phenanthrene profile

phenanthrene : A polycyclic aromatic hydrocarbon composed of three fused benzene rings which takes its name from the two terms 'phenyl' and 'anthracene.' [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	995
CHEMBL ID	46730
CHEBI ID	28851
MeSH ID	M0098158

Synonym
CHEBI:28851 ,
9,10-dehydrophenanthrene
phenanthrin
phenanthren
nsc26256
wln: l b666j
nsc-26256
inchi=1/c14h10/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)13/h1-10
NCGC00091177-01
coal tar pitch volatiles: phenanthrene
ai3-00790
hsdb 2166
phenanthrene, pure
einecs 201-581-5
phenanthren [german]
ccris 1233
nsc 26256
ravatite
PHENANTHRENE-RING
phenanthracene
85-01-8
phenanthrene
phenanthrene, 98%
phenanthrene, analytical standard, for environmental analysis
phenanthrene, zone-refined, >=99.5%
NCGC00091177-02
phenanthrene, purum, for fluorescence, >=97.0% (hplc)
MLS002454437
smr000112025
AC-11346
CHEMBL46730 ,
PEY ,
BMSE000560
phenantrin
bdbm50159266
P1310
P0331
P0079
A841054
NCGC00091177-04
NCGC00091177-03
448j8e5bst ,
unii-448j8e5bst
tox21_300573
NCGC00254398-01
cas-85-01-8
dtxcid904254
tox21_201638
dtxsid6024254 ,
NCGC00259187-01
HMS2268O22
FT-0673667
AKOS008967330
FT-0633623
FT-0631391
(3)helicene
phenanthrene [iarc]
phenanthrene [hsdb]
phenanthrene [mi]
W-104097
mfcd00001168
STL453632
phenanthrene, certified reference material, tracecert(r)
phenanthrene, sublimed grade, >=99.5%
phenanthrene 10 microg/ml in cyclohexane
phenanthrene 10 microg/ml in acetonitrile
phenanthrene 100 microg/ml in acetonitrile
FT-0673668
Q422037
phenanthrene zone refined (number of passes:30)
AS-12847
5-amino-6-chloro-3-pyridinecarboxylicacidmethylester
EN300-18073
9-phenanthrene
CS-0013733
HY-B1727
phenanthrene 200 microg/ml in isooctane
phenanthrene zone refined
phenanthrene-13c2
P2877
phenanthrene (purified by sublimation)
phenanthrene (iarc)
Z57139327

Research Excerpts

Overview

Phenanthrene is a low molecular weight polycyclic aromatic hydrocarbon (PAH) that is composed of three fused benzene rings. Phenanthrene (Phe) is a kind of POP which existed extensively in the environment, but whose toxicity on mammals has so far received less focus.

Excerpt	Reference	Relevance
"Phenanthrene is a tricyclic polycyclic aromatic hydrocarbon and environmental contaminant found in high concentrations around urban catchments and in the vicinity of oil extraction activities. "	( Part B: Morphometric and transcriptomic responses to sub-chronic exposure to the polycyclic aromatic hydrocarbon phenanthrene in the fathead minnow (Pimephales promelas). Kidd, KA; Loughery, JR; Martyniuk, CJ; Mercer, A, 2018)	2.13
"Phenanthrene is a low molecular weight polycyclic aromatic hydrocarbon (PAH) that is composed of three fused benzene rings. "	( Part A: Temporal and dose-dependent transcriptional responses in the liver of fathead minnows following short term exposure to the polycyclic aromatic hydrocarbon phenanthrene. Kidd, KA; Loughery, JR; Martyniuk, CJ; Mercer, A, 2018)	2.12
"Phenanthrene (Phe) is a kind of POP which existed extensively in the environment, but whose toxicity on mammals has so far received less focus."	( Exposure to environmental level phenanthrene induces a NASH-like phenotype in new born rat. Guo, J; Guo, Z; Wang, C; Zuo, Z, 2018)	1.49
"Phenanthrene (PHE) is a tricyclic polycyclic aromatic hydrocarbon which distributed extensively in the aquatic environment. "	( Chronic exposure to environmental concentrations of phenanthrene impairs zebrafish reproduction. Chen, H; Chen, J; Fu, W; Peng, X; Sun, X; Yu, M, 2019)	2.21
"Phenanthrene (PHE) is a common polycyclic aromatic hydrocarbon (PAH) in aquatic environments, and this contaminant can cause adverse effects on teleostean performance. "	( Histological, biochemical and transcriptomic analyses reveal liver damage in zebrafish (Danio rerio) exposed to phenanthrene. Lai, Z; Li, H; Mai, Y; Peng, S, 2019)	2.17
"Phenanthrene (PHE) is a priority polycyclic aromatic hydrocarbon (PAH) which is toxic to aquatic organisms.However, there has been no paper dealing with water quality criteria (WQC) of PHE due to the shortage of toxicity data of different taxonomic levels. "	( Development of water quality criteria for phenanthrene and comparison of the sensitivity between native and non-native species. Liang, F; Liu, JD; Liu, ZT; Wang, WL; Wang, XN; Wu, JY; Yan, ZG, 2015)	2.12
"Phenanthrene is a major component of diesel exhaust particles and one of the most common pollutants in the environment."	( CeO2 nanoparticles induce no changes in phenanthrene toxicity to the soil organisms Porcellionides pruinosus and Folsomia candida. Jurkschat, K; Loureiro, S; Soares, AM; Svendsen, C; Tourinho, PS; van Gestel, CA; Waalewijn-Kool, PL; Zantkuijl, I, 2015)	1.41
"Phenanthrene (PHE) is an abundant polycyclic aromatic hydrocarbon (PAH), widely distributed in aquatic environment. "	( Histological responses and localization of the cytochrome P450 (CYP2AU1) in Crassostrea brasiliana exposed to phenanthrene. Bainy, AC; Bícego, MC; Cargnin-Ferreira, E; dos Reis, IM; Flores-Nunes, F; Garcez, RC; Mattos, JJ; Miguelão, T; Sasaki, ST; Taniguchi, S; Toledo-Silva, G; Zacchi, FL, 2015)	2.07
"Phenanthrene is a ubiquitous pollutant in water and air, and the cellular targets for this compound are highly conserved across vertebrates."	( A Novel Cardiotoxic Mechanism for a Pervasive Global Pollutant. Block, BA; Brette, F; Cros, C; Galli, GL; Incardona, JP; Scholz, NL; Shiels, HA, 2017)	1.18
"Phenanthrene is a low-toxicity, non-cytochrome P4501A (CYP1A)-inducing compound that accumulates in fish tissues during exposure to lethal concentrations in water."	( Altering cytochrome P4501A activity affects polycyclic aromatic hydrocarbon metabolism and toxicity in rainbow trout (Oncorhynchus mykiss). Billiard, SM; Brown, RS; Hawkins, SA; Hodson, PV; Tabash, SP, 2002)	1.04
"Phenanthrene is a three-ring polycyclic aromatic hydrocarbon and commonly found as a pollutant in various environments. "	( Degradation of phenanthrene by Trametes versicolor and its laccase. Choi, HT; Han, MJ; Song, HG, 2004)	2.12

Effects

Excerpt	Reference	Relevance
"Phenanthrene accumulation has significant and positive effects on increase of glutamate, 5-aminolevulinic acid, uroporphyrinogen III, protoporphyrin IX, Mg-protoporphyrin IX and protochlorophyllide concentrations."	( Phenanthrene-triggered Chlorosis is caused by elevated Chlorophyll degradation and leaf moisture. Gu, R; Li, J; Shen, Y; Xing, B; Yue, L; Zhan, X, 2017)	2.62

Treatment

Excerpt	Reference	Relevance
"Phenanthrene treatment in combination with LPS induced AhR protein expression and Cyp1A1 gene transcription, which not was observed combining poly I: C and phenanthrene."	( Aryl hydrocarbon receptor protein and Cyp1A1 gene induction by LPS and phenanthrene in Atlantic cod (Gadus morhua) head kidney cells. Holen, E; Olsvik, PA, 2014)	1.36

Toxicity

The lowest observable adverse effect concentration (LOAEC) was 10 mg/kg for phenanthrene when tested with green onion. The aim of this study was to evaluate the combined toxic effects of micro-phenanthrene and retene on the early life stage of marine medaka.

Excerpt	Reference	Relevance
" Although the ozonation products of pyrene were not toxic under the conditions of this study, phenanthrene products were more hepatotoxic than was phenanthrene itself."	( Toxicity of polycyclic aromatic hydrocarbons. I. Effect of phenanthrene, pyrene, and their ozonized products on blood chemistry in rats. Church, DF; Flory, W; Giamalva, D; Pryor, WA; Ruhr, LP; Yoshikawa, T, 1985)	0.73
"The authors previously demonstrated that simulated solar radiation (SSR), with a fluence rate of only 40 mumol m-2 sec-1, increased polycyclic aromatic hydrocarbon (PAH) toxicity to the duckweed Lemna gibba and that PAHs photomodified in SSR (generally oxygenation of the ring system) are more toxic than the parent compounds (Huang et al."	( Increased polycyclic aromatic hydrocarbon toxicity following their photomodification in natural sunlight: impacts on the duckweed Lemna gibba L. G-3. Dixon, DG; Greenberg, BM; Huang, XD, 1995)	0.29
" This study has shown that the three polycyclic aromatic hydrocarbons tested are not acutely toxic to the prokaryotic biosensors tested, although acute toxicity has been shown in other bioassays."	( Feasibility of using prokaryote biosensors to assess acute toxicity of polycyclic aromatic hydrocarbons. Macleod, CJ; Paton, GI; Reid, BJ; Semple, KT; Weitz, HJ, 1998)	0.3
" Toxic effects were measured as reductions in survival and reproductive output after 3 weeks of exposure."	( Studies on the effect of soil aging on the toxicity of pyrene and phenanthrene to a soil-dwelling springtail. Jensen, J; Krogh, PH; Stenersen, J; Sverdrup, LE, 2002)	0.55
" The lowest observable adverse effect concentration (LOAEC) was 10 mg/kg for phenanthrene when tested with green onion, and 50 mg/kg for pyrene when tested with wheat."	( Phytotoxicity assessment of phenanthrene, pyrene and their mixtures by a soil-based seedling emergence test. Gong, P; Song, YF; Sun, TH; Zhou, QX, 2005)	0.85
" To explain this inhibition, the cell growths of both strains were monitored with various concentrations of rhamnolipid, which showed significant toxic effects toward strain 3Y, but was nontoxic toward 4-3."	( Toxic effect of biosurfactant addition on the biodegradation of phenanthrene. Ahn, Y; Kim, KW; Shin, KH, 2005)	0.57
" The synergistic effect to copepods is a concern as it indicates that greater toxic effects may occur when the compounds are present in mixtures."	( Toxicity of phenanthrene and lindane mixtures to marine invertebrates. Evans, AD; Nipper, M, 2007)	0.72
" It was hypothesized that excessive biomass in testing systems prevents a critical body residue of HOCs from forming, thus curbing toxic effects."	( The influence of biomass on the toxicity of hydrophobic organic contaminants. Evans, AD; Nipper, M, 2008)	0.35
" Four common environmental contaminants (atrazine, methyl parathion, pentachlorophenol (PCP), and phenanthrene) were used as model compounds, representing different physico-chemical properties and toxic modes of action."	( Toxicity and bioaccumulation of xenobiotic organic compounds in the presence of aqueous suspensions of aggregates of nano-C(60). Baun, A; Hartmann, NB; Koch, CB; Rasmussen, RF; Sørensen, SN, 2008)	0.56
"The aim of this study was to compare the toxic effects of selected two- and three-ringed PAHs (naphthalene, phenanthrene, and anthracene) and their N-heterocyclic analogs with one (quinoline, acridine, and phenanthridine) or two (quinoxaline, phenazine, and 1,10-phenanthroline) nitrogen atoms on the survival and reproduction of Enchytraeus crypticus in artificial soil."	( Toxic effects of nine polycyclic aromatic compounds on Enchytraeus crypticus in artificial soil in relation to their properties. Brezovský, J; Hofman, J; Kobetičová, K; Simek, Z, 2011)	0.58
"Polycyclic aromatic hydrocarbons (PAHs) constituents, such as phenanthrene (PH) and anthracene (AN), are considered toxic for marine organisms, including bivalve mollusks."	( Generation of free radicals in haemocytes of mussels after exposure to low molecular weight PAH components: immune activation, oxidative and genotoxic effects. Dailianis, S; Giannapas, M; Karnis, L, 2012)	0.62
" Concentrations shown to cause adverse effects in this study are in the range of previous studies that have investigated the chronic effects of phenanthrene on fish."	( A novel passive dosing system for determining the toxicity of phenanthrene to early life stages of zebrafish. Bragin, GE; Butler, JD; Cooper, KR; Lampi, MA; Letinski, DJ; Parkerton, TF, 2013)	0.83
"In the present work, the influences of suspended sediment (SPS) on the toxic effects of phenanthrene (PHE), one kind of polycyclic aromatic hydrocarbons, to Daphnia magna was studied using a dialysis bag simulation system, which equalized the freely dissolved concentration of PHE between outside the dialysis bag in the presence of SPS and inside the dialysis bag in the absence of SPS."	( Enhancement of toxic effects of phenanthrene to Daphnia magna due to the presence of suspended sediment. Bao, Y; Dong, J; Li, H; Xia, X; Zhang, X, 2014)	0.91
" Bioremediation counter balanced the toxic effects of phenanthrene since meiofauna and bacteria abundances were significantly higher (p < 0."	( Biostimulation as an attractive technique to reduce phenanthrene toxicity for meiofauna and bacteria in lagoon sediment. Aissa, P; Cravo-Laureau, C; Duran, R; Got, P; Louati, H; Mahmoudi, E; Pringault, O; Said, OB; Soltani, A, 2014)	0.9
" However, because US PAH-derived toxic intermediates are difficult to detect, the present study investigates aqueous PH toxicity before and after high-frequency US degradation, in hemocytes of mussel Mytilus galloprovincialis."	( Aqueous phenanthrene toxicity after high-frequency ultrasound degradation. Dailianis, S; Karapanagioti, HK; Manariotis, ID; Melas, K; Tsarpali, V, 2014)	0.84
" A comparative study of the toxic effects of phenanthrene and retene (7-isopropyl-1-methylphenanthrene, an alkyl-phenanthrene) on the early life stage of marine medaka (Oryzias melastigma) was conducted."	( Comparative embryotoxicity of phenanthrene and alkyl-phenanthrene to marine medaka (Oryzias melastigma). Hong, H; Jin, F; Mu, J; Wang, J; Wang, X, 2014)	0.95
"The objective of this study was to assess potential toxic effects of phenanthrene (PHE) on tissues of clam Venerupis philippinarum using parameters of antioxidant defenses and oxidative stress."	( Toxicity assessment of environmental pollutant phenanthrene in clam Venerupis philippinarum using oxidative stress biomarkers. Pan, L; Tao, Y; Zhang, H, 2014)	0.89
" Photo-enhanced toxicity from co-exposure to ultraviolet (UV) radiation and PAHs enhanced the toxicity and exhibited toxic effects at PAH concentrations orders of magnitude below effects observed in the absence of UV."	( Acute photo-induced toxicity and toxicokinetics of single compounds and mixtures of polycyclic aromatic hydrocarbons in zebrafish. Oris, JT; Willis, AM, 2014)	0.4
" CeO2 NPs had no adverse effects on isopod survival and growth or springtail survival and reproduction."	( CeO2 nanoparticles induce no changes in phenanthrene toxicity to the soil organisms Porcellionides pruinosus and Folsomia candida. Jurkschat, K; Loureiro, S; Soares, AM; Svendsen, C; Tourinho, PS; van Gestel, CA; Waalewijn-Kool, PL; Zantkuijl, I, 2015)	0.68
" Therefore, we aimed to determine the toxic effects of PAHs on earthworms."	( Determination of biomarkers for polycyclic aromatic hydrocarbons (PAHs) toxicity to earthworm (Eisenia fetida). Cho, K; Jeon, HJ; Lee, SE; Mo, HH; Nam, TH; Ok, YS, 2015)	0.42
" The ∑PAH16 in all sediments were significantly lower than probable effect concentrations (PEC), while ∑PAH16 at nine sites of the Daliao River system were between threshold effect concentrations (TEC) and PEC, suggesting that adverse effects were possible at the nine sites."	( Spatial distribution and potential toxicity of polycyclic aromatic hydrocarbons in sediments from Liaohe River Basin, China. Guo, C; He, Y; Meng, W; Xu, J; Zhang, Y, 2016)	0.43
" FPs are strong adsorbents for hydrophobic toxic pollutants and may affect their fate and toxicity in the environment; however, such information is still rare."	( Effects of nanoplastics and microplastics on toxicity, bioaccumulation, and environmental fate of phenanthrene in fresh water. Cao, S; Guo, H; Huang, A; Ji, R; Ma, Y; Sun, F; Wang, L, 2016)	0.65
" In the present study, we have made comparisons of constitutive androstane receptor (CAR) activation and toxic effects on the liver between these two isomers."	( Phenanthrene, but not its isomer anthracene, effectively activates both human and mouse nuclear receptor constitutive androstane receptor (CAR) and induces hepatotoxicity in mice. Cheng, R; Deng, W; Lu, M; Shi, Z; Wang, XX; Yang, H; Zeng, Y; Zhang, SY; Zhao, LY; Zhu, J, 2019)	1.96
" In this study, the single and mixture toxic effects of MC-LR and Phe mixtures were investigated in Daphnia magna after acute and chronic exposure."	( Acute and chronic toxicity of microcystin-LR and phenanthrene alone or in combination to the cladoceran (Daphnia magna). Cheng, C; Gu, Y; Shu, X; Wan, X; Xie, L; Zhao, Y, 2021)	0.88

Compound-Compound Interactions

Excerpt	Reference	Relevance
" In this work, aiming at the actual problems that water environment is polluted and human health is threatened by PAHs, surface enhanced Raman spectroscopy (SERS) combined with Random Forest (RF) calibration models were used to quantitative analysis of phenanthrene and fluoranthene in water."	( Quantitative analysis of polycyclic aromatic hydrocarbons (PAHs) in water by surface-enhanced Raman spectroscopy (SERS) combined with Random Forest. Chen, T; Fu, H; Guo, M; Li, H; Li, M; Tang, H; Zhang, T; Zhang, Y, 2023)	1.09

Bioavailability

A method using semi-permeable membrane device (SPMD) to study desorption of HOCs in soils has been set up. The most prominent effects on phenanthrene degradation kinetics were a five to fifteen fold increase in the linear growth term (k(2) and 23-27% increase in bioavailability factor S(0) for SW high and FW multi respectively.

Excerpt	Reference	Relevance
" These highly lipophilic compounds are well absorbed in the intestine."	( The influence of bile on the bioavailability of polynuclear aromatic hydrocarbons from the rat intestine. Barrowman, JA; Rahimtula, A; Rahman, A, 1986)	0.27
" Growth of mixed cultures with phenanthrene and fluoranthene solubilized by a nonionic surfactant prior to inoculation was exponential, indicating a high bioavailability of the solubilized hydrocarbons."	( Degradation of polycyclic aromatic hydrocarbons in the presence of synthetic surfactants. Tiehm, A, 1994)	0.57
" Development of such techniques, especially those involving inoculation with microbial strains, should consider physical mass transfer limitations and potential decreases in bioavailability over time."	( Biodegradation of sorbed chemicals in soil. Fan, S; Johnson, C; Ma, GM; Scow, KM, 1995)	0.29
" The results suggest that some phytogenic surfactants might improve PAH bioavailability in rhizospheres."	( Influence of phytogenic surfactants (quillaya saponin and soya lecithin) on bio-elimination of phenanthrene and fluoranthene by three bacteria. Haegel, FH; Kleespies, M; Kneifel, H; Papaderos, A; Soeder, CJ; Webb, L, 1996)	0.51
" Surfactants have been suggested to enhance the bioavailability of hydrophobic compounds, but both negative and positive effects of surfactants on biodegradation have been reported in the literature."	( Quantifying the biodegradation of phenanthrene by Pseudomonas stutzeri P16 in the presence of a nonionic surfactant. Aitken, MD; Grimberg, SJ; Stringfellow, WT, 1996)	0.57
" Bioaccumulation was found to be reduced by changes in bioavailability associated with aging of the PAH-amended soil."	( Earthworm and food interactions on bioaccumulation and disappearance in soil of polycyclic aromatic hydrocarbons: studies on phenanthrene and fluoranthene. Bodt, J; Immerzeel, J; Ma, WC, 1995)	0.5
" Bioavailability of sediment-sorbed PAHs declined with contact time between sediment and animals."	( Accumulation kinetics of polycyclic aromatic hydrocarbons adsorbed to sediment by the mollusk Corbicula fluminea. Djomo, JE; Ferrier, V; Garrigues, P; Narbonne, JF; Ribera, D, 1999)	0.3
" These results confirm that the activity of the strain 2MPII is limited by the bioavailability of the polycyclic aromatic hydrocarbon (PAH) substrate in the aqueous phase."	( Enhanced biodegradation of phenanthrene by a marine bacterium in presence of a synthetic surfactant. Acquaviva, M; Bertrand, JC; Cuny, P; Faucet, J; Gilewicz, M, 1999)	0.6
"The sorption of organic contaminants by natural organic matter (NOM) often limits substrate bioavailability and is an important factor affecting microbial degradation rates in soils and sediments."	( Effect of model sorptive phases on phenanthrene biodegradation: different enrichment conditions influence bioavailability and selection of phenanthrene-degrading isolates. Friedrich, M; Grosser, RJ; Inskeep, WP; Ward, DM, 2000)	0.58
"Reduced bioavailability of nonpolar contaminants due to sorption to natural organic matter is an important factor controlling biodegradation of pollutants in the environment."	( Effect of model sorptive phases on phenanthrene biodegradation: molecular analysis of enrichments and isolates suggests selection based on bioavailability. Friedrich, M; Grosser, RJ; Inskeep, WP; Kern, EA; Ward, DM, 2000)	0.58
" Fluorescence measurements showed that this effect was not due to an increasing biomass, but to an augmentation of bioavailability of the phenanthrene through increasing the apparent dissolved pollutant."	( Microbial degradation of phenanthrene by addition of a sophorolipid mixture. Gessner, K; Müller, T; Scheper, T; Schippers, C, 2000)	0.81
" However, contaminant bioavailability can be species-specific."	( Phenanthrene degradation in soils co-inoculated with phenanthrene-degrading and biosurfactant-producing bacteria. Cha, DK; Dean, SM; Jin, Y; Radosevich, M; Wilson, SV, )	1.57
" The biosurfactant, rhamnolipids, was used to extract a model PAH, phenanthrene, and was found to enhance the bioavailability of phenanthrene via an increase in its rate of mass transfer from sorbed soil to the aqueous phase."	( Soil biosensor for the detection of PAH toxicity using an immobilized recombinant bacterium and a biosurfactant. Chang, ST; Gu, MB, 2001)	0.55
" We suggest that rhamnolipid production and attachment increased the bioavailability of phenanthrene, so promoting biodegradation activity."	( Bioavailability of solid and non-aqueous phase liquid (NAPL)-dissolved phenanthrene to the biosurfactant-producing bacterium Pseudomonas aeruginosa 19SJ. De Olmedo, E; García-Junco, M; Ortega-Calvo, JJ, 2001)	0.77
" Because bioavailability of the contaminants is of great importance for a successful bioremediation, a chemical pre-oxidation step by ozone was tested to enhance the subsequent biodegradation steps."	( Basic examinations on chemical pre-oxidation by ozone for enhancing bioremediation of phenanthrene contaminated soils. Kamnerdpetch, C; Müller, T; Scheper, T; Stehr, J; Svensson, K, 2001)	0.53
" With properly designed experiments, the results of this study suggest that the supercritical fluid system could be extended to the study of contaminant aging and bioavailability in natural soils and sediments."	( Artificial aging of phenanthrene in porous silicas using supercritical carbon dioxide. Fortman, T; Huesemann, MH; Parker, KE; Peyton, B; Riley, RG; Thompson, CJ; Truex, MJ; Wang, Z, 2001)	0.63
" Root exudates significantly enhanced phenanthrene biodegradation in rhizosphere soils, either by increasing contaminant bioavailability and/or increasing microbial population size and activity."	( Enhanced phenanthrene biodegradation in soil by slender oat root exudates and root debris. Firestone, MK; Miya, RK, )	0.82
" Many studies have shown a negative correlation between aging and the biodegradation of polycyclic aromatic hydrocarbons (PAHs), indicating a reduction in the bioavailability of PAHs to micro-organisms with time."	( Studies on the effect of soil aging on the toxicity of pyrene and phenanthrene to a soil-dwelling springtail. Jensen, J; Krogh, PH; Stenersen, J; Sverdrup, LE, 2002)	0.55
" Results agree with the literature that PAHs are poorly absorbed through the skin from solids."	( Dermal exposure assessment of polycyclic aromatic hydrocarbons: in vitro percutaneous penetration from coal dust. Bussani, R; Cavallo, D; Foà, V; Montomoli, L; Sartorelli, P; Sisinni, AG, 2001)	0.31
", humic and fulvic acids) in bioavailability of aged phenanthrene with time."	( Role of loosely bound humic substances and humin in the bioavailability of phenanthrene aged in soil. Kim, JY; Nam, K, 2002)	0.79
" Therefore, PAH bioavailability in the aged soils can be underestimated when the microbial activity is determined only from the stagnant solution."	( Biodegradability of aged pyrene and phenanthrene in a natural soil. Cutright, TJ; Hwang, S, 2002)	0.59
"13 for reversibly sorbed phenanthrene and desorption-resistant phenanthrene, respectively, indicating a significantly reduced bioavailability of desorption-resistant phenanthrene."	( Bioavailability of desorption-resistant phenanthrene to the oligochaete Ilyodrilus templetoni. Chai, Y; Fleeger, JW; Lu, X; Reible, DD, 2003)	0.89
" Soil slurries 1:2 or greater, but less than 1:5 (soil:water), are recommended for bioassay determinations of total contaminant bioavailability due to greater overall mineralisation and improved reproducibility."	( The effect of soil: water ratios on the mineralisation of phenanthrene: LNAPL mixtures in soil. Doick, KJ; Semple, KT, 2003)	0.56
" These findings suggest that the physicochemical properties of the xenobiotics and intestinal epithelium play key roles in the selective permeability and in the bioavailability of the tested micropollutants."	( Intestinal absorption of 14C from 14C-phenanthrene, 14C-benzo[a]pyrene and 14C-tetrachlorodibenzo-para-dioxin: approaches with the Caco-2 cell line and with portal absorption measurements in growing pigs. Cavret, S; Feidt, C; Laurent, C; Laurent, F; Rychen, G, )	0.4
"Polycyclic aromatic hydrocarbon (PAHs)-degrading bacteria may enhance the bioavailability of PAHs by excreting biosurfactants, by production of extracellular polymeric substances, or by forming biofilms."	( Evaluation of bacterial strategies to promote the bioavailability of polycyclic aromatic hydrocarbons. Johnsen, AR; Karlson, U, 2004)	0.32
" The bioavailability of phenanthrene to the bacteria isolated from the petroleum contaminated soils was studied based on the rotary flasks experiments."	( Influence of nonionic surfactant on the solubilization and biodegradation of phenanthrene. Liu, X; Long, T; Peng, S; Yang, JG; Yu, G; Zheng, L, 2003)	0.85
"The soil matrix can impact the bioavailability of soil-bound organic chemicals, and this impact is governed in part by soil properties such as organic carbon (OC) content, clay minerals, and pH."	( Evaluation of a rat model versus a physiologically based extraction test for assessing phenanthrene bioavailability from soils. Carlson, GP; Galinsky, RE; Lee, LS; Pu, X, 2004)	0.55
" In perspective, it would be interesting to assess the bioavailability of PAHs in the presence of metals in further experiments."	( Effect of metals on the adsorption and extractability of 14C-phenanthrene in soils. Amellal, S; Morel, JL; Perrin-Ganier, C; Saison, C; Schiavon, M, 2004)	0.56
"The objective of this study was to quantify the bioavailability of phenanthrene solubilized in surfactants by a mixed phenanthrene-degrading culture isolated from the petroleum contaminated soils."	( [The influence on the biodegradation of phenanthrene by nonionic surfactant, Tween20]. Liu, X; Liu, Z; Long, T; She, P; Yang, JG; Yu, G, 2004)	0.83
"The bioavailability and biodegradation of polycyclic aromatic hydrocarbons (PAHs) can be increased through the addition of surfactants."	( Effect of surfactants on solubilization and degradation of phenanthrene under thermophilic conditions. Fang, M; Wong, JW; Xing, B; Zhao, Z, )	0.37
" Evidence is presented for the application of Raman spectroscopy as a bioassay for pollutant bioavailability and toxicity."	( Insight into pollutant bioavailability and toxicity using Raman confocal microscopy. Helm, J; Huang, WE; Singer, AC; Thompson, IP, 2005)	0.33
" Potent and specific inhibitors of the CYP2A6 enzyme can be used in the future to increase nicotine bioavailability and thus make oral nicotine administration feasible in smoking cessation therapy."	( Quantitative structure-activity relationship analysis of inhibitors of the nicotine metabolizing CYP2A6 enzyme. Juvonen, RO; Poso, A; Rahnasto, M; Raunio, H; Wittekindt, C, 2005)	0.33
" These findings suggested that intestinal metabolism might play a key role in intestinal barrier permeability and thus in the bioavailability of tested micropollutants."	( Intestinal metabolism of PAH: in vitro demonstration and study of its impact on PAH transfer through the intestinal epithelium. Cavret, S; Feidt, C, 2005)	0.33
" This was attributed to the reduced bioavailability of phenanthrene, due to its increased solubilization extent in the micellar phase and possibly lowered mass transfer rate from the micellar phase into the aqueous phase or into the bacterial cells."	( Effect of a commercial alcohol ethoxylate surfactant (C11-15E7) on biodegradation of phenanthrene in a saline water medium by Neptunomonas naphthovorans. Bai, R; Li, JL, 2005)	0.8
"The goal of these studies was to determine how sorption by humic acids affected the bioavailability of polynuclear aromatic hydrocarbons (PAHs) to PAH-degrading microbes."	( Isolation of soil bacteria adapted to degrade humic acid-sorbed phenanthrene. Bleam, WF; Hickey, WJ; Vacca, DJ, 2005)	0.57
"The aim of this study was to investigate the influence of diesel on the loss and bioavailability of soil-associated [14C]phenanthrene with time."	( Influence of diesel concentration on the fate of phenanthrene in soil. Reid, BJ; Swindell, AL, 2006)	0.8
" The observed low bioavailability of PAHs probably inhibited PAH phytoremediation, as diffusion-limited mass transfer would limit the release of PAHs to the aqueous phase."	( Physicochemical characterization of coke-plant soil for the assessment of polycyclic aromatic hydrocarbon availability and the feasibility of phytoremediation. Ahn, S; Luthy, RG; Werner, D, 2005)	0.33
" frequentans increased the flux, lability and mobility of trace metal species and therefore the likely metal bioavailability to plants."	( Impact of microbial activity on copper, lead and nickel mobilization during the bioremediation of soil PAHs. Amezcua-Allieri, MA; Lead, JR; Rodríguez-Vázquez, R, 2005)	0.33
" Model results suggest that partitioning of the phenanthrene into the hexadecane phase limits bioavailability at high NAPL mass."	( Influence of a nonaqueous phase liquid (NAPL) on biodegradation of phenanthrene. Kight, WB; Maier, RM; Maier, WJ; Sandrin, TR, 2006)	0.83
" Overall, a single HPCD-extraction technique proved accurate and reproducible for the estimation of PAH bioavailability from soil."	( Further validation of the HPCD-technique for the evaluation of PAH microbial availability in soil. Clasper, PJ; Doick, KJ; Semple, KT; Urmann, K, 2006)	0.33
" In addition, high adsorption capacity of PAHs by carbon nanotubes may add to their high environmental risks once released to the environment, and result in potential alteration of PAHs fate and bioavailability in the environment."	( Adsorption of polycyclic aromatic hydrocarbons by carbon nanomaterials. Xing, B; Yang, K; Zhu, L, 2006)	0.33
" The influence of diesel on the ability of a cyclodextrin based extraction method to predict the microbial bioavailability of 14C-residues was also assessed."	( The influence of a NAPL on the loss and biodegradation of 14C-phenanthrene residues in two dissimilar soils. Reid, BJ; Swindell, AL, 2007)	0.58
"Two chemical approaches, Tenax extraction and matrix solid-phase microextraction (matrix-SPME), were compared to assess the bioavailability of hydrophobic contaminants from sediment."	( Comparison of chemical approaches for assessing bioavailability of sediment-associated contaminants. Landrum, PF; Lydy, MJ; You, J, 2006)	0.33
" Aim of this work is to test this hypothesis by assessing the effects of compost amendment on the bioavailability and degradation of phenanthrene in soil."	( Bioavailability and degradation of phenanthrene in compost amended soils. Cappa, F; Del Re, AA; Fragoulis, G; Puglisi, E; Trevisan, M, 2007)	0.82
" Hexadecane increased Phe bioavailability for C(I-AT) bacteria which degraded Phe according to first-order kinetics."	( Biodegradation of phenanthrene and analysis of degrading cultures in the presence of a model organo-mineral matrix and of a simulated NAPL phase. Andreoni, V; Bernasconi, S; Cavalca, L; Colombo, M; Gianfreda, L; Rao, MA, 2008)	0.68
" These data demonstrate that the fractions of NOM retained phenanthrene to a varying extent and thus the predictions of phenanthrene bioavailability should also be assessed on the basis of the constituents of the NOM matrix."	( Phenanthrene release from natural organic matter surrogates under simulated human gastrointestinal conditions. Basta, NT; Hatcher, PG; Hurdzan, CM; Tuovinen, OH, 2008)	2.03
"It is well documented that the bioavailability of hydrophobic organic chemicals (HOCs) can vary substantially among sediments."	( Characterization of polycyclic aromatic hydrocarbon bioavailability in estuarine sediments using thin-film extraction. Birch, GE; Gobas, FA; Golding, CJ, 2007)	0.34
"Recent reports suggest that Mycobacterium is better adapted to soils containing poorly bioavailable polycyclic aromatic hydrocarbons (PAHs) compared to Sphingomonas."	( Differential responses of eubacterial, Mycobacterium, and Sphingomonas communities in polycyclic aromatic hydrocarbon (PAH)-contaminated soil to artificially induced changes in PAH profile. Bastiaens, L; Ortega-Calvo, JJ; Spoden, A; Springael, D; Uyttebroek, M; Wattiau, P; Wouters, K, )	0.13
" However, can be the fate, behaviour and effects of contaminants in artificial soil extrapolated to natural soils? The aim of our study was to verify this hypothesis by comparing the loss, extraction, and bioavailability of phenanthrene in three artificial and three natural soils of comparable organic carbon content."	( Fate and behaviour of phenanthrene in the natural and artificial soils. Hofman, J; Rhodes, A; Semple, KT, 2008)	0.85
" OECD), which may lead to substantial differences in the bioavailability of test substances."	( Development of phenanthrene catabolism in natural and artificial soils. Hofman, J; Rhodes, AH; Semple, KT, 2008)	0.7
" Previous studies investigating sediments from Boston Harbor determined that significant binding of contaminants to organic matter led to insufficient evidence of the bioavailability of HOCs in porewater toxicity tests."	( The influence of biomass on the toxicity of hydrophobic organic contaminants. Evans, AD; Nipper, M, 2008)	0.35
"In order to develop a new method to study the desorption and bioavailability of hydrophobic organic chemicals (HOCs) in soils, a method using semi-permeable membrane device (SPMD) to study desorption of HOCs in soils has been set up, and assisted desorption of polycyclic aromatic hydrocarbons (PAHs), phenanthrene(PHE), pyrene(PYE), and benzo[a] pyrene (B[a]PYE) in three different kinds of soils was studied using SPMD."	( [Desorption of polycyclic aromatic hydrocarbons in soils assisted by SPMD]. Huo, C; Sun, HW; Wang, CP, 2007)	0.51
" Interestingly, the concurrent biodegradation of the surfactants reduced their effective concentrations for micelle formation and, hence, contribute to the higher bioavailability of phenanthrene by gradually releasing phenanthrene molecules into the aqueous phase."	( Effect of nonionic surfactants on biodegradation of phenanthrene by a marine bacteria of Neptunomonas naphthovorans. Chen, BH; Li, JL, 2009)	0.8
"The aim of the present study was to determine to what degree the sewage sludge sorption capacity to phenanthrene influences on bioavailability of this compound during composting."	( Sorption of phenanthrene by sewage sludge during composting in relation to potentially bioavailable contaminant content. Oleszczuk, P, 2009)	0.95
" While the positive effect of Tween 80 on PYR removal could probably due to its capacities to enhance PYR bioavailability in soil."	( Effects of pig manure compost and nonionic-surfactant Tween 80 on phenanthrene and pyrene removal from soil vegetated with Agropyron elongatum. Cheng, KY; Lai, KM; Wong, JW, 2008)	0.58
" Results indicate that non-linearity would not significantly affect bioavailability in low f(oc) geosorbents."	( Naphthalene and phenanthrene sorption to very low organic content diatomaceous earth: modeling implications for microbial bioavailability. Mittal, M; Rockne, KJ, 2009)	0.7
" In static sorption, the sorption capacity and sorption intensity were reduced with the inoculation of Sphingomonas, a PAH-degrading bacterial isolate, suggesting that the inoculum even though inactive and/or dead would enhance bioavailability of Phe."	( Static and dynamic sorption of phenanthrene in mangrove sediment slurry. Chen, JL; Tam, NF; Wong, YS, 2009)	0.64
" Therefore, once released in the environment, NPs such as nano-Al(2)O(3) will strongly alter the environmental transport, fate, and bioavailability of HOCs and could be potentially more toxic due to the adsorbed toxic chemicals."	( Sorption of phenanthrene by nanosized alumina coated with sequentially extracted humic acids. Xing, B; Yang, K; Zhu, L, 2010)	0.74
" In the present study, the effect of a coal-derived activated carbon on the bioavailability of phenanthrene (PHE) during its degradation by Mycobacterium vanbaalenii PYR-I was measured in three soils."	( Effect of activated carbon on microbial bioavailability of phenanthrene in soils. Crowley, D; Gan, J; Hunter, W; Tao, S; Yang, Y, 2009)	0.81
"The present study describes the phenanthrene-degrading activity of Sphingomonas paucimobilis 20006FA and its ability to promote the bioavailability of phenanthrene."	( Study of the degradation activity and the strategies to promote the bioavailability of phenanthrene by Sphingomonas paucimobilis strain 20006FA. Berthe-Corti, L; Coppotelli, BM; Del Panno, MT; Dias, RL; Ibarrolaza, A; Morelli, IS, 2010)	0.87
" Bioavailability was judged from growth rates on phenanthrene and from specific induction of a phenanthrene-responsive GFP-reporter in Burkholderia sartisoli strain RP037."	( Effect of two types of biosurfactants on phenanthrene availability to the bacterial bioreporter Burkholderia sartisoli strain RP037. Tecon, R; van der Meer, JR, 2010)	0.88
"The bioavailability of PAHs in sedimentary pore waters can be accurately determined by application of PDMS fibers (without requiring negligible depletion) in the presence of natural DOM with different sorption affinity for PAHs."	( Influence of temperature and origin of dissolved organic matter on the partitioning behavior of polycyclic aromatic hydrocarbons. Govers, HA; Haftka, JJ; Parsons, JR, 2010)	0.36
"Carbonaceous sorbents including black carbon (BC) and carbon nanotubes have attracted research attention around the world because of their effects on bioavailability of hydrophobic organic compounds (HOCs) in sediments and soils."	( Bioavailability of adsorbed phenanthrene by black carbon and multi-walled carbon nanotubes to Agrobacterium. Feng, C; Li, Y; Xia, X; Zhou, Z, 2010)	0.65
" Biosurfactants can increase soil-sorbed PAHs desorption, solubilisation, and dissolution into the aqueous phase, which increases the bioavailability of PAHs for microbial metabolism."	( The role of salicylate and biosurfactant in inducing phenanthrene degradation in batch soil slurries. Elliot, R; Gottfried, A; Singhal, N; Swift, S, 2010)	0.61
" While many studies show a correlation between the rapid desorption HOC pool and bioavailability to benthic organisms, bioavailability of the slow or very slow desorption fraction is still poorly understood."	( Bioavailability of sorbed phenanthrene and permethrin in sediments to Chironomus tentans. Chen, Y; Cui, X; Gan, J; Hunter, W; Yang, Y, 2010)	0.66
"46) suggesting that 1H NMR metabolomics offers considerable promise as a novel, molecular-level method to directly monitor the bioavailability of contaminants to earthworms in the environment."	( Correlations of Eisenia fetida metabolic responses to extractable phenanthrene concentrations through time. Celejewski, M; McKelvie, JR; Simpson, AJ; Simpson, MJ; Wolfe, DM, 2010)	0.6
" Molecular-level HOC-soil organic matter (SOM) interactions and associated impacts on its bioavailability were investigated in this study."	( Effects of composition and domain arrangement of biopolymer components of soil organic matter on the bioavailability of phenanthrene. Shu, L; Tao, S; Wang, X; Xing, B; Yang, Y, 2010)	0.57
" This was partly attributed to low bioavailability and microbial toxicity of the xenobiotics."	( Toxicity of xenobiotics during sulfate, iron, and nitrate reduction in primary sewage sludge suspensions. Elsgaard, L, 2010)	0.36
" This study supports the use of bile fluorescence in Nile tilapia by fixed wavelength fluorescence and synchronous fluorescence spectrometry with non-normalized data as a simple method for screening bioavailability of these PAHs."	( Assessment of bile fluorescence patterns in a tropical fish, Nile tilapia (Oreochromis niloticus) exposed to naphthalene, phenanthrene, pyrene and chrysene using fixed wavelength fluorescence and synchronous fluorescence spectrometry. Hemachandra, CK; Pathiratne, A; Pathiratne, KA, 2010)	0.57
"The nature of bioavailability of DNA-intercalated PAHs in aqueous solution was investigated."	( Nature of bioavailability of DNA-intercalated polycyclic aromatic hydrocarbons to Sphingomonas sp. Ichikawa, H; Iimura, Y; Navarro, RR; Tatsumi, K, 2010)	0.36
" viminalis or the surfactant enhanced PAH degradation, primarily by a rhizosphere effect on the microbial activity in the former case and by increased bioavailability in the latter case."	( Degradation of PAH in a creosote-contaminated soil. A comparison between the effects of willows (Salix viminalis), wheat straw and a nonionic surfactant. Castillo, Mdel P; Granhall, U; Hultgren, J; Pizzul, L, 2010)	0.36
" However, during remediation processes, changes in bioavailability and metabolite production can occur, making it necessary to incorporate an ecotoxicity assessment to estimate the risk to ecological receptors."	( Bioventing remediation and ecotoxicity evaluation of phenanthrene-contaminated soil. Babín, M; Escolano, O; Fernández, MD; García Frutos, FJ; García, S, 2010)	0.61
" This calls for information about their bioavailability and bioaccumulation potential."	( Bioaccumulation of 14C60 by the earthworm Eisenia fetida. Alvarez, PJ; Chen, C; Fortner, JD; Johnson, DR; Li, D; Li, Q, 2010)	0.36
" However, little is known about the bioavailability of PAHs bound to humin."	( Enhanced microbial degradation of humin-bound phenanthrene in a two-liquid-phase system. Hong, Q; Jiang, X; Kengara, FO; Song, Y; Wang, C; Wang, F; Wang, T; Zhang, Y, 2011)	0.63
"In the present study surfactant addition with the help of either a mechanical dispersion or a thermal treatment was applied in order to increase the solubility and the bioavailability of phenanthrene in aqueous media, and therefore to promote its biodegradation."	( Effect of surfactants, dispersion and temperature on solubility and biodegradation of phenanthrene in aqueous media. Blanchard, F; Boudrant, J; Delaunay, S; Goergen, JL; Guédon, E; Guseva, E; Pantsyrnaya, T, 2011)	0.78
" The net influence of SPS on the biodegradation and mineralization rates of PHE was dependent on its effects on compound bioavailability and bacteria population."	( Effects of suspended sediment on the biodegradation and mineralization of phenanthrene in river water. Jiang, G; Liu, T; Xia, X; Zhou, C; Zhou, Z, )	0.36
" Similar to black carbon (BC) particles, SWCNT have a high affinity for hydrophobic organic contaminants (HOCs) and therefore the presence of SWCNT in sediment may lead to altered bioavailability of HOCs."	( Influence of single-walled carbon nanotubes on microbial availability of phenanthrene in sediment. Chen, YX; Cui, XY; Gan, J; Jia, F, 2011)	0.6
" The most prominent effects on phenanthrene degradation kinetics were a five to fifteen fold increase in the linear growth term (k(2)) and a 23-27% increase in bioavailability factor S(0) for SW high and FW multi respectively."	( The effects of carbon sources and micronutrients in whey and fermented whey on the kinetics of phenanthrene biodegradation in diesel contaminated soil. Jonsson, AP; Östberg, TL, 2011)	0.87
"The present study was conducted to investigate the performance and feasibility of a self-dying reporter bacterium to visualize and quantify phenanthrene bioavailability in soil."	( Determination of phenanthrene bioavailability by using a self-dying reporter bacterium: test with model solids and soil. Nam, K; Shin, D, 2012)	0.92
" Correlation results for phenanthrene suggested that mild HPCD extraction was a better method to predict bioavailability of phenanthrene in soil compared with organic solvents extraction."	( Assessment of phenanthrene bioavailability in aged and unaged soils by mild extraction. Cheema, SA; Chen, X; Chen, Y; Khan, MI; Park, J; Shen, C; Shi, J; Tang, X; Zhang, C, 2012)	1.04
" However, the concentration-dependent and potential effects of CMs on the decrease in HOC bioavailability are not well understood."	( Influences of multiwalled carbon nanotubes and plant residue chars on bioaccumulation of polycyclic aromatic hydrocarbons by Chironomus plumosus larvae in sediment. Shen, M; Wang, F; Xia, X; Zhang, P; Zhao, X, 2012)	0.38
"Understanding the effects of aging time on the fraction distribution and bioavailability of PAH, such as phenanthrene (PHE) and pyrene (PYR), has considerable benefits for risk assessment, food security and remediation strategies for contaminated soil."	( The effects of aging time on the fraction distribution and bioavailability of PAH. Han, L; Hu, F; Li, H; Li, W; Ma, L; Xu, L; Zhang, J, 2012)	0.59
" A substantial range of soil properties was found, also for parameters which should be standardized because they have an important influence on the bioavailability of pollutants (e."	( Variability of standard artificial soils: Physico-chemical properties and phenanthrene desorption measured by means of supercritical fluid extraction. Bielská, L; Hofman, J; Hovorková, I; Komprdová, K, 2012)	0.61
" In addition to the various adverse effects that have been seen for different organisms, ENP are suspected to influence the transport, bioavailability and toxic properties of a range of environmental contaminants that may adsorb to their surface."	( The binding of phenanthrene to engineered silver and gold nanoparticles. Farkas, J; Nizzetto, L; Thomas, KV, 2012)	0.73
" In the present study, the authors investigated the microbial bioavailability of phenanthrene (PHE) sorbed on the original and demineralized humic acids (HAs) and humin (HM) that were sequentially extracted from a peat soil."	( Mechanisms regulating bioavailability of phenanthrene sorbed on a peat soil-origin humic substance. Shu, L; Tao, S; Wang, X; Xing, B; Yang, Y, 2012)	0.87
" Given their transport capacity and ubiquity, hyphae may substantially distribute remote hydrophobic contaminants in soil, thereby improving their bioavailability to bacterial degradation."	( Mycelia promote active transport and spatial dispersion of polycyclic aromatic hydrocarbons. Foss, S; Furuno, S; Harms, H; Jones, KC; Semple, KT; Wick, LY; Wild, E, 2012)	0.38
" It is proposed that the attached bacteria could possibly consume PHE on the humin via interactions between bacterial surfaces and humin, thereby overcoming the low PHE bioavailability and resulting in enhanced degradation."	( Enhanced desorption of humin-bound phenanthrene by attached phenanthrene-degrading bacteria. Bian, Y; Gu, C; Jiang, X; Kengara, FO; Wang, F; Zhang, Y; Zhao, Q, 2012)	0.66
"Carbon nanotubes have attracted attention around the world because of their high sorption capacity for hydrophobic organic compounds (HOCs); however, the bioavailability of HOCs sorbed on carbon nanotubes to bacteria is not well known."	( Mineralization of phenanthrene sorbed on multiwalled carbon nanotubes. Huang, J; Wang, R; Xia, N; Xia, X; Zhou, C, 2013)	0.72
"In this study, Mediterranean mussel species, Mytilus galloprovincialis, were exposed to phenanthrene (PHE) due to its ubiquitousness and bioavailability in the aquatic environment."	( Bioaccumulation-depuration kinetics and effects of phenanthrene on Mediterranean mussel (Mytilus galloprovincialis). Henkelmann, B; Okay, OS; Schramm, KW; Yakan, SD, 2013)	0.86
"Recent studies have suggested that the ability of a surfactant to enhance the bioavailability of hydrophobic organic compounds (HOC) requires the formation of surfactant hemi-micelles on the bacterial cell surface and subsequent partitioning of HOC into the hemi-micelles."	( Partitioning of phenanthrene into surfactant hemi-micelles on the bacterial cell surface and implications for surfactant-enhanced biodegradation. Brown, DG; Lanzon, JB, 2013)	0.74
"Efficient bioremediation of PAH-contaminated sites is limited by the hydrophobic character and poor bioavailability of pollutants."	( Identification of soil bacteria able to degrade phenanthrene bound to a hydrophobic sorbent in situ. Jouanneau, Y; Martin, F; Mbawala, A; Ngassoum, MB; Regonne, RK, 2013)	0.65
" Along with negligible effect of water addition after 4 weeks of incubation on kinetics of soil respiration, the soil moisture effect on xenobiotics mineralization indicates that most probably the bioavailability of NP and Phe increased due to bridging role of water films in soil."	( Effects of sterile storage, cation saturation and substrate additions on the degradability and extractability of nonylphenol and phenanthrene in soil. Marschner, B; Shchegolikhina, A, 2013)	0.59
" During enrichment on hydrocarbons, strain TG409(T) emulsified n-tetradecane and crude oil, and cells were found to be preferentially attached to oil droplets, indicating an ability by the strain to express cell surface amphiphilic substances (biosurfactants or bioemulsifiers) as a possible strategy to increase the bioavailability of hydrocarbons."	( Polycyclic aromatic hydrocarbon degradation of phytoplankton-associated Arenibacter spp. and description of Arenibacter algicola sp. nov., an aromatic hydrocarbon-degrading bacterium. Aitken, MD; Berry, D; Gutierrez, T; Mishamandani, S; Nichols, PD; Rhodes, G; Semple, KT; Whitman, WB, 2014)	0.4
" On the other hand, TX100 could effectively remove phenanthrene from contaminated soils treated by mixed surfactants, improving the bioavailability of organic pollutants."	( Utilizing surfactants to control the sorption, desorption, and biodegradation of phenanthrene in soil-water system. Jin, H; Zhou, W; Zhu, L, 2013)	0.87
" Our study investigated (i) the variability of ten artificial soils from different laboratories by means of the fate, extractability and bioavailability of phenanthrene and lindane, and (ii) the relationships of these results to soil properties and ageing."	( The variability of standard artificial soils: behaviour, extractability and bioavailability of organic pollutants. Hofman, J; Hovorková, I; Semple, KT, 2014)	0.6
"The potential bioavailability of phenanthrene aged in soil was determined by using a self-dying reporter bacterium, and the results were compared to two physicochemical measures, Tenax TA(®) bead-assisted desorption, and hydroxypropyl-β-cyclodextrin (HPCD) extraction."	( Potential use of a self-dying reporter bacterium to determine the bioavailability of aged phenanthrene in soil: comparison with physicochemical measures. Nam, K; Shin, D, 2014)	0.9
" The obtained results suggest that if surfactant-supplementation is to be used as an integral part of a bioremediation process, then possible bioavailability decrease due to entrapment of the contaminant into surfactant micelles should also be taken into consideration, as this phenomenon may have a negative impact on the biodegradation efficiency."	( Bioavailability of hydrocarbons to bacterial consortia during Triton X-100 mediated biodegradation in aqueous media. Chrzanowski, Ł; Lisiecki, P; Marecik, R; Pęziak, D; Piotrowska, A; Szulc, A; Woźniak, M; Ławniczak, Ł, 2013)	0.39
"Organic matter (OM) plays a vital role in controlling polycyclic aromatic hydrocarbon (PAH) bioavailability in soils and sediments."	( Hydroxypropyl-β-cyclodextrin extractability and bioavailability of phenanthrene in humin and humic acid fractions from different soils and sediments. Gao, H; Jia, L; Ma, J; Xu, L, 2014)	0.64
" Furthermore, under the combined conditions, the degradation of PAH increased with the biosurfactant concentration, and the soil DOM added system showed slightly higher degradation than the compost DOM added system, indicating that the chemical structure and composition of DOM would also affect the bioavailability of PAHs."	( Combined effects of DOM and biosurfactant enhanced biodegradation of polycylic armotic hydrocarbons (PAHs) in soil-water systems. Chen, W; Huang, GH; Wang, L; Xiao, H; Yu, H, 2014)	0.4
" These results may be explained by the lower sorption loss and reduced interfacial tension of mixed surfactants relative to Tween 80, which enhanced the bioavailability of PAHs in soil and the microbial degradation efficiency."	( Enhancing plant-microbe associated bioremediation of phenanthrene and pyrene contaminated soil by SDBS-Tween 80 mixed surfactants. Ni, H; Zhou, W; Zhu, L, 2014)	0.65
" The decline in bioavailability caused by aging on sorbed (14)C-pyrene was partially reversed by rhamnolipids, which enhanced mineralization of the aged compound, although not so efficiently like with the unaged chemical."	( Role of desorption kinetics in the rhamnolipid-enhanced biodegradation of polycyclic aromatic hydrocarbons. Congiu, E; Ortega-Calvo, JJ, 2014)	0.4
"Biochar is a carbon rich product from the incomplete combustion of biomass and it has been shown to reduce bioavailability of organic contaminants through adsorption."	( The impact of biochar on the bioaccessibility of (14)C-phenanthrene in aged soil. Adebisi, OO; Ogbonnaya, OU; Semple, KT, 2014)	0.65
" While the insignificant differences in PHE dissipation might be attributed to its higher solubility and availability under flooded condition that concealed the differences in improvement of bioavailability for microorganisms between rhizosphere and non-rhizosphere, and between both soils and both rice cultivars."	( Dissipation of phenanthrene and pyrene at the aerobic-anaerobic soil interface: differentiation induced by the rhizosphere of PAH-tolerant and PAH-sensitive rice (Oryza sativa L.) cultivars. He, Y; Li, X; Lin, J; Wu, J; Xia, W; Xu, J, 2015)	0.77
" These observations clearly suggested that βCD only served as the carrier to enhance the bioavailability of Phe rather than the co-substrate in the Phe biodegradation process."	( In silico understanding of the cyclodextrin-phenanthrene hybrid assemblies in both aqueous medium and bacterial membranes. Cao, Y; Gao, H; Jia, L; Ren, B, 2015)	0.68
"The present study investigated the effects of aqueous fullerene suspensions (nC60 ) on the bioavailability and toxicity of phenanthrene (Phe) to junior carp (Cyprinus carpio)."	( Fullerene-associated phenanthrene contributes to bioaccumulation but is not toxic to fish. Hu, X; Li, J; Shen, M; Yin, D, 2015)	0.94
" CCD may improve the bioavailability of phenanthrene and Pb in co-contaminated soil; CCD enhanced phytoremediation technology may be a good alternative for the removal of hydrophobic organic contaminants and heavy metals from contaminated soils."	( Cysteine-β-cyclodextrin enhanced phytoremediation of soil co-contaminated with phenanthrene and lead. Deng, N; Hu, S; Wang, G; Wang, Y; Wu, F, 2015)	0.91
" Despite this, our understanding of the exchangeability and potential bioavailability of PAHs associated with colloids is limited."	( Characterising the exchangeability of phenanthrene associated with naturally occurring soil colloids using an isotopic dilution technique. Donner, E; Juhasz, A; Lombi, E; Tavakkoli, E, 2015)	0.69
" The results showed that exposure to either PAHs induced similar levels of DNA strand breaks, although without a clear dose- or time-response, likely due to the low concentrations of exposure and potential shits in PAH bioavailability during the assays."	( Comparing the genotoxicity of a potentially carcinogenic and a noncarcinogenic PAH, singly, and in binary combination, on peripheral blood cells of the European sea bass. Costa, MH; Costa, PM; Ferreira, AM; Martins, M, 2016)	0.43
"Carbon nanotubes (CNTs) may affect bioavailability and toxicity of organic contaminants due to their adsorption properties."	( The influence of multiwalled carbon nanotubes on polycyclic aromatic hydrocarbon (PAH) bioavailability and toxicity to soil microbial communities in alfalfa rhizosphere. Acosta-Martinez, V; Anderson, TA; Cañas-Carrell, JE; Payton, P; Shrestha, B, 2015)	0.42
" PAHs bioavailability was time and species dependent and generally, phenanthrene uptake and translocation was faster than that of fluorene, probably due to their higher Kow."	( Fluorene and Phenanthrene Uptake and Accumulation by Wheat, Alfalfa and Sunflower from the Contaminated Soil. Deljoo, S; Harzandi, AM; Salehi-Lisar, SY, 2015)	1.02
" It is proposed that the bacterial-produced EPS was a key factor to mediate bacterial attachment to other surfaces and develop biofilms, thereby increasing the bioavailability of poorly soluble PAH for enhanced biodegradation."	( Extracellular polymeric substances govern the development of biofilm and mass transfer of polycyclic aromatic hydrocarbons for improved biodegradation. Jiang, X; Wang, F; Zeng, J; Zhang, Y; Zhao, Q; Zhu, X, 2015)	0.42
" Most microbes have limited practical applications because of the poor bioavailability of polycyclic aromatic hydrocarbons."	( Extractive biodegradation and bioavailability assessment of phenanthrene in the cloud point system by Sphingomonas polyaromaticivorans. Deng, T; Dong, W; Pan, T; Yu, S; Zeng, X, 2016)	0.68
"In this study, column leaching experiments were used to evaluate the leachability, distribution and bioavailability of phenanthrene and pyrene by root exudates from contaminated mangrove sediments."	( Effects of root exudates on the leachability, distribution, and bioavailability of phenanthrene and pyrene from mangrove sediments. Dai, M; Jia, H; Li, J; Liu, J; Lu, H; Yan, C, 2016)	0.87
"The bioavailability of organic contaminants adsorbed to carbon nanotubes (CNTs) remains unclear, especially in complex natural freshwaters containing natural organic matter (NOM)."	( Carbon Nanotube Properties Influence Adsorption of Phenanthrene and Subsequent Bioavailability and Toxicity to Pseudokirchneriella subcapitata. Altin, D; Booth, AM; Glomstad, B; Jenssen, BM; Liu, J; Sørensen, L, 2016)	0.69
"56), which indicated that ASE extraction techniques could not predict PAHs bioavailability to earthworms because it overestimated the risk of PAHs."	( [Aging Law of PAHs in Contaminated Soil and Their Enrichment in Earthworms Characterized by Chemical Extraction Techniques]. Bian, YR; Gu, CG; Jiang, X; Li, J; Liu, ZT; Wang, DZ; Yang, XL; Zhang, YN, 2015)	0.42
" A low content of soil organic matter (controlling bioavailability of phenanthrene to soil microorganisms) enhanced the combined effect of temperature and Phe toxicity, and a high biological activity of the soil (high NP values) increased the effect of high temperature on the Phe stimulatory influence."	( Influence of temperature on phenanthrene toxicity towards nitrifying bacteria in three soils with different properties. Klimkowicz-Pawlas, A; Maliszewska-Kordybach, B; Smreczak, B; Suszek-Łopatka, B, 2016)	0.96
" Simultaneously, fulvic acid and humic acid in the DOM enhanced phenanthrene bioavailability by increasing the solubility and mass transfer of phenanthrene, enhancing the uptake kinetics of Phe-1, and increasing the bacteria's direct access to DOM-associated phenanthrene."	( Effects of dissolved organic matter derived from forest leaf litter on biodegradation of phenanthrene in aqueous phase. Cai, D; Chao, Y; Morel, JL; Qiu, R; Wang, S; Yang, X, 2017)	0.92
" They play a pivotal role in the degradation of polycyclic aromatic hydrocarbons (PAHs) in sediments as they influence PAH bioavailability and degrader colonization."	( Response of low-molecular-weight organic acids in mangrove root exudates to exposure of polycyclic aromatic hydrocarbons. Jiang, S; Liu, J; Lu, H; Xie, F; Yan, C, 2017)	0.46
" survived in the rhizosphere and improved soil As bioavailability with co-exposure."	( Interactions between Pteris vittata L. genotypes and a polycyclic aromatic hydrocarbon (PAH)-degrading bacterium (Alcaligenes sp.) in arsenic uptake and PAH-dissipation. Liao, X; Sun, L; Yan, X; Zhu, G, 2017)	0.46
" The hypothesis of this study was that degradation of polycyclic aromatic hydrocarbons (PAHs) is enhanced if heavy metals in soil are immobilized and their bioavailability reduced."	( Investigations of microbial degradation of polycyclic aromatic hydrocarbons based on Friesl-Hanl, W; Jäger, A; Puschenreiter, M; Reichenauer, T; Soja, G; Watzinger, A; Wawra, A, 2018)	0.48
" A direct plant exposure assay in combination with an organic solvent extraction experiment was carried out in this study to investigate the bioavailability of polycyclic aromatic hydrocarbons (PAHs) with the application of pine needle biochars pyrolyzed under different temperatures (100, 300, 400, and 700 °C; referred as P100-P700 accordingly)."	( Reduced bioavailability and plant uptake of polycyclic aromatic hydrocarbons from soil slurry amended with biochars pyrolyzed under various temperatures. Chen, B; Wang, Y; Zhang, Y; Zhu, X, 2018)	0.48
"Given the sub-lethal risks of synthetic surfactants, rhamnolipid is a promising class of biosurfactants with the potential to promote the bioavailability of polycyclic aromatic hydrocarbons (PAHs), to provide a favorable substitute for synthetic surfactants."	( Rhamnolipid influences biosorption and biodegradation of phenanthrene by phenanthrene-degrading strain Pseudomonas sp. Ph6. Dick, RP; Gao, Y; Li, H; Ling, W; Liu, J; Ma, Z; Shen, D; Waigi, MG, 2018)	0.73
" LH-1 for the production of biodemulsifiers that enhance the bioavailability and solubilization of PAHs."	( Biodegradation of phenanthrene by biodemulsifier-producing strain Achromobacter sp. LH-1 and the study on its metabolisms and fermentation kinetics. Dai, Y; Hou, N; Jia, T; Li, C; Li, D; Luo, Z; Sun, Y; Wang, Q; Zhang, N, 2018)	0.81
" The reduced early developmental toxicity could be attributed to the decreased bioavailability and bioaccumulation of Phe by the low level of MPs."	( Low level of polystyrene microplastics decreases early developmental toxicity of phenanthrene on marine medaka (Oryzias melastigma). Li, Y; Lu, L; Ru, S; Tian, H; Wang, J; Wang, W; Yang, G; Zhang, Q; Zhang, X; Zheng, Y, 2020)	0.78
"Recent studies investigating the influence of carbon nanotubes (CNTs) on the bioavailability of organic contaminants have mostly focused on single-solute systems; however, a more likely scenario in the natural environment is a multisolute system where chemical interactions at the surface of the CNT may alter the bioavailability of these chemicals."	( Competitive Adsorption of Polycyclic Aromatic Hydrocarbons to Carbon Nanotubes and the Impact on Bioavailability to Fathead Minnow (Pimephales promelas). Karanfil, T; Lee, CM; Linard, EN; van den Hurk, P, 2020)	0.56
" Microplastics can adsorb hydrophobic organics, thus altering the bioavailability of PAHs and ultimately affecting the removal of PAHs from soil."	( The role of microplastics in the process of laccase-assisted phytoremediation of phenanthrene-contaminated soil. Chen, F; Chen, X; Guan, C; Ji, J; Li, Z; Wang, G; Zhang, X; Zhu, Y, 2023)	1.14
"Due to its large specific surface area and great hydrophobicity, microplastics can adsorb polycyclic aromatic hydrocarbons (PAHs), affecting the bioavailability and the toxicity of PAHs to plants."	( Microplastics reduced bioavailability and altered toxicity of phenanthrene to maize (Zea mays L.) through modulating rhizosphere microbial community and maize growth. Chen, X; Fu, W; Guan, C; Ji, J; Liu, A; Wang, G; Wang, W; Zheng, X, 2023)	1.15

Dosage Studied

This work investigated the binding behavior of phenanthrene by humic acids (HA-2 and HA-5), proteins (bovine serum albumin (BSA), lysozyme and pepsin), and their complexes using a passive dosing technique. The current study develops a new dual exposure system for the simultaneous and independent controllability of cytochrome P450 contents.

Excerpt	Relevance	Reference
" strain PYR-1 were dosed with anthracene or phenanthrene and after 14 days of incubation had degraded 92 and 90% of the added anthracene and phenanthrene, respectively."	( Degradation of phenanthrene and anthracene by cell suspensions of Mycobacterium sp. strain PYR-1. Cerniglia, CE; Doerge, DR; Freeman, JP; Moody, JD, 2001)	0.92
" One of the diastereoisomeric forms of the methyl ester of the mercapturic acid is identical with the ester of the mercapturic acid excreted by rats dosed with the epoxide or by rats and rabbits dosed with phenanthrene."	( METABOLISM OF POLYCYCLIC COMPOUNDS. THE METABOLISM OF 9,10-EPOXY-9,10-DIHYDROPHENANTHRENE IN RATS. BOYLAND, E; SIMS, P, 1965)	0.66
" Base on the method, dynamic relationships of dose-response for cytochrome P450 contents in earthworm and phenanthrene concentrations were conducted by contact filter paper and soil contaminated with phenanthrene."	( [Establishment of method for cytochrome P450 of earthworms (Eisenia fetida) as a biomarker]. Liu, M; Song, XY; Song, YF; Sun, TH; Zhang, W; Zhou, QX, 2006)	0.55
" As specific health effect mechanisms and dose-response are obscured bythe complex composition of DE, the linkage from exposure to internal dose can presumably be improved by use of specific biomarkers and metabolites in blood, breath, or urine."	( Identification of surrogate measures of diesel exhaust exposure in a controlled chamber study. Funk, WE; Hubbard, HF; Madden, MC; Pleil, JD; Rappaport, SM; Sobus, JR, 2008)	0.35
" Induction kinetics were calculated using a logistic-like model and approximate dose-response curves were designed."	( EROD activity in peripheral blood lymphocytes and 1-hydroxypyrene in urine and milk as biomarkers of PAH exposure in dairy ruminants. Chahin, A; Dziurla, MA; Guiavarc'h, YP; Jondreville, C; Rychen, G; Yen, FT, 2011)	0.37
" Although smokers are exposed to PAH by inhalation, oral dosing would be more practical for phenotyping studies."	( Metabolism of [D10]phenanthrene to tetraols in smokers for potential lung cancer susceptibility assessment: comparison of oral and inhalation routes of administration. Carmella, SG; Hatsukami, DK; Hecht, SS; Hochalter, JB; Jensen, J; Oliver, A; Rauch, D; Upadhyaya, P; Wang, J; Zhong, Y; Zimmerman, C, 2011)	0.7
" Thus far, there has been no ready explanation for a U-shaped dose-response curve, which is well recognized as a hormetic phenomenon for many hormones, drugs, and toxic compounds."	( Chronic exposure to phenanthrene influences the spermatogenesis of male Sebastiscus marmoratus: U-shaped effects and the reason for them. Chen, M; Chen, Y; Luo, H; Sun, L; Wang, C; Zhong, Y; Zuo, Z, 2011)	0.69
" To overcome these, a new experimental approach based on passive dosing is presented."	( Dynamic passive dosing for studying the biotransformation of hydrophobic organic chemicals: microbial degradation as an example. Karlson, UG; Mayer, P; Rein, A; Smith, KE; Trapp, S, 2012)	0.38
" To deliver well controlled exposure concentrations, a passive dosing system consisting of silicone coated vials and silicone O-rings was employed."	( A novel passive dosing system for determining the toxicity of phenanthrene to early life stages of zebrafish. Bragin, GE; Butler, JD; Cooper, KR; Lampi, MA; Letinski, DJ; Parkerton, TF, 2013)	0.63
"This work investigated the binding behavior of phenanthrene by humic acids (HA-2 and HA-5), proteins (bovine serum albumin (BSA)), lysozyme and pepsin), and their complexes using a passive dosing technique."	( Phenanthrene binding by humic acid-protein complexes as studied by passive dosing technique. Ghosh, S; Wang, Z; Xing, B; Zhao, J, 2014)	2.1
"Surfactant mediated exfoliation of multilayer graphene and its effects on phenanthrene adsorption were investigated using a passive dosing technique."	( Adsorption of phenanthrene on multilayer graphene as affected by surfactant and exfoliation. Wang, Z; Xing, B; Zhao, J; Zhao, Q, 2014)	0.99
" However, further studies are required for a better interpretation of the dose-response patterns observed."	( Oxidative stress and DNA damage responses to phenanthrene exposure in the estuarine guppy Poecilia vivipara. Bianchini, A; Cordeiro, GJ; Costa, PG; Hoff, ML; Klein, RD; Lencina Avila, JM; Machado, AA, 2014)	0.66
" Thus, the current study develops a new dual exposure system for the simultaneous and independent control of chemical and drought exposure in bioassays with terrestrial organisms: Passive dosing from silicone controlled the chemical activity of phenanthrene (chemical stress), while saline solutions controlled the water activity (drought stress) in the closed exposure system."	( Simultaneous control of phenanthrene and drought by dual exposure system: the degree of synergistic interactions in springtails was exposure dependent. Damgaard, C; Holmstrup, M; Mayer, P; Schmidt, SN, 2014)	0.89
" The higher remediation efficiency of low dosage SDBS-Tween 80 mixed surfactants thus advanced the technology of surfactant-enhanced plant-microbe associated bioremediation."	( Enhancing plant-microbe associated bioremediation of phenanthrene and pyrene contaminated soil by SDBS-Tween 80 mixed surfactants. Ni, H; Zhou, W; Zhu, L, 2014)	0.65
" To fill this gap, this study investigated the effect of predation on the bioaccumulation of polycyclic aromatic hydrocarbons (PAHs), one type of HOC, in low-to-high aquatic trophic levels under constant freely dissolved PAH concentrations (1, 5, or 10 μg L(-1)) maintained by passive dosing systems."	( How does predation affect the bioaccumulation of hydrophobic organic compounds in aquatic organisms? Li, H; Wang, H; Xia, X; Yang, Z; Zhang, X, 2015)	0.42
"06 and 60 μg/L groups gave a reasonable explanation for the nonmonotonic dose-response and also elucidated the action pathway via the brain-pituitary-gonadal axis."	( Reproductive and transgenerational toxicities of phenanthrene on female marine medaka (Oryzias melastigma). Chen, M; Chen, Y; Sun, L; Wang, C; Zuo, Z, 2015)	0.67
" Therefore, our objective was to improve exposure conditions in FET tests by evaluating a passive dosing format using silicone O-rings in standard 24-well polystyrene plates."	( A high throughput passive dosing format for the Fish Embryo Acute Toxicity test. Blust, R; Covaci, A; Knapen, D; Maho, W; Mayer, P; Schmidt, SN; Stinckens, E; Vergauwen, L, 2015)	0.42
"Adsorption and bioaccessibility of phenanthrene on graphite and multiwalled carbon nanotubes (CNTs) were investigated in simulated gastrointestinal fluid using a passive dosing system."	( Adsorption and bioaccessibility of phenanthrene on carbon nanotubes in the in vitro gastrointestinal system. Du, P; Li, W; Tao, S; Xing, B; Zhao, J; Zhao, Q; Zheng, H, 2016)	0.99
" All determined phenolic compounds in both leaves and roots at high dosage levels were enhanced compared to the uncontaminated plant."	( Response of phenolic metabolism to cadmium and phenanthrene and its influence on pollutant translocations in the mangrove plant Aegiceras corniculatum (L.) Blanco (Ac). Jiang, S; Liu, J; Liu, T; Lu, H; Su, Y; Weng, B; Yan, C, 2017)	0.71
" Conversely, glucocorticoids cause numerous unwanted side effects, particularly systemically dosed glucocorticoids."	( JTP-117968, a novel selective glucocorticoid receptor modulator, exhibits improved transrepression/transactivation dissociation. Bessho, Y; Deai, K; Hata, T; Kosugi, Y; Kurimoto, T; Matsushita, M; Misaki, S; Miyai, A; Nakagawa, T; Negoro, T; Tamai, I; Yamaguchi, T; Yamamoto, Y, 2017)	0.46
" Phe was supplied to L and H groups at the dosage of 180 mg/kg and 900 mg/kg orally at first day, and with the dose 90 mg/kg and 450 mg/kg by intraperitoneal injection at the last 2 days."	( Effects of phenanthrene on oxidative stress and inflammation in lung and liver of female rats. Guo, H; Hu, F; Li, C; Ma, H; Wang, D; Wang, H; Wang, J; Yao, Y; Zhang, H; Zhang, W, 2020)	0.95
" The results showed that increasing NaCas concentration and washing temperature improved the PHE mobilization, while high salinity and humic acid dosage displayed a negative effect."	( A pH-responsive phosphoprotein washing fluid for the removal of phenanthrene from contaminated peat moss in the cold region. An, C; Li, Q; Li, X; Qu, Z; Wan, S; Ye, Z; Yue, R; Zhang, P, 2023)	1.15
"Polycyclic aromatic hydrocarbon (PAH) contamination of industrial wasteland soils affects microbial diversity, but little is known about the dose-response effects of such contaminants on taxonomic and functional diversities of rhizospheric and plant endophytic bacteria."	( Taxonomic and functional responses of soil and root bacterial communities associated with poplar exposed to a contamination gradient of phenanthrene. Blaudez, D; Cébron, A; Fornasier, F; Gréau, L; Le Cordier, H, 2023)	1.11
" The extremely high sensitivity of accelerator mass spectrometry (AMS) allows for dosing humans with known carcinogens with de minimus risk."	( Impact of phenanthrene co-administration on the toxicokinetics of benzo[a]pyrene in humans. UPLC-accelerator mass spectrometry following oral microdosing. Anderson, KA; Labut, EM; Maier, MLV; Ognibene, TJ; Pennington, JM; Siddens, LK; Smith, JN; Tidwell, LG; Tilton, SC; Turteltaub, KW; Uesugi, SL; Vertel, EA; Williams, DE, 2023)	1.31

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

Role	Description
environmental contaminant	Any minor or unwanted substance introduced into the environment that can have undesired effects.
mouse metabolite	Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Class	Description
phenanthrenes	Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.
ortho-fused polycyclic arene
ortho-fused tricyclic hydrocarbon
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASE	Homo sapiens (human)	Potency	1.9953	0.0040	23.8416	100.0000	AID485290
Chain A, HADH2 protein	Homo sapiens (human)	Potency	39.8107	0.0251	20.2376	39.8107	AID893
Chain B, HADH2 protein	Homo sapiens (human)	Potency	39.8107	0.0251	20.2376	39.8107	AID893
Chain A, JmjC domain-containing histone demethylation protein 3A	Homo sapiens (human)	Potency	39.8107	0.6310	35.7641	100.0000	AID504339
Luciferase	Photinus pyralis (common eastern firefly)	Potency	45.5000	0.0072	15.7588	89.3584	AID1224835
interleukin 8	Homo sapiens (human)	Potency	74.9780	0.0473	49.4806	74.9780	AID651758
hypoxia-inducible factor 1 alpha subunit	Homo sapiens (human)	Potency	53.4655	3.1890	29.8841	59.4836	AID1224846
AR protein	Homo sapiens (human)	Potency	20.1029	0.0002	21.2231	8,912.5098	AID1259243; AID1259247
aldehyde dehydrogenase 1 family, member A1	Homo sapiens (human)	Potency	35.4813	0.0112	12.4002	100.0000	AID1030
thyroid stimulating hormone receptor	Homo sapiens (human)	Potency	1.0000	0.0013	18.0743	39.8107	AID926; AID938
nuclear receptor subfamily 1, group I, member 3	Homo sapiens (human)	Potency	43.0209	0.0010	22.6508	76.6163	AID1224838; AID1224839
retinoic acid nuclear receptor alpha variant 1	Homo sapiens (human)	Potency	24.1328	0.0030	41.6115	22,387.1992	AID1159552; AID1159555
retinoid X nuclear receptor alpha	Homo sapiens (human)	Potency	32.8016	0.0008	17.5051	59.3239	AID1159527; AID588546
estrogen-related nuclear receptor alpha	Homo sapiens (human)	Potency	30.4780	0.0015	30.6073	15,848.9004	AID1224848; AID1224849; AID1259403
farnesoid X nuclear receptor	Homo sapiens (human)	Potency	56.2341	0.3758	27.4851	61.6524	AID588526
pregnane X nuclear receptor	Homo sapiens (human)	Potency	52.9902	0.0054	28.0263	1,258.9301	AID1346982
estrogen nuclear receptor alpha	Homo sapiens (human)	Potency	0.1897	0.0002	29.3054	16,493.5996	AID743075
thyroid stimulating hormone receptor	Homo sapiens (human)	Potency	30.2182	0.0016	28.0151	77.1139	AID1224843
v-jun sarcoma virus 17 oncogene homolog (avian)	Homo sapiens (human)	Potency	53.4655	0.0578	21.1097	61.2679	AID1159526
chromobox protein homolog 1	Homo sapiens (human)	Potency	79.4328	0.0060	26.1688	89.1251	AID540317
potassium voltage-gated channel subfamily H member 2 isoform d	Homo sapiens (human)	Potency	28.1838	0.0178	9.6374	44.6684	AID588834
thyroid hormone receptor beta isoform 2	Rattus norvegicus (Norway rat)	Potency	68.6546	0.0003	23.4451	159.6830	AID743065; AID743067
nuclear factor erythroid 2-related factor 2 isoform 1	Homo sapiens (human)	Potency	74.9780	0.0006	27.2152	1,122.0200	AID651741
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Cytochrome P450 2A6	Homo sapiens (human)	IC50 (µMol)	97.0255	0.0044	3.8895	10.0000	AID241172; AID420671
Cytochrome P450 2A5	Mus musculus (house mouse)	IC50 (µMol)	26.0008	1.0000	4.2025	9.7051	AID241174; AID420670
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
xenobiotic metabolic process	Cytochrome P450 2A6	Homo sapiens (human)
steroid metabolic process	Cytochrome P450 2A6	Homo sapiens (human)
coumarin metabolic process	Cytochrome P450 2A6	Homo sapiens (human)
xenobiotic catabolic process	Cytochrome P450 2A6	Homo sapiens (human)
coumarin catabolic process	Cytochrome P450 2A6	Homo sapiens (human)
epoxygenase P450 pathway	Cytochrome P450 2A6	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
iron ion binding	Cytochrome P450 2A6	Homo sapiens (human)
coumarin 7-hydroxylase activity	Cytochrome P450 2A6	Homo sapiens (human)
enzyme binding	Cytochrome P450 2A6	Homo sapiens (human)
heme binding	Cytochrome P450 2A6	Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen	Cytochrome P450 2A6	Homo sapiens (human)
arachidonic acid epoxygenase activity	Cytochrome P450 2A6	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
endoplasmic reticulum membrane	Cytochrome P450 2A6	Homo sapiens (human)
cytoplasmic microtubule	Cytochrome P450 2A6	Homo sapiens (human)
intracellular membrane-bounded organelle	Cytochrome P450 2A6	Homo sapiens (human)
cytoplasm	Cytochrome P450 2A6	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Assay ID	Title	Year	Journal	Article
AID504812	Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1745845	Primary qHTS for Inhibitors of ATXN expression
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810	Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1347083	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1347082	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347086	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1331299	1-octanol/D2O distribution coefficient, log D of the compound at pH 7.4 by 1H NMR spectroscopic analysis
AID420670	Inhibition of mouse CYP2A5	2009	European journal of medicinal chemistry, May, Volume: 44, Issue:5	Exploring QSAR and QAAR for inhibitors of cytochrome P450 2A6 and 2A5 enzymes using GFA and G/PLS techniques.
AID603957	Octanol-water partition coefficient, log P of the compound	2008	European journal of medicinal chemistry, Apr, Volume: 43, Issue:4	QSPR modeling of octanol/water partition coefficient for vitamins by optimal descriptors calculated with SMILES.
AID767437	Cytotoxicity against human THP1 cells assessed as cell viability at 1 uM after 24 hrs by CCK-8 assay relative to untreated control	2013	European journal of medicinal chemistry, Sep, Volume: 67	Regioselective synthesis of phenanthrenes and evaluation of their anti-oxidant based anti-inflammatory potential.
AID241172	Inhibitory concentration against human cytochrome P450 2A6	2005	Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2	Quantitative structure-activity relationship analysis of inhibitors of the nicotine metabolizing CYP2A6 enzyme.
AID376047	Antifungal activity against Trichophyton rubrum C 113 by agar dilution method	1999	Journal of natural products, Oct, Volume: 62, Issue:10	In vitro evaluation of antifungal properties of phenylpropanoids and related compounds acting against dermatophytes.
AID420671	Inhibition of human CYP2A6	2009	European journal of medicinal chemistry, May, Volume: 44, Issue:5	Exploring QSAR and QAAR for inhibitors of cytochrome P450 2A6 and 2A5 enzymes using GFA and G/PLS techniques.
AID376046	Antifungal activity against Trichophyton mentagrophytes ATCC by agar dilution method	1999	Journal of natural products, Oct, Volume: 62, Issue:10	In vitro evaluation of antifungal properties of phenylpropanoids and related compounds acting against dermatophytes.
AID767447	Antioxidant activity assessed as DPPH free radical scavenging activity after 30 mins	2013	European journal of medicinal chemistry, Sep, Volume: 67	Regioselective synthesis of phenanthrenes and evaluation of their anti-oxidant based anti-inflammatory potential.
AID767443	Antiinflammatory activity in human THP1 cells assessed as inhibition of LPS-stimulated TNF-alpha release at 10 uM incubated for 1 hr prior to LPS challenge measured after 24 hrs by sandwich ELISA relative to untreated control	2013	European journal of medicinal chemistry, Sep, Volume: 67	Regioselective synthesis of phenanthrenes and evaluation of their anti-oxidant based anti-inflammatory potential.
AID767440	Cytotoxicity against human THP1 cells assessed as cell viability at 100 uM after 24 hrs by CCK-8 assay relative to untreated control	2013	European journal of medicinal chemistry, Sep, Volume: 67	Regioselective synthesis of phenanthrenes and evaluation of their anti-oxidant based anti-inflammatory potential.
AID767438	Cytotoxicity against human THP1 cells assessed as cell viability at 10 uM after 24 hrs by CCK-8 assay relative to untreated control	2013	European journal of medicinal chemistry, Sep, Volume: 67	Regioselective synthesis of phenanthrenes and evaluation of their anti-oxidant based anti-inflammatory potential.
AID767444	Antiinflammatory activity in human THP1 cells assessed as inhibition of LPS-stimulated TNF-alpha release at 50 uM incubated for 1 hr prior to LPS challenge measured after 24 hrs by sandwich ELISA relative to untreated control	2013	European journal of medicinal chemistry, Sep, Volume: 67	Regioselective synthesis of phenanthrenes and evaluation of their anti-oxidant based anti-inflammatory potential.
AID376055	Antifungal activity against Microsporum canis C 112 by agar dilution method	1999	Journal of natural products, Oct, Volume: 62, Issue:10	In vitro evaluation of antifungal properties of phenylpropanoids and related compounds acting against dermatophytes.
AID762061	Cytotoxicity against human HL60 cells after 24 hrs by WST-1 assay	2013	Bioorganic & medicinal chemistry letters, Aug-15, Volume: 23, Issue:16	Effect of the orthoquinone moiety in 9,10-phenanthrenequinone on its ability to induce apoptosis in HCT-116 and HL-60 cells.
AID1179091	Retention time of the compound in 75% MeOH by HPLC analysis	2014	Bioorganic & medicinal chemistry, Jul-15, Volume: 22, Issue:14	Sulfur, selenium and tellurium pseudopeptides: synthesis and biological evaluation.
AID376048	Antifungal activity against Epidermophyton floccosum C 114 by agar dilution method	1999	Journal of natural products, Oct, Volume: 62, Issue:10	In vitro evaluation of antifungal properties of phenylpropanoids and related compounds acting against dermatophytes.
AID376052	Antifungal activity against Aspergillus flavus ATCC 9170 by agar dilution method	1999	Journal of natural products, Oct, Volume: 62, Issue:10	In vitro evaluation of antifungal properties of phenylpropanoids and related compounds acting against dermatophytes.
AID767439	Cytotoxicity against human THP1 cells assessed as cell viability at 50 uM after 24 hrs by CCK-8 assay relative to untreated control	2013	European journal of medicinal chemistry, Sep, Volume: 67	Regioselective synthesis of phenanthrenes and evaluation of their anti-oxidant based anti-inflammatory potential.
AID1331301	n-Octanol/water partition coefficient, log P of the compound by HPLC method
AID767448	Antioxidant activity assessed as galvinoxyl free radical scavenging activity after 20 mins	2013	European journal of medicinal chemistry, Sep, Volume: 67	Regioselective synthesis of phenanthrenes and evaluation of their anti-oxidant based anti-inflammatory potential.
AID376051	Antifungal activity against Cryptococcus neoformans ATCC 32264 by agar dilution method	1999	Journal of natural products, Oct, Volume: 62, Issue:10	In vitro evaluation of antifungal properties of phenylpropanoids and related compounds acting against dermatophytes.
AID762062	Cytotoxicity against human HCT116 cells after 24 hrs by MTT assay	2013	Bioorganic & medicinal chemistry letters, Aug-15, Volume: 23, Issue:16	Effect of the orthoquinone moiety in 9,10-phenanthrenequinone on its ability to induce apoptosis in HCT-116 and HL-60 cells.
AID376050	Antifungal activity against Saccharomyces cerevisiae ATCC 9763 by agar dilution method	1999	Journal of natural products, Oct, Volume: 62, Issue:10	In vitro evaluation of antifungal properties of phenylpropanoids and related compounds acting against dermatophytes.
AID242975	Ratio of IC50 for human CYP2A6 to that of mouse CYP2A5 was determined	2005	Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2	Quantitative structure-activity relationship analysis of inhibitors of the nicotine metabolizing CYP2A6 enzyme.
AID376045	Antifungal activity against Microsporum gypseum C 115 by agar dilution method	1999	Journal of natural products, Oct, Volume: 62, Issue:10	In vitro evaluation of antifungal properties of phenylpropanoids and related compounds acting against dermatophytes.
AID376053	Antifungal activity against Aspergillus fumigatus ATCC 26934 by agar dilution method	1999	Journal of natural products, Oct, Volume: 62, Issue:10	In vitro evaluation of antifungal properties of phenylpropanoids and related compounds acting against dermatophytes.
AID1179092	Lipophilicity, log K of the compound by HPLC analysis	2014	Bioorganic & medicinal chemistry, Jul-15, Volume: 22, Issue:14	Sulfur, selenium and tellurium pseudopeptides: synthesis and biological evaluation.
AID376049	Antifungal activity against Candida albicans ATCC 10231 by agar dilution method	1999	Journal of natural products, Oct, Volume: 62, Issue:10	In vitro evaluation of antifungal properties of phenylpropanoids and related compounds acting against dermatophytes.
AID212400	Toxicity determined using Tadpole Narcosis Test	1991	Journal of medicinal chemistry, May, Volume: 34, Issue:5	Using theoretical descriptors in quantitative structure-activity relationships: some toxicological indices.
AID767445	Antiinflammatory activity in human THP1 cells assessed as inhibition of LPS-stimulated TNF-alpha release at 100 uM incubated for 1 hr prior to LPS challenge measured after 24 hrs by sandwich ELISA relative to untreated control	2013	European journal of medicinal chemistry, Sep, Volume: 67	Regioselective synthesis of phenanthrenes and evaluation of their anti-oxidant based anti-inflammatory potential.
AID767442	Antiinflammatory activity in human THP1 cells assessed as inhibition of LPS-stimulated TNF-alpha release at 1 uM incubated for 1 hr prior to LPS challenge measured after 24 hrs by sandwich ELISA relative to untreated control	2013	European journal of medicinal chemistry, Sep, Volume: 67	Regioselective synthesis of phenanthrenes and evaluation of their anti-oxidant based anti-inflammatory potential.
AID241174	Inhibitory concentration against mouse cytochrome P450 2A5	2005	Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2	Quantitative structure-activity relationship analysis of inhibitors of the nicotine metabolizing CYP2A6 enzyme.
AID767446	Antioxidant activity assessed as ABTS free radical scavenging activity after 1 min	2013	European journal of medicinal chemistry, Sep, Volume: 67	Regioselective synthesis of phenanthrenes and evaluation of their anti-oxidant based anti-inflammatory potential.
AID1331300	Lipophilicity, log D of the compound at pH 7.4 by HPLC method
AID376054	Antifungal activity against Aspergillus niger ATCC 9029 by agar dilution method	1999	Journal of natural products, Oct, Volume: 62, Issue:10	In vitro evaluation of antifungal properties of phenylpropanoids and related compounds acting against dermatophytes.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	169 (8.44)	18.7374
1990's	104 (5.19)	18.2507
2000's	654 (32.65)	29.6817
2010's	889 (44.38)	24.3611
2020's	187 (9.34)	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	4 (0.19%)	5.53%
Reviews	17 (0.82%)	6.00%
Case Studies	2 (0.10%)	4.05%
Observational	0 (0.00%)	0.25%
Other	2,039 (98.88%)	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
dinitrochlorobenzene Dinitrochlorobenzene: A skin irritant that may cause dermatitis of both primary and allergic types. Contact sensitization with DNCB has been used as a measure of cellular immunity. DNCB is also used as a reagent for the detection and determination of pyridine compounds.. 1-chloro-2,4-dinitrobenzene : A C-nitro compound that is chlorobenzene carrying a nitro substituent at each of the 2- and 4-positions.	2.02	1	0	C-nitro compound; monochlorobenzenes	allergen; epitope; sensitiser
ethylene dichloride ethylene dichloride: RN given refers to 1,2-isomer; structure given in first source. 1,2-dichloroethane : A member of the class of chloroethanes substituted by two chloro groups at positions 1 and 2.	3.5	2	0	chloroethanes	hepatotoxic agent; mutagen; non-polar solvent
1,2,4-trichlorobenzene 1,2,4-trichlorobenzene : A trichlorobenzene with chloro substituents at positions 1, 2 and 4.	4.37	6	0	trichlorobenzene
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.	2.7	3	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
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.	7.31	1	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
4-hydroxybenzoic acid 4-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring.	2.01	1	0	monohydroxybenzoic acid	algal metabolite; plant metabolite
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.	7.68	3	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.	2	1	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
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	9.37	6	0	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	3.22	5	0	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
benzaldehyde [no description available]	2.73	3	0	benzaldehydes	EC 3.1.1.3 (triacylglycerol lipase) inhibitor; EC 3.5.5.1 (nitrilase) inhibitor; flavouring agent; fragrance; odorant receptor agonist; plant metabolite
benzene [no description available]	6.24	26	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.	2.6	1	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.	3.48	2	0	benzyl alcohols	antioxidant; fragrance; metabolite; solvent
bromide Bromides: Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	7.47	2	0	halide anion; monoatomic bromine
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.	4.03	4	0	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
carbamates [no description available]	2.52	2	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.	4.37	6	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
catechol [no description available]	3.31	6	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).	5.06	39	0	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
citric acid, anhydrous Citric Acid: A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability.. citric acid : A tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms.	2.99	4	0	tricarboxylic acid	antimicrobial agent; chelator; food acidity regulator; fundamental metabolite
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	2.46	2	0	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
hydrochloric acid Hydrochloric Acid: A strong corrosive acid that is commonly used as a laboratory reagent. It is formed by dissolving hydrogen chloride in water. GASTRIC ACID is the hydrochloric acid component of GASTRIC JUICE.. hydrogen chloride : A mononuclear parent hydride consisting of covalently bonded hydrogen and chlorine atoms.	2.02	1	0	chlorine molecular entity; gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
coumarin 2H-chromen-2-one: coumarin derivative	2.48	2	0	coumarins	fluorescent dye; human metabolite; plant metabolite
2-cresol 2-cresol: RN given refers to parent cpd. o-cresol : A cresol that is phenol substituted by a methyl group at position 2. It is a minor urinary metabolite of toluene.	3.07	1	0	cresol	human xenobiotic 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).	3.86	11	0	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
3-cresol 3-cresol: RN given refers to parent cpd. m-cresol : A cresol with the methyl substituent at position 3. It is a minor urinary metabolite of toluene.	3.07	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.	2.04	1	0	alkane	xenobiotic
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	2.31	1	0	trihydroxybenzoic acid	antineoplastic agent; antioxidant; apoptosis inducer; astringent; cyclooxygenase 2 inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; geroprotector; human xenobiotic metabolite; plant metabolite
hydrogen sulfide Hydrogen Sulfide: A flammable, poisonous gas with a characteristic odor of rotten eggs. It is used in the manufacture of chemicals, in metallurgy, and as an analytical reagent. (From Merck Index, 11th ed). hydrogen sulfide : A sulfur hydride consisting of a single sulfur atom bonded to two hydrogen atoms. A highly poisonous, flammable gas with a characteristic odour of rotten eggs, it is often produced by bacterial decomposition of organic matter in the absence of oxygen.. thiol : An organosulfur compound in which a thiol group, -SH, is attached to a carbon atom of any aliphatic or aromatic moiety.	2.05	1	0	gas molecular entity; hydracid; mononuclear parent hydride; sulfur hydride	Escherichia coli metabolite; genotoxin; metabolite; signalling molecule; toxin; vasodilator agent
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.	3.89	12	0	guaiacols	disinfectant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; expectorant; plant metabolite
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.	2.08	1	0	2-hydroxydicarboxylic acid; C4-dicarboxylic acid	food acidity regulator; fundamental metabolite
propionaldehyde propionaldehyde: may cause respiratory irritation; RN given refers to parent cpd; structure. propanal : An aldehyde that consists of ethane bearing a formyl substituent. The parent of the class of propanals.	2	1	0	alpha-CH2-containing aldehyde; propanals	Escherichia coli metabolite
1-aminocyclopropane-1-carboxylic acid 1-aminocyclopropanecarboxylic acid : A non-proteinogenic alpha-amino acid consisting of cyclopropane having amino and carboxy substituents both at the 1-position.	2.05	1	0	amino acid zwitterion; monocarboxylic acid; non-proteinogenic alpha-amino acid	ethylene releasers; plant metabolite
dibenzofuran Dibenzofurans: Compounds that include the structure of dibenzofuran.. dibenzofurans : Any organic heterotricyclic compound based on a dibenzofuran skeleton and its substituted derivatives thereof.. dibenzofuran : A mancude organic heterotricyclic parent that consists of a furan ring flanked by two benzene rings ortho-fused across the 2,3- and 4,5-positions.	7.73	3	0	dibenzofurans; mancude organic heterotricyclic parent; polycyclic heteroarene	xenobiotic
cytosine [no description available]	1.96	1	0	aminopyrimidine; pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	2.36	2	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	2.92	4	0	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
glycine [no description available]	7.44	2	0	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical
histamine [no description available]	2.88	4	0	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.	7.8	3	0	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
imidazole imidazole: RN given refers to parent cpd. 1H-imidazole : An imidazole tautomer which has the migrating hydrogen at position 1.	7.07	1	0	imidazole
indole [no description available]	2.72	3	0	indole; polycyclic heteroarene	Escherichia coli metabolite
iodine Iodine: A nonmetallic element of the halogen group that is represented by the atomic symbol I, atomic number 53, and atomic weight of 126.90. It is a nutritionally essential element, especially important in thyroid hormone synthesis. In solution, it has anti-infective properties and is used topically.. diiodine : Molecule comprising two covalently bonded iodine atoms with overall zero charge..	2.06	1	0	diatomic iodine	nutrient
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.	9.67	9	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
croton oil [no description available]	2.85	1	0	N-acyl-hexosamine
acetanilide acetanilide: a phenylacetamide; use ACETANILIDES for the plural group meaning of the singular term. N-phenylacetamide : A member of the class of acetamides that is acetamide in which one of the hydrogens attached to the nitrogen is substituted by a phenyl group.	2.1	1	0	acetamides; anilide	analgesic
naphthalene [no description available]	10.92	212	1	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.	4.23	5	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.	2.49	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
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	3.92	12	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
nitrites Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)	3.16	5	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.	7.11	1	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
1-octanol 1-Octanol: A colorless, slightly viscous liquid used as a defoaming or wetting agent. It is also used as a solvent for protective coatings, waxes, and oils, and as a raw material for plasticizers. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). octan-1-ol : An octanol carrying the hydroxy group at position 1.	3.07	1	0	octanol; primary alcohol	antifungal agent; bacterial metabolite; fuel additive; kairomone; plant 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.	2.04	1	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.	2.48	2	0	alpha,omega-dicarboxylic acid	algal metabolite; human metabolite; plant metabolite
4-aminobenzoic acid 4-Aminobenzoic Acid: An aminobenzoic acid isomer that combines with pteridine and GLUTAMIC ACID to form FOLIC ACID. The fact that 4-aminobenzoic acid absorbs light throughout the UVB range has also resulted in its use as an ingredient in SUNSCREENS.. 4-ammoniobenzoate : A zwitterion obtained by transfer of a proton from the carboxy to the amino group of 4-aminobenzoic acid.. 4-aminobenzoic acid : An aminobenzoic acid in which the amino group is para to the carboxy group.	2.04	1	0	aminobenzoic acid; aromatic amino-acid zwitterion	allergen; Escherichia coli metabolite; plant metabolite
4-nitrophenol 4-nitrophenol: RN given refers to parent cpd. mononitrophenol : A nitrophenol that is phenol carrying a single nitro substituent at unspecified position.. 4-nitrophenol : A member of the class of 4-nitrophenols that is phenol in which the hydrogen that is para to the hydroxy group has been replaced by a nitro group.	3.07	1	0	4-nitrophenols	human xenobiotic metabolite; mouse metabolite
parathion [no description available]	3.1	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	3.94	12	0	aromatic fungicide; chlorophenol; organochlorine pesticide; pentachlorobenzenes	human xenobiotic metabolite
phenol [no description available]	5.08	13	0	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
phenethylamine phenethylamine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7016. 2-phenylethylamine : A phenylethylamine having the phenyl substituent at the 2-position.	2.02	1	0	alkaloid; aralkylamine; phenylethylamine	Escherichia coli metabolite; human metabolite; mouse metabolite
phthalic acid phthalic acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7178. phthalic acid : A benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions.	8.73	10	0	benzenedicarboxylic acid	human xenobiotic metabolite
porphobilinogen [no description available]	3.54	2	0	aralkylamino compound; dicarboxylic acid; pyrroles	Escherichia coli metabolite; metabolite; mouse metabolite
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.	3.07	1	0	propan-1-ols; short-chain primary fatty alcohol	metabolite; protic solvent
pyridine azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.	3.81	3	0	azaarene; mancude organic heteromonocyclic parent; monocyclic heteroarene; pyridines	environmental contaminant; NMR chemical shift reference compound
pyridoxine 4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol: structure in first source. vitamin B6 : Any member of the group of pyridines that exhibit biological activity against vitamin B6 deficiency. Vitamin B6 deficiency is associated with microcytic anemia, electroencephalographic abnormalities, dermatitis with cheilosis (scaling on the lips and cracks at the corners of the mouth) and glossitis (swollen tongue), depression and confusion, and weakened immune function. Vitamin B6 consists of the vitamers pyridoxine, pyridoxal, and pyridoxamine and their respective 5'-phosphate esters (and includes their corresponding ionized and salt forms).	2.44	2	0	hydroxymethylpyridine; methylpyridines; monohydroxypyridine; vitamin B6	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
pyruvic acid Pyruvic Acid: An intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed). pyruvic acid : A 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis.	2.71	3	0	2-oxo monocarboxylic acid	cofactor; fundamental metabolite
dimethyl sulfide dimethyl sulfide: structure. dimethyl sulfide : A methyl sulfide in which the sulfur atom is substituted by two methyl groups. It is produced naturally by some marine algae.. methyl sulfide : Any aliphatic sulfide in which at least one of the organyl groups attached to the sulfur is a methyl group.	2.04	1	0	aliphatic sulfide	algal metabolite; bacterial xenobiotic metabolite; EC 3.5.1.4 (amidase) inhibitor; Escherichia coli metabolite; marine metabolite
sulfuric acid sulfuric acid : A sulfur oxoacid that consists of two oxo and two hydroxy groups joined covalently to a central sulfur atom.	7.17	1	0	sulfur oxoacid	catalyst
taurine [no description available]	7.15	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.	2.47	2	0	primary alcohol; vitamin B1	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	10.52	12	0	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
catechin [no description available]	2.08	1	0	hydroxyflavan
1,10-phenanthroline 1,10-phenanthroline: RN given refers to parent cpd; inhibits Zn-dependent metalloproteinases	3.34	7	0	phenanthroline	EC 2.7.1.1 (hexokinase) inhibitor; EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor
1-aminobenzotriazole [no description available]	2.42	2	0
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	2.48	2	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
2,2'-dipyridyl 2,2'-Dipyridyl: A reagent used for the determination of iron.. 2,2'-bipyridine : A bipyridine in which the two pyridine moieties are linked by a bond between positions C-2 and C-2'.	2.67	3	0	bipyridine	chelator; ferroptosis inhibitor
2,4,6-tribromophenol [no description available]	2.05	1	0	bromophenol	environmental contaminant; fungicide; marine metabolite
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.	2.05	1	0	chlorophenoxyacetic acid; dichlorobenzene	agrochemical; defoliant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; environmental contaminant; phenoxy herbicide; synthetic auxin
2,4-dinitrophenol 2,4-Dinitrophenol: A toxic dye, chemically related to trinitrophenol (picric acid), used in biochemical studies of oxidative processes where it uncouples oxidative phosphorylation. It is also used as a metabolic stimulant. (Stedman, 26th ed). dinitrophenol : Members of the class of nitrophenol carrying two nitro substituents.. 2,4-dinitrophenol : A dinitrophenol having the nitro groups at the 2- and 4-positions.	2.45	2	0	dinitrophenol	allergen; antiseptic drug; bacterial xenobiotic metabolite; geroprotector; oxidative phosphorylation inhibitor
3-methylcholanthrene Methylcholanthrene: A carcinogen that is often used in experimental cancer studies.. 3-methylcholanthrene : A pentacyclic ortho- and peri-fused polycyclic arene consisting of a dihydrocyclopenta[ij]tetraphene ring system with a methyl substituent at the 3-position.	5.67	10	0	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
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.	2.48	2	0	phenols	environmental contaminant
phenanthridone phenanthridone: coal tar derivative; structure given in first source. phenanthridone : A member of the class of phenanthridines that is phenanthridine with an oxo substituent at position 6. A poly(ADP-ribose) polymerase (PARP) inhibitor, it has been shown to exhibit immunosuppressive activity.	7.46	2	0	lactam; phenanthridines	EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor; immunosuppressive agent; mutagen
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.	2.04	1	0	benzoic acids; phenyl acetates; salicylates	anticoagulant; antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; EC 1.1.1.188 (prostaglandin-F synthase) inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; plant activator; platelet aggregation inhibitor; prostaglandin antagonist; teratogenic agent
atrazine [no description available]	4.19	16	0	chloro-1,3,5-triazine; diamino-1,3,5-triazine	environmental contaminant; herbicide; xenobiotic
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.	9.62	111	0	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
beta-naphthoflavone beta-Naphthoflavone: A polyaromatic hydrocarbon inducer of P4501A1 and P4501A2 cytochromes. (Proc Soc Exp Biol Med 1994 Dec:207(3):302-308). beta-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the f side of flavone.	3.09	5	0	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist
cacodylic acid dimethylarsinic acid : The organoarsenic compound that is arsenic acid substituted on the central arsenic atom with two methyl groups.	2.13	1	0	organoarsenic compound	xenobiotic metabolite
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.	7.08	1	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
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.	2.98	4	0	quaternary ammonium ion
cetylpyridinium Cetylpyridinium: Cationic bactericidal surfactant used as a topical antiseptic for skin, wounds, mucous membranes, instruments, etc.; and also as a component in mouthwash and lozenges.	7.1	1	0	pyridinium ion
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.	9.1	4	0	chloropyridine; organic thiophosphate	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; environmental contaminant; insecticide; xenobiotic
chlorzoxazone Chlorzoxazone: A centrally acting central muscle relaxant with sedative properties. It is claimed to inhibit muscle spasm by exerting an effect primarily at the level of the spinal cord and subcortical areas of the brain. (From Martindale, The Extra Pharmacopoea, 30th ed, p1202). chlorzoxazone : A member of the class of 1,3-benzoxazoles that is 1,3-benzoxazol-2-ol in which the hydrogen atom at position 5 is substituted by chlorine. A centrally acting muscle relaxant with sedative properties, it is used for the symptomatic treatment of painful muscle spasm.	1.99	1	0	1,3-benzoxazoles; heteroaryl hydroxy compound; organochlorine compound	muscle relaxant; sedative
ciprofloxacin Ciprofloxacin: A broad-spectrum antimicrobial carboxyfluoroquinoline.. ciprofloxacin : A quinolone that is quinolin-4(1H)-one bearing cyclopropyl, carboxylic acid, fluoro and piperazin-1-yl substituents at positions 1, 3, 6 and 7, respectively.	2.82	2	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
clioquinol Clioquinol: A potentially neurotoxic 8-hydroxyquinoline derivative long used as a topical anti-infective, intestinal antiamebic, and vaginal trichomonacide. The oral preparation has been shown to cause subacute myelo-optic neuropathy and has been banned worldwide.. 5-chloro-7-iodoquinolin-8-ol : A monohydroxyquinoline that is quinolin-8-ol in which the hydrogens at positions 5 and 7 are replaced by chlorine and iodine, respectively. It has antibacterial and atifungal properties, and is used in creams for the treatment of skin infections. It has also been investigated as a chelator of copper and zinc ions for the possible treatment of Alzheimer's disease.	1.93	1	0	monohydroxyquinoline; organochlorine compound; organoiodine compound	antibacterial agent; antifungal agent; antimicrobial agent; antineoplastic agent; antiprotozoal drug; chelator; copper chelator
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.	2.45	2	0	cresol	Escherichia coli metabolite; human metabolite; uremic toxin
amphetamine Amphetamine: A powerful central nervous system stimulant and sympathomimetic. Amphetamine has multiple mechanisms of action including blocking uptake of adrenergics and dopamine, stimulation of release of monamines, and inhibiting monoamine oxidase. Amphetamine is also a drug of abuse and a psychotomimetic. The l- and the d,l-forms are included here. The l-form has less central nervous system activity but stronger cardiovascular effects. The d-form is DEXTROAMPHETAMINE.. 1-phenylpropan-2-amine : A primary amine that is isopropylamine in which a hydrogen attached to one of the methyl groups has been replaced by a phenyl group.. amphetamine : A racemate comprising equimolar amounts of (R)-amphetamine (also known as levamphetamine or levoamphetamine) and (S)-amphetamine (also known as dexamfetamine or dextroamphetamine.	2.02	1	0	primary amine
diazepam Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.	1.99	1	0	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; xenobiotic
dibenzothiophene dibenzothiophene : A mancude organic heterotricyclic parent that consists of a thiophene ring flanked by two benzene rings ortho-fused across the 2,3- and 4,5-positions.	8.12	5	0	dibenzothiophenes; mancude organic heterotricyclic parent	keratolytic drug
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.	2.97	4	0	diester; phthalate ester	EC 3.2.1.20 (alpha-glucosidase) inhibitor; environmental contaminant; metabolite; plasticiser; teratogenic agent
diclofenac Diclofenac: A non-steroidal anti-inflammatory agent (NSAID) with antipyretic and analgesic actions. It is primarily available as the sodium salt.. diclofenac : A monocarboxylic acid consisting of phenylacetic acid having a (2,6-dichlorophenyl)amino group at the 2-position.	2	1	0	amino acid; aromatic amine; dichlorobenzene; monocarboxylic acid; secondary amino compound	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
dichlorodiphenyl dichloroethylene Dichlorodiphenyl Dichloroethylene: An organochlorine pesticide, it is the ethylene metabolite of DDT.	2.04	1	0	chlorophenylethylene; monochlorobenzenes	human xenobiotic metabolite; persistent organic pollutant
ddt 1,1-bis(p-chlorophenyl)-2,2,2-trichloroethane: structure in first source	3	4	0	benzenoid aromatic compound; chlorophenylethane; monochlorobenzenes; organochlorine insecticide	bridged diphenyl acaricide; carcinogenic agent; endocrine disruptor; persistent organic pollutant
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.	2.74	3	0	3-(3,4-substituted-phenyl)-1,1-dimethylurea; dichlorobenzene	environmental contaminant; mitochondrial respiratory-chain inhibitor; photosystem-II inhibitor; urea herbicide; xenobiotic
2,3-dimethoxy-1,4-naphthoquinone 2,3-dimethoxynaphthalene-1,4-dione : A naphthoquinone that is 1,4-naphthoquinone bearing two methoxy substituents at positions 2 and 3. Redox-cycling agent that induces intracellular superoxide anion formation and, depending on the concentration, induces cell proliferation, apoptosis or necrosis. Used to study the role of ROS in cell toxicity, apoptosis, and necrosis.	2.04	1	0	1,4-naphthoquinones
endosulfan Endosulfan: A polychlorinated compound used for controlling a variety of insects. It is practically water-insoluble, but readily adheres to clay particles and persists in soil and water for several years. Its mode of action involves repetitive nerve-discharges positively correlated to increase in temperature. This compound is extremely toxic to most fish. (From Comp Biochem Physiol (C) 1993 Jul;105(3):347-61). endosulfan : A cyclic sulfite ester that is 1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxathiepine 3-oxide substituted by chloro groups at positions 6, 7, 8, 9, 10 and 10.	2.57	2	0	cyclic sulfite ester; cyclodiene organochlorine insecticide	acaricide; agrochemical; GABA-gated chloride channel antagonist; persistent organic pollutant
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.	3.07	1	0	ether; volatile organic compound	inhalation anaesthetic; non-polar solvent; refrigerant
glutaral Glutaral: One of the protein CROSS-LINKING REAGENTS that is used as a disinfectant for sterilization of heat-sensitive equipment and as a laboratory reagent, especially as a fixative.. glutaraldehyde : A dialdehyde comprised of pentane with aldehyde functions at C-1 and C-5.	2.06	1	0	dialdehyde	cross-linking reagent; disinfectant; fixative
guanidine Guanidine: A strong organic base existing primarily as guanidium ions at physiological pH. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed) It is also used in the treatment of myasthenia and as a fluorescent probe in HPLC.. guanidine : An aminocarboxamidine, the parent compound of the guanidines.	6.92	1	0	carboxamidine; guanidines; one-carbon compound
heptachlor Heptachlor: A man-made compound previously used to control termites and other insects. Even though production of heptachlor was phased out of use in the United States during the late 1980's it remains in soil and hazardous waste sites. It is clearly toxic to animals and humans but, the International Agency for Research on Cancer (IARC) has determined that heptachlor is not classifiable as to its carcinogenicity to humans. (From ATSDR Public Heath Statement, April 1989). heptachlor : A cyclodiene organochlorine insecticide that is 3a,4,7,7a-tetrahydro-1H-4,7-methanoindene substituted by chlorine atoms at positions 1, 4, 5, 6, 7, 8 and 8. Formerly used to kill termites, ants and other insects in agricultural and domestic situations.	2.15	1	0	cyclodiene organochlorine insecticide	agrochemical; antibacterial agent; antifungal agent; GABA-gated chloride channel antagonist; persistent organic pollutant
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.	3.07	1	0	secondary alcohol; secondary fatty alcohol	protic solvent
ketoconazole 1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine : A dioxolane that is 1,3-dioxolane which is substituted at positions 2, 2, and 4 by imidazol-1-ylmethyl, 2,4-dichlorophenyl, and [para-(4-acetylpiperazin-1-yl)phenoxy]methyl groups, respectively.	2.41	2	0	dichlorobenzene; dioxolane; ether; imidazoles; N-acylpiperazine; N-arylpiperazine
malathion Malathion: A wide spectrum aliphatic organophosphate insecticide widely used for both domestic and commercial agricultural purposes.. malathion : A racemate comprising equimolar amounts of (R) and (S)-malathion. It is a broad spectrum organophosphate proinsecticide used to control a wide range of pests including Coleoptera, Diptera, fruit flies, mosquitos and spider mites.. diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate : A diester that is diethyl succinate in which position 2 is substituted by a (dimethoxyphosphorothioyl)thio group.	7.31	1	0	diester; ethyl ester; organic thiophosphate
vitamin k 3 Vitamin K 3: A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo.	2.04	1	0	1,4-naphthoquinones; vitamin K	angiogenesis inhibitor; antineoplastic agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; human urinary metabolite; nutraceutical
methoxychlor Methoxychlor: An insecticide. Methoxychlor has estrogenic effects in mammals, among other effects.	2.25	1	0	organochlorine insecticide
methyl parathion Methyl Parathion: The methyl homolog of parathion. An effective, but highly toxic, organothiophosphate insecticide and cholinesterase inhibitor.. parathion-methyl : A C-nitro compound that is 4-nitrophenol substituted by a (dimethoxyphosphorothioyl)oxy group at position 4.	2.04	1	0	C-nitro compound; organic thiophosphate; organothiophosphate insecticide	acaricide; agrochemical; antifungal agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; environmental contaminant; genotoxin
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.	2.02	1	0	aromatic amide; benzenes; ether; organochlorine compound
metyrapone Metyrapone: An inhibitor of the enzyme STEROID 11-BETA-MONOOXYGENASE. It is used as a test of the feedback hypothalamic-pituitary mechanism in the diagnosis of CUSHING SYNDROME.. metyrapone : An aromatic ketone that is 3,3-dimethylbutan-2-one in which the methyl groups at positions 1 and 4 are replaced by pyridin-3-yl groups. A steroid 11beta-monooxygenase (EC 1.14.15.4) inhibitor, it is used in the diagnosis of adrenal insufficiency.	2.01	1	0	aromatic ketone	antimetabolite; diagnostic agent; EC 1.14.15.4 (steroid 11beta-monooxygenase) inhibitor
myristicin myristicin: asaricin is an isomer; structure; a methylene dioxy version of elemicin;	2	1	0	organic molecular entity	metabolite
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.	2.63	2	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.	7.87	3	0	3-oxo monocarboxylic acid; N-arylpiperazine; N-methylpiperazine; organofluorine compound; oxazinoquinoline
oxybenzone oxybenzone : A hydroxybenzophenone that is benzophenone which is substituted at the 2- and 4-positions of one of the benzene rings by hydroxy and methoxy groups respectively.	2.03	1	0	hydroxybenzophenone; monomethoxybenzene	dermatologic drug; environmental contaminant; protective agent; ultraviolet filter; xenobiotic
quinone benzoquinone : The simplest members of the class of benzoquinones, consisting of cyclohexadiene which is substituted by two oxo groups.. 1,4-benzoquinone : The simplest member of the class of 1,4-benzoquinones, obtained by the formal oxidation of hydroquinone to the corresponding diketone. It is a metabolite of benzene.. quinone : Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included).	2.34	2	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.	7.47	2	0	monochlorophenol
4-dichlorobenzene dichlorobenzene : Any member of the class of chlorobenzenes carrying two chloro groups at unspecified positions.. 1,4-dichlorobenzene : A dichlorobenzene carrying chloro groups at positions 1 and 4.	2.96	4	0	dichlorobenzene	insecticide
phenacetin Saridon: contains phenacetin, caffeine, propyphenazone & pyrithyldione	1.99	1	0	acetamides; aromatic ether	cyclooxygenase 3 inhibitor; non-narcotic analgesic; peripheral nervous system drug
phenobarbital Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.	1.97	1	0	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
potassium chloride Potassium Chloride: A white crystal or crystalline powder used in BUFFERS; FERTILIZERS; and EXPLOSIVES. It can be used to replenish ELECTROLYTES and restore WATER-ELECTROLYTE BALANCE in treating HYPOKALEMIA.. potassium chloride : A metal chloride salt with a K(+) counterion.	2.11	1	0	inorganic chloride; inorganic potassium salt; potassium salt	fertilizer
proadifen Proadifen: An inhibitor of drug metabolism and CYTOCHROME P-450 ENZYME SYSTEM activity.	2.01	1	0	diarylmethane
procaine Procaine: A local anesthetic of the ester type that has a slow onset and a short duration of action. It is mainly used for infiltration anesthesia, peripheral nerve block, and spinal block. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1016).. procaine : A benzoate ester, formally the result of esterification of 4-aminobenzoic acid with 2-diethylaminoethanol but formed experimentally by reaction of ethyl 4-aminobenzoate with 2-diethylaminoethanol.	2.04	1	0	benzoate ester; substituted aniline; tertiary amino compound	central nervous system depressant; drug allergen; local anaesthetic; peripheral nervous system drug
rolipram [no description available]	2.01	1	0	pyrrolidin-2-ones	antidepressant; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor
spiperone Spiperone: A spiro butyrophenone analog similar to HALOPERIDOL and other related compounds. It has been recommended in the treatment of SCHIZOPHRENIA.. spiperone : An azaspiro compound that is 1,3,8-triazaspiro[4.5]decane which is substituted at positions 1, 4, and 8 by phenyl, oxo, and 4-(p-fluorophenyl)-4-oxobutyl groups, respectively.	1.97	1	0	aromatic ketone; azaspiro compound; organofluorine compound; piperidines; tertiary amino compound	alpha-adrenergic antagonist; antipsychotic agent; dopaminergic antagonist; psychotropic drug; serotonergic antagonist
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.	2.55	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
2,4-thiazolidinedione thiazolidine-2,4-dione: structure in first source. 1,3-thiazolidine-2,4-dione : A thiazolidenedione carrying oxo substituents at positions 2 and 4.	2.31	1	0	thiazolidenedione
tolbutamide Tolbutamide: A sulphonylurea hypoglycemic agent with actions and uses similar to those of CHLORPROPAMIDE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p290). tolbutamide : An N-sulfonylurea that consists of 1-butylurea having a tosyl group attached at the 3-position.	2	1	0	N-sulfonylurea	human metabolite; hypoglycemic agent; insulin secretagogue; potassium channel blocker
triclosan [no description available]	2.79	3	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
alloxan Alloxan: Acidic compound formed by oxidation of URIC ACID. It is isolated as an efflorescent crystalline hydrate.. alloxan : A member of the class of pyrimidones, the structure of which is that of perhydropyrimidine substituted at C-2, -4, -5 and -6 by oxo groups.	6.93	1	0	pyrimidone	hyperglycemic agent; metabolite
piperonyl butoxide [no description available]	2.71	3	0	benzodioxoles	pesticide synergist
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.	3.8	1	1	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.	1.93	1	0	17-oxo steroid; 3-hydroxy steroid; phenolic steroid; phenols	antineoplastic agent; bone density conservation agent; estrogen; human metabolite; mouse metabolite
1,2,5,6-dibenzanthracene 1,2,5,6-dibenzanthracene: RN given refers to parent cpd	2.71	3	0	ortho-fused polycyclic arene	mutagen
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.	1.93	1	0	2-acetamidofluorenes	antimitotic; carcinogenic agent; epitope; mutagen
triiodothyronine Triiodothyronine: A T3 thyroid hormone normally synthesized and secreted by the thyroid gland in much smaller quantities than thyroxine (T4). Most T3 is derived from peripheral monodeiodination of T4 at the 5' position of the outer ring of the iodothyronine nucleus. The hormone finally delivered and used by the tissues is mainly T3.. 3,3',5-triiodo-L-thyronine : An iodothyronine compound having iodo substituents at the 3-, 3'- and 5-positions. Although some is produced in the thyroid, most of the 3,3',5-triiodo-L-thyronine in the body is generated by mono-deiodination of L-thyroxine in the peripheral tissues. Its metabolic activity is about 3 to 5 times that of L-thyroxine. The sodium salt is used in the treatment of hypothyroidism.	3.8	1	1	2-halophenol; amino acid zwitterion; iodophenol; iodothyronine	human metabolite; mouse metabolite; thyroid hormone
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.	2.33	2	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.	3.5	2	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
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.	6.87	20	0	ortho-fused polycyclic arene; tetraphenes
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	2.17	1	0	C-nitro compound; carboxamide; diol; organochlorine compound	antibacterial drug; antimicrobial agent; Escherichia coli metabolite; geroprotector; Mycoplasma genitalium metabolite; protein synthesis inhibitor
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.	2.05	1	0	pseudohalide anion	EC 1.9.3.1 (cytochrome c oxidase) inhibitor
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.	2.98	4	0	17-hydroxy steroid; 3-hydroxy steroid; terminal acetylenic compound	xenoestrogen
9,10-dimethyl-1,2-benzanthracene 9,10-Dimethyl-1,2-benzanthracene: Polycyclic aromatic hydrocarbon found in tobacco smoke that is a potent carcinogen.. 7,12-dimethyltetraphene : A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.	5.08	5	0	ortho-fused polycyclic arene; tetraphenes	carcinogenic agent
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	2.06	1	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.	3.01	4	0	tetrachlorophenol	xenobiotic metabolite
uridine [no description available]	2.06	1	0	uridines	drug metabolite; fundamental metabolite; human metabolite
bromodeoxyuridine Bromodeoxyuridine: A nucleoside that substitutes for thymidine in DNA and thus acts as an antimetabolite. It causes breaks in chromosomes and has been proposed as an antiviral and antineoplastic agent. It has been given orphan drug status for use in the treatment of primary brain tumors.	7.04	1	0	pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent
edetic acid Edetic Acid: A chelating agent that sequesters a variety of polyvalent cations such as CALCIUM. It is used in pharmaceutical manufacturing and as a food additive.	2.97	4	0	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
adenosine monophosphate Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.	2.43	2	0	adenosine 5'-phosphate; purine ribonucleoside 5'-monophosphate	adenosine A1 receptor agonist; cofactor; EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.11 (fructose-bisphosphatase) 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.	2.11	1	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
aniline [no description available]	3.51	2	0	anilines; primary arylamine
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.	2.49	2	0
phenylalanine Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.	2.78	3	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
1-naphthaldehyde 1-naphthaldehyde: structure. naphthaldehyde : An aldehyde in which the organyl group is a naphthyl group.. 1-naphthaldehyde : A naphthaldehyde with a formyl group at position 1.	2.05	1	0	naphthaldehyde	mouse metabolite
2-naphthaldehyde 2-naphthaldehyde: structure. 2-naphthaldehyde : A naphthaldehyde that is naphthalene substituted by a formyl group at position 2.	1.94	1	0	naphthaldehyde	mouse metabolite
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.	2.05	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.	3.49	2	0	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
sodium citrate, anhydrous Sodium Citrate: Sodium salts of citric acid that are used as buffers and food preservatives. They are used medically as anticoagulants in stored blood, and for urine alkalization in the prevention of KIDNEY STONES.. sodium citrate : The trisodium salt of citric acid.	2.1	1	0	organic sodium salt	anticoagulant; flavouring agent
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.	3.53	2	0	formamides; volatile organic compound	geroprotector; hepatotoxic agent; polar aprotic solvent
mannitol [no description available]	7.49	2	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
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.	3.07	1	0	pentanol; short-chain primary fatty alcohol	human metabolite; plant metabolite
1,1,1-trichloroethane Trichloroethanes: Chlorinated ethanes which are used extensively as industrial solvents. They have been utilized in numerous home-use products including spot remover preparations and inhalant decongestant sprays. These compounds cause central nervous system and cardiovascular depression and are hepatotoxic. Include 1,1,1- and 1,1,2-isomers.. 1,1,1-trichloroethane : A member of the class of chloroethanes carrying three chloro substituents at position 1.	3.5	2	0	chloroethanes	polar solvent
dichlorodiphenyldichloroethane Dichlorodiphenyldichloroethane: An organochlorine insecticide that is slightly irritating to the skin. (From Merck Index, 11th ed, p482)	2.03	1	0	chlorophenylethane; monochlorobenzenes; organochlorine insecticide	xenobiotic 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.	2.05	1	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.	2	1	0	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
methyl bromide methyl bromide: used in ionization chambers, degreasing wool, extracting oils; insect fumigant; high concentrations can produce pulmonary edema,narcosis; chronic exposure can cause CNS depression,kidney injury; RN given refers to parent cpd; structure. bromomethane : A one-carbon compound in which the carbon is attached by single bonds to three hydrogen atoms and one bromine atom. It is produced naturally by marine algae.	3.07	1	0	bromohydrocarbon; bromomethanes; methyl halides	algal metabolite; fumigant insecticide; marine metabolite
ethylene Plastipore: high density polyethylene sponge biocompatible material; used as posts in dental bridges	2.77	3	0	alkene; gas molecular entity	plant hormone; refrigerant
acetylene [no description available]	2.72	3	0	alkyne; gas molecular entity; terminal acetylenic compound
ethyl chloride Ethyl Chloride: A gas that condenses under slight pressure. Because of its low boiling point ethyl chloride sprayed on skin produces an intense cold by evaporation. Cold blocks nerve conduction. Ethyl chloride has been used in surgery but is primarily used to relieve local pain in sports medicine.. chloroethane : The simplest and least toxic member of the class of chloroethanes, that is ethane in which a single hydrogen is substituted by a chlorine. A colourless gas at room temperature and pressure (boiling point 12degreeC), it is used as a mild topical anaesthetic to numb the skin prior to ear piercing, skin biopsies, etc., and is also used in the treatment of sports injuries. It was formerly used in the production of tetraethyllead.	3.5	2	0	chloroethanes	antipruritic drug; inhalation anaesthetic; local anaesthetic
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.	4.01	4	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.	4.03	4	0	chloromethanes; volatile organic compound	carcinogenic agent; polar aprotic solvent; refrigerant
1,1-dichloroethane [no description available]	3.07	1	0	organochlorine compound
nitromethane nitromethane: structure. nitromethane : A primary nitroalkane that is methane in which one of the hydrogens is replace by a nitro group. A polar solvent (b.p. 101 degreeC), it is an important starting material in organic synthesis. It is also used as a fuel for rockets and radio-controlled models.	3.07	1	0	primary nitroalkane; volatile organic compound	EC 4.3.1.3 (histidine ammonia-lyase) inhibitor; explosive; NMR chemical shift reference compound; polar aprotic solvent
tert-butyl alcohol tert-Butyl Alcohol: An isomer of butanol that contains a tertiary butyl group that consists of three methyl groups, each separately attached to a central (tertiary) carbon.. tert-butanol : A tertiary alcohol alcohol that is isobutane substituted by a hydroxy group at position 2.	3.07	1	0	tertiary alcohol	human xenobiotic metabolite
trichlorofluoromethane trichlorofluoromethane: refrigerant, aerosol propellant; RN given refers to parent cpd; structure. trichlorofluoromethane : A one-carbon compound that is methane in which the hydrogens have been replaced by three chlorine and one fluorine atom.	2.04	1	0	chlorofluorocarbon; halomethane	environmental contaminant; NMR chemical shift reference compound; NMR solvent; refrigerant
tert-amyl alcohol 2-methylbutan-2-ol : A tertiary alcohol that is propan-1-ol in which both of the hydrogens at position 1 have been replaced by methyl groups.	3.07	1	0	aliphatic alcohol; tertiary alcohol	protic solvent
pentachloroethane [no description available]	2.04	1	0	chloroethanes	non-polar solvent
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.	2.15	1	0	monocarboxylic acid; organochlorine compound	carcinogenic agent; metabolite; mouse metabolite
phencyclidine Phencyclidine: A hallucinogen formerly used as a veterinary anesthetic, and briefly as a general anesthetic for humans. Phencyclidine is similar to KETAMINE in structure and in many of its effects. Like ketamine, it can produce a dissociative state. It exerts its pharmacological action through inhibition of NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE). As a drug of abuse, it is known as PCP and Angel Dust.. phencyclidine : A member of the class of piperidines that is piperidine in which the nitrogen is substituted with a 1-phenylcyclohexyl group. Formerly used as an anaesthetic agent, it exhibits both hallucinogenic and neurotoxic effects.	2.77	3	0	benzenes; piperidines	anaesthetic; neurotoxin; NMDA receptor antagonist; psychotropic drug
isopentane [no description available]	2.04	1	0	alkane	refrigerant
isoprene isoprene: used in manufacture of ''synthetic'' rubber, butyl rubber; copolymer in production of elastomers; structure. isoprene : A hemiterpene with the formula CH2=C(CH3)CH=CH2; the monomer of natural rubber and a common structure motif to the isoprenoids, a large class of other naturally occurring compounds.	2.06	1	0	alkadiene; hemiterpene; volatile organic compound	plant metabolite
isobutyl alcohol isobutyl alcohol: RN given refers to parent cpd	3.07	1	0	alkyl alcohol; primary alcohol	Saccharomyces cerevisiae metabolite
propylene dichloride propylene dichloride: Russian drug; structure. 1,2-dichloropropane : A chloroalkane that is propane in which a hydrogen from each of two adjacent carbons has been replaced by chlorines.	3.07	1	0	chloroalkane; volatile organic compound
2-butanol 2-butanol: RN given is for parent cpd without isomeric designation. butan-2-ol : A secondary alcohol that is butane substituted by a hydroxy group at position 2.	3.07	1	0	secondary alcohol
methylethyl ketone methylethyl ketone: solvent; colorless synthetic resins, smokeless powders; may be irritating to eyes, mucous membranes; may be toxic in high concentrations; structure. butanone : Any ketone that is butane substituted by an oxo group at unspecified position.. butan-2-one : A dialkyl ketone that is a four-carbon ketone carrying a single keto- group at position C-2.	3.07	1	0	butanone; dialkyl ketone; methyl ketone; volatile organic compound	bacterial metabolite; polar aprotic solvent
1,1,2-trichloroethane 1,1,2-trichloroethane: RN given refers to cpd with locants as specified. 1,1,2-trichloroethane : A member of the class of chloroethanes that is ethane substituted by chloro groups at positions 1, 1 and 2.	3.07	1	0	chloroethanes
trichloroethylene Trichloroethylene: A highly volatile inhalation anesthetic used mainly in short surgical procedures where light anesthesia with good analgesia is required. It is also used as an industrial solvent. Prolonged exposure to high concentrations of the vapor can lead to cardiotoxicity and neurological impairment.. triol : A chemical compound containing three hydroxy groups.	4.06	4	0	chloroethenes	inhalation anaesthetic; mouse metabolite
1,1,2,2-tetrachloroethane 1,1,2,2-tetrachloroethane: see also record for tetrachloroethane. 1,1,2,2-tetrachloroethane : A member of the class of chloroethanes that is ethane substituted by chloro groups at positions 1, 1, 2 and 2.	3.5	2	0	chloroethanes
pantothenic acid Pantothenic Acid: A butyryl-beta-alanine that can also be viewed as pantoic acid complexed with BETA ALANINE. It is incorporated into COENZYME A and protects cells against peroxidative damage by increasing the level of GLUTATHIONE.. pantothenic acid : A member of the class of pantothenic acids that is an amide formed from pantoic acid and beta-alanine.. vitamin B5 : Any member of a group of vitamers that belong to the chemical structural class called pantothenic acids that exhibit biological activity against vitamin B5 deficiency. Deficiency of vitamin B5 is rare due to its widespread distribution in whole grain cereals, legumes and meat. Symptoms associated with vitamin B5 deficiency are difficult to asses since they are subtle and resemble those of other B vitamin deficiencies. The vitamers include (R)-pantothenic acid and its ionized and salt forms.. (R)-pantothenate : A pantothenate that is the conjugate base of (R)-pantothenic acid, obtained by deprotonation of the carboxy group.. (R)-pantothenic acid : A pantothenic acid having R-configuration.	2.04	1	0	pantothenic acid; vitamin B5	antidote to curare poisoning; geroprotector; human blood serum metabolite
bisphenol a 4,4'-isopropylidene diphenol: stimulates proliferative responses and cytokine productions of murine spleen cells and thymus cells in vitro. bisphenol : By usage, the methylenediphenols, HOC6H4CH2C6H4OH, commonly p,p-methylenediphenol, and their substitution products (generally derived from condensation of two equivalent amounts of a phenol with an aldehyde or ketone). The term also includes analogues in the the methylene (or substituted methylene) group has been replaced by a heteroatom.. bisphenol A : A bisphenol that is 4,4'-methanediyldiphenol in which the methylene hydrogens are replaced by two methyl groups.	3.6	8	0	bisphenol	endocrine disruptor; environmental contaminant; xenobiotic; xenoestrogen
acenaphthenequinone acenaphthoquinone : An orthoquinone that is the 1,2-dioxo derivative of acenaphthene.	2.08	1	0	orthoquinones	chain carrier; epitope
acenaphthene [no description available]	9.23	17	0	acenaphthenes
7,8-dimethyl-10-[(2R,3R,4S)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione [no description available]	2.04	1	0	flavin
9,10-phenanthrenequinone 9,10-phenanthrenequinone: structure	3.76	10	0	phenanthrenes
phanquinone phanquinone: structure. phanquone : An orthoquinone that is the 5,6-diketo derivative of 4,7-phenanthroline.	1.93	1	0	orthoquinones
9,10-anthraquinone 9,10-anthraquinone : An anthraquinone that is anthracene in which positions 9 and 10 have been oxidised to carbonyls.	2.49	2	0	anthraquinone
benzo(f)quinoline [no description available]	2.37	2	0
1-hydroxy-2-naphthoic acid 1-hydroxy-2-naphthoic acid: RN given refers to parent cpd. 1-hydroxy-2-naphthoic acid : A naphthoic acid with the carboxy group at position 2 and carrying a hydroxy substituent at the 1-position. It is a xenobiotic metabolite produced by the biodegradation of phenanthrene by microorganisms.	4.06	14	0	hydroxy monocarboxylic acid; naphthoic acid; naphthols	bacterial xenobiotic metabolite; fungal xenobiotic metabolite
1-naphthoic acid naphthoic acid : An aromatic carboxylic acid that consists of a naphthalene skeleton substituted by one or more carboxy groups.	7.05	1	0	naphthoic acid	bacterial xenobiotic metabolite; fungal xenobiotic metabolite
fluorene [no description available]	5.75	80	0	ortho-fused polycyclic arene; ortho-fused tricyclic hydrocarbon
carbazole carbazole: structure in first source	7.49	2	0	carbazole
1,2,3-trichlorobenzene trichlorobenzene: commercial grade of trichlorobenzene containing 70% 1,2,4-trichlorobenzene & 30% 1,2,3-trichlorobenzene; see also record for 1,2,4-trichlorobenzene. trichlorobenzene : Any member of the class of chlorobenzenes carrying three chloro substituents at unspecified positions.. 1,2,3-trichlorobenzene : A trichlorobenzene carrying chloro substituents at positions 1, 2 and 3.	3.8	3	0	trichlorobenzene
hexamethylbenzene hexamethylbenzene : A methylbenzene that is benzene in which all six hydrogens have been replaced by methyl groups.	2.04	1	0	methylbenzene
2,4,6-trichlorophenol [no description available]	2.15	1	0	trichlorophenol	carcinogenic agent
2-nitrotoluene nitrotoluene : Any member of the class of toluenes bearing one or more nitro substituents on the benzene ring.	3.49	2	0	mononitrotoluene	carcinogenic agent; environmental contaminant
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.	3.51	2	0	monoterpenoid; phenols	volatile oil component
1-methylnaphthalene 1-methylnaphthalene : A methylnaphthalene carrying a methyl substituent at position 1.	2.96	4	0	methylnaphthalene	carcinogenic agent; plant metabolite
1-chloronaphthalene 1-chloronaphthalene: word preservative; in xylamon the active ingredient is 60% 1-chloronaphthalene; structure in Merck Index, 9th ed, #2126	2.94	4	0
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.	3.73	10	0	naphthol	genotoxin; human xenobiotic metabolite
2-phenylphenol 2-phenylphenol: RN given refers to parent cpd; structure. biphenyl-2-ol : A member of the class of hydroxybiphenyls that is biphenyl substituted by a hydroxy group at position 2. It is generally used as a post-harvest fungicide for citrus fruits.	2.46	2	0	hydroxybiphenyls	antifungal agrochemical; environmental food contaminant
anthrone anthrone: used in colorimetric determination of sugar & animal starch in body fluids; structure. anthrone : A member of the class of anthracenes that is 9,10-dihydroanthracene carrying an oxo group at C-9.	2.21	1	0	anthracenone	radical scavenger
quinoline [no description available]	4.02	4	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinolines
2-methylnaphthalene 2-methylnaphthalene: RN given refers to parent cpd. 2-methylnaphthalene : A methylnaphthalene carrying a methyl substituent at position 2.	2.9	4	0	methylnaphthalene
2-chloronaphthalene 2-chloronaphthalene: structure in first source	2.94	4	0
2-methylquinoline 2-methylquinoline: RN given refers to parent cpd. methylquinoline : Any member of the class of quinolines carrying at least one methyl substituent.. quinaldine : A quinoline compound in which the quinoline skeleton is substituted at C-2 with a methyl group.	2.44	2	0	quinolines
naphthacene tetracene : An acene that consists of four ortho-fused benzene rings in a rectilinear arrangement.	2.45	2	0	acene; tetracenes
diphenyl diphenyl: RN given refers to unlabeled cpd; structure	4.26	18	0	aromatic fungicide; benzenes; biphenyls	antifungal agrochemical; antimicrobial food preservative
3-hydroxy-2-naphthoic acid 3-hydroxy-2-naphthoic acid: RN given refers to parent cpd	1.94	1	0	naphthoic acid
xanthenes Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.	2	1	0	xanthene
2-methoxynaphthalene [no description available]	2.44	2	0	naphthalenes
methyleugenol methyleugenol: structure	2	1	0	phenylpropanoid
propylparaben Parabens: Methyl, propyl, butyl, and ethyl esters of p-hydroxybenzoic acid. They have been approved by the FDA as antimicrobial agents for foods and pharmaceuticals. (From Hawley's Condensed Chemical Dictionary, 11th ed, p872)	2.01	1	0	benzoate ester; paraben; phenols	antifungal agent; antimicrobial agent
2-xylene 2-xylene: RN given refers to parent cpd. o-xylene : A xylene substituted by methyl groups at positions 1 and 2.	3.82	3	0	xylene
2-chlorotoluene 2-chlorotoluene: RN given refers to parent cpd	2.04	1	0
2-dichlorobenzene 2-dichlorobenzene: structure. 1,2-dichlorobenzene : A dichlorobenzene carrying chloro substituents at positions 1 and 2.	3.8	3	0	dichlorobenzene	hepatotoxic agent; metabolite
pseudocumene 1,2,4-trimethylbenzene : A trimethylbenzene carrying methyl groups at positions 1, 2 and 4.	2.04	1	0	trimethylbenzene	neurotoxin
durene durene: structure. durene : A tetramethylbenzene carrying methyl groups at positions 1, 2, 4 and 5.	2.04	1	0	tetramethylbenzene
1,2,4,5-tetrachlorobenzene 1,2,4,5-tetrachlorobenzene : A tetrachlorobenzene carrying chloro groups at positions 1, 2, 4 and 5.	3.8	3	0	tetrachlorobenzene
diethyl ketone diethyl ketone: RN given refers to unlabeled parent cpd. pentan-3-one : A pentanone that is pentane carrying an oxo group at position 3. It has been isolated from Triatoma brasiliensis and Triatoma infestans.	3.07	1	0	pentanone	animal metabolite
cyclopentanol [no description available]	3.07	1	0	cyclopentanols
ethyl 2-methylpropanoate ethyl isobutyrate : A fatty acid ethyl ester obtained by the formal condensation of isobutyric acid with ethanol.	3.07	1	0	fatty acid ethyl ester	plant metabolite
ethyl lactate ethyl lactate: RN given refers to cpd with unspecified isomeric designation. ethyl 2-hydroxypropanoate : The ethyl ester obtained of 2-hydroxypropanoic acid.	2.13	1	0	ethyl ester; lactate ester; secondary alcohol	metabolite
ethylene dimethacrylate ethylene glycol dimethacrylate : The enoate ester that is the 1,2-bis(methacryloyl) derivative of ethylene glycol.	2.04	1	0	enoate ester	allergen; cross-linking reagent; polymerisation monomer
tert-butylbenzene [no description available]	2.04	1	0
butylphen butylphen: irritant; structure. 4-tert-butylphenol : A member of the class of phenols that is phenol substituted with a tert-butyl group at position 4.	3.07	1	0	phenols	allergen
cumene cumene : An alkylbenzene that is benzene carrying an isopropyl group.	2.04	1	0	alkylbenzene
acetophenone acetophenone : A methyl ketone that is acetone in which one of the methyl groups has been replaced by a phenyl group.	3.07	1	0	acetophenones	animal metabolite; photosensitizing agent; xenobiotic
nitrobenzene nitrobenzene : A nitroarene consisting of benzene carrying a single nitro substituent. An industrial chemical used widely in the production of aniline.	3.82	3	0	nitroarene; nitrobenzenes
3-nitrotoluene [no description available]	2.03	1	0	mononitrotoluene
trehalose alpha,alpha-trehalose : A trehalose in which both glucose residues have alpha-configuration at the anomeric carbon.	2.48	2	0	trehalose	Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
sym-trinitrobenzene Trinitrobenzenes: Benzene derivatives which are substituted with three nitro groups in any position.. 1,3,5-trinitrobenzene : A trinitrobenzene in which each of the nitro groups is meta- to the other two.	2.02	1	0	trinitrobenzene	explosive
3-dinitrobenzene dinitrobenzene : Any member of the class of nitrobenzenes that consists of a benzene ring substituted by two nitro groups. A closed class.. 1,3-dinitrobenzene : A dinitrobenzene that is benzene disubstituted at positions 1 and 3 with nitro groups.	2.15	1	0	dinitrobenzene	neurotoxin
4-cymene 4-cymene: structure. p-cymene : A monoterpene that is toluene substituted by an isopropyl group at position 4.	2.04	1	0	monoterpene; toluenes	human urinary metabolite; plant metabolite; volatile oil component
4-nitrotoluene 4-nitrotoluene: RN given refers to parent cpd; structure in Merck Index, 9th ed, #6470. mononitrotoluene : A nitrotoluene bearing a single nitro substituent at any position. A "closed class".. 4-nitrotoluene : A mononitrotoluene that consists of toluene bearing a nitro substituent at the 4-position.	2.13	1	0	mononitrotoluene
4-nitroanisole 4-nitroanisole: dye intermediate; organic synthesis; structure. 4-nitroanisole : A member of the class of 4-nitroanisoles that is anisole in which one the hydrogen meta to the methoxy group is replaced by a nitro group.	1.99	1	0	4-nitroanisoles
ethylbenzene [no description available]	2.04	1	0	alkylbenzene
anisole anisole : A monomethoxybenzene that is benzene substituted by a methoxy group.	3.07	1	0	monomethoxybenzene	plant metabolite
diphenylmethane diphenylmethane : A diarylmethane that is methane substituted by two phenyl groups.	2.17	1	0	diarylmethane
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.	2.1	1	0	aromatic ether	plant metabolite
1,2-dihydrostilbene 1,2-dihydrostilbene: intermdiate in biosynthesis of dihydrophenanthrenes from phenylalanine. 1,2-dihydrostilbene : A diphenylethane that is the 1,2-dihydro derivative of stilbene.	2.04	1	0	diphenylethane
n-propylbenzene n-propylbenzene: RN given refers to parent cpd. propylbenzene : An alkylbenzene that is benzene having one of its aromatic hydrogens substituted by a propyl group.	2.04	1	0	alkylbenzene
n-butylbenzene butylbenzene : An alkylbenzene that is benzene substituted by a butyl group at position 1.	2.04	1	0	alkylbenzene
4-methylbenzaldehyde p-tolualdehyde : A tolualdehyde compound with the methyl substituent at the 4-position.	2.02	1	0	tolualdehyde	plant metabolite
ethyl propionate ethyl propionate: cholesterol gallstone solvent. ethyl propionate : A propanoate ester of ethanol.	3.07	1	0	propanoate ester	metabolite
ethyl butyrate ethyl butyrate : A butyrate ester resulting from the formal condensation of the hydroxy group of ethanol with the carboxy group of butyric acid.	3.07	1	0	butyrate ester	plant metabolite
2,4-dimethylphenol 2,4-dimethylphenol: RN given refers to parent cpd. 2,4-xylenol : A member of the class of phenols that phenol substituted by methyl groups at positions 2 and 4.	3.07	1	0	aromatic fungicide; phenols	disinfectant; volatile oil component
1,4-dibromobenzene [no description available]	2.73	3	0	dibromobenzene
4-xylene p-xylene : A xylene with methyl groups at positions 1 and 4.	2.04	1	0	xylene
4-chlorotoluene 4-chlorotoluene: RN given refers to unlabeled cpd	2.04	1	0	monochlorobenzenes
4-phenylenediamine 4-phenylenediamine: agent hair dye responsible for contact dermatitis; RN given refers to parent cpd. 1,4-phenylenediamine : A phenylenediamine in which the amino functions are at positions 1 and 4 of the benzene nucleus.	2.6	1	0	phenylenediamine	allergen; dye; hapten; reagent
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.	2.04	1	0	enoate ester; epoxide
ethylene dibromide Ethylene Dibromide: An effective soil fumigant, insecticide, and nematocide. In humans, it causes severe burning of skin and irritation of the eyes and respiratory tract. Prolonged inhalation may cause liver necrosis. It is also used in gasoline. Members of this group have caused liver and lung cancers in rodents. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), 1,2-dibromoethane may reasonably be anticipated to be a carcinogen.. 1,2-dibromoethane : A bromoalkane that is ethane carrying bromo substituents at positions 1 and 2. It is produced by marine algae.	2.04	1	0	bromoalkane; bromohydrocarbon	algal metabolite; carcinogenic agent; fumigant; marine metabolite; mouse metabolite; mutagen
butane butane : A straight chain alkane composed of 4 carbon atoms.	2.04	1	0	alkane; gas molecular entity	food propellant; refrigerant
1-butene but-1-ene : A butene with unsaturation at position 1.	2.04	1	0	butene
1,3-butadiene buta-1,3-diene : A butadiene with unsaturation at positions 1 and 3.	7.03	1	0	butadiene	carcinogenic agent; mutagen
allyl chloride [no description available]	7.04	1	0	organochlorine compound
methyl formate methyl formate: RN given refers to parent cpd. methyl formate : A formate ester resulting from the formal condensation of formic acid with methanol. A low-boiling (31.5 degreeC) colourless, flammable liquid, it has been used as a fumigant and larvicide for tobacco and food crops.	3.07	1	0	formate ester; methyl ester; volatile organic compound	fumigant; insecticide; polar aprotic solvent; refrigerant
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	3.13	5	0	alkane
2-pentanone pentanone : Any ketone that is pentane substituted by an oxo group at unspecified position.	3.07	1	0	methyl ketone; pentanone	plant metabolite
vinyl acetate [no description available]	2.03	1	0	acetate ester
methyl isobutyl ketone [no description available]	3.07	1	0	ketone
3-xylene m-xylene : A xylene carrying methyl groups at positions 1 and 3.	3.5	2	0	xylene
3-phenylenediamine 1,3-phenylenediamine : A phenylenediamine taht is benzene substituted at positions 1 and 3 with amino functions.	2.6	1	0	phenylenediamine
mesitylene mesitylene: structure. 1,3,5-trimethylbenzene : A trimethylbenzene carrying methyl substituents at positions 1, 3 and 5.	2.04	1	0	trimethylbenzene
1,3,5-trichlorobenzene 1,3,5-trichlorobenzene: structure in first source. 1,3,5-trichlorobenzene : A trichlorobenzene carrying chloro substituents at positions 1, 3 and 5.	3.8	3	0	trichlorobenzene
bromobenzene [no description available]	2.04	1	0	bromoarene; bromobenzenes; volatile organic compound	hepatotoxic agent; mouse metabolite; non-polar solvent
chlorobenzene [no description available]	3.8	3	0	monochlorobenzenes	solvent
cyclohexanol Cyclohexanols: Monohydroxy derivatives of cyclohexanes that contain the general formula R-C6H11O. They have a camphorlike odor and are used in making soaps, insecticides, germicides, dry cleaning, and plasticizers.. cyclohexanols : An alcohol in which one or more hydroxy groups are attached to a cyclohexane skeleton.	3.07	1	0	cyclohexanols; secondary alcohol	solvent
cyclohexanone [no description available]	3.07	1	0	cyclohexanones	human xenobiotic metabolite
propyl acetate propyl acetate: affects aggression without affecting motor activity; RN given refers to parent cpd. propyl acetate : An acetate ester obtained by the formal condensation of acetic acid with propanol.	3.07	1	0	acetate ester	fragrance; plant metabolite
pentane Pentanes: Five-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives.. pentane : A straight chain alkane consisting of 5 carbon atoms.	3.5	2	0	alkane; volatile organic compound	non-polar solvent; refrigerant
1-pentene 1-pentene: structure in first source	3.5	2	0
butyl chloride butyl chloride: structure	3.5	2	0
ethyl formate ethyl formate : A formate ester resulting from the formal condensation of formic acid with ethanol.. ethoxycarbonyl group : An organyl group of formula -COOEt.	3.07	1	0	ethyl ester; formate ester	fumigant; plant metabolite
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.	2.04	1	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.	3.07	1	0	cyclic ether; oxolanes; saturated organic heteromonocyclic parent; volatile organic compound	polar aprotic solvent
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	3.28	6	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
isobutyl acetate isobutyl acetate : The acetate ester of isobutanol.	3.07	1	0	acetate ester	Saccharomyces cerevisiae metabolite
n-hexane hexane : An unbranched alkane containing six carbon atoms.	2.04	1	0	alkane; volatile organic compound	neurotoxin; non-polar 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.	2.44	2	0	cycloalkane; volatile organic compound	non-polar solvent
cyclohexene cyclohexene : A cycloalkene that is cylohexane with a single double bond.	2.46	2	0	cycloalkene
2-octanone 2-octanone : A methyl ketone that is octane substituted by an oxo group at position 2.	3.07	1	0	methyl ketone	metabolite
1-hexanol 1-hexanol: RN given refers to parent cpd. hexanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of six carbon atoms.. hexan-1-ol : A primary alcohol that is hexane substituted by a hydroxy group at position 1.	3.07	1	0	hexanol; primary alcohol	alarm pheromone; antibacterial agent; fragrance; plant metabolite
heptanol Heptanol: A colorless liquid with a fragrant odor. It is used as an intermediate, solvent and in cosmetics.. heptanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of seven carbon atoms.. heptan-1-ol : A primary alcohol that is heptane substituted by a hydroxy group at position 1. It has been isolated from Capillipedium parviflorum.	3.07	1	0	heptanol; primary alcohol	flavouring agent; fragrance; gap junctional intercellular communication inhibitor; plant metabolite
nonane iotrochotin: toxin from the Caribbean sponge Iotrochota birotulata, which selectively permeabilizes synaptosomes. nonane : A straight chain alkane composed of 9 carbon atoms.	2.04	1	0	alkane	plant metabolite; volatile oil component
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.	2.05	1	0	decanol; primary alcohol	metabolite; pheromone; protic solvent
n-dodecane dodecane : A straight-chain alkane with 12 carbon atoms. It has been isolated from the essential oils of various plants including Zingiber officinale (ginger).	2.47	2	0	alkane	plant metabolite
eicosane icosane : A straight chain alkane composed of 20 carbon atoms. It has been isolated from the leaves of Agave attenuata.	7.75	3	0	long-chain alkane	plant metabolite
dimethyl ether dimethyl ether : An ether in which the oxygen atom is connected to two methyl groups.	7.41	1	0	ether
diethylhexyl phthalate Diethylhexyl Phthalate: An ester of phthalic acid. It appears as a light-colored, odorless liquid and is used as a plasticizer for many resins and elastomers.. bis(2-ethylhexyl) phthalate : A phthalate ester that is the bis(2-ethylhexyl) ester of benzene-1,2-dicarboxylic acid.	2.42	2	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.	2.04	1	0	aromatic fungicide; chlorobenzenes	antifungal agrochemical; carcinogenic agent; persistent organic pollutant
tetralin tetralin: structure given in first source. tetralin : An ortho-fused bicyclic hydrocarbon that is 1,2,3,4-tetrahydro derivative of naphthalene.	2.06	1	0	ortho-fused bicyclic hydrocarbon; tetralins
isoquinoline [no description available]	2.46	2	0	azaarene; isoquinolines; mancude organic heterobicyclic parent; ortho-fused heteroarene
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.	9.51	128	0	acene; anthracenes; ortho-fused tricyclic hydrocarbon
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.	2.13	1	0	dichlorophenol
cyclopentanone [no description available]	3.07	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.	2.1	1	0	dinitrotoluene
1-naphthylamine 1-Naphthylamine: A suspected industrial carcinogen (and listed as such by OSHA). Its N-hydroxy metabolite is strongly carcinogenic and mutagenic.. naphthylamine : A primary arylamine that is naphthalene substituted by an amino group at unspecified position.. 1-naphthylamine : A naphthylamine that is naphthalene substituted by an amino group at position 1.	7.08	1	0	naphthylamine	human xenobiotic metabolite
benzil benzil: structure. benzil : An alpha-diketone that is ethane-1,2-dione substituted by phenyl groups at positions 1 and 2 respectively.	2.08	1	0	alpha-diketone; aromatic ketone
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.	11.02	35	0	naphthol	antinematodal drug; genotoxin; human urinary metabolite; human xenobiotic metabolite; mouse metabolite; radical scavenger
dodecyl sulfate dodecyl sulfate: RN given refers to parent cpd; see also SODIUM DODECYL SULFATE	2.1	1	0	alkyl sulfate
sterogenol hexadecylpyridinium bromide: structure in first source. cetylpyridinium bromide : A pyridinium salt that has N-hexadecylpyridinium as the cation and bromide as the anion.	2.07	1	0	bromide salt; pyridinium salt	antiseptic drug; EC 2.7.11.18 (myosin-light-chain kinase) inhibitor; surfactant
citronellol citronellol: alcohol form of citronellal; found in rose oil; RN given refers to parent cpd without isomeric designation; structure. citronellol : A monoterpenoid that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7.. insect repellent : An insecticide that acts as a repellent to insects.	2.03	1	0	monoterpenoid	plant metabolite
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	3.07	1	0	acetate ester; ethyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; metabolite; polar aprotic solvent; Saccharomyces cerevisiae metabolite
hexanoic acid hexanoic acid : A C6, straight-chain saturated fatty acid.	7.25	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	human metabolite; plant metabolite
n-heptane Heptanes: Seven-carbon alkanes with the formula C7H16.. heptane : A straight-chain alkane with seven carbon atoms. It has been found in Jeffrey pine (Pinus jeffreyi).	7.46	2	0	alkane; volatile organic compound	non-polar solvent; plant metabolite
dibutyl ether [no description available]	3.07	1	0
diphenhydramine hydrochloride Antitussive Agents: Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally.. diphenhydramine hydrochloride : The hydrochloride salt of diphenhydramine.	1.93	1	0	hydrochloride; organoammonium salt	anti-allergic agent; antiemetic; antiparkinson drug; antipruritic drug; H1-receptor antagonist; local anaesthetic; muscarinic antagonist; sedative
aziridine [no description available]	7.45	2	0	azacycloalkane; aziridines; saturated organic heteromonocyclic parent	alkylating agent
catechin Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.	2.41	1	0	catechin	antioxidant; plant metabolite
coronene coronene: structure. coronene : A ortho- and peri-fused polycyclic arene that consists of six peri-fused benzene rings.	7.98	4	0	ortho- and peri-fused polycyclic arene
1,12-benzoperylene 1,12-benzoperylene: structure; see also record for benzoperylene	2.94	4	0	ortho- and peri-fused polycyclic arene
anthanthrene [no description available]	2.07	1	0	ortho- and peri-fused polycyclic arene
benzo(e)pyrene benzo(e)pyrene: RN given refers to parent cpd. benzo[e]pyrene : An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings. It is listed as a Group 3 carcinogen by the IARC.	2.93	4	0	ortho- and peri-fused polycyclic arene	carcinogenic agent; mutagen
indeno(1,2,3-cd)pyrene indeno(1,2,3-cd)pyrene: structure in first source	2.5	2	0	pyrenes
benzo(c)phenanthrene benzo[c]phenanthrene : An ortho-fused polycyclic arene resulting from the symmetrical fusion of the C1-C2 bonds of two naphthalene units.	2.64	3	0	benzenoid aromatic compound; ortho-fused polycyclic arene
perylene Perylene: A 20-carbon dibenz(de,kl)anthracene that can be viewed as a naphthalene fused to a phenalene or as dinaphthalene. It is used as fluorescent lipid probe in the cytochemistry of membranes and is a polycyclic hydrocarbon pollutant in soil and water. Derivatives may be carcinogenic.. perylene : An ortho- and peri-fused polycyclic arene comprising of five benzene rings that is anthracene in which the d,e and k,l sides are fused to benzene rings.	8.54	8	0	ortho- and peri-fused polycyclic arene; perylenes
benzo(j)fluoranthene benzo(j)fluoranthene: dihydrodiol metabolites identified as mutagens; structure given in first source	2.42	2	0	naphthalenes
benzo(b)fluoranthene benzo[b]fluoranthene : An ortho- and peri-fused polycyclic arene that consists of a benzene ring fused with a acephenanthrylene ring.	5	11	0	ortho- and peri-fused polycyclic arene	mutagen
fluoranthene fluoranthene: structure. fluoranthene : An ortho- and peri-fused polycyclic arene consisting of a naphthalene and benzene unit connected by a five-membered ring.	7.13	127	0	ortho- and peri-fused polycyclic arene
benzo(k)fluoranthene [no description available]	8.14	5	0	naphthalenes
acenaphthylene acenaphthylene: RN given refers to parent cpd. acenaphthylene : A ortho- and peri-fused tricyclic hydrocarbon that occurs in coal tar.	4.54	7	0	acenaphthylenes; ortho- and peri-fused polycyclic arene; ortho- and peri-fused tricyclic hydrocarbon
benzotriphenylene [no description available]	1.98	1	0	carbopolycyclic compound
triphenylene triphenylene: structure. triphenylene : An ortho-fused polycyclic arene consisting of four fused benzene rings.	2.45	2	0	ortho-fused polycyclic arene
chrysene chrysene: structure in Merck Index, 9th ed, #2252. chrysene : An ortho-fused polycyclic arene found commonly in the coal tar.	5.77	33	0	ortho-fused polycyclic arene	plant metabolite
dibenzo(aj)anthracene dibenzo(aj)anthracene: structure in first source	2.04	1	0	phenanthrenes
benzo(a)fluorene benzo(a)fluorene: structure in first source	2.04	1	0	carbotetracyclic compound
benzo(b)fluorene benzo(b)fluorene: structure in first source	2.04	1	0	carbotetracyclic compound
cinnoline cinnoline: structure in first source. cinnoline : An azaarene that is the 1,2-diaza analogue of naphthalene. The parent of the class of cinnolines.	2.47	2	0	azaarene; cinnolines; mancude organic heterobicyclic parent; ortho-fused heteroarene
quinazolines Quinazolines: A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.. quinazoline : A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.. quinazolines : Any organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.	2.04	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
acridines Acridines: Compounds that include the structure of acridine.. acridine : A polycyclic heteroarene that is anthracene in which one of the central CH groups is replaced by a nitrogen atom.	2.66	3	0	acridines; mancude organic heterotricyclic parent; polycyclic heteroarene	genotoxin
dibenzo(1,4)dioxin dibenzo(1,4)dioxin: structure	2.01	1	0	dibenzodioxine; heteranthrene; mancude organic heterotricyclic parent; oxacycle; polycyclic heteroarene
phenoxathiin phenoxathiin: structure given in first source	2	1	0
indazoles Indazoles: A group of heterocyclic aromatic organic compounds consisting of the fusion of BENZENE and PYRAZOLES.	2.06	1	0	indazole
adamantane Adamantane: A tricyclo bridged hydrocarbon.	2.46	2	0	adamantanes; polycyclic alkane
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	2.48	2	0	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
thiazoles [no description available]	2.04	1	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
cyclooctane [no description available]	2.04	1	0
thiocyanate thiocyanate: RN given refers to parent cpd. thiocyanate : A pseudohalide anion obtained by deprotonation of the thiol group of thiocyanic acid.	1.97	1	0	pseudohalide anion; sulfur molecular entity	human metabolite
diethyl sulfide ethyl sulfide : An aliphatic sulfide in which the sulfur atom is bonded to at least one ethyl group.. diethyl sulfide : An ethyl sulfide compound having two ethyl groups attached to a sulfur atom.	2.04	1	0	ethyl sulfide
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.	2.04	1	0	monofluorobenzenes	NMR chemical shift reference compound
propadiene [no description available]	2.04	1	0	allenes
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.	2.49	2	0	calcium salt; carbonate salt; inorganic calcium salt; one-carbon compound	antacid; fertilizer; food colouring; food firming agent
isocorydine isocorydine: from root tubers of Stephania Kwangsiensis H.S. Lo; RN given refers to (+-)-isomer; structure in Merck Index, 9th ed, #5017	1.99	1	0	aporphine alkaloid
cholanthrene cholanthrene: structure given in first source	2.04	1	0
menadiol [no description available]	2.04	1	0	methylnaphthalenes; naphthalenediols; naphthohydroquinone
diphenic acid [no description available]	2.93	4	0	dicarboxylic acid
retene retene: structure in first source	3.1	5	0
9-phenanthrol 9-phenanthrol: an inhibitor of AMP-dependent protein kinase catalytic subunit; structure in first source. 9-phenanthrol : A phenanthrol that is phenanthrene in which a hydrogen attached to a carbon in the central ring has been replaced by a hydroxy group.	3.13	5	0	phenanthrol	TRPM4 channel inhibitor
9-fluorenone fluoren-9-one : The simplest member of the class fluoren-9-ones that is 9H-fluorene bearing an oxo substituent at position 9.	7.89	3	0	fluoren-9-ones	fungal xenobiotic metabolite
elemicin [no description available]	2	1	0	olefinic compound
indoline indoline: structure given in first source	2	1	0	indoles
alpha-aminopyridine alpha-aminopyridine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #485. aminopyridine : Compounds containing a pyridine skeleton substituted by one or more amine groups.	2.15	1	0
cyanogen bromide Cyanogen Bromide: Cyanogen bromide (CNBr). A compound used in molecular biology to digest some proteins and as a coupling reagent for phosphoroamidate or pyrophosphate internucleotide bonds in DNA duplexes.	1.99	1	0
1,2-naphthoquinone naphthalene-1,2-dione: structure given in first source. 1,2-naphthoquinone : The parent structure of the family of 1,2-naphthoquinones, in which the oxo groups of the quinone moiety are at positions 1 and 2 of the naphthalene ring. It is a metabolite of naphthalene and is found in diesel exhaust particles.	2.08	1	0	1,2-naphthoquinones	aryl hydrocarbon receptor agonist; carcinogenic agent
hemimellitene hemimellitene: structure. 1,2,3-trimethylbenzene : A trimethylbenzene carrying methyl groups at positions 1, 2 and 3. It has been found in Centaurium erythraea.	2.04	1	0	trimethylbenzene	neurotoxin; plant metabolite
2,3,4,5,6-pentachloroaniline [no description available]	2.07	1	0
tropolone Tropolone: A seven-membered aromatic ring compound. It is structurally related to a number of naturally occurring antifungal compounds (ANTIFUNGAL AGENTS).. tropolone : A cyclic ketone that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2. It is a toxin produced by the agricultural pathogen Burkholderia plantarii.	6.93	1	0	alpha-hydroxy ketone; cyclic ketone; enol	bacterial metabolite; fungicide; toxin
phenylacetylene phenylacetylene: can polymerize into DENDRIMERS	2.43	2	0	benzenes
Ethyl pentanoate ethyl valerate: a green apple flavoring agent	3.07	1	0	fatty acid ester
1-chloropropane 1-chloropropane: structure in first source	2.04	1	0
2,2,4-trimethylpentane 2,2,4-trimethylpentane: nephrotoxic. isooctane : An alkane that consists of pentane bearing two methyl substituents at position 2 and a single methyl substituent at position 4.	2.04	1	0	alkane; volatile organic compound	fuel additive; nephrotoxin; non-polar solvent
1,3-dichlorobenzene 1,3-dichlorobenzene : A dichlorobenzene carrying chloro substituents at positions 1 and 3.	3.5	2	0	dichlorobenzene
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.	4.19	15	0	dialdehyde	biomarker
1-chlorohexane [no description available]	2.04	1	0
n-hexadecane n-hexadecane: structure. hexadecane : A straight-chain alkane with 16 carbon atoms. It is a component of essential oil isolated from long pepper.	3.99	13	0	long-chain alkane	non-polar solvent; plant metabolite; volatile oil component
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.	2.49	2	0	hydrochloride	acid-base indicator; dye; two-colour indicator
1,4-dimethylnaphthalene 1,4-dimethylnaphthalene : A dimethylnaphthalene carrying methyl groups at positions 1 and 4.	2.39	2	0	dimethylnaphthalene
1,2-dimethylnaphthalene 1,2-dimethylnaphthalene : A dimethylnaphthalene carrying methyl groups at positions 1 and 2.. dimethylnaphthalene : Any member of the class of naphthalenes carrying two methyl groups at unspecified positions.	2.44	2	0	dimethylnaphthalene
1,2-dihydroxynaphthalene 1,2-dihydroxynaphthalene: RN given refers to parent cpd	1.94	1	0	naphthalenediol	mouse metabolite
1,6-dimethylnaphthalene 1,6-dimethylnaphthalene: structure in first source	2.44	2	0	dimethylnaphthalene
2,6-dimethylnaphthalene 2,6-dimethylnaphthalene: RN given refers to parent cpd. 2,6-dimethylnaphthalene : A dimethylnaphthalene carrying methyl groups at positions 2 and 6.	3.84	4	0	dimethylnaphthalene	environmental contaminant
1,2-dibromobenzene dibromobenzene : Any member of the class of bromobenzenes that consists of a benzene or a substituted benzene ring carrying two bromo groups at unspecified positions.	2.04	1	0	dibromobenzene
iodobenzene iodobenzene: RN given refers to unlabeled parent cpd	2.04	1	0
1-hexene 1-hexene: structure in first source. 1-hexene : An alkene that is hexane carrying a double bond at position 1.	2.04	1	0	alkene
octadecane octadecane: RN given refers to parent cpd. octadecane : A straight-chain alkane carrying 18 carbon atoms.	3.32	6	0	long-chain alkane	bacterial metabolite; plant metabolite
pentafluorobenzoic acid [no description available]	2.02	1	0	perfluorinated compound
alpha-naphthoflavone alpha-naphthoflavone: inhibits P4501A1 and P4501A2; stimulates some activities of P4503A4. alpha-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the h side of flavone. A synthetic compound, it is an inhibitor of aromatase (EC 1.14.14.14).	2.02	1	0	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist; aryl hydrocarbon receptor antagonist; EC 1.14.14.14 (aromatase) inhibitor
2,6-dinitrotoluene 2,6-dinitrotoluene: RN given refers to cpd with specified locants for nitrogen moieties. 2,6-dinitrotoluene : A dinitrotoluene carrying nitro substituents at positions 2 and 6.	2.03	1	0	dinitrotoluene	genotoxin
pentachlorobenzene pentachlorobenzene: structure. pentachlorobenzene : A member of the class of pentachlorobenzenes that is benzene in which five of the hydrogens are replaced by chlorines. Now classed as a persistent organic pollutant under the Stockholm Convention.	3.8	3	0	pentachlorobenzenes	persistent organic pollutant
1-methylanthracene 1-methylanthracene: structure given in first source	2.01	1	0
3-methylquinoline [no description available]	2.44	2	0	methylquinoline	xenobiotic
2-methylanthracene 2-methylanthracene: structure given in first source	2.04	1	0
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	2.34	2	0	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
diazoacetic ester diazoacetic ester: structure	1.92	1	0
1,3-dicyanobenzene 1,3-dicyanobenzene: structure in first source	2.21	1	0	nitrile
3,5-dichloroaniline [no description available]	2.07	1	0	dichloroaniline
2-hexanol hexan-2-ol : A hexanol in which the hydroxy group is at position 2.	3.07	1	0	hexanol; secondary alcohol	human metabolite; plant metabolite; semiochemical
amyl acetate amyl acetate: sources do not specify n-isomer. pentyl acetate : An acetate ester of pentanol.	3.07	1	0	acetate ester	metabolite
n-tetradecane tetradecane : A straight chain alkane consisting of 14 carbon atoms.	2.78	3	0	long-chain alkane	plant metabolite; volatile oil component
1,2,3,4-tetrachlorobenzene 1,2,3,4-tetrachlorobenzene : A tetrachlorobenzene carrying chloro groups at positions 1, 2 , 3 and 4.. tetrachlorobenzene : Any member of the class of chlorobenzenes carrying four chloro groups at unspecified positions.	3.5	2	0	tetrachlorobenzene
1,2,3,5-tetrachlorobenzene 1,2,3,5-tetrachlorobenzene : A tetrachlorobenzene carrying chloro groups at positions 1, 2, 3 and 5.	3.5	2	0	tetrachlorobenzene
phytane [no description available]	2.07	1	0	diterpene
tetracosane tetracosane: a pure alkane compound. tetracosane : A straight-chain alkane containing 24 carbon atoms.	2.1	1	0	long-chain alkane	plant metabolite; volatile oil component
acetylenedicarboxylic acid dimethyl ester acetylenedicarboxylic acid dimethyl ester: inhibitor of oxidative phosphorylation	2.04	1	0
9-methylanthracene [no description available]	2.04	1	0
9,10-dimethylanthracene 9,10-dimethylanthracene: RN given refers to parent ion	2.04	1	0
4-nitrophenyl acetate [no description available]	2.88	1	0	C-nitro compound; phenyl acetates
1-methylphenanthrene 1-methylphenanthrene: structure in first source. 1-methylphenanthrene : A member of the class of phenanthrenes that is phenanthrene substituted by a methyl group at position 1.	7.94	4	0	phenanthrenes	mutagen
2,6-dimethylquinoline 2,6-dimethylquinoline: from roots of Peucedanum praeruptorum II	2.44	2	0
undecane undecane : A straight-chain alkane with 11 carbon atoms.	2.45	2	0	alkane
3-vinylpyridine 3-vinylpyridine: structure given in first source; formed from nicotine during smoking of tobacco products	2.05	1	0
calcium peroxide [no description available]	2.21	1	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).	1.96	1	0
sodium hydroxide Sodium Hydroxide: A highly caustic substance that is used to neutralize acids and make sodium salts. (From Merck Index, 11th ed)	2.76	3	0	alkali metal hydroxide
zinc oxide Zinc Oxide: A mild astringent and topical protectant with some antiseptic action. It is also used in bandages, pastes, ointments, dental cements, and as a sunblock.	2.84	3	0	zinc molecular entity
hydrofluoric acid Hydrofluoric Acid: Hydrofluoric acid. A solution of hydrogen fluoride in water. It is a colorless fuming liquid which can cause painful burns.. hydrogen fluoride : A diatomic molecule containing covalently bonded hydrogen and fluorine atoms.. organofluorine compound : An organofluorine compound is a compound containing at least one carbon-fluorine bond.	2.02	1	0	hydrogen halide; mononuclear parent hydride	NMR chemical shift reference compound
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.	2.51	2	0	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
6-methylchrysene 6-methylchrysene: RN given refers to parent cpd; structure given in first source	2.04	1	0	carbopolycyclic compound
1-methylisoquinoline 1-methylisoquinoline : An isoquinoline substituted by a methyl group at position 1.	2.44	2	0	isoquinolines
decane decane : A straight-chain alkane with 10 carbon atoms.	2.04	1	0	alkane
Propioveratrone [no description available]	2	1	0	aromatic ketone
tetrabutylammonium tetrabutylammonium: lipophilic probe; RN given refers to parent cpd	2.07	1	0	quaternary ammonium ion
3-chlorobiphenyl 3-chlorobiphenyl: RN given refers to cpd with specified locant for chlorine	2.02	1	0	monochlorobiphenyl
4-chlorobiphenyl 4-chlorobiphenyl : A monochlorobiphenyl carrying a chloro substituent at position 4.	2.73	3	0	monochlorobiphenyl
12-methylbenzanthracene [no description available]	2.04	1	0
2-methylphenanthrene [no description available]	2.37	2	0
7-methylbenzanthracene [no description available]	2.04	1	0
n-octadecyl mercaptan n-octadecyl mercaptan: structure given in first source	2.03	1	0
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.	1.96	1	0	1,4-dimercaptobutane-2,3-diol; butanediols; dithiol; glycol; thiol	chelator; human metabolite; reducing agent
5-methylchrysene 5-methylchrysene: methylchrysenes in tobacco smoke are suspected to contribute to tumorigenicity of this inhalant; RN given refers to unlabeled cpd; structure	2.04	1	0	carbopolycyclic compound
5,6-dimethylchrysene 5,6-dimethylchrysene: structure given in first source	2.04	1	0
7-ethylbenz(a)anthracene [no description available]	2.04	1	0
streptomycin [no description available]	2.02	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.	2.03	1	0	carbon oxoanion
2-acetamidophenanthrene [no description available]	1.93	1	0
1-hydroxypyrene 1-hydroxypyrene: pyrene metabolite; RN given refers to parent cpd	8.52	8	0	pyrenes
1-nitropyrene [no description available]	3.06	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.	2.15	1	0	chloropyridine; organic thiophosphate	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; environmental contaminant; insecticide; xenobiotic
manganese Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.	2.44	2	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.	2.99	4	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.	2.1	1	0	chromium group element atom	micronutrient
neon Neon: A noble gas with the atomic symbol Ne, atomic number 10, and atomic weight 20.18. It is found in the earth's crust and atmosphere as an inert, odorless gas and is used in vacuum tubes and incandescent lamps.	2.39	2	0	monoatomic neon; noble gas atom; p-block 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.	7.73	3	0	metal allergen; nickel group element atom; platinum group metal atom
ruthenium Ruthenium: A hard, brittle, grayish-white rare earth metal with an atomic symbol Ru, atomic number 44, and atomic weight 101.07. It is used as a catalyst and hardener for PLATINUM and PALLADIUM.	2.78	3	0	iron group element atom; platinum group metal atom
silver Silver: An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.	7.51	2	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.	2.04	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.	9.16	15	0	titanium group element atom
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.	2.39	2	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.	6.1	36	0	cadmium molecular entity; zinc group element atom
cerium Cerium: An element of the rare earth family of metals. It has the atomic symbol Ce, atomic number 58, and atomic weight 140.12. Cerium is a malleable metal used in industrial applications.	2.48	2	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.	3.53	8	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.	7.47	2	0	f-block element atom; lanthanoid atom
gold Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.	3.18	5	0	copper group element atom; elemental gold
vanadium Vanadium: A metallic element with the atomic symbol V, atomic number 23, and atomic weight 50.94. It is used in the manufacture of vanadium steel. Prolonged exposure can lead to chronic intoxication caused by absorption usually via the lungs.	2.06	1	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.	2	1	0	titanium group element atom
aluminum chloride Aluminum Chloride: A compound with the chemical formula AlCl3; the anhydrous salt is used as a catalyst in organic chemical synthesis, and hydrated salts are used topically as antiperspirants, and for the management of HYPERHYDROSIS.	2.03	1	0	aluminium coordination entity	Lewis acid
cupric chloride cupric chloride: RN given refers to unlabeled parent cpd. copper(II) chloride : An inorganic chloride of copper in which the metal is in the +2 oxidation state.	2.03	1	0	copper molecular entity; inorganic chloride	EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor
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.	2.11	1	0	magnesium salt; metal sulfate; organic magnesium salt	anaesthetic; analgesic; anti-arrhythmia drug; anticonvulsant; calcium channel blocker; cardiovascular drug; fertilizer; tocolytic agent
phosphoric acid, trisodium salt [no description available]	2.03	1	0	sodium phosphate
nickel chloride nickel chloride: RN given refers to cpd with MF of Ni-Cl2. nickel dichloride : A compound of nickel and chloride in which the ratio of nickel (in the +2 oxidation state) to chloride is 1:2.	2.01	1	0	nickel coordination entity	calcium channel blocker; hapten
sodium pyrophosphate sodium pyrophosphate: RN refers to diphosphoric acid, tetra-Na salt; structure. sodium diphosphate : An inorganic sodium salt comprised of a diphosphate(4-) anion and four sodium(1+) cations. More commonly known as tetrasodium pyrophosphate, it finds much use in the food industry as an emulsifier and in dental hygiene as a calcium-chelating salt.	2.07	1	0	inorganic sodium salt	chelator; food emulsifier; food thickening agent
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	1	0	inorganic nitrate salt; potassium salt	fertilizer
sodium sulfate [no description available]	2.04	1	0	inorganic sodium salt
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.	2.05	1	0	metal sulfate	emetic; fertilizer; sensitiser
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.	2.03	1	0	calcium salt; inorganic calcium salt
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.	4.78	9	0	diatomic fluorine; gas molecular entity	NMR chemical shift reference compound
poloxalene Poloxalene: A copolymer of polyethylene and polypropylene ether glycol. It is a non-ionic polyol surface-active agent used medically as a fecal softener and in cattle for prevention of bloat.. pluronic : A triblock copolymer composed of a central hydrophobic chain of poly(propylene oxide) flanked by two hydrophilic chains of poly(ethylene oxide).	2.71	3	0	epoxide
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.	3.61	9	0	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
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.	2.13	1	0	cadmium coordination entity
cadmium sulfate cadmium sulfate: RN given refers to cpd with MF of Cd-H2SO4	2.07	1	0	cadmium salt
n,n-dimethylphenylethylamine N,N-dimethylphenylethylamine: RN given refers to parent cpd	2.21	1	0	primary amine
rhamnose [no description available]	2	1	0	L-rhamnose
carbendazim carbendazim: carcinogen when combined with sodium nitrite; principle metabolite of thiophanate methyl & benomyl; structure. carbendazim : A member of the class of benzimidazoles that is 2-aminobenzimidazole in which the primary amino group is substituted by a methoxycarbonyl group. A fungicide, carbendazim controls Ascomycetes, Fungi Imperfecti, and Basidiomycetes on a wide variety of crops, including bananas, cereals, cotton, fruits, grapes, mushrooms, ornamentals, peanuts, sugarbeet, soybeans, tobacco, and vegetables.	2.07	1	0	benzimidazole fungicide; benzimidazoles; benzimidazolylcarbamate fungicide; carbamate ester	antifungal agrochemical; antinematodal drug; metabolite; microtubule-destabilising agent
chrysotile Asbestos, Serpentine: A type of asbestos that occurs in nature as the dihydrate of magnesium silicate. It exists in two forms: antigorite, a plated variety, and chrysotile, a fibrous variety. The latter makes up 95% of all asbestos products. (From Merck Index, 11th ed, p.893)	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.	9.16	15	0	titanium oxides	food colouring
dechlorane plus dechlorane plus: a flame retardant; structure in first source	7.21	1	0
myrmicacin myrmicacin: found in secretions of South American leaf-cutting ant; inhibitor for mitotic progression after metaphase. 3-hydroxydecanoic acid : A medium-chain fatty acid that is decanoic acid substituted at position 3 by a hydroxy group.	2.25	1	0	3-hydroxy fatty acid; medium-chain fatty acid	antimitotic; Escherichia coli metabolite
chromium chromium hexavalent ion: a human respiratory carcinogen	7.13	1	0	chromium cation; monoatomic hexacation
iodine [no description available]	2.68	3	0	halide anion; monoatomic iodine	human metabolite
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.	3.23	6	0	benzenes; phenyl acetates
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.	2.02	1	0	benzaldehydes	bacterial metabolite; human urinary metabolite; insect repellent; plant metabolite
butyl acetate butyl acetate: structure. butyl acetate : The acetate ester of butanol.	3.07	1	0	acetate ester	metabolite
tetrachloroethylene Tetrachloroethylene: A chlorinated hydrocarbon used as an industrial solvent and cooling liquid in electrical transformers. It is a potential carcinogen.	2.04	1	0	chlorocarbon; chloroethenes	nephrotoxic agent
ursodeoxycholic acid Ursodeoxycholic Acid: An epimer of chenodeoxycholic acid. It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic.. ursodeoxycholic acid : A bile acid found in the bile of bears (Ursidae) as a conjugate with taurine. Used therapeutically, it prevents the synthesis and absorption of cholesterol and can lead to the dissolution of gallstones.. ursodeoxycholate : A bile acid anion that is the conjugate base of ursodeoxycholic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	7.01	1	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
butylated hydroxytoluene 2,6-di-tert-butyl-4-methylphenol : A member of the class of phenols that is 4-methylphenol substituted by tert-butyl groups at positions 2 and 6.	2.08	1	0	phenols	antioxidant; ferroptosis inhibitor; food additive; geroprotector
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.	9.15	321	0	ortho- and peri-fused polycyclic arene	fluorescent probe; persistent organic pollutant
alkenes [no description available]	2.52	2	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).	2.46	2	0	inorganic sodium salt	antibacterial agent; explosive; mitochondrial respiratory-chain inhibitor; mutagen
octachlorostyrene [no description available]	6.96	1	0	organochlorine compound
2,3,4,5-tetrachlorobiphenyl tetrachlorobiphenyl : Any polychlorobiphenyl with molecular formula C12H6Cl4.	2.04	1	0	tetrachlorobenzene; tetrachlorobiphenyl
2,5-dichlorobiphenyl 2,5-dichlorobiphenyl : A dichlorobiphenyl that is p-dichlorobenzene in which one of the hydrogens has been replaced by a phenyl group.	7.44	2	0	dichlorobenzene; dichlorobiphenyl
2,4'-dichlorobiphenyl 2,4'-dichlorobiphenyl: RN given refers to unlabeled cpd. 2,4'-dichlorobiphenyl : A dichlorobiphenyl that is chlorobenzene in which the hydrogen at position 2 has been replaced by a 4-chlorophenyl group.	2.04	1	0	dichlorobiphenyl; monochlorobenzenes
2,4,5,2',4',5'-hexachlorobiphenyl [no description available]	2.47	2	0	hexachlorobiphenyl
2,4,6-trichlorobiphenyl 2,4,6-trichlorobiphenyl: structure given in first source	2.04	1	0
2,5,2',5'-tetrachlorobiphenyl 2,2',5,5'-tetrachlorobiphenyl : A tetrachlorobiphenyl that is biphenyl in which the hydrogens at the 2 and 5 position of each benzene ring are replaced by chlorines.	2.48	2	0	dichlorobenzene; tetrachlorobiphenyl
ribavirin Rebetron: Rebetron is tradename	2.5	2	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
tricyclazole tricyclazole: RN given refers to parent cpd. tricyclazole : A triazolobenzothiazole that is [1,2,4]triazolo[3,4-b][1,3]benzothiazole which is substituted at position 5 by a methyl group. A fungicide used for the control of rice blast, it is not approved for use within the European Union.	7.04	1	0	triazolobenzothiazole	antifungal agrochemical; melanin synthesis inhibitor
2,3,7,8-tetrachlorodibenzofuran 2,3,7,8-tetrachlorodibenzofuran: toxic product which was generated in Italy due to an explosion in a plant manufacturing 2,4,5-trichlorophenol	1.98	1	0	polychlorinated dibenzofuran
permethrin hemoglobin Atlanta-Coventry: Leu replaced by Pro at beta75 and Leu deleted at beta141	7.44	2	0	cyclopropanecarboxylate ester; cyclopropanes	agrochemical; ectoparasiticide; pyrethroid ester acaricide; pyrethroid ester insecticide; scabicide
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).	2.04	1	0
piperacillin Piperacillin: Semisynthetic, broad-spectrum, AMPICILLIN derived ureidopenicillin antibiotic proposed for PSEUDOMONAS infections. It is also used in combination with other antibiotics.. piperacillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-[(4-ethyl-2,3-dioxopiperazin-1-yl)carboxamido]-2-phenylacetamido group.	2.08	1	0	penicillin allergen; penicillin	antibacterial drug
colforsin Colforsin: Potent activator of the adenylate cyclase system and the biosynthesis of cyclic AMP. From the plant COLEUS FORSKOHLII. Has antihypertensive, positive inotropic, platelet aggregation inhibitory, and smooth muscle relaxant activities; also lowers intraocular pressure and promotes release of hormones from the pituitary gland.	2.01	1	0	acetate ester; cyclic ketone; labdane diterpenoid; organic heterotricyclic compound; tertiary alpha-hydroxy ketone; triol	adenylate cyclase agonist; anti-HIV agent; antihypertensive agent; plant metabolite; platelet aggregation inhibitor; protein kinase A agonist
sodium persulfate sodium persulfate: RN given refers to peroxydisulfuric acid, di-Na salt	2.1	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.	2.51	2	0	D-glucopyranose	epitope; mouse metabolite
5-methylcytosine 5-Methylcytosine: A methylated nucleotide base found in eukaryotic DNA. In ANIMALS, the DNA METHYLATION of CYTOSINE to form 5-methylcytosine is found primarily in the palindromic sequence CpG. In PLANTS, the methylated sequence is CpNpGp, where N can be any base.. 5-methylcytosine : A pyrimidine that is a derivative of cytosine, having a methyl group at the 5-position.	1.96	1	0	methylcytosine; pyrimidines	human metabolite
bathocuproine bathocuproine: reagent for copper; RN given refers to parent cpd	2.03	1	0
neocuproine neocuproine: Spectrophotometric determination of copper and ultramicro blood sugar determinations; structure; RN given refers to parent cpd. neocuproine : A member of the class of phenanthrolines that is 1,10-phenanthroline bearing two methyl substituents at positions 2 and 9.	2.03	1	0	phenanthrolines	chelator; copper chelator
laurosept Laurosept: RN given refers to bromide	2.76	3	0
4,7-phenanthroline [no description available]	1.93	1	0	phenanthroline
1,7-phenanthroline [no description available]	4.44	23	0	phenanthroline
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	3.07	5	0	1,2,3-triazole
dimidium dimidium: RN given refers to parent cpd	1.93	1	0
delphinidin Paraffin: A mixture of solid hydrocarbons obtained from petroleum. It has a wide range of uses including as a stiffening agent in ointments, as a lubricant, and as a topical anti-inflammatory. It is also commonly used as an embedding material in histology.. delphinidin chloride : An anthocyanidin chloride that has delphinidin as the cationic counterpart.	2.02	1	0	anthocyanidin chloride
beta-tetralone [no description available]	2.44	2	0
perfluorooctanesulfonamide perfluorooctanesulfonamide : A perfluorinated compound that is perfluorooctane in which one of the terminal fluorines has been replace by a sulfamoyl group.	2.11	1	0	perfluorinated compound; sulfonamide	persistent organic pollutant
allyltrimethylsilane allyltrimethylsilane: used to make allyl C-glycosylic compounds	2.21	1	0
enrofloxacin Enrofloxacin: A fluoroquinolone antibacterial and antimycoplasma agent that is used in veterinary practice.. enrofloxacin : A quinolinemonocarboxylic acid that is 1,4-dihydroquinoline-3-carboxylic acid substituted by an oxo group at position 4, a fluoro group at position 6, a cyclopropyl group at position 1 and a 4-ethylpiperazin-1-yl group at position 7. It is a veterinary antibacterial agent used for the treatment of pets.	2.6	1	0	cyclopropanes; N-alkylpiperazine; N-arylpiperazine; organofluorine compound; quinolinemonocarboxylic acid; quinolone	antibacterial agent; antimicrobial agent; antineoplastic agent
bufuralol bufuralol: RN given refers to cpd without isomeric designation; structure	2.4	2	0	benzofurans
1,10-phenanthroline-5,6-dione 1,10-phenanthroline-5,6-dione: has antineoplastic, intercalating, and trypanocidal activities; structure given in first source	2.08	1	0
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.	2.48	2	0	cerium molecular entity; metal oxide
perfluorooctane sulfonic acid perfluorooctane-1-sulfonic acid : A perfluoroalkanesulfonic acid that is octane-1-sulfonic acid in which all seventeen of the hydrogens that are attached to carbons hvae been replaced by fluorines.	2.11	1	0	perfluoroalkanesulfonic acid	antilipemic drug; persistent organic pollutant
1-hydroxybenzotriazole 1-hydroxybenzotriazole: RN given refers to parent cpd	7.41	2	0	benzotriazoles
4-hydroxyphenanthrene 4-hydroxyphenanthrene: a metabolite of polycyclic aromatic hydrocarbon	2.53	2	0	phenanthrol
coenzyme a [no description available]	2	1	0	adenosine 3',5'-bisphosphate	coenzyme; Escherichia coli metabolite; mouse metabolite
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.	9.35	6	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
fibrinogen Fibrinogen: Plasma glycoprotein clotted by thrombin, composed of a dimer of three non-identical pairs of polypeptide chains (alpha, beta, gamma) held together by disulfide bonds. Fibrinogen clotting is a sol-gel change involving complex molecular arrangements: whereas fibrinogen is cleaved by thrombin to form polypeptides A and B, the proteolytic action of other enzymes yields different fibrinogen degradation products.. D-iditol : The D-enantiomer of iditol.	2.07	1	0	iditol	fungal metabolite
goethite [no description available]	7.51	2	0
homocysteine Homocysteine: A thiol-containing amino acid formed by a demethylation of METHIONINE.. homocysteine : A sulfur-containing amino acid consisting of a glycine core with a 2-mercaptoethyl side-chain.. L-homocysteine : A homocysteine that has L configuration.	2.07	1	0	amino acid zwitterion; homocysteine; serine family amino acid	fundamental metabolite; mouse metabolite
tylophorine tylophorine: phenanthroindolizidine alkaloid	7.48	2	0	organic heteropentacyclic compound; organonitrogen heterocyclic compound
cryptopleurine cryptopleurine: plant bark alkaloid shown to inhibit protein synthesis; RN given refers to (R)-isomer; structure. cryptopleurine : An organic heteropentacyclic compound that is (14aR)-11,12,13,14,14a,15-hexahydro-9H-dibenzo[f,h]pyrido[1,2-b]isoquinoline substituted at positions 2, 3 and 6 by methoxy groups.	2.1	1	0	alkaloid antibiotic; alkaloid; aromatic ether; organic heteropentacyclic compound	antineoplastic agent; antiviral agent; protein synthesis inhibitor
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.	7.31	1	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.	2.71	3	0	D-glucuronic acid	algal metabolite
2,2',4,4'-tetrabromodiphenyl ether [no description available]	2.08	1	0	aromatic ether; organobromine compound
ro 2-7239 Ro 2-7239: structure	2.34	2	0
1-hydroxyphenanthrene 1-hydroxyphenanthrene: a metabolite of polycyclic aromatic hydrocarbon	2.48	2	0	phenanthrol	mouse metabolite
cobalt Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.	2.49	2	0	cobalt group element atom; metal allergen	micronutrient
9,10-epoxy-9,10-dihydrophenanthrene 9,10-epoxy-9,10-dihydrophenanthrene: RN given refers to cpd without isomeric designation	6.94	1	0	phenanthrene oxide
benz(j)aceanthrylene [no description available]	1.96	1	0	phenanthrenes
hydroxycotinine hydroxycotinine: metabolite of nicotine; RN given refers to (S)-isomer; structure. trans-3-hydroxycotinine : An N-alkylpyrrolidine that is cotinine substituted at position C-3 by a hydroxy group (the 3R,5S-diastereomer).	2.05	1	0	N-alkylpyrrolidine; pyridines; pyrrolidin-2-ones; pyrrolidine alkaloid
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.	2.01	1	0	2-acetyl-1-alkyl-sn-glycero-3-phosphocholine	antihypertensive agent; beta-adrenergic antagonist; bronchoconstrictor agent; hematologic agent; vasodilator agent
trans-1,2-dihydro-1,2-naphthalenediol trans-1,2-dihydro-1,2-naphthalenediol: structure in first source. (1S,2S)-1,2-dihydronaphthalene-1,2-diol : The (1S,2S)-isomer of trans-1,2-dihydronaphthalene-1,2-diol.	2.25	1	0	trans-1,2-dihydronaphthalene-1,2-diol
aporphine aporphine: RN given refers to parent cpd without isomeric designation. aporphine : An isoquinoline alkaloid that is the N-methyl derivative of 5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline.	7.45	2	0	aporphine alkaloid; isoquinoline alkaloid fundamental parent; tertiary amino compound
gastrodin gastrodin: the glucoside of 4-hydroxybenzyl alcohol (gastrodigenin); isolated from Gastrodia elata Blume;	2.13	1	0	glycoside
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	2.48	2	0	22-hydroxy steroid; 23-hydroxy steroid; 2alpha-hydroxy steroid; 3alpha-hydroxy steroid; brassinosteroid	plant growth stimulator; plant hormone
benzoperylene benzoperylene: see also record for 1,12-benzperylene	1.98	1	0
glyceraldehyde 3-phosphate dehydrogenase (304-313) glyceraldehyde 3-phosphate dehydrogenase (304-313): from Bacillus stearothermophilus	2.08	1	0
tenax tenax: porous polymer based on 2,6-diphenyl-p-phenylene oxide; used for trapping volatile organic compounds	7.97	4	0
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).	2.44	2	0	carbene; methanediyl
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.	3.55	8	0	fullerene	geroprotector
8,9-dihydro-8,9-dihydroxybenzanthracene 10,11-oxide 8,9-dihydro-8,9-dihydroxybenzanthracene 10,11-oxide: RN given refers to cpd without isomeric designation; structure given in first source	1.95	1	0
sauristolactam sauristolactam: lactam of 10-aminomethyl-3-hydroxy-4-methoxyphenanthrene-1-carboxylic acid isolated from Saururus cernuus; structure given in first source	1.99	1	0
xylose xylopyranose: structure in first source	2.17	1	0	D-xylose
ethynylpyridine ethynylpyridine: structure in first source	2.08	1	0
proline Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.	2.11	1	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
molybdenum chloride [no description available]	2.1	1	0
3,4-dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrobenz(a)anthracene 3,4-dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrobenz(a)anthracene: intermediate in carcinogenic & mutagenic process; RN given refers to cpd without isomeric designation; structure in first source	1.95	1	0
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	3.18	5	0	oxygen hydride; oxygen radical; reactive oxygen species
pseudonicotine pseudonicotine: structure. (R)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has R-configuration.	2.02	1	0	3-(1-methylpyrrolidin-2-yl)pyridine
dialuminum magnesium tetraoxide spinell: mineral that can be colored to match dentin	2.6	1	0
sodium percarbonate sodium percarbonate: RN given refers to unspecified Na salt	2.41	1	0
fenton's reagent Fenton's reagent: used for oxidizing sugars & alcohols	2.96	4	0
stephenanthrine stephenanthrine: from the root of Stephania tetranda S. Moore & Dennettia tripetala; structure in first source. stephanthrine : An organic heterotetracyclic compound that is 2-(2H-phenanthro[3,4-d][1,3]dioxole in which the hydrogen at position 5 has been replaced by a 2-(dimethylamino)ethyl group.	2.01	1	0	cyclic acetal; organic heterotetracyclic compound; tertiary amino compound
tetraphenylphosphonium tetraphenylphosphonium: RN given refers to parent cpd; structure. tetraphenylphosphonium : A polyatomic cation consisting of four phenyl groups attached to a central phosphonium.	2.02	1	0	heteroorganic entity; phosphorus molecular entity; polyatomic cation
desosamine desosamine: RN given for (D-xylo)-isomer; structure in first source	2.03	1	0	amino sugar
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.	2.73	3	0	biotins; vitamin B7	coenzyme; cofactor; Escherichia coli metabolite; fundamental metabolite; human metabolite; mouse metabolite; nutraceutical; prosthetic group; Saccharomyces cerevisiae metabolite
lignin Lignin: The most abundant natural aromatic organic polymer found in all vascular plants. Lignin together with cellulose and hemicellulose are the major cell wall components of the fibers of all wood and grass species. Lignin is composed of coniferyl, p-coumaryl, and sinapyl alcohols in varying ratios in different plant species. (From Merck Index, 11th ed). lignin : A polyphenylpropanoid derived from three monolignol monomers: trans-p-coumaryl alcohol, coniferol and trans-sinapyl alcohol. There is extensive cross-linking and no defined primary structure.	3.89	12	0
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	2	1	0	divalent inorganic anion; phosphite ion
aflatoxin b1 Aflatoxin B1: A potent hepatotoxic and hepatocarcinogenic mycotoxin produced by the Aspergillus flavus group of fungi. It is also mutagenic, teratogenic, and causes immunosuppression in animals. It is found as a contaminant in peanuts, cottonseed meal, corn, and other grains. The mycotoxin requires epoxidation to aflatoxin B1 2,3-oxide for activation. Microsomal monooxygenases biotransform the toxin to the less toxic metabolites aflatoxin M1 and Q1.. aflatoxin B1 : An aflatoxin having a tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4 and 11.	1.96	1	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
methyl-1alpha, 7alpha-dihydroxy-3-oxopregn-4-en-21-oate methyl-1alpha, 7alpha-dihydroxy-3-oxopregn-4-en-21-oate: structure; RN given refers to (1alpha,7alpha)-isomer	1.93	1	0
annetocin annetocin: an oxytocin-vasopressin related peptide from Eisenia foetida; potentiates spontaneous contractions of the gut , pulsatory contractions & bladder-shaking movement of the nephridia	2.07	1	0
cholic acid Cholic Acid: A major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion.. cholic acid : A bile acid that is 5beta-cholan-24-oic acid bearing three alpha-hydroxy substituents at position 3, 7 and 12.	2.1	1	0	12alpha-hydroxy steroid; 3alpha-hydroxy steroid; 7alpha-hydroxy steroid; bile acid; C24-steroid; trihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
delrin delrin: linear polyoxymethylene type acetal resin made by polymerization of formaldehyde; RN refers to multi-polymer	2.02	1	0
2-chlorobiphenyl 2-chlorobiphenyl: RN from Toxlit. 2-chlorobiphenyl : A monochlorobiphenyl carrying a single chloro substituent at position 2.. monochlorobiphenyl : A chlorobiphenyl carrying a single chloro substituent at unspecified position.. chlorobiphenyl : A chloroarene that consists of a biphenyl skeleton substituted by one or more chloro groups.	2.73	3	0	monochlorobiphenyl
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	2.93	4	0
potassium bromide potassium bromide : A metal bromide salt with a K(+) counterion.	2.05	1	0	potassium salt
metribolone Metribolone: A synthetic non-aromatizable androgen and anabolic steroid. It binds strongly to the androgen receptor and has therefore also been used as an affinity label for this receptor in the prostate and in prostatic tumors.. 17beta-hydroxy-17-methylestra-4,9,11-trien-3-one : A synthetic non-aromatisable androgen and anabolic steroid. It binds strongly to the androgen receptor and has therefore also been used as an affinity label for this receptor in the prostate and in prostatic tumors.	1.96	1	0	17beta-hydroxy steroid; 3-oxo steroid; anabolic androgenic steroid	androgen
permanganate [no description available]	2.17	1	0	manganese oxoacid
glycogen glycogen : A polydisperse, highly branched glucan composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage, joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some cumulative alpha(1->6) links also may occur. The branches in glycogen typically contain 8 to 12 glucose residues.	2.13	1	0
7-dehydrocholesterol [no description available]	2.04	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; cholestanoid; Delta(5),Delta(7)-sterol	human metabolite; mouse metabolite
tartaric acid tartaric acid: RN given refers to cpd with unspecified isomeric designation. D-tartaric acid : The D-enantiomer of tartaric acid.	2.08	1	0	tartaric acid	Escherichia coli metabolite
cortodoxone Cortodoxone: 17,21-Dihydroxypregn-4-ene-3,20-dione. A 17-hydroxycorticosteroid with glucocorticoid and anti-inflammatory activities.. 11-deoxycortisol : A deoxycortisol that is cortisol in which the hydroxy group at position 11 has been replaced by a hydrogen.	2.93	4	0	deoxycortisol; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	human metabolite; mouse metabolite
terconazole terconazole: structure & RN for (cis)-isomer from first source. terconazole : A racemate consisting of equimolar amounts of (2R,4S)- and (2S,4R)-terconazole. It has broad-spectrum antifungal activitiy and is used for the treatment of vaginal yeast infections (Candida).. (2R,4S)-terconazole : A 1-(4-{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-isopropylpiperazine in which positions 2 and 4 of the 1,3-dioxolane moiety have R and S configuration, respectively.	1.92	1	0	1-(4-{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-isopropylpiperazine
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.	2.01	1	0	tripeptide
sodium arsenite sodium arsenite : An inoganic sodium salt with formula with formula NaAsO2.	2.07	1	0	arsenic molecular entity; inorganic sodium salt	antibacterial agent; antifungal agent; antineoplastic agent; carcinogenic agent; herbicide; insecticide; rodenticide
7-deoxypancratistatin 7-deoxypancratistatin: a phytogenic antineoplastic agent; structure in first source	2.05	1	0	phenanthridines
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	4.36	19	0	cyclodextrin
arachidonic acid icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.	2.01	1	0	icosa-5,8,11,14-tetraenoic acid; long-chain fatty acid; omega-6 fatty acid	Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite; mouse metabolite
alpha-cyclodextrin alpha-cyclodextrin : A cycloamylose composed of six alpha-(1->4) linked D-glucopyranose units.	2.08	1	0	cyclodextrin
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).	2.04	1	0	retinol; vitamin A	human metabolite; mouse metabolite; plant metabolite
cyanoginosin lr cyanoginosin LR: cyclic heptapeptide from cyanobacterium Microcystis aeruginosa. microcystin-LR : A microcystin consisting of D-alanyl, L-leucyl, (3S)-3-methyl-D-beta-aspartyl,L-arginyl, 2S,3S,4E,6E,8S,9S)-3-amino-4,5,6,7-tetradehydro-9-methoxy-2,6,8-trimethyl-10-phenyldecanoyl, D-gamma-glutamyl, and 2,3-didehydro-N-methylalanyl residues joined into a 25-membered macrocycle. Produced by the cyanobacterium Microcystis aeruginosa, it is the most studied of the microcystins.	2.93	3	0	microcystin	bacterial metabolite; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; environmental contaminant; xenobiotic
oleic acid Oleic Acid: An unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed). oleic acid : An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.	2.15	1	0	octadec-9-enoic acid	antioxidant; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; mouse metabolite; plant metabolite; solvent
ferric hydroxide ferric hydroxide: additional RNs for iron hydroxide oxide: 11115-92-7, 20344-49-4; RN for unspecified iron hydroxide: 11113-66-9	7.48	2	0
cocaine Cocaine: An alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake.. cocaine : A tropane alkaloid obtained from leaves of the South American shrub Erythroxylon coca.	2.93	4	0	benzoate ester; methyl ester; tertiary amino compound; tropane alkaloid	adrenergic uptake inhibitor; central nervous system stimulant; dopamine uptake inhibitor; environmental contaminant; local anaesthetic; mouse metabolite; plant metabolite; serotonin uptake inhibitor; sodium channel blocker; sympathomimetic agent; vasoconstrictor agent; xenobiotic
eicosapentaenoic acid icosapentaenoic acid : Any straight-chain, C20 polyunsaturated fatty acid having five C=C double bonds.. all-cis-5,8,11,14,17-icosapentaenoic acid : An icosapentaenoic acid having five cis-double bonds at positions 5, 8, 11, 14 and 17.	2.15	1	0	icosapentaenoic acid; omega-3 fatty acid	anticholesteremic drug; antidepressant; antineoplastic agent; Daphnia galeata metabolite; fungal metabolite; micronutrient; mouse metabolite; nutraceutical
diethylstilbestrol Diethylstilbestrol: A synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen. (Merck, 11th ed). diethylstilbestrol : An olefinic compound that is trans-hex-3-ene in which the hydrogens at positions 3 and 4 have been replaced by p-hydroxyphenyl groups.	6.93	1	0	olefinic compound; polyphenol	antifungal agent; antineoplastic agent; autophagy inducer; calcium channel blocker; carcinogenic agent; EC 1.1.1.146 (11beta-hydroxysteroid dehydrogenase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; endocrine disruptor; xenoestrogen
riboflavin vitamin B2 : Any member of a group of vitamers that belong to the chemical structural class called flavins that exhibit biological activity against vitamin B2 deficiency. Symptoms associated with vitamin B2 deficiency include glossitis, seborrhea, angular stomaitis, cheilosis and photophobia. The vitamers include riboflavin and its phosphate derivatives (and includes their salt, ionised and hydrate forms).	2.61	2	0	flavin; vitamin B2	anti-inflammatory agent; antioxidant; cofactor; Escherichia coli metabolite; food colouring; fundamental metabolite; human urinary metabolite; mouse metabolite; photosensitizing agent; plant metabolite
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)	7.74	3	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.	2.03	1	0	acetate salt; ammonium salt	buffer; food acidity regulator
11-mercaptoundecanoic acid [no description available]	2.07	1	0
methyl triclosan methyl triclosan: structure in first source	2.08	1	0
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.	2.04	1	0	4-coumaric acid	food component; mouse metabolite; plant metabolite
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	8.48	8	0	stilbene
phenyl-n-tert-butylnitrone phenyl-N-tert-butylnitrone: a spin-trapping agent	2.03	1	0
antofine antofine: structure in first source. (-)-antofine : An organic heteropentacyclic compound that is (13aR)-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline substituted at positions 2, 3 and 6 by methoxy groups. It is an alkaloid produced by relatives of the milkweed family and exhibits antiviral, anti-inflammatory, antiadipogenic and antitumorigenic activities.	3.01	4	0	alkaloid antibiotic; alkaloid; aromatic ether; organic heteropentacyclic compound	angiogenesis inhibitor; anti-inflammatory agent; antimicrobial agent; antineoplastic agent; antiviral agent; phytotoxin; plant metabolite
pyrophosphate Diphosphates: Inorganic salts of phosphoric acid that contain two phosphate groups.	2.07	1	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.	3.75	10	0	hydroxypolyether	hepatotoxic agent; nonionic surfactant; sclerotherapy agent
cotinine Cotinine: The N-glucuronide conjugate of cotinine is a major urinary metabolite of NICOTINE. It thus serves as a biomarker of exposure to tobacco SMOKING. It has CNS stimulating properties.. (-)-cotinine : An N-alkylpyrrolidine that consists of N-methylpyrrolidinone bearing a pyridin-3-yl substituent at position C-5 (the 5S-enantiomer). It is an alkaloid commonly found in Nicotiana tabacum.	4.2	5	0	N-alkylpyrrolidine; pyridines; pyrrolidin-2-ones; pyrrolidine alkaloid	antidepressant; biomarker; human xenobiotic metabolite; plant metabolite
isoeugenol [no description available]	2	1	0	isoeugenol
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.	2.1	1	0	one-carbon compound; thioureas; ureas	antioxidant; chromophore
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.	2.72	3	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.	4.18	15	0
dipyrromethene dipyrromethene: structure in first source. dipyrrin : A dipyrrin that consists of pyrrole bearing a pyrrol-2-ylidenemethyl substituent at the 2-position.	8.54	2	0	dipyrrins
tert-butanesulfinamide tert-butanesulfinamide: structure in first source	2.1	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.	4.19	16	0	organic sodium salt	detergent; protein denaturant
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	2.04	1	0
bilirubin [no description available]	1.96	1	0	biladienes; dicarboxylic acid	antioxidant; human metabolite; mouse metabolite
linoleic acid Linoleic Acid: A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed). linoleic acid : An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.	2.41	2	0	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
maleylpyruvate [no description available]	2.11	1	0	4,6-dioxohept-2-enedioic acid; beta-diketone
rosin rosin: Resin from plant. Do not confuse with the specific compound: 3-phenyl-2-propenyl-(E)-beta-D-glucopyranoside, also know as rosin.	1.93	1	0
vitamin d 2 Ergocalciferols: Derivatives of ERGOSTEROL formed by ULTRAVIOLET RAYS breaking of the C9-C10 bond. They differ from CHOLECALCIFEROL in having a double bond between C22 and C23 and a methyl group at C24.. vitamin D2 : A vitamin D supplement and has been isolated from alfalfa.	2.04	1	0	hydroxy seco-steroid; seco-ergostane; vitamin D	bone density conservation agent; nutraceutical; plant metabolite; rodenticide
cholecalciferol Cholecalciferol: Derivative of 7-dehydroxycholesterol formed by ULTRAVIOLET RAYS breaking of the C9-C10 bond. It differs from ERGOCALCIFEROL in having a single bond between C22 and C23 and lacking a methyl group at C24.. calciol : A hydroxy seco-steroid that is (5Z,7E)-9,10-secocholesta-5,7,10(19)-triene in which the pro-S hydrogen at position 3 has been replaced by a hydroxy group. It is the inactive form of vitamin D3, being hydroxylated in the liver to calcidiol (25-hydroxyvitamin D3), which is then further hydroxylated in the kidney to give calcitriol (1,25-dihydroxyvitamin D3), the active hormone.	2.04	1	0	D3 vitamins; hydroxy seco-steroid; seco-cholestane; secondary alcohol; steroid hormone	geroprotector; human metabolite
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	2.04	1	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
amphotericin b Amphotericin B: Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela.. amphotericin B : A macrolide antibiotic used to treat potentially life-threatening fungal infections.	2	1	0	antibiotic antifungal drug; macrolide antibiotic; polyene antibiotic	antiamoebic agent; antiprotozoal drug; bacterial metabolite
vitamin k 1 Vitamin K 1: A family of phylloquinones that contains a ring of 2-methyl-1,4-naphthoquinone and an isoprenoid side chain. Members of this group of vitamin K 1 have only one double bond on the proximal isoprene unit. Rich sources of vitamin K 1 include green plants, algae, and photosynthetic bacteria. Vitamin K1 has antihemorrhagic and prothrombogenic activity.. phylloquinone : A member of the class of phylloquinones that consists of 1,4-naphthoquinone having methyl and phytyl groups at positions 2 and 3 respectively. The parent of the class of phylloquinones.	2.04	1	0	phylloquinones; vitamin K	cofactor; human metabolite; plant metabolite
sirolimus Sirolimus: A macrolide compound obtained from Streptomyces hygroscopicus that acts by selectively blocking the transcriptional activation of cytokines thereby inhibiting cytokine production. It is bioactive only when bound to IMMUNOPHILINS. Sirolimus is a potent immunosuppressant and possesses both antifungal and antineoplastic properties.. sirolimus : A macrolide lactam isolated from Streptomyces hygroscopicus consisting of a 29-membered ring containing 4 trans double bonds, three of which are conjugated. It is an antibiotic, immunosupressive and antineoplastic agent.	2.31	1	0	antibiotic antifungal drug; cyclic acetal; cyclic ketone; ether; macrolide lactam; organic heterotricyclic compound; secondary alcohol	antibacterial drug; anticoronaviral agent; antineoplastic agent; bacterial metabolite; geroprotector; immunosuppressive agent; mTOR inhibitor
gamma-cyclodextrin gamma-cyclodextrin : A cycloamylose composed of eight alpha-(1->4) linked D-glucopyranose units.	2.08	1	0	cyclodextrin
morphine Meconium: The thick green-to-black mucilaginous material found in the intestines of a full-term fetus. It consists of secretions of the INTESTINAL GLANDS; BILE PIGMENTS; FATTY ACIDS; AMNIOTIC FLUID; and intrauterine debris. It constitutes the first stools passed by a newborn.	2.62	3	0	morphinane alkaloid; organic heteropentacyclic compound; tertiary amino compound	anaesthetic; drug allergen; environmental contaminant; geroprotector; mu-opioid receptor agonist; opioid analgesic; plant metabolite; vasodilator agent; xenobiotic
cytochalasin b Cytochalasin B: A cytotoxic member of the CYTOCHALASINS.. cytochalasin B : An organic heterotricyclic compound, that is a mycotoxin which is cell permeable an an inhibitor of cytoplasmic division by blocking the formation of contractile microfilaments.	2.1	1	0	cytochalasin; lactam; lactone; organic heterotricyclic compound	actin polymerisation inhibitor; metabolite; mycotoxin; platelet aggregation inhibitor
1,2-oleoylphosphatidylcholine 1,2-oleoylphosphatidylcholine: RN given refers to (Z,Z)-isomer. dioleoyl phosphatidylcholine : A phosphatidylcholine in which the phosphatidyl acyl groups are both oleoyl.	2.1	1	0	phosphatidylcholine(1+)
biliverdine [no description available]	2.44	2	0
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	4.01	13	0	carbon group element atom; elemental lead; metal atom	neurotoxin
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	8.03	4	0	boron group element atom; elemental aluminium; metal atom
arsenic Arsenic: A shiny gray element with atomic symbol As, atomic number 33, and atomic weight 75. It occurs throughout the universe, mostly in the form of metallic arsenides. Most forms are toxic. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), arsenic and certain arsenic compounds have been listed as known carcinogens. (From Merck Index, 11th ed)	3.33	6	0	metalloid atom; pnictogen	micronutrient
dextromethorphan Dextromethorphan: Methyl analog of DEXTRORPHAN that shows high affinity binding to several regions of the brain, including the medullary cough center. This compound is an NMDA receptor antagonist (RECEPTORS, N-METHYL-D-ASPARTATE) and acts as a non-competitive channel blocker. It is one of the widely used ANTITUSSIVES, and is also used to study the involvement of glutamate receptors in neurotoxicity.. dextromethorphan : A 6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene in which the sterocenters at positions 4a, 10 and 10a have S-configuration. It is a prodrug of dextrorphan and used as an antitussive drug for suppressing cough.	1.99	1	0	6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene	antitussive; environmental contaminant; neurotoxin; NMDA receptor antagonist; oneirogen; prodrug; xenobiotic
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.	1.97	1	0	chalcogen; nonmetal atom	macronutrient
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.	2.1	1	0	alkatriene	fluorochrome
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	7.67	3	0	cysteinium	fundamental metabolite
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.	8.19	5	0	monoatomic phosphorus; nonmetal atom; pnictogen	macronutrient
boron Boron: A trace element with the atomic symbol B, atomic number 5, and atomic weight [10.806; 10.821]. Boron-10, an isotope of boron, is used as a neutron absorber in BORON NEUTRON CAPTURE THERAPY.	8.54	2	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	2.02	1	0
triolein Triolein: (Z)-9-Octadecenoic acid 1,2,3-propanetriyl ester.. triolein : A triglyceride formed by esterification of the three hydroxy groups of glycerol with oleic acid. Triolein is one of the two components of Lorenzo's oil.	2.11	1	0	triglyceride	Caenorhabditis elegans metabolite; plant metabolite
carbocyanines Carbocyanines: Compounds that contain three methine groups. They are frequently used as cationic dyes used for differential staining of biological materials.	2.21	1	0	cyanine dye; organic iodide salt	fluorochrome
pregnanediol [no description available]	1.94	1	0
1-palmitoyl-2-oleoylphosphatidylcholine 1-palmitoyl-2-oleoylphosphatidylcholine: RN given refers to (Z)-isomer	2.05	1	0
vitamin a2 vitamin A2: RN given refers to cpd without isomeric designation. all-trans-3,4-didehydroretinol : A retinoid derived from 3,4-desaturation of the beta-ionone ring of all-trans-retinol.	2.04	1	0	retinoid; vitamin A	human xenobiotic metabolite; marine xenobiotic metabolite; mouse metabolite
trk 820 TRK 820: structure in first source	2.07	1	0	phenanthrenes
chlorophyll chlorophyll a': RN refers to (SP-4-2-(3S-(3alpha(2E,7S,11S),4beta,21alpha)))-isomer	2.21	1	0
beta-escin [no description available]	2.95	4	0
morphinans Morphinans: Compounds based on a partially saturated iminoethanophenanthrene, which can be described as ethylimino-bridged benzo-decahydronaphthalenes. They include some of the OPIOIDS found in PAPAVER that are used as ANALGESICS.	2.07	1	0	isoquinoline alkaloid fundamental parent; morphinane alkaloid
mocetinostat mocetinostat: undergoing phase II clinical trials for treatment of cancer. mocetinostat : A benzamide obtained by formal condensation of the carboxy group of 4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid with one of the amino groups of benzene-1,2-diamine. It is an orally active and isotype-selective HDAC inhibitor which exhibits antitumour activity (IC50 = 0.15, 0.29, 1.66 and 0.59 muM for HDAC1, HDAC2, HDAC3 and HDAC11).	3.36	6	0	aminopyrimidine; benzamides; pyridines; secondary amino compound; secondary carboxamide; substituted aniline	antineoplastic agent; apoptosis inducer; autophagy inducer; cardioprotective agent; EC 3.5.1.98 (histone deacetylase) inhibitor; hepatotoxic agent
zeolites [no description available]	3.03	4	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.	7.95	4	0
phosphoramidite phosphoramidite: structure in first source. phosphoramidite : A compound with the general formula (RO)2PNR2. Phosphoramidites can be regarded as phosphites that have an NR2 instead of an OH group, or as amides of phosphorous acid.	2.02	1	0
3,7-dihydroxy-2,4-dimethoxyphenanthrene 3,7-dihydroxy-2,4-dimethoxyphenanthrene: from the orchid Scaphyglottis livida; structure in first source	2.08	1	0
chlorophyll b [no description available]	2.63	2	0	chlorophyll	cofactor
sepharose agarose : A linear polysaccharide made up from alternating D-galactose and 3,6-anhydro-alpha-L-galactopyranose residues joined by alpha-(1->3)- and beta-(1->4)-linkages.	2.52	2	0
ethidium homodimer-1 [no description available]	1.93	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.	2.07	1	0
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	2.4	2	0	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
gramicidin a Gramicidin: A group of peptide antibiotics from BACILLUS brevis. Gramicidin C or S is a cyclic, ten-amino acid polypeptide and gramicidins A, B, D are linear. Gramicidin is one of the two principal components of TYROTHRICIN.	2.33	2	0
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.	2.06	1	0
oligonucleotides [no description available]	2.76	3	0
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	3.3	6	0	glycoside
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	2.72	3	0	1,2-diacyl-sn-glycero-3-phosphocholine
chlorophyll a Chlorophyll: Porphyrin derivatives containing magnesium that act to convert light energy in photosynthetic organisms.. chlorophyll : A family of magnesium porphyrins, defined by the presence of a fifth ring beyond the four pyrrole-like rings. The rings can have various side chains which usually include a long phytol chain.	4.4	19	0	chlorophyll; methyl ester	cofactor
chitosan [no description available]	7.66	2	0
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [no description available]	8.58	2	0	BODIPY compound
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)	3.01	4	0
glycolipids [no description available]	4.6	24	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.	3.15	5	0	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
salicylates Salicylates: The salts or esters of salicylic acids, or salicylate esters of an organic acid. Some of these have analgesic, antipyretic, and anti-inflammatory activities by inhibiting prostaglandin synthesis.. hydroxybenzoate : Any benzoate derivative carrying a single carboxylate group and at least one hydroxy substituent.. salicylates : Any salt or ester arising from reaction of the carboxy group of salicylic acid, or any ester resulting from the condensation of the phenolic hydroxy group of salicylic acid with an organic acid.. salicylate : A monohydroxybenzoate that is the conjugate base of salicylic acid.	2.74	3	0	monohydroxybenzoate	plant metabolite
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	2.92	4	0	benzenes; hydroxycoumarin; methyl ketone
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.	4.01	13	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.	4.43	21	0
agar Agar: A complex sulfated polymer of galactose units, extracted from Gelidium cartilagineum, Gracilaria confervoides, and related red algae. It is used as a gel in the preparation of solid culture media for microorganisms, as a bulk laxative, in making emulsions, and as a supporting medium for immunodiffusion and immunoelectrophoresis.. agar : A complex mixture of polysaccharides extracted from species of red algae. Its two main components are agarose and agaropectin. Agarose is the component responsible for the high-strength gelling properties of agar, while agaropectin provides the viscous properties.	2.44	2	0
illite [no description available]	2.05	1	0
asbestos, crocidolite Asbestos, Crocidolite: A lavender, acid-resistant asbestos.	1.96	1	0
phthalocyanine phthalocyanine : A tetrapyrrole fundamental parent that consists of four isoindole-type units, with the connecting carbon atoms in the macrocycle replaced by nitrogen.	2.06	1	0	phthalocyanines; tetrapyrrole fundamental parent
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	2.88	1	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.	2.44	2	0
jarosite [no description available]	7.25	1	0
phenanthroindolizidine phenanthroindolizidine: structure in first source	7.13	1	0
orabase Orabase: used in therapy of oral mucosal ulcers	2.41	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
guanosine triphosphate Guanosine Triphosphate: Guanosine 5'-(tetrahydrogen triphosphate). A guanine nucleotide containing three phosphate groups esterified to the sugar moiety.	2.06	1	0	guanosine 5'-phosphate; purine ribonucleoside 5'-triphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor
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.	2.73	3	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	3.31	5	0
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.	2.21	1	0	guanosines	biomarker
2-naphthol orange 2-naphthol orange: structure; see also record for C.I. Solvent Orange 2	2.11	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.	2.1	1	0
cyanine dye 3 cyanine dye 3: structures of Cy3 derivatives given in first source	2.21	1	0
acetylcellulose acetylcellulose: coating compound. cellulose acetate : A glucan derivative obtained through the esterification of cellulose by acetic anhydride or acetic acid, resulting in the substitution of some of the hydroxy groups of cellulose by acetyl groups. It is used in a variety of applications including base material for photographic film, clothing, membrane filters, coatings, food packaging, and as a frame material for eyeglasses.	2.11	1	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.	2.05	1	0
dinitrobenzenes Dinitrobenzenes: Benzene derivatives which are substituted with two nitro groups in the ortho, meta or para positions.	2.77	3	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.	17.23	1,977	4

Condition	Relationship Strength	Studies	Trials
Innate Inflammatory Response [description not available]	2.05	1	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.	2.05	1	0
Benign Neoplasms [description not available]	4.76	12	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.	4.76	12	0
Infections, Staphylococcal [description not available]	2.31	1	0
Staphylococcal Infections Infections with bacteria of the genus STAPHYLOCOCCUS.	2.31	1	0
Delayed Effects, Prenatal Exposure [description not available]	2.6	1	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	2.88	3	0
Arrhythmia [description not available]	7.58	2	0
Arrhythmias, Cardiac Any disturbances of the normal rhythmic beating of the heart or MYOCARDIAL CONTRACTION. Cardiac arrhythmias can be classified by the abnormalities in HEART RATE, disorders of electrical impulse generation, or impulse conduction.	2.58	2	0
Cardiac Toxicity [description not available]	2.94	3	0
Auricular Fibrillation [description not available]	2.6	1	0
Atrial Fibrillation Abnormal cardiac rhythm that is characterized by rapid, uncoordinated firing of electrical impulses in the upper chambers of the heart (HEART ATRIA). In such case, blood cannot be effectively pumped into the lower chambers of the heart (HEART VENTRICLES). It is caused by abnormal impulse generation.	2.6	1	0
Cardiotoxicity Damage to the HEART or its function secondary to exposure to toxic substances such as drugs used in CHEMOTHERAPY; IMMUNOTHERAPY; or RADIATION.	2.94	3	0
Endometrioma An enlarged area of ENDOMETRIOSIS that resembles a tumor. It is usually found in the OVARY. When it is filled with old blood, it is known as a chocolate cyst.	2.6	1	0
Endometriosis A condition in which functional endometrial tissue is present outside the UTERUS. It is often confined to the PELVIS involving the OVARY, the ligaments, cul-de-sac, and the uterovesical peritoneum.	2.6	1	0
Diabetes Mellitus A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.	3.17	1	0
Cancer of Lung [description not available]	6.12	6	2
Lung Neoplasms Tumors or cancer of the LUNG.	6.12	6	2
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.	2.37	2	0
Cardiac Failure [description not available]	2.31	1	0
Heart Failure A heterogeneous condition in which the heart is unable to pump out sufficient blood to meet the metabolic need of the body. Heart failure can be caused by structural defects, functional abnormalities (VENTRICULAR DYSFUNCTION), or a sudden overload beyond its capacity. Chronic heart failure is more common than acute heart failure which results from sudden insult to cardiac function, such as MYOCARDIAL INFARCTION.	2.31	1	0
Autism [description not available]	7.31	1	0
Autistic Disorder A disorder beginning in childhood. It is marked by the presence of markedly abnormal or impaired development in social interaction and communication and a markedly restricted repertoire of activity and interest. Manifestations of the disorder vary greatly depending on the developmental level and chronological age of the individual. (DSM-V)	2.31	1	0
Anoxemia [description not available]	2.15	1	0
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	7.15	1	0
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	7.58	2	0
Fatty Liver, Nonalcoholic [description not available]	2.17	1	0
Non-alcoholic Fatty Liver Disease Fatty liver finding without excessive ALCOHOL CONSUMPTION.	2.17	1	0
Papilloma, Squamous Cell [description not available]	3.29	2	0
Papilloma A circumscribed benign epithelial tumor projecting from the surrounding surface; more precisely, a benign epithelial neoplasm consisting of villous or arborescent outgrowths of fibrovascular stroma covered by neoplastic cells. (Stedman, 25th ed)	3.29	2	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)	3.82	11	0
Chronic Hepatitis C [description not available]	2.21	1	0
Hepatitis, Viral, Non-A, Non-B, Parenterally-Transmitted [description not available]	2.21	1	0
Hepatitis C INFLAMMATION of the LIVER in humans caused by HEPATITIS C VIRUS, a single-stranded RNA virus. Its incubation period is 30-90 days. Hepatitis C is transmitted primarily by contaminated blood parenterally and is often associated with transfusion and intravenous drug abuse. However, in a significant number of cases, the source of hepatitis C infection is unknown.	2.21	1	0
Hepatitis C, Chronic INFLAMMATION of the LIVER in humans that is caused by HEPATITIS C VIRUS lasting six months or more. Chronic hepatitis C can lead to LIVER CIRRHOSIS.	2.21	1	0
Abnormalities, Autosome [description not available]	2.21	1	0
Acute Liver Injury, Drug-Induced [description not available]	2.41	2	0
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	2.41	2	0
Carcinoma, Epidermoid [description not available]	2.21	1	0
Hypopharyngeal Cancer [description not available]	2.21	1	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)	2.21	1	0
Hypopharyngeal Neoplasms Tumors or cancer of the HYPOPHARYNX.	2.21	1	0
Abnormalities, Cardiovascular [description not available]	2.08	1	0
Abnormalities, Drug-Induced Congenital abnormalities caused by medicinal substances or drugs of abuse given to or taken by the mother, or to which she is inadvertently exposed during the manufacture of such substances. The concept excludes abnormalities resulting from exposure to non-medicinal chemicals in the environment.	2.08	1	0
Cardiovascular Abnormalities Congenital, inherited, or acquired anomalies of the CARDIOVASCULAR SYSTEM, including the HEART and BLOOD VESSELS.	2.08	1	0
Idiopathic Parkinson Disease [description not available]	2.08	1	0
Dementia Praecox [description not available]	2.08	1	0
Parkinson Disease A progressive, degenerative neurologic disease characterized by a TREMOR that is maximal at rest, retropulsion (i.e. a tendency to fall backwards), rigidity, stooped posture, slowness of voluntary movements, and a masklike facial expression. Pathologic features include loss of melanin containing neurons in the substantia nigra and other pigmented nuclei of the brainstem. LEWY BODIES are present in the substantia nigra and locus coeruleus but may also be found in a related condition (LEWY BODY DISEASE, DIFFUSE) characterized by dementia in combination with varying degrees of parkinsonism. (Adams et al., Principles of Neurology, 6th ed, p1059, pp1067-75)	2.08	1	0
Schizophrenia A severe emotional disorder of psychotic depth characteristically marked by a retreat from reality with delusion formation, HALLUCINATIONS, emotional disharmony, and regressive behavior.	2.08	1	0
Anxiety Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.	2.1	1	0
Cardiometabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components not only include metabolic dysfunctions of METABOLIC SYNDROME but also HYPERTENSION, and ABDOMINAL OBESITY.	2.11	1	0
Dyslipidemia [description not available]	2.11	1	0
Diabetes Mellitus, Adult-Onset [description not available]	2.11	1	0
Blood Pressure, High [description not available]	2.11	1	0
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.	2.11	1	0
Hypertension Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.	2.11	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).	2.11	1	0
Metabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components of metabolic syndrome include ABDOMINAL OBESITY; atherogenic DYSLIPIDEMIA; HYPERTENSION; HYPERGLYCEMIA; INSULIN RESISTANCE; a proinflammatory state; and a prothrombotic (THROMBOSIS) state.	2.11	1	0
Dyslipidemias Abnormalities in the serum levels of LIPIDS, including overproduction or deficiency. Abnormal serum lipid profiles may include high total CHOLESTEROL, high TRIGLYCERIDES, low HIGH DENSITY LIPOPROTEIN CHOLESTEROL, and elevated LOW DENSITY LIPOPROTEIN CHOLESTEROL.	2.11	1	0
Cardiac Hypertrophy Enlargement of the HEART due to chamber HYPERTROPHY, an increase in wall thickness without an increase in the number of cells (MYOCYTES, CARDIAC). It is the result of increase in myocyte size, mitochondrial and myofibrillar mass, as well as changes in extracellular matrix.	7.13	1	0
Cardiomegaly Enlargement of the HEART, usually indicated by a cardiothoracic ratio above 0.50. Heart enlargement may involve the right, the left, or both HEART VENTRICLES or HEART ATRIA. Cardiomegaly is a nonspecific symptom seen in patients with chronic systolic heart failure (HEART FAILURE) or several forms of CARDIOMYOPATHIES.	2.13	1	0
Triploid [description not available]	7.13	1	0
Extravascular Hemolysis [description not available]	2.13	1	0
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	2.13	1	0
Disease Resistance The capacity of an organism to defend itself against pathological processes or the agents of those processes. This most often involves innate immunity whereby the organism responds to pathogens in a generic way. The term disease resistance is used most frequently when referring to plants.	2.15	1	0
Electrolytes Substances that dissociate into two or more ions, to some extent, in water. Solutions of electrolytes thus conduct an electric current and can be decomposed by it (ELECTROLYSIS). (Grant & Hackh's Chemical Dictionary, 5th ed)	2.04	1	0
Hay Fever [description not available]	2.05	1	0
Rhinitis, Allergic, Seasonal Allergic rhinitis that occurs at the same time every year. It is characterized by acute CONJUNCTIVITIS with lacrimation and ITCHING, and regarded as an allergic condition triggered by specific ALLERGENS.	2.05	1	0
Infections, Plasmodium [description not available]	4.12	17	0
Malaria A protozoan disease caused in humans by four species of the PLASMODIUM genus: PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PLASMODIUM OVALE; and PLASMODIUM MALARIAE; and transmitted by the bite of an infected female mosquito of the genus ANOPHELES. Malaria is endemic in parts of Asia, Africa, Central and South America, Oceania, and certain Caribbean islands. It is characterized by extreme exhaustion associated with paroxysms of high FEVER; SWEATING; shaking CHILLS; and ANEMIA. Malaria in ANIMALS is caused by other species of plasmodia.	4.12	17	0
Plasmodium vivax Malaria [description not available]	1.92	1	0
Malaria, Vivax Malaria caused by PLASMODIUM VIVAX. This form of malaria is less severe than MALARIA, FALCIPARUM, but there is a higher probability for relapses to occur. Febrile paroxysms often occur every other day.	1.92	1	0
Genome Instability [description not available]	2.05	1	0
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	2.47	2	0
Fish Diseases Diseases of freshwater, marine, hatchery or aquarium fish. This term includes diseases of both teleosts (true fish) and elasmobranchs (sharks, rays and skates).	2.4	2	0
Atypical Mycobacterial Infection, Disseminated [description not available]	2.06	1	0
Diathesis [description not available]	3.86	2	1
Chromosome-Defective Micronuclei [description not available]	2.46	2	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.9	4	0
Arsenic Encephalopathy [description not available]	2.01	1	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.01	1	0
Trypanosomiasis Infection with protozoa of the genus TRYPANOSOMA.	3.02	5	0
Bovine Diseases [description not available]	2.33	2	0
Sarcoma, Epithelioid [description not available]	1.93	1	0
EHS Tumor [description not available]	2.84	4	0
Sarcoma A connective tissue neoplasm formed by proliferation of mesodermal cells; it is usually highly malignant.	1.93	1	0
Experimental Neoplasms [description not available]	4.56	10	0
Sarcoma 37 An experimental sarcoma of mice.	6.93	1	0
African Sleeping Sickness [description not available]	1.93	1	0
Trypanosomiasis, African A disease endemic among people and animals in Central Africa. It is caused by various species of trypanosomes, particularly T. gambiense and T. rhodesiense. Its second host is the TSETSE FLY. Involvement of the central nervous system produces African sleeping sickness. Nagana is a rapidly fatal trypanosomiasis of horses and other animals.	1.93	1	0
Sarcoma 180 An experimental sarcoma of mice.	6.93	1	0
Infection [description not available]	1.93	1	0
Infections Invasion of the host organism by microorganisms or their toxins or by parasites that can cause pathological conditions or diseases.	1.93	1	0
Cough A sudden, audible expulsion of air from the lungs through a partially closed glottis, preceded by inhalation. It is a protective response that serves to clear the trachea, bronchi, and/or lungs of irritants and secretions, or to prevent aspiration of foreign materials into the lungs.	1.93	1	0
Abscess, Amebic [description not available]	4.13	17	0
Amebiasis, Intestinal [description not available]	4.01	15	0
Amebiasis Infection with any of various amebae. It is an asymptomatic carrier state in most individuals, but diseases ranging from chronic, mild diarrhea to fulminant dysentery may occur.	4.13	17	0
Leucocythaemia [description not available]	1.93	1	0
Granulocytic Leukemia [description not available]	1.93	1	0
Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)	6.93	1	0
Leukemia, Myeloid Form of leukemia characterized by an uncontrolled proliferation of the myeloid lineage and their precursors (MYELOID PROGENITOR CELLS) in the bone marrow and other sites.	1.93	1	0
Dehydration The condition that results from excessive loss of water from a living organism.	6.93	1	0
Breast Cancer [description not available]	1.93	1	0
Breast Neoplasms Tumors or cancer of the human BREAST.	1.93	1	0
Experimental Leukemia [description not available]	1.93	1	0
Disorders, Sex Chromosome [description not available]	1.93	1	0
Autosomal Hemophilia A [description not available]	1.93	1	0
Hemophilia A The classic hemophilia resulting from a deficiency of factor VIII. It is an inherited disorder of blood coagulation characterized by a permanent tendency to hemorrhage.	1.93	1	0
Fistula Abnormal communication most commonly seen between two internal organs, or between an internal organ and the surface of the body.	1.93	1	0
Weight Gain Increase in BODY WEIGHT over existing weight.	6.93	1	0
Ascites Accumulation or retention of free fluid within the peritoneal cavity.	6.93	1	0
Hepatocellular Carcinoma [description not available]	2.85	1	0
Cancer of Liver [description not available]	2.85	1	0
Germinoblastoma [description not available]	2.85	1	0
Animal Mammary Carcinoma [description not available]	2.85	1	0
Experimental Mammary Neoplasms [description not available]	2.85	1	0
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	2.85	1	0
Liver Neoplasms Tumors or cancer of the LIVER.	2.85	1	0
Lymphoma A general term for various neoplastic diseases of the lymphoid tissue.	2.85	1	0
Koch's Disease [description not available]	2.36	2	0
Tuberculosis Any of the infectious diseases of man and other animals caused by species of MYCOBACTERIUM TUBERCULOSIS.	2.36	2	0
Balkan Endemic Nephropathy [description not available]	2.03	1	0
Starvation Lengthy and continuous deprivation of food. (Stedman, 25th ed)	2.03	1	0
Liver Dysfunction [description not available]	1.96	1	0
Liver Diseases Pathological processes of the LIVER.	1.96	1	0
Cocarcinogenesis The combination of two or more different factors in the production of cancer.	1.96	1	0
Cancer of Mouth [description not available]	1.96	1	0
Mouth Neoplasms Tumors or cancer of the MOUTH.	1.96	1	0
Leukemia P388 An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.	1.98	1	0
Diseases, Occupational [description not available]	1.99	1	0

phenanthrene

Description

Cross-References

Synonyms (83)

Research Excerpts

Overview

Effects

Treatment

Toxicity

Compound-Compound Interactions

Bioavailability

Dosage Studied

Roles (2)

Drug Classes (3)

Protein Targets (25)

Potency Measurements

Inhibition Measurements

Biological Processes (6)

Molecular Functions (6)

Ceullar Components (4)

Bioassays (52)

Research

Studies (2,003)

Market Indicators

Research Demand Index: 66.58

Study Types

phenanthrene

Description

Cross-References

Synonyms (83)

Research Excerpts

Overview

Effects

Treatment

Toxicity

Compound-Compound Interactions

Bioavailability

Dosage Studied

Roles (2)

Drug Classes (3)

Protein Targets (25)

Potency Measurements

Inhibition Measurements

Biological Processes (6)

Molecular Functions (6)

Ceullar Components (4)

Bioassays (52)

Research

Studies (2,003)

Market Indicators

Research Demand Index: 66.58

Study Types

Related Drugs (704)

Related Conditions (131)