquito larvae. David, JP; Marigo, G; Meyran, JC; Rey, D, 2001)	0.66
"To characterize the toxic compounds involved in the dietary toxicity of decomposed arborescent leaf litter against larval mosquito, a toxic fraction was extracted from crude leaf litter by using hot water."	( Dietary toxicity of decomposed arborescent leaf litter against larval mosquito: involvement of a lignin-polypeptidic complex. Marigo, G; Meyran, JC; Tilquin, M, 2002)	0.53
" The wastewater is purified by secondary treatment (mechanical, chemical and biological) which removes most of the toxic substances from the discharge."	( Multivariate statistics of the pyrolysis products of high molecular components in pulping wastewaters to explain their toxicity. Herve, S; Knuutinen, J; Kukkola, J; Paasivirta, J; Pessala, P; Schultz, E, 2005)	0.33
" Toxicity of lignin biodegradation liquors started to decrease in the beginning of the test, but became more toxic towards the end of the test again."	( Evaluation of biodegradation of nonylphenol ethoxylate and lignin by combining toxicity assessment and chemical characterization. Ahkola, H; Ahtiainen, J; Herve, S; Karhu, M; Keränen, J; Knuutinen, J; Nakari, T; Paasivirta, J; Pessala, P; Schultz, E, 2009)	0.97
"Effluents originated in cellulose pulp manufacturing processes are usually toxic and recalcitrant, specially the bleaching effluents, which exhibit high contents of aromatic compounds (e."	( Toxicity and recalcitrant compound removal from bleaching pulp plant effluents by an integrated system: anaerobic packed-bed bioreactor and ozone. Botta, CM; Chaparro, TR; Pires, EC, 2010)	0.36
" Thus, lignin stabilized silver nanoparticles based optical sensor for H2O2 could be potentially applied in the determination of reactive oxygen species and toxic chemicals which further expands the importance of lignin stabilized silver nanoparticles."	( Hydrogen peroxide sensing and cytotoxicity activity of Acacia lignin stabilized silver nanoparticles. Aadil, KR; Barapatre, A; Jha, H; Meena, AS, 2016)	1.13
" Lemna minor, a model duckweed species, can grow well in high NH4 (+) environment but to some extent can also suffer toxic effects."	( Transcriptomic and physiological analysis of common duckweed Lemna minor responses to NH4(+) toxicity. Li, R; Tang, X; Wang, W; Zhao, Q; Zhu, Q, 2016)	0.43
" Reactive oxygen species (ROS) and cell death were studied using stained fronds under toxic levels of NH4 (+)."	( Transcriptomic and physiological analysis of common duckweed Lemna minor responses to NH4(+) toxicity. Li, R; Tang, X; Wang, W; Zhao, Q; Zhu, Q, 2016)	0.43
" However, no inactivated and/or subunit mucosal vaccine has been approved for human use, largely because of the lack of a safe and effective mucosal adjuvant."	( Polymeric Caffeic Acid Is a Safer Mucosal Adjuvant That Augments Antigen-Specific Mucosal and Systemic Immune Responses in Mice. Aramaki, Y; Kiyono, H; Kunisawa, J; Ogasawara, M; Ohno, N; Saito, M; Tada, R; Yamanaka, D, 2018)	0.48
"The safe disposal of pulp and paper mill effluent is still a threat to the environment due to the presence of several unknown organic pollutants."	( Detection and assessment of the phytotoxicity of residual organic pollutants in sediment contaminated with pulp and paper mill effluent. Chandra, R; Yadav, S, 2018)	0.48
" Replacement of media post centrifugation resulted in minimal exposure of cells to excess polymers, which were toxic to cells."	( Enhanced transfection of a macromolecular lignin-based DNA complex with low cellular toxicity. Deen, GR; Ho, YK; Kai, D; Loh, XJ; Too, HP; Tu, GXE, 2018)	0.75
" In vitro cytotoxicity studies revealed that BLNPs were significantly toxic (74."	( Assessing the potential of lignin nanoparticles as drug carrier: Synthesis, cytotoxicity and genotoxicity studies. Bag, J; Ekielski, A; Iqbal, Z; Leekha, A; Mishra, H; Mishra, M; Mishra, PK; Mittal, D; Siddiqui, L; Talegaonkar, S; Verma, AK, 2020)	0.86
" However, their potential toxic impact and mechanisms on plant growth are still unclear."	( Phytotoxicity Assessment of Copper Oxide Nanoparticles on the Germination, Early Seedling Growth, and Physiological Responses in Oryza sativa L. He, J; Liu, J; Ren, Y; Wang, W; Xue, Y; Zhang, L, 2020)	0.56
" These results showed that LPs at different scales (nano and micro) present biological properties and are safe to be used in different high value industrial sectors, such as biomedical, pharmaceutical and food."	( Green synthesis of lignin nano- and micro-particles: Physicochemical characterization, bioactive properties and cytotoxicity assessment. Azinheiro, S; Cerqueira, MA; Freitas, FMC; Garrido-Maestu, A; Gonçalves, C; Michelin, M; Pastrana, LM; Teixeira, JA; Vicente, AA, 2020)	0.89
" cerevisiae through a variety of toxic molecular mechanisms, predominantly via damaging macromolecules and hampering the production of targeted compounds."	( In-depth understanding of molecular mechanisms of aldehyde toxicity to engineer robust Saccharomyces cerevisiae. Jayakody, LN; Jin, YS, 2021)	0.62
" The Egyptian standard limits for safe industrial effluents discharge into marine environment with a concomitant decrease in scale formation precursors were achieved recommending its safe reuse for enhanced oil recovery."	( Sustainable ecofriendly recruitment of bioethanol fermentation lignocellulosic spent waste biomass for the safe reuse and discharge of petroleum production produced water via biosorption and solid biofuel production. El-Azab, WIM; El-Gendy, NS; Nassar, HN, 2022)	0.72
" Here, we investigated the behavior and toxic effects of two layered double hydroxides (LDHs) nanomaterials with different metallic constituents (Mg-Al-LDH and Zn-Al-LDH) at relatively low exposure concentrations on a freshwater green alga (Chlorella pyrenoidosa) in the absence and presence of two types of NOM, namely dissolved organic matter (DOM) and dealkaline lignin (DL)."	( Dissolved Organic Matter and Lignin Modulate Aquatic Toxicity and Oxidative Stress Response Activated by Layered Double Hydroxides Nanomaterials. Wang, DG; Wang, Z; Yu, L, 2023)	1.37
" This critical review aims to shed light on the potential adverse effects of refractory pollutants from PPMW on natural ecosystems and living organisms."	( A critical review on environmental risk and toxic hazards of refractory pollutants discharged in chlorolignin waste of pulp and paper mills and their remediation approaches for environmental safety. Kumar, V; Verma, P, 2023)	1.13

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" To better understand its pharmacological activities, we need to determine its pharmacokinetic profiles."	( Study on pharmacokinetics of 3,4-divanillyltetrahydrofuran in rats by ultra-fast liquid chromatography/tandem mass spectrometry. Chai, C; Cui, XB; Shan, CX; Sun, X; Wang, XZ; Wen, HM; Yu, S, 2016)	0.43

Excerpt	Reference	Relevance
" ESR spectroscopy might be applicable for the detection of drug-drug interaction."	( [Detection of drug-drug interaction by ESR spectroscopy]. Sakagami, H; Satoh, K, 1999)	0.3
" The new Py-GC method combined with sample preacetylation allowed us an accurate quantitative analysis of detailed lignin monomer composition using a microgram order of extractive-free plant samples."	( Quantitative analysis of detailed lignin monomer composition by pyrolysis-gas chromatography combined with preliminary acetylation of the samples. Ishida, Y; Ohtani, H; Ona, T; Sonoda, T; Tsuge, S; Yokoi, H, 2001)	0.8
"A novel conversion process using steam explosion combined with enzymatic digestibility was exploited to increase sugar yield."	( Xylose production from corn stover biomass by steam explosion combined with enzymatic digestibility. Chen, HZ; Liu, ZH, 2015)	0.42
"In this experiment, corn stover was treated with optimal combined pretreatment conditions: 2% NaOH at 80 °C treated 2 h combined with initial pH 9 at the ozone concentration of 78 mg/mL treated 25 min."	( Evaluation of the Effects of Isolated Lignin on Cellulose Enzymatic Hydrolysis of Corn Stover Pretreatment by NaOH Combined with Ozone. Fang, S; Liu, P; Tong, S; Wang, W; Zhang, C, 2018)	0.75
"The effects of liquid hot water combined with 1, 4-butanediol (LHW-BDO) on the chemical composition and structure of moso bamboo were investigated."	( Effects of Liquid Hot Water Combined with 1, 4-Butanediol on Chemical Composition and Structure of Moso Bamboo. Jiang, JC; Wei, M; Xie, JC; Xu, H; Yang, J; Zhang, N; Zhao, J, 2020)	0.56
"The goal of this work was to explore the effect of Fenton pretreatment combined with bacteria inoculation on the formation of humic substances (HS) during rice straw composting."	( Effect of Fenton pretreatment combined with bacteria inoculation on humic substances formation during lignocellulosic biomass composting derived from rice straw. Jia, L; Li, P; Liu, L; Mohamed, TA; Qu, F; Wei, Z; Wu, D; Zhao, R; Zhao, Y; Zhu, L, 2020)	0.56
"Highly acidic lignin-derived sulfonated carbons (LDSCs) were produced from hardwood and softwood kraft lignins under mild conditions by applying fractionation and/or pre-carbonization treatments combined with acid-assisted hydrothermal carbonization."	( Rational production of highly acidic sulfonated carbons from kraft lignins employing a fractionation process combined with acid-assisted hydrothermal carbonization. Carvalho, WA; Mandelli, D; Nunes, RS; Tudino, TC; Vieira, LM, 2020)	1.15
"In order to minimize waste liquor, save resources, and reduce costs, the effects of alkali recycling and ozone recycling on enzymatic conversion in alkali combined with ozone pretreatment of corn stover and the mechanism were studied."	( Effects and Mechanisms of Alkali Recycling and Ozone Recycling on Enzymatic Conversion in Alkali Combined with Ozone Pretreatment of Corn Stover. Li, F; Li, Y; Liu, P; Zhang, J; Zhao, Z, 2021)	0.62
" In the current study, fourier transform ion cyclotron mass spectrometry (FT-ICR-MS) combined with fluorescent spectroscopy was used to assess the molecular composition and driving mechanism of DOM in 22 plateau lakes in Mongolia Plateau Lakes Region (MLR), Qinghai Plateau Lakes Region (QLR) and Tibet Plateau Lakes Region (TLR) of China."	( FT-ICR-MS combined with fluorescent spectroscopy reveals the driving mechanism of the spatial variation in molecular composition of DOM in 22 plateau lakes. Li, D; Li, M; Liu, S; Pan, B; Wang, Y, 2023)	0.91

Excerpt	Reference	Relevance
" These data indicate that the bioavailability of silybin is much greater after administration of silipide than after administration of silymarin."	( Pharmacokinetics of silybin in bile following administration of silipide and silymarin in cholecystectomy patients. Gatti, G; Perucca, E; Schandalik, R, 1992)	0.28
" A Western-type diet elevates plasma levels of sex hormones and decreases the sex hormone binding globulin concentration, increasing the bioavailability of these steroids."	( Western diet and Western diseases: some hormonal and biochemical mechanisms and associations. Adlercreutz, H, 1990)	0.28
" These reactions among fiber, inorganic iron, and other constituents of food may influence the bioavailability of dietary iron and the simple systems described here offer a means of dissecting interactions that are complex in vivo."	( Components of fiber bind iron in vitro. Fernandez, R; Phillips, SF, 1982)	0.26
"Low bioavailability of folacin has been previously reported for a variety of foods of plant origin."	( Effects of dietary fiber on the bioavailability of folic acid monoglutamate. Damron, BL; Gregory, JF; Ristow, KA, 1982)	0.26
" By assessing the type of bonding involved between pesticide and plants or soil, some assessment of the bioavailability of these bound residues to the environment can be made."	( Incorporation of foreign compound metabolites into plant and soil constituents. Adler, IR; Boka, G; Honeycutt, RC; Secrest, WL; Simoneaux, BJ; Sumner, DD, )	0.13
"Experiments were conducted to determine effects of isolated lignin and intact lignin in foods on bioavailability of intrinsic iron in lignin-containing foods and of supplemental iron (FeSO4."	( Iron bioavailability from diets containing isolated or intact sources of lignin. Czarnecki-Maulden, GL; Fahey, GC; Fly, AD, )	0.61
" Relationships between dietary fibre, ALN, MC, bioavailability of dietary minerals and risk of colorectal cancer are discussed."	( Dietary fibre on cell proliferation in large bowel mucosal crypts near or away from lymphoid nodules and on mineral bioavailability. Cameron, IL; Carter, JW; Hardman, WE; Heitman, DW, 2000)	0.31
" The fungi analysed may facilitate the composting of lignocellulosic wastes by means of an increase in substrate bioavailability and OM humification."	( The effect of aeration on the biotransformation of lignocellulosic wastes by white-rot fungi. Elorrieta, MA; López, MJ; Moreno, J; Suárez-Estrella, F; Vargas-García, MC, 2002)	0.31
" More research is warranted to determine the bioavailability of lignins in the human diet."	( Dietary lignins are precursors of mammalian lignans in rats. Adlercreutz, H; Begum, AN; Fukushima, K; Heinonen, SM; Lapierre, C; Mila, I; Nagano, K; Nicolle, C; Rémésy, C; Scalbert, A, 2004)	1
" Sorption to such lignocellulosic materials may limit the bioavailability of organic contaminants in landfills."	( Effect of cellulose/hemicellulose and lignin on the bioavailability of toluene sorbed to waste paper. Barlaz, MA; Chen, Y; Knappe, DR, 2004)	0.59
" LPs also decreased oleate-induced microsomal triglyceride transfer protein (MTTP) mRNA expression and cellular total cholesterol, suggesting that lipid bioavailability and lipidation of lipoprotein are likely involved in the decreased secretion of apo-B."	( Lignophenols decrease oleate-induced apolipoprotein-B secretion in HepG2 cells. Fujita, S; Funaoka, M; Mikame, K; Mukai, Y; Norikura, T; Sato, S, 2010)	0.36
" These findings indicate that organic materials especially wood sawdust may be used as bulking agents to reduce the mobility and bioavailability of toxic metals in solid waste composts."	( Increase in complexation ability of humic acids with the addition of ligneous bulking agents during sewage sludge composting. Feng-Song, Z; Ming, Y; Wei, L; Xiong, X; Yan-Xia, L, 2010)	0.36
" In this work, we aimed at enhancing the secretion of lignin-modifying oxidoreductases in Trametes versicolor by favouring the bioavailability of essential metals."	( Favouring the bioavailability of Zn and Cu to enhance the production of lignin-modifying enzymes in Trametes versicolor cultures. Lamy, I; Lebrun, JD; Mougin, C, 2011)	0.85
"High recalcitrant characteristics and low bioavailability rates due to aging processes can hinder high molecular weight polycyclic aromatic hydrocarbons (HMW-PAHs) bioremediation in real industrial polluted soils."	( Comparative assessment of bioremediation approaches to highly recalcitrant PAH degradation in a real industrial polluted soil. Covino, S; D'annibale, A; Lladó, S; Petruccioli, M; Solanas, AM; Viñas, M, 2013)	0.39
" Low bioavailability compounds (oxidized lignin and polyphenols of plant origin) remain in colonised leaves, even after fungal activity diminishes, and suggests a possible pathway for the sequestration of carbon in wetlands."	( High spatial resolution infrared micro-spectroscopy reveals the mechanism of leaf lignin decomposition by aquatic fungi. Baldwin, DS; Kappen, P; Kerr, JL; Puskar, L; Rees, GN; Silvester, E; Tobin, MJ, 2013)	0.88
"6 mL methaneg(-1) total lignin in OPEFB, and at the same time improve the bioavailability of lignocellulosic matters for further enzymatic hydrolysis."	( Characterization of anaerobic consortia coupled lignin depolymerization with biomethane generation. He, J; Wu, YR, 2013)	0.95
" Indeed, biochars efficiently reduce the bioavailability of organic and inorganic pollutants."	( Elaboration, characteristics and advantages of biochars for the management of contaminated soils with a specific overview on Miscanthus biochars. Deboffe, C; Douay, F; Heymans, S; Janus, A; Pelfrêne, A; Waterlot, C, 2015)	0.42
" Here, we propose using the transcriptomic response of the plant biomass-deconstructing microbe, Caldicellulosiruptor saccharolyticus, as a direct measure of how suitable a sample of plant biomass may be for fermentation based on the bioavailability of polysaccharides."	( Caldicellulosiruptor saccharolyticus transcriptomes reveal consequences of chemical pretreatment and genetic modification of lignocellulose. Blumer-Schuette, SE; Chiang, VL; Conway, JM; Kelly, RM; Khatibi, P; Lewis, DL; Li, Q; Zurawski, JV, 2017)	0.46
"We investigated the effects of organic amendments (thermophilic compost, vermicompost, and coconut coir) on the bioavailability of trace heavy metals of Zn, Cd, Pb, Co, and Ni from heavy metal-spiked soils under laboratory conditions."	( Phytoremediation of Heavy Metal-Contaminated Soil by Switchgrass: A Comparative Study Utilizing Different Composts and Coir Fiber on Pollution Remediation, Plant Productivity, and Nutrient Leaching. Bellitürk, K; Görres, JH; Shrestha, P, 2019)	0.51
" These findings indicate how nonsteroidal ligands of SHBG maybe designed to modulate the bioavailability of sex steroids."	( Molecular interactions between sex hormone-binding globulin and nonsteroidal ligands that enhance androgen activity. Das, S; Hammond, GL; Round, P; Van Petegem, F; Wähälä, K; Wu, TS, 2020)	0.56
" In this review, we summarize the recent technological advances in maximizing the bioavailability of different algal resources."	( Emerging technologies for conversion of sustainable algal biomass into value-added products: A state-of-the-art review. Wu, YR; Zhang, F; Zhang, K, 2021)	0.62
" In conclusion, applying I/S in cattle manure composting effectively improved the abundance, bioavailability of lignin degradation functional gene enzymes and the composting efficiency."	( Illite/smectite clay regulating laccase encoded genes to boost lignin decomposition and humus formation in composting habitats revealed by metagenomics analysis. Li, G; Li, Q; Meng, Q; Niu, Q; Wang, S; Yan, H; Zhu, Q, 2021)	1.07
" Meanwhile, application of P compounds to soils decreases the bioavailability of heavy metals."	( Effect of alkaline lignin on immobilization of cadmium and lead in soils and the associated mechanisms. Dai, Z; He, L; Liu, X; Tang, C; Xu, J, 2021)	0.95
" A 120-day incubation study examined the effects of alkaline lignin on Cd, Pb and P bioavailability and transformation in Cd or Cd/Pb co-contaminated red and cinnamon soils and elucidated the associated mechanisms."	( Alkaline lignin does not immobilize cadmium in soils but decreases cadmium accumulation in the edible part of lettuce (Lactuca sativa L.). Dai, Z; He, L; Hong, Z; Lin, J; Liu, X; Tang, C; Xu, J; Yu, Y, 2022)	1.38
" However, the low bioavailability of LCM due to the recalcitrant nature of plant cell components, the complexity and compositional heterogeneity of LCM monomers, and the limited metabolic flexibility of wild-type product-forming microorganisms to simultaneously utilize various LCM monomers are major roadblocks."	( Recent progress and challenges in biotechnological valorization of lignocellulosic materials: Towards sustainable biofuels and platform chemicals synthesis. Arhin, SG; Cesaro, A; Di Capua, F; Esposito, G, 2023)	0.91
"Oral drug delivery is a common route for management of inflammatory bowel disease (IBD) but suffers from low bioavailability and systemic side effects during passage through the alimentary canal."	( Synthetic Lignin-Derived Therapeutic Nano Reagent as Intestinal pH-Sensitive Drug Carriers Capable of Bypassing the Gastric Acid Environment for Colitis Treatment. Chen, M; Chen, W; Ma, X; Shi, J; Wang, L; Wang, Y; Yang, J; Yang, X; Ye, H; Yue, F; Zhao, C, 2023)	1.31
"Exploiting bamboo shoot shells (BSS) as feedstocks for biorefining is a crucial scheme to advance the bioavailability of bamboo shoots."	( Implementing dilute acid pretreatment coupled with solid acid catalysis and enzymatic hydrolysis to improve bioconversion of bamboo shoot shells. He, YC; Huang, C; Qian, H; Tang, W; Tang, Z, 2023)	0.91
" Lignin is a non-digestible, major component of the seed coat with negative effect on sensory quality, bioavailability and usage of oilseed rape's protein."	( Homoeologous non-reciprocal translocation explains a major QTL for seed lignin content in oilseed rape (Brassica napus L.). Holtgräwe, D; Holzenkamp, K; Möllers, C; Schilbert, HM; Viehöver, P, 2023)	2.05
" Here, we show the improvement of HSAL on plant nutrient bioavailability and growth through its metal chelating capacity."	( A lignin-derived material improves plant nutrient bioavailability and growth through its metal chelating capacity. Aoki, D; Busch, W; Feng, Z; Fukushima, K; Inukai, Y; Kawai, T; Li, B; Lin, X; Liu, Q; Matsushita, Y; Shi, W; Xiao, Y, 2023)	1.63

Excerpt	Relevance	Reference
" Rats were then orally dosed with [3H] T-2 toxin and urine and feces were collected for 21 hours after which all animals were killed and tissues excised."	( Effect of diet on T-2 toxicosis. Carson, MS; Smith, TK, 1984)	0.27
" Dose-response curves indicated that pectin, lignin and alginate significantly reduced chick growth at all levels of dietary folacin."	( Effects of dietary fiber on the bioavailability of folic acid monoglutamate. Damron, BL; Gregory, JF; Ristow, KA, 1982)	0.52
"5 or 20% alfalfa for 2 weeks and then dosed orally with [3H]T-2 toxin."	( Effect of feeding alfalfa and refined plant fibers on the toxicity and metabolism of T-2 toxin in rats. Carson, MS; Smith, TK, 1983)	0.27
" The adsorption experiments were performed under various conditions such as different initial concentrations, pH, adsorbent dosage and adsorbent particle size."	( Sorption of copper(II) ion from aqueous solution by Tectona grandis l.f. (teak leaves powder). King, P; Kumar, YP; Prasad, VS; Srinivas, P, 2006)	0.33
" These products can have high temperature stability in process conditions in the range of 55-60 degrees C (with present industrial products at 45-50 degrees C) and clearly improved specific activity, essentially decreasing the protein dosage required for an efficient hydrolysis of lignocellulosic substrates."	( Thermostable enzymes in lignocellulose hydrolysis. Alapuranen, M; Puranen, T; Siika-Aho, M; Vehmaanperä, J; Viikari, L, 2007)	0.34
" pH, catalyst dosage and illumination on lignin degradation was investigated."	( Photocatalytic degradation of lignin using Pt/TiO2 as the catalyst. Chang, CN; Chao, AC; Chiang, YP; Ma, YS; Sung, HF, 2008)	0.9
" Gene expression analysis revealed different fates of gene duplications, largely confirming plants are tolerant to gene dosage effects."	( Comparative genome analysis of lignin biosynthesis gene families across the plant kingdom. Bozell, JJ; Burris, JN; Cheng, MZ; Davis, M; Doeppke, C; Gao, P; Hayes, DG; Hu, J; Labbe, N; Reichel, KL; Shi, W; Stewart, CN; Stewart, NR; Sykes, RW; Syrenne, RD; Xu, Z; Yang, X; Ye, X; Yuan, JS; Zhang, D; Zhou, X, 2009)	0.64
" Dose-response experiments with a typical cellulase cocktail enabled a multidimensional analysis of the interrelationships of enzyme load and the rate, time, and extent of the reaction."	( Kinetics of enzymatic high-solid hydrolysis of lignocellulosic biomass studied by calorimetry. Borch, K; Lumby, E; McFarland, K; Olsen, SN; Westh, P, 2011)	0.37
" The effects of catalyst dosage (mole ratio of catalyst to glucose units in the feedstock) and reaction temperature on HMF yields were investigated to obtain optimal process conditions."	( Catalytic hydrolysis of lignocellulosic biomass into 5-hydroxymethylfurfural in ionic liquid. Wang, P; Wang, S; Yu, H; Zhan, S, 2011)	0.37
"In this study, a strategy to reduce enzyme dosage is evaluated by applying two post-treatments, oxygen delignification and mechanical refining."	( Reduction of enzyme dosage by oxygen delignification and mechanical refining for enzymatic hydrolysis of green liquor-pretreated hardwood. Chang, HM; Jameel, H; Koo, BW; Park, S; Phillips, RB; Treasure, TH, 2011)	0.37
"08 mg/g dry biomass with 20 FPU g(-1) dry biomass of enzyme dosage under optimum condition."	( Saccharification of Kans grass using enzyme mixture from Trichoderma reesei for bioethanol production. Ghosh, S; Kataria, R, 2011)	0.37
" A novel approach with a combination of response surface methodology (RSM) and uniform design (UD) was employed to evaluate the effects and interactions of three main influential factors, coagulant dosage, flocculant dosage and pH, on the treatment efficiency in terms of the supernatant turbidity and lignin removals as well as the water recovery."	( Optimization of the coagulation-flocculation process for pulp mill wastewater treatment using a combination of uniform design and response surface methodology. Chen, YZ; Wang, JP; Wang, Y; Yu, HQ; Yuan, SJ, 2011)	0.54
" The assays were carried out using a 2(2) experimental designs whose variables were concentration of Mn(2+) (33 and 1,000 μM) and semicontinuous dosage of the H(2)O(2) (0."	( Detoxification of azo dyes mediated by cell-free supernatant culture with manganese-dependent peroxidase activity: effect of Mn2+ concentration and H2O2 dose. Contreras, E; Palma, C; Urra, J; Vásquez, C, )	0.13
"5 U/mL laccase whilst higher dosage showed no improvement."	( Removal of monomer delignification products by laccase from Trametes versicolor. Amann, M; Faulstich, M; Kolb, M; Schieder, D; Sieber, V, 2012)	0.38
"3% (w/v) dosage of acrylic acid-grafted coir pith, a system pH of 2, a contact time of 22 h, a temperature of 30 °C, a particle size of <150 μm and an initial Cr(VI) of 1,171 mg l(-1)."	( Cr(VI) adsorption from electroplating plating wastewater by chemically modified coir pith. Suksabye, P; Thiravetyan, P, 2012)	0.38
"SPORL (Sulfite Pretreatment to Overcome Recalcitrance of Lignocellulose) pretreatment was applied to switchgrass and optimized through an experimental design using Response Surface Methodology within the range of temperature (163-197 °C), time (3-37 min), sulfuric acid dosage (0."	( Sulfite (SPORL) pretreatment of switchgrass for enzymatic saccharification. Pan, XJ; Yang, Q; Zhang, DS; Zhu, JY, 2013)	0.39
" From the dose-response curve, the 50% cytotoxic concentration (CC(50)) and the concentration that increased the viability of the UV-irradiated cells to 50% of the control value (EC(50)) were determined."	( Anti-UV activity of lignin-carbohydrate complex and related compounds. Hirano, K; Kobayashi, M; Koh, T; Machino, M; Nanbu, T; Ohno, H; Sakagami, H; Shimada, J; Yamamoto, M, )	0.45
" The application of the optimal dosage made possible the increase of the sugar yield from 33 to 54 %, and at the same time the reduction of the quantity of enzymatic mixture in 40 %, with respect to the initial dosage."	( Enhanced saccharification of biologically pretreated wheat straw for ethanol production. Lema, JM; López-Abelairas, M; Lu-Chau, TA, 2013)	0.39
"The capacity of laccase from Myceliophthora thermophila to promote the oxidative polymerisation of Kraft lignin (KL) was evaluated in several conditions of pH, temperature, enzyme dosage and treatment time."	( Polymerisation of Kraft lignin from black liquors by laccase from Myceliophthora thermophila: effect of operational conditions and black liquor origin. Fernández-Costas, C; Gouveia, S; Moldes, D; Sanromán, MA, 2013)	0.91
" At the same dosage applied, PDADMAC resulted in a higher adsorption of lignocelluloses on PCC than CPAM did due to its higher charge density."	( Improving the adsorption of lignocelluloses of prehydrolysis liquor on precipitated calcium carbonate. Fatehi, P; Hamdan, FC; Ni, Y; Shen, J, 2013)	0.39
" LA was used in combination with aluminum sulfate or polyaluminum chloride, namely Al-LA (Al was dosed firstly) and LA-Al (LA was dosed firstly), in humic acid water treatment."	( Characterization of size, strength and structure of aluminum-polymer dual-coagulant flocs under different pH and hydraulic conditions. Dong, M; Gao, B; Li, Q; Rong, H; Sun, S; Yue, Q; Zhao, Y, 2013)	0.39
"2% was achieved at a solid load of 15% and an enzyme dosage of 15 FPU/g pretreated corn stover."	( Efficient production of bioethanol from corn stover by pretreatment with a combination of sulfuric acid and sodium hydroxide. Kida, K; Morimura, S; Nishimura, H; Takei, S; Tan, L; Tang, YQ, 2013)	0.39
" Several model compound studies indicate that variations in the reaction media, such as the pH and the enzyme dosage used, have an impact on the observed product distribution of laccase promoted oxidation, but no detailed study has been reported to explain these results."	( On the factors affecting product distribution in laccase-catalyzed oxidation of a lignin model compound vanillyl alcohol: experimental and computational evaluation. Heinonen, P; Karhunen, P; Kruus, K; Lahtinen, M; Oivanen, M; Sipilä, J, 2013)	0.62
"The high costs of enzymatic hydrolysis along with the high enzyme dosage are often considered as the major bottlenecks in lignocellulosic bioconversion."	( Enzymatic hydrolysis, adsorption, and recycling during hydrolysis of bagasse sulfite pulp. Liu, B; Ouyang, J; Yu, H; Zhang, M; Zheng, Z, 2013)	0.39
" Enzymatic hydrolysis of natural wheat straw showed that all the treatments using mixtures of cellulase and an optimized amount of EXLX1, released greater quantities of sugars than those using cellulase alone, regardless of cellulase dosage and incubation time."	( Evaluation of bacterial expansin EXLX1 as a cellulase synergist for the saccharification of lignocellulosic Agro-industrial wastes. Lin, H; Shen, Q; Wang, Q; Zhan, JM; Zhao, YH, 2013)	0.39
"74% respectively) on BPAC were obtained at optimized pH of 2, contact time of 30 h and adsorbent dosage of 30 g/100 ml."	( Treatment and decolorization of biologically treated Palm Oil Mill Effluent (POME) using banana peel as novel biosorbent. Chong, MF; Mohammed, RR, 2014)	0.4
" In the first assay, 4 duodenally cannulated Holstein steers housed in metabolism cages, dosed with C32n-alkane, and fed Avena strigosa plus concentrate and increasing levels of tannin extract to reduce ruminal digestibility, were used in a Latin square design."	( Technical note: Evaluation of markers for estimating duodenal digesta flow and ruminal digestibility: Acid detergent fiber, sulfuric acid detergent lignin, and n-alkanes. Almeida, JG; Alves, TP; Kozloski, GV; Mesquita, FR; Moraes Genro, TC; Ribeiro Filho, HM; Stefanello, CM, 2014)	0.6
" Effects of different dosing sequences, Al dosed first and LA dosed first, were also investigated."	( Advanced lignin-acrylamide water treatment agent by pulp and paper industrial sludge: synthesis, properties and application. Gao, B; Li, Q; Rong, H; Sun, S; Wang, Y; Yang, Z; Yue, Q; Zhao, Y, 2013)	0.81
" Hardwood biomass residues were efficiently digested at low enzyme dosage (5 FPU/g cellulose) whereas the softwood residues required notably higher enzyme dosage (20 FPU) for sufficient conversion."	( Enzymatic hydrolysis of hardwood and softwood harvest residue fibers released by sulfur dioxide-ethanol-water fractionation. Bankar, S; Iakovlev, M; Tunc, MS; van Heiningen, A; Yamamoto, M, 2014)	0.4
"38%, respectively, using a regular industrial yeast strain at moderate cellulase dosage and high solids loading."	( An alternative feedstock of corn meal for industrial fuel ethanol production: delignified corncob residue. Bao, J; Lei, C; Xiao, L; Zhang, J, 2014)	0.4
" Pretreated biomass solid was then enzymatic hydrolyzed by commercial enzyme Cellic®CTec2 (Novozymes) with enzyme dosage of 35 FPU/g to achieve reducing sugars."	( Efficient pretreatment of Vietnamese rice straw by soda and sulfate cooking methods for enzymatic saccharification. Dien, le Q; Hoa, DT; Hoang, PH; Phuong, NT, 2015)	0.42
" This work investigated the feasibility of using Ag40-AgCl/ZnO to degrade lignin under natural solar light and then subsequent methane production with influencing factors like solution pH, dosage of catalyst and initial lignin concentration being considered."	( Photocatalytic degradation of lignin on synthesized Ag-AgCl/ZnO nanorods under solar light and preliminary trials for methane fermentation. Lei, Z; Li, H; Liu, C; Lu, B; Zhang, Z, 2015)	0.94
"296 g/gTVS was achieved at optimal hydrolysis conditions (microwave temperature = 190°C, time = 10 min, and cellulase dosage = 5 wt%)."	( Characterisation of water hyacinth with microwave-heated alkali pretreatment for enhanced enzymatic digestibility and hydrogen/methane fermentation. Cen, K; Cheng, J; Ding, L; Lin, R; Song, W; Xie, B; Zhou, J, 2015)	0.42
" High dosage of hydrogen peroxide is needed to effectively digest lignin, but excessive hydrogen peroxide may lead to recondensation of formed fragments in digested lignin."	( Microwave-assisted oxidative digestion of lignin with hydrogen peroxide for TOC and color removal. Huang, X; Ouyang, X; Qiu, X; Ruan, T, 2015)	0.92
" The effect of various reaction parameters such as wastewater pH, adsorbent dosage and temperature was studied."	( Utilisation of sewage sludge derived adsorbents for the removal of recalcitrant compounds from wastewater: Mechanistic aspects, isotherms, kinetics and thermodynamics. Garg, A; Gupta, A, 2015)	0.42
"2% dosage with negligible HDSs loss."	( Separation and purification of hemicellulose-derived saccharides from wood hydrolysate by combined process. Fu, Y; Jiang, J; Qin, M; Wang, X; Wang, Z; Zhuang, J, 2015)	0.42
" As it had multiple functional groups from the raw materials, the amphoteric flocculant showed high color removal efficiency to anionic (acid blue 113, >95%), neutral (reactive black 5, >95%) and cationic dyes (methyl orange, >50%) in a wide range of flocculant dosage and pH windows."	( Preparation of lignosulfonate-acrylamide-chitosan ternary graft copolymer and its flocculation performance. He, K; Lou, T; Wang, X; Zhao, W, 2015)	0.42
" The effects of reaction temperature, time, hydrogen pressure and catalyst dosage on the catalytic performance of lignin species were investigated."	( Investigation on the structural effect of lignin during the hydrogenolysis process. Long, J; Ma, L; Shu, R; Wang, C; Wang, T; Wu, Q; Xu, Y; Yuan, Z; Zhang, Q, 2016)	0.91
" The enhancement increased with the SXSL dosage and the xylanase loading."	( Enhancing enzymatic hydrolysis of xylan by adding sodium lignosulfonate and long-chain fatty alcohols. Fu, J; Huang, J; Lou, H; Pang, Y; Qiu, K; Qiu, X; Yuan, L, 2016)	0.43
" Conversely, the less aggressive experimental conditions, regarding regent dosage and downsizing, favored the release of biodegradable organic matter."	( Thermochemical pretreatment of lignocellulose residues: assessment of the effect on operational conditions and their interactions on the characteristics of leachable fraction. Carvajal, A; Contreras, E; Palma, C; Vásquez, D, 2015)	0.42
" The increased expression levels of lignin and cellulose synthesis key genes in the haploid situation illustrated that dosage compensation may account for genome dosage effect in our study."	( Ploidy effect and genetic architecture exploration of stalk traits using DH and its corresponding haploid populations in maize. Chen, S; Hu, H; Li, J; Li, W; Liu, J; Liu, W; Meng, Y, 2016)	0.71
"67 g/(L h) at 10 FPU/g cellulase dosage and 15% (w/w) solids content, an increase of 49."	( Periodic peristalsis increasing acetone-butanol-ethanol productivity during simultaneous saccharification and fermentation of steam-exploded corn straw. Chen, H; Li, J; Wang, L, 2016)	0.43
"3% with a very low cellulase dosage (3FPU/g)."	( A two-stage pretreatment process using dilute hydrochloric acid followed by Fenton oxidation to improve sugar recovery from corn stover. Chang, HM; Jameel, H; Li, W; Liu, Q; Ma, L; Ma, Q; Zhang, T, 2016)	0.43
" The acid and alkali sequence in the two-stage pretreatment process was compared, and their dosage was optimized."	( Comparison of two-stage acid-alkali and alkali-acid pretreatments on enzymatic saccharification ability of the sweet sorghum fiber and their physicochemical characterizations. Cai, D; Chen, C; Li, P; Li, S; Qin, P; Wang, Y; Wang, Z; Zhang, C, 2016)	0.43
"In this study, commercial surfactants have been investigated at economically viable dosage to enhance the enzymatic saccharification of pretreated wheat straw at high solid loadings."	( Investigating the enzyme-lignin binding with surfactants for improved saccharification of pilot scale pretreated wheat straw. Agrawal, R; Basu, B; Kapoor, M; Mondal, S; Satlewal, A, 2017)	0.76
" The dough increased water absorption by 2% in the specified dosage range."	( Effects of wheat-bran arabinoxylan as partial flour replacer on bread properties. Chimphango, AFA; Koegelenberg, D, 2017)	0.46
"0% using corn cobs with an enzyme dosage of 5 FPU/g-biomass."	( Characterization of cellulolytic enzyme system of Schizophyllum commune mutant and evaluation of its efficiency on biomass hydrolysis. Champreda, V; Eurwilaichitr, L; Fujii, T; Inoue, H; Kittisenachai, S; Rattanaphanjak, P; Roytrakul, S; Sornlake, W, 2017)	0.46
"In a 30-day survival study, performed in CBA mice, BP-C2, at a dosage of 81."	( Radioprotective and radiomitigative effects of BP-C2, a novel lignin-derived polyphenolic composition with ammonium molybdate, in two mouse strains exposed to total body irradiation. Anisimov, VN; Baldueva, IA; Bykov, VN; Drachev, IS; Fedoros, EI; Gubareva, EA; Kraev, SY; Maydin, MA; Panchenko, AV; Pigarev, SE, 2018)	0.72
" When water dosage was increased from 50 to 500 times of the WWS weight, the ash content gradually decreased during prewashing process, which facilitated lignin solubilization in subsequent p-toluenesulfonic acid (p-TsOH) hydrolysis."	( Improving cellulose nanofibrillation of waste wheat straw using the combined methods of prewashing, p-toluenesulfonic acid hydrolysis, disk grinding, and endoglucanase post-treatment. Bian, H; Dai, H; Fang, G; Gao, Y; Yang, Y, 2018)	0.68
" Supplementing a commercial cellulase with increasing dosage of P33 enzyme cocktail from 1 to 5 mg/g substrate increased the release of reducing sugars from delignified corn stover by 21."	( The composition of accessory enzymes of Penicillium chrysogenum P33 revealed by secretome and synergistic effects with commercial cellulase on lignocellulose hydrolysis. Liu, J; Liu, L; Wang, F; Wang, R; Yang, J; Yang, Y; Yuan, H, 2018)	0.48
"High dosage of enzyme is required to achieve effective lignocellulose hydrolysis, especially at high-solid loadings, which is a significant barrier to large-scale bioconversion of lignocellulose."	( Differential reinforcement of enzymatic hydrolysis by adding chemicals and accessory proteins to high solid loading substrates with different pretreatments. Du, J; Liu, G; Qu, Y; Song, W; Zhang, X; Zhao, J, 2018)	0.48
"Fenton-based processes with four different iron salts in two different dosing modes were used to pretreat rice straw (RS) samples to increase their enzymatic digestibility."	( Effect of iron salt type and dosing mode on Fenton-based pretreatment of rice straw for enzymatic hydrolysis. Dai, X; Gan, YY; Ma, J; Qin, YH; Wang, CW; Wang, TL; Wang, WG; Wu, H; Wu, ZK; Xiong, ZY; Yang, L; Zhou, SL, 2018)	0.48
", ∼15%) is suitable for ASP, because a pretty perfect glucose yield (91%) was obtained using a low dosage of enzyme loadings (5 FPU of cellulases/g dry matter)."	( Impact of lignin content on alkaline-sulfite pretreatment of Hybrid Pennisetum. Chu, J; Hao, X; Jia, L; Qin, Y; Wang, J; Yang, M; Zhang, J, 2018)	0.88
" The dosage of the lignin polymer required for reaching the maximum removal had a linear relationship with the dye concentration."	( Cationic High Molecular Weight Lignin Polymer: A Flocculant for the Removal of Anionic Azo-Dyes from Simulated Wastewater. Fatehi, P; Hou, Q; Kong, F; Wang, S, 2018)	1.1
"4% with 33% reduction of cellulase dosage due to decreased non-specific adsorption of cellulase on residual lignin."	( Synergy of hemicelluloses removal and bovine serum albumin blocking of lignin for enhanced enzymatic hydrolysis. Ding, D; Li, P; Ramaswamy, S; Xu, F; Zhang, X, 2019)	0.96
" The effects of temperature and alkali dosage on structural alterations were determined by chemical composition, Brunauer Emmett Teller (BET) and gel permeation chromatography (GPC)."	( Bioethanol production from bamboo with alkali-catalyzed liquid hot water pretreatment. Deng, J; Qin, Y; Shi, Z; Xu, G; Yang, H; Yang, J, 2019)	0.51
" Microscopic and rheological characterization indicated that the molecular weight and concentration of lignin, the APG dosage and the oil/water ratio had important influences on the microstructure and stability of the HIPEs."	( Development of anti-photo and anti-thermal high internal phase emulsions stabilized by biomass lignin as a nutraceutical delivery system. Chen, K; Lei, L; Qian, Y; Qiu, X; Yang, D, 2019)	0.95
" The incorporation of PDADMAC into the system reduced the dosage of FA required for achieving acceptable lignocellulose removals."	( Isolation of lignocelluloses from the spent liquor of thermomechanical pulping process with fly ash and cationic polymer. Fatehi, P; Liu, Z; Sun, Y, 2019)	0.51
"53 at the dosage of 5%, and the lotions containing lignin submicrometer particles had good UV-blocking properties."	( Preparation of organic acid lignin submicrometer particle as a natural broad-spectrum photo-protection agent. Bian, J; Li, MF; Li, SX; Ma, MG; Peng, F; Wu, XF, 2019)	1.06
" Utilizing DoE we systematically modified biosensor dose-response behavior by increasing the maximum signal output (up to 30-fold increase), improving dynamic range (>500-fold), expanding the sensing range (∼4-orders of magnitude), increasing sensitivity (by >1500-fold), and modulated the slope of the curve to afford biosensors designs with both digital and analogue dose-response behavior."	( Development of High-Performance Whole Cell Biosensors Aided by Statistical Modeling. Berepiki, A; Dixon, N; Kent, R; Machado, LFM, 2020)	0.56
" Optimization of the pretreatment conditions such as temperature, sulfolane/water ratio, and alkaline catalyst (NaOH) dosage were comprehensively investigated for effective lignin extraction from willow."	( Pretreatment of willow using the alkaline-catalyzed sulfolane/water solution for high-purity and antioxidative lignin production. Chen, J; Ji, X; Jiang, W; Lyu, G; Mao, J; Shao, L; Wang, C; Xu, F; Xu, M; Yang, G; Yoo, CG; Zhong, L, 2020)	0.96
"33 with a dosage ∼10 wt % lasting for over 8 h under UV radiation."	( Bioinspired Lignin-Polydopamine Nanocapsules with Strong Bioadhesion for Long-Acting and High-Performance Natural Sunscreens. Qian, Y; Qiu, X; Wang, J; Zeng, H; Zhou, Y, 2020)	0.94
" It showed a higher boosting effect on the enzymatic saccharification of complex lignocellulosic substrates associated with xyloglucan than on the lignocellulosic substrates without xyloglucan particularly in low commercial cellulase dosage cases."	( A highly xyloglucan active lytic polysaccharide monooxygenase EpLPMO9A from Eupenicillium parvum 4-14 shows boosting effect on hydrolysis of complex lignocellulosic substrates. Chen, K; Ding, S; Long, L; Shi, Y, 2021)	0.62
"AS (Aquasolv) Lignin produced via Liquid Hot Water Pretreatment and Enzymatic Hydrolysis has shown potential as an active pharmaceutical ingredient and/or excipient in solid dosage forms."	( Application of Aquasolv Lignin in ibuprofen-loaded pharmaceutical formulations obtained via direct compression and wet granulation. Gil-Chávez, J; Leopold, CS; Padhi, SSP; Smirnova, I, 2021)	1.29
" Besides, the impact of various additives on pretreated substrate enzymatic hydrolysis confirmed that Tween 80 was the best enzymatic additive, which could significantly improve the glucose produced from pretreated SCB and remarkably reduce the hydrolysis time (from 72 h to 48 h) and enzyme dosage (from 20 FPU/g pretreated solid to 10 FPU/g pretreated solid)."	( Investigation of choline chloride-formic acid pretreatment and Tween 80 to enhance sugarcane bagasse enzymatic hydrolysis. Jin, Y; Ling, R; Wei, W; Wu, W; Yuan, Y, 2021)	0.62
" Additional fecal samples were taken at 2-h intervals following marker dosing until 96-h post-dosing to evaluate digesta MRT."	( Apparent digestibility, fecal particle size, and mean retention time of reduced lignin alfalfa hay fed to horses. Grev, AM; Hathaway, MR; Martinson, KL; Reiter, AS; Sheaffer, CC; Wells, MS, 2021)	0.85
" Results showed that the effects of these additives on enhancing enzymatic hydrolysis were positively correlated with substrate content; when the solid dosage was 20% (w/v), the presence of sophorolipid and whey protein increased glucose yield by 17."	( Mechanisms of bio-additives on boosting enzymatic hydrolysis of lignocellulosic biomass. Asraful Alam, M; Chen, H; Huang, S; Wang, Z; Xu, C; Xu, J; Zhang, J; Zhuang, W, 2021)	0.62
" The results suggest that biochar dosing shows better environmental performance for all impact categories, especially in the consolidate bioprocessing case."	( Comparative life cycle assessment of biochar-based lignocellulosic biohydrogen production: Sustainability analysis and strategy optimization. Chen, C; Li, LQ; Ren, NQ; Wang, ZH; Yang, SS; Zhao, L, 2022)	0.72
" The effects of degree of lignin depolymerization, chemical composition of lignin oligomers and dosage of ECGE on thermal and mechanical properties of the cured products were investigated."	( Preparation and properties of novel bio-based epoxy resin thermosets from lignin oligomers and cardanol. Chu, F; Huo, S; Jin, C; Kong, Z; Liu, G, 2021)	1.15
"The effects of different factors including pH, adsorption time, adsorbent dosage and initial concentration of lead ions were explored."	( Biosorption of lead ions from aqueous solution by Clostridium tyrobutyricum immobilized in macroporous Ca-alginate-lignin beads. Gao, G; He, J; Jiang, L; Malkmes, MJ; Zhao, Q; Zheng, L; Zheng, W, 2022)	0.93
" Sunlight has been shown to cause and accelerate C release in semiarid ecosystems, yet the dose-response relationships for these effects have not been evaluated."	( Dose-responses for solar radiation exposure reveal high sensitivity of microbial decomposition to changes in plant litter quality that occur during photodegradation. Austin, AT; Ballaré, CL; Méndez, MS, 2022)	0.72
" The adding of SL into the enzymatic hydrolysis step could significantly lower the cellulase dosage and hydrolysis time from 20 FPU/g and 72 h to 10 FPU/g and 24 h, respectively, meanwhile keeping a high glucose yield of 90."	( Enhancement of sugar release from sugarcane bagasse through NaOH-catalyzed ethylene glycol pretreatment and water-soluble sulfonated lignin. Qi, J; Wang, B; Wang, X; Wei, W; Xiao, Y; Xie, M; Xu, J; Yu, Z; Zhao, W, 2022)	0.93
" In this study, LCC rich in carbohydrates was extracted from alkaline hemicellulose by using the xylanase-macroporous resin method, the effects of enzyme dosage and treatment time on LCC enrichment were discussed."	( Structural enrichment and identification of lignin-carbohydrate complex in alkaline stabilized system. Han, J; Li, J; Liang, C; Liu, Y; Pang, S; Qin, C; Wang, X; Yao, S; Zhao, J, 2022)	0.98
" However, due to low enzymatic hydrolysis (EH) yields and rates, a high dosage of the costly enzyme is required, which is a bottleneck for commercial applications."	( Positive role of non-catalytic proteins on mitigating inhibitory effects of lignin and enhancing cellulase activity in enzymatic hydrolysis: Application, mechanism, and prospective. Karimi, K; Madadi, M; Song, G; Sun, C; Sun, F; Tu, M; Xia, C; Zhang, E, 2022)	0.95
" A satisfying enzymatic conversion yield (>85%) at rather low cellulase enzyme dosage (10 FPU/g glucan) was obtained, which would indicate new understandings on the green and efficient bioconversion process on lignocellulosic biomass."	( Supramolecular Deconstruction of Bamboo Holocellulose via Hydrothermal Treatment for Highly Efficient Enzymatic Conversion at Low Enzyme Dosage. Ling, Z; Su, Y; Wang, P; Wang, Q; Wang, X; Yong, Q, 2022)	0.72
" The influence of experimental conditions: selenate concentration, adsorbent dosage and contact time on the adsorption capacity was investigated in a batch experimental mode."	( Lignin Microspheres Modified with Magnetite Nanoparticles as a Selenate Highly Porous Adsorbent. Dimitrijevic, S; Marinkovic, AD; Marjanovic, V; Markovic, R; Peric-Grujic, A; Steharnik, M; Đolic, M, 2022)	2.16
" This work proposed a very effective method to improve the efficiency of enzymatic hydrolysis and reduce the dosage of the enzyme by adding biosurfactants."	( Biosurfactant promoted enzymatic saccharification of alkali‑pretreated reed straw. Cheng, Y; Du, J; Liu, M; Lu, J; Tan, W; Tao, Y; Wang, H; Wang, Y; Zhang, X, 2023)	0.91
" Moreover, the blending of LNP at a low dosage (0."	( Lignin nanoparticle reinforced multifunctional polyvinyl alcohol/polyurethane composite hydrogel with excellent mechanical, UV-blocking, rheological and thermal properties. Gao, J; Liu, S; Wang, Q; Wang, Y; Wu, L, 2023)	2.35
" Adsorbent dosage and solution pH were taken into account to study their effects in the batch experiments."	( Cu(II) removal from water by trimercapto-s-triazine trisodium salt modified alkaline lignin. Gu, J; He, F; Song, X; Wang, Q; Xu, F, 2023)	1.13
"9% at a low cellulase dosage (5 FPU/g-glucan)."	( Achieving high enzymatic hydrolysis sugar yield of sodium hydroxide-pretreated wheat straw with a low cellulase dosage by adding sulfomethylated tannic acid. Hu, S; Huang, C; Jiang, B; Jin, Y; Wei, W; Wu, W; Zhang, T, 2023)	0.91
" coli HNIQLE-AlaDH expressing ω-transaminase from Aspergillus terreus and alanine dehydrogenase from Bacillus subtilis was firstly used aminate lignin-derived vanillin to vanillylamine by using a relatively low dosage of amine donors (vanillin:L-alanine:isopropylamine = 1:1:1, mol/mol/mol)."	( Biological valorization of lignin-derived vanillin to vanillylamine by recombinant E. coli expressing ω-transaminase and alanine dehydrogenase in a petroleum ether-water system. Chai, H; He, YC; Li, L; Ma, C, 2023)	1.41

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	570 (4.38)	18.7374
1990's	476 (3.66)	18.2507
2000's	1984 (15.25)	29.6817
2010's	6359 (48.87)	24.3611
2020's	3624 (27.85)	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	26 (0.19%)	5.53%
Reviews	1,470 (10.98%)	6.00%
Case Studies	5 (0.04%)	4.05%
Observational	0 (0.00%)	0.25%
Other	11,889 (88.79%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
acetylcarnitine Acetylcarnitine: An acetic acid ester of CARNITINE that facilitates movement of ACETYL COA into the matrices of mammalian MITOCHONDRIA during the oxidation of FATTY ACIDS.	4.9	1	1	O-acylcarnitine	human metabolite
1,2,4-trichlorobenzene 1,2,4-trichlorobenzene : A trichlorobenzene with chloro substituents at positions 1, 2 and 4.	2.13	1	0	trichlorobenzene
2,3-dihydroxybenzoic acid 2,3-dihydroxybenzoic acid: RN given refers to parent cpd. dihydroxybenzoic acid : Any member of the class of hydroxybenzoic acids carrying two phenolic hydroxy groups on the benzene ring and its derivatives.. 2,3-dihydroxybenzoic acid : A dihydroxybenzoic acid that is benzoic acid substituted by hydroxy groups at positions 2 and 3. It occurs naturally in Phyllanthus acidus and in the aquatic fern Salvinia molesta.	1.99	1	0	dihydroxybenzoic acid	human xenobiotic metabolite; plant metabolite
protocatechuic acid protocatechuic acid: RN given refers to parent cpd; structure. 3,4-dihydroxybenzoic acid : A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.	4.51	22	0	catechols; dihydroxybenzoic acid	antineoplastic agent; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor; human xenobiotic metabolite; plant metabolite
3-hydroxyanthranilic acid 3-Hydroxyanthranilic Acid: An oxidation product of tryptophan metabolism. It may be a free radical scavenger and a carcinogen.. 3-hydroxyanthranilic acid : An aminobenzoic acid that is benzoic acid substituted at C-2 by an amine group and at C-3 by a hydroxy group. It is an intermediate in the metabolism of the amino acid tryptophan.. 3-hydroxyanthranilate : A hydroxybenzoate that is the conjugate base of 3-hydroxyanthranilic acid.	7.73	3	0	aminobenzoic acid; monohydroxybenzoic acid	human metabolite; mouse metabolite
3-oxoadipic acid 3-oxoadipic acid: RN given refers to parent cpd. 3-oxoadipic acid : An oxo dicarboxylic acid consisting of adipic acid having a single oxo group at the 3-position.	3.11	4	0	dicarboxylic fatty acid; oxo dicarboxylic acid	bacterial xenobiotic metabolite; human metabolite
3-phenylpropionic acid 3-phenylpropionic acid: RN given refers to parent cpd. 3-phenylpropionic acid : A monocarboxylic acid that is propionic acid substituted at position 3 by a phenyl group.	2.76	3	0	benzenes; monocarboxylic acid	antifungal agent; human metabolite; plant 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.	2.78	3	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
4-hydroxybenzaldehyde [no description available]	3.94	12	0	hydroxybenzaldehyde	EC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor; mouse metabolite; plant metabolite
4-hydroxyphenylacetic acid 4-hydroxyphenylacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group.	2.43	2	0	monocarboxylic acid; phenols	fungal metabolite; human metabolite; mouse metabolite; plant metabolite
4-hydroxybenzoic acid 4-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring.	5.64	23	0	monohydroxybenzoic acid	algal metabolite; plant metabolite
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.	2.21	1	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.	5.6	12	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.	8.57	143	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.	4.7	8	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.	2.06	1	0	acetamides; carboximidic acid; monocarboxylic acid amide; N-acylammonia
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	7.85	56	0	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
adipic acid adipic acid : An alpha,omega-dicarboxylic acid that is the 1,4-dicarboxy derivative of butane.	4.52	6	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.	2.04	1	0	guanidines; primary amino compound	Escherichia coli metabolite; mouse metabolite
allantoin [no description available]	1.98	1	0	imidazolidine-2,4-dione; ureas	Escherichia coli metabolite; human metabolite; Saccharomyces cerevisiae metabolite; vulnerary
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	10.31	99	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
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.	2.03	1	0	arsenic oxoacid	Escherichia coli metabolite
quinacrine Quinacrine: An acridine derivative formerly widely used as an antimalarial but superseded by chloroquine in recent years. It has also been used as an anthelmintic and in the treatment of giardiasis and malignant effusions. It is used in cell biological experiments as an inhibitor of phospholipase A2.. quinacrine : A member of the class of acridines that is acridine substituted by a chloro group at position 6, a methoxy group at position 2 and a [5-(diethylamino)pentan-2-yl]nitrilo group at position 9.	2.25	1	0	acridines; aromatic ether; organochlorine compound; tertiary amino compound	antimalarial; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor
benzaldehyde [no description available]	7.58	2	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]	5.5	18	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.	10.38	10	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.	2.79	3	0	benzyl alcohols	antioxidant; fragrance; metabolite; solvent
betaine glycine betaine : The amino acid betaine derived from glycine.	2.82	3	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)	3.35	6	0	halide anion; monoatomic bromine
butyraldehyde [no description available]	2.08	1	0	butanals	biomarker; Escherichia coli metabolite; mouse metabolite
2,3-butylene glycol 2,3-butylene glycol: RN given refers to cpd without isomeric designation. butane-2,3-diol : A butanediol in which hydroxylation is at C-2 and C-3.	5.7	13	0	butanediol; glycol; secondary alcohol
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.	8.77	66	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.	5.55	7	0	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
cadaverine [no description available]	2.06	1	0	alkane-alpha,omega-diamine	Daphnia magna metabolite; Escherichia coli metabolite; mouse metabolite; plant metabolite
carbamates [no description available]	2.25	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.	9.16	15	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.	7.65	72	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.	2.05	1	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]	4.9	1	1	amino-acid betaine	human metabolite; mouse metabolite
catechol [no description available]	4.6	24	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).	13.26	328	2	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
chlordecone [no description available]	2.25	1	0	cyclic ketone; organochlorine compound	insecticide; persistent organic pollutant
choline [no description available]	6.18	34	0	cholines	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter; nutrient; plant metabolite; Saccharomyces cerevisiae metabolite
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.	6.01	19	0	tricarboxylic acid	antimicrobial agent; chelator; food acidity regulator; fundamental metabolite
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	5.32	51	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.	9.71	28	0	chlorine molecular entity; gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
coumarin 2H-chromen-2-one: coumarin derivative	2.67	3	0	coumarins	fluorescent dye; human metabolite; plant metabolite
4-vinylguaiacol 2-methoxy-4-vinylphenol: a germination inhibitor; also an odorant in green tea; structure in first source. 2-methoxy-4-vinylphenol : A member of the class of phenols that is guaiacol in which the hydrogen para- to the hydroxy group is replaced by a vinyl group.	8.07	4	0	phenols	flavouring agent; pheromone; 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).	5.3	48	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-methylcatechol 3-methylbenzene-1,2-diol: structure in first source. dihydroxytoluene : Any hydroxytoluene that has two hydroxy substituents. 3-methylcatechol : A methylcatechol carrying a methyl substituent at position 3. It is a xenobiotic metabolite produced by some bacteria capable of degrading nitroaromatic compounds present in pesticide-contaminated soil samples.	2.21	1	0	methylcatechol	bacterial xenobiotic 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.	2.15	1	0	cresol	human xenobiotic metabolite
octane Octanes: Eight-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives.. octane : A straight chain alkane composed of 8 carbon atoms.	2.06	1	0	alkane	xenobiotic
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.	4.16	16	0	benzenetriol; phenolic donor	algal metabolite
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	6.67	28	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.	8.76	2	0	gas molecular entity; hydracid; mononuclear parent hydride; sulfur hydride	Escherichia coli metabolite; genotoxin; metabolite; signalling molecule; toxin; vasodilator agent
pseudooxynicotine pseudooxynicotine: structure given in first source. pseudooxynicotine : An aminoacylpyridine that is pyridine substituted at position 3 by a 4-(methylamino)butanoyl group.	2.11	1	0	aminoacylpyridine; pyridine alkaloid
3-hydroxybutyric acid 3-Hydroxybutyric Acid: BUTYRIC ACID substituted in the beta or 3 position. It is one of the ketone bodies produced in the liver.. 3-hydroxybutyric acid : A straight-chain 3-hydroxy monocarboxylic acid comprising a butyric acid core with a single hydroxy substituent in the 3- position; a ketone body whose levels are raised during ketosis, used as an energy source by the brain during fasting in humans. Also used to synthesise biodegradable plastics.	3.33	5	0	(omega-1)-hydroxy fatty acid; 3-hydroxy monocarboxylic acid; hydroxybutyric acid	human metabolite
sorbitol [no description available]	2.08	1	0	hexitol
guaiacol Guaiacol: An agent thought to have disinfectant properties and used as an expectorant. (From Martindale, The Extra Pharmacopoeia, 30th ed, p747). methylcatechol : Any member of the class of catechols carrying one or more methyl substituents.. guaiacol : A monomethoxybenzene that consists of phenol with a methoxy substituent at the ortho position.	6.68	68	0	guaiacols	disinfectant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; expectorant; plant metabolite
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.	2.36	2	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.	5	11	0	2-hydroxydicarboxylic acid; C4-dicarboxylic acid	food acidity regulator; fundamental 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.	3.56	2	0	amino acid zwitterion; monocarboxylic acid; non-proteinogenic alpha-amino acid	ethylene releasers; plant metabolite
3,4-dihydroxyphenylacetic acid 3,4-Dihydroxyphenylacetic Acid: A deaminated metabolite of LEVODOPA.. (3,4-dihydroxyphenyl)acetic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine.. dihydroxyphenylacetic acid : A dihydroxy monocarboxylic acid consisting of phenylacetic acid having two phenolic hydroxy substituents.	3.77	3	0	catechols; dihydroxyphenylacetic acid	human metabolite
creatine [no description available]	1.94	1	0	glycine derivative; guanidines; zwitterion	geroprotector; human metabolite; mouse metabolite; neuroprotective agent; nutraceutical
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.	9.15	99	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
diacetyl butane-2,3-dione : An alpha-diketone that is butane substituted by oxo groups at positions 2 and 3. It is a metabolite produced during the malolactic fermentation.	2.04	1	0	alpha-diketone	Escherichia coli metabolite; Saccharomyces cerevisiae metabolite
dimethylamine [no description available]	2.94	4	0	methylamines; secondary aliphatic amine	metabolite
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	4.65	25	0	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
ethanolamine [no description available]	3.22	5	0	ethanolamines; primary alcohol; primary amine	Escherichia coli metabolite; human metabolite; mouse metabolite
formaldehyde paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy	7.02	36	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
glutaric acid glutaric acid: RN given refers to parent cpd. glutaric acid : An alpha,omega-dicarboxylic acid that is a linear five-carbon dicarboxylic acid.	2.17	1	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	Daphnia magna metabolite; human metabolite
glycine [no description available]	3.59	8	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.	7.99	64	0	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
alpha-glycerophosphoric acid [no description available]	2.21	1	0	glycerol monophosphate	algal metabolite; human metabolite
glycolaldehyde [no description available]	4.32	5	0	glycolaldehydes	fundamental metabolite; human metabolite
glycolic acid glycolic acid: RN given refers to parent cpd. glycolic acid : A 2-hydroxy monocarboxylic acid that is acetic acid where the methyl group has been hydroxylated.	2.93	4	0	2-hydroxy monocarboxylic acid; primary alcohol	keratolytic drug; 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.	7.49	2	0	2-oxo monocarboxylic acid; aldehydic acid	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
carbonic acid Carbonic Acid: Carbonic acid (H2C03). The hypothetical acid of carbon dioxide and water. It exists only in the form of its salts (carbonates), acid salts (hydrogen carbonates), amines (carbamic acid), and acid chlorides (carbonyl chloride). (From Grant & Hackh's Chemical Dictionary, 5th ed)	2.02	1	0	carbon oxoacid; chalcocarbonic acid	mouse metabolite
hydrogen cyanide Hydrogen Cyanide: Hydrogen cyanide (HCN); A toxic liquid or colorless gas. It is found in the smoke of various tobacco products and released by combustion of nitrogen-containing organic materials.. hydrogen cyanide : A one-carbon compound consisting of a methine group triple bonded to a nitrogen atom	3.35	1	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.	3.02	4	0	carbon oxoanion	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
dalteparin Dalteparin: A low-molecular-weight fragment of heparin, prepared by nitrous acid depolymerization of porcine mucosal heparin. The mean molecular weight is 4000-6000 daltons. It is used therapeutically as an antithrombotic agent. (From Merck Index, 11th ed)	2.13	1	0
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.	10.45	178	0	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
hydroquinone [no description available]	8.22	5	0	benzenediol; hydroquinones	antioxidant; carcinogenic agent; cofactor; Escherichia coli metabolite; human xenobiotic metabolite; mouse metabolite; skin lightening agent
imidazole imidazole: RN given refers to parent cpd. 1H-imidazole : An imidazole tautomer which has the migrating hydrogen at position 1.	3.01	4	0	imidazole
indoleacetic acid indoleacetic acid: RN given refers to unlabeled parent cpd; structure in Merck Index, 9th ed, #4841. auxin : Any of a group of compounds, both naturally occurring and synthetic, that induce cell elongation in plant stems (from Greek alphaupsilonxialphanuomega, "to grow").. indole-3-acetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.	2.83	3	0	indole-3-acetic acids; monocarboxylic acid	auxin; human metabolite; mouse metabolite; plant hormone; plant metabolite
iodine Iodine: A nonmetallic element of the halogen group that is represented by the atomic symbol I, atomic number 53, and atomic weight of 126.90. It is a nutritionally essential element, especially important in thyroid hormone synthesis. In solution, it has anti-infective properties and is used topically.. diiodine : Molecule comprising two covalently bonded iodine atoms with overall zero charge..	3.11	5	0	diatomic iodine	nutrient
itaconic acid itaconic acid : A dicarboxylic acid that is methacrylic acid in which one of the methyl hydrogens is substituted by a carboxylic acid group.	5.99	13	0	dicarboxylic acid; dicarboxylic fatty acid; olefinic compound	fungal metabolite; human metabolite
2,3,4,5-tetrahydroxypentanal [no description available]	2.07	1	0	hydroxyaldehyde; pentose; polyol
lipoamide Lipozyme: lipase from Rhizomucor miehei immobilized on anion exchange resin	2.31	1	0	dithiolanes; monocarboxylic acid amide	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
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.	2.7	3	0	alpha,omega-dicarboxylic acid	human metabolite
pyruvaldehyde Pyruvaldehyde: An organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.. methylglyoxal : A 2-oxo aldehyde derived from propanal.	2.07	1	0	2-oxo aldehyde; propanals	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	13.36	1,239	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
phytic acid Phytic Acid: Complexing agent for removal of traces of heavy metal ions. It acts also as a hypocalcemic agent.. myo-inositol hexakisphosphate : A myo-inositol hexakisphosphate in which each hydroxy group of myo-inositol is monophosphorylated.	5.43	4	0	inositol phosphate
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.	2.76	3	0	cyclitol; hexol
melatonin [no description available]	3.38	5	0	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
naphthalene [no description available]	4.11	4	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.	5	35	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.	2.53	2	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.	2.15	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.	8.27	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.	2.79	3	0	nitrogen oxoacid	protic solvent; reagent
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)	3.4	7	0	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.	3.27	4	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]	2.57	2	0	oxygen hydride	mouse metabolite
orotic acid Orotic Acid: An intermediate product in PYRIMIDINE synthesis which plays a role in chemical conversions between DIHYDROFOLATE and TETRAHYDROFOLATE.. orotic acid : A pyrimidinemonocarboxylic acid that is uracil bearing a carboxy substituent at position C-6.	2.71	3	0	pyrimidinemonocarboxylic acid	Escherichia coli metabolite; metabolite; 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.	5.7	24	0	alpha,omega-dicarboxylic acid	algal metabolite; human metabolite; plant metabolite
oxamic acid Oxamic Acid: Amino-substituted glyoxylic acid derivative.. oxamic acid : A dicarboxylic acid monoamide resulting from the formal condensation of one of the carboxy groups of oxalic acid with ammonia.	2.13	1	0	dicarboxylic acid monoamide	Escherichia coli 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.	2.49	2	0	aminobenzoic acid; aromatic amino-acid zwitterion	allergen; Escherichia coli metabolite; plant metabolite
4-nitrophenol 4-nitrophenol: RN given refers to parent cpd. mononitrophenol : A nitrophenol that is phenol carrying a single nitro substituent at unspecified position.. 4-nitrophenol : A member of the class of 4-nitrophenols that is phenol in which the hydrogen that is para to the hydroxy group has been replaced by a nitro group.	8.66	8	0	4-nitrophenols	human xenobiotic metabolite; mouse metabolite
palmitic acid Palmitic Acid: A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids.. hexadecanoic acid : A straight-chain, sixteen-carbon, saturated long-chain fatty acid.	2.75	3	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor; plant metabolite
parathion [no description available]	7.6	1	0	C-nitro compound; organic thiophosphate; organothiophosphate insecticide	acaricide; agrochemical; avicide; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; mouse metabolite
pentachlorophenol PENTA: structure given in first source	5.4	11	0	aromatic fungicide; chlorophenol; organochlorine pesticide; pentachlorobenzenes	human xenobiotic metabolite
phenanthrene phenanthrene : A polycyclic aromatic hydrocarbon composed of three fused benzene rings which takes its name from the two terms 'phenyl' and 'anthracene.'	3.89	12	0	ortho-fused polycyclic arene; ortho-fused tricyclic hydrocarbon; phenanthrenes	environmental contaminant; mouse metabolite
phenol [no description available]	7.53	91	0	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
phenylpyruvic acid phenylpyruvic acid: RN given refers to parent cpd. phenylpyruvate : A 2-oxo monocarboxylic acid anion resulting from deprotonation of the carboxy group of either keto- or enol-phenylpyruvic acid.. keto-phenylpyruvic acid : A 2-oxo monocarboxylic acid that is 3-phenylpropanoic acid substituted by an oxo group at position 2. It is an intermediate metabolite in the phenylalanine pathway.	7.34	2	0	2-oxo monocarboxylic acid	chromogenic compound; EC 6.4.1.1 (pyruvate carboxylase) inhibitor; fundamental metabolite
phenylacetic acid phenylacetic acid : A monocarboxylic acid that is toluene in which one of the hydrogens of the methyl group has been replaced by a carboxy group.	2.52	2	0	benzenes; monocarboxylic acid; phenylacetic acids	allergen; Aspergillus metabolite; auxin; EC 6.4.1.1 (pyruvate carboxylase) inhibitor; Escherichia coli metabolite; human metabolite; plant growth retardant; plant metabolite; Saccharomyces cerevisiae metabolite; toxin
phosphoric acid phosphoric acid: concise etchant is 37% H3PO4. phosphoric acid : A phosphorus oxoacid that consists of one oxo and three hydroxy groups joined covalently to a central phosphorus atom.	4.7	26	0	phosphoric acids	algal metabolite; fertilizer; human metabolite; NMR chemical shift reference compound; solvent
phthalic acid phthalic acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7178. phthalic acid : A benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions.	2.77	3	0	benzenedicarboxylic acid	human xenobiotic metabolite
diphosphoric acid diphosphoric acid : An acyclic phosphorus acid anhydride obtained by condensation of two molecules of phosphoric acid.	2.52	2	0	acyclic phosphorus acid anhydride; phosphorus oxoacid	Escherichia coli metabolite
prephenic acid prephenic acid: nonaromatic biosynthetic intermediate, probable immediate precursor of aromatic systems such as phenylalanine, tyrosine, tannins, flavanoids; isolated from cultures of mutant E coli; structure. (1s,4s)-prephenic acid : A prephenic acid having (1s,4s)-cis-configuration.. prephenic acid : An oxo dicarboxylic acid that consists of 4-hydroxycyclohexa-2,5-diene-1-carboxylic acid substituted by a 2-carboxy-2-oxoethyl group at position 1.	2.01	1	0	oxo dicarboxylic acid	Escherichia coli metabolite; plant 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.	4.08	3	0	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.	4.54	4	0	propan-1-ols; short-chain primary fatty alcohol	metabolite; protic solvent
propionic acid propionic acid : A short-chain saturated fatty acid comprising ethane attached to the carbon of a carboxy group.	2.52	2	0	saturated fatty acid; short-chain fatty acid	antifungal drug
putrescine [no description available]	2.86	3	0	alkane-alpha,omega-diamine	antioxidant; fundamental metabolite
pyridine azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.	3.29	6	0	azaarene; mancude organic heteromonocyclic parent; monocyclic heteroarene; pyridines	environmental contaminant; NMR chemical shift reference compound
pyrogallol benzenetriol : A triol in which three hydroxy groups are substituted onto a benzene ring.	5.35	17	0	benzenetriol; phenolic donor	plant 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.	8.12	5	0	2-oxo monocarboxylic acid	cofactor; fundamental 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.	2.5	2	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion	human metabolite
dithionite Dithionite: Dithionite. The dithionous acid ion and its salts.	2.78	3	0	sulfur oxide; sulfur oxoanion
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.	2.41	1	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.	2.96	3	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).	6.48	55	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion
spermidine [no description available]	2.99	4	0	polyazaalkane; triamine	autophagy inducer; fundamental metabolite; geroprotector
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.	11.58	24	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.	6.52	169	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.	4.62	25	0	sulfur oxide	Escherichia coli metabolite; food bleaching agent; refrigerant
taurine [no description available]	1.94	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.	2.72	3	0	primary alcohol; vitamin B1	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
thymine [no description available]	7.41	1	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.	6.04	19	0	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
trimethylamine [no description available]	7.55	2	0	methylamines; tertiary amine	Escherichia coli metabolite; human xenobiotic metabolite
trimethylsulfonium [no description available]	2.05	1	0	sulfonium compound	animal metabolite
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	2.71	3	0	pyrimidine nucleobase; pyrimidone	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; prodrug; Saccharomyces cerevisiae metabolite
uric acid Uric Acid: An oxidation product, via XANTHINE OXIDASE, of oxypurines such as XANTHINE and HYPOXANTHINE. It is the final oxidation product of purine catabolism in humans and primates, whereas in most other mammals URATE OXIDASE further oxidizes it to ALLANTOIN.. uric acid : An oxopurine that is the final oxidation product of purine metabolism.. 6-hydroxy-1H-purine-2,8(7H,9H)-dione : A tautomer of uric acid having oxo groups at C-2 and C-8 and a hydroxy group at C-6.. 7,9-dihydro-1H-purine-2,6,8(3H)-trione : An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8.	2.68	3	0	uric acid	Escherichia coli metabolite; human metabolite; mouse metabolite
urea pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.	6.22	30	1	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
vanillin Vanilla: A plant genus of the family ORCHIDACEAE that is the source of the familiar flavoring used in foods and medicines (FLAVORING AGENTS).	8.41	84	0	benzaldehydes; monomethoxybenzene; phenols	anti-inflammatory agent; anticonvulsant; antioxidant; flavouring agent; plant metabolite
alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid: An IBOTENIC ACID homolog and glutamate agonist. The compound is the defining agonist for the AMPA subtype of glutamate receptors (RECEPTORS, AMPA). It has been used as a radionuclide imaging agent but is more commonly used as an experimental tool in cell biological studies.	2.05	1	0	non-proteinogenic alpha-amino acid
mandelic acid SAMMA: mandelic acid condensation polymer	2.76	2	0	2-hydroxy monocarboxylic acid; benzenes	antibacterial agent; human xenobiotic metabolite
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.	2.71	3	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.	5.65	22	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
1-methylimidazole 1-methyl-1H-imidazole : A 1H-imidazole having a methyl substituent at the N-1 position.	2.05	1	0	imidazoles
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.	8.54	8	0	chlorophenoxyacetic acid; dichlorobenzene	agrochemical; defoliant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; environmental contaminant; phenoxy herbicide; synthetic auxin
2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine: mutagen from fried ground beef; structure given in first source. PhIP : An imidazopyridine that is 1H--imidazo[4,5-b]pyridine which is substituted at positions 1, 2, and 6 by methyl, amino, and phenyl groups, respectively. It is the most abundant of the mutagenic heterocyclic amines found in cooked meat and fish.	2.03	1	0	imidazopyridine; primary amino compound	carcinogenic agent; mutagen
mercaptoethanol Mercaptoethanol: A water-soluble thiol derived from hydrogen sulfide and ethanol. It is used as a reducing agent for disulfide bonds and to protect sulfhydryl groups from oxidation.	2.46	2	0	alkanethiol; primary alcohol	geroprotector
4-aminopyridine [no description available]	2.01	1	0	aminopyridine; aromatic amine	avicide; orphan drug; potassium channel blocker
4-hydroxybenzoic acid hydrazide 4-hydroxybenzoic acid hydrazide: metabolite of nifuroxazide. 4-hydroxybenzohydrazide : A carbohydrazide obtained by formal condensation of the carboxy group of 4-hydroxybenzoic acid with hydrazine.	2.07	1	0	carbohydrazide; phenols
4-nonylphenol 4-nonylphenol: structure in first source; see also record for nonylphenol. 4-nonylphenol : A member of the class of phenols that is phenol which is para-substituted with a nonyl group.	7.41	1	0	phenols	environmental contaminant
5,8,11,14-eicosatetraynoic acid 5,8,11,14-Eicosatetraynoic Acid: A 20-carbon unsaturated fatty acid containing 4 alkyne bonds. It inhibits the enzymatic conversion of arachidonic acid to prostaglandins E(2) and F(2a).	2.05	1	0	long-chain fatty acid
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.	5.96	4	1	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
acetohydroxamic acid acetohydroxamic acid: urease inhibitor. oxime : Compounds of structure R2C=NOH derived from condensation of aldehydes or ketones with hydroxylamine. Oximes from aldehydes may be called aldoximes; those from ketones may be called ketoximes.. N-hydroxyacetimidic acid : A carbohydroximic acid consisting of acetimidic acid having a hydroxy group attached to the imide nitrogen.. acetohydroxamic acid : A member of the class of acetohydroxamic acids that is acetamide in which one of the amino hydrogens has been replaced by a hydroxy group.	1.99	1	0	acetohydroxamic acids; carbohydroximic acid	algal metabolite; EC 3.5.1.5 (urease) inhibitor
alachlor alachlor : An aromatic amide that is N-(2,6-diethylphenyl)acetamide substituted by a methoxymethyl group at at the nitrogen atom while one of the hydrogens of the methyl group has been replaced by a chlorine atom.	7.42	2	0	aromatic amide; monocarboxylic acid amide; organochlorine compound	environmental contaminant; herbicide; xenobiotic
alpha-cyano-4-hydroxycinnamate alpha-cyano-4-hydroxycinnamate: specific inhibitor of pyruvate transport in rat liver mitochondria & human erythrocytes; structure	2.05	1	0
pimagedine pimagedine: diamine oxidase & nitric oxide synthase inhibitor; an advanced glycosylation end product inhibitor; used in the treatment of diabetic complications; structure. aminoguanidine : A one-carbon compound whose unique structure renders it capable of acting as a derivative of hydrazine, guanidine or formamide.	2.41	2	0	guanidines; one-carbon compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor; EC 1.4.3.4 (monoamine oxidase) inhibitor
acetovanillone apocynin : An aromatic ketone that is 1-phenylethanone substituted by a hydroxy group at position 4 and a methoxy group at position 3.	2.49	2	0	acetophenones; aromatic ketone; methyl ketone	antirheumatic drug; EC 1.6.3.1. [NAD(P)H oxidase (H2O2-forming)] inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug; plant metabolite
aristolochic acid i aristolochic acid I: phospholipase A inhibitor. aristolochic acid A : An aristolochic acid that is phenanthrene-1-carboxylic acid that is substituted by a methylenedioxy group at the 3,4 positions, by a methoxy group at position 8, and by a nitro group at position 10. It is the most abundant of the aristolochic acids and is found in almost all Aristolochia (birthworts or pipevines) species. It has been tried in a number of treatments for inflammatory disorders, mainly in Chinese and folk medicine. However, there is concern over their use as aristolochic acid is both carcinogenic and nephrotoxic.	2.01	1	0	aristolochic acids; aromatic ether; C-nitro compound; cyclic acetal; monocarboxylic acid; organic heterotetracyclic compound	carcinogenic agent; metabolite; mutagen; nephrotoxin; toxin
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.	2.55	2	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
atrazine [no description available]	2.77	3	0	chloro-1,3,5-triazine; diamino-1,3,5-triazine	environmental contaminant; herbicide; xenobiotic
azobenzene azobenzene: photosensor molecule known to undergo reversible isomerization from trans to cis on illumination with photons of appropriate wavelength; RN given refers to cpd without isomeric designation; structure. (E)-azobenzene : The (E)-isomer of azobenzene.. (Z)-azobenzene : The (Z)-isomer of azobenzene.. azobenzene : A molecule whose structure comprises two phenyl rings linked by a N=N double bond; the parent compound of the azobenzene class of compounds.	7.31	1	0	azobenzenes
2,2-bis(4-glycidyloxyphenyl)propane 2,2-bis(4-glycidyloxyphenyl)propane: structure	2.66	2	0	diarylmethane
benzethonium Benzethonium: Bactericidal cationic quaternary ammonium surfactant used as a topical anti-infective agent. It is an ingredient in medicaments, deodorants, mouthwashes, etc., and is used to disinfect apparatus, etc., in the food processing and pharmaceutical industries, in surgery, and also as a preservative. The compound is toxic orally as a result of neuromuscular blockade.	2.31	1	0	alkylbenzene
benzo(a)pyrene Benzo(a)pyrene: A potent mutagen and carcinogen. It is a public health concern because of its possible effects on industrial workers, as an environmental pollutant, an as a component of tobacco smoke.. benzo[a]pyrene : An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings.	8.4	7	0	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
berberine [no description available]	1.98	1	0	alkaloid antibiotic; berberine alkaloid; botanical anti-fungal agent; organic heteropentacyclic compound	antilipemic drug; antineoplastic agent; antioxidant; EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor; EC 1.21.3.3 (reticuline oxidase) inhibitor; EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.1.4 (phospholipase A2) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; geroprotector; hypoglycemic agent; metabolite; potassium channel blocker
2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one: from maize extracts; structure given in first source. DIMBOA : A lactol that is DIBOA in which the hydrogen at position 7 is replaced by a methoxy group. It has been isolated from the maize plants.	2.51	2	0	aromatic ether; benzoxazine; cyclic hydroxamic acid; lactol	allelochemical; plant metabolite
bisindolylmaleimide i bisindolylmaleimide I: a bis(indolyl)maleimide	2.02	1	0
caffeine [no description available]	4.06	4	0	purine alkaloid; trimethylxanthine	adenosine A2A receptor antagonist; adenosine receptor antagonist; adjuvant; central nervous system stimulant; diuretic; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; environmental contaminant; food additive; fungal metabolite; geroprotector; human blood serum metabolite; mouse metabolite; mutagen; plant metabolite; psychotropic drug; ryanodine receptor agonist; xenobiotic
carbamazepine Carbamazepine: A dibenzazepine that acts as a sodium channel blocker. It is used as an anticonvulsant for the treatment of grand mal and psychomotor or focal SEIZURES. It may also be used in the management of BIPOLAR DISORDER, and has analgesic properties.. carbamazepine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine carrying a carbamoyl substituent at the azepine nitrogen, used as an anticonvulsant.	2.59	2	0	dibenzoazepine; ureas	analgesic; anticonvulsant; antimanic drug; drug allergen; EC 3.5.1.98 (histone deacetylase) inhibitor; environmental contaminant; glutamate transporter activator; mitogen; non-narcotic analgesic; sodium channel blocker; xenobiotic
carbonyl cyanide m-chlorophenyl hydrazone Carbonyl Cyanide m-Chlorophenyl Hydrazone: A proton ionophore. It is commonly used as an uncoupling agent and inhibitor of photosynthesis because of its effects on mitochondrial and chloroplast membranes.. CCCP : A member of the class of monochlorobenzenes that is benzene substituted by 2-(1,3-dinitrilopropan-2-ylidene)hydrazinyl and chloro groups at positions 1 and 3, respectively. It is a mitochondrial depolarizing agent that induces reactive oxygen species mediated cell death.	4.9	1	1	hydrazone; monochlorobenzenes; nitrile	antibacterial agent; geroprotector; ionophore
cetyltrimethylammonium ion Cetrimonium: Cetyltrimethylammonium compound whose salts and derivatives are used primarily as topical antiseptics.. cetyltrimethylammonium ion : A quaternary ammonium ion in which the substituents on nitrogen are one hexadecyl and three methyl groups.	3.79	8	0	quaternary ammonium ion
chloral hydrate [no description available]	2.59	2	0	aldehyde hydrate; ethanediol; organochlorine compound	general anaesthetic; mouse metabolite; sedative; xenobiotic
chloroquine Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.	7.47	2	0	aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug
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.	1.98	1	0	organochlorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; phenothiazine antipsychotic drug
chlorpyrifos Chlorpyrifos: An organothiophosphate cholinesterase inhibitor that is used as an insecticide and as an acaricide.. chlorpyrifos : An organic thiophosphate that is O,O-diethyl hydrogen phosphorothioate in which the hydrogen of the hydroxy group has been replaced by a 3,5,6-trichloropyridin-2-yl group.	2.52	2	0	chloropyridine; organic thiophosphate	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; environmental contaminant; insecticide; xenobiotic
ciprofloxacin Ciprofloxacin: A broad-spectrum antimicrobial carboxyfluoroquinoline.. ciprofloxacin : A quinolone that is quinolin-4(1H)-one bearing cyclopropyl, carboxylic acid, fluoro and piperazin-1-yl substituents at positions 1, 3, 6 and 7, respectively.	7.83	3	0	aminoquinoline; cyclopropanes; fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone; zwitterion	antibacterial drug; antiinfective agent; antimicrobial agent; DNA synthesis inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; environmental contaminant; topoisomerase IV inhibitor; xenobiotic
clofibrate angiokapsul: contains clofibrate & insoitolnicotinate	3.04	1	0	aromatic ether; ethyl ester; monochlorobenzenes	anticholesteremic drug; antilipemic drug; geroprotector; PPARalpha agonist
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.	2.47	2	0	cresol	Escherichia coli metabolite; human metabolite; uremic toxin
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.	3.48	2	0	acyclic desferrioxamine	bacterial metabolite; ferroptosis inhibitor; iron chelator; siderophore
methylene bromide methylene bromide: RN given refers to parent cpd. dibromomethane : A member of the class of bromomethanes that is methane substituted by two bromo groups. It is produced by marine algae.	2.11	1	0	bromohydrocarbon; bromomethanes	algal metabolite; marine metabolite
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.	2.06	1	0	diester; phthalate ester	EC 3.2.1.20 (alpha-glucosidase) inhibitor; environmental contaminant; metabolite; plasticiser; teratogenic agent
dichlobanil 2,6-dichlorobenzonitrile : A nitrile that is benzonitrile which is substituted by chlorines at positions 2 and 6. A cellulose synthesis inhibitor, it is used as a pre-emergent and early post-emergent herbicide.	2.54	2	0	dichlorobenzene; nitrile	agrochemical; cellulose synthesis inhibitor; environmental contaminant; herbicide; xenobiotic
ddt 1,1-bis(p-chlorophenyl)-2,2,2-trichloroethane: structure in first source	3.74	3	0	benzenoid aromatic compound; chlorophenylethane; monochlorobenzenes; organochlorine insecticide	bridged diphenyl acaricide; carcinogenic agent; endocrine disruptor; persistent organic pollutant
diphenhydramine Diphenhydramine: A histamine H1 antagonist used as an antiemetic, antitussive, for dermatoses and pruritus, for hypersensitivity reactions, as a hypnotic, an antiparkinson, and as an ingredient in common cold preparations. It has some undesired antimuscarinic and sedative effects.. diphenhydramine : An ether that is the benzhydryl ether of 2-(dimethylamino)ethanol. It is a H1-receptor antagonist used as a antipruritic and antitussive drug.. antitussive : An agent that suppresses cough. Antitussives have a central or a peripheral action on the cough reflex, or a combination of both. Compare with expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing, and mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration.	4.9	1	1	ether; tertiary amino compound	anti-allergic agent; antidyskinesia agent; antiemetic; antiparkinson drug; antipruritic drug; antitussive; H1-receptor antagonist; local anaesthetic; muscarinic antagonist; oneirogen; sedative
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.	2.48	2	0	organic cation
benzophenone benzophenone : The simplest member of the class of benzophenones, being formaldehyde in which both hydrogens are replaced by phenyl groups.	2.08	1	0	benzophenones	photosensitizing agent; plant metabolite
disulfiram [no description available]	2.11	1	0	organic disulfide; organosulfur acaricide	angiogenesis inhibitor; antineoplastic agent; apoptosis inducer; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; EC 3.1.1.1 (carboxylesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; ferroptosis inducer; fungicide; NF-kappaB inhibitor
diuron Diuron: A pre-emergent herbicide.. diuron : A member of the class of 3-(3,4-substituted-phenyl)-1,1-dimethylureas that is urea in which both of the hydrogens attached to one nitrogen are substituted by methyl groups, and one of the hydrogens attached to the other nitrogen is substituted by a 3,4-dichlorophenyl group.	2.75	3	0	3-(3,4-substituted-phenyl)-1,1-dimethylurea; dichlorobenzene	environmental contaminant; mitochondrial respiratory-chain inhibitor; photosystem-II inhibitor; urea herbicide; xenobiotic
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.	7.6	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
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.	2.07	1	0
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.	9.37	5	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.	2.79	3	0	alkane-alpha,omega-diamine	GABA agonist
flumequine flumequine: structure. flumequine : A racemate comprising equimolar amounts of R- and S-flumequine. A broad-spectrum antibiotic, formerly used in veterinary medicine for stock breeding and treatment of aquacultures.. 9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid : A member of the class of pyridoquinolines that is 1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline carrying additional carboxy, methyl and fluoro substituents at positions 2, 5 and 9 respectively.	7.08	1	0	3-oxo monocarboxylic acid; organofluorine compound; pyridoquinoline; quinolone antibiotic
fluorouracil Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.	2.06	1	0	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
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.	2.41	1	0	(trifluoromethyl)benzenes; aromatic ether; secondary amino compound
furosemide Furosemide: A benzoic-sulfonamide-furan. It is a diuretic with fast onset and short duration that is used for EDEMA and chronic RENAL INSUFFICIENCY.. furosemide : A chlorobenzoic acid that is 4-chlorobenzoic acid substituted by a (furan-2-ylmethyl)amino and a sulfamoyl group at position 2 and 5 respectively. It is a diuretic used in the treatment of congestive heart failure.	4.68	25	0	chlorobenzoic acid; furans; sulfonamide	environmental contaminant; loop diuretic; xenobiotic
gentamicin Gentamicins: A complex of closely related aminoglycosides obtained from MICROMONOSPORA purpurea and related species. They are broad-spectrum antibiotics, but may cause ear and kidney damage. They act to inhibit PROTEIN BIOSYNTHESIS.	2.02	1	0
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.	2.05	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.	4.36	5	0	dialdehyde	cross-linking reagent; disinfectant; fixative
glyphosate glyphosate: active cpd in herbicidal formulation Roundup; inhibits EC 2.5.1.19, 5-enolpyruvylshikimate-3-phosphate synthase; structure. glyphosate : A phosphonic acid resulting from the formal oxidative coupling of the methyl group of methylphosphonic acid with the amino group of glycine. It is one of the most commonly used herbicides worldwide, and the only one to target the enzyme 5-enolpyruvyl-3-shikimate phosphate synthase (EPSPS).	2.53	2	0	glycine derivative; phosphonic acid	agrochemical; EC 2.5.1.19 (3-phosphoshikimate 1-carboxyvinyltransferase) inhibitor; herbicide
gossypol Gossypol: A dimeric sesquiterpene found in cottonseed (GOSSYPIUM). The (-) isomer is active as a male contraceptive (CONTRACEPTIVE AGENTS, MALE) whereas toxic symptoms are associated with the (+) isomer.	7.43	2	0
guaifenesin Guaifenesin: An expectorant that also has some muscle relaxing action. It is used in many cough preparations.	5.3	17	0	methoxybenzenes
guanidine Guanidine: A strong organic base existing primarily as guanidium ions at physiological pH. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed) It is also used in the treatment of myasthenia and as a fluorescent probe in HPLC.. guanidine : An aminocarboxamidine, the parent compound of the guanidines.	2.41	1	0	carboxamidine; guanidines; one-carbon compound
haloperidol Haloperidol: A phenyl-piperidinyl-butyrophenone that is used primarily to treat SCHIZOPHRENIA and other PSYCHOSES. It is also used in schizoaffective disorder, DELUSIONAL DISORDERS, ballism, and TOURETTE SYNDROME (a drug of choice) and occasionally as adjunctive therapy in INTELLECTUAL DISABILITY and the chorea of HUNTINGTON DISEASE. It is a potent antiemetic and is used in the treatment of intractable HICCUPS. (From AMA Drug Evaluations Annual, 1994, p279). haloperidol : A compound composed of a central piperidine structure with hydroxy and p-chlorophenyl substituents at position 4 and an N-linked p-fluorobutyrophenone moiety.	7.7	35	0	aromatic ketone; hydroxypiperidine; monochlorobenzenes; organofluorine compound; tertiary alcohol	antidyskinesia agent; antiemetic; dopaminergic antagonist; first generation antipsychotic; serotonergic antagonist
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	7.89	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
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.	3.69	8	0	secondary alcohol; secondary fatty alcohol	protic solvent
juglone juglone: structure. juglone : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogen at position 5 has been replaced by a hydroxy group. A plant-derived 1,4-naphthoquinone with confirmed antibacterial and antitumor activities.	2.02	1	0	hydroxy-1,4-naphthoquinone	geroprotector; herbicide; reactive oxygen species generator
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.	2.05	1	0	6-aminopurines; furans	cytokinin; geroprotector
3-phenyllactic acid 3-phenyllactic acid: alpha-hydroxy analog of phenylalanine; RN given refers to cpd without isomeric designation. 3-phenyllactic acid : A 2-hydroxy monocarboxylic acid that is lactic acid in which one of the methyl hydrogens is substituted by a phenyl group.	2.11	1	0	2-hydroxy monocarboxylic acid	human metabolite
lithium hydroxide lithium hydroxide: used for tryptophan determinations in proteins & foods; RN given refers to cpd with MF of Li-OH	2.25	1	0	alkali metal hydroxide
losartan Losartan: An antagonist of ANGIOTENSIN TYPE 1 RECEPTOR with antihypertensive activity due to the reduced pressor effect of ANGIOTENSIN II.. losartan : A biphenylyltetrazole where a 1,1'-biphenyl group is attached at the 5-position and has an additional trisubstituted imidazol-1-ylmethyl group at the 4'-position	7.31	1	0	biphenylyltetrazole; imidazoles	angiotensin receptor antagonist; anti-arrhythmia drug; antihypertensive agent; endothelin receptor antagonist
metformin Metformin: A biguanide hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. Metformin improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. (From Martindale, The Extra Pharmacopoeia, 30th ed, p289). metformin : A member of the class of guanidines that is biguanide the carrying two methyl substituents at position 1.	2.59	2	0	guanidines	environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic
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.	3.35	1	0	benzenes; diarylmethane; ketone; tertiary amino compound
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.	5.38	52	0	benzoate ester; methyl ester; salicylates	flavouring agent; insect attractant; metabolite
methyl methanesulfonate [no description available]	2.31	1	0	methanesulfonate ester	alkylating agent; apoptosis inducer; carcinogenic agent; genotoxin; mutagen
metolachlor metolachlor: structure given in first source. metolachlor : A racemate that consists of equimolar amounts of (R)- and (S)-metolachlor.. 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide : An organochlorine compound that is 2-chloroacetamide substituted by a (2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl) group at the nitrogen atom.	2.01	1	0	aromatic amide; benzenes; ether; organochlorine compound
minoxidil Minoxidil: A potent direct-acting peripheral vasodilator (VASODILATOR AGENTS) that reduces peripheral resistance and produces a fall in BLOOD PRESSURE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p371). minoxidil : A pyrimidine N-oxide that is pyrimidine-2,4-diamine 3-oxide substituted by a piperidin-1-yl group at position 6.	7.6	1	0	dialkylarylamine; tertiary amino compound
nevirapine Nevirapine: A potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV INFECTIONS and AIDS.. nevirapine : A dipyridodiazepine that is 5,11-dihydro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepine which is substituted by methyl, oxo, and cyclopropyl groups at positions 4, 6, and 11, respectively. A non-nucleoside reverse transcriptase inhibitor with activity against HIV-1, it is used in combination with other antiretrovirals for the treatment of HIV infection.	2.07	1	0	cyclopropanes; dipyridodiazepine	antiviral drug; HIV-1 reverse transcriptase inhibitor
norfloxacin Norfloxacin: A synthetic fluoroquinolone (FLUOROQUINOLONES) with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin inhibits bacterial DNA GYRASE.. norfloxacin : A quinolinemonocarboxylic acid with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase.	7.6	1	0	fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antibacterial drug; DNA synthesis inhibitor; environmental contaminant; xenobiotic
ofloxacin Ofloxacin: A synthetic fluoroquinolone antibacterial agent that inhibits the supercoiling activity of bacterial DNA GYRASE, halting DNA REPLICATION.. 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid : An oxazinoquinoline that is 2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinolin-7-one substituted by methyl, carboxy, fluoro, and 4-methylpiperazin-1-yl groups at positions 3, 6, 9, and 10, respectively.. ofloxacin : A racemate comprising equimolar amounts of levofloxacin and dextrofloxacin. It is a synthetic fluoroquinolone antibacterial agent which inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication.	7.31	1	0	3-oxo monocarboxylic acid; N-arylpiperazine; N-methylpiperazine; organofluorine compound; oxazinoquinoline
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).	8.75	10	0	1,4-benzoquinones	cofactor; human xenobiotic metabolite; mouse metabolite
4-chlorophenol 4-chlorophenol: used as a root canal irrigant. 4-chlorophenol : A monochlorophenol substituted at the pare position by a chlorine atom.	7.6	1	0	monochlorophenol
pargyline Pargyline: A monoamine oxidase inhibitor with antihypertensive properties.	2.08	1	0	aromatic amine
patulin Patulin: 4-Hydroxy-4H-furo(3,2-c)pyran-2(6H)-one. A mycotoxin produced by several species of Aspergillus and Penicillium. It is found in unfermented apple and grape juice and field crops. It has antibiotic properties and has been shown to be carcinogenic and mutagenic and causes chromosome damage in biological systems.. patulin : A furopyran and lactone that is (2H-pyran-3(6H)-ylidene)acetic acid which is substituted by hydroxy groups at positions 2 and 4 and in which the hydroxy group at position 4 has condensed with the carboxy group to give the corresponding bicyclic lactone. A mycotoxin produced by several species of Aspergillus and Penicillium, it has antibiotic properties but has been shown to be carcinogenic and mutagenic.	7.6	1	0	furopyran; gamma-lactone; lactol	antimicrobial agent; Aspergillus metabolite; carcinogenic agent; mutagen; mycotoxin; Penicillium metabolite
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'.	2.02	1	0	aromatic amine; monomethoxyflavone	EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector
phenolsulfonphthalein Phenolsulfonphthalein: Red dye, pH indicator, and diagnostic aid for determination of renal function. It is used also for studies of the gastrointestinal and other systems.. phenol red : 3H-2,1-Benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 4-hydroxyphenyl groups. A pH indicator changing colour from yellow below pH 6.8 to bright pink above pH 8.2, it is commonly used as an indicator in cell cultures and in home swimming pool test kits. It is also used in the (now infrequently performed) phenolsulfonphthalein (PSP) test for estimation of overall blood flow through the kidney.	2.96	4	0	2,1-benzoxathiole; arenesulfonate ester; phenols; sultone	acid-base indicator; diagnostic agent; two-colour indicator
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.	1.98	1	0	potassium salt	expectorant; radical scavenger
probucol Probucol: A drug used to lower LDL and HDL cholesterol yet has little effect on serum-triglyceride or VLDL cholesterol. (From Martindale, The Extra Pharmacopoeia, 30th ed, p993).. probucol : A dithioketal that is propane-2,2-dithiol in which the hydrogens attached to both sulfur atoms are replaced by 3,5-di-tert-butyl-4-hydroxyphenyl groups. An anticholesteremic drug with antioxidant and anti-inflammatory properties, it is used to treat high levels of cholesterol in blood.	3.04	1	0	dithioketal; polyphenol	anti-inflammatory drug; anticholesteremic drug; antilipemic drug; antioxidant; cardiovascular drug
propazine propazine: relatively non-toxic triazine herbicide; minor descriptor (75-82); online & Index Medicus search TRIAZINES (75-82). propazine : A diamino-1,3,5-triazine that is N,N'-di(propan-2-yl)-1,3,5-triazine-2,4-diamine substituted by a chloro group at position 6.	2.11	1	0	chloro-1,3,5-triazine; diamino-1,3,5-triazine	environmental contaminant; herbicide; xenobiotic
propidium Propidium: Quaternary ammonium analog of ethidium; an intercalating dye with a specific affinity to certain forms of DNA and, used as diiodide, to separate them in density gradients; also forms fluorescent complexes with cholinesterase which it inhibits.	2.07	1	0	phenanthridines; quaternary ammonium ion	fluorochrome; intercalator
propyl gallate Propyl Gallate: Antioxidant for foods, fats, oils, ethers, emulsions, waxes, and transformer oils.	2.07	1	0	trihydroxybenzoic acid
protoporphyrin ix protoporphyrin IX: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7685. protoporphyrin : A cyclic tetrapyrrole that consists of porphyrin bearing four methyl substituents at positions 3, 8, 13 and 17, two vinyl substituents at positions 7 and 12 and two 2-carboxyethyl substituents at positions 2 and 18. The parent of the class of protoporphyrins.	2	1	0
pyrimethamine Maloprim: contains above 2 cpds	1.96	1	0	aminopyrimidine; monochlorobenzenes	antimalarial; antiprotozoal drug; EC 1.5.1.3 (dihydrofolate reductase) inhibitor
resorcinol resorcinol: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7951. resorcinol : A benzenediol that is benzene dihydroxylated at positions 1 and 3.	1.93	1	0	benzenediol; phenolic donor; resorcinols	erythropoietin inhibitor; sensitiser
saccharin Saccharin: Flavoring agent and non-nutritive sweetener.. saccharin : A 1,2-benzisothiazole having a keto-group at the 3-position and two oxo substituents at the 1-position. It is used as an artificial sweetening agent.	2.1	1	0	1,2-benzisothiazole; N-sulfonylcarboxamide	environmental contaminant; sweetening agent; xenobiotic
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.	1.92	1	0	benzodioxoles	flavouring agent; insecticide; metabolite; plant metabolite
stearic acid octadecanoic acid : A C18 straight-chain saturated fatty acid component of many animal and vegetable lipids. As well as in the diet, it is used in hardening soaps, softening plastics and in making cosmetics, candles and plastics.	2.05	1	0	long-chain fatty acid; saturated fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; human metabolite; plant metabolite
vorinostat Vorinostat: A hydroxamic acid and anilide derivative that acts as a HISTONE DEACETYLASE inhibitor. It is used in the treatment of CUTANEOUS T-CELL LYMPHOMA and SEZARY SYNDROME.. vorinostat : A dicarboxylic acid diamide comprising suberic (octanedioic) acid coupled to aniline and hydroxylamine. A histone deacetylase inhibitor, it is marketed under the name Zolinza for the treatment of cutaneous T cell lymphoma (CTCL).	2.02	1	0	dicarboxylic acid diamide; hydroxamic acid	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor
sulfamerazine [no description available]	2.6	1	0	pyrimidines; sulfonamide antibiotic; sulfonamide	antiinfective agent; drug allergen
sulfamethazine Sulfamethazine: A sulfanilamide anti-infective agent. It has a spectrum of antimicrobial action similar to other sulfonamides.. sulfamethazine : A sulfonamide consisting of pyrimidine with methyl substituents at the 4- and 6-positions and a 4-aminobenzenesulfonamido group at the 2-position.	2.15	1	0	pyrimidines; sulfonamide antibiotic; sulfonamide	antibacterial drug; antiinfective agent; antimicrobial agent; carcinogenic agent; drug allergen; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; ligand; xenobiotic
sulfamethoxazole Sulfamethoxazole: A bacteriostatic antibacterial agent that interferes with folic acid synthesis in susceptible bacteria. Its broad spectrum of activity has been limited by the development of resistance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p208). sulfamethoxazole : An isoxazole (1,2-oxazole) compound having a methyl substituent at the 5-position and a 4-aminobenzenesulfonamido group at the 3-position.	2.63	2	0	isoxazoles; substituted aniline; sulfonamide antibiotic; sulfonamide	antibacterial agent; antiinfective agent; antimicrobial agent; drug allergen; EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; epitope; P450 inhibitor; xenobiotic
tegafur [no description available]	2.41	1	0	organohalogen compound; pyrimidines
nikethamide Nikethamide: A central nervous system stimulant. It was formerly used in the treatment of barbiturate overdose but is now considered to be of no value for such purposes and may be dangerous. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1229)	2.13	1	0	pyridinecarboxamide
bromoform bromoform: structure	2.11	1	0	bromohydrocarbon; bromomethanes
triclosan [no description available]	3.78	2	0	aromatic ether; dichlorobenzene; monochlorobenzenes; phenols	antibacterial agent; antimalarial; drug allergen; EC 1.3.1.9 [enoyl-[acyl-carrier-protein] reductase (NADH)] inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; fungicide; persistent organic pollutant; xenobiotic
trientine Trientine: An ethylenediamine derivative used as stabilizer for EPOXY RESINS, as ampholyte for ISOELECTRIC FOCUSING and as chelating agent for copper in HEPATOLENTICULAR DEGENERATION.. TETA : An azamacrocyle in which four nitrogen atoms at positions 1, 4, 8 and 11 of a fouteen-membered ring are each substituted with a carboxymethyl group.. 2,2,2-tetramine : A polyazaalkane that is decane in which the carbon atoms at positions 1, 4, 7 and 10 are replaced by nitrogens.	2.96	3	0	polyazaalkane; tetramine	copper chelator
trifluoperazine [no description available]	2.41	2	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
trigonelline trigonelline: in hydra among other organisms; RN given refers to hydroxide inner salt; structure. N-methylnicotinic acid : A pyridinium ion consisting of nicotinic acid having a methyl substituent on the pyridine nitrogen.. N-methylnicotinate : An iminium betaine that is the conjugate base of N-methylnicotinic acid, arising from deprotonation of the carboxy group.	2.15	1	0	alkaloid; iminium betaine	food component; human urinary metabolite; plant metabolite
tyramine [no description available]	2.15	1	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]	2.07	1	0	carbamate ester	fungal metabolite; mutagen
w 7 W 7: RN given refers to parent cpd; structure; calmodulin antagonist	2.71	3	0
zinc chloride zinc chloride: RN given refers to parent cpd. zinc dichloride : A compound of zinc and chloride ions in the ratio 1:2. It exists in four crystalline forms, in each of which the Zn(2+) ions are trigonal planar coordinated to four chloride ions.	2.6	1	0	inorganic chloride; zinc molecular entity	astringent; disinfectant; EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor; Lewis acid
corticosterone [no description available]	1.99	1	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
prednisolone Prednisolone: A glucocorticoid with the general properties of the corticosteroids. It is the drug of choice for all conditions in which routine systemic corticosteroid therapy is indicated, except adrenal deficiency states.. prednisolone : A glucocorticoid that is prednisone in which the oxo group at position 11 has been reduced to the corresponding beta-hydroxy group. It is a drug metabolite of prednisone.	1.97	1	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antineoplastic agent; drug metabolite; environmental contaminant; immunosuppressive agent; xenobiotic
estriol hormonin: estrogen replacement; each tablet contains 600 ug micronized 17beta-estradiol, 270 ug estriol and 1.4 mg estrone. chlorapatite : A phosphate mineral with the formula Ca5(PO4)3Cl.	1.96	1	0	16alpha-hydroxy steroid; 17beta-hydroxy steroid; 3-hydroxy steroid	estrogen; human metabolite; human xenobiotic metabolite; mouse metabolite
sorbitol D-glucitol : The D-enantiomer of glucitol (also known as D-sorbitol).	4.62	4	0	glucitol	cathartic; Escherichia coli metabolite; food humectant; human metabolite; laxative; metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite; sweetening agent
piperonyl butoxide [no description available]	2.43	2	0	benzodioxoles	pesticide synergist
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.	1.97	1	0	4-hydroxyproline; L-alpha-amino acid zwitterion	human metabolite; mouse metabolite; plant metabolite
thyroxine Thyroxine: The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (MONOIODOTYROSINE) and the coupling of iodotyrosines (DIIODOTYROSINE) in the THYROGLOBULIN. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form TRIIODOTHYRONINE which exerts a broad spectrum of stimulatory effects on cell metabolism.. thyroxine : An iodothyronine compound having iodo substituents at the 3-, 3'-, 5- and 5'-positions.	3.04	1	0	2-halophenol; iodophenol; L-phenylalanine derivative; non-proteinogenic L-alpha-amino acid; thyroxine zwitterion; thyroxine	antithyroid drug; human metabolite; mouse metabolite; thyroid hormone
estrone Hydroxyestrones: Estrone derivatives substituted with one or more hydroxyl groups in any position. They are important metabolites of estrone and other estrogens.	1.96	1	0	17-oxo steroid; 3-hydroxy steroid; phenolic steroid; phenols	antineoplastic agent; bone density conservation agent; estrogen; human metabolite; mouse metabolite
oxandrolone Oxandrolone: A synthetic hormone with anabolic and androgenic properties.	3.04	1	0	17beta-hydroxy steroid; 3-oxo steroid; anabolic androgenic steroid; oxa-steroid	anabolic agent; androgen
2-acetylaminofluorene 2-Acetylaminofluorene: A hepatic carcinogen whose mechanism of activation involves N-hydroxylation to the aryl hydroxamic acid followed by enzymatic sulfonation to sulfoxyfluorenylacetamide. It is used to study the carcinogenicity and mutagenicity of aromatic amines.	1.98	1	0	2-acetamidofluorenes	antimitotic; carcinogenic agent; epitope; mutagen
dimethylphenylpiperazinium iodide Dimethylphenylpiperazinium Iodide: A selective nicotinic cholinergic agonist used as a research tool. DMPP activates nicotinic receptors in autonomic ganglia but has little effect at the neuromuscular junction.	2.17	1	0	N-arylpiperazine; organic iodide salt; piperazinium salt; quaternary ammonium salt	nicotinic acetylcholine receptor agonist
biguanides Biguanides: Derivatives of biguanide (the structure formula HN(C(NH)NH2)2) that are primarily used as oral HYPOGLYCEMIC AGENTS for the treatment of DIABETES MELLITUS, TYPE 2 and PREDIABETES.. biguanides : A class of oral hypoglycemic drugs used for diabetes mellitus or prediabetes treatment. They have a structure based on the 2-carbamimidoylguanidine skeleton.	3.07	1	0	guanidines
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.	8.51	2	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
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.	8.08	4	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.	2.53	2	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.	2.05	1	0	ortho-fused polycyclic arene; tetraphenes
4-nitroquinoline-1-oxide 4-nitroquinoline N-oxide : A quinoline N-oxide carrying a nitro substituent at position 4.	2.38	2	0	C-nitro compound; quinoline N-oxide	carcinogenic agent
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	7.41	1	0	C-nitro compound; carboxamide; diol; organochlorine compound	antibacterial drug; antimicrobial agent; Escherichia coli metabolite; geroprotector; Mycoplasma genitalium metabolite; protein synthesis inhibitor
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.	2.58	2	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.	2.52	2	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.	4.93	8	1	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
benzyltrimethylammonium benzyltrimethylammonium: RN given refers to parent cpd	2.31	1	0
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.	3.79	3	0	pseudohalide anion	EC 1.9.3.1 (cytochrome c oxidase) inhibitor
sulfamic acid sulfamic acid: standard in alkalimetry; RN given refers to parent cpd; structure. sulfamic acid : The simplest of the sulfamic acids consisting of a single sulfur atom covalently bound by single bonds to hydroxy and amino groups and by double bonds to two oxygen atoms.	7.6	1	0	sulfamic acids
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	10.76	344	0	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
ethinyl estradiol Ethinyl Estradiol: A semisynthetic alkylated ESTRADIOL with a 17-alpha-ethinyl substitution. It has high estrogenic potency when administered orally, and is often used as the estrogenic component in ORAL CONTRACEPTIVES.. 17alpha-ethynylestradiol : A 3-hydroxy steroid that is estradiol substituted by a ethynyl group at position 17. It is a xenoestrogen synthesized from estradiol and has been shown to exhibit high estrogenic potency on oral administration.	2.48	2	0	17-hydroxy steroid; 3-hydroxy steroid; terminal acetylenic compound	xenoestrogen
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	2.71	3	0	adenosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite; human metabolite
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.	4.05	14	0	tetrachlorophenol	xenobiotic metabolite
uridine [no description available]	2.06	1	0	uridines	drug metabolite; fundamental metabolite; human metabolite
galactose galactopyranose : The pyranose form of galactose.	5.33	17	0	D-galactose; galactopyranose	Escherichia coli metabolite; mouse metabolite
benzoxazolone benzoxazolone: RN given refers to parent cpd; structure. 2-benzoxazolinone : A member of the class of benzoxazoles that is 2,3-dihydro-1,3-benzoxazole carrying an oxo group at position 2.	2.11	1	0	benzoxazole	allelochemical; phytoalexin
levodopa Levodopa: The naturally occurring form of DIHYDROXYPHENYLALANINE and the immediate precursor of DOPAMINE. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to DOPAMINE. It is used for the treatment of PARKINSONIAN DISORDERS and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system.. L-dopa : An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease	3.03	4	0	amino acid zwitterion; dopa; L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	allelochemical; antidyskinesia agent; antiparkinson drug; dopaminergic agent; hapten; human metabolite; mouse metabolite; neurotoxin; plant growth retardant; plant metabolite; prodrug
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.	3.48	8	0	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
tributyrin tributyrin: structure. tributyrin : A triglyceride obtained by formal acylation of the three hydroxy groups of glycerol by butyric acid.	2.07	1	0	butyrate ester; triglyceride	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor; prodrug; protective agent
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.	2.71	3	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.	6.05	21	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
methylene blue Methylene Blue: A compound consisting of dark green crystals or crystalline powder, having a bronze-like luster. Solutions in water or alcohol have a deep blue color. Methylene blue is used as a bacteriologic stain and as an indicator. It inhibits GUANYLATE CYCLASE, and has been used to treat cyanide poisoning and to lower levels of METHEMOGLOBIN.. methylene blue : An organic chloride salt having 3,7-bis(dimethylamino)phenothiazin-5-ium as the counterion. A commonly used dye that also exhibits antioxidant, antimalarial, antidepressant and cardioprotective properties.	5.33	46	0	organic chloride salt	acid-base indicator; antidepressant; antimalarial; antimicrobial agent; antioxidant; cardioprotective agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 4.6.1.2 (guanylate cyclase) inhibitor; fluorochrome; histological dye; neuroprotective agent; physical tracer
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.	4.05	10	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.	2.15	1	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.	3.18	5	0	methanesulfonate ester	alkylating agent; antineoplastic agent; carcinogenic agent; genotoxin; mutagen; teratogenic agent
aniline [no description available]	2.49	2	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.	2.08	1	0	2,2-dialkylglycine zwitterion; 2,2-dialkylglycine
androstenedione Androstenedione: A delta-4 C19 steroid that is produced not only in the TESTIS, but also in the OVARY and the ADRENAL CORTEX. Depending on the tissue type, androstenedione can serve as a precursor to TESTOSTERONE as well as ESTRONE and ESTRADIOL.. androst-4-ene-3,17-dione : A 3-oxo Delta(4)-steroid that is androst-4-ene substituted by oxo groups at positions 3 and 17. It is a steroid hormone synthesized in the adrenal glands and gonads.	1.98	1	0	17-oxo steroid; 3-oxo-Delta(4) steroid; androstanoid	androgen; Daphnia magna metabolite; human metabolite; mouse metabolite
carbaryl Carbaryl: A carbamate insecticide and parasiticide. It is a potent anticholinesterase agent belonging to the carbamate group of reversible cholinesterase inhibitors. It has a particularly low toxicity from dermal absorption and is used for control of head lice in some countries.. carbaryl : A carbamate ester obtained by the formal condensation of 1-naphthol with methylcarbamic acid.	2.25	1	0	carbamate ester; naphthalenes	acaricide; agrochemical; carbamate insecticide; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; plant growth retardant
lactose Lactose: A disaccharide of GLUCOSE and GALACTOSE in human and cow milk. It is used in pharmacy for tablets, in medicine as a nutrient, and in industry.. lactose : A glycosylglucose disaccharide, found most notably in milk, that consists of D-galactose and D-glucose fragments bonded through a beta-1->4 glycosidic linkage. The glucose fragment can be in either the alpha- or beta-pyranose form, whereas the galactose fragment can only have the beta-pyranose form.. beta-lactose : The beta-anomer of lactose.	3.54	8	0	lactose
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.	4.88	11	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.	2.21	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.	7.18	38	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
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.	3.23	6	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.	2.41	1	0	diether; tertiary amino compound; tetracarboxylic acid	chelator
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.	8.43	7	0	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
dimethylformamide Dimethylformamide: A formamide in which the amino hydrogens are replaced by methyl groups.. N,N-dimethylformamide : A member of the class of formamides that is formamide in which the amino hydrogens are replaced by methyl groups.	3.5	8	0	formamides; volatile organic compound	geroprotector; hepatotoxic agent; polar aprotic solvent
mannitol [no description available]	7.96	4	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.	2.69	3	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
4-toluenesulfonamide 4-toluenesulfonamide: RN given refers to parent cpd. toluene-4-sulfonamide : A sulfonamide that is benzenesulfonamide bearing a methyl group at position 4.	2.31	1	0	sulfonamide
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.	7.99	4	0	amino acid zwitterion; histidine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
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.	3.3	4	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.	2.25	1	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.	2.41	1	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.	2.79	3	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.	10.39	10	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
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.	7.95	4	0	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
ethylene Plastipore: high density polyethylene sponge biocompatible material; used as posts in dental bridges	5.1	41	0	alkene; gas molecular entity	plant hormone; refrigerant
acetylene [no description available]	2.15	1	0	alkyne; gas molecular entity; terminal acetylenic compound
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.	2.13	1	0	iodomethanes; methyl halides	fumigant insecticide
propane Propane: A three carbon alkane with the formula H3CCH2CH3.	2.49	2	0	alkane; gas molecular entity	food propellant
ethylamine ethylamine : A two-carbon primary aliphatic amine.	2.25	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.	2.06	1	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.	2.52	2	0	chloromethanes; volatile organic compound	carcinogenic agent; polar aprotic solvent; refrigerant
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.	7.4	2	0	gas molecular entity; oxacycle; saturated organic heteromonocyclic parent	allergen; mouse metabolite; mutagen
propylene oxide propylene oxide: structure. 1,2-epoxypropane : An epoxide that is oxirane substituted by a methyl group at position 2.	2.06	1	0	epoxide
tetramethylammonium tetramethylammonium: RN given refers to parent cpd. tetramethylammonium : The simplest quaternary ammonium cation, comprising a central nitrogen linked to four methyl groups.	3.97	13	0	quaternary ammonium ion
tetramethylsilane [no description available]	2.06	1	0	organosilicon compound	NMR chemical shift reference compound
trichloroacetaldehyde trichloroacetaldehyde : An organochlorine compound that consists of acetaldehyde where all the methyl hydrogens are replaced by chloro groups.	2.11	1	0	aldehyde; organochlorine compound	mouse metabolite
tert-butylhydroperoxide tert-Butylhydroperoxide: A direct-acting oxidative stress-inducing agent used to examine the effects of oxidant stress on Ca(2+)-dependent signal transduction in vascular endothelial cells. It is also used as a catalyst in polymerization reactions and to introduce peroxy groups into organic molecules.. tert-butyl hydroperoxide : An alkyl hydroperoxide in which the alkyl group is tert-butyl. It is widely used in a variety of oxidation processes.	6.96	1	0	alkyl hydroperoxide	antibacterial agent; oxidising agent
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.	2.6	1	0	monocarboxylic acid; organochlorine compound	carcinogenic agent; metabolite; mouse metabolite
trifluoroacetic acid Trifluoroacetic Acid: A very strong halogenated derivative of acetic acid. It is used in acid catalyzed reactions, especially those where an ester is cleaved in peptide synthesis.. trifluoroacetic acid : A monocarboxylic acid that is the trifluoro derivative of acetic acid.	2.7	3	0	fluoroalkanoic acid	human xenobiotic metabolite; NMR chemical shift reference compound; reagent
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.	4.69	8	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.	5.12	14	0	benzenes; piperidines	anaesthetic; neurotoxin; NMDA receptor antagonist; psychotropic drug
quinic acid (-)-quinic acid : The (-)-enantiomer of quinic acid.	3.24	6	0
3-mercaptopropionic acid 3-Mercaptopropionic Acid: An inhibitor of glutamate decarboxylase. It decreases the GAMMA-AMINOBUTYRIC ACID concentration in the brain, thereby causing convulsions.. 3-mercaptopropanoic acid : A mercaptopropanoic acid that is propanoic acid carrying a sulfanyl group at position 3.	2.31	1	0	mercaptopropanoic acid	algal metabolite
tris(2-butoxyethyl) phosphate tris(2-butoxyethyl) phosphate: inhibitor of drug-protein binding; present in stoppers of blood sample 'vacutainers'. tris(2-butoxyethyl) phosphate : A trialkyl phosphate in which the alkyl group specified is 2-butoxyethyl.	2.1	1	0	trialkyl phosphate	environmental contaminant; flame retardant
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.	6.78	28	0	alkadiene; hemiterpene; volatile organic compound	plant metabolite
isobutyl alcohol isobutyl alcohol: RN given refers to parent cpd	2.52	2	0	alkyl alcohol; primary alcohol	Saccharomyces cerevisiae metabolite
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.	2.11	1	0	butanone; dialkyl ketone; methyl ketone; volatile organic compound	bacterial metabolite; polar aprotic solvent
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.	7.05	1	0	chloroethenes	inhalation anaesthetic; mouse metabolite
acrylamide [no description available]	8.17	5	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.	4.05	13	0	alpha,beta-unsaturated monocarboxylic acid	metabolite
peracetic acid Peracetic Acid: A liquid that functions as a strong oxidizing agent. It has an acrid odor and is used as a disinfectant.. peracetic acid : A peroxy acid that is acetic acid in which the OH group is substituted by a hydroperoxy group. It is a versatile oxidising agent that is used as a disinfectant.	5.58	21	0	a peroxy acid	disinfectant; oxidising agent
2,2-dichloroacetyl chloride dichloroacetyl chloride : The acyl chloride obtained by displacement of the hydroxy group of dichloroacetic acid by chloride.	2.25	1	0	acyl chloride	hapten
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.	6.11	21	0	bisphenol	endocrine disruptor; environmental contaminant; xenobiotic; xenoestrogen
dicumyl peroxide [no description available]	2.07	1	0
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.	2.02	1	0	enoate ester; methyl ester	allergen; polymerisation monomer
taurocholic acid Taurocholic Acid: The product of conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and cholerectic.. taurocholate : An organosulfonate oxoanion that is the conjugate base of taurocholic acid.. taurocholic acid : A bile acid taurine conjugate of cholic acid that usually occurs as the sodium salt of bile in mammals.	3.75	2	1	amino sulfonic acid; bile acid taurine conjugate	human metabolite
rhodamine b rhodamine B: RN & N1 from 9th CI Form Index; RN given refers to parent cpd; structure in Merck Index, 9th ed, #7973; TETRAETHYLRHODAMINE was see RHODAMINES 1975-93; use RHODAMINES to search TETRAETHYLRHODAMINE 1975-93. rhodamine B : An organic chloride salt having N-[9-(2-carboxyphenyl)-6-(diethylamino)-3H-xanthen-3-ylidene]-N-ethylethanaminium as the counterion. An amphoteric dye commonly used as a fluorochrome.	4.18	4	0	organic chloride salt; xanthene dye	fluorescent probe; fluorochrome; histological dye
9,10-phenanthrenequinone 9,10-phenanthrenequinone: structure	1.98	1	0	phenanthrenes
2-methylanthraquinone 2-methylanthraquinone: form Morinda officinalis How.. 2-methylanthraquinone : An anthraquinone that is 9,10-anthraquinone in which the hydrogen at position 2 is substituted by a methyl group.	2.06	1	0	anthraquinone
dichlorodicyanobenzoquinone dichlorodicyanobenzoquinone: request from searcher	2.98	4	0
9,10-anthraquinone 9,10-anthraquinone : An anthraquinone that is anthracene in which positions 9 and 10 have been oxidised to carbonyls.	2.6	1	0	anthraquinone
xylitol xylooligosaccharide: structure in first source. pentitol : An alditol obtained by reduction of any pentose.. xylooligosaccharide : An oligosaccharide comprised of xylose residues.	15.26	72	0
2,4,6-trichlorophenol [no description available]	2	1	0	trichlorophenol	carcinogenic agent
n-vinyl-2-pyrrolidinone N-vinyl-2-pyrrolidinone: monomer of POVIDONE; structure given in first source	3.7	7	0	pyrrolidin-2-ones
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.	2.52	2	0	furoic acid	bacterial xenobiotic metabolite; human xenobiotic metabolite; inhibitor; plant metabolite; Saccharomyces cerevisiae metabolite
pyromellitic dianhydride [no description available]	2.11	1	0
2-sec-butylphenol 2-sec-butylphenol: RN given refers to parent cpd. 2-sec-butylphenol : A member of the class of phenols that is phenol carrying a butan-2-yl group at position 2.	7.53	2	0	phenols
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.	2.57	2	0	monoterpenoid; phenols	volatile oil component
salicylaldehyde o-hydroxybenzaldehyde: structure in first source	2.1	1	0	hydroxybenzaldehyde	nematicide; plant metabolite
1-naphthol 1-naphthol: RN given refers to parent cpd. 1-naphthol : A naphthol carrying a hydroxy group at position 1.. hydroxynaphthalene : Any member of the class of naphthalenes that is naphthalene carrying one or more hydroxy groups.	2.08	1	0	naphthol	genotoxin; human xenobiotic metabolite
beta-glucono-1,5-lactone beta-glucono-1,5-lactone: structure. D-glucono-1,5-lactone : An aldono-1,5-lactone obtained from D-gluconic acid.	4.16	4	0	aldono-1,5-lactone; gluconolactone	animal metabolite; mouse metabolite
pyrogallol 1,3-dimethyl ether pyrogallol 1,3-dimethyl ether: structure. 2,6-dimethoxyphenol : A member of the class of phenols that is phenol substituted by methoxy groups at positions 2 and 6.	5.32	16	0	dimethoxybenzene; phenols	plant metabolite
veratrole veratrole: structure. dimethoxybenzene : Any methoxybenzene that consists of a benzene skeleton substituted with two methoxy groups and its derivatives.. veratrole : A dimethoxybenzene with the methoxy groups at ortho-positions.	2.49	2	0	dimethoxybenzene	plant metabolite
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	7.44	2	0	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
3,3'-diaminobenzidine 3,3'-Diaminobenzidine: A chemically and thermodynamically stable derivative of BENZIDINE.. 3,3'-diaminobenzidine : A member of the class of biphenyls that is benzidine in which one of the hydrogens ortho to each of the amino groups has been replaced by an amino group.	2.51	2	0	biphenyls; substituted aniline	histological dye
tolonium chloride Tolonium Chloride: A phenothiazine that has been used as a hemostatic, a biological stain, and a dye for wool and silk. Tolonium chloride has also been used as a diagnostic aid for oral and gastric neoplasms and in the identification of the parathyroid gland in thyroid surgery.. tolonium chloride : An organic chloride salt having 3-amino-7-(dimethylamino)-2-methylphenothiazin-5-ium (tolonium) as the counterion. It is a blue nuclear counterstain that can be used to demonstrate Nissl substance and is also useful for staining mast cell granules, both in metachromatic and orthochromatic techniques.	2.08	1	0
diphenyl diphenyl: RN given refers to unlabeled cpd; structure	3.16	5	0	aromatic fungicide; benzenes; biphenyls	antifungal agrochemical; antimicrobial food preservative
xanthenes Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.	2.86	3	0	xanthene
veratryl alcohol (3,4-dimethoxyphenyl)methanol : A member of the class of benzyl alcohols that is benzyl alcohol in which the hydrogens at positions 3 and 4 of the phenyl group are substituted by methoxy groups.	6.28	47	0	benzyl alcohols; dimethoxybenzene; primary alcohol	fungal metabolite
veratric acid veratric acid: RN given refers to parent cpd; structure. 3,4-dimethoxybenzoic acid : A member of the class of benzoic acids that is benzoic acid substituted by methoxy groups at positions 2 and 3.	2.03	1	0	benzoic acids	allergen; plant metabolite
creosol [no description available]	2.49	2	0	methoxybenzenes; phenols
1-phenylpropanol 1-phenylpropanol: structure in first source	7.6	43	0	organic molecular entity
benzoic anhydride [no description available]	2.41	1	0	acyclic carboxylic anhydride
propylparaben Parabens: Methyl, propyl, butyl, and ethyl esters of p-hydroxybenzoic acid. They have been approved by the FDA as antimicrobial agents for foods and pharmaceuticals. (From Hawley's Condensed Chemical Dictionary, 11th ed, p872)	5.68	24	0	benzoate ester; paraben; phenols	antifungal agent; antimicrobial agent
benzoyl peroxide Benzoyl Peroxide: A peroxide derivative that has been used topically for BURNS and as a dermatologic agent in the treatment of ACNE and POISON IVY DERMATITIS. It is used also as a bleach in the food industry.	2.07	1	0	carbonyl compound
piperonylic acid piperonylic acid: RN given refers to parent cpd; structure. piperonylic acid : A member of the class of benzodioxoles that is 1,3-benzodioxole substituted by a carboxy group at position 5. It is a natural product isolated from several plant species. It is a selective mechanism-based inactivator of the trans-cinnamate 4-hydroxylase enzyme and exhibits antifungal and skin wound healing properties.	3.17	5	0	aromatic carboxylic acid; benzodioxoles; monocarboxylic acid	antifungal agent; EC 1.14.14.91 ( trans-cinnamate 4-monooxygenase) inhibitor; plant metabolite; vulnerary
benzothiazole benzothiazole: structure. benzothiazole : An organic heterobicyclic compound that is a fusion product between benzene and thiazole. The parent of the class of benzothiazoles.	2.03	1	0	benzothiazoles	environmental contaminant; plant metabolite; xenobiotic
2,4,5-trichlorophenol 2,4,5-trichlorophenol: RN given refers to parent cpd; structure. 2,4,5-trichlorophenol : A trichlorophenol carrying chloro groups at positions 2, 4 and 5.	2.02	1	0	trichlorophenol
dilactide dilactide: structure given in first source	3.31	5	0	dioxanes
1,2-dibromo-3-chloropropane 1,2-dibromo-3-chloropropane: RN given refers to cpd with specified locants for bromine & chlorine moieties	2.03	1	0	organochlorine compound
2-methyltetrahydrofuran 2-methyltetrahydrofuran: structure in first source	7.59	2	0
4-butyrolactone 4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.	4.51	9	0	butan-4-olide	metabolite; neurotoxin
butyl methacrylate [no description available]	7.08	1	0	enoate ester
ethylene dimethacrylate ethylene glycol dimethacrylate : The enoate ester that is the 1,2-bis(methacryloyl) derivative of ethylene glycol.	2.31	1	0	enoate ester	allergen; cross-linking reagent; polymerisation monomer
tetrahydrofurfuryl alcohol tetrahydrofurfuryl alcohol: RN given refers to parent cpd; structure. tetrahydrofurfuryl alcohol : A primary alcohol that is methanol in which one of the hydrogens of the methyl group has been replaced by a tetrahydrofuran-2-yl group.	2.13	1	0	oxolanes; primary alcohol	protic solvent
furfuryl alcohol furfuryl alcohol: structure. furfuryl alcohol : A furan bearing a hydroxymethyl substituent at the 2-position.	8.16	5	0	furans; primary alcohol	Maillard reaction product
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.	10.53	223	0	aldehyde; furans	Maillard reaction product; metabolite
benzenesulfonic acid benzenesulfonic acid: RN given refers to parent cpd. benzenesulfonic acid : The simplest member of the class of a benzenesulfonic acids that consists of a benzene carrying a single sulfo group.	2.76	2	0	benzenesulfonic acids
arsanilic acid Arsanilic Acid: An arsenical which has been used as a feed additive for enteric conditions in pigs and poultry. It causes blindness and is ototoxic and nephrotoxic in animals.	7.25	1	0	organoarsonic acid
4-toluenesulfonyl chloride [no description available]	1.97	1	0
acetophenone acetophenone : A methyl ketone that is acetone in which one of the methyl groups has been replaced by a phenyl group.	2.55	2	0	acetophenones	animal metabolite; photosensitizing agent; xenobiotic
benzoyl chloride benzoyl chloride: potential carcinogens in manufacturing process. benzoyl chloride : An acyl chloride consisting of benzene in which a hydrogen is replaced by an acyl chloride group. It is an important chemical intermediate for the manufacture of other chemicals, dyes, perfumes, herbicides and pharmaceuticals.	2.06	1	0	acyl chloride; benzenes	carcinogenic agent
cyclohexanecarboxylic acid cyclohexanecarboxylic acid: RN given refers to parent cpd. cyclohexanecarboxylic acid : A monocarboxylic acid that consists of cyclohexane substituted by a carboxy group.	2.08	1	0	monocarboxylic acid
nitrobenzene nitrobenzene : A nitroarene consisting of benzene carrying a single nitro substituent. An industrial chemical used widely in the production of aniline.	4.35	19	0	nitroarene; nitrobenzenes
trehalose alpha,alpha-trehalose : A trehalose in which both glucose residues have alpha-configuration at the anomeric carbon.	3.08	4	0	trehalose	Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
4-hydroxyacetophenone 4-hydroxyacetophenone: promotes secretion of bile & bile salts, which promotes griseofulvin absorption in the duodenum. 4'-hydroxyacetophenone : A monohydroxyacetophenone carrying a hydroxy substituent at position 4'.	2.57	2	0	monohydroxyacetophenone	fungal metabolite; mouse metabolite; plant metabolite
4-chloronitrobenzene [no description available]	2.41	1	0	C-nitro compound
4-anisic acid 4-methoxybenzoic acid: structure in first source. 4-methoxybenzoic acid : A methoxybenzoic acid substituted with a methoxy group at position C-4.	2.05	1	0	methoxybenzoic acid	plant metabolite
terephthalic acid terephthalic acid: RN given refers to 1,4-benzenedicarboxylic acid. terephthalic acid : A benzenedicarboxylic acid carrying carboxy groups at positions 1 and 4. One of three possible isomers of benzenedicarboxylic acid, the others being phthalic and isophthalic acids.	4.35	4	0	benzenedicarboxylic acid
ethylbenzene [no description available]	7.49	2	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.	3.11	4	0	styrenes; vinylarene; volatile organic compound	mouse metabolite; mutagen; plant metabolite
methylaniline methylaniline: RN given refers to parent cpd. methylaniline : A substituted aniline carrying one or more methyl groups at unspecified positions.	2.54	2	0	methylaniline; phenylalkylamine; secondary amine
anisole anisole : A monomethoxybenzene that is benzene substituted by a methoxy group.	7.94	4	0	monomethoxybenzene	plant metabolite
phenylmethanesulfonic acid phenylmethanesulfonic acid: RN given refers to parent cpd	2.04	1	0
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.	2.75	3	0	aromatic ether	plant metabolite
boric acid [no description available]	7.31	1	0	boric acids	astringent
n-benzyl-n,n-dimethylamine [no description available]	2.25	1	0
4-anisidine 4-anisidine: RN given refers to parent cpd. p-anisidine : A substituted aniline that is aniline in which the hydrogen para to the amino group has been replaced by a methoxy group. It is used as a reagent for the detection of oxidation products such as aldehydes and ketones in fats and oils.	2.13	1	0	methoxybenzenes; primary amino compound; substituted aniline	genotoxin; reagent
anisyl alcohol anisyl alcohol: structure given in first source	2.39	2	0	benzyl alcohols
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.	2.5	2	0	caprolactams	human blood serum metabolite
epichlorohydrin Epichlorohydrin: A chlorinated epoxy compound used as an industrial solvent. It is a strong skin irritant and carcinogen.. epichlorohydrin : An epoxide that is 1,2-epoxypropene in which one of the methyl hydrogens is substituted by chlorine.	3.8	10	0	epoxide; organochlorine compound
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.	2.57	2	0	enoate ester; epoxide
propargyl bromide propargyl bromide: structure in first source	2.08	1	0
1,3-butadiene buta-1,3-diene : A butadiene with unsaturation at positions 1 and 3.	2.69	2	0	butadiene	carcinogenic agent; mutagen
acrolein [no description available]	4.95	35	0	enal	herbicide; human xenobiotic metabolite; toxin
allyl chloride [no description available]	2.15	1	0	organochlorine compound
acrylonitrile [no description available]	7.9	3	0	aliphatic nitrile; volatile organic compound	antifungal agent; carcinogenic agent; fungal metabolite; mutagen; polar aprotic solvent
allyl alcohol allyl alcohol: structure. allylic alcohol : An alcohol where the hydroxy group is attached to a saturated carbon atom adjacent to a double bond (R groups may be H, organyl, etc.).. allyl alcohol : A propenol in which the C=C bond connects C-2 and C-3. It is has been found in garlic (Allium sativum). Formerly used as a herbicide for the control of various grass and weed seeds.	2.1	1	0	primary allylic alcohol; propenol	antibacterial agent; fungicide; herbicide; insecticide; plant metabolite
glyoxal [no description available]	3.31	6	0	dialdehyde	agrochemical; allergen; pesticide; plant growth regulator
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	2.01	1	0	alkane
3-hydroxybutanal [no description available]	2.83	3	0
methyl isobutyl ketone [no description available]	2.94	3	0	ketone
acetic anhydride acetic anhydride: RN given refers to unlabeled cpd; structure. acetic anhydride : An acyclic carboxylic anhydride derived from acetic acid.	2.47	2	0	acyclic carboxylic anhydride	metabolite; reagent
gamma-valerolactone gamma-valerolactone: metabolite of n-hexane; RN given refers to cpd with methyl moiety in position 5. gamma-valerolactone : A butan-4-olide that is dihydrofuran-2(3H)-one substituted by a methyl group at position 5. It has been found in the urine samples of humans exposed to n-hexane.	5.84	15	0	butan-4-olide	flavouring agent; human xenobiotic metabolite
succinic anhydride [no description available]	2.47	2	0	cyclic dicarboxylic anhydride; tetrahydrofurandione
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.	2.52	2	0	cyclic dicarboxylic anhydride; furans	allergen
cyanuric chloride cyanuric chloride : A chloro-1,3,5-triazine in which the triazine ring is substituted on each carbon by chlorine. Its main use is in the preparation of the triazine-class pesticides.	2.08	1	0	chloro-1,3,5-triazine; organochlorine compound	cross-linking reagent
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.	2.06	1	0	cyclohexanols; secondary alcohol	solvent
cyclohexanone [no description available]	7.11	1	0	cyclohexanones	human xenobiotic 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.	2.8	3	0	alkane; volatile organic compound	non-polar solvent; refrigerant
2-hydroxyethylhydrazine 2-hydroxyethylhydrazine: inhibitor of phospholipid methylation in yeast	2.02	1	0	hydrazines	herbicide
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.	3.21	5	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.	3.73	9	0	cyclic ether; oxolanes; saturated organic heteromonocyclic parent; volatile organic compound	polar aprotic solvent
furan furan : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing four carbons and one oxygen, with formula C4H4O. It is a toxic, flammable, low-boiling (31degreeC) colourless liquid.	3.15	5	0	furans; mancude organic heteromonocyclic parent; monocyclic heteroarene	carcinogenic agent; hepatotoxic agent; Maillard reaction product
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	7.8	3	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
n-hexane hexane : An unbranched alkane containing six carbon atoms.	2.49	2	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).	8.45	6	0	butanediol; glycol	neurotoxin; prodrug; protic solvent
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.	2.13	1	0	cycloalkane; volatile organic compound	non-polar solvent
diethylenetriamine diethylenetriamine: RN given refers to parent cpd	2.59	2	0	polyazaalkane; triamine
diethanolamine diethanolamine: RN given refers to parent cpd. diethanolamine : A member of the class of ethanolamines that is ethanolamine having a N-hydroxyethyl substituent.	2.04	1	0	ethanolamines	human xenobiotic metabolite
octylamine octylamine: RN given refers to 1-octylamine. octan-1-amine : An 8-carbon primary aliphatic amine.	2.08	1	0	primary aliphatic amine	metabolite
n-decyl alcohol n-decyl alcohol: RN given refers to parent cpd. decanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of ten carbon atoms.. decan-1-ol : A fatty alcohol consisting of a hydroxy function at C-1 of an unbranched saturated chain of ten carbon atoms.	2.51	2	0	decanol; primary alcohol	metabolite; pheromone; protic solvent
myristyl alcohol myristyl alcohol: RN given refers to parent cpd. tetradecan-1-ol : A long-chain fatty alcohol that is tetradecane substituted by a hydroxy group at position 1.. tetradecanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of fourteen carbon atoms.	2.25	1	0	long-chain primary fatty alcohol; tetradecanol	pheromone; plant metabolite; volatile oil component
eicosane icosane : A straight chain alkane composed of 20 carbon atoms. It has been isolated from the leaves of Agave attenuata.	2.25	1	0	long-chain alkane	plant metabolite
propylene propylene: structure	2.84	3	0	alkene; gas molecular entity	refrigerant; xenobiotic
pentaerythritol pentaerythritol: RN given refers to parent cpd; structure in Merck Index, 9th ed, #6904. pentaerythritol : A tetrol that is neopentane in which one of the methyl hydrogens of all four methyl groups are replaced by hydroxy groups. It is a chemical intermediate used in the production of explosives, plastics, paints, appliances, and cosmetics.	2.21	1	0	primary alcohol; tetrol	flame retardant; laxative
triphenyl phosphate triphenyl phosphate: structure. triphenyl phosphate : An aryl phosphate resulting from the formal condensation of phosphoric acid with 3 mol eq. of phenol.	2.41	1	0	aryl phosphate	flame retardant; plasticiser
tris(chloroethyl)phosphate tris(chloroethyl)phosphate: has gonadotoxic effects. tris(2-chloroethyl) phosphate : A trialkyl phosphate that is the tris(2-chloroethyl) ester of phosphoric acid.	2.41	1	0	organochlorine compound; trialkyl phosphate
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.	3.35	1	0	diester; phthalate ester	androstane receptor agonist; apoptosis inhibitor; plasticiser
hexachlorobenzene Hexachlorobenzene: An agricultural fungicide and seed treatment agent.. hexachlorobenzene : A member of the class of chlorobenzenes that is benzene in which all of the hydrogens are replaced by chlorines. An agricultural fungicide introduced in the mid-1940s and formerly used as a seed treatment, its use has been banned since 1984 under the Stockholm Convention on Persistent Organic Pollutants.	7.4	2	0	aromatic fungicide; chlorobenzenes	antifungal agrochemical; carcinogenic agent; persistent organic pollutant
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.	7.95	4	0	trinitrotoluene	explosive
framycetin Framycetin: A component of NEOMYCIN that is produced by Streptomyces fradiae. On hydrolysis it yields neamine and neobiosamine B. (From Merck Index, 11th ed). framycetin : A tetracyclic antibacterial agent derived from neomycin, being a glycoside ester of neamine and neobiosamine B.	3.45	2	0	aminoglycoside	allergen; antibacterial drug; Escherichia coli metabolite
2,4-dinitroanisole 2,4-dinitroanisole : A member of the class of dinitroanisoles that is 2-nitroanisole in which the hydrogen para to the methoxy group is replaced by a second nitro group.	7.07	1	0	dinitroanisoles	explosive
benzoin [no description available]	2.67	3	0	benzoins; secondary alpha-hydroxy ketone	EC 3.1.1.1 (carboxylesterase) inhibitor
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.	2.73	3	0	acene; anthracenes; ortho-fused tricyclic hydrocarbon
veratraldehyde [no description available]	2.17	1	0	benzaldehydes; dimethoxybenzene	antifungal agent
2,4-dichlorophenol 2,4-dichlorophenol: RN given refers to unlabeled parent+ cpd; structure. 2,4-dichlorophenol : A dichlorophenol that is phenol carrying chloro substituents at positions 2 and 4.	7.93	4	0	dichlorophenol
cyclopentanone [no description available]	2.1	1	0	cyclopentanones	Maillard reaction product
2,4-dinitrotoluene 2,4-dinitrotoluene : A dinitrotoluene in which the methyl group is ortho to one of the nitro groups and para to the other. It is the most common isomer of dinitrotoluene.	2.39	2	0	dinitrotoluene
vanillic acid Vanillic Acid: A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13).. vanillic acid : A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3.	6.35	48	0	methoxybenzoic acid; monohydroxybenzoic acid	plant metabolite
trimethyl borate trimethyl borate : A member of the class of borate esters obtained by the formal condensation of three equivalents of methanol with boric acid.	2.06	1	0	borate esters
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.	2.1	1	0	carboxylic acid; dicarboxylic acid monoamide; N-(1-naphthyl)carboxamide	herbicide
captan Captan: One of the phthalimide fungicides.. captan : A dicarboximide that is 3a,4,7,7a-tetrahydrophthalimide in which the hydrogen attached to the nitrogen is replaced by a trichloromethyl group. A non-systemic fungicide introduced in the 1950s, it is widely used for the control of fungal diseases in fruits, vegetables, and ornamental crops.	2.45	2	0	isoindoles; organochlorine compound; organosulfur compound; phthalimide fungicide	antifungal agrochemical
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.	2.03	1	0	indol-3-yl carboxylic acid	auxin; plant hormone; plant metabolite
uridine diphosphate glucose Uridine Diphosphate Glucose: A key intermediate in carbohydrate metabolism. Serves as a precursor of glycogen, can be metabolized into UDPgalactose and UDPglucuronic acid which can then be incorporated into polysaccharides as galactose and glucuronic acid. Also serves as a precursor of sucrose lipopolysaccharides, and glycosphingolipids.. UDP-alpha-D-glucose : The alpha-anomer of UDP-alpha-D-glucose. It is used in nucleotide sugars metabolism.	2.51	2	0	UDP-D-glucose	fundamental metabolite
syringaldehyde syringaldehyde: isolated from nonfermented fiber fractions of oat hulls and cottonseed hulls. syringaldehyde : A hydroxybenzaldehyde that is 4-hydroxybenzaldehyde substituted by methoxy groups at positions 3 and 5. Isolated from Pisonia aculeata and Panax japonicus var. major, it exhibits hypoglycemic activity.	4.1	14	0	dimethoxybenzene; hydroxybenzaldehyde	hypoglycemic agent; plant 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.	4.84	32	0	naphthol	antinematodal drug; genotoxin; human urinary metabolite; human xenobiotic metabolite; mouse metabolite; radical scavenger
shikimic acid Shikimic Acid: A tri-hydroxy cyclohexene carboxylic acid important in biosynthesis of so many compounds that the shikimate pathway is named after it.. shikimic acid : A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3R,4S,5R stereoisomer). It is an intermediate metabolite in plants and microorganisms.	11.7	29	0	alpha,beta-unsaturated monocarboxylic acid; cyclohexenecarboxylic acid; hydroxy monocarboxylic acid	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
nitrilotriacetic acid Nitrilotriacetic Acid: A derivative of acetic acid, N(CH2COOH)3. It is a complexing (sequestering) agent that forms stable complexes with Zn2+. (From Miall's Dictionary of Chemistry, 5th ed.)	2.1	1	0	NTA; tricarboxylic acid	carcinogenic agent; nephrotoxic agent
protocatechualdehyde protocatechualdehyde: found in wheat grains, wheat seedlings, & other plants; RN given refers to parent cpd; see also rancinamycins; structure	2.02	1	0	dihydroxybenzaldehyde
estragole estragole : A phenylpropanoid that is chavicol in which the hydroxy group is replaced by a methoxy group.	2.15	1	0	alkenylbenzene; monomethoxybenzene; phenylpropanoid	carcinogenic agent; flavouring agent; genotoxin; insect attractant; plant metabolite
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.	2.25	1	0	acrylate ester
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	3.62	8	0	acetate ester; ethyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; metabolite; polar aprotic solvent; Saccharomyces cerevisiae metabolite
mesityl oxide mesityl oxide: solvent for extraction of nitrocellulose, many resins, & tellurium; structure	2.13	1	0	olefinic compound
hexanoic acid hexanoic acid : A C6, straight-chain saturated fatty acid.	2.52	2	0	medium-chain fatty acid; straight-chain saturated fatty acid	human metabolite; plant metabolite
lauryl methacrylate dodecyl methacrylate: monomer unit of various acrylate polymers used to form gels,plastics and some biocompatible materials; structure in first source	7.41	1	0
sodium cyanide Sodium Cyanide: A highly poisonous compound that is an inhibitor of many metabolic processes and is used as a test reagent for the function of chemoreceptors. It is also used in many industrial processes.. sodium cyanide : A cyanide salt containing equal numbers of sodium cations and cyanide anions.	1.98	1	0	cyanide salt; one-carbon compound; sodium salt	EC 1.15.1.1 (superoxide dismutase) inhibitor
mequinol mequinol: depigmenting agent; RN given refers to parent cpd	2.43	2	0	methoxybenzenes; phenols	metabolite
1,4-dimethoxybenzene 1,4-dimethoxybenzene: structure given in first source	7.05	1	0	dimethoxybenzene
potassium cyanide [no description available]	2.05	1	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
sulfalene Sulfalene: Long-acting plasma-bound sulfonamide used for respiratory and urinary tract infections and also for malaria.	1.96	1	0	pyrazines; sulfonamide antibiotic; sulfonamide
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.	3.98	13	0	catechin	antioxidant; plant metabolite
thiamine pyrophosphate Thiamine Pyrophosphate: The coenzyme form of Vitamin B1 present in many animal tissues. It is a required intermediate in the PYRUVATE DEHYDROGENASE COMPLEX and the KETOGLUTARATE DEHYDROGENASE COMPLEX.. thiamine(1+) diphosphate chloride : An organic chloride salt of thiamine(1+) diphosphate.	2.61	2	0	organic chloride salt; vitamin B1
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.	2.03	1	0	ortho- and peri-fused polycyclic arene; perylenes
dibenzo(1,4)dioxin dibenzo(1,4)dioxin: structure	2.01	1	0	dibenzodioxine; heteranthrene; mancude organic heterotricyclic parent; oxacycle; polycyclic heteroarene
benzofuran benzofuran: RN & structure given in first source. 1-benzofuran : A benzofuran consisting of fused benzene and furan rings. It is the parent compound of the class of 1-benzofurans.	2.05	1	0	1-benzofurans; benzofuran
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.	2.11	1	0	1,3-benzoxazoles; mancude organic heterobicyclic parent
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	7.08	57	0	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
thiazoles [no description available]	2.75	3	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
pyrimidine pyrimidine : The parent compound of the pyrimidines; a diazine having the two nitrogens at the 1- and 3-positions.	2.11	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.	2.17	1	0	diazine; pyrazines	Daphnia magna metabolite
nitroblue tetrazolium Nitroblue Tetrazolium: Colorless to yellow dye that is reducible to blue or black formazan crystals by certain cells; formerly used to distinguish between nonbacterial and bacterial diseases, the latter causing neutrophils to reduce the dye; used to confirm diagnosis of chronic granulomatous disease.	1.99	1	0	organic cation
triphenyltetrazolium triphenyltetrazolium: RN given refers to parent cpd. 2,3,5-triphenyltetrazolium : An organic cation that is tetrazole carrying three phenyl substituents at positions 2, 3 and 5.	2.07	1	0	organic cation
methylphenazonium methosulfate Methylphenazonium Methosulfate: Used as an electron carrier in place of the flavine enzyme of Warburg in the hexosemonophosphate system and also in the preparation of SUCCINIC DEHYDROGENASE.	1.99	1	0	azaheterocycle sulfate salt; phenazines
hydrazine diamine : Any polyamine that contains two amino groups.	7.47	2	0	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
evans blue Evans Blue: An azo dye used in blood volume and cardiac output measurement by the dye dilution method. It is very soluble, strongly bound to plasma albumin, and disappears very slowly.. Evans blue : An organic sodium salt that is the tetrasodium salt of 6,6'-{(3,3'-dimethyl[1,1'-biphenyl]-4,4'-diyl)bis[diazene-2,1-diyl]}bis(4-amino-5-hydroxynaphthalene-1,3-disulfonate). It is sometimes used as a counterstain, especially in fluorescent methods to suppress background autofluorescence.	2.49	2	0	organic sodium salt	fluorochrome; histological dye; sodium channel blocker; teratogenic agent
5-fluorouridine [no description available]	2.06	1	0	organofluorine compound; uridines	mutagen
perfluorooctanoic acid perfluorooctanoic acid: RN given refers to parent cpd. perfluorooctanoic acid : A fluoroalkanoic acid that is perfluorinated octanoic acid.	2.49	2	0	fluoroalkanoic acid	carcinogenic agent; endocrine disruptor; environmental contaminant; surfactant; xenobiotic
prenylamine Prenylamine: A drug formerly used in the treatment of angina pectoris but superseded by less hazardous drugs. Prenylamine depletes myocardial catecholamine stores and has some calcium channel blocking activity. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1406)	3.07	1	0	diarylmethane
silicon carbide silicon carbide: fibers used for reinforcement of porcelain crowns; a feldspathic body (gingival) porcelain; used to coat titanium hip prostheses	2.15	1	0	organosilicon 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.	2.49	2	0	nitrile; one-carbon compound	EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor
4-methylcatechol [no description available]	2.21	1	0	methylcatechol	antioxidant; carcinogenic agent; hapten; human metabolite; plant metabolite
4-toluenesulfonyl fluoride 4-toluenesulfonyl fluoride: inhibitor of peptide hydrolases; structure in second source	2	1	0
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.	2.11	1	0	monofluorobenzenes	NMR chemical shift reference compound
ketene ketene: structure. ketene : Carbonyl compounds where the C=O bond is conjugated to an alkylidene group.	7.41	1	0	ketene
limestone Calcium Carbonate: Carbonic acid calcium salt (CaCO3). An odorless, tasteless powder or crystal that occurs in nature. It is used therapeutically as a phosphate buffer in hemodialysis patients and as a calcium supplement.. calcium carbonate : A calcium salt with formula CCaO3.	5.64	13	0	calcium salt; carbonate salt; inorganic calcium salt; one-carbon compound	antacid; fertilizer; food colouring; food firming agent
hopane hopane: RN given refers to cpd without isomeric designation	2.03	1	0	terpenoid fundamental parent; triterpene
chenodeoxycholic acid Chenodeoxycholic Acid: A bile acid, usually conjugated with either glycine or taurine. It acts as a detergent to solubilize fats for intestinal absorption and is reabsorbed by the small intestine. It is used as cholagogue, a choleretic laxative, and to prevent or dissolve gallstones.. chenodeoxycholic acid : A dihydroxy-5beta-cholanic acid that is (5beta)-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 7 respectively.. chenodeoxycholate : Conjugate base of chenodeoxycholic acid; major species at pH 7.3.	5.14	3	1	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
glycocholic acid Glycocholic Acid: The glycine conjugate of CHOLIC ACID. It acts as a detergent to solubilize fats for absorption and is itself absorbed.. glycocholic acid : A bile acid glycine conjugate having cholic acid as the bile acid component.. glycocholate : A cholanic acid conjugate anion that is the conjugate base of glycocholic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	3.45	2	0	bile acid glycine conjugate	human metabolite
fusarium Fusarium: A mitosporic Hypocreales fungal genus, various species of which are important parasitic pathogens of plants and a variety of vertebrates. Teleomorphs include GIBBERELLA.	5.41	54	0
indirubin [no description available]	2.41	1	0
diphenic acid [no description available]	1.98	1	0	dicarboxylic acid
cdta CDTA: RN given refers to parent cpd; structure	2.06	1	0	organooxygen compound
ninhydrin Ninhydrin: 2,2-Dihydroxy-1H-indene-1,3-(2H)-dione. Reagent toxic to skin and mucus membranes. It is used in chemical assay for peptide bonds, i.e., protein determinations and has radiosensitizing properties.. ninhydrin : A member of the class of indanones that is indane-1,3-dione bearing two additional hydroxy substituents at position 2.	2.77	3	0	aromatic ketone; beta-diketone; indanones; ketone hydrate	colour indicator; human metabolite
indole-3-carbaldehyde indole-3-carbaldehyde: metabolite of tryptophan; structure. indole-3-carbaldehyde : A heteroarenecarbaldehyde that is indole in which the hydrogen at position 3 has been replaced by a formyl group.	2.03	1	0	heteroarenecarbaldehyde; indole alkaloid; indoles	bacterial metabolite; human xenobiotic metabolite; marine metabolite; plant metabolite
methyl red methyl red: RN given refers to parent cpd; structure. methyl red : An azo dye consisting of benzoic acid substituted at position 2 by a 4-[(dimethylamino)phenyl]diazenyl group.	2.6	1	0
coumaran 2,3-dihydrobenzofuran : A member of the class of 1-benzofurans that is the 2,3-dihydroderivative of benzofuran.	7.46	2	0	1-benzofurans	metabolite
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	3.36	6	0	carbonate salt; organic sodium salt
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).	7.41	1	0	botanical anti-fungal agent; p-menthane monoterpenoid; phenols	agrochemical; antimicrobial agent; flavouring agent; TRPA1 channel agonist; volatile oil component
indophenol Indophenol: A deep blue dye (with the formula OC6H4NC6H4OH) used to detect AMMONIA in a common test called the Berthelot's reaction and to detect PARACETAMOL by spectrophotometry.. indophenol : A quinone imine obtained by formal condensation of one of the keto groups of benzoquinone with the amino group of 4-hydroxyaniline.	2.01	1	0	quinone imine	dye
caprolactone hexano-6-lactone : A epsilon-lactone that is oxepane substituted by an oxo group at position 2.	7.46	2	0	epsilon-lactone
5-nonanone [no description available]	2.6	1	0
1,3-propanediol propane-1,3-diol : The simplest member of the class of propane-1,3-diols, consisting of propane in which one hydrogen from each methyl group is substituted by a hydroxy group. A colourless, viscous, water-miscible liquid with a high (210degreeC) boiling point, it is used in the synthesis of certain polymers and as a solvent and antifreeze.	3.05	4	0	propane-1,3-diols	metabolite; protic solvent
acetyl bromide [no description available]	3.82	11	0
anemonin anemonin: a furanone dimer found in RANUNCULACEAE; do not confuse with anemonine which is 5-(carboxymethyl)-1,1-dimethylimidazolium hydroxide inner salt; ranunculine is hydrolyzed to protoanemonin which dimerizes to anemonin; structure	2.03	1	0
abietic acid abietic acid : An abietane diterpenoid that is abieta-7,13-diene substituted by a carboxy group at position 18.	2.31	1	0	abietane diterpenoid; monocarboxylic acid	plant metabolite
podophyllotoxin Podophyllum: A genus of poisonous American herbs, family BERBERIDACEAE. The roots yield PODOPHYLLOTOXIN and other pharmacologically important agents. The plant was formerly used as a cholagogue and cathartic. It is different from the European mandrake, MANDRAGORA.	2.36	2	0	furonaphthodioxole; lignan; organic heterotetracyclic compound	antimitotic; antineoplastic agent; keratolytic drug; microtubule-destabilising agent; plant metabolite; tubulin modulator
triphenylmethane triphenylmethane : A triarylmethane in which the three aryl groups are phenyl. It forms the basic skeleton of several synthetic dyes.	2.17	1	0	triarylmethane	environmental contaminant; xenobiotic
dihydrotestosterone Dihydrotestosterone: A potent androgenic metabolite of TESTOSTERONE. It is produced by the action of the enzyme 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE.. 17beta-hydroxyandrostan-3-one : A 17beta-hydroxy steroid that is testosterone in which the 4-5 double bond has been reduced to a single bond with unspecified configuration at position 5.. 17beta-hydroxy-5alpha-androstan-3-one : A 17beta-hydroxy steroid that is testosterone in which the 4,5 double bond has been reduced to a single bond with alpha-configuration at position 5.	2.38	2	0	17beta-hydroxy steroid; 17beta-hydroxyandrostan-3-one; 3-oxo-5alpha-steroid	androgen; Daphnia magna metabolite; human metabolite; mouse metabolite
n-hydroxyphthalimide N-hydroxyphthalimide: causes contact dermititis	2.17	1	0
flavone flavone: RN given refers to unlabeled cpd; structure given in first source. flavone : The simplest member of the class of flavones that consists of 4H-chromen-4-one bearing a phenyl substituent at position 2.	2.57	2	0	flavones	metabolite; nematicide
gluconic acid gluconic acid: zinc gluconate has anti-inflammatory activity; RN given refers to (D)-isomer; all RRs refers to (D)-isomer unless otherwise noted. ketogluconic acid : A gluconic acid that contains a ketonic carbonyl group.. D-gluconic acid : A gluconic acid having D-configuration.	4.34	5	0	gluconic acid	chelator; Penicillium metabolite
copper gluconate Gluconates: Derivatives of gluconic acid (the structural formula HOCH2(CHOH)4COOH), including its salts and esters.	4.65	7	0	organic molecular entity
2,4,6-trimethylphenol [no description available]	2.07	1	0	hydroxytoluene
uridine diphosphate n-acetylglucosamine Uridine Diphosphate N-Acetylglucosamine: Serves as the biological precursor of insect chitin, of muramic acid in bacterial cell walls, and of sialic acids in mammalian glycoproteins.	2.07	1	0
cellobiose beta-cellobiose : A cellobiose with beta configuration at the reducing-end glucose residue.	6.68	38	0	cellobiose	epitope
syringic acid syringic acid: RN given refers to parent cpd; structure in third source. syringic acid : A dimethoxybenzene that is 3,5-dimethyl ether derivative of gallic acid.	4.09	14	0	benzoic acids; dimethoxybenzene; phenols	plant metabolite
hydroxyhydroquinone benzene-1,2,4-triol : A benzenetriol carrying hydroxy groups at positions 1, 2 and 4.	2.72	2	0	benzenetriol	mouse metabolite
2-methylfuran 2-methylfuran : A member of the class of furans that is furan in which the hydrogen at position 2 is replaced by a methyl group.	2.78	3	0	furans; volatile organic compound	flavouring agent; fuel; hepatotoxic agent; human urinary metabolite; plant metabolite
methamphetamine Methamphetamine: A central nervous system stimulant and sympathomimetic with actions and uses similar to DEXTROAMPHETAMINE. The smokable form is a drug of abuse and is referred to as crank, crystal, crystal meth, ice, and speed.. methamphetamine : A member of the class of amphetamines in which the amino group of (S)-amphetamine carries a methyl substituent.	2.6	1	0	amphetamines; secondary amine	central nervous system stimulant; environmental contaminant; neurotoxin; psychotropic drug; xenobiotic
ethyl levulinate ethyl levulinate: structure in first source	7.6	1	0	oxo carboxylic acid
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.	2.11	1	0	amino acid zwitterion; beta-amino acid; monocarboxylic acid	metabolite
maleimide [no description available]	7.57	2	0	dicarboximide; maleimides	EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
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.	9.45	20	0	dialdehyde	biomarker
eosine yellowish-(ys) Eosine Yellowish-(YS): A versatile red dye used in cosmetics, pharmaceuticals, textiles, etc., and as tissue stain, vital stain, and counterstain with HEMATOXYLIN. It is also used in special culture media.. eosin YS dye : An organic sodium salt that is 2',4',5',7'-tetrabromofluorescein in which the carboxy group and the phenolic hydroxy group have been deprotonated and the resulting charge is neutralised by two sodium ions.	2.11	1	0	organic sodium salt; organobromine compound	fluorochrome; histological dye
gentian violet Gentian Violet: A dye that is a mixture of violet rosanilinis with antibacterial, antifungal, and anthelmintic properties.. crystal violet : An organic chloride salt that is the monochloride salt of crystal violet cation. It has been used in creams for the topical treatment of bacterial and fungal infections, being effective against some Gram-positive bacteria (notably Staphylococcus species) and some pathogenic fungi (including Candida species) but use declined following reports of animal carcinogenicity. It has also been used for dying wood, silk, and paper, as well as a histological stain.	3.36	6	0	organic chloride salt	anthelminthic drug; antibacterial agent; antifungal agent; antiseptic drug; histological dye
resazurin resazurin: used as indicator in detection of hyposulfite (sulfoxylate); in food research (reductase test); structure	2.17	1	0	phenoxazine
neutral red Neutral Red: A vital dye used as an indicator and biological stain. Various adverse effects have been observed in biological systems.. neutral red : A hydrochloride obtained by combining the free base of neutral red with one equivalent of hydrochloric acid. Neutral red acts as a pH indicator, changing from red to yellow between pH 6.8 and 8.0.	1.98	1	0	hydrochloride	acid-base indicator; dye; two-colour indicator
trimesic acid trimesic acid: RN given refers to parent cpd. benzene-1,3,5-tricarboxylic acid : A tricarboxylic acid that consists of benzene substituted by carboxy groups at positions 1, 3 and 5.	2.13	1	0	benzoic acids; tricarboxylic acid
lignoceric acid lignoceric acid: RN given refers to parent cpd; structure. tetracosanoic acid : A C24 straight-chain saturated fatty acid.	2.03	1	0	straight-chain saturated fatty acid; very long-chain fatty acid	Daphnia tenebrosa metabolite; human metabolite; plant metabolite; volatile oil component
2-hydroxybutyric acid 2-hydroxybutyric acid: RN given refers to cpd without isomeric designation. hydroxybutyric acid : Any compound comprising a butyric acid core carrying at least one hydroxy substituent.. 2-hydroxybutyric acid : A hydroxybutyric acid having a single hydroxyl group located at position 2; urinary secretion of 2-hydroxybutyric acid is increased with alcohol ingestion or vigorous physical exercise and is associated with lactic acidosis and ketoacidosis in humans and diabetes in animals.	2.13	1	0	2-hydroxy monocarboxylic acid; hydroxybutyric acid	algal metabolite; human metabolite
chlorotrianisene Chlorotrianisene: A powerful synthetic, non-steroidal estrogen.	1.94	1	0	chloroalkene	antineoplastic agent; estrogen receptor modulator; xenoestrogen
malachite green malachite green: RN given refers to parent cpd; structure. malachite green : An organic chloride salt that is the monochloride salt of malachite green cation. Used as a green-coloured dye, as a counter-stain in histology, and for its anti-fungal properties in aquaculture.	3.04	3	0	organic chloride salt	antibacterial agent; antifungal drug; carcinogenic agent; environmental contaminant; fluorochrome; histological dye; teratogenic agent
congo red Congo Red: An acid dye used in testing for hydrochloric acid in gastric contents. It is also used histologically to test for AMYLOIDOSIS.. Congo Red : An indicator dye that is blue-violet at pH 3.0 and red at pH 5.0.	3.91	10	0	bis(azo) compound
3-hydroxyflavone 3-hydroxyflavone: structure given in first source. flavonol : A monohydroxyflavone that is the 3-hydroxy derivative of flavone.	3.62	8	0	flavonols; monohydroxyflavone
potassium carbonate potassium carbonate : A potassium salt that is the dipotassium salt of carbonic acid.	3.14	5	0	carbonate salt; potassium salt	catalyst; fertilizer; flame retardant
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.	1.96	1	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
levulinic acid levulinic acid: inhibits 5-aminolevulinic acid dehydratase; RN given refers to parent cpd; structure in Merck Index, 9th ed, #5316. 4-oxopentanoic acid : An oxopentanoic acid with the oxo group in the 4-position.	7.78	29	0	oxopentanoic acid; straight-chain saturated fatty acid	plant metabolite
methyl n-butyl ketone Methyl n-Butyl Ketone: An industrial solvent which causes nervous system degeneration. MBK is an acronym often used to refer to it.. hexanone : A ketone that is a hexane carrying an oxo substituent at unspecified position.	2.59	2	0	ketone
2,3-dinitrotoluene dinitrotoluene : Any nitrotoluene carrying two nitro substituents.. 2,3-dinitrotoluene : A dinitrotoluene that is toluene in which the hydrogens at positions 2 and 3 have been replaced by nitro groups.	2.05	1	0	dinitrotoluene	explosive
2-nitrofluorene 2-nitrofluorene: RN given refers to cpd with locant with nitro moiety in 2 position. 2-nitrofluorene : A nitroarene that is fluorene substituted by a nitro group at position 2.	2.01	1	0	nitroarene	carcinogenic agent; mutagen
3,5-dinitrosalicylic acid 3,5-dinitrosalicylic acid: RN given refers to parent cpd. 3,5-dinitrosalicylic acid : A monohydroxybenzoic acid consisting of 2-hydroxybenzoic acid having nitro substituents at the 3- and 5-positions. It is used in colorimetric testing for the presence of free carbonyl groups (C=O) in reducing sugars.	2.25	1	0	C-nitro compound; monohydroxybenzoic acid	hapten
phenylglyoxylic acid phenylglyoxylic acid: styrene metabolite. phenylglyoxylic acid : A 2-oxo monocarboxylic acid that is glyoxylic acid in which the aldehyde hydrogen is substituted by a phenyl group.	2.25	1	0	2-oxo monocarboxylic acid	biomarker; human xenobiotic metabolite
2-anthramine 2-anthramine: structure	1.98	1	0	anthracenamine
2-(methylthio)benzothiazole 2-methylthio-1,3-benzothiazole : An organic sulfide that is the methyl thioether of 1,3-benzothiazole-2-thiol.	2.03	1	0	benzothiazoles; methyl sulfide	aryl hydrocarbon receptor agonist; xenobiotic metabolite
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	2.78	3	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
chorismic acid Chorismic Acid: A cyclohexadiene carboxylic acid derived from SHIKIMIC ACID and a precursor for the biosynthesis of UBIQUINONE and the AROMATIC AMINO ACIDS.. chorismic acid : The (3R,4R)-stereoisomer of 5-[(1-carboxyethenyl)oxy]-6-hydroxycyclohexa-1,3-diene-1-carboxylic acid.	2.11	1	0	5-[(1-carboxyethenyl)oxy]-6-hydroxycyclohexa-1,3-diene-1-carboxylic acid	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
5-methyl-2-furfural 5-methyl-2-furfural: RN given refers to cpd with locants as specified	2.53	2	0	aldehyde; furans	EC 2.2.1.6 (acetolactate synthase) inhibitor; flavouring agent; human metabolite; Maillard reaction product
4,4'-bisphenol f 4,4'-bisphenol F: RN given refers to parent cpd. bisphenol F : A bisphenol that is methane in which two of the hydrogens have been replaced by 4-hydroxyphenyl groups.	2.31	1	0	bisphenol; diarylmethane	environmental food contaminant; xenoestrogen
2,5-dimethylfuran 2,5-dimethylfuran: metabolite of n-hexane. 2,5-dimethylfuran : A member of the class of furans that is furan in which the hydrogens at positions 2 and 5 are replaced by methyl groups.	4.11	4	0	furans	antifungal agent; bacterial metabolite; fuel; fumigant; human urinary metabolite; Maillard reaction product; plant metabolite
hexamethylene glycol hexane-1,6-diol : A diol that is hexane substituted by hydroxy groups at positions 1 and 6.	2.31	1	0	diol; primary alcohol
c.i. 42510 Rosaniline Dyes: Compounds that contain the triphenylmethane aniline structure found in rosaniline. Many of them have a characteristic magenta color and are used as COLORING AGENTS.. basic fuchsin : A four-component mixture of chemically related dyes comprising pararosanilin, rosanilin, magenta II and new fuchsin in varying amounts. rosanilin : A hydrochloride that is the monohydrochloride of 4-[(4-aminophenyl)(4-iminocyclohexa-2,5-dien-1-ylidene)methyl]-2-methylaniline. One of the major constituents of Basic fuchsin, together with pararosanilin, magenta II and new fuchsin.	2.59	2	0
1,2,3-trimethoxybenzene 1,2,3-trimethoxybenzene : A methoxybenzene that is benzene substituted by methoxy groups at positions 1, 2 and 3 respectively.	2.03	1	0	methoxybenzenes	plant metabolite
4-hydroxyisophthalic acid 4-hydroxyisophthalic acid: structure given in first source	1.94	1	0
isovanillic acid 3-hydroxy-4-methoxybenzoic acid : A methoxybenzoic acid that is 4-methoxybenzoic acid bearing a hydroxy substituent at position 3.	2.41	2	0	methoxybenzoic acid; monohydroxybenzoic acid	antibacterial agent; plant metabolite
4-propylphenol 4-propylphenol: structure given in first source	2.11	1	0	alkylbenzene
isosorbide Isosorbide: 1,4:3,6-Dianhydro D-glucitol. Chemically inert osmotic diuretic used mainly to treat hydrocephalus; also used in glaucoma.	2.08	1	0	organic molecular entity
2,2-dichloroacetamide [no description available]	2.11	1	0
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.	1.99	1	0	N-nitrosoureas	alkylating agent; carcinogenic agent; mutagen; teratogenic agent
2,6-dichlorobenzoquinone 2,6-dichlorobenzoquinone : A member of the class of 1,4-benzoquinones that is p-benzoquinone in which the hydrogens at positions 2 and 6 have been replaced by chlorines. A highly toxic and carcinogenic disinfection by-product found in drinking water.	2.47	2	0	1,4-benzoquinones; organochlorine compound	carcinogenic agent; poison
2,3,4,5,6-pentafluorophenol 2,3,4,5,6-pentafluorophenol: RN given refers to parent cpd; structure given in first source	2.11	1	0
dimethyl phosphate dimethyl phosphate: excreted in urine after exposure to mevinphos; RN given refers to parent cpd; structure	2.11	1	0	dialkyl phosphate
acryloyl chloride [no description available]	2.1	1	0
ethyl gallate ethyl gallate: used with osmium in procedure for mapping neuronal pathways. ethyl gallate : A gallate ester obtained by the formal condensation of gallic acid with ethanol.	2.07	1	0	gallate ester	plant metabolite
4-phenoxyphenol [no description available]	2.15	1	0	phenoxyphenol
1-phenylazo-2-naphthol 1-phenylazo-2-naphthol: RN given refers to cpd without isomeric designation	2.25	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.	2.5	2	0	enoate ester	allergen; polymerisation monomer
n-methylpyrrolidone 1-methylpyrrolidin-2-one: structure in first source. N-methylpyrrolidin-2-one : A member of the class of pyrrolidine-2-ones that is pyrrolidin-2-one in which the hydrogen attached to the nitrogen is replaced by a methyl group.	2.07	1	0	lactam; N-alkylpyrrolidine; pyrrolidin-2-ones	polar aprotic solvent
dodecylamine dodecylamine: RN given refers to parent cpd	2.05	1	0	primary aliphatic amine
3-methoxycatechol 3-methoxycatechol : A member of the class of catechols that is catechol in which a hydrogen that is ortho to one of the hydroxy groups has been replaced by a methoxy group. It displays agonistic activity against G protein-coupled receptor 35 (GPR35).	7.41	1	0	aromatic ether; catechols	G-protein-coupled receptor agonist
2,6-dichloroindophenol 2,6-Dichloroindophenol: A dye used as a reagent in the determination of vitamin C.. 2,6-dichloroindophenol : A quinone imine that is indophenol substituted by chloro groups at positions 2 and 6.. N-3,5-dichloro-4-hydroxyphenyl-1,4-benzoquinone imine : 1,4-benzoquinone imine having a 3,5-dichloro-4-hydroxyphenyl substituent attached to the nitrogen atom.	2.13	1	0	dichlorobenzene; quinone imine
methylphosphonic acid methylphosphonic acid : A one-carbon compound that is phosphonic acid in which the hydrogen attached to the phosphorus is substituted by a methyl group.	2.11	1	0	one-carbon compound; phosphonic acids
2,5-dimethyltetrahydrofuran 2,5-dimethyltetrahydrofuran: structure given in first source	2.05	1	0
undecane undecane : A straight-chain alkane with 11 carbon atoms.	2.48	2	0	alkane
4-dimethylaminopyridine 4-dimethylaminopyridine: catalyst for acetylation of hydroxy cpds; structure	2.01	1	0	dialkylarylamine; tertiary amino compound
lauryl gallate [no description available]	3.59	2	0	gallate ester
ethylenediamine-n,n'-bis(2-hydroxyphenylacetic acid) ethylenediamine-N,N'-bis(2-hydroxyphenylacetic acid): synthetic iron chelator; RN given refers to parent cpd; structure in 3rd source	2.01	1	0
2-acetylfuran 2-acetylfuran : A furan carrying an acetyl substituent at the 2-position. Used in the production of the antibiotic cefuroxime (CHEBI:3515).	2.41	1	0	aromatic ketone; furans; methyl ketone
carmine Carmine: Coloring matter from the insect Coccus cacti L. It is used in foods, pharmaceuticals, toiletries, etc., as a dye, and also has use as a microscopic stain and biological marker.	2.15	1	0
calcium peroxide [no description available]	3.36	5	0	calcium oxides
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).	4.74	8	0
potassium hydroxide potassium hydroxide: RN given refers to cpd with MF of K-OH	4.33	18	0	alkali metal hydroxide
sodium hydroxide Sodium Hydroxide: A highly caustic substance that is used to neutralize acids and make sodium salts. (From Merck Index, 11th ed)	7.94	173	1	alkali metal hydroxide
manganese dioxide [no description available]	2.82	3	0	manganese molecular entity; metal oxide
zinc oxide Zinc Oxide: A mild astringent and topical protectant with some antiseptic action. It is also used in bandages, pastes, ointments, dental cements, and as a sunblock.	4.49	20	0	zinc molecular entity
ferrous sulfide ferrous sulfide: RN given refers to cpd with MF of Fe-S; mackinawite & troilite both have MF Fe-S	2.69	2	0
ammonium hydroxide Ammonium Hydroxide: The hydroxy salt of ammonium ion. It is formed when AMMONIA reacts with water molecules in solution.. ammonium hydroxide : A solution of ammonia in water.	3.66	9	0	inorganic hydroxy compound	food acidity regulator
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	2	1	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]	2.15	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.	2.6	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.	2.07	1	0	ether	fuel additive; metabolite; non-polar solvent
pyrazon pyrazon: structure; do not confuse with phenazone which is a synonym to antipyrine. chloridazon : A pyridazinone that is pyridazin-3(2H)-one substituted by an amino group at position 5, a chloro group at position 4 and a phenyl group at position 2.	2.05	1	0	benzenes; organochlorine compound; primary amino compound; pyridazinone	environmental contaminant; herbicide; xenobiotic
2,2'-biphenol biphenyl-2,2'-diol : A member of the class of hydroxybiphenyls carrying hydroxy groups at positions 2 and 2'.	1.99	1	0	hydroxybiphenyls
nitrofen nitrofen: structure	2	1	0	organic molecular entity	EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor; herbicide
stearylamine stearylamine: RN given refers to parent cpd. octadecan-1-amine : An 18-carbon primary aliphatic amine.	2.57	2	0	primary aliphatic amine	film-forming compound
tetrachloroisophthalonitrile tetrachloroisophthalonitrile: structure. chlorothalonil : A dinitrile that is benzene-1,3-dicarbonitrile substituted by four chloro groups. A non-systemic fungicide first introduced in the 1960s, it is used to control a range of diseases in a wide variety of crops.	2.25	1	0	aromatic fungicide; dinitrile; tetrachlorobenzene	antifungal agrochemical
ethylpyridinium ethylpyridinium: RN given refers to parent cpd	2.53	2	0
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.	7.05	1	0	organic cation	geroprotector; herbicide
picloram Picloram: A picolinic acid derivative that is used as a herbicide.. picloram : A pyridinemonocarboxylic acid that is pyridine-2-carboxylic acid which is substituted by a chloro group at positions 3,5 and 6, and by an amino group at position 4. It is a systemic herbicide used to control deeply rooted herbaceous weeds and woody plants in rights-of-way, forestry, range lands, pastures, and small grain crops.	2.08	1	0	aminopyridine; chloropyridine; organochlorine pesticide; pyridinemonocarboxylic acid	herbicide; synthetic auxin
tetrabutylammonium tetrabutylammonium: lipophilic probe; RN given refers to parent cpd	2.08	1	0	quaternary ammonium ion
irganox 1076 [no description available]	2.17	1	0
fluometuron fluometuron: RN given refers to parent cpd; structure. fluometuron : A member of the class of 3-(3,4-substituted-phenyl)-1,1-dimethylureas that is urea in which one of the nitrogens is substituted by a 3-(trifluoromethyl)phenyl group while the other is substituted by two methyl groups. It is a herbicide used for the control of broadleaf weeds and annual grasses in cotton.	7.01	1	0	(trifluoromethyl)benzenes; 3-(3,4-substituted-phenyl)-1,1-dimethylurea	agrochemical; environmental contaminant; herbicide; photosystem-II inhibitor; xenobiotic
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.	2.31	1	0	organic disulfide	antifungal agent; antineoplastic agent; plant metabolite
n-isopropylacrylamide N-isopropylacrylamide: can polymerize with glycidyl acrylate to form reactive water-soluble polymer that can react with the amino groups of enzymes-proteins or other ligands	2.8	3	0
dihydroconiferyl alcohol dihydroconiferyl alcohol: structure given in first source. dihydroconiferyl alcohol : A member of class of phenols that is 2-methoxyphenol substituted by a 3-hydroxypropyl group at position 4.	4.23	5	0	eugenol; primary alcohol	plant 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.	2.5	2	0	2-benzofurans; gamma-lactone; organic heteropentacyclic compound; oxaspiro compound; polyphenol; xanthene dye	fluorescent dye; radioopaque medium
ethyl violet ethyl violet: RN given refers to parent cpd. ethyl violet : An organic chloride salt that is the monochloride salt of ethyl violet cation. Used for inclusion in mixed dye solutions of the iron resorcin fuchsin type for demonstrating elastic fibres.	2.21	1	0	organic chloride salt	fluorochrome; histological dye
fucose Fucose: A six-member ring deoxysugar with the chemical formula C6H12O5. It lacks a hydroxyl group on the carbon at position 6 of the molecule.. L-fucopyranose : The pyranose form of L-fucose.. fucose : Any deoxygalactose that is deoxygenated at the 6-position.	1.94	1	0	fucopyranose; L-fucose	Escherichia coli metabolite; mouse metabolite
sulfadoxine Sulfadoxine: A long acting sulfonamide that is used, usually in combination with other drugs, for respiratory, urinary tract, and malarial infections.. sulfadoxine : A sulfonamide consisting of pyrimidine having methoxy substituents at the 5- and 6-positions and a 4-aminobenzenesulfonamido group at the 4-position. In combination with the antiprotozoal pyrimethamine (CHEBI:8673) it is used as an antimalarial.	1.96	1	0	pyrimidines; sulfonamide	antibacterial drug; antimalarial
acetosyringone acetosyringone: plant inducer which induces expression of VirE & VirG in A. tumefaciens. acetosyringone : A member of the class of acetophenones that is 1-phenylethanone substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5.	8.34	6	0	acetophenones; dimethoxybenzene; phenols	anti-asthmatic drug; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug; plant metabolite
c.i. direct blue 1 [no description available]	2.43	2	0
dispersion yellow 3 Dispersion Yellow 3: used in carpet industry; river pollutant. 4-(2-hydroxy-5-methylphenylazo)acetanilide : An azo dye with a structure consisting of acetanilide substituted on the 4-position of the phenyl group with a 6-hydroxy-m-tolylazo group.	1.98	1	0
2-(dimethylamino)ethyl methacrylate 2-(dimethylamino)ethyl methacrylate: reducing agent; structure given in first source	7.41	1	0
glycidyl trimethylammonium chloride glycidyl trimethylammonium: causes dermatitis on contact; structure given in first source; RN given refers to chloride	2.21	1	0
1,3,4-butanetriol 1,2,4-butanetriol: structure in first source. 1,2,4-butanetriol : A triol that is butane carrying three hydroxy substituents at position 1, 2 and 4.	2.61	2	0	triol	bacterial xenobiotic metabolite; Escherichia coli metabolite
sudan red [no description available]	2.6	1	0
methional [no description available]	1.96	1	0	aliphatic sulfide	prostaglandin antagonist
2,2-bis(bromomethyl)-1,3-propanediol 2,2-bis(bromomethyl)-1,3-propanediol: structure given in first source	2.41	1	0	primary alcohol
fluorescein-5-isothiocyanate Fluorescein-5-isothiocyanate: Fluorescent probe capable of being conjugated to tissue and proteins. It is used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.. fluorescein 5-isothiocyanate : The 5-isomer of fluorescein isothiocyanate. Acts as a fluorescent probe capable of being conjugated to tissue and proteins; used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.	3.03	4	0	fluorescein isothiocyanate
levanol fast cyanine 5rn Levanol Fast Cyanine 5RN: RN given refers to parent cpd	2.11	1	0
sabinene sabinene: RN given refers to cpd without isomeric designation. sabinene : A thujene that is a bicyclic monoterpene isolated from the essential oils of various plant species.	5.7	24	0	thujene	plant metabolite
2,3-diketogulonic acid 2,3-Diketogulonic Acid: Metabolite of ASCORBIC ACID and the oxidized form of the lactone DEHYDROASCORBIC ACID.. 2,3-diketogulonic acid : A carbohydrate acid formally derived from gulonic acid by oxidation of the -OH groups at positions 2 and 3 to keto groups.	2.03	1	0
mannose mannopyranose : The pyranose form of mannose.	4.53	23	0	D-aldohexose; D-mannose; mannopyranose	metabolite
dithiothreitol 1,4-dimercaptobutane-2,3-diol : A glycol that is butane-2,3-diol in which a hydrogen from each of the methyl groups is replaced by a thiol group.. 1,4-dithiothreitol : The threo-diastereomer of 1,4-dimercaptobutane-2,3-diol.	2.72	3	0	1,4-dimercaptobutane-2,3-diol; butanediols; dithiol; glycol; thiol	chelator; human metabolite; reducing agent
phenoxyacetic acid phenoxyacetic acid : A monocarboxylic acid that is the O-phenyl derivative of glycolic acid. A metabolite of 2-phenoxyethanol, it is used in the manufacture of pharmaceuticals, pesticides, fungicides and dyes.	3.36	6	0	aromatic ether; monocarboxylic acid	allergen; Aspergillus metabolite; human xenobiotic metabolite; plant growth retardant
nafenopin Nafenopin: A peroxisome proliferator that is used experimentally to promote liver tumors. It has been used as an antihyperlipoproteinemic agent.. nafenopin : A racemate comprising equimolar amounts of (R)- and (S)-nafenopin. It is a peroxisome proliferator that is used experimentally to promote liver tumors. It has been used as an hypolipidemic agent.. 2-methyl-2-[4-(1,2,3,4-tetrahydronaphthalen-1-yl)phenoxy]propanoic acid : A monocarboxylic acid that is 2-hydroxy-2-methylpropanoic acid in which ther tertiary hydroxy group has been converted into the corresponding p-(1,2,3,4-tetrahydronaphthalen-1-yl)phenyl ether.	3.04	1	0	aromatic ether; monocarboxylic acid
streptomycin [no description available]	2.41	1	0	antibiotic antifungal drug; antibiotic fungicide; streptomycins	antibacterial drug; antifungal agrochemical; antimicrobial agent; antimicrobial drug; bacterial metabolite; protein synthesis inhibitor
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.	5.53	20	0	carbon oxoanion
3-chloro-4-hydroxybenzoate [no description available]	1.99	1	0
isopropyl glycidyl ether isopropyl glycidyl ether: RN & structure given in first source	2.03	1	0
promethazine 1,3-dimethylimidazolium: structure in first source. 1,3-dimethylimidazolium : A 1-alkyl-3-methylimidazolium in which the alkyl substituent at C-1 is methyl.	2.11	1	0	1-alkyl-3-methylimidazolium
direct blue 71 Direct Blue 71: structure in first source	2.15	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.	2.48	2	0	diastereoisomeric mixture; homocysteines; non-proteinogenic alpha-amino acid; sulfoximide	EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor; ferroptosis inducer
trioctylmethylammonium trioctylmethylammonium: used in high performance liquid chromatography for the separation of tRNA; RN given refers to chloride. methyltrioctylammonium : A quaternary ammonium ion with three octyl groups and one methyl group attached to the nitrogen.	2.63	2	0	quaternary ammonium ion
brilliant crocein brilliant crocein: structure in first source. woodstain scarlet : An organic sodium salt that is the disodium salt of 7-hydroxy-8-{[4-(phenyldiazenyl)phenyl]diazenyl}naphthalene-1,3-disulfonic acid. Occasionally used for the demonstration of muscle fibres in conjunction with, or as a replacement for, acid fuchsin.	2.31	1	0	organic sodium salt	histological dye
octylmethoxycinnamate octylmethoxycinnamate: a sunscreen used for prevention of DNA photodamage	2.41	1	0	cinnamate ester
1-nitropyrene [no description available]	2.02	1	0	nitroarene	carcinogenic agent
chlorpyrifos-methyl chlorpyrifos-methyl : An organic thiophosphate that is O,O-dimethyl hydrogen phosphorothioate in which the hydrogen of the hydroxy group has been replaced by a 3,5,6-trichloropyridin-2-yl group.	2.13	1	0	chloropyridine; organic thiophosphate	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; environmental contaminant; insecticide; xenobiotic
iodinated glycerol iodinated glycerol: secretolytic agent; RN given refers to cpd without iodine locant	2.25	1	0	dioxolane
terbutylazine terbutylazine : A diamino-1,3,5-triazine that is N-tert-butyl-N'-methyl-1,3,5-triazine-2,4-diamine substituted by a chloro group at position 6.	2.01	1	0	chloro-1,3,5-triazine; diamino-1,3,5-triazine	environmental contaminant; herbicide; xenobiotic
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.	7.63	2	0	cycloalkene; p-menthadiene	human metabolite
ammonium nitrate ammonium nitrate: structure. ammonium nitrate : The ammonium salt of nitric acid.	2.97	4	0	ammonium salt; inorganic molecular entity; inorganic nitrate salt	explosive; fertilizer; oxidising agent
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.	1.95	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.	2.51	2	0	cobalt group element atom; platinum group metal atom
lanthanum [no description available]	8.46	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.	7.14	66	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.	5.25	15	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.	4.27	15	0	chromium group element atom	micronutrient
niobium Niobium: A metal element atomic number 41, atomic weight 92.906, symbol Nb.	2.82	3	0	vanadium group element 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.	4.32	17	0	metal allergen; nickel group element atom; platinum group metal atom
platinum Platinum: A heavy, soft, whitish metal, resembling tin, with atomic number 78, atomic weight 195.084, symbol Pt. It is used in manufacturing equipment for laboratory and industrial use. It occurs as a black powder (platinum black) and as a spongy substance (spongy platinum) and may have been known in Pliny's time as alutiae.	3.98	12	0	elemental platinum; nickel group element atom; platinum group metal atom
rhenium Rhenium: A metal, atomic number 75, atomic weight 186.207, symbol Re.	7.57	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.	7.13	1	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.	4.3	17	0	iron group element atom; platinum group metal 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.	2.1	1	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.	6.43	47	0	copper group element atom; elemental silver	Escherichia coli metabolite
terbium Terbium: An element of the rare earth family of metals. It has the atomic symbol Tb, atomic number 65, and atomic weight 158.92.	2.1	1	0	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.	4.89	32	0	titanium group element atom
tungsten Tungsten: A metallic element with the atomic symbol W, atomic number 74, and atomic weight 183.85. It is used in many manufacturing applications, including increasing the hardness, toughness, and tensile strength of steel; manufacture of filaments for incandescent light bulbs; and in contact points for automotive and electrical apparatus.	3.88	3	0	chromium group element atom	micronutrient
argon Argon: A noble gas with the atomic symbol Ar, atomic number 18, and atomic weight 39.948. It is used in fluorescent tubes and wherever an inert atmosphere is desired and nitrogen cannot be used.	2.81	3	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.	6.6	58	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.	3.56	7	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.	6.89	50	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.	2.11	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.	2.03	1	0	f-block element atom; lanthanoid atom
gold Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.	5.81	15	0	copper group element atom; elemental gold
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.	2.83	3	0	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.	4.58	7	0	elemental vanadium; vanadium group element atom	micronutrient
zirconium Zirconium: A rather rare metallic element with atomic number 40, atomic weight 91.224, and symbol Zr.	3.5	7	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.	8.34	6	0	aluminium coordination entity	Lewis acid
magnesium sulfate Magnesium Sulfate: A small colorless crystal used as an anticonvulsant, a cathartic, and an electrolyte replenisher in the treatment of pre-eclampsia and eclampsia. It causes direct inhibition of action potentials in myometrial muscle cells. Excitation and contraction are uncoupled, which decreases the frequency and force of contractions. (From AMA Drug Evaluations Annual, 1992, p1083). magnesium sulfate : A magnesium salt having sulfate as the counterion.	2.7	3	0	magnesium salt; metal sulfate; organic magnesium salt	anaesthetic; analgesic; anti-arrhythmia drug; anticonvulsant; calcium channel blocker; cardiovascular drug; fertilizer; tocolytic agent
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.	2.08	1	0	mercury coordination entity	sensitiser
acetylglucosamine Acetylglucosamine: The N-acetyl derivative of glucosamine.. N-acetyl-beta-D-glucosamine : An N-acetyl-D-glucosamine having beta-configuration at the anomeric centre.	2.1	1	0	N-acetyl-D-glucosamine	epitope
phosphoric acid, trisodium salt [no description available]	2.13	1	0	sodium phosphate
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.	2.17	1	0	inorganic caesium salt; inorganic chloride	phase-transfer catalyst; vasoconstrictor agent
hypochlorous acid Hypochlorous Acid: An oxyacid of chlorine (HClO) containing monovalent chlorine that acts as an oxidizing or reducing agent.. hypochlorous acid : A chlorine oxoacid with formula HOCl; a weak, unstable acid, it is the active form of chlorine in water.	2.85	3	0	chlorine oxoacid; reactive oxygen species	EC 2.5.1.18 (glutathione transferase) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; human 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	9.02	12	0	iron coordination entity	astringent; Lewis acid
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.	2.7	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.	1.98	1	0	mononuclear parent hydride; phosphanes; phosphine	carcinogenic agent; fumigant insecticide
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.	6.98	1	0	diatomic bromine
zinc sulfate Zinc Sulfate: A compound given in the treatment of conditions associated with zinc deficiency such as acrodermatitis enteropathica. Externally, zinc sulfate is used as an astringent in lotions and eye drops. (Reynolds JEF(Ed): Martindale: The Extra Pharmacopoeia (electronic version). Micromedex, Inc, Englewood, CO, 1995). zinc sulfate : A metal sulfate compound having zinc(2+) as the counterion.	2.8	3	0	metal sulfate; zinc molecular entity	fertilizer
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.	2.11	1	0	inorganic nitrate salt; potassium salt	fertilizer
sodium sulfate [no description available]	5.76	5	1	inorganic sodium salt
sodium sulfite [no description available]	3.94	12	0	inorganic sodium salt; sulfite salt	food preservative; reducing agent
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.	7.6	1	0	calcium phosphate
lead chloride lead chloride: RN in 9th CI Form Index for cotunnite: 14639-87-3; RN given refers to cpd with MF of Pb-Cl2. lead(II) chloride : An inorganic chloride consisting of two chlorine atoms covalently bound to a central lead atom.	2.25	1	0	inorganic chloride; lead coordination entity
chromates Chromates: Salts of chromic acid containing the CrO(2-)4 radical.. chromate(2-) : A chromium oxoanion resulting from the removal of two protons from chromic acid.	1.94	1	0	chromium oxoanion; divalent inorganic anion	oxidising agent
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.	3.7	9	0	metal sulfate	emetic; fertilizer; sensitiser
tungstate [no description available]	2.21	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.	1.97	1	0	inorganic nitrate salt; silver salt	astringent
sodium thiosulfate sodium thiosulfate: do not confuse synonym sodium hyposulfite with sodium hyposulfite, synonym for di-Na salt of dithionous acid. sodium thiosulfate : An inorganic sodium salt composed of sodium and thiosulfate ions in a 2:1 ratio.	2.11	1	0	inorganic sodium salt	antidote to cyanide poisoning; antifungal drug; nephroprotective agent
calcium sulfate Calcium Sulfate: A calcium salt that is used for a variety of purposes including: building materials, as a desiccant, in dentistry as an impression material, cast, or die, and in medicine for immobilizing casts and as a tablet excipient. It exists in various forms and states of hydration. Plaster of Paris is a mixture of powdered and heat-treated gypsum.	2.77	3	0	calcium salt; inorganic calcium salt
calcium hypochlorite calcium hypochlorite: structure	2.05	1	0	calcium salt; inorganic calcium salt	bleaching agent
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	9.03	14	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.	4.57	24	0	diatomic chlorine; gas molecular entity	bleaching agent
silver chloride [no description available]	2.11	1	0	inorganic chloride; silver salt
deuterium oxide Deuterium Oxide: The isotopic compound of hydrogen of mass 2 (deuterium) with oxygen. (From Grant & Hackh's Chemical Dictionary, 5th ed) It is used to study mechanisms and rates of chemical or nuclear reactions, as well as biological processes.	2.01	1	0	deuterated compound; water	NMR solvent
fluorosulfonic acid perfluorosulfonic acid: sulfonated tetrafluoroethylene-based fluoropolymer–copolymer	2.58	2	0	sulfur oxoacid	NMR solvent
molybdate ion molybdate : A divalent inorganic anion obtained by removal of both protons from molybdic acid	2.54	2	0	divalent inorganic anion; molybdenum oxoanion	Escherichia coli metabolite
calcium lignosulfonate [no description available]	4.27	17	0
galactose aldohexose : A hexose with a (potential) aldehyde group at one end.	6.95	28	0
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.	7.13	62	0	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
hydroiodic acid hydrogen iodide : A diatomic molecule containing covalently bonded hydrogen and iodine atoms.	2.07	1	0	gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
aluminum sulfate aluminium sulfate (anhydrous) : An aluminium sulfate that contains no water of crystallisation.	2.99	4	0	aluminium sulfate
chlorine dioxide chlorine dioxide: equal or superior to chlorine when used as wastewater disinfectant	3.81	9	0	chlorine dioxide
lead nitrate lead nitrate: RN given refers to unspecified lead nitrate	2.02	1	0	inorganic nitrate salt; lead coordination entity
tellurous acid tellurous acid: tellurite anion inhibits oxidation of NAD-linked substrates in kidney & liver mitochondria; RN given refers to parent cpd	2.41	1	0	tellurium oxoacid
cadmium chloride Cadmium Chloride: A cadmium halide in the form of colorless crystals, soluble in water, methanol, and ethanol. It is used in photography, in dyeing, and calico printing, and as a solution to precipitate sulfides. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). cadmium dichloride : A cadmium coordination entity in which cadmium(2+) and Cl(-) ions are present in the ratio 2:1. Although considered to be ionic, it has considerable covalent character to its bonding.	2.8	3	0	cadmium coordination entity
calcium nitrate calcium nitrate: an amylopsin activator. calcium nitrate : Inorganic nitrate salt of calcium.	2.17	1	0	calcium salt; inorganic nitrate salt	fertilizer
rhamnose [no description available]	2.9	4	0	L-rhamnose
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.	2.51	2	0	ammonium salt; inorganic chloride	ferroptosis inhibitor
ancymidol ancymidol : A tertiary alcohol that is methanol in which the hydrogens attached to the carbon are replaced by cyclopropyl, p-methoxyphenyl and pyrimidin-5-yl groups. By inhibiting gibberellin biosynthesis, ancymidol reduces plant growth, resulting in reduced internode elongation and thus more compact plants. It is used in the commercial production of a wide variety of container-grown bedding and foliage plants, including chrysanthemums, Easter lilies and poinsettias.	2.03	1	0	pyrimidines; tertiary alcohol	cellulose synthesis inhibitor; gibberellin biosynthesis inhibitor; plant growth retardant
procion blue mx-r procion blue MX-R: used in affinity labeling of enzymes; RN given refers to parent cpd	7.46	2	0
2',3-dimethyl-4-aminobiphenyl 2',3-dimethyl-4-aminobiphenyl: RN given refers to parent cpd; structure	1.96	1	0
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.	12.01	22	1	titanium oxides	food colouring
salen disalicylaldehyde ethylenediamine: reagents for determination of iron	2.74	3	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.	2.11	1	0
2,4',5-trichlorobiphenyl [no description available]	1.99	1	0
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.	2.73	3	0	phosphonic acids	plant growth regulator
benomyl [no description available]	2	1	0	aromatic amide; benzimidazole fungicide; benzimidazoles; benzimidazolylcarbamate fungicide; carbamate ester	acaricide; anthelminthic drug; antifungal agrochemical; microtubule-destabilising agent; tubulin modulator
reactive red 2 reactive red 2: inhibitor of ecto-nucleotidase and P(2y)-selective purinoceptor antagonist; structure in first source. procion red MX-5B : A 2,4-dichloro-1,3,5-triazine with a multi-substituted napthalen-1-ylamino substituent at the 6-position.	2.45	2	0
chromium chromium hexavalent ion: a human respiratory carcinogen	5.93	28	0	chromium cation; monoatomic hexacation
brilliant orange 3r brilliant orange 3R: RN given refers to di-Na salt; RN for parent cpd not avail 11/92; structure given in first source	2.04	1	0
reactive orange [no description available]	2.43	2	0
iodine [no description available]	8.08	4	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.	2.08	1	0	osmium coordination entity	fixative; histological dye; oxidising agent; poison
metribuzin metribuzin : A member of the class of 1,2,4-triazines that is 1,2,4-triazin-5(4H)-one substituted by an amino group at position 4, tert-butyl group at position 6 and a methylsulfanyl group at position 3.	7.05	1	0	1,2,4-triazines; cyclic ketone; organic sulfide	agrochemical; environmental contaminant; herbicide; xenobiotic
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.	7.34	79	0	benzenes; phenyl acetates
phenoxyethanol phenoxyethanol: structure. 2-phenoxyethanol : An aromatic ether that is phenol substituted on oxygen by a 2-hydroxyethyl group.	2.72	2	0	aromatic ether; glycol ether; primary alcohol	antiinfective agent; central nervous system depressant
cetylpyridinium chloride anhydrous tserigel: according to first source contains polyvinylbutyral & cetylpyridinium chloride; UD only lists cetylpyridinium chloride as constituent. cetylpyridinium chloride : A pyridinium salt that has N-hexadecylpyridinium as the cation and chloride as the anion. It has antiseptic properties and is used in solutions or lozenges for the treatment of minor infections of the mouth and throat.	3.19	1	0	chloride salt; organic chloride salt	antiseptic drug; surfactant
4-ethylphenol 4-ethylphenol: RN given refers to parent cpd. 4-ethylphenol : A member of the class of phenols carrying an ethyl substituent at position 4.	7.49	2	0	phenols	fungal xenobiotic metabolite
4-anisaldehyde 4-anisaldehyde: RN given refers to cpd with specified locants for methoxy moieties; structure in Merck, 9th ed, #696. p-methoxybenzaldehyde : A member of the class of benzaldehydes consisting of benzaldehyde itself carrying a methoxy substituent at position 4.	2.39	2	0	benzaldehydes	bacterial metabolite; human urinary metabolite; insect repellent; plant metabolite
acetylacetone acetylacetone : A beta-diketone that is pentane in which the hydrogens at positions 2 and 4 are replaced by oxo groups.	2.17	1	0	beta-diketone
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.	3.87	11	0	dioxane; volatile organic compound	carcinogenic agent; metabolite; NMR chemical shift reference compound; non-polar solvent
sulfolane sulfolane : A member of the class of tetrahydrothiophenes that is tetrahydrothiophene in which the sulfur has been oxidised to give the corresponding sulfone. A colourless, high-boiling (285degreeC) liquid that is miscible with both water and hydrocarbons, it is used as an industrial solvent, particularly for the purification of hydrocarbon mixtures by liquid-vapour extraction.	7.25	1	0	sulfone; tetrahydrothiophenes	polar aprotic solvent
tris(2,3-dibromopropyl)phosphate tris(2,3-dibromopropyl)phosphate: flame retardant	2.1	1	0	trialkyl phosphate
dimethylacetamide hallucinogen : Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations and other alterations of mood and thinking.. N,N-dimethylacetamide : A member of the class of acetamides that is acetamide in which the hydrogens attached to the N atom have been replaced by two methyl groups respectively. Metabolite observed in cancer metabolism.	7.44	2	0	acetamides; monocarboxylic acid amide	human metabolite
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.	3.16	5	0	ortho- and peri-fused polycyclic arene	fluorescent probe; persistent organic pollutant
benzonidazole benzonidazole: used in treatment of Chagas' disease. benznidazole : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2-nitroimidazol-1-yl)acetic acid with the aromatic amino group of benzylamine. Used for treatment of Chagas disease.	2.6	1	0	C-nitro compound; imidazoles; monocarboxylic acid amide	antiprotozoal drug
transferrin Transferrin: An iron-binding beta1-globulin that is synthesized in the LIVER and secreted into the blood. It plays a central role in the transport of IRON throughout the circulation. A variety of transferrin isoforms exist in humans, including some that are considered markers for specific disease states.	2.01	1	0
alkenes [no description available]	10.44	17	0
calcium oxalate Calcium Oxalate: The calcium salt of oxalic acid, occurring in the urine as crystals and in certain calculi.. calcium oxalate : The calcium salt of oxalic acid, which in excess in the urine may lead to formation of oxalate calculi (kidney stones).	2.41	1	0	organic calcium salt
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	3.23	5	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
glucaric acid Glucaric Acid: A sugar acid derived from D-glucose in which both the aldehydic carbon atom and the carbon atom bearing the primary hydroxyl group are oxidized to carboxylic acid groups.. D-glucaric acid : The D-enantiomer of glucaric acid.. glucaric acid : A hexaric acid derived by oxidation of sugar such as glucose with nitric acid.	2.21	1	0	glucaric acid	antineoplastic agent
poly-n,n-dimethyl-n,n-diallylammonium chloride diallyldimethylammonium chloride: structure in first source	3	4	0
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).	2.41	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.	3.24	6	0	pseudohalide anion	mitochondrial respiratory-chain inhibitor
halofenate Halofenate: An antihyperlipoproteinemic agent and uricosuric agent.	3.04	1	0
amoxicillin Amoxicillin: A broad-spectrum semisynthetic antibiotic similar to AMPICILLIN except that its resistance to gastric acid permits higher serum levels with oral administration.. amoxicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-(4-hydroxyphenyl)acetamido group.	2.11	1	0	penicillin allergen; penicillin	antibacterial drug
trimethylethylammonium trimethylethylammonium: RN given refers to parent cpd. ethyltrimethylammonium : A quarternary ammonium cation having one ethyl and three methyl substituents around the central nitrogen.	2.72	2	0	quaternary ammonium ion
zidovudine Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.	2.45	2	0	azide; pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	7.31	1	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
2-nitrobenzofuran [no description available]	2.08	1	0
isoproturon isoproturon : A member of the class of phenylureas that is 1,1-dimethylurea substituted by a p-cumenyl group at position 3. A selective, systemic herbicide used to control annual grasses and broadleaf weeds in cereals, its use within the EU has been banned after September 2017 on the grounds of potential groundwater contamination and risks to aquatic life; there have also been concerns about its endocrine-disrupting properties.	7.79	3	0	3-(3,4-substituted-phenyl)-1,1-dimethylurea	agrochemical; environmental contaminant; herbicide; xenobiotic
2-amino-4,6-dinitrotoluene 2-amino-4,6-dinitrotoluene : An amino-nitrotoluene that is 4,6-dinitrotoluene substituted at position 2 by an amino group.	7	1	0	amino-nitrotoluene	explosive; fungal xenobiotic metabolite
ribavirin Rebetron: Rebetron is tradename	7.6	1	0	1-ribosyltriazole; aromatic amide; monocarboxylic acid amide; primary carboxamide	anticoronaviral agent; antiinfective agent; antimetabolite; antiviral agent; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
amikacin Amikacin: A broad-spectrum antibiotic derived from KANAMYCIN. It is reno- and oto-toxic like the other aminoglycoside antibiotics.. amikacin : An amino cyclitol glycoside that is kanamycin A acylated at the N-1 position by a 4-amino-2-hydroxybutyryl group.	4.9	1	1	alpha-D-glucoside; amino cyclitol glycoside; aminoglycoside; carboxamide	antibacterial drug; antimicrobial agent; nephrotoxin
ng-nitroarginine methyl ester NG-Nitroarginine Methyl Ester: A non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.	2.31	1	0	alpha-amino acid ester; L-arginine derivative; methyl ester; N-nitro compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor
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).	1.99	1	0
decamethrin decamethrin: pyrethroid insecticide; RN given refers to cpd without isomeric designation; structure	2.08	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
metalaxyl metalaxyl: RN given refers to (DL-Ala)-isomer. metalaxyl : A racemate comprising equal amounts of (R)- and (S)-metalaxyl. A systemic fungicide, it is active against phytopathogens of the order Peronosporales and is used to conrtrol Pythium in a number of vegetable crops.. methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate : An alanine derivative that is methyl alaninate in which one of the hydrogens attached to the nitrogen is substituted by a methoxyacetyl group, while the other is substituted by a 2,6-dimethylphenyl group.	2.01	1	0	alanine derivative; aromatic amide; carboxamide; ether; methyl ester
paroxetine Paroxetine: A serotonin uptake inhibitor that is effective in the treatment of depression.. paroxetine : A benzodioxole that consists of piperidine bearing 1,3-benzodioxol-5-yloxy)methyl and 4-fluorophenyl substituents at positions 3 and 4 respectively; the (3S,4R)-diastereomer. Highly potent and selective 5-HT uptake inhibitor that binds with high affinity to the serotonin transporter (Ki = 0.05 nM). Ki values are 1.1, 350 and 1100 nM for inhibition of [3H]-5-HT, [3H]-l-NA and [3H]-DA uptake respectively. Displays minimal affinity for alpha1-, alpha2- or beta-adrenoceptors, 5-HT2A, 5-HT1A, D2 or H1 receptors at concentrations below 1000 nM, however displays weak affinity for muscarinic ACh receptors (Ki = 42 nM). Antidepressant and anxiolytic in vivo.	2.21	1	0	aromatic ether; benzodioxoles; organofluorine compound; piperidines	antidepressant; anxiolytic drug; hepatotoxic agent; P450 inhibitor; serotonin uptake inhibitor
captopril Captopril: A potent and specific inhibitor of PEPTIDYL-DIPEPTIDASE A. It blocks the conversion of ANGIOTENSIN I to ANGIOTENSIN II, a vasoconstrictor and important regulator of arterial blood pressure. Captopril acts to suppress the RENIN-ANGIOTENSIN SYSTEM and inhibits pressure responses to exogenous angiotensin.. captopril : A L-proline derivative in which L-proline is substituted on nitrogen with a (2S)-2-methyl-3-sulfanylpropanoyl group. It is used as an anti-hypertensive ACE inhibitor drug.	2.08	1	0	alkanethiol; L-proline derivative; N-acylpyrrolidine; pyrrolidinemonocarboxylic acid	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
4-(n-methyl-n-nitrosamino)-1-(3-pyridyl)-1-butanone 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone: structure; from tobacco smoke	2.11	1	0	nitrosamine; pyridines
cyromazine cyromazine: RN given refers to parent cpd	2.05	1	0	triamino-1,3,5-triazine	mouse metabolite; triazine insecticide
lovastatin Lovastatin: A fungal metabolite isolated from cultures of Aspergillus terreus. The compound is a potent anticholesteremic agent. It inhibits 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It also stimulates the production of low-density lipoprotein receptors in the liver.. lovastatin : A fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as Aspergillus terreus and Pleurotus ostreatus (oyster mushroom).	2.07	1	0	delta-lactone; fatty acid ester; hexahydronaphthalenes; polyketide; statin (naturally occurring)	anticholesteremic drug; antineoplastic agent; Aspergillus metabolite; prodrug
imazaquin imazaquin: RN given refer to parent cpd. imazaquin : A racemate comprising equimolar amounts of (R)- and (S)-imazaquin. It is a pre- and post-emergence herbicide used for the control of grasses and broad-leaved weeds.. 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid : A quinolinemonocarboxylic acid that is quinoline-3-carboxylic acid which is substituted by a 4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl group at position 2.	7.02	1	0	imidazolone; monocarboxylic acid; quinolinemonocarboxylic acid
cilazapril, anhydrous Cilazapril: One of the ANGIOTENSIN-CONVERTING ENZYME INHIBITORS (ACE inhibitors) used for hypertension. It is a prodrug that is hydrolyzed after absorption to its main metabolite cilazaprilat.. cilazapril : A pyridazinodiazepine resulting from the formal condensation of the carboxy group of cilazaprilat with ethanol. It is a drug used in the treatment of hypertension and heart failure.	2.25	1	0	dicarboxylic acid monoester; ethyl ester; pyridazinodiazepine	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; prodrug
irinotecan [no description available]	2.6	1	0	carbamate ester; delta-lactone; N-acylpiperidine; pyranoindolizinoquinoline; ring assembly; tertiary alcohol; tertiary amino compound	antineoplastic agent; apoptosis inducer; EC 5.99.1.2 (DNA topoisomerase) inhibitor; prodrug
valsartan Valsartan: A tetrazole derivative and ANGIOTENSIN II TYPE 1 RECEPTOR BLOCKER that is used to treat HYPERTENSION.. valsartan : A monocarboxylic acid amide consisting of L-valine in which the amino hydrogens have been replaced by a pentanoyl and a [2'-(1H-tetrazol-5-yl)biphenyl]-4-yl]methyl group. It exhibits antihypertensive activity.	7.31	1	0	biphenylyltetrazole; monocarboxylic acid amide; monocarboxylic acid	angiotensin receptor antagonist; antihypertensive agent; environmental contaminant; xenobiotic
tertiary-amyl methyl ether tertiary-amyl methyl ether: structure given in first source	2.07	1	0
formamidine sulfinic acid formamidine sulfinic acid: a reducing agent	2.1	1	0
sodium molybdate(vi) sodium molybdate(VI): RN given refers to molybdic acid, di-Na salt. sodium molybdate (anhydrous) : An inorganic sodium salt having molybdate as the counterion.	2.21	1	0	inorganic sodium salt	poison
gadolinium chloride gadolinium chloride: a macrophage inhibitor; reduces pulmonary injury and inflammatory mediator production induced by inhaled ozone	2.03	1	0	gadolinium coordination entity	TRP channel blocker
monoammonium molybdate ammonium molybdate: RN given refers to unspecified ammonium molybdate salt. ammonium molybdate : An ammonium salt composed of ammonium and molybdate ions in a 2:1 ratio.	2.17	1	0	ammonium salt	poison
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.	2.05	1	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
dimethylhydrazines Dimethylhydrazines: Hydrazines substituted with two methyl groups in any position.	2.37	2	0
2-amino-3,8-dimethylimidazo(4,5-f)quinoxaline 2-amino-3,8-dimethylimidazo(4,5-f)quinoxaline: strong mutagen found in broiled foods; structure given in first source. MeIQx : An imidazoquinoxaline that is 3H-imidazo[4,5-f]quinoxaline substituted at positions 3 and 8 by methyl groups and at position 2 by an amino group. A mutagenic compound found in cooked beef.	1.98	1	0	aromatic amine; imidazoquinoxaline	carcinogenic agent; genotoxin; Maillard reaction product; mutagen
acridine orange Acridine Orange: A cationic cytochemical stain specific for cell nuclei, especially DNA. It is used as a supravital stain and in fluorescence cytochemistry. It may cause mutations in microorganisms.. acridine orange : Fluorescent dye useful for cell cycle determination. It is cell-permeable, and interacts with DNA and RNA by intercalation or electrostatic attractions respectively.. acridine orange free base : A member of the class of aminoacridines that is acridine carrying two dimethylamino substituents at positions 3 and 6. The hydrochloride salt is the fluorescent dye 'acridine orange', used for cell cycle determination.	2.04	1	0	aminoacridines; aromatic amine; tertiary amino compound	fluorochrome; histological dye
vanillyl alcohol vanillyl alcohol: structure. vanillyl alcohol : A monomethoxybenzene that is 2-methoxyphenol substituted by a hydroxymethyl group at position 4.	3.46	7	0	benzyl alcohols; guaiacols	plant metabolite
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.	2.17	1	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.	2.52	2	0	one-carbon compound; perfluoroalkanesulfonic acid
4-vinylphenol 4-vinylphenol: RN given refers to cpd with locants as specified. 4-hydroxystyrene : A member of the class of phenols that is styrene carrying a hydroxy substituent at position 4.	7.77	3	0	phenols	human urinary metabolite; human xenobiotic metabolite
4-ethylguaiacol 4-ethylguaiacol: a constituent of wood creosote; suppresses intestinal smooth muscle contraction	2.11	1	0	methoxybenzenes; phenols
glycerol 1,3-diglycidyl ether glycerol 1,3-diglycidyl ether: structure given in first source	2.31	1	0
ammonium peroxydisulfate ammonium persulfate : An inorganic ammonium salt in which two of the terminal hydroxy groups of peroxydisulfuric acid are deprotonated and associated with ammonium ions as counter-cations.	2.41	1	0
potassium phosphate potassium phosphate: used in dental materials and to treat hypophosphatemia; RN given refers to cpd with unspecified MF. tripotassium phosphate : An inorganic potassium salt that is the tripotassium salt of phosphoric acid.	2.55	2	0	inorganic phosphate salt; inorganic potassium salt
caloreen caloreen: glucose polymer with average length of five glucose units for dietary energy supplement. dextrin : Glucans produced by the hydrolysis of starch or glycogen. They are mixtures of polymers of D-glucose units linked by alpha(1->4) or alpha(1->6) glycosidic bonds.	3.4	6	0
urea formaldehyde foam urea formaldehyde foam: widely used foam insulation	2.25	1	0
2-amino-9h-pyrido(2,3-b)indole 2-amino-9H-pyrido(2,3-b)indole: pyrolysis product of soybean globulins; RN given refers to unlabeled cpd; structure	2.03	1	0	pyridoindole
trazodone hydrochloride Triticum: A plant genus of the family POACEAE that is the source of EDIBLE GRAIN. A hybrid with rye (SECALE CEREALE) is called TRITICALE. The seed is ground into FLOUR and used to make BREAD, and is the source of WHEAT GERM AGGLUTININS.. trazodone hydrochloride : A hydrochloride salt prepared from equimolar amounts of trazodone and hydrogen chloride.	11.78	483	1	hydrochloride	adrenergic antagonist; antidepressant; H1-receptor antagonist; sedative; serotonin uptake inhibitor
aluminum phosphate aluminum phosphate: gel used as immunologic adjuvent; RN given refers to Al salt	2.13	1	0
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.	10.33	54	1	D-glucopyranose	epitope; mouse metabolite
dihydrochalcone dihydrochalcone : A member of the class of dihydrochalcones that is acetophenone in which one of the hydrogens of the methyl group is replaced by a benzyl group.	2.03	1	0	dihydrochalcones	plant metabolite
irganox 1010 pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate): has antioxidant activity	2.17	1	0
ursolic acid [no description available]	7.75	3	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	geroprotector; plant metabolite
epigallocatechin gallate epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis). (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin.	2.01	1	0	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
fluorexon fluorexon: structure	2.07	1	0	xanthene dye	fluorochrome
phosphoramidic acid phosphoramidic acid: urease inhibitor; RN given refers to parent cpd; structure; do not confuse with phosphoramidites, which are organophosphorus compounds	2.31	1	0	phosphoric acid derivative
metaperiodate Periodic Acid: A strong oxidizing agent.	2.68	3	0	iodine oxoacid
2-acrylamido-2-methylpropanesulfonate 2-acrylamido-2-methylpropanesulfonate: for detection of alkaline phosphatase; RN given refers to parent cpd; do not confuse with AMPS cpd	2.25	1	0	organosulfonic acid
secoisolariciresinol secoisolariciresinol: RN given refers to ((R-(R,R))-isomer); RN for cpd without isomeric designation not available 8/89; precursor of lignans found in human urine; structure given in first source. secoisolariciresinol : A lignan that is butane-1,4-diol in which the 2 and 3 positions are substituted by 4-hydroxy-3-methoxybenzyl groups. (-)-secoisolariciresinol : An enantiomer of secoisolariciresinol having (-)-(2R,3R)-configuration.	4.03	14	0	secoisolariciresinol	antidepressant; phytoestrogen; plant metabolite
glucose-1-phosphate glucose-1-phosphate: RN given refers to (alpha-D-Glc)-isomer. alpha-D-glucose 1-phosphate : A D-glucopyranose 1-phosphate in which the anomeric centre has alpha-configuration.	2.1	1	0	D-glucopyranose 1-phosphate
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.	2.1	1	0	cephalosporin	fungal metabolite
peroxyformic acid peroxyformic acid: structure	7.97	4	0
bisphenol b [no description available]	2.11	1	0	bisphenol
boron nitride [no description available]	7.21	1	0	nitride
violuric acid violuric acid: an antihypoxic agent	2.96	4	0
2,3,5,6-tetrachlorohydroquinone [no description available]	2	1	0	chlorohydroquinones; tetrachlorobenzene
salicylhydroxamic acid [no description available]	3	4	0	hydroxamic acid; phenols	antibacterial drug; EC 1.11.2.2 (myeloperoxidase) inhibitor; EC 3.5.1.5 (urease) inhibitor; trypanocidal drug
1,7-phenanthroline [no description available]	2.05	1	0	phenanthroline
benzo-1,2,3-thiadiazole [no description available]	2.59	2	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.	4.45	21	0	1,2,3-triazole
hydracrylic acid 3-hydroxypropionic acid : A 3-hydroxy monocarboxylic acid that is propionic acid in which one of the hydrogens attached to the terminal carbon is replaced by a hydroxy group.	2.6	1	0	3-hydroxy monocarboxylic acid; omega-hydroxy-short-chain fatty acid	Escherichia coli metabolite; human metabolite
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.	2.59	2	0	anthocyanidin chloride
2,6-dimethoxy-1,4-benzoquinone 2,6-dimethoxy-1,4-benzoquinone: structure given in first source	2.05	1	0
azure b Azure B: RN given refers to chloride. azure B : An organic chloride salt having 3-(dimethylamino)-7-(methylamino)phenothiazin-5-ium as the counterion. It is used in making azure eosin stains for blood smear staining and is an active metabolite of methylene blue.	2.96	4	0
1,3,5-trimethoxybenzene 1,3,5-trimethoxybenzene : A methoxybenzene carrying methoxy groups at positions 1, 3 and 5. It has been found to be a biomarker of flavonoid consumption in humans.	7.05	1	0	methoxybenzenes	biomarker; human xenobiotic metabolite
methyl levulinate methyl levulinate: structure in first source	2.21	1	0	oxo carboxylic acid
5-fluoroorotic acid 5-fluoroorotic acid: inhibits the dietary induction of serine dehydratase. 5-fluoroorotic acid : A pyrimidinemonocarboxylic that is orotic acid which is substituted by fluorine at position 5. It is used in yeast molecular genetics to detect expression of the URA3 gene, which encodes orotine-5'-monophosphate dicarboxylase. A yeast with and active URA3 gene converts 5-fluoroorotic acid to fluorodeoxyuridine, which is toxic to cells.	2.41	2	0
methyl syringate methyl syringate : A benzoate ester obtained by the formal condensation of carboxy group of syringic acid with methanol.	2.76	3	0	benzoate ester; dimethoxybenzene; phenols	plant metabolite
2-chloroacrylonitrile 2-chloroacrylonitrile: structure given in first source	2.25	1	0
vanillylamine vanillylamine: inhibits microsomal enzyme function; RN given refers to parent cpd; structure	3.16	3	0	aralkylamino compound
9,10-dicyanoanthracene 9,10-dicyanoanthracene: structure in first source. anthracene-9,10-dinitrile : An anthracenedinitrile carrying cyano groups at positions 9 and 10.	2.06	1	0	acene-9,10-dinitrile; anthracenedinitrile
sesamin (+)-sesamin : A lignan that consists of tetrahydro-1H,3H-furo[3,4-c]furan substituted by 1,3-benzodioxole groups at positions 1 and 4 (the 1S,3aR,4S,6aR stereoisomer). Isolated from Cinnamomum camphora, it exhibits cytotoxic activity.	2.73	3	0	benzodioxoles; furofuran; lignan	antineoplastic agent; neuroprotective agent; plant metabolite
2-(4-aminophenyl)ethylamine 2-(4-aminophenyl)ethylamine: used to prepare derivatives of reducing oligosaccharides; structure given in first source	2.01	1	0
maslinic acid (2Alpha,3beta)-2,3-dihydroxyolean-12-en-28-oic acid: from Luehea divaricata and Agrimonia eupatoria	2.13	1	0	dihydroxy monocarboxylic acid; pentacyclic triterpenoid	anti-inflammatory agent; antineoplastic agent; antioxidant; 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.	3.15	5	0	benzamides; isoxazoles	cellulose synthesis inhibitor; herbicide
4-nitrophenyl palmitate p-nitrophenyl palmitate : A palmitate ester obtained by condensation of the carboxy group of palmitic acid with the phenolic hydroxy group of p-nitrophenol.	2.11	1	0	C-nitro compound; hexadecanoate ester
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.	2.83	3	0	cerium molecular entity; metal oxide
sodium oxide [no description available]	2.31	1	0
tetrabutylphosphonium tetrabutylphosphonium: RN given refers to Br	7.55	2	0
benzylvanillin benzylvanillin: structure given in first source	1.99	1	0
1-hydroxybenzotriazole 1-hydroxybenzotriazole: RN given refers to parent cpd	4.18	16	0	benzotriazoles
2,5-furandicarboxylic acid furan-2,5-dicarboxylic acid : A member of the class of furans carrying two carboxy substituents at positions 2 and 5.	3.62	2	0	dicarboxylic acid; furans	human urinary metabolite
1-pyrenebutyrate 1-pyrenebutyrate: fluorescent probe; RN given refers to 1-pyrenebutyrate	2.25	1	0
5-hydroxymethyl-2-furoic acid 5-hydroxymethyl-2-furoic acid: structure in first source. 5-hydroxymethyl-2-furoic acid : A member of the class of furoic acids that is 2-furoic acid substituted at position 5 by a hydroxymethyl group.	2.1	1	0	aromatic primary alcohol; furoic acid	bacterial xenobiotic metabolite; fungal metabolite; human urinary metabolite; nematicide
1,3,6,8-pyrene tetrasulfonate 1,3,6,8-pyrene tetrasulfonate: RN given refers to parent cpd	2.41	1	0
4-methylmorpholine n-oxide N-methylmorpholine N-oxide : A morpholine N-oxide resulting from the oxidation of the amino group of N-methylmorpholine.	3.2	5	0	morpholine N-oxide
lithium bromide lithium bromide: denatures ribonuclease A; also sedative. lithium bromide : A lithium salt in which the counterion is bromide. The anhydrous salt forms cubic crystals similar to common salt.	3.01	4	0	bromide salt; lithium salt
cryptolepine cryptolepine: fused indole-quinoline; structure in first source; from CRYPTOLEPIS sanguinolenta. cryptolepine : An organic heterotetracyclic compound that is 5H-indolo[3,2-b]quinoline in which the hydrogen at position N-5 is replaced by a methyl group.	2.03	1	0	indole alkaloid; organic heterotetracyclic compound; organonitrogen heterocyclic compound	anti-inflammatory agent; antimalarial; antineoplastic agent; cysteine protease inhibitor; plant metabolite
clarithromycin Clarithromycin: A semisynthetic macrolide antibiotic derived from ERYTHROMYCIN that is active against a variety of microorganisms. It can inhibit PROTEIN SYNTHESIS in BACTERIA by reversibly binding to the 50S ribosomal subunits. This inhibits the translocation of aminoacyl transfer-RNA and prevents peptide chain elongation.. clarithromycin : The 6-O-methyl ether of erythromycin A, clarithromycin is a macrolide antibiotic used in the treatment of respiratory-tract, skin and soft-tissue infections. It is also used to eradicate Helicobacter pylori in the treatment of peptic ulcer disease. It prevents bacteria from growing by interfering with their protein synthesis.	4.9	1	1	macrolide antibiotic	antibacterial drug; environmental contaminant; protein synthesis inhibitor; xenobiotic
difenoconazole difenoconazole : A member of the class of dioxolanes that is 1,3-dioxolane substituted at position 2 by 2-chloro-4-(4-chlorophenoxy)phenyl and 1,2,4-triazol-1-ylmethyl groups. A broad spectrum fungicide with novel broad-range activity used as a spray or seed treatment. It is moderately toxic to humans, mammals, birds and most aquatic organisms.	2.6	1	0	aromatic ether; conazole fungicide; cyclic ketal; dioxolane; triazole fungicide; triazoles	antifungal agrochemical; EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor; environmental contaminant; xenobiotic
cyprodinil cyprodinil: structure in first source. cyprodinil : A member of the class of aminopyrimidine that is N-phenylpyrimidin-2-amine carrying additional cyclopropyl and methyl substituents at positions 4 and 6 respectively. A broad spectrum fungicide used to control a range of pathogens including Tapesia yallundae, Botrytis spp., Alternaria spp. and Rhynchospium secalis. Whilst it is a recognised irritant no serious human health concerns have been identified. It is moderately toxic to birds as well as most aquatic organisms and earthworms, but it is not considered toxic to honeybees.	2.02	1	0	aminopyrimidine; anilinopyrimidine fungicide; cyclopropanes; secondary amino compound	antifungal agrochemical; aryl hydrocarbon receptor agonist; environmental contaminant; xenobiotic
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.	2.41	1	0	benzothiadiazole; thioester	antifungal agrochemical; plant activator; profungicide
coenzyme a [no description available]	3.31	6	0	adenosine 3',5'-bisphosphate	coenzyme; Escherichia coli metabolite; mouse metabolite
2,6-dichloro-4-hydroquinone 2,6-dichloro-4-hydroquinone: structure in first source. 2,6-dichlorohydroquinone : A dichlorohydroquinone that is hydroquinone substituted by chloro groups at positions 2 and 6.	2	1	0	dichlorohydroquinone
o-desmethylangolensin O-desmethylangolensin: structure given in first source	1.97	1	0	stilbenoid
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.	8.64	9	0	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
equol Equol: A non-steroidal ESTROGEN generated when soybean products are metabolized by certain bacteria in the intestines.	1.97	1	0	hydroxyisoflavans
friedelin 3-friedelanone: from the stem bark of Irvingia gabonensis; structure in first source. friedelin : A pentacyclic triterpenoid that is perhydropicene which is substituted by an oxo group at position 3 and by methyl groups at the 4, 4a, 6b, 8a, 11, 11, 12b, and 14a-positions (the 4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS-enantiomer). It is the major triterpenoid constituent of cork.	2.03	1	0	cyclic terpene ketone; pentacyclic triterpenoid	anti-inflammatory drug; antipyretic; non-narcotic analgesic; plant metabolite
cadmium telluride cadmium telluride: used in radiation monitoring device	2.41	1	0
goethite [no description available]	7.9	2	0
alpha-peltatin alpha-peltatin: RN given for (5R-(5alpha,5beta,8aalpha))-isomer. alpha-peltatin : An organic heterotetracyclic compound that is 4'-demethylpodophyllotoxin which is substituted by a hydroxy group at position 10 but which is lacking the hydroxy group at position 9. It is found as a glucoside in the rhizomes of Podophyllum peltatum.	1.97	1	0	furonaphthodioxole; gamma-lactone; lignan; organic heterotetracyclic compound; phenols	antineoplastic agent; metabolite
succinyl-coenzyme a [no description available]	2.13	1	0	omega-carboxyacyl-CoA	Escherichia coli metabolite; inhibitor; mouse metabolite
chalcone epoxide chalcone epoxide: activator of epoxide hydrolase; RN given refers to cpd without isomeric designation; structure given in first source	7.03	1	0
1-hydroxy-1-phenyl-2-propanone 1-hydroxy-1-phenylpropan-2-one : A secondary alpha-hydroxy ketone that is benzene which is substituted by a 1-hydroxy-2-oxopropyl group at position 1.	4.23	1	0	benzenes; methyl ketone; secondary alpha-hydroxy ketone
5-methyltryptophan 5-methyltryptophan: RN given refers to cpd without isomeric designation. 5-methyltryptophan : A tryptophan derivative that is tryptophan substituted by a methyl group at position 5 of the indole ring.	2.07	1	0	non-proteinogenic alpha-amino acid; tryptophan derivative
titanium nitride (tin) titanium nitride: RN given refers to unspecified MF	2.1	1	0
arabitol arabitol: RN given refers to cpd without isomeric designation. arabinitol : A pentitol that is the sugar alcohol produced by the reduction of arabinose or lyxose. It is found in serum or urine of human infected with Candida albicans.. D-arabinitol : The D-enantiomer of arabinitol.	2.17	1	0	arabinitol
pyrimidine dimers Pyrimidine Dimers: Dimers found in DNA chains damaged by ULTRAVIOLET RAYS. They consist of two adjacent PYRIMIDINE NUCLEOTIDES, usually THYMINE nucleotides, in which the pyrimidine residues are covalently joined by a cyclobutane ring. These dimers block DNA REPLICATION.	2.41	1	0
dehydroabietic acid dehydroabietic acid: major aquatic toxicant in effluent of pulp and paper mills. dehydroabietic acid : An abietane diterpenoid that is abieta-8,11,13-triene substituted at position 18 by a carboxy group.. dehydroabietate : A monocarboxylic acid anion that is the conjugate base of dehydroabietic acid, obtained by deprotonation of the carboxy group.	2.49	2	0	abietane diterpenoid; carbotricyclic compound; monocarboxylic acid	allergen; metabolite
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.	10.71	23	0	D-glucuronic acid	algal metabolite
dehydrodivanillin dehydrodivanillin: a lignin-related compound	2.69	3	0
2-hydroxy-1,2-bis(methoxyphenyl)ethanone 2-hydroxy-1,2-bis(methoxyphenyl)ethanone: structure given in first source	1.99	1	0
diosgenin [no description available]	2.51	2	0	3beta-sterol; hexacyclic triterpenoid; sapogenin; spiroketal	antineoplastic agent; antiviral agent; apoptosis inducer; metabolite
syringaresinol [no description available]	2.13	1	0	aromatic ether; furofuran; lignan; polyether; polyphenol	plant metabolite
coumarin 6 coumarin 6: structure in first source	2.1	1	0	7-aminocoumarins	fluorochrome
arctiin arctiin: from fruits of Arctium lappa L; RN given refers to (3R-trans)-isomer; RN for cpd without isomeric designation not avail 12/92	2.38	2	0	glycoside; lignan
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.	10.2	14	0	cobalt group element atom; metal allergen	micronutrient
hydrogen sulfite [no description available]	3.36	6	0	sulfur oxoanion	human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
arginyl-glycyl-aspartic acid arginyl-glycyl-aspartic acid: amino acid sequence of basic unit of widespread cellular recognition system	2.03	1	0	oligopeptide
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).	4.89	10	0
beta-hydroxyvaleric acid 3-hydroxypentanoic acid : A short-chain fatty acid that is valeric acid in which one of the methylene hydrogens at position 3 has been replaced by a hydroxy group.	2.91	3	0	3-hydroxy fatty acid; ketone body; short-chain fatty acid
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.	10.89	17	0	proanthocyanidin
epicatechin gallate epicatechin gallate: a steroid 5alpha-reductase inhibitor; RN given refers to the (cis)-isomer; structure given in first source; isolated from green tea. (-)-epicatechin-3-O-gallate : A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin. A natural product found in Parapiptadenia rigida.	2.01	1	0	catechin; gallate ester; polyphenol	EC 3.2.1.1 (alpha-amylase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; metabolite
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.	2.17	1	0	phosphite ion; trivalent inorganic anion
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.	4.95	6	0
schizandrin b schizandrin B: a phytogenic antineoplastic agent with anti-inflammatory activity; isolated from Schisandra plant	1.97	1	0
1-hexadecyl-2-acetyl-glycero-3-phosphocholine Platelet Activating Factor: A phospholipid derivative formed by PLATELETS; BASOPHILS; NEUTROPHILS; MONOCYTES; and MACROPHAGES. It is a potent platelet aggregating agent and inducer of systemic anaphylactic symptoms, including HYPOTENSION; THROMBOCYTOPENIA; NEUTROPENIA; and BRONCHOCONSTRICTION.. 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine : A 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine betaine which has hexadecyl as the alkyl group. PAF is a potent phospholipid activator and mediator of many leukocyte functions, including platelet aggregation, inflammation, and anaphylaxis.	5.17	6	0	2-acetyl-1-alkyl-sn-glycero-3-phosphocholine	antihypertensive agent; beta-adrenergic antagonist; bronchoconstrictor agent; hematologic agent; vasodilator agent
bifendate 7,7'-dimethoxy-(4,4'-bi-1,3-benzodioxole)-5,5'-dicarboxylic acid dimethyl ester: structure given in first source	3.07	1	0
deoxyglucose Deoxyglucose: 2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.. deoxyglucose : A deoxyhexose comprising glucose having at least one hydroxy group replaced by hydrogen.	2.49	2	0
4-methoxymandelic acid 4-methoxymandelic acid: RN given refers to parent cpd; structure given in first source	1.97	1	0
2,3-bis(3'-hydroxybenzyl)butyrolactone 2,3-bis(3'-hydroxybenzyl)butyrolactone: lignan isolated from urine of humans & other mammals; RN given refers to cpd without isomeric designation; structure given in second source	4.29	7	0	lignan
dodecyl-beta-d-maltoside dodecyl beta-D-maltoside : A glycoside resulting from attachment of a dodecyl group to the reducing-end anomeric centre of a beta-maltose molecule.	1.99	1	0	disaccharide derivative; glycoside	detergent
tanshinone tanshinone: from root of Salvia miltiorrhiza Bunge; RN given refers to tanshinone I; cardioprotective agent and neuroprotective agent	2.11	1	0	abietane diterpenoid	anticoronaviral agent
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	7.88	3	0	22-hydroxy steroid; 23-hydroxy steroid; 2alpha-hydroxy steroid; 3alpha-hydroxy steroid; brassinosteroid	plant growth stimulator; plant hormone
estrone-3-glucuronide [no description available]	1.96	1	0	17-oxo steroid; beta-D-glucosiduronic acid; steroid glucosiduronic acid	human metabolite; mouse metabolite
matairesinol matairesinol: lignan that is a central precursor in plants in the biosynthesis of numerous lignans (coordinate with specific); RN refers to (3R-trans)-isomer. (-)-matairesinol : A lignan that is gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer).	2.92	4	0	gamma-lactone; lignan; polyphenol	angiogenesis inhibitor; anti-asthmatic agent; phytoestrogen; plant metabolite
caprylates Caprylates: Derivatives of caprylic acid. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain a carboxy terminated eight carbon aliphatic structure.. octanoate : A straight-chain saturated fatty acid anion that is the conjugate base of octanoic acid (caprylic acid); believed to block adipogenesis.	2.49	2	0	fatty acid anion 8:0; straight-chain saturated fatty acid anion	human metabolite; Saccharomyces cerevisiae metabolite
tris(2-carboxyethyl)phosphine tris(2-carboxyethyl)phosphine: water-soluble reagent which irreversibly reduces disulfides to thiols at room temperature & is active below neutral pH; used for quantitation of iodine and iodate. TCEP : A tertiary phosphine in which phosphane is substituted with three 2-carboxyethyl groups. It is a commonly used reducing agent.	2.41	1	0	phosphine derivative; tricarboxylic acid	reducing agent
kadsurenone kadsurenone: platelet-activating factor receptor antagonist from Chinese herbal plant, haifenteng; structure given in first source; RN given refers to (2s-(2alpha,3beta,3aalpha))-isomer	3.48	2	0	benzofurans
benzoyl-coenzyme a benzoyl-coenzyme A: RN given refers to unlabeled cpd	3.08	1	0
chaetoglobosins chaetoglobosins: like CYTOCHALASINS but with an indoyl in place of a phenyl ring at C10; chaetoglobosins A-J; metabolites of Chaetomium species; RN given refers to chaetoglobosin A; structure. chaetoglobosin A : A cytochalasan alkaloid isolated from Chaetomium globosum and Calonectria morganii.	2.25	1	0
phenoxy radical phenoxy radical : An organic radical generated from phenol.	5.18	8	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).	2.5	2	0	carbene; methanediyl
perchlorate perchlorate: the explosive component of rocket fuel; an environmental contaminant that disrupts THYROID HORMONES. perchlorate : A monovalent inorganic anion obtained by deprotonation of perchloric acid.	2.13	1	0	chlorine oxoanion; monovalent inorganic anion
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.	2.86	3	0	fullerene	geroprotector
2,3-bis(3'-hydroxybenzyl)butane-1,4-diol 2,3-bis(3'-hydroxybenzyl)butane-1,4-diol: lignan isolated from urine of humans & other mammals	4.01	5	0	lignan
n(6)-carboxymethyllysine N(6)-carboxymethyllysine: RN given refers to (L)-isomer; structure given in first source. N(6)-carboxymethyl-L-lysine : An L-lysine derivative with a carboxymethyl substituent at the N(6)-position.	3.51	1	1	L-lysine derivative; non-proteinogenic L-alpha-amino acid	antigen
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
2,3-dibenzylbutane-1,4-diol 2,3-dibenzylbutane-1,4-diol: RN given refers to parent cpd	1.97	1	0
4-methoxy-1,2-benzoquinone 4-methoxy-1,2-benzoquinone: structure given in first source	1.98	1	0
ectoine [no description available]	2.08	1	0	1,4,5,6-tetrahydropyrimidines; carboxamidine; monocarboxylic acid; zwitterion	osmolyte
methotrexate [no description available]	2.6	1	0	dicarboxylic acid; monocarboxylic acid amide; pteridines	abortifacient; antimetabolite; antineoplastic agent; antirheumatic drug; dermatologic drug; DNA synthesis inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; immunosuppressive agent
planinin planinin: from Zanthoxylum planispinum; structure given in first source	2.1	1	0	lignan
carbapenems [no description available]	4.9	1	1
xylose xylopyranose: structure in first source	11.29	372	0	D-xylose
quinone methide quinone methide: intermediate in eumelanin biosynthesis; structure given in first source. quinomethane : A methylidenecyclohexadienone, formally derived from a benzoquinone by replacement of one of the quinone oxygens by a methylidene group.	4.53	7	0	quinomethane
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.	2.41	1	0	beta-lactam antibiotic allergen; beta-lactam
cyclohexadienone cyclohexadienone: structure in first source	7.41	1	0
proline Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.	8.44	6	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
cucurbitaceae Cucurbitaceae: The gourd plant family of the order Violales, subclass Dilleniidae, class Magnoliopsida. It is sometimes placed in its own order, Cucurbitales. 'Melon' generally refers to CUCUMIS; CITRULLUS; or MOMORDICA.	2.8	3	0
bis(trifluoroethyl)carbamodithioic acid [no description available]	2.41	1	0
4-o-methylglucuronic acid 4-O-methylglucuronic acid: RN given refers to cpd without isomeric designation	2.74	3	0
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.	3.21	5	0	cycloalkene; cyclopropenes	agrochemical; plant growth regulator
threonic acid threonic acid: RN given refers to (R,S)-isomer	2.07	1	0	threonic acid
borneo Borneo: An island in the Malay Archipelago, east of Sumatra, north of Java, and west of Celebes. It is the third largest island in the world. Its name is a Portuguese alteration of BRUNEI, located on it. (From Webster's New Geographical Dictionary, 1988, p163; Room, Brewer's Dictionary of Names, 1992, p73)	2.72	3	0	organofluorine acaricide
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.	4.9	1	1	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
nectandrin-b nectandrin-B: antifungal lignan from the seeds of Myristica fragrans; structure in first source	2.07	1	0
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	4.73	28	0	oxygen hydride; oxygen radical; reactive oxygen species
resiquimod S 28463: structure given in first source	7.31	1	0	imidazoquinoline
sodium percarbonate sodium percarbonate: RN given refers to unspecified Na salt	7.9	3	0
singlet oxygen Singlet Oxygen: An excited state of molecular oxygen generated photochemically or chemically. Singlet oxygen reacts with a variety of biological molecules such as NUCLEIC ACIDS; PROTEINS; and LIPIDS; causing oxidative damages.	2.92	4	0	chalcogen; monoatomic oxygen; nonmetal atom	macronutrient
fenton's reagent Fenton's reagent: used for oxidizing sugars & alcohols	4.31	18	0
isolariciresinol isolariciresinol: RN given refers to ((1-S-(1alpha,2beta,3alpha))-isomer); structure given in first source. (+)-isolariciresinol : A lignan that is 5,6,7,8-tetrahydronaphthalen-2-ol substituted by hydroxymethyl groups at positions 6 and 7, a methoxy group at position 3 and a 4-hydroxy-3-methoxyphenyl group at position 8. It has been isolated from the roots of Rubia yunnanensis.	4.56	24	0	guaiacols; lignan; polyphenol; primary alcohol	plant metabolite
dimethylsulfonioacetate dimethylthetin: synthetic analog of glycine betaine; structure in first source	2.6	1	0	sulfonium betaine
isoflavanone isoflavanone: structure given in first source; RN from CA Index Guide. isoflavanone : Isoflavone in which the double bond between positions 2 and 3 has been reduced to a single bond.	2.05	1	0	isoflavanones
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	2.11	1	0
platycodin d platycodin D: triterpenoid saponin from a root of Platycodon grandiflorum; RN refers to (2beta,3beta,16alpha)-isomer; structure given in first source	2.6	1	0	triterpenoid saponin	metabolite
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.	7.11	1	0	labdane diterpenoid	antifungal agent; antimicrobial agent; apoptosis inducer; fragrance; plant metabolite
metaperiodate metaperiodate: RN given refers to periodic acid, Na salt; structure. periodate : A monovalent inorganic anion obtained by deprotonation of periodic acid.	2.37	2	0	iodine oxoanion; monovalent inorganic anion
isophorone diisocyanate [no description available]	2.25	1	0	diisocyanate
magnolin magnolin: from flower buds of Magnolia biondii	3.12	5	0
tracheloside tracheloside: a lignan isolated from the seeds of Arctium lappa and Carthamus tinctorius; structure given in first source	2.38	2	0	glycoside; lignan	metabolite
alpha-aminooxy-beta-phenylpropionic acid alpha-aminooxy-beta-phenylpropionic acid: inhibits phenylalanine ammonia-lyase; RN given refers to (S)-isomer	7.68	3	0
terics terics: medicated blocks used for control of cattle bloat; RN given is for teric N; nonylphenol ethoxylate is resistant to environmental breakdown so EPA discourages use	2.05	1	0
n,n'-bis(salicylideneamino)ethane-manganese(ii) N,N'-bis(salicylideneamino)ethane-manganese(II): structure given in first source	2	1	0
biotin vitamin B7 : Any member of a group of vitamers that belong to the chemical structural class called biotins that exhibit biological activity against vitamin B7 deficiency. Vitamin B7 deficiency is very rare in individuals who take a normal balanced diet. Foods rich in biotin are egg yolk, liver, cereals, vegetables (spinach, mushrooms) and rice. Symptoms associated with vitamin B7 deficiency include thinning hair, scaly skin rashes around eyes, nose and mouth, and brittle nails. The vitamers include biotin and its ionized and salt forms.	2.89	3	0	biotins; vitamin B7	coenzyme; cofactor; Escherichia coli metabolite; fundamental metabolite; human metabolite; mouse metabolite; nutraceutical; prosthetic group; Saccharomyces cerevisiae metabolite
1-methyl-3-ethylimidazolium 1-methyl-3-ethylimidazolium: structure given in first source. 1-ethyl-3-methylimidazolium : A 1-alkyl-3-methylimidazolium in which the alkyl substituent at C-1 is ethyl.	5.09	39	0	1-alkyl-3-methylimidazolium
atropine tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate : A tropane alkaloid that is (1R,5)-8-methyl-8-azabicyclo[3.2.1]octane substituted by a (3-hydroxy-2-phenylpropanoyl)oxy group at position 3.	2.05	1	0
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	2.71	3	0	divalent inorganic anion; phosphite ion
nickel monoxide [no description available]	2.05	1	0
thaxtomine a thaxtomine A: a phytotoxin produced by Streptomyces scabies; RN given for (3R-trans)-isomer; structure in first source	2.05	1	0
psyllium Psyllium: Dried, ripe seeds of PLANTAGO PSYLLIUM; PLANTAGO INDICA; and PLANTAGO OVATA. Plantain seeds swell in water and are used as demulcents and bulk laxatives.	7.87	4	0	very long-chain fatty acid
3,4-divanillyltetrahydrofuran 3,4-divanillyltetrahydrofuran: lignan with the highest binding affinity; structure in first source	3.01	4	0
aflatoxin b1 Aflatoxin B1: A potent hepatotoxic and hepatocarcinogenic mycotoxin produced by the Aspergillus flavus group of fungi. It is also mutagenic, teratogenic, and causes immunosuppression in animals. It is found as a contaminant in peanuts, cottonseed meal, corn, and other grains. The mycotoxin requires epoxidation to aflatoxin B1 2,3-oxide for activation. Microsomal monooxygenases biotransform the toxin to the less toxic metabolites aflatoxin M1 and Q1.. aflatoxin B1 : An aflatoxin having a tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4 and 11.	7.72	2	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
137 l [no description available]	2.6	1	0
n-acetylchitooctaose N-acetylchitooctaose: induces phytoalexin production in rice cells	2.01	1	0
veratrylglycerol-beta-guaiacyl ether veratrylglycerol-beta-guaiacyl ether: structure given in first source. veratrylglycerol beta-guaiacyl ether : A idol that is propane-1,3-diol substituted by a 3,4-dimethoxyphenyl group at position 1 and a 2-methoxyphenoxy group at position 2 respectively.	2.67	3	0	dimethoxybenzene; diol
vanadium disulfide [no description available]	2.25	1	0
chlorite [no description available]	3.96	12	0	chlorine oxoanion; monovalent inorganic anion
prizes acetamiprid: structure in first source. (E)-acetamiprid : The (E)-stereoisomer of acetamiprid.. acetamiprid : A carboxamidine that is acetamidine in which the amino hydrogens are substituted by a (6-chloropyridin-3-yl)methyl and a methyl group while the hydrogen attached to the imino nitrogen is replaced by a cyano group.	2.25	1	0	carboxamidine; monochloropyridine; nitrile	environmental contaminant; neonicotinoid insectide; xenobiotic
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.	8.97	4	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	3.35	1	0
cellulose triacetate cellulose triacetate: for hemodialysis filtration	2.03	1	0
eudesmin eudesmin: RN refers to (1R-(1alpha,3aalpha,4alpha,6aalpha))-isomer; structure given in first source; very similar to pinoresinol	2.01	1	0
5-hydroxymethylfurfural 5-hydroxymethylfurfural: has antisickling activity; HMF is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo. 5-hydroxymethylfurfural : A member of the class of furans that is furan which is substituted at positions 2 and 5 by formyl and hydroxymethyl substituents, respectively. Virtually absent from fresh foods, it is naturally generated in sugar-containing foods during storage, and especially by drying or cooking. It is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo.	9.11	96	0	arenecarbaldehyde; furans; primary alcohol	indicator; Maillard reaction product
sodium sulfide sodium sulfide: see also record for sodium bisulfide; actisoufre is the sodium sulfide component of sulfur-containing thermal springs which is also found in Saccharomyces cerevisiae	3	4	0
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	4.98	12	0
lupeol [no description available]	2.01	1	0	pentacyclic triterpenoid; secondary alcohol	anti-inflammatory drug; plant metabolite
calendula Calendula: A plant genus of the family ASTERACEAE. Members contain CAROTENOIDS, essential oils (OILS, VOLATILE), flavonoids, mucilage, SAPONINS, and STEROLS. The plants are used both topically and internally. The common name of Marigold is also used for TAGETES.	2.05	1	0
2-(4-aminophenyl)quinoline 2-(4-aminophenyl)quinoline: used for imaging tau protein; structure in first source	2.25	1	0
lariciresinol lariciresinol: found in human urine. (+)-lariciresinol : A lignan that is tetrahydrofuran substituted at positions 2, 3 and 4 by 4-hydroxy-3-methoxyphenyl, hydroxymethyl and 4-hydroxy-3-methoxybenzyl groups respectively (the 2S,3R,4R-diastereomer).	4.04	14	0	aromatic ether; lignan; oxolanes; phenols; primary alcohol	antifungal agent; plant metabolite
medicarpin (-)-medicarpin : The (-)-enantiomer of medicarpin.	2.17	1	0	medicarpin	plant metabolite
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	2.61	2	0
permanganate [no description available]	2.68	3	0	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.	2.04	1	0
carboplatin [no description available]	2.15	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.	3.49	7	0	inorganic chloride; lithium salt	antimanic drug; geroprotector
schisanhenol schisanhenol: a dibenzyl cyclooctane from kernels of Schisandra rubriflora; structure given in first source	2.38	2	0
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.	7.46	2	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
sorbose sorbopyranose : The pyranose form of sorbose.. L-sorbopyranose : The L-stereoisomer of sorbopyranose.	1.94	1	0	L-sorbose; sorbopyranose
arabinose [no description available]	7.23	49	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.	1.95	1	0	peptide
amylopectin Amylopectin: A highly branched glucan in starch.. amylopectin : A polydisperse highly branched polysaccharide derivative composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage. The chains are joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some 6-phosphate ester groups also may occur. The branches in amylopectin typically contain 24 to 30 glucose residues.	2.38	2	0
hexacyanoferrate iii hexacyanoferrate III: RN given refers to parent cpd	2.43	2	0
glucosamine D-glucosamine : An amino sugar whose structure comprises D-glucose having an amino substituent at position 2.. 2-amino-2-deoxy-D-glucopyranose : A D-glucosamine whose structure comprises D-glucopyranose having an amino substituent at position 2.	8.3	6	0	D-glucosamine	Escherichia coli metabolite; geroprotector; mouse metabolite
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.	2.76	3	0	D-galacturonic acid
glucosamine 6-phosphate glucosamine 6-phosphate: RN given refers to parent cpd	2.07	1	0	2-amino-2-deoxy-D-glucopyranose 6-phosphate	human metabolite; Saccharomyces cerevisiae metabolite
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.	2.21	1	0	3,5-dihydroxy-3-methylpentanoic acid
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	2	1	0	(2S)-flavan-4-one; naringenin	expectorant; plant metabolite
epiglucan epiglucan: a highly side-chain/branched alkali-insoluble cell wall glucan from fungus such as Epicoccum nigrum, Botrytis cinerea, ascomycetes & basidiomycetes; also isolated S-4001 from Lei Wan (polyporus mylitiae), HA-beta-glucan from mushroom Pleutotus ostreatus (Fr.) Quel., and translam from seaweed Laminaria cichorioides; with commercially important functional properties including emulsification and friction reduction.	4.25	16	0
laminaran beta-1,3-glucan: component of fungal cell walls; also used as antitumor polysaccharide; unspecified D usually means BETA-GLUCANS; beta-1,3-D-glucan is also available; glucan phosphate is also available; biosynthesis is inhibited by echinocandins (cyclic hexapeptides). laminarin : A polysaccharide composed of beta-(1->3)-linked glucose residues containing sporadic beta-(1->6)-linkages as branch points or inter-residue linkages and 2-3% D-mannitol at some reducing termini.	2.53	2	0
inositol 1,4,5-trisphosphate Inositol 1,4,5-Trisphosphate: Intracellular messenger formed by the action of phospholipase C on phosphatidylinositol 4,5-bisphosphate, which is one of the phospholipids that make up the cell membrane. Inositol 1,4,5-trisphosphate is released into the cytoplasm where it releases calcium ions from internal stores within the cell's endoplasmic reticulum. These calcium ions stimulate the activity of B kinase or calmodulin.	2	1	0	myo-inositol trisphosphate	mouse metabolite
cysteinylglycine cysteinylglycine: RN given refers to (L)-isomer; RN for cpd without isomeric designation not in Chemlne 7/13/83. L-cysteinylglycine : A dipeptide consisting of glycine having an L-cysteinyl attached to its alpha-amino group. It is an intermediate metabolite in glutathione metabolism.	2.08	1	0	dipeptide zwitterion; dipeptide	Escherichia coli metabolite; human metabolite; Saccharomyces cerevisiae metabolite
salicin [no description available]	2.42	2	0	aromatic primary alcohol; aryl beta-D-glucoside; benzyl alcohols	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug
casein hydrolysate casein hydrolysate: an ingredient of trypticase soy broth; casitone is a tryptic digest of casein	2.02	1	0
taxifolin (+)-taxifolin : A taxifolin that has (2R,3R)-configuration.	2.79	3	0	taxifolin	metabolite
xylobiose xylobiose: RN given refers to D-xylose. xylobiose : A glycosylxylose that is D-xylopyranose having a beta-D-xylopyranosyl residue attached at position 4 via a glycosidic bond.	3.17	5	0	glycosylxylose	bacterial metabolite
cellotetraose cellotetraose: RN given refers to (beta-D)-isomer. cellotetraose : A glucotetrose comprised of four D-glucose residues connected by beta(1->4) linkages.	3.03	4	0	glucotetraose
tartaric acid tartaric acid: RN given refers to cpd with unspecified isomeric designation. D-tartaric acid : The D-enantiomer of tartaric acid.	2.98	4	0	tartaric acid	Escherichia coli metabolite
inositol 3-phosphate inositol 3-phosphate: RN given refers to (myo)-isomer	2.02	1	0
fructans (2->6)-beta-D-fructan : A fructan compound consisting of repeating (2->6)-beta-linked fructofuranose units.	2.01	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.	12.68	818	0	cellotriose
meropenem Meropenem: A thienamycin derivative antibacterial agent that is more stable to renal dehydropeptidase I than IMIPENEM, but does not need to be given with an enzyme inhibitor such as CILASTATIN. It is used in the treatment of bacterial infections, including infections in immunocompromised patients.. meropenem : A carbapenemcarboxylic acid in which the azetidine and pyrroline rings carry 1-hydroxymethyl and in which the azetidine and pyrroline rings carry 1-hydroxymethyl and 5-(dimethylcarbamoyl)pyrrolidin-3-ylthio substituents respectively.	4.9	1	1	alpha,beta-unsaturated monocarboxylic acid; carbapenemcarboxylic acid; organic sulfide; pyrrolidinecarboxamide	antibacterial agent; antibacterial drug; drug allergen
griseofulvin Griseofulvin: An antifungal agent used in the treatment of TINEA infections.. griseofulvin : An oxaspiro compound produced by Penicillium griseofulvum. It is used by mouth as an antifungal drug for infections involving the scalp, hair, nails and skin that do not respond to topical treatment.	1.94	1	0	1-benzofurans; antibiotic antifungal drug; benzofuran antifungal drug; organochlorine compound; oxaspiro compound	antibacterial agent; Penicillium metabolite
7-aminocephalosporanic acid 7beta-aminocephalosporanic acid : The alpha,beta-unsaturated monocarboxylic acid that is the active nucleus for the synthesis of cephalosporins and intermediates.	2.1	1	0	alpha,beta-unsaturated monocarboxylic acid; amino acid zwitterion
silychristin silychristin : A flavonolignan isolated from Silybum marianum and has been shown to exhibit inhibitory activities against lipoxygenase and prostaglandin synthetase.	2.13	1	0	1-benzofurans; aromatic ether; flavonolignan; polyphenol; secondary alpha-hydroxy ketone	lipoxygenase inhibitor; metabolite; prostaglandin antagonist; radical scavenger
tremulacin tremulacin: extracted from Folia Populus tomentosa Carr; structure given in first source	2.01	1	0	glycoside
lignans Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	11.49	128	0
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.	2.38	2	0	tripeptide
validamycin a validamycin A : A member of the class of validamycins that is (1R,2S,3S,4S,6R)-4-amino-6-(hydroxymethyl)cyclohexane-1,2,3-triol in which the hydroxy group at position 1 has been converted to its beta-D-glucoside and in which one of the hydrogens attached to the nitrogen is replaced by a (1R,4R,5R,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl group. It is the major validamycin produced by Streptomyces hygroscopicus.	2.06	1	0	antibiotic fungicide; polyol; secondary amino compound; validamycins	antifungal agrochemical; EC 2.4.1.231 [alpha,alpha-trehalose phosphorylase (configuration-retaining)] inhibitor; EC 2.4.1.64 (alpha,alpha-trehalose phosphorylase) inhibitor; EC 3.2.1.28 (alpha,alpha-trehalase) inhibitor
sultamicillin sultamicillin: contains ampicillin & sulbactam	4.9	1	1	penicillanic acid ester
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2.72	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.	3.76	9	0	butenedioic acid	algal metabolite; mouse metabolite; plant metabolite
acetyl coenzyme a Acetyl Coenzyme A: Acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.	2.91	3	0	acyl-CoA	acyl donor; coenzyme; effector; fundamental 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	5.45	19	0	cinnamic acid	plant metabolite
ergosterol [no description available]	3.67	9	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; ergostanoid; phytosterols	fungal metabolite; Saccharomyces cerevisiae metabolite
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.	4.47	6	0	butenedioic acid	food acidity regulator; fundamental metabolite; geroprotector
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	10.68	4	1	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).	4.27	4	1	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.	3.21	5	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.	9.96	120	1	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.	12.48	152	4	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.	3.29	5	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
5-hydroxyferulic acid 5-hydroxyferulic acid : Ferulic acid in which the ring hydrogen at position 5 is substituted by a hydroxy group.. (E)-5-hydroxyferulic acid : The E-isomer of 5-hydroxyferulic acid.	4.9	11	0	5-hydroxyferulic acid
phenylalaninol phenylalaninol: inhibits intestinal absorption of phenylalanine; RN given refers to cpd with unspecified stereochemistry. L-phenylalaninol : An amino alcohol resulting from the formal reduction of the carboxy group of L-phenylalanine to the corresponding alcohol.	2.15	1	0	amino alcohol; amphetamines; primary alcohol; primary amino compound
zeatin Zeatin: An aminopurine factor in plant extracts that induces cell division. (Grant & Hackh's Chemical Dict, 5th ed)	2.17	1	0	zeatin	plant metabolite
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).	1.98	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)	2.36	2	0	actinomycin	mutagen
conidendrin conidendrin: RN given for (3aR-(3aalpha,4alpha,9alpha,9abeta))-isomer; a phenyl-naphthyl-furanolactone	2.85	4	0	lignan	metabolite
gamma-sitosterol clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.	3	4	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols	marine metabolite; plant metabolite
melphalan Melphalan: An alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer - MELPHALAN, the racemic mixture - MERPHALAN, and the dextro isomer - MEDPHALAN; toxic to bone marrow, but little vesicant action; potential carcinogen.. melphalan : A phenylalanine derivative comprising L-phenylalanine having [bis(2-chloroethyl)amino group at the 4-position on the phenyl ring.	4.9	1	1	L-phenylalanine derivative; nitrogen mustard; non-proteinogenic L-alpha-amino acid; organochlorine compound	alkylating agent; antineoplastic agent; carcinogenic agent; drug allergen; immunosuppressive agent
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.	2.04	1	0	amino aldehyde; carbamate ester; tripeptide	proteasome inhibitor
schizandrin schizandrin: a dibenzocyclooctadiene lignan; schizandra is the plant name	3.07	1	0
l 743,872 [no description available]	2.11	1	0
riboflavin vitamin B2 : Any member of a group of vitamers that belong to the chemical structural class called flavins that exhibit biological activity against vitamin B2 deficiency. Symptoms associated with vitamin B2 deficiency include glossitis, seborrhea, angular stomaitis, cheilosis and photophobia. The vitamers include riboflavin and its phosphate derivatives (and includes their salt, ionised and hydrate forms).	3.14	5	0	flavin; vitamin B2	anti-inflammatory agent; antioxidant; cofactor; Escherichia coli metabolite; food colouring; fundamental metabolite; human urinary metabolite; mouse metabolite; photosensitizing agent; plant metabolite
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)	3.1	5	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.	2.57	2	0	one-carbon compound; organic sodium salt	antacid; food anticaking agent
sodium acetate, anhydrous Sodium Acetate: The trihydrate sodium salt of acetic acid, which is used as a source of sodium ions in solutions for dialysis and as a systemic and urinary alkalizer, diuretic, and expectorant.	2.41	1	0	organic sodium salt	NMR chemical shift reference compound
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.	2.05	1	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
ammonium carbonate ammonium carbonate: see also record for ammonium bicarbonate (mono-NH4 salt)	2.47	2	0
ammonium acetate ammonium acetate : An ammonium salt obtained by reaction of ammonia with acetic acid. A deliquescent white crystalline solid, it has a relatively low melting point (114degreeC) for a salt. Used as a food acidity regulator, although no longer approved for this purpose in the EU.	2.13	1	0	acetate salt; ammonium salt	buffer; food acidity regulator
bromochloroacetic acid Keratins: A class of fibrous proteins or scleroproteins that represents the principal constituent of EPIDERMIS; HAIR; NAILS; horny tissues, and the organic matrix of tooth ENAMEL. Two major conformational groups have been characterized, alpha-keratin, whose peptide backbone forms a coiled-coil alpha helical structure consisting of TYPE I KERATIN and a TYPE II KERATIN, and beta-keratin, whose backbone forms a zigzag or pleated sheet structure. alpha-Keratins have been classified into at least 20 subtypes. In addition multiple isoforms of subtypes have been found which may be due to GENE DUPLICATION.. bromochloroacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by bromine while a second is replaced by chlorine. A low-melting (27.5-31.5degreeC), hygroscopic crystalline solid, it can be formed during the disinfection (by chlorination) of water that contains bromide ions and organic matter, so can occur in drinking water as a byproduct of the disinfection process.	4.81	5	0	2-bromocarboxylic acid; monocarboxylic acid; organochlorine compound
xantphos xantphos: structure in first source	7.07	1	0
alpha-asarone asarone: structure in Merck Index, 9th ed, #847. asarone : A phenylpropanoid that is benzene substituted by methoxy groups at positions 1, 2 and 4 and a propen-1-yl group at position 5. It has been isolated from Acorus.. alpha-asarone : The trans-isomer of asarone.	2.17	1	0	asarone	anticonvulsant; GABA modulator
camalexin camalexin : An indole phytoalexin that is indole substituted at position 3 by a 1,3-thiazol-2-yl group.	2.44	2	0	1,3-thiazoles; indole phytoalexin	metabolite
cinnamaldehyde 3-phenylprop-2-enal : A member of the class of cinnamaldehydes that is prop-2-enal in which a hydrogen at position 3 has been replaced by a phenyl group. The configuration of the double bond is not specified; the name "cinnamaldehyde" is widely used to refer to the E (trans) isomer.. (E)-cinnamaldehyde : The E (trans) stereoisomer of cinnamaldehyde, the parent of the class of cinnamaldehydes.	3.28	6	0	3-phenylprop-2-enal; cinnamaldehydes	antifungal agent; EC 4.3.1.24 (phenylalanine ammonia-lyase) inhibitor; flavouring agent; hypoglycemic agent; plant metabolite; sensitiser; vasodilator agent
trans-4-coumaric acid hydroxycinnamic acid : Any member of the class of cinnamic acids carrying one or more hydroxy substituents.. trans-4-coumaric acid : The trans-isomer of 4-coumaric acid.. 4-coumaric acid : A coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring.	7.11	75	1	4-coumaric acid	food component; mouse metabolite; plant metabolite
glycosides [no description available]	11.64	28	0
chalcone trans-chalcone : The trans-isomer of chalcone.	1.95	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.	5.71	25	0	sinapic acid	MALDI matrix material; plant metabolite
isomethyleugenol Methylation: Addition of methyl groups. In histo-chemistry methylation is used to esterify carboxyl groups and remove sulfate groups by treating tissue sections with hot methanol in the presence of hydrochloric acid. (From Stedman, 25th ed)	6.51	58	0	isomethyleugenol
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.	3.56	2	0	enal; monoterpenoid; polyprenal	plant metabolite; volatile oil component
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	9.1	14	0	stilbene
p-hydroxycinnamaldehyde p-hydroxycinnamaldehyde: an antibacterial substance from the saw fly, Acantholyda parki S.; structure in first source. 4-hydroxycinnamaldehyde : A cinnamaldehyde that is (E)-cinnamaldehyde substituted at position 4 on the phenyl ring by a hydroxy group.	8.64	9	0	cinnamaldehydes	apoptosis inducer; EC 1.14.13.39 (nitric oxide synthase) inhibitor; plant metabolite
sorbic acid Sorbic Acid: Mold and yeast inhibitor. Used as a fungistatic agent for foods, especially cheeses.. (2E,4E)-hexa-2,4-dienoic acid : A sorbic acid having trans-double bonds at positions 2 and 4; a food preservative that can induce cutaneous vasodilation and stinging upon topical application to humans. It is the most thermodynamically stable of the four possible geometric isomers possible, as well as the one with the highest antimicrobial activity.. sorbic acid : A hexadienoic acid with double bonds at C-2 and C-4; it has four geometrical isomers, of which the trans,trans-form is naturally occurring.	5.17	12	0	alpha,beta-unsaturated monocarboxylic acid; sorbic acid
citraconic acid citraconic acid: was MH 1975-92 (see under MALEATES 1975-90); METHYLMALEIC ACID was see CITRACONIC ACID 1975-92; use MALEATES to search CITRACONIC ACID 1975-92; RN refers to (Z)-isomer; SO refers to (E)-isomer. citraconic acid : A dicarboxylic acid consisting of maleic acid having a methyl substituent at the 2-position.	2.13	1	0	dicarboxylic acid; dicarboxylic fatty acid	human metabolite
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)	4.64	8	0	flavin adenine dinucleotide; vitamin B2	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; prosthetic group
buprenorphine Buprenorphine: A derivative of the opioid alkaloid THEBAINE that is a more potent and longer lasting analgesic than MORPHINE. It appears to act as a partial agonist at mu and kappa opioid receptors and as an antagonist at delta receptors. The lack of delta-agonist activity has been suggested to account for the observation that buprenorphine tolerance may not develop with chronic use.. buprenorphine : A morphinane alkaloid that is 7,8-dihydromorphine 6-O-methyl ether in which positions 6 and 14 are joined by a -CH2CH2- bridge, one of the hydrogens of the N-methyl group is substituted by cyclopropyl, and a hydrogen at position 7 is substituted by a 2-hydroxy-3,3-dimethylbutan-2-yl group. It is highly effective for the treatment of opioid use disorder and is also increasingly being used in the treatment of chronic pain.	3.35	1	0	morphinane alkaloid	delta-opioid receptor antagonist; kappa-opioid receptor antagonist; mu-opioid receptor agonist; opioid analgesic
pyrophosphate Diphosphates: Inorganic salts of phosphoric acid that contain two phosphate groups.	8.22	5	0	diphosphate ion
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.	2.08	1	0	hydroxypolyether	hepatotoxic agent; nonionic surfactant; sclerotherapy agent
sodium metabisulfite sodium metabisulfite: request from searcher; RN given refers to disulfurous acid, di-Na salt. sodium disulfite : An inorganic sodium salt composed of sodium and disulfite ions in a 2:1 ratio.	1.98	1	0	inorganic sodium salt	food antioxidant
sesquiterpenes [no description available]	5.27	16	0
methylthiouracil Methylthiouracil: A thiourea antithyroid agent that inhibits the synthesis of thyroid hormone. It is used in the treatment of hyperthyroidism.	1.98	1	0	pyrimidone
3,3',4,5'-tetrahydroxystilbene 3,3',4,5'-tetrahydroxystilbene: demethyl derivative of isorhapontigenin; structure in first source; a Syk kinase inhibitor; found in heartwood of FABACEAE; inhibitor of photosynthesis in spinach chloroplasts; may be inhibitor of plant growth; RN given refers to (E)-isomer. piceatannol : A stilbenol that is trans-stilbene in which one of the phenyl groups is substituted by hydroxy groups at positions 3 and 4, while the other phenyl group is substituted by hydroxy groups at positions 3 and 5.	3.31	5	0	catechols; polyphenol; resorcinols; stilbenol	antineoplastic agent; apoptosis inducer; geroprotector; hypoglycemic agent; plant metabolite; protein kinase inhibitor; tyrosine kinase inhibitor
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	5.62	23	0	caffeic acid	geroprotector; mouse metabolite
methyl caffeate methyl caffeate: from plant Gaillardia pulchella. methyl caffeate : An alkyl caffeate ester formed by the formal condensation of caffeic acid with methyl alcohol.	2.46	2	0	alkyl caffeate ester; methyl ester
captax captax: RN given refers to parent cpd. 1,3-benzothiazole-2-thiol : 1,3-Benzothiazole substituted at the 2-position with a sulfanyl group.	2.21	1	0	aryl thiol; benzothiazoles	carcinogenic agent; metabolite
1,6-anhydro-3,4-dideoxy-beta-d-glycero-hex-3-enopyran-2-ulose 1,6-anhydro-3,4-dideoxyhex-3-enopyran-2-ulose: structure in first source	2.6	1	0	anhydrohexose; deoxyketohexose
pyrantel Pyrantel: A depolarizing neuromuscular-blocking agent, that causes persistent nicotinic activation resulting in spastic paralysis of susceptible nematodes. It is a drug of second-choice after benzimidazoles for treatment of ascariasis, hookworm, and pinworm infections, being effective after a single dose. (From Smith and Reynard, Textbook of Pharmacology, 1992, p920). pyrantel : A carboxamidine that is 1,4,5,6-tetrahydropyrimidine that is substituted at position 1 by a methyl group and at position 2 by an (E)-2-(2-thienyl)vinyl group. It is used, particularly as the embonate [4,4'-methylenebis(3-hydroxy-2-naphthoate)] salt, as an anthelmintic that is effective against intestinal nematodes including threadworms, roundworms and hookworms, and is included in the WHO 'Model List of Essential Medicines'.	2.15	1	0	1,4,5,6-tetrahydropyrimidines; carboxamidine; thiophenes	antinematodal drug
3-(3,4-dimethoxyphenyl)propenoic acid 3-(3,4-dimethoxyphenyl)propenoic acid: structure given in first source; RN given refers to parent cpd. 3,4-dimethoxycinnamic acid : A methoxycinnamic acid that is trans-cinnamic acid substituted by methoxy groups at positions 3' and 4' respectively.	2	1	0	methoxycinnamic acid
ethyl ferulate ethyl ferulate: structure in first source	2.02	1	0
isoeugenol trans-isoeugenol : The trans-stereoisomer of isoeugenol.	8.97	3	0	isoeugenol	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.	3.64	7	0	aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger
nootkatone nootkatone: RN given refers to cpd without isomeric designation; structure given in first source. (+)-nootkatone : A sesquiterpenoid that is 4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one which is substituted by methyl groups at positions 4 and 4a, and by an isopropenyl group at position 6 (the 4R,4aS,6R stereoisomer).	2.06	1	0	carbobicyclic compound; enone; sesquiterpenoid	fragrance; insect repellent; plant metabolite
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.	2.81	3	0	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
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.	6.77	75	0	guaiacols; phenylpropanoid	animal metabolite; monolignol; mouse metabolite; pheromone; 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.	5.32	17	0	cinnamate ester; tannin	food component; plant metabolite
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.	7.59	2	0	one-carbon compound; thioureas; ureas	antioxidant; chromophore
safranine t safranin O : An organic chloride salt having 3,7-diamino-2,8-dimethyl-5-phenylphenazin-5-ium as the counterion. It is commonly used for staining Gram negative bacteria.	3.02	4	0	organic chloride salt	fluorochrome; histological dye
indigo carmine Indigo Carmine: Indolesulfonic acid used as a dye in renal function testing for the detection of nitrates and chlorates, and in the testing of milk.. indigo carmine : An organic sodium salt resulting from the formal condensation of indigo carmine (acid form) with two equivalents of sodium hydroxide. It is an indicator at pH 11.5-14, changing from blue to yellow.	2.43	2	0
D-fructopyranose [no description available]	4.22	17	0	cyclic hemiketal; D-fructose; fructopyranose	sweetening agent
tempo TEMPO: structure. TEMPO : A member of the class of aminoxyls that is piperidine that carries an oxidanediyl group at position 1 and methyl groups at positions 2, 2, 6, and 6, respectively.	8.64	8	0	aminoxyls; piperidines	catalyst; ferroptosis inhibitor; radical scavenger
1,6-anhydro-beta-glucopyranose 1,6-anhydro-beta-glucopyranose: RN given refers to (beta-D)-isomer. levoglucosan : A anhydrohexose that is the 1,6-anhydro-derivative of beta-D-glucopyranose.	3.83	10	0	anhydrohexose	Arabidopsis thaliana metabolite; biomarker; human 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	2.08	1	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	2.05	1	0
methyltrioxorhenium methyltrioxorhenium VII: reagent used as an oxidation catalyst for a wide range of materials	7.43	2	0
1-butyl-3-methylimidazolium chloride 1-butyl-3-methylimidazolium chloride: structure in first source	4.04	13	0
1-butyl-3-methylimidazolium 1-butyl-3-methylimidazolium: structure in first source. 1-butyl-3-methylimidazolium : A 1-alkyl-3-methylimidazolium in which the alkyl substituent at C-1 is butyl.	9.07	13	0	1-alkyl-3-methylimidazolium
1-hexyl-3-methylimidazolium 1-hexyl-3-methylimidazolium: structure in first source. 1-hexyl-3-methylimidazolium : A 1-alkyl-3-methylimidazolium in which the alkyl substituent at C-1 is hexyl.	2.08	1	0	1-alkyl-3-methylimidazolium
1-hexylpyridinium [no description available]	2.08	1	0
nadp [no description available]	9.33	19	0
scandium triflate scandium triflate: structure in first source	2.1	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)	4.27	16	0
erythronic acid erythronic acid : The erythro-isomer of 2,3,4-trihydroxybutanoic acid.. D-erythronic acid : An erythronic acid in which the stereocentres at positions 2 and 3 both have R-configuration (the D-enantiomer).. erythronate : A hydroxy monocarboxylic acid anion obtained by deprotonation of the carboxy group of any erythronic acid; major species at pH 7.3.	2.07	1	0	erythronic acid
disperse blue 79 [no description available]	2.25	1	0
laccase Laccase: A copper-containing oxidoreductase enzyme that catalyzes the oxidation of 4-benzenediol to 4-benzosemiquinone. It also has activity towards a variety of O-quinols and P-quinols. It primarily found in FUNGI and is involved in LIGNIN degradation, pigment biosynthesis and detoxification of lignin-derived products.	12.44	615	0
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.	5.25	12	0	alkali metal atom
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.	2.07	1	0	nitrogen oxide
decyl glucoside decyl glucoside: a non-ionic surfactant used in rinse-off products	2.07	1	0
quinine [no description available]	1.94	1	0	cinchona alkaloid	antimalarial; muscle relaxant; non-narcotic analgesic
hydroxyethyl methacrylate-ethyl methacrylate [no description available]	2.04	1	0
xylose-glucose [no description available]	2.85	3	0
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	4.51	7	0
ginsenosides ginsenoside : Triterpenoid saponins with a dammarane-like skeleton originally isolated from ginseng (Panax) species. Use of the term has been extended to include semi-synthetic derivatives.	2.11	1	0
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	7.25	1	0
sodium dodecyl sulfate Sodium Dodecyl Sulfate: An anionic surfactant, usually a mixture of sodium alkyl sulfates, mainly the lauryl; lowers surface tension of aqueous solutions; used as fat emulsifier, wetting agent, detergent in cosmetics, pharmaceuticals and toothpastes; also as research tool in protein biochemistry.. sodium dodecyl sulfate : An organic sodium salt that is the sodium salt of dodecyl hydrogen sulfate.	8.02	4	0	organic sodium salt	detergent; protein denaturant
galactomannan galactomannan: a galectin inhibitor. galactomannan : A heteroglycan consisting of a mannan backbone with galactose side groups.	2.55	2	0	oligosaccharide
alizarin red s Alizarin Red S: RN given refers to parent cpd; structure. alizarin red S : An organic sodium salt having 3,4-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate as the counterion. It is commonly used to stain embryo skeletons in cleared whole mounts, usually of small mammals.	2.17	1	0	organic sodium salt; organosulfonate salt	histological dye
alpha-chymotrypsin Chymotrypsin: A serine endopeptidase secreted by the pancreas as its zymogen, CHYMOTRYPSINOGEN and carried in the pancreatic juice to the duodenum where it is activated by TRYPSIN. It selectively cleaves aromatic amino acids on the carboxyl side.	2.65	3	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.	2.02	1	0
sodium borohydride sodium borohydride: RN given refers to parent cpd	8.37	6	0	inorganic sodium salt; metal tetrahydridoborate
hydroxyethylcellulose hydroxyethylcellulose: component of contact lens wetting solutions; aldiamed is an artificial saliva; RN given refers to parent cpd. hydroxyethylcellulose : A polysaccharide derivative that is cellulose in which hydroxyethyl groups are bound to some of the hydroxyl groups of the glucopyranose monomers.	2.63	2	0
osteoprotegerin Osteoprotegerin: A secreted member of the TNF receptor superfamily that negatively regulates osteoclastogenesis. It is a soluble decoy receptor of RANK LIGAND that inhibits both CELL DIFFERENTIATION and function of OSTEOCLASTS by inhibiting the interaction between RANK LIGAND and RECEPTOR ACTIVATOR OF NUCLEAR FACTOR-KAPPA B.	2.1	1	0	long-chain fatty acid
2-mercaptoacetate 2-mercaptoacetate: RN given refers to parent cpd	3.08	4	0	monocarboxylic acid anion
diethyl maleate diethyl maleate : A maleate ester resulting from the formal condensation of both carboxy groups of maleic acid with ethanol. A colourless liquid at room temperature (m.p. -10degreeC) with boiling point 220degreeC at 1 atm., it is commonly used as a dienophile for Diels-Alder-type cycloaddition reactions in organic synthesis.	7.6	1	0	ethyl ester; maleate ester	glutathione depleting agent
olivil olivil: from the olive tree (Olea europaea Linne; Oleaceae); structure in first source	2.11	1	0
quercetin [no description available]	3.87	11	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
coniferin coniferin : A monosaccharide derivative that is coniferol attached to a beta-D-glucopyranosyl residue at position 1 via a glycosidic linkage.	8.71	10	0	aromatic ether; cinnamyl alcohol beta-D-glucoside; monosaccharide derivative	plant metabolite
luteolin [no description available]	2.63	2	0	3'-hydroxyflavonoid; tetrahydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; apoptosis inducer; c-Jun N-terminal kinase inhibitor; EC 2.3.1.85 (fatty acid synthase) inhibitor; immunomodulator; nephroprotective agent; plant metabolite; radical scavenger; vascular endothelial growth factor receptor antagonist
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.	8.15	5	0	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
pinosylvin pinosylvin: phytoalexin found in pine and eucalyptus	2.08	1	0	pinosylvin
scopoletin [no description available]	2.79	3	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.	1.95	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.	2.89	3	0	carotenoid beta-end derivative; cyclic carotene	antioxidant; biological pigment; cofactor; ferroptosis inhibitor; human metabolite; mouse metabolite; plant metabolite; provitamin A
maleoylacetic acid maleoylacetic acid: RN given refers to (Z)-isomer. maleylacetic acid : A 4-oxohex-2-enedioic acid with a Z-configuration.. 4-oxohex-2-enedioate : An oxo dicarboxylate that is the conjugate base of 4-oxohex-2-enedioic acid.. maleylacetate : A 4-oxohex-2-enedioate that is the conjugate base of maleylacetic acid.	1.98	1	0	4-oxohex-2-enedioic acid	bacterial xenobiotic metabolite
sinapyl alcohol sinapyl alcohol: has anti-inflammatory and antinociceptive properties; structure in first source. trans-sinapyl alcohol : Sinapyl alcohol in which the configuration of the propenyl double bond is E. It is one of the main monolignols.. sinapyl alcohol : A primary alcohol, being cinnamyl alcohol hydroxylated at C-4 and methoxylated at C-3 and -5.	4.67	26	0	sinapyl alcohol	monolignol
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.	4.56	23	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	2.15	1	0	tyramines	metabolite
4-coumaroylshikimic acid [no description available]	2.49	2	0	alpha,beta-unsaturated monocarboxylic acid; cyclohexenecarboxylic acid
hymecromone Hymecromone: A coumarin derivative possessing properties as a spasmolytic, choleretic and light-protective agent. It is also used in ANALYTICAL CHEMISTRY TECHNIQUES for the determination of NITRIC ACID.	2.01	1	0	hydroxycoumarin	antineoplastic agent; hyaluronic acid synthesis inhibitor
daphnetin [no description available]	2.01	1	0	hydroxycoumarin
rosin rosin: Resin from plant. Do not confuse with the specific compound: 3-phenyl-2-propenyl-(E)-beta-D-glucopyranoside, also know as rosin.	2.04	1	0
chrysoeriol chrysoeriol: isolated from leaves of Eurya japonica & E. emarginata. 4',5,7-trihydroxy-3'-methoxyflavone : The 3'-O-methyl derivative of luteolin.	2.04	1	0	monomethoxyflavone; trihydroxyflavone	antineoplastic agent; antioxidant; metabolite
stigmasterol stigmasta-5,22-dien-3-ol: isolated from freeze-dried powder of Blackberries (Rubus ursinus L.) which showed an activity on inhibition of chemocarcinogen. stigmasterol : A 3beta-sterol that consists of 3beta-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions.	2.13	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols; stigmastane sterol	plant metabolite
sinapaldehyde sinapyl aldehyde: structure in first source. (E)-sinapaldehyde : A member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5.	3.64	9	0	cinnamaldehydes; dimethoxybenzene; phenols	antifungal agent; plant metabolite
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	2.71	3	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
genistein [no description available]	7.69	3	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
entacapone entacapone: structure given in first source. entacapone : A monocarboxylic acid amide that is N,N-diethylprop-2-enamide in which the hydrogen at position 2 is substituted by a cyano group and the hydrogen at the 3E position is substituted by a 3,4-dihydroxy-5-nitrophenyl group.	7.25	1	0	2-nitrophenols; catechols; monocarboxylic acid amide; nitrile	antidyskinesia agent; antiparkinson drug; central nervous system drug; EC 2.1.1.6 (catechol O-methyltransferase) inhibitor
erucic acid [no description available]	2.54	2	0	docosenoic acid
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.	6.21	39	0	oxo monocarboxylic acid	jasmonates; 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.	2.08	1	0	carotenol; carotenone	animal metabolite; anticoagulant; antioxidant; food colouring; plant metabolite
mezerein mezerein: toxic component of plant Daphne mezereum with anti-leukemic activity against P-388 & P-1210 in mice; can act as a tumor promoter; RN given refers to (12beta(E,E))-isomer; structure	3.23	1	0	diterpenoid
esculetin esculetin: used in filters for absorption of ultraviolet light; structure. esculetin : A hydroxycoumarin that is umbelliferone in which the hydrogen at position 6 is substituted by a hydroxy group. It is used in filters for absorption of ultraviolet light.	2.04	1	0	hydroxycoumarin	antioxidant; plant metabolite; ultraviolet filter
humulene humulene: structure given in first source. (1E,4E,8E)-alpha-humulene : The (1E,4E,8E)-isomer of alpha-humulene.	7.88	31	1	alpha-humulene
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.	2.25	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
zearalenone Zearalenone: (S-(E))-3,4,5,6,8,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione. One of a group of compounds known under the general designation of resorcylic acid lactones. Cis, trans, dextro and levo forms have been isolated from the fungus Gibberella zeae (formerly Fusarium graminearum). They have estrogenic activity, cause toxicity in livestock as feed contaminant, and have been used as anabolic or estrogen substitutes.. zearalenone : A macrolide comprising a fourteen-membered lactone fused to 1,3-dihydroxybenzene; a potent estrogenic metabolite produced by some Giberella species.	8.46	1	1	macrolide; resorcinols	fungal metabolite; mycoestrogen
myricetin [no description available]	7.6	1	0	7-hydroxyflavonol; hexahydroxyflavone	antineoplastic agent; antioxidant; cyclooxygenase 1 inhibitor; food component; geroprotector; hypoglycemic agent; plant metabolite
rhamnetin rhamnetin: aglycone of xanthorhamnin; from Rhamnus. rhamnetin : A monomethoxyflavone that is quercetin methylated at position 7.	2.07	1	0	monomethoxyflavone; tetrahydroxyflavone	anti-inflammatory agent; antioxidant; metabolite
tricetin tricetin : Flavone hydroxylated at positions 3', 4', 5, 5' and 7.	2.15	1	0	pentahydroxyflavone	antineoplastic agent; metabolite
tricin tricin: from Spartina cynosuroides and other plants; structure	4.04	12	0	3'-methoxyflavones; dimethoxyflavone; trihydroxyflavone	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; metabolite
wogonin wogonin: structure in first source. wogonin : A dihydroxy- and monomethoxy-flavone in which the hydroxy groups are positioned at C-5 and C-7 and the methoxy group is at C-8.	2.55	2	0	dihydroxyflavone; monomethoxyflavone	angiogenesis inhibitor; antineoplastic agent; cyclooxygenase 2 inhibitor; plant metabolite
daidzein [no description available]	2.69	3	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
astringin astringin: structure in first source. trans-astringin : A stilbenoid that is piceatannol substituted at position 3 by a beta-D-glucosyl residue.	2.21	1	0	beta-D-glucoside; monosaccharide derivative; polyphenol; stilbenoid	antineoplastic agent; antioxidant; metabolite
diferulic acid diferulic acid: structure of 8-5'-diferulic acid in first source	2.76	3	0
rosmarinic acid rosmarinic acid: RN given refers to parent cpd; promote OT project. (R)-rosmarinic acid : A stereoisomer of rosmarinic acid having (R)-configuration.. rosmarinic acid : The 1-carboxy-2-(2,4-dihydroxyphenyl)ethyl ester of trans-caffeic acid.	2.85	3	0	rosmarinic acid	geroprotector; plant metabolite
salvianolic acid a salvianolic acid A: a nootropic depside from Salvia miltiorrhizia	2.41	1	0	stilbenoid
acteoside acteoside: a protein kinase C inhibitor with hepatoprotective, anti-asthmatic, and analgesic activities; a phenylethanoid glycoside related to isoacteoside; from leaves of Lippia multiflora (Verbenaceae). acteoside : A glycoside that is the alpha-L-rhamnosyl-(1->3)-beta-D-glucoside of hydroxytyrosol in which the hydroxy group at position 4 of the glucopyranosyl moiety has undergone esterification by formal condensation with trans-caffeic acid.	3.61	2	0	catechols; cinnamate ester; disaccharide derivative; glycoside; polyphenol	anti-inflammatory agent; antibacterial agent; antileishmanial agent; neuroprotective agent; plant metabolite
ellagic acid [no description available]	3.05	1	0	catechols; cyclic ketone; lactone; organic heterotetracyclic compound; polyphenol	antioxidant; EC 1.14.18.1 (tyrosinase) inhibitor; EC 2.3.1.5 (arylamine N-acetyltransferase) inhibitor; EC 2.4.1.1 (glycogen phosphorylase) inhibitor; EC 2.5.1.18 (glutathione transferase) inhibitor; EC 2.7.1.127 (inositol-trisphosphate 3-kinase) inhibitor; EC 2.7.1.151 (inositol-polyphosphate multikinase) inhibitor; EC 2.7.4.6 (nucleoside-diphosphate kinase) inhibitor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; food additive; fungal metabolite; geroprotector; plant metabolite; skin lightening agent
savinin savinin: a lignan from Pterocarpus santalinus inhibits tumor necrosis factor-alpha production and T cell proliferation; structure in first source. savinin : A lignan that is dihydrofuran-2(3H)-one (gamma-butyrolactone) substituted by a 1,3-benzodioxol-5-ylmethylidene group at position 3 and a 1,3-benzodioxol-5-ylmethyl group at position 4 (the 3E,4R-isomer). It exhibits antiviral activity against SARS-CoV-2.	2.02	1	0	benzodioxoles; gamma-lactone; lignan	anti-inflammatory agent; anticoronaviral agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; plant metabolite; T-cell proliferation inhibitor
4',7-dihydroxyflavone 4',7-dihydroxyflavone: inducer of nod gene. 4',7-dihydroxyflavone : A dihydroxyflavone in which the two hydroxy substituents are located at positions 4' and 7.	2.17	1	0	dihydroxyflavone	metabolite
3-amino-1,4-dimethyl-5h-pyrido(4,3-b)indole 3-amino-1,4-dimethyl-5H-pyrido(4,3-b)indole: structure	2.02	1	0	pyridoindole
naloxone Naloxone: A specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors.. naloxone : A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.	3.35	1	0	morphinane alkaloid; organic heteropentacyclic compound; tertiary alcohol	antidote to opioid poisoning; central nervous system depressant; mu-opioid receptor antagonist
cellodextrin cellodextrin: can be metabolized by some yeast species. cellooligosaccharide : An oligosaccharide with between two and about 20 D-glucose residues connected by mixed alpha and beta (1->4) glycosidic linkages.. cellodextrin : A dextrin of varying length (two or more glucose monomers) resulting from cellulolysis, the breakdown of cellulose.	3.54	7	0	glucotriose	bacterial xenobiotic metabolite
xylulose [no description available]	4.1	4	0	xylulose	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
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.	1.95	1	0	1-O-acyl-sn-glycero-3-phosphocholine
cinnamyl alcohol cinnamyl alcohol: RN given refers to parent cpd without isomeric designation. (E)-cinnamyl alcohol : The E (trans) stereoisomer of cinnamyl alcohol.. cinnamyl alcohol : A primary alcohol comprising an allyl core with a hydroxy substituent at the 1-position and a phenyl substituent at the 3-position (geometry of the C=C bond unspecified).	3.63	9	0	cinnamyl alcohol	plant metabolite
syringin syringin: a phenylpropanoid glycoside; see also eleutherosides & lyoniside for eleutheroside A: 474-58-8. syringin : A monosaccharide derivative that is trans-sinapyl alcohol attached to a beta-D-glucopyranosyl residue at position 1 via a glycosidic linkage.	2.93	4	0	beta-D-glucoside; dimethoxybenzene; monosaccharide derivative; primary alcohol	hepatoprotective agent; plant metabolite
ailanthoidol ailanthoidol: from Zanthoxylum ailanthoidos; structure in first source	2.01	1	0
beta-farnesene beta-farnesene: structure given in first source	2.21	1	0	beta-farnesene
isorhapontigenin isorhapontigenin: isolated from the seeds of Aiphanes aculeata Willd. (Arecaceae); structure in first source	2.21	1	0	stilbenoid
methyl-p-coumarate methyl-p-coumarate: structure in first source. 4-coumaric acid methyl ester : A cinnamate ester that is the methyl ester of 4-coumaric acid.	1.93	1	0	4-coumaric acid methyl ester
octadecyl caffeate caffeic acid n-octadecyl ester: isolated from Daphne acutiloba Rehd; structure in first source	2.07	1	0
diferuloylputrescine diferuloylputrescine: structure in first source	2.66	2	0	hydroxycinnamic acid
ergothioneine ergothioneine thione form : A L-histidine derivative that is N(alpha),N(alpha),N(alpha)-trimethyl-L-histidine in which the hydrogen at position 2 on the imdazole ring is replaced by a thioxo group.	2.6	1	0	1,3-dihydroimidazole-2-thiones; amino-acid betaine; L-histidine derivative; sulfur-containing amino acid	antioxidant; chelator; fungal metabolite; plant metabolite; xenobiotic metabolite
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	5.25	45	0	carbon group element atom; elemental lead; metal atom	neurotoxin
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.	8.51	7	0	alkali metal atom
7,8-dihydroxy-4-methylcoumarin 7,8-dihydroxy-4-methylcoumarin: possess strong antioxidant and radical scavenging activities; structure in first source	2.01	1	0	hydroxycoumarin
muconic acid muconic acid: a metabolite of benzene; reported to be a reliable indicator of occupational exposure to benzene; structure given in first source. trans,trans-muconic acid : The trans,trans-isomer of muconic acid. It is metabolite of benzene in humans and serves as a biomarker of occupational exposure to benzene.. muconic acid : A hexadienedioic acid with unsaturation at positions 2 and 4.	5.11	11	0	muconic acid	biomarker; human xenobiotic metabolite
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	5.75	25	0	boron group element atom; elemental aluminium; metal atom
bismuth Bismuth: A metallic element that has the atomic symbol Bi, and atomic number 83. Its principal isotope is Bismuth 209.	4.9	1	1	metal atom; pnictogen
thallium Thallium: A heavy, bluish white metal, atomic number 81, atomic weight [204.382; 204.385], symbol Tl.. thallium : A metallic element first identified and named from the brilliant green line in its flame spectrum (from Greek thetaalphalambdalambdaomicronsigma, a green shoot).	7.6	1	0	boron group element 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)	5.73	14	0	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.	2.69	2	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.	3.35	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.	2.07	1	0	boron group element atom
ramipril Ramipril: A long-acting angiotensin-converting enzyme inhibitor. It is a prodrug that is transformed in the liver to its active metabolite ramiprilat.. ramipril : A dipeptide that is the prodrug for ramiprilat, the active metabolite obtained by hydrolysis of the ethyl ester group. An angiotensin-converting enzyme (ACE) inhibitor, used to treat high blood pressure and congestive heart failure.. quark : Quarks comprise one of two classes of the fundamental particles. Quarks possess fractional electric charges and are not observed in free state. The word "quark" first appears in James Joyce's Finnegans Wake and has been chosen by Murray Gell-Mann as a name for fundamental building blocks of particles.	2.41	1	0	azabicycloalkane; cyclopentapyrrole; dicarboxylic acid monoester; dipeptide; ethyl ester	bradykinin receptor B2 agonist; cardioprotective agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; matrix metalloproteinase inhibitor; prodrug
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.	7.83	34	0	chalcogen; nonmetal atom	macronutrient
methoprene Methoprene: Juvenile hormone analog and insect growth regulator used to control insects by disrupting metamorphosis. Has been effective in controlling mosquito larvae.	3.06	1	0	isopropyl 11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate; isopropyl ester	juvenile hormone mimic
indole-3-acetaldoxime (E)-indol-3-ylacetaldehyde oxime : An indol-3-ylacetaldehyde oxime in which the oxime moiety has E configuration.	2.11	1	0	indol-3-ylacetaldehyde oxime
isoalloxazine isoalloxazine: structure	2.03	1	0	benzo[g]pteridine-2,4-dione
diphenylhexatriene Diphenylhexatriene: A fluorescent compound that emits light only in specific configurations in certain lipid media. It is used as a tool in the study of membrane lipids.	2.07	1	0	alkatriene	fluorochrome
hinokiresinol hinokiresinol: RN given for (S-(E))-isomer; inhibits binding of leukotriene B4 to neutrophils; structurein first source	2.02	1	0
aldosterone dehydrodiisoeugenol: an isoeugenol dimer, inhibits lipopolysaccharide-stimulated nuclear factor kappa B activation and cyclooxygenase-2 expression in macrophages; structure in first source	2.04	1	0
puerarin [no description available]	7.6	1	0	C-glycosyl compound; isoflavonoid
fumarates Fumarates: Compounds based on fumaric acid.. fumarate(2-) : A C4-dicarboxylate that is the E-isomer of but-2-enedioate(2-)	4.61	7	0	butenedioate; C4-dicarboxylate	human metabolite; metabolite; Saccharomyces cerevisiae metabolite
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.	4.9	1	1	alkaline earth metal atom; elemental beryllium; metal allergen	adjuvant; carcinogenic agent; epitope
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.	3.48	7	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].	6.78	22	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.	8.45	59	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.	5.24	7	0	boron group element atom; metalloid atom; nonmetal atom	micronutrient
2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid 2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid: chromogen in glucose oxidase-peroxidase method for determining serum glucose; used in free radical scavenging assays; structure in first source	4.49	22	0
panaxynol [no description available]	2.06	1	0	long-chain fatty alcohol
caesium-137 [no description available]	7.41	1	0	caesium atom
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.	4.93	31	0	2-trans-abscisic acid
cefotaxime Cefotaxime: Semisynthetic broad-spectrum cephalosporin.. cefotaxime : A cephalosporin compound having acetoxymethyl and [2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino side groups.	2.6	1	0	1,3-thiazoles; cephalosporin; oxime O-ether	antibacterial drug; drug allergen
cinidon-ethyl Lotus: A genus of the PEA FAMILY. The genus Lotus, formerly known as Tetragonolobus, is unrelated to other plants with the common name of lotus (NELUMBO and NYMPHAEA).. cinidon ethyl : A carboxylic ester and organochlorine compound that is the ethyl ester of cinidon.	3.37	5	0	ethyl ester; isoindoles; monochlorobenzenes	herbicide
ammonium sulfate Ammonium Sulfate: Sulfuric acid diammonium salt. It is used in CHEMICAL FRACTIONATION of proteins.. ammonium sulfate : An inorganic sulfate salt obtained by reaction of sulfuric acid with two equivalents of ammonia. A high-melting (decomposes above 280degreeC) white solid which is very soluble in water (70.6 g/100 g water at 0degreeC; 103.8 g/100 g water at 100degreeC), it is widely used as a fertilizer for alkaline soils.	3.51	7	0	ammonium salt; inorganic sulfate salt	fertilizer
c.i. fluorescent brightening agent 28 4,4'-bis({4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl}amino)stilbene-2,2'-disulfonic acid : An organosulfonic acid comprising stilbene having 4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl}amino groups at the 4 and 4'-positions and sulfo groups at the 2- and 2'-positions.	2.78	3	0
caffeoyl-coenzyme a caffeoyl-coenzyme A: structure given in first source	8.41	7	0
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.	6.17	8	1	chalcogen; nonmetal atom	micronutrient
tellurium Tellurium: An element that is a member of the chalcogen family. It has the atomic symbol Te, atomic number 52, and atomic weight 127.60. It has been used as a coloring agent and in the manufacture of electrical equipment. Exposure may cause nausea, vomiting, and CNS depression.	3.07	3	0	chalcogen; metalloid atom
trimethoxysilane [no description available]	2.07	1	0
triethoxysilane [no description available]	2.13	1	0
oxalates Oxalates: Derivatives of OXALIC ACID. Included under this heading are a broad variety of acid forms, salts, esters, and amides that are derived from the ethanedioic acid structure.	3.9	12	0
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.	2.07	1	0	amidobenzoic acid
guaiacylglycerol-beta-guaiacyl ether guaiacylglycerol-beta-guaiacyl ether: structure given in first source. guaiacylglycerol-beta-guaiacyl ether : A glycerol ether in which guaiacyl and guaiacylglycerol subunits are joined by an arylglycerol-beta-aryl (beta-O-4) linkage.	3.91	12	0	glycerol ether
hygromycin a hygromycin A: a cinnamide derivative produced by Streptomyces hygroscopicus; structure differs from HYGROMYCIN B	2.52	2	0	hydroxycinnamic acid	metabolite
falcarindiol falcarindiol: from leaves of Schefflera digitata (Araliaceae) and in carrots; inhibits germination of spores of most common dermatophyte fungi	2.06	1	0	organic molecular entity	metabolite
uniconazole uniconazole: structural analog of diniconazole; RN refers to ((E)-(+-))-isomer; structure given in first source. uniconazole : A racemate comprising equimolar amounts of uniconazole-P and its enantiomer, (R)-uniconazole.. (1E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol : A member of the class of triazoles that is 1,2,4-triazole which is substituted at position 1 by a 1-(p-chlorophenyl)-3-hydroxy-4,4-dimethylpent-1-en-2-yl group.	2.83	3	0	monochlorobenzenes; secondary alcohol; triazoles
dioleoyl phosphatidylethanolamine dioleoyl phosphatidylethanolamine: chemical name in article is incorrect - phosphatidylethandamine instead of phosphatidylethanolamine. dioleoyl phosphatidylethanolamine : A phosphatidylethanolamine in which the phosphatidyl acyl groups are both oleoyl.	2.25	1	0	phosphatidylethanolamine
thermozymocidin thermozymocidin: a serine palmitoyltransferase inhibitor; FTY720 is an analog	2.13	1	0	alpha-amino fatty acid; hydroxy monocarboxylic acid; non-proteinogenic alpha-amino acid; sphingoid	antifungal agent; antimicrobial agent; antineoplastic agent; apoptosis inducer; EC 2.3.1.50 (serine C-palmitoyltransferase) inhibitor; fungal metabolite; immunosuppressive agent
4-coumaroyl-coenzyme a 4-coumaroyl-coenzyme A: structure given in first source. trans-4-coumaroyl-CoA : A 4-coumaroyl-CoA in which the double bond of the coumaroyl group has trans-geochemistry.. 4-coumaroyl-CoA : The S-(4-coumaroyl) derivative of coenzyme A.	2.48	2	0	4-coumaroyl-CoA
isopentenol isopentenol : An enol that is 3-methylbut-1-ene in which one of the terminal hydrogens is replaced by a hydroxy group.	7.25	1	0	enol
acuminatin acuminatin: from Epimedium acuminatum; Chemline give RN 41744-39-2 for acuminatin, but the compound has a different structure than the one given in journal. acuminatin : A neolignan that is 5-[(1E)-prop-1-en-1-yl]-2,3-dihydro-1-benzofuran carrying additional 3,4-dimethoxyphenyl, methyl and methoxy substituents at positions 2, 3 and 7 respectively.	2.01	1	0	1-benzofurans; dimethoxybenzene; neolignan; olefinic compound; ring assembly	fungal metabolite; plant metabolite
coniferyl ferulate coniferyl ferulate: found in the rhizome of Cnidium officinale Makino; structure given in first source; RN given refers to cpd without isomeric designation	7.04	1	0
cinnamoyl-coenzyme a (E)-cinnamoyl-CoA : The (E)-isomer of cinnamoyl-CoA.	2.02	1	0	cinnamoyl-CoA
idb 1016 [no description available]	2.89	1	0
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.	7.76	3	0
beta-escin [no description available]	5.86	12	0
D-xylonic acid xylonic acid: sugar acid that can be obtained by the complete oxidation of xylose. xylonic acid : A pentonic acid resulting from the formal oxidation of the aldehyde group of aldehydo-xylose to the corresponding carboxylic acid.. D-xylonic acid : A xylonic acid with D configuration.	3.38	5	0	xylonic acid
melibiose alpha-D-Galp-(1->6)-alpha-D-Glcp : A glycosylglucose consisting of alpha-D-galactopyranose and alpha-D-glucopyranose residues joined in sequence by a (1->6) glycosidic bond.	2.04	1	0	glycosylglucose
shellac shellac: RN given refers to parent cpd	2.21	1	0
staurosporine staurosporinium : Conjugate acid of staurosporine.	2.41	2	0	ammonium ion derivative
hypericum Hypericum: Genus of perennial plants in the family CLUSIACEAE (sometimes classified as Hypericaceae). Herbal and homeopathic preparations are used for depression, neuralgias, and a variety of other conditions. Hypericum contains flavonoids; GLYCOSIDES; mucilage, TANNINS; volatile oils (OILS, ESSENTIAL), hypericin and hyperforin.. 6-formamidopenicillanic acid : A penicillanic acid having a (6R)-formamido substituent.	2.05	1	0	penicillanic acids
mannich bases Mannich Bases: Ketonic amines prepared from the condensation of a ketone with formaldehyde and ammonia or a primary or secondary amine. A Mannich base can act as the equivalent of an alpha,beta unsaturated ketone in synthesis or can be reduced to form physiologically active amino alcohols.	2.63	2	0
ferrihydrite ferric oxyhydroxide: an antiferromagnetic material; constitutes the core of natural ferritin; mol form 5Fe2O3.9H2O	3.56	2	0
disilver oxide [no description available]	2.57	2	0
lenvatinib lenvatinib : A member of the class of quinolines that is the carboxamide of 4-{3-chloro-4-[(cyclopropylcarbamoyl)amino]phenoxy}-7-methoxyquinoline-6-carboxylic acid. A multi-kinase inhibitor and orphan drug used (as its mesylate salt) for the treatment of various types of thyroid cancer that do not respond to radioiodine.	4.9	1	1	aromatic amide; aromatic ether; cyclopropanes; monocarboxylic acid amide; monochlorobenzenes; phenylureas; quinolines	antineoplastic agent; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; fibroblast growth factor receptor antagonist; orphan drug; vascular endothelial growth factor receptor antagonist
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).	9.26	155	0	aminopyrimidine; benzamides; pyridines; secondary amino compound; secondary carboxamide; substituted aniline	antineoplastic agent; apoptosis inducer; autophagy inducer; cardioprotective agent; EC 3.5.1.98 (histone deacetylase) inhibitor; hepatotoxic agent
secoisolariciresinol diglucoside secoisolariciresinol diglucoside: major precursor of mammalian lignans; structure given in first source; RN given refers to B-D-GLUCO isomer	5.46	2	0
zeolites [no description available]	6.69	26	0
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.	9.16	14	0
epiyangambin epiyangambin: a furofuran lignan; also a PAF receptor antagonist; from the leaves of Rollinia pickeli; RN given for epiyangambin, the (1S-(1alpha,3aalpha,4beta,6aalpha))-isomer; structure given in first source	1.98	1	0
magnosalin magnosalin: from crude Japanese drug Shin-i; inhibits adjuvant-induced angiogenesis & granuloma formation in the mouse pouch; structure given in first source; RN given refers to cpd without isomeric designation	1.99	1	0	lignan
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
laxogenin laxogenin: structure in first source	7.41	1	0
ribose ribopyranose : The pyranose form of ribose.	3.16	1	0	D-ribose; ribopyranose
molybdenum carbide molybdenum carbide: catalyst for the hydrodeoxygenation of vegetable oils	2.58	2	0
lactulose Lactulose: A synthetic disaccharide used in the treatment of constipation and hepatic encephalopathy. It has also been used in the diagnosis of gastrointestinal disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p887). lactulose : A synthetic galactosylfructose disaccharide used in the treatment of constipation and hepatic encephalopathy.	7.37	2	0
isosilybin a isosilybin A: has antineoplastic activity; structure in first source	2.13	1	0
1-allyl-3-methylimidazolium 1-allyl-3-methylimidazolium: structure in first source	8.35	6	0
cardanol cardanol: from pink pepper; phenol with hydrocarbon side chain which can vary in length & unsaturation	7.31	1	0	phenols
buprenorphine, naloxone drug combination Buprenorphine, Naloxone Drug Combination: A pharmaceutical preparation that combines buprenorphine, an OPIOID ANALGESICS with naloxone, a NARCOTIC ANTAGONISTS to reduce the potential for NARCOTIC DEPENDENCE in the treatment of pain. It may also be used for OPIOID SUBSTITUTION THERAPY.	3.35	1	0
aspalathin aspalathin: structure in first source. aspalathin : A member of the class of dihydrochalcones that is the 2-C-beta-D-glucopyranide of phloroglucinol and which is substituted at position 4 by a 3-(3,4-dihydroxyphenyl)propanoyl group. A metabolite of red bush, Aspalathus linearis (and present in the herbal tea made from the leaves), aspalathin exhibits significant hypoglycemic activity.	2.03	1	0	C-glycosyl compound; catechols; dihydrochalcones; polyketide; polyphenol	antioxidant; EC 1.17.3.2 (xanthine oxidase) inhibitor; hypoglycemic agent; plant metabolite
linoleic acid hydroperoxide linoleic acid hydroperoxide: RN refers to (Z,Z)-isomer. linoleic acid hydroperoxide : A HPODE that is a mono-hydroperoxy derivative of linoleic acid	2	1	0
karrikinolide karrikinolide: a seed germination stimulant formed during burning of plant material; structure in first source	7.31	1	0
2,3,5,6-tetrafluoro-4-methylbenzyl (z)-(1rs)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate 2,3,5,6-tetrafluoro-4-methylbenzyl (Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate: used as an insecticide agent. (Z)-(1S)-cis-tefluthrin : A 2,3,5,6-tetrafluoro-4-methylbenzyl 3-[(1Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl]-2,2-dimethylcyclopropanecarboxylate in which both of the stereocentres have S configuration.	2.06	1	0	2,3,5,6-tetrafluoro-4-methylbenzyl 3-[(1Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl]-2,2-dimethylcyclopropanecarboxylate
eupomatilone-6 eupomatilone-6: structure in first source	2.02	1	0
emamectin benzoate emamectin benzoate: 4'-deoxy-4'-epi-methylamino derivative of avermectin B1; structure given in first source. emamectin : A mixture of emamectin B1a (major component) and emamectin B1b (minor component).	2.9	2	0	emamectins
chlorophyll b [no description available]	2.49	2	0	chlorophyll	cofactor
lyoniresinol lyoniresinol: isoalted from the vine stem of Bauhinia championii; structure in first source. (+)-lyoniresinol : A lignan that is tetralin substituted by a 4-hydroxy-3,5-dimethoxy group at position 4, hydroxymethyl groups at positions 2 and 3, methoxy groups at positions 5 and 7 and a hydroxy group at position 6. Isolated from Machilus robusta and Sinocalamus affinis, it exhibits antineoplastic activity.	2.46	2	0	dimethoxybenzene; lignan; polyphenol; primary alcohol; tetralins	antineoplastic agent; metabolite
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.	1.97	1	0	benzoxazole
dextrothyroxine [no description available]	3.4	5	0
virginiamycin Virginiamycin: A cyclic polypeptide antibiotic complex from Streptomyces virginiae, S. loidensis, S. mitakaensis, S. pristina-spiralis, S. ostreogriseus, and others. It consists of 2 major components, VIRGINIAMYCIN FACTOR M1 and virginiamycin Factor S1. It is used to treat infections with gram-positive organisms and as a growth promoter in cattle, swine, and poultry.. virginiamycin : A mixture of cyclic polypeptide streptogramin antibiotics produced by Streptomyces virginiae, S. loidensis, S. mitakaensis, S. pristina-spiralis, S. ostreogriseus, and others. The two major components are virginiamycin M1 (also known as pristinamycin IIA) and virginiamycin S1. Virginiamycin has been widely used as a growth promotion agent in livestock and has been to have bacteriostatic activity against Gram-positive organisms such as staphylococci and streptococci.	3.42	1	1
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.	4.26	5	0
silidianin [no description available]	2.13	1	0
clove Madagascar: One of the Indian Ocean Islands off the southeast coast of Africa. Its capital is Antananarivo. It was formerly called the Malagasy Republic. Discovered by the Portuguese in 1500, its history has been tied predominantly to the French, becoming a French protectorate in 1882, a French colony in 1896, and a territory within the French union in 1946. The Malagasy Republic was established in the French Community in 1958 but it achieved independence in 1960. Its name was changed to Madagascar in 1975. (From Webster's New Geographical Dictionary, 1988, p714)	2.06	1	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.	3.1	5	0
ants Ants: Insects of the family Formicidae, very common and widespread, probably the most successful of all the insect groups. All ants are social insects, and most colonies contain three castes, queens, males, and workers. Their habits are often very elaborate and a great many studies have been made of ant behavior. Ants produce a number of secretions that function in offense, defense, and communication. (From Borror, et al., An Introduction to the Study of Insects, 4th ed, p676)	3.23	5	0
cleomiscosin d cleomiscosin D: from the root bark of Hibiscus syriacus (Malvaceae); structure in first source	2.03	1	0
curcumol [no description available]	4.9	1	1	sesquiterpenoid
furosine [no description available]	3.51	1	1	alpha-amino acid
lyoniside lyoniside: see also eleutherosides & syringin for eleutheroside B: 118-34-3; RN given refers to (3beta)-isomer	2.49	2	0
2-aminoindan-2-phosphonic acid 2-aminoindan-2-phosphonic acid: inhibits salicylic acid synthesis	2.06	1	0
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	12.67	27	1	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.	4.26	5	0
tannins gallotannin : A class of hydrolysable tannins obtained by condensation of the carboxy group of gallic acid (and its polymeric derivatives) with the hydroxy groups of a monosaccharide (most commonly glucose).	5.38	2	1	tannin
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.	3.14	1	0	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.	9.57	61	1
oligonucleotides [no description available]	2.07	1	0
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	18.8	2,583	8	glycoside
perovskite calcium titanate : A calcium salt with the formula CaTiO3, generally obtained in the form of the mineral perovskite.	3.1	4	0
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	3.85	4	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.	7.12	43	0	chlorophyll; methyl ester	cofactor
bis(tri-n-butyltin)oxide bis(tri-n-butyltin)oxide: RN given refers to parent cpd; RN in Chemline for tributylin: 688-73-3	1.99	1	0	inorganic molecular entity
pinoresinol pinoresinol: in plants; a furo[3,4-c]furan created from dimer of coniferyl alcohol. pinoresinol : A lignan that is tetrahydro-1H,3H-furo[3,4-c]furan substituted at positions 1 and 4 by 4-hydroxy-3-methoxyphenyl groups.	10.15	14	0
lucifer yellow lucifer yellow: RN given refers to di-Li salt	2.04	1	0	organic lithium salt	fluorochrome
5,6,2',3',5',6'-hexamethoxyflavone 5,6,2',3',5',6'-hexamethoxyflavone: from the Yucatec Mayan plant Casimiroa tetrameria; structure in first source	2.47	2	0
chitosan [no description available]	10.37	71	1
alpha-pyrone-4,6-dicarboxylic acid alpha-pyrone-4,6-dicarboxylic acid: structure. 2-oxo-2H-pyran-4,6-dicarboxylate : A dicarboxylic acid dianion obtained via deprotonation of both carboxy groups of 2-oxo-2H-pyran-4,6-dicarboxylic acid; major species at pH 7.3.	4.68	7	0	dicarboxylic acid dianion
muconolactone muconolactone: RN given refers to unlabeled parent cpd; structure given in first source. 5-oxo-2,5-dihydro-2-furylacetate : A monocarboxylic acid anion that is the conjugate base of 5-oxo-2,5-dihydro-2-furylacetic acid, formed via deprotonation of the carboxy group; major species at pH 7.3.	7.13	1	0	monocarboxylic acid anion
osteum [no description available]	2.05	1	0	organic molecular entity
sodium hypochlorite Sodium Hypochlorite: It is used as an oxidizing and bleaching agent and as a disinfectant. (From Grant & Hackh's Chemical Dictionary, 5th ed). sodium hypochlorite : An inorganic sodium salt in which hypochlorite is the counterion. It is used as a bleaching and disinfecting agent and is commonly found in household bleach.	2.95	4	0	inorganic sodium salt	bleaching agent; disinfectant
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	3.86	10	0
stearates Stearates: Salts and esters of the 18-carbon saturated, monocarboxylic acid--stearic acid.	2	1	0
epi-isozizaene epi-isozizaene: structure in first source	2.25	1	0	sesquiterpene
hygromycin b [no description available]	2.52	2	0
methyl jasmonate [no description available]	5.59	21	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.	8.89	12	0	organic cation; sulfonium compound	coenzyme; cofactor; human metabolite; micronutrient; Mycoplasma genitalium metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
ethyl cellulose [no description available]	2.07	1	0	glycoside
superphosphate superphosphate: RN given refers to normal or enriched superphosphate, MF unknown	2.21	1	0
arabinogalactan [no description available]	9.13	4	0
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [no description available]	2.6	1	0	BODIPY compound
aniline blue aniline blue: fluorochrom widely used by botanists	2.1	1	0
mannans [no description available]	8.65	40	2
salicortin salicortin: an aryl glucoside from most species of Salix and Populus; structure in first source	2.01	1	0	glycoside
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)	3.65	9	0
urushiol [no description available]	2.15	1	0
glycolipids [no description available]	3.49	7	0
feruloyl-coa feruloyl-CoA(4-) : An acyl-CoA(4-) that is the tetraanion of feruloyl-CoA arising from deprotonation of the phosphate and diphosphate OH groups.. trans-feruloyl-CoA(4-) : An acyl-CoA(4-) obtained by deprotonation of the phosphate and diphosphate OH groups of 3-trans-feruloyl-CoA. Major structure at pH 7.3.	8.05	4	0	feruloyl-CoA(4-)
bryostatin 1 bryostatin 1: a protein kinase C activator; macrocyclic lactone from marine Bryozoan Bugula neritina; RN given refers to (1S-(1R,3R,5Z,7S,8E,11R,12R(2E,4E),13E,15R,17S(S),21S,23S,25R))-isomer; structure given in first source; activates protein kinase c. bryostatin 1 : A member of the class of bryostatins that is (17E)-2-oxooxacyclohexacos-17-ene which is substituted by hydroxy groups at positions 4, 10, and 20; an acetoxy group at position 8; methyl groups at positions 9, 9, 18, and 19; 2-methoxy-2-oxoethylidene groups at positions 14 and 24; an (E,E)-octa-2,4-dienoyloxy group at position 21; and with oxygen bridges linking positions 6 to 10, 12 to 16, and 20 to 24. It is one of the most abundant member of the class of bryostatins.	3.07	1	0
interleukin-8 Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.	8.12	5	0
punicalagin punicalagin: hepatoprotective agent isolated from Terminalia catappa; structure in first source	2.15	1	0	tannin
colistin Colistin: Cyclic polypeptide antibiotic from Bacillus colistinus. It is composed of Polymyxins E1 and E2 (or Colistins A, B, and C) which act as detergents on cell membranes. Colistin is less toxic than Polymyxin B, but otherwise similar; the methanesulfonate is used orally.. colistin : A multi-component mixture comprising mostly of colistin A (R = Me) and B (R = H), with small amounts of colistin C and other polymyxins, produced by certain strains of Bacillus polymyxa var. colistinus. An antibiotic, it is used as its sulfate salt (for oral or topical use) or as the sodium salt of the N-methylsulfonic acid derivative (the injectable form) in the treatment of severe Gram-negative infections, partiularly those due to Pseudomonas aeruginosa.	4.9	1	1
methylcellulose Methylcellulose: Methylester of cellulose. Methylcellulose is used as an emulsifying and suspending agent in cosmetics, pharmaceutics and the chemical industry. It is used therapeutically as a bulk laxative.	7.95	4	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.	5.53	12	0
heparitin sulfate Heparitin Sulfate: A heteropolysaccharide that is similar in structure to HEPARIN. It accumulates in individuals with MUCOPOLYSACCHARIDOSIS.	2.03	1	0
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	11.18	23	0	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
4-hydroxy-6-methyl-2-pyrone 4-hydroxy-6-methyl-2-pyrone: structure in first source	2.31	1	0	2-pyranones
tetracycline Tetracycline: A naphthacene antibiotic that inhibits AMINO ACYL TRNA binding during protein synthesis.. tetracycline : A broad-spectrum polyketide antibiotic produced by the Streptomyces genus of actinobacteria.	3.8	8	0
oxytetracycline, anhydrous Oxytetracycline: A TETRACYCLINE analog isolated from the actinomycete STREPTOMYCES RIMOSUS and used in a wide variety of clinical conditions.. oxytetracycline : A tetracycline used for treatment of infections caused by a variety of Gram positive and Gram negative microorganisms including Mycoplasma pneumoniae, Pasteurella pestis, Escherichia coli, Haemophilus influenzae (respiratory infections), and Diplococcus pneumoniae.	3.01	2	0
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.	2.57	2	0	monohydroxybenzoate	plant metabolite
nedocromil 3,4-dihydroxybenzoate: structure in first source. 3,4-dihydroxybenzoate : A dihydroxybenzoate having the two hydroxy groups located at the 3- and 4-positions.	2.41	1	0	dihydroxybenzoate
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.	6.28	15	0	benzenes; hydroxycoumarin; methyl ketone
pulvinic acid pulvinic acid: structure in first source	2.15	1	0	butenolide
kaolinite Kaolin: The most common mineral of a group of hydrated aluminum silicates, approximately H2Al2Si2O8-H2O. It is prepared for pharmaceutical and medicinal purposes by levigating with water to remove sand, etc. (From Merck Index, 11th ed) The name is derived from Kao-ling (Chinese: high ridge), the original site. (From Grant & Hackh's Chemical Dictionary, 5th ed). kaolin : An aluminosilicate soft white mineral named after the hill in China (Kao-ling) from which it was mined for centuries. In its natural state kaolin is a white, soft powder consisting principally of the mineral kaolinite, and varying amounts of other minerals such as muscovite, quartz, feldspar, and anatase. It is used in the manufacture of china and porcelain and also widely used in the production of paper, rubber, paint, drying agents, and many other products.	2.6	1	0	aluminosilicate mineral; mixture	antidiarrhoeal drug; excipient
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.	5.4	16	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.	4.93	2	1
phytoestrogens Phytoestrogens: Compounds derived from plants, primarily ISOFLAVONES that mimic or modulate endogenous estrogens, usually by binding to ESTROGEN RECEPTORS.	7.29	10	0
chromated copper arsenate chromated copper arsenate: wood preservative; serves as substrate for trimethylarsine biosynthesis; RN given refers to (Cu(+2)[2:3] salt)	3.06	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]	2.08	1	0
soda lime soda lime: a mixture of calcium oxide (lime) with 5-20% sodium hydroxide and 6-18% water; carbon dioxide adsorbant	2.45	2	0
araldite araldite: induces experimental asthma in immunized guinea pigs; RN given refers to araldite; see also record for araldite B	2.13	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.	8.71	10	0
olivine olivine: sand of primarily magnesium iron silicate, containing low levels of free silica; suggested as a less injurious substitute for silica quartz in foundries; RN in Chemline for unspecified composition: 1317-71-1	7.21	1	0
hypophyllanthin hypophyllanthin: Anti-inflammatory from Phyllanthus amarus	1.98	1	0
alcohol oxidase [no description available]	9.27	5	0
sorbitan monolaurate sorbitan monolaurate: span type materials are artificial esters of the common fatty acids & hexitol anhydrides derived from sorbitol	2.48	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.	3.61	9	0
cellohexaose D-cellohexaose : A hexasaccharide consisting of five beta-D-glucopyranose residues and a D-glucopyranose residue joined in sequence by (1->4) glycosidic bonds.	2.21	1	0	glucohexaose
illite [no description available]	7.72	2	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.	7.42	2	0	phthalocyanines; tetrapyrrole fundamental parent
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	3.85	10	0
xylotriose [no description available]	2.47	2	0
gibberellins [no description available]	5.5	19	0
hexenuronic acid [no description available]	3.46	7	0
t-2 toxin T-2 Toxin: A potent mycotoxin produced in feedstuffs by several species of the genus FUSARIUM. It elicits a severe inflammatory reaction in animals and has teratogenic effects.. T-2 toxin : A trichothecene mycotoxin produced by fungi of the genus Fusarium. It is a common contaminant in food and feedstuffs of cereal origin and is known to cause a range of toxic effects in humans and animals.	2.37	2	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.	2.39	2	0
silybin Silybin: The major active component of silymarin flavonoids extracted from seeds of the MILK THISTLE, Silybum marianum; it is used in the treatment of HEPATITIS; LIVER CIRRHOSIS; and CHEMICAL AND DRUG INDUCED LIVER INJURY, and has antineoplastic activity; silybins A and B are diastereomers.	2.13	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.	5.2	2	1
carboxymethyl-beta-cyclodextrin [no description available]	2.25	1	0
orabase Orabase: used in therapy of oral mucosal ulcers	4.24	15	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.	2.1	1	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.	2.15	1	0
rhamnogalacturonan i rhamnogalacturonan I: pectic polysaccharide from sycamore cell walls; composed of galactosyluronic acid, rhamnosyl, galactosyl, arabinosyl & fucosyl residues. rhamnogalacturonan I : A family of polysaccharides that all contain a linear backbone composed of repeating units of the disaccharide alpha-D-GalpA-(l->2)-alpha-L-Rhap joined by alpha-(1->4) linkages.	2.25	1	0
exudates Malaysia: A parliamentary democracy with a constitutional monarch in southeast Asia, consisting of 11 states (West Malaysia) on the Malay Peninsula and two states (East Malaysia) on the island of BORNEO. It is also called the Federation of Malaysia. Its capital is Kuala Lumpur. Before 1963 it was the Union of Malaya. It reorganized in 1948 as the Federation of Malaya, becoming independent from British Malaya in 1957 and becoming Malaysia in 1963 as a federation of Malaya, Sabah, Sarawak, and Singapore (which seceded in 1965). The form Malay- probably derives from the Tamil malay, mountain, with reference to its geography. (From Webster's New Geographical Dictionary, 1988, p715 & Room, Brewer's Dictionary of Names, 1992, p329)	4.91	10	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.	2.07	1	0	3',5'-cyclic purine nucleotide; guanyl ribonucleotide	Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
deoxyguanosine [no description available]	2.06	1	0	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae 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.	2.41	2	0	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
pheophytin a pheophytin a: structure given in first source; RN given refers to (3S-(3alpha(2E,7S,11S),4beta,21beta))-isomer	3.79	10	0
2',3'-cyclic gmp 2',3'-cyclic GMP: was GUANOSINE CYCLIC 2',3'-MONOPHOSPHATE see GUANOSINE CYCLIC MONOPHOSPHATE 1980-93; use CYCLIC GMP to search 1980-93. 2',3'-cyclic GMP : A 2',3'-cyclic purine nucleotide in which guanosine is used as the parent nucleoside.	2.21	1	0	2',3'-cyclic purine nucleotide	Escherichia coli metabolite
rifampin Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)	4.9	1	1	cyclic ketal; hydrazone; N-iminopiperazine; N-methylpiperazine; rifamycins; semisynthetic derivative; zwitterion	angiogenesis inhibitor; antiamoebic agent; antineoplastic agent; antitubercular agent; DNA synthesis inhibitor; EC 2.7.7.6 (RNA polymerase) inhibitor; Escherichia coli metabolite; geroprotector; leprostatic drug; neuroprotective agent; pregnane X receptor agonist; protein synthesis inhibitor
syringaldazine syringaldazine: used for detection of laccase in sporophores of wood rotting fungi; structure	3.45	7	0
allopurinol Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.	2.44	2	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
cytarabine Guanosine Diphosphate Fucose: A nucleoside diphosphate sugar formed from GDPmannose, which provides fucose for lipopolysaccharides of bacterial cell walls, and for blood group substances and other glycoproteins.	2.15	1	0	GDP-fucose
5,6,7,8-tetrahydrofolic acid 5,6,7,8-tetrahydrofolic acid: RN given refers to (DL)-isomer	1.99	1	0	tetrahydrofolic acid
amido black Amido Black: A dye used to stain proteins in electrophoretic techniques. It is used interchangeably with its acid form.. Amido Black 10B (acid form) : A bis(azo) compound that is naphthalene-2,7-disulfonic acid in which the hydrogens at positions 3, 4, 5, and 6 are replaced by (p-nitrophenyl)azo, amino, hydroxy, and phenylazo groups, respectively. A biological stain, it can be used interchangeably with its disodium salt, Amido Black 10B.	2.06	1	0
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).	2.43	2	0
methylnitronitrosoguanidine Methylnitronitrosoguanidine: A nitrosoguanidine derivative with potent mutagenic and carcinogenic properties.. N-methyl-N'-nitro-N-nitrosoguanidine : An N-nitroguanidine compound having nitroso and methyl substituents at the N'-position	2.69	3	0	nitroso compound	alkylating agent
8-hydroxy-2'-deoxyguanosine 8-Hydroxy-2'-Deoxyguanosine: Common oxidized form of deoxyguanosine in which C-8 position of guanine base has a carbonyl group.. 8-hydroxy-2'-deoxyguanosine : Guanosine substituted at the purine 8-position by a hydroxy group. It is used as a biomarker of oxidative DNA damage.	2.06	1	0	guanosines	biomarker
alizarine yellow g alizarine yellow G: binds bovine serum albumin; RN given refers to Na salt; structure given in first source	2.15	1	0
remazol black b Remazol black B: RN given refers to the tetrasodium salt. remazole black-GR : A bis(azo) compound with two aryldiazenyl moieties placed at positions 2 and 7 of a multi-substituted naphthalene.	2.98	4	0
eriochrome black t [no description available]	2.17	1	0
imidacloprid imidacloprid: systemic & contact insecticide exhibiting low mammalian toxicity; structure given in first source; it is one of the neonicotinoid insecticides, which acts as an antagonist by binding to postsynaptic nicotinic receptors in the insect central nervous system. imidacloprid : An imidazolidine that is N-nitroimidazolidin-2-imine bearing a (6-chloro-3-pyridinyl)methyl substituent at position 1.	9.3	5	0	imidacloprid; imidazolidines; monochloropyridine	environmental contaminant; genotoxin; neonicotinoid insectide; nicotinic acetylcholine receptor agonist; xenobiotic
avermectin avermectin: produced by actinomycete, Streptomyces avermitilis; structure; see also records for specific avermectins. avermectin : Any of the macrolides obtained as fermentation products from the bacterium Streptomyces avermitilis and consisting of a 16-membered macrocyclic backbone that is fused both benzofuran and spiroketal functions and contains a disaccharide substituent. They have significant anthelmintic and insecticidal properties.	2.93	3	0
cholestyramine resin Cholestyramine Resin: A strongly basic anion exchange resin whose main constituent is polystyrene trimethylbenzylammonium Cl(-) anion.	6.74	11	1
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.	3.17	4	0
concanavalin a Concanavalin A: A MANNOSE/GLUCOSE binding lectin isolated from the jack bean (Canavalia ensiformis). It is a potent mitogen used to stimulate cell proliferation in lymphocytes, primarily T-lymphocyte, cultures.	2.7	3	0
metallothionein Metallothionein: A low-molecular-weight (approx. 10 kD) protein occurring in the cytoplasm of kidney cortex and liver. It is rich in cysteinyl residues and contains no aromatic amino acids. Metallothionein shows high affinity for bivalent heavy metals.	2.73	3	0
dinitrobenzenes Dinitrobenzenes: Benzene derivatives which are substituted with two nitro groups in the ortho, meta or para positions.	2.69	3	0
phosphorus radioisotopes Phosphorus Radioisotopes: Unstable isotopes of phosphorus that decay or disintegrate emitting radiation. P atoms with atomic weights 28-34 except 31 are radioactive phosphorus isotopes.	2.01	1	0
araban araban: contains arabinose & galactose	4.8	5	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.	4.04	14	0

Condition	Relationship Strength	Studies	Trials
Disease Resistance The capacity of an organism to defend itself against pathological processes or the agents of those processes. This most often involves innate immunity whereby the organism responds to pathogens in a generic way. The term disease resistance is used most frequently when referring to plants.	7.36	87	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	6.12	11	1
Colitis Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.	6.17	7	1
Infections, Coronavirus [description not available]	2.41	1	0
Coronavirus Infections Virus diseases caused by the CORONAVIRUS genus. Some specifics include transmissible enteritis of turkeys (ENTERITIS, TRANSMISSIBLE, OF TURKEYS); FELINE INFECTIOUS PERITONITIS; and transmissible gastroenteritis of swine (GASTROENTERITIS, TRANSMISSIBLE, OF SWINE).	2.41	1	0
Alloxan Diabetes [description not available]	2.79	3	0
Hypergonadotropic Hypogonadism [description not available]	2.41	1	0
Insulin Sensitivity [description not available]	2.41	1	0
Sex Disorders [description not available]	2.41	1	0
Hypogonadism Condition resulting from deficient gonadal functions, such as GAMETOGENESIS and the production of GONADAL STEROID HORMONES. It is characterized by delay in GROWTH, germ cell maturation, and development of secondary sex characteristics. Hypogonadism can be due to a deficiency of GONADOTROPINS (hypogonadotropic hypogonadism) or due to primary gonadal failure (hypergonadotropic hypogonadism).	2.41	1	0
Insulin Resistance Diminished effectiveness of INSULIN in lowering blood sugar levels: requiring the use of 200 units or more of insulin per day to prevent HYPERGLYCEMIA or KETOSIS.	2.41	1	0
Sexual Dysfunction, Physiological Physiological disturbances in normal sexual performance in either the male or the female.	2.41	1	0
DDPAC [description not available]	2.41	1	0
Frontotemporal Dementia The most common clinical form of FRONTOTEMPORAL LOBAR DEGENERATION, this dementia presents with personality and behavioral changes often associated with disinhibition, apathy, and lack of insight.	2.41	1	0
Dermatitis Any inflammation of the skin.	7.83	3	0
Electrolytes Substances that dissociate into two or more ions, to some extent, in water. Solutions of electrolytes thus conduct an electric current and can be decomposed by it (ELECTROLYSIS). (Grant & Hackh's Chemical Dictionary, 5th ed)	5.3	18	0
Weight Reduction [description not available]	2.41	1	0
Weight Loss Decrease in existing BODY WEIGHT.	2.41	1	0
Familial Combined Hyperlipidemia [description not available]	2.41	1	0
Hyperlipidemia, Familial Combined A type of familial lipid metabolism disorder characterized by a variable pattern of elevated plasma CHOLESTEROL and/or TRIGLYCERIDES. Multiple genes on different chromosomes may be involved, such as the major late transcription factor (UPSTREAM STIMULATORY FACTORS) on CHROMOSOME 1.	2.41	1	0
Cancer of the Thyroid [description not available]	2.9	2	0
Thyroid Neoplasms Tumors or cancer of the THYROID GLAND.	2.9	2	0
Dehydration The condition that results from excessive loss of water from a living organism.	4.89	11	0
Triploid [description not available]	3.22	5	0
Extravascular Hemolysis [description not available]	3.32	5	0
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	3.32	5	0
Carcinogenesis The origin, production or development of cancer through genotypic and phenotypic changes which upset the normal balance between cell proliferation and cell death. Carcinogenesis generally requires a constellation of steps, which may occur quickly or over a period of many years.	7.41	1	0
Weight Gain Increase in BODY WEIGHT over existing weight.	3.9	12	0
Arthritis, Degenerative [description not available]	2.72	2	0
Osteoarthritis A progressive, degenerative joint disease, the most common form of arthritis, especially in older persons. The disease is thought to result not from the aging process but from biochemical changes and biomechanical stresses affecting articular cartilage. In the foreign literature it is often called osteoarthrosis deformans.	2.72	2	0
2019 Novel Coronavirus Disease [description not available]	5.49	6	0
Autosomal Dominant Striatonigral Degeneration [description not available]	2.41	1	0
Machado-Joseph Disease A dominantly-inherited ATAXIA first described in people of Azorean and Portuguese descent, and subsequently identified in Brazil, Japan, China, and Australia. This disorder is classified as one of the SPINOCEREBELLAR ATAXIAS (Type 3) and has been associated with a mutation of the MJD1 gene on chromosome 14. Clinical features include progressive ataxia, DYSARTHRIA, postural instability, nystagmus, eyelid retraction, and facial FASCICULATIONS. DYSTONIA is prominent in younger patients (referred to as Type I Machado-Joseph Disease). Type II features ataxia and ocular signs; Type III features MUSCULAR ATROPHY and a sensorimotor neuropathy; and Type IV features extrapyramidal signs combined with a sensorimotor neuropathy. (From Clin Neurosci 1995;3(1):17-22; Ann Neurol 1998 Mar;43(3):288-96)	2.41	1	0
Burns Injuries to tissues caused by contact with heat, steam, chemicals (BURNS, CHEMICAL), electricity (BURNS, ELECTRIC), or the like.	2.41	1	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	6.15	32	1
Alcoholic Liver Diseases [description not available]	3.52	1	0
Liver Diseases, Alcoholic Liver diseases associated with ALCOHOLISM. It usually refers to the coexistence of two or more subentities, i.e., ALCOHOLIC FATTY LIVER; ALCOHOLIC HEPATITIS; and ALCOHOLIC CIRRHOSIS.	3.52	1	0
Innate Inflammatory Response [description not available]	4.66	9	0
Bowel Diseases, Inflammatory [description not available]	3.65	5	0
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	4.66	9	0
Inflammatory Bowel Diseases Chronic, non-specific inflammation of the GASTROINTESTINAL TRACT. Etiology may be genetic or environmental. This term includes CROHN DISEASE and ULCERATIVE COLITIS.	3.65	5	0
Bile Duct Obstruction [description not available]	4.07	3	1
Cholestasis Impairment of bile flow due to obstruction in small bile ducts (INTRAHEPATIC CHOLESTASIS) or obstruction in large bile ducts (EXTRAHEPATIC CHOLESTASIS).	4.07	3	1
Osteogenic Sarcoma [description not available]	2.41	1	0
Osteosarcoma A sarcoma originating in bone-forming cells, affecting the ends of long bones. It is the most common and most malignant of sarcomas of the bones, and occurs chiefly among 10- to 25-year-old youths. (From Stedman, 25th ed)	7.41	1	0
Airflow Obstruction, Chronic [description not available]	4.72	1	1
ER-Negative PR-Negative HER2-Negative Breast Cancer [description not available]	4.72	1	1
Disbacteriosis [description not available]	4.72	1	1
Carcinoma, Squamous Cell of Head and Neck [description not available]	4.72	1	1
Acinetobacter Infections Infections with bacteria of the genus ACINETOBACTER.	4.72	1	1
Acute Confusional Senile Dementia [description not available]	4.72	1	1
ADDH [description not available]	4.72	1	1
Bleb [description not available]	4.72	1	1
Breast Cancer [description not available]	8.33	12	1
Clostridioides difficile Infection [description not available]	4.72	1	1
Diabetes Mellitus, Adult-Onset [description not available]	5.49	2	1
Lassitude [description not available]	4.72	1	1
Graft-Versus-Host Disease [description not available]	4.72	1	1
Cancer of Head [description not available]	4.72	1	1
Hepatocellular Carcinoma [description not available]	5.45	5	1
Blood Pressure, High [description not available]	4.72	1	1
Infections, Klebsiella [description not available]	4.72	1	1
Cancer of Liver [description not available]	5.28	4	1
Eperythrozoonosis [description not available]	4.72	1	1
Angiogenesis, Pathologic [description not available]	4.75	2	1
Paratyphoid Fever A prolonged febrile illness commonly caused by several Paratyphi serotypes of SALMONELLA ENTERICA. It is similar to TYPHOID FEVER but less severe.	4.72	1	1
Symptom Cluster [description not available]	4.72	1	1
Low Back Ache [description not available]	4.72	1	1
Squamous Cell Carcinoma of Head and Neck The most common type of head and neck carcinoma that originates from cells on the surface of the NASAL CAVITY; MOUTH; PARANASAL SINUSES, SALIVARY GLANDS, and LARYNX. Mutations in TNFRSF10B, PTEN, and ING1 genes are associated with this cancer.	4.72	1	1
Alcohol Drinking Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.	4.72	1	1
Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)	4.72	1	1
Anorexia The lack or loss of APPETITE accompanied by an aversion to food and the inability to eat. It is the defining characteristic of the disorder ANOREXIA NERVOSA.	4.72	1	1
Anxiety Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.	4.72	1	1
Asthenia Clinical sign or symptom manifested as debility, or lack or loss of strength and energy.	4.72	1	1
Attention Deficit Disorder with Hyperactivity A behavior disorder originating in childhood in which the essential features are signs of developmentally inappropriate inattention, impulsivity, and hyperactivity. Although most individuals have symptoms of both inattention and hyperactivity-impulsivity, one or the other pattern may be predominant. The disorder is more frequent in males than females. Onset is in childhood. Symptoms often attenuate during late adolescence although a minority experience the full complement of symptoms into mid-adulthood. (From DSM-V)	4.72	1	1
Breast Neoplasms Tumors or cancer of the human BREAST.	8.33	12	1
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	9.61	8	1
Clostridium Infections Infections with bacteria of the genus CLOSTRIDIUM and closely related CLOSTRIDIOIDES species.	4.72	1	1
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	4.72	1	1
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	5.49	2	1
Diabetic Retinopathy Disease of the RETINA as a complication of DIABETES MELLITUS. It is characterized by the progressive microvascular complications, such as ANEURYSM, interretinal EDEMA, and intraocular PATHOLOGIC NEOVASCULARIZATION.	4.72	1	1
Diarrhea An increased liquidity or decreased consistency of FECES, such as running stool. Fecal consistency is related to the ratio of water-holding capacity of insoluble solids to total water, rather than the amount of water present. Diarrhea is not hyperdefecation or increased fecal weight.	11.44	7	1
Fatigue The state of weariness following a period of exertion, mental or physical, characterized by a decreased capacity for work and reduced efficiency to respond to stimuli.	4.72	1	1
Graft vs Host Disease The clinical entity characterized by anorexia, diarrhea, loss of hair, leukopenia, thrombocytopenia, growth retardation, and eventual death brought about by the GRAFT VS HOST REACTION.	4.72	1	1
Head and Neck Neoplasms Soft tissue tumors or cancer arising from the mucosal surfaces of the LIP; oral cavity; PHARYNX; LARYNX; and cervical esophagus. Other sites included are the NOSE and PARANASAL SINUSES; SALIVARY GLANDS; THYROID GLAND and PARATHYROID GLANDS; and MELANOMA and non-melanoma skin cancers of the head and neck. (from Holland et al., Cancer Medicine, 4th ed, p1651)	4.72	1	1
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	5.45	5	1
Hypertension Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.	4.72	1	1
Klebsiella Infections Infections with bacteria of the genus KLEBSIELLA.	4.72	1	1
Liver Neoplasms Tumors or cancer of the LIVER.	5.28	4	1
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	9.49	14	1
Syndrome A characteristic symptom complex.	4.72	1	1
Urinary Tract Infections Inflammatory responses of the epithelium of the URINARY TRACT to microbial invasions. They are often bacterial infections with associated BACTERIURIA and PYURIA.	4.72	1	1
Low Back Pain Acute or chronic pain in the lumbar or sacral regions, which may be associated with musculo-ligamentous SPRAINS AND STRAINS; INTERVERTEBRAL DISK DISPLACEMENT; and other conditions.	4.72	1	1
Pulmonary Disease, Chronic Obstructive A disease of chronic diffuse irreversible airflow obstruction. Subcategories of COPD include CHRONIC BRONCHITIS and PULMONARY EMPHYSEMA.	4.72	1	1
Suicidal Ideation A risk factor for suicide attempts and completions, it is the most common of all suicidal behavior, but only a minority of ideators engage in overt self-harm.	4.72	1	1
Triple Negative Breast Neoplasms Breast neoplasms that do not express ESTROGEN RECEPTORS; PROGESTERONE RECEPTORS; and do not overexpress the NEU RECEPTOR/HER-2 PROTO-ONCOGENE PROTEIN.	4.72	1	1
Fatty Liver, Nonalcoholic [description not available]	2.41	1	0
Non-alcoholic Fatty Liver Disease Fatty liver finding without excessive ALCOHOL CONSUMPTION.	2.41	1	0
Polyploid [description not available]	3.41	6	0
Nanism [description not available]	2.41	1	0
Dwarfism A genetic or pathological condition that is characterized by short stature and undersize. Abnormal skeletal growth usually results in an adult who is significantly below the average height.	2.41	1	0
American Trypanosomiasis [description not available]	2.6	1	0
Chagas Disease Infection with the protozoan parasite TRYPANOSOMA CRUZI, a form of TRYPANOSOMIASIS endemic in Central and South America. It is named after the Brazilian physician Carlos Chagas, who discovered the parasite. Infection by the parasite (positive serologic result only) is distinguished from the clinical manifestations that develop years later, such as destruction of PARASYMPATHETIC GANGLIA; CHAGAS CARDIOMYOPATHY; and dysfunction of the ESOPHAGUS or COLON.	2.6	1	0
ALS - Amyotrophic Lateral Sclerosis [description not available]	3.01	2	0
Amyotrophic Lateral Sclerosis A degenerative disorder affecting upper MOTOR NEURONS in the brain and lower motor neurons in the brain stem and SPINAL CORD. Disease onset is usually after the age of 50 and the process is usually fatal within 3 to 6 years. Clinical manifestations include progressive weakness, atrophy, FASCICULATION, hyperreflexia, DYSARTHRIA, dysphagia, and eventual paralysis of respiratory function. Pathologic features include the replacement of motor neurons with fibrous ASTROCYTES and atrophy of anterior SPINAL NERVE ROOTS and corticospinal tracts. (From Adams et al., Principles of Neurology, 6th ed, pp1089-94)	3.01	2	0
Infections, Staphylococcal [description not available]	2.6	1	0
Staphylococcal Infections Infections with bacteria of the genus STAPHYLOCOCCUS.	2.6	1	0
Benign Neoplasms [description not available]	8.53	11	0
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	8.53	11	0
Tetraploid [description not available]	2.6	1	0
Anoxemia [description not available]	2.69	2	0
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	2.69	2	0
Chromosomal Translocation [description not available]	2.57	2	0
Cancer of Colon [description not available]	7.11	15	0
Colonic Neoplasms Tumors or cancer of the COLON.	7.11	15	0
Alopecia Cicatrisata [description not available]	2.6	1	0
Alopecia Absence of hair from areas where it is normally present.	7.6	1	0
Ischemia A hypoperfusion of the BLOOD through an organ or tissue caused by a PATHOLOGIC CONSTRICTION or obstruction of its BLOOD VESSELS, or an absence of BLOOD CIRCULATION.	2.4	2	0
Bacterial Disease [description not available]	4.32	4	1
Bacterial Infections Infections by bacteria, general or unspecified.	4.32	4	1
Gastric Ulcer [description not available]	4.61	6	1
Stomach Ulcer Ulceration of the GASTRIC MUCOSA due to contact with GASTRIC JUICE. It is often associated with HELICOBACTER PYLORI infection or consumption of nonsteroidal anti-inflammatory drugs (NSAIDS).	4.61	6	1
Herpes Simplex Virus Infection [description not available]	2.49	2	0
HIV Coinfection [description not available]	3.94	4	0
Herpes Simplex A group of acute infections caused by herpes simplex virus type 1 or type 2 that is characterized by the development of one or more small fluid-filled vesicles with a raised erythematous base on the skin or mucous membrane. It occurs as a primary infection or recurs due to a reactivation of a latent infection. (Dorland, 27th ed.)	2.49	2	0
HIV Human immunodeficiency virus. A non-taxonomic and historical term referring to any of two species, specifically HIV-1 and/or HIV-2. Prior to 1986, this was called human T-lymphotropic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV). From 1986-1990, it was an official species called HIV. Since 1991, HIV was no longer considered an official species name; the two species were designated HIV-1 and HIV-2.	8.83	4	0
HIV Infections Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).	3.94	4	0
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	4.98	37	0
Carcinoma, Ehrlich Tumor A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.	2.59	2	0
Cancer of Pancreas [description not available]	2.25	1	0
Pancreatic Neoplasms Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).	2.25	1	0
Cirrhosis [description not available]	2.25	1	0
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	7.25	1	0
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	2.51	2	0
Disseminated Fusariosis [description not available]	2.53	2	0
Fusariosis OPPORTUNISTIC INFECTIONS with the soil fungus FUSARIUM. Typically the infection is limited to the nail plate (ONYCHOMYCOSIS). The infection can however become systemic especially in an IMMUNOCOMPROMISED HOST (e.g., NEUTROPENIA) and results in cutaneous and subcutaneous lesions, fever, KERATITIS, and pulmonary infections.	2.53	2	0
Peripheral Nerve Injury [description not available]	2.25	1	0
Peripheral Nerve Injuries Injuries to the PERIPHERAL NERVES.	2.25	1	0
Genetic Predisposition [description not available]	3.17	1	0
Overweight A status with BODY WEIGHT that is above certain standards. In the scale of BODY MASS INDEX, overweight is defined as having a BMI of 25.0-29.9 kg/m2. Overweight may or may not be due to increases in body fat (ADIPOSE TISSUE), hence overweight does not equal over fat.	3.17	1	0
Abdominal Obesity [description not available]	3.17	1	0
Cholera Infantum [description not available]	4.45	5	0
Malignant Melanoma [description not available]	3.55	2	0
Addiction, Opioid [description not available]	3.17	1	0
Cancer of Endometrium [description not available]	4.52	5	0
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	8.55	2	0
Opioid-Related Disorders Disorders related to or resulting from abuse or misuse of OPIOIDS.	3.17	1	0
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	7.26	11	0
Endometrial Neoplasms Tumors or cancer of ENDOMETRIUM, the mucous lining of the UTERUS. These neoplasms can be benign or malignant. Their classification and grading are based on the various cell types and the percent of undifferentiated cells.	4.52	5	0
Cancer of Cervix [description not available]	2.46	2	0
Uterine Cervical Neoplasms Tumors or cancer of the UTERINE CERVIX.	2.46	2	0
Gouty Arthritis [description not available]	2.31	1	0
Arthritis, Gouty Arthritis, especially of the great toe, as a result of gout. Acute gouty arthritis often is precipitated by trauma, infection, surgery, etc. The initial attacks are usually monoarticular but later attacks are often polyarticular. Acute and chronic gouty arthritis are associated with accumulation of MONOSODIUM URATE in and around affected joints.	2.31	1	0
Hyperuricemia Excessive URIC ACID or urate in blood as defined by its solubility in plasma at 37 degrees C; greater than 0.42mmol per liter (7.0mg/dL) in men or 0.36mmol per liter (6.0mg/dL) in women. This condition is caused by overproduction of uric acid or impaired renal clearance. Hyperuricemia can be acquired, drug-induced or genetically determined (LESCH-NYHAN SYNDROME). It is associated with HYPERTENSION and GOUT.	2.31	1	0
Osteolysis Dissolution of bone that particularly involves the removal or loss of calcium.	2.31	1	0
Apnea, Obstructive Sleep [description not available]	2.31	1	0
Apnea, Central [description not available]	2.31	1	0
Corneal Diseases Diseases of the cornea.	2.31	1	0
Sleep Apnea, Obstructive A disorder characterized by recurrent apneas during sleep despite persistent respiratory efforts. It is due to upper airway obstruction. The respiratory pauses may induce HYPERCAPNIA or HYPOXIA. Cardiac arrhythmias and elevation of systemic and pulmonary arterial pressures may occur. Frequent partial arousals occur throughout sleep, resulting in relative SLEEP DEPRIVATION and daytime tiredness. Associated conditions include OBESITY; ACROMEGALY; MYXEDEMA; micrognathia; MYOTONIC DYSTROPHY; adenotonsilar dystrophy; and NEUROMUSCULAR DISEASES. (From Adams et al., Principles of Neurology, 6th ed, p395)	2.31	1	0
Sleep Apnea, Central A condition associated with multiple episodes of sleep apnea which are distinguished from obstructive sleep apnea (SLEEP APNEA, OBSTRUCTIVE) by the complete cessation of efforts to breathe. This disorder is associated with dysfunction of central nervous system centers that regulate respiration.	2.31	1	0
Allergy, Drug [description not available]	2.31	1	0
Drug Hypersensitivity Immunologically mediated adverse reactions to medicinal substances used legally or illegally.	2.31	1	0
Keratitis Inflammation of the cornea.	2.31	1	0
Infectious Diseases [description not available]	3.82	2	0
Communicable Diseases An illness caused by an infectious agent or its toxins that occurs through the direct or indirect transmission of the infectious agent or its products from an infected individual or via an animal, vector or the inanimate environment to a susceptible animal or human host.	3.82	2	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	3.7	3	0
Diathesis [description not available]	2.77	3	0
Candida Infection [description not available]	2.17	1	0
Candidiasis Infection with a fungus of the genus CANDIDA. It is usually a superficial infection of the moist areas of the body and is generally caused by CANDIDA ALBICANS. (Dorland, 27th ed)	2.17	1	0
Acute Radiation Syndrome A condition caused by a brief whole body exposure to more than one sievert dose equivalent of radiation. Acute radiation syndrome is initially characterized by ANOREXIA; NAUSEA; VOMITING; but can progress to hematological, gastrointestinal, neurological, pulmonary, and other major organ dysfunction.	2.17	1	0
Age-Related Osteoporosis [description not available]	2.17	1	0
Osteoporosis Reduction of bone mass without alteration in the composition of bone, leading to fractures. Primary osteoporosis can be of two major types: postmenopausal osteoporosis (OSTEOPOROSIS, POSTMENOPAUSAL) and age-related or senile osteoporosis.	2.17	1	0
Local Neoplasm Recurrence [description not available]	2.17	1	0
Asthma, Bronchial [description not available]	2.43	2	0
Asthma A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL).	2.43	2	0
Elevated Cholesterol [description not available]	2.4	2	0
Hypercholesterolemia A condition with abnormally high levels of CHOLESTEROL in the blood. It is defined as a cholesterol value exceeding the 95th percentile for the population.	2.4	2	0
Bovine Diseases [description not available]	2.21	1	0
Flatus [description not available]	2.21	1	0
Flatulence Production or presence of gas in the gastrointestinal tract which may be expelled through the anus.	2.21	1	0
Besnoitiasis [description not available]	2.21	1	0
Poultry Diseases Diseases of birds which are raised as a source of meat or eggs for human consumption and are usually found in barnyards, hatcheries, etc. The concept is differentiated from BIRD DISEASES which is for diseases of birds not considered poultry and usually found in zoos, parks, and the wild.	4.31	4	1
Chromosome-Defective Micronuclei [description not available]	2.08	1	0
Histiocytosis General term for the abnormal appearance of histiocytes in the blood. Based on the pathological features of the cells involved rather than on clinical findings, the histiocytic diseases are subdivided into three groups: HISTIOCYTOSIS, LANGERHANS CELL; HISTIOCYTOSIS, NON-LANGERHANS-CELL; and HISTIOCYTIC DISORDERS, MALIGNANT.	2.08	1	0
Bone Loss, Osteoclastic [description not available]	2.1	1	0
Metastase [description not available]	2.1	1	0
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	2.1	1	0
Carcinoma, Colloid [description not available]	2.1	1	0
Cancer of Ovary [description not available]	3.34	2	0
Adenocarcinoma, Mucinous An adenocarcinoma producing mucin in significant amounts. (From Dorland, 27th ed)	2.1	1	0
Ovarian Neoplasms Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.	3.34	2	0
Genome Instability [description not available]	2.1	1	0
Carcinoma, Epidermoid [description not available]	3.63	3	0
Cancer of Mouth [description not available]	3.6	3	0
Carcinoma, Squamous Cell A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)	3.63	3	0
Gingivitis Inflammation of gum tissue (GINGIVA) without loss of connective tissue.	3.01	1	0
Mouth Neoplasms Tumors or cancer of the MOUTH.	3.6	3	0
Adenoma, Basal Cell [description not available]	2.11	1	0
Colorectal Cancer [description not available]	4.1	3	0
Adenoma A benign epithelial tumor with a glandular organization.	2.11	1	0
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	4.1	3	0
Chronic Lung Injury [description not available]	2.1	1	0
Endotoxin Shock [description not available]	2.1	1	0
Shock, Septic Sepsis associated with HYPOTENSION or hypoperfusion despite adequate fluid resuscitation. Perfusion abnormalities may include but are not limited to LACTIC ACIDOSIS; OLIGURIA; or acute alteration in mental status.	2.1	1	0
Genital Herpes [description not available]	2.47	2	0
Herpes Genitalis Infection of the genitals (GENITALIA) with HERPES SIMPLEX VIRUS in either the males or the females.	2.47	2	0
Disease Exacerbation [description not available]	2.13	1	0
Bleeding [description not available]	2.13	1	0
Blood Clot [description not available]	2.53	2	0
Hemorrhage Bleeding or escape of blood from a vessel.	2.13	1	0
Thrombosis Formation and development of a thrombus or blood clot in the blood vessel.	2.53	2	0
Malnourishment [description not available]	3.06	1	0
Malnutrition An imbalanced nutritional status resulting from insufficient intake of nutrients to meet normal physiological requirement.	3.06	1	0
Injuries Used with anatomic headings, animals, and sports for wounds and injuries. Excludes cell damage, for which pathology is used.	2.13	1	0
Wounds and Injuries Damage inflicted on the body as the direct or indirect result of an external force, with or without disruption of structural continuity.	2.13	1	0
Abnormalities, Autosome [description not available]	2.74	3	0
Experimental Neoplasms [description not available]	4.27	7	0
Uremia A clinical syndrome associated with the retention of renal waste products or uremic toxins in the blood. It is usually the result of RENAL INSUFFICIENCY. Most uremic toxins are end products of protein or nitrogen CATABOLISM, such as UREA or CREATININE. Severe uremia can lead to multiple organ dysfunctions with a constellation of symptoms.	2.44	2	0
Swine Diseases Diseases of domestic swine and of the wild boar of the genus Sus.	3.81	2	1
Starvation Lengthy and continuous deprivation of food. (Stedman, 25th ed)	2.05	1	0
Diabetes Mellitus A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.	8.5	10	0
Menopause The last menstrual period. Permanent cessation of menses (MENSTRUATION) is usually defined after 6 to 12 months of AMENORRHEA in a woman over 45 years of age. In the United States, menopause generally occurs in women between 48 and 55 years of age.	5.55	6	1
Diseases, Occupational [description not available]	3.31	2	0
Airway Hyper-Responsiveness [description not available]	2.05	1	0
Viral Diseases [description not available]	2.37	2	0
Cytomegalovirus A genus of the family HERPESVIRIDAE, subfamily BETAHERPESVIRINAE, infecting the salivary glands, liver, spleen, lungs, eyes, and other organs, in which they produce characteristically enlarged cells with intranuclear inclusions. Infection with Cytomegalovirus is also seen as an opportunistic infection in AIDS.	2.41	2	0
Virus Diseases A general term for diseases caused by viruses.	2.37	2	0
Foot Diseases Anatomical and functional disorders affecting the foot.	2.06	1	0
Emphysema A pathological accumulation of air in tissues or organs.	7.08	1	0
Carcinoma, Anaplastic [description not available]	2.39	2	0
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	2.39	2	0
Fungal Diseases [description not available]	3.3	2	0
Mycoses Diseases caused by FUNGI.	3.3	2	0
Adenocarcinoma, Basal Cell [description not available]	2.89	4	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	2.89	4	0
Gastroduodenal Ulcer [description not available]	2.63	3	0
Peptic Ulcer Ulcer that occurs in the regions of the GASTROINTESTINAL TRACT which come into contact with GASTRIC JUICE containing PEPSIN and GASTRIC ACID. It occurs when there are defects in the MUCOSA barrier. The common forms of peptic ulcers are associated with HELICOBACTER PYLORI and the consumption of nonsteroidal anti-inflammatory drugs (NSAIDS).	2.63	3	0
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	2.9	4	0
Acute Lymphoid Leukemia [description not available]	2.02	1	0
Precursor Cell Lymphoblastic Leukemia-Lymphoma A neoplasm characterized by abnormalities of the lymphoid cell precursors leading to excessive lymphoblasts in the marrow and other organs. It is the most common cancer in children and accounts for the vast majority of all childhood leukemias.	2.02	1	0
Delayed Hypersensitivity [description not available]	2.02	1	0
Atopic Hypersensitivity [description not available]	2.02	1	0
Gallstone Disease [description not available]	6.84	11	1
Cholelithiasis Presence or formation of GALLSTONES in the BILIARY TRACT, usually in the gallbladder (CHOLECYSTOLITHIASIS) or the common bile duct (CHOLEDOCHOLITHIASIS).	6.84	11	1
Arthritides, Bacterial [description not available]	2.02	1	0
Anasarca [description not available]	2.02	1	0
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	2.02	1	0
Retinal Diseases Diseases involving the RETINA.	2.03	1	0
Carbon Tetrachloride Poisoning Poisoning that results from ingestion, injection, inhalation, or skin absorption of CARBON TETRACHLORIDE.	2.03	1	0
Cirrhoses, Experimental Liver [description not available]	2.03	1	0
Ascites Accumulation or retention of free fluid within the peritoneal cavity.	2.03	1	0
Hot Flashes A sudden, temporary sensation of heat predominantly experienced by some women during MENOPAUSE. (Random House Unabridged Dictionary, 2d ed)	3.42	1	1
Experimental Radiation Injuries [description not available]	2.03	1	0
Tooth Diseases Diseases involving the TEETH.	2.04	1	0
Anemia, Hypochromic Anemia characterized by a decrease in the ratio of the weight of hemoglobin to the volume of the erythrocyte, i.e., the mean corpuscular hemoglobin concentration is less than normal. The individual cells contain less hemoglobin than they could have under optimal conditions. Hypochromic anemia may be caused by iron deficiency from a low iron intake, diminished iron absorption, or excessive iron loss. It can also be caused by infections or other diseases, therapeutic drugs, lead poisoning, and other conditions. (Stedman, 25th ed; from Miale, Laboratory Medicine: Hematology, 6th ed, p393)	2.35	2	0
Colonic Inertia Symptom characterized by the passage of stool once a week or less.	4.26	4	0
Arteriosclerosis Thickening and loss of elasticity of the walls of ARTERIES of all sizes. There are many forms classified by the types of lesions and arteries involved, such as ATHEROSCLEROSIS with fatty lesions in the ARTERIAL INTIMA of medium and large muscular arteries.	4.35	3	0
Constipation Infrequent or difficult evacuation of FECES. These symptoms are associated with a variety of causes, including low DIETARY FIBER intake, emotional or nervous disturbances, systemic and structural disorders, drug-induced aggravation, and infections.	4.26	4	0
Diverticulitis Inflammation of a DIVERTICULUM or diverticula.	2.87	1	0
Cancer of Intestines [description not available]	2.65	3	0
Intestinal Neoplasms Tumors or cancer of the INTESTINES.	2.65	3	0
Bezoars Concretions of swallowed hair, fruit or vegetable fibers, or similar substances found in the alimentary canal.	1.95	1	0
Eczema, Atopic [description not available]	1.95	1	0
Contact Dermatitis [description not available]	1.95	1	0
Dermatitis, Atopic A chronic inflammatory genetically determined disease of the skin marked by increased ability to form reagin (IgE), with increased susceptibility to allergic rhinitis and asthma, and hereditary disposition to a lowered threshold for pruritus. It is manifested by lichenification, excoriation, and crusting, mainly on the flexural surfaces of the elbow and knee. In infants it is known as infantile eczema.	1.95	1	0
Dermatitis, Contact A type of acute or chronic skin reaction in which sensitivity is manifested by reactivity to materials or substances coming in contact with the skin. It may involve allergic or non-allergic mechanisms.	1.95	1	0
Hyperlipemia [description not available]	5.15	6	0
Hyperlipidemias Conditions with excess LIPIDS in the blood.	5.15	6	0
Cancer of Nasopharynx [description not available]	2.37	2	0
Nasopharyngeal Neoplasms Tumors or cancer of the NASOPHARYNX.	2.37	2	0
Chronic Illness [description not available]	2.67	3	0
Experimental Lung Inflammation Inflammation of any part, segment or lobe, of the lung parenchyma.	1.98	1	0
Bronchitis Inflammation of the large airways in the lung including any part of the BRONCHI, from the PRIMARY BRONCHI to the TERTIARY BRONCHI.	1.98	1	0
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	2.67	3	0
Pneumonia Infection of the lung often accompanied by inflammation.	1.98	1	0
Infections, Respiratory [description not available]	1.98	1	0
Respiratory Tract Infections Invasion of the host RESPIRATORY SYSTEM by microorganisms, usually leading to pathological processes or diseases.	1.98	1	0
Thrombopenia [description not available]	1.98	1	0
Thrombocytopenia A subnormal level of BLOOD PLATELETS.	1.98	1	0
Leukemia P388 An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.	2.38	2	0
Cancer of Prostate [description not available]	2.9	1	0
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	2.9	1	0
Altitude Hypoxia Low ambient oxygen tension associated with ALTITUDE.	1.98	1	0
Brain Swelling [description not available]	1.98	1	0
Petechiae Pinhead size (3 mm) skin discolorization due to hemorrhage.	1.98	1	0
Hemorrhage, Retinal [description not available]	1.98	1	0
Altitude Sickness Multiple symptoms associated with reduced oxygen at high ALTITUDE.	1.98	1	0
Brain Edema Increased intracellular or extracellular fluid in brain tissue. Cytotoxic brain edema (swelling due to increased intracellular fluid) is indicative of a disturbance in cell metabolism, and is commonly associated with hypoxic or ischemic injuries (see HYPOXIA, BRAIN). An increase in extracellular fluid may be caused by increased brain capillary permeability (vasogenic edema), an osmotic gradient, local blockages in interstitial fluid pathways, or by obstruction of CSF flow (e.g., obstructive HYDROCEPHALUS). (From Childs Nerv Syst 1992 Sep; 8(6):301-6)	1.98	1	0
Purpura Purplish or brownish red discoloration, easily visible through the epidermis, caused by hemorrhage into the tissues. When the size of the discolorization is	1.98	1	0
Curling Ulcer Acute stress DUODENAL ULCER, usually observed in patients with extensive third-degree burns.	1.99	1	0
Infections, Helicobacter [description not available]	1.99	1	0
Cronobacter Infections [description not available]	1.99	1	0
Duodenal Ulcer A PEPTIC ULCER located in the DUODENUM.	1.99	1	0
Enterobacteriaceae Infections Infections with bacteria of the family ENTEROBACTERIACEAE.	1.99	1	0
Intestinal Diseases Pathological processes in any segment of the INTESTINE from DUODENUM to RECTUM.	2.37	2	0
Helicobacter Infections Infections with organisms of the genus HELICOBACTER, particularly, in humans, HELICOBACTER PYLORI. The clinical manifestations are focused in the stomach, usually the gastric mucosa and antrum, and the upper duodenum. This infection plays a major role in the pathogenesis of type B gastritis and peptic ulcer disease.	1.99	1	0
Chronic Kidney Failure [description not available]	1.99	1	0
Kidney Failure, Chronic The end-stage of CHRONIC RENAL INSUFFICIENCY. It is characterized by the severe irreversible kidney damage (as measured by the level of PROTEINURIA) and the reduction in GLOMERULAR FILTRATION RATE to less than 15 ml per min (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002). These patients generally require HEMODIALYSIS or KIDNEY TRANSPLANTATION.	1.99	1	0
Cell Transformation, Neoplastic Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.	2.67	3	0
Cell Transformation, Viral An inheritable change in cells manifested by changes in cell division and growth and alterations in cell surface properties. It is induced by infection with a transforming virus.	1.99	1	0
Digestive System Disorders [description not available]	3.77	2	0
Digestive System Diseases Diseases in any part of the GASTROINTESTINAL TRACT or the accessory organs (LIVER; BILIARY TRACT; PANCREAS).	3.77	2	0
Complications of Diabetes Mellitus [description not available]	1.99	1	0
Infection, Postoperative Wound [description not available]	1.99	1	0
Leukemia L 1210 [description not available]	1.99	1	0
Experimental Mammary Neoplasms [description not available]	1.99	1	0
Biliary Tract Diseases Diseases in any part of the BILIARY TRACT including the BILE DUCTS and the GALLBLADDER.	3.38	1	1
Intestinal Diseases, Parasitic Infections of the INTESTINES with PARASITES, commonly involving PARASITIC WORMS. Infections with roundworms (NEMATODE INFECTIONS) and tapeworms (CESTODE INFECTIONS) are also known as HELMINTHIASIS.	2	1	0
Oesophagostomiasis Infection of the intestinal tract with worms of the genus OESOPHAGOSTOMUM. This condition occurs mainly in animals other than man.	2	1	0
Bladder Cancer [description not available]	2.39	2	0
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	2.39	2	0
Ache [description not available]	2	1	0
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	2	1	0
Recrudescence [description not available]	2	1	0
Diffuse Mixed Small and Large Cell Lymphoma [description not available]	2	1	0
Lymphoma, Non-Hodgkin Any of a group of malignant tumors of lymphoid tissue that differ from HODGKIN DISEASE, being more heterogeneous with respect to malignant cell lineage, clinical course, prognosis, and therapy. The only common feature among these tumors is the absence of giant REED-STERNBERG CELLS, a characteristic of Hodgkin's disease.	2	1	0
Carcinoma, Lewis Lung A carcinoma discovered by Dr. Margaret R. Lewis of the Wistar Institute in 1951. This tumor originated spontaneously as a carcinoma of the lung of a C57BL mouse. The tumor does not appear to be grossly hemorrhagic and the majority of the tumor tissue is a semifirm homogeneous mass. (From Cancer Chemother Rep 2 1972 Nov;(3)1:325) It is also called 3LL and LLC and is used as a transplantable malignancy.	2	1	0
Lymph Node Metastasis [description not available]	2	1	0
B16 Melanoma [description not available]	2	1	0
Coronary Heart Disease [description not available]	6.39	7	0
Coronary Disease An imbalance between myocardial functional requirements and the capacity of the CORONARY VESSELS to supply sufficient blood flow. It is a form of MYOCARDIAL ISCHEMIA (insufficient blood supply to the heart muscle) caused by a decreased capacity of the coronary vessels.	6.39	7	0
Diverticula [description not available]	4.57	4	0
Colonic Diseases Pathological processes in the COLON region of the large intestine (INTESTINE, LARGE).	5.5	9	0
Fasting Hypoglycemia HYPOGLYCEMIA expressed in the postabsorptive state, after prolonged FASTING, or an overnight fast.	2.87	1	0
Hypoglycemia A syndrome of abnormally low BLOOD GLUCOSE level. Clinical hypoglycemia has diverse etiologies. Severe hypoglycemia eventually lead to glucose deprivation of the CENTRAL NERVOUS SYSTEM resulting in HUNGER; SWEATING; PARESTHESIA; impaired mental function; SEIZURES; COMA; and even DEATH.	2.87	1	0
Colonic Diseases, Functional Chronic or recurrent colonic disorders without an identifiable structural or biochemical explanation. The widely recognized IRRITABLE BOWEL SYNDROME falls into this category.	3.74	2	0
Bile Duct Obstruction, Extrahepatic [description not available]	1.95	1	0
Bile Duct Obstruction, Intrahepatic [description not available]	1.95	1	0
Cholestasis, Intrahepatic Impairment of bile flow due to injury to the HEPATOCYTES; BILE CANALICULI; or the intrahepatic bile ducts (BILE DUCTS, INTRAHEPATIC).	1.95	1	0
Diseases, Metabolic [description not available]	4.03	3	0
Metabolic Diseases Generic term for diseases caused by an abnormal metabolic process. It can be congenital due to inherited enzyme abnormality (METABOLISM, INBORN ERRORS) or acquired due to disease of an endocrine organ or failure of a metabolically important organ such as the liver. (Stedman, 26th ed)	4.03	3	0
Caries, Dental [description not available]	3.27	2	0
Dental Caries Localized destruction of the tooth surface initiated by decalcification of the enamel followed by enzymatic lysis of organic structures and leading to cavity formation. If left unchecked, the cavity may penetrate the enamel and dentin and reach the pulp.	3.27	2	0
Nutritional Disorders [description not available]	1.95	1	0
Cancer of Rectum [description not available]	1.95	1	0
Nutrition Disorders Disorders caused by nutritional imbalance, either overnutrition or undernutrition.	1.95	1	0
Rectal Neoplasms Tumors or cancer of the RECTUM.	1.95	1	0
Cecal Diseases Pathological developments in the CECUM.	1.95	1	0
Ulcer A lesion on the surface of the skin or a mucous surface, produced by the sloughing of inflammatory necrotic tissue.	3.05	5	0
Experimental Leukemia [description not available]	1.95	1	0
Colon Diverticula [description not available]	3.56	3	0
Diverticulum, Colon A pouch or sac opening from the COLON.	3.56	3	0
Brown Lung [description not available]	1.95	1	0
Animal Mammary Carcinoma [description not available]	1.97	1	0
Infections, Orthomyxoviridae [description not available]	1.97	1	0
Orthomyxoviridae Infections Virus diseases caused by the ORTHOMYXOVIRIDAE.	1.97	1	0
Dermatoses [description not available]	2.36	2	0
Skin Diseases Diseases involving the DERMIS or EPIDERMIS.	2.36	2	0
Hormone-Dependent Neoplasms [description not available]	3.8	1	0
Anaphylactic Reaction [description not available]	2.88	1	0
Anaphylaxis An acute hypersensitivity reaction due to exposure to a previously encountered ANTIGEN. The reaction may include rapidly progressing URTICARIA, respiratory distress, vascular collapse, systemic SHOCK, and death.	2.88	1	0
Enterocolitis Inflammation of the MUCOSA of both the SMALL INTESTINE and the LARGE INTESTINE. Etiology includes ISCHEMIA, infections, allergic, and immune responses.	1.97	1	0
Infectious Skin Diseases [description not available]	3.36	1	1
Infection, Wound [description not available]	3.36	1	1
Skin Diseases, Infectious Skin diseases caused by bacteria, fungi, parasites, or viruses.	3.36	1	1
Constriction, Pathological [description not available]	1.97	1	0
Complication, Postoperative [description not available]	2.64	3	0
Constriction, Pathologic The condition of an anatomical structure's being constricted beyond normal dimensions.	1.97	1	0
Postoperative Complications Pathologic processes that affect patients after a surgical procedure. They may or may not be related to the disease for which the surgery was done, and they may or may not be direct results of the surgery.	2.64	3	0
Cancer of Stomach [description not available]	1.97	1	0
Stomach Neoplasms Tumors or cancer of the STOMACH.	1.97	1	0
Germinoblastoma [description not available]	1.97	1	0
Cancer of Skin [description not available]	1.97	1	0
Lymphoma A general term for various neoplastic diseases of the lymphoid tissue.	1.97	1	0
Skin Neoplasms Tumors or cancer of the SKIN.	1.97	1	0
Primary Peritonitis [description not available]	1.97	1	0
Acute Disease Disease having a short and relatively severe course.	1.97	1	0
Peritonitis INFLAMMATION of the PERITONEUM lining the ABDOMINAL CAVITY as the result of infectious, autoimmune, or chemical processes. Primary peritonitis is due to infection of the PERITONEAL CAVITY via hematogenous or lymphatic spread and without intra-abdominal source. Secondary peritonitis arises from the ABDOMINAL CAVITY itself through RUPTURE or ABSCESS of intra-abdominal organs.	1.97	1	0
Toxemia A condition produced by the presence of toxins or other harmful substances in the BLOOD.	1.97	1	0
Arteriosclerosis, Coronary [description not available]	3.35	1	1
Apolipoprotein B-100, Familial Defective [description not available]	3.35	1	1
Coronary Artery Disease Pathological processes of CORONARY ARTERIES that may derive from a congenital abnormality, atherosclerotic, or non-atherosclerotic cause.	3.35	1	1
Hyperlipoproteinemia Type II A group of familial disorders characterized by elevated circulating cholesterol contained in either LOW-DENSITY LIPOPROTEINS alone or also in VERY-LOW-DENSITY LIPOPROTEINS (pre-beta lipoproteins).	3.35	1	1
Dermatitis, Occupational A recurrent contact dermatitis caused by substances found in the work place.	1.95	1	0
Abnormalities, Drug-Induced Congenital abnormalities caused by medicinal substances or drugs of abuse given to or taken by the mother, or to which she is inadvertently exposed during the manufacture of such substances. The concept excludes abnormalities resulting from exposure to non-medicinal chemicals in the environment.	1.95	1	0
Hematochezia The passage of bright red blood from the rectum. The blood may or may not be mixed with formed stool in the form of blood, blood clots, bloody stool or diarrhea.	1.95	1	0
Gastrointestinal Hemorrhage Bleeding in any segment of the GASTROINTESTINAL TRACT from ESOPHAGUS to RECTUM.	1.95	1	0
Phlegmasia Alba Dolens Inflammation that is characterized by swollen, pale, and painful limb. It is usually caused by DEEP VEIN THROMBOSIS in a FEMORAL VEIN, following PARTURITION or an illness. This condition is also called milk leg or white leg.	2.86	1	0
Varices [description not available]	2.86	1	0
Hemorrhoids Swollen veins in the lower part of the RECTUM or ANUS. Hemorrhoids can be inside the anus (internal), under the skin around the anus (external), or protruding from inside to outside of the anus. People with hemorrhoids may or may not exhibit symptoms which include bleeding, itching, and pain.	2.86	1	0
Thrombophlebitis Inflammation of a vein associated with a blood clot (THROMBUS).	2.86	1	0
Varicose Veins Enlarged and tortuous VEINS.	2.86	1	0
Colitis Gravis [description not available]	2.35	2	0
Colitis, Ulcerative Inflammation of the COLON that is predominantly confined to the MUCOSA. Its major symptoms include DIARRHEA, rectal BLEEDING, the passage of MUCUS, and ABDOMINAL PAIN.	2.35	2	0
Psychophysiologic Disorders A group of disorders characterized by physical symptoms that are affected by emotional factors and involve a single organ system, usually under AUTONOMIC NERVOUS SYSTEM control. (American Psychiatric Glossary, 1988)	2.86	1	0
Colitis, Granulomatous [description not available]	1.95	1	0
Kidney Stones [description not available]	2.35	2	0
Malabsorption Syndromes General term for a group of MALNUTRITION syndromes caused by failure of normal INTESTINAL ABSORPTION of nutrients.	1.95	1	0
Crohn Disease A chronic transmural inflammation that may involve any part of the DIGESTIVE TRACT from MOUTH to ANUS, mostly found in the ILEUM, the CECUM, and the COLON. In Crohn disease, the inflammation, extending through the intestinal wall from the MUCOSA to the serosa, is characteristically asymmetric and segmental. Epithelioid GRANULOMAS may be seen in some patients.	1.95	1	0
Kidney Calculi Stones in the KIDNEY, usually formed in the urine-collecting area of the kidney (KIDNEY PELVIS). Their sizes vary and most contains CALCIUM OXALATE.	2.35	2	0
Itching [description not available]	3.33	1	1
Pruritus An intense itching sensation that produces the urge to rub or scratch the skin to obtain relief.	3.33	1	1
Esophageal Fistula Abnormal passage communicating with the ESOPHAGUS. The most common type is TRACHEOESOPHAGEAL FISTULA between the esophagus and the TRACHEA.	1.94	1	0
Drowning Death that occurs as a result of anoxia or heart arrest, associated with immersion in liquid.	2.35	2	0
Celiac Sprue [description not available]	1.94	1	0
Celiac Disease A malabsorption syndrome that is precipitated by the ingestion of foods containing GLUTEN, such as wheat, rye, and barley. It is characterized by INFLAMMATION of the SMALL INTESTINE, loss of MICROVILLI structure, failed INTESTINAL ABSORPTION, and MALNUTRITION.	1.94	1	0
Sarcoma 180 An experimental sarcoma of mice.	1.94	1	0
EHS Tumor [description not available]	1.94	1	0

lignin

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