fumaric acid profile

fumaric acid: see also record for ferrous fumarate; use FUMARATES for general fumaric acid esters [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

fumaric acid : A butenedioic acid in which the C=C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle. [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	444972
CHEMBL ID	503160
CHEBI ID	18012
CHEBI ID	22958
SCHEMBL ID	1177
MeSH ID	M0100168

Synonym
6915-18-0
LS-12976
bdbm26122
fumarate, 10
allomaleic acid
1, (e)
nsc2752 ,
kyselina fumarova
wln: qv1u1vq-t
butenedioic acid, (e)-
trans-1,2-ethylenedicarboxylic acid
nsc-2752
tumaric acid
2-butenedioic acid (e)-
boletic acid
u-1149
lichenic acid
2-butenedioic acid, (e)-
usaf ek-p-583
(2e)-2-butenedioic acid
(2e)-but-2-enedioate
trans-but-2-enedioic acid
fumarsaeure
e297
(e)-2-butenedioic acid
CHEBI:18012 ,
(e)-butenedioic acid
trans-1,2-ethenedicarboxylic acid
trans-1,2-ethylenediccarboxylic acid
(e)-1,2-ethylenedicarboxylic acid
butenedioic acid
CHEBI:22958
but-2-enedioic acid
kyselina fumarova [czech]
brn 0605763
lichenic acid (van)
einecs 203-743-0
(2e)-but-2-enedioic acid
2-butenedioic acid, (2e)-
allomalenic acid
1,2-ethenedicarboxylic acid, trans-
2-butenedioic acid (2e)- (9ci)
fema no. 2488
hsdb 710
ai3-24236
trans-2-butenedioic acid
epa pesticide chemical code 051201
2-(e)-butenedioic acid
fc 33
fema number 2488
2-butenedioic acid (2e)-
caswell no. 465e
fumaric acid (8ci)
fc 33 (acid)
ccris 1039
1,2-ethylenedicarboxylic acid, (e)
NCGC00091192-01
C00122
110-17-8
FUM ,
fumarate
fumaric acid
trans-butenedioic acid
fumaric acid, bioreagent, suitable for cell culture
fumaric acid, >=99%, fcc, fg
DB01677
fumaric acid (nf)
D02308
e-2-butenedioic acid
fumaric acid, >=99%
26B3632D-E93F-4655-90B0-3C17855294BA
(e)-but-2-enedioic acid
AKOS000118896
MLS002454406
smr000112117
BMSE000083
F0067 ,
ins-297
allomaleic-acid
CHEMBL503160
e-297
boletic-acid
ins no.297
fumaricum acidum
NCGC00091192-03
ethylenedicarboxylic acid
88xhz13131 ,
4-02-00-02202 (beilstein handbook reference)
ec 203-743-0
fumaric acid [nf]
unii-88xhz13131
NCGC00256360-01
dtxsid3021518 ,
dtxcid601518
tox21_302826
cas-110-17-8
NCGC00259318-01
tox21_201769
pharmakon1600-01301022
nsc760395
nsc-760395
HMS2270C12
donitic acid
BP-13087
fumaric acid [usp-rs]
fumaric acid [hsdb]
fumaric acid [ii]
fumaric acid [mart.]
sodium aurothiomalate impurity b [ep impurity]
fumaricum acidum [hpus]
fumaric acid [who-dd]
623158-97-4
fumaric acid [mi]
fumaric acid [inci]
fumaric acid [fhfi]
fumaric acid [usp impurity]
malic acid impurity a [ep impurity]
fumaric acid [vandf]
fumaric acid [fcc]
2(trans)-butenedioic acid
S4952
SCHEMBL1177
(e)-2-butenedioate
fumeric acid
(trans)-butenedioic acid
(2e)-2-butenedioic acid #
but-2-enedioicacid
mfcd00002700
F8886-8257
J-002389
fumaric acid, certified reference material, tracecert(r)
fumaric acid, anhydrous, free-flowing, redi-dri(tm), >=99%
maleic-2,3-d2 acid
fumaric acid, puriss., >=99.5% (t)
fumaric acid, united states pharmacopeia (usp) reference standard
fumaric acid, >=99.0% (t)
fumaric acid, tested according to usp/nf
fumaric acid, 99%
fumaric acid, european pharmacopoeia (ep) reference standard
fumaric acid, vetec(tm) reagent grade, 99%
fumaric acid, pharmaceutical secondary standard; certified reference material
fumaric acid, qnmr standard for dmso
2-(e)-butenedioate
trans-2-butenedioate
trans-butenedioate
trans-1,2-ethylenedicarboxylate
allomaleate
lichenate
boletate
HY-W015883
CS-W016599
fumaric acid,(s)
Q139857
STR02646
AMY30339
CCG-266065
futrans-2-butenedioic acid
D85166
fumaric acid 1000 microg/ml in acetonitrile:water
fumarate; 2-butenedioic acid; trans-butenedioic acid
EN300-17996
fumarsaure
fumaric acid (usp-rs)
fumaric acid (mart.)
acido trans butendioico
usepa/opp pesticide code: 051201
acido allomaleico
malic acid impurity a (ep impurity)
fema number: 2488
fumaric acid (ii)
acido lichenico
sodium aurothiomalate impurity b (ep impurity)
acido trans 1,2-etenedicarbossilico
acido fumarico
acido boletico
trans-2-butendisaure
fumaric acid (usp impurity)
1,2-ethylenedicarboxylic acid
trans-ethylendicarbonsaure
acido trans 1,2-etilendicarbossilico
Z57127460

Excerpt	Reference	Relevance
"Fumaric acid is an important building-block chemical. "	( Production of fumaric acid by immobilized Rhizopus arrhizus RH 7-13-9# on loofah fiber in a stirred-tank reactor. Deng, L; Jin, Y; Liu, H; Tan, T; Wang, F; Yue, X; Zhao, S, 2017)	2.26
"Fumaric acid is a valuable compound used in foods, beverages, detergents, animal feed, pharmaceuticals and miscellaneous industrial products. "	( Fumaric acid: production and separation. Caşcaval, D; Galaction, AI; Ilica, RA; Kloetzer, L, 2019)	3.4
"Fumaric acid is a naturally occurring organic acid that is an intermediate of the tricarboxylic acid cycle. "	( Metabolic engineering of Escherichia coli for the production of fumaric acid. Choi, S; Jang, JW; Kim, DI; Lee, SY; Song, CW, 2013)	2.07
"Fumaric acid is an intermediate product of the citric acid cycle, which is source of intracellular energy."	( Fumaric acid attenuates the eotaxin-1 expression in TNF-α-stimulated fibroblasts by suppressing p38 MAPK-dependent NF-κB signaling. Jung, E; Lee, J; Park, D; Roh, KB, 2013)	2.55
"Fumaric acid (FA) is an important raw material in the chemical and pharmaceutical industries. "	( Pull-in urea cycle for the production of fumaric acid in Escherichia coli. Deng, L; Tan, T; Wang, F; Wang, Z; Yan, Y; Zhang, T, 2015)	2.13
"Fumaric acid is an important C4-dicarboxylic acid widely used in chemical, food, and pharmaceutical industries. "	( Combining rational metabolic engineering and flux optimization strategies for efficient production of fumaric acid. Lee, SY; Song, CW, 2015)	2.08
"Fumaric acid is a commonly used excipient in pharmaceutical products. "	( Quantification of fumarate and investigation of endogenous and exogenous fumarate stability in rat plasma by LC-MS/MS. Fast, DM; Li, F; Rago, B; Shi, Y; Tse, S; Yapa, U, 2016)	1.88
"Fumaric aciduria is a rare metabolic disease, with 40 cases reported so far. "	( Fumaric aciduria: an overview and the first Brazilian case report. Allegri, G; Correia, P; de Oliveira, ML; Fernandes, MJ; Llerena, JC; Scalco, FB; Simoni, RE, 2010)	3.25
"Fumaric acid, which is an internal acidifying agent, was incorporated into the hydroxypropyl methylcellulose-based core tablets to create an acidic microenvironmental pH (pH(M))."	( Design and mechanism of on-off pulsed drug release using nonenteric polymeric systems via pH modulation. Choe, JS; Lee, BJ; Park, YM; Tran, PH; Tran, TT, 2011)	1.09
"Fumaric acid is a commercially important component of foodstuffs, pharmaceuticals and industrial materials, yet the current methods of production are unsustainable and ecologically destructive."	( Reconstruction of cytosolic fumaric acid biosynthetic pathways in Saccharomyces cerevisiae. Chen, J; Liu, L; Xu, G, 2012)	2.12
"Fumaric acid (FA) is a promising biomass-derived building-block chemical. "	( Fumaric acid production in Saccharomyces cerevisiae by in silico aided metabolic engineering. Chen, J; Chen, X; Liu, L; Xu, G; Xu, N; Zou, W, 2012)	3.26
"Fumaric acid is shown to be a competitive inhibitor of wheat germ lipoxygenase."	( Fumaric acid is a competitive inhibitor of wheat germ lipoxygenase. Popova, TN; Zherebtsov, NA; Zyablova, TV, 2000)	3.19
"Fumaric acid is a component of the tricarboxylic acid cycle and, like starch and soluble sugars, can be metabolized to yield energy and carbon skeletons for production of other compounds."	( Fumaric acid: an overlooked form of fixed carbon in Arabidopsis and other plant species. Chia, DW; Gibson, SI; Reiter, WD; Yoder, TJ, 2000)	2.47

Excerpt	Reference	Relevance
"Fumaric acid esters (FAEs) have been licensed for the systemic treatment of the immune-mediated disease psoriasis."	( Recent advances in the biomedical applications of fumaric acid and its ester derivatives: The multifaceted alternative therapeutics. Brar, SK; Das, RK; Verma, M, 2016)	1.41

Excerpt	Reference	Relevance
"Treatment with fumaric acid (50 mM for 10 min at room temperature) was the most effective, although it caused browning of the lettuce, with up to a 2-log reduction observed."	( Efficiency of sodium hypochlorite, fumaric acid, and mild heat in killing native microflora and Escherichia coli O157:H7, Salmonella typhimurium DT104, and Staphylococcus aureus attached to fresh-cut lettuce. Isshiki, K; Kondo, N; Murata, M, 2006)	0.95

Excerpt	Reference	Relevance
" The tmax was 241 min (range 60-1189 min, 95% CI 53, 781) shorter when the tablet was taken after an overnight fast (182 min; range 120-240 min; 95% CI 146, 211) than when taken with breakfast (361 min; range 240-1429 min; 95% CI 0, 1062)."	( Pharmacokinetics of oral fumarates in healthy subjects. Burggraaf, J; Litjens, NH; Mattie, H; Nibbering, PH; Schoemaker, RC; Thio, HB; van Dissel, JT; van Gulpen, C; van Strijen, E, 2004)	0.32
" Pharmacokinetic profiling of orally dosed DPG or DPG with 60% loading of FA (DPG/FA60) was carried out in omeprazole-treated rats as a hypochlorhydric model."	( Improved dissolution and pharmacokinetic behavior of dipyridamole formulation with microenvironmental pH-modifier under hypochlorhydria. Inoue, R; Kawabata, Y; Onoue, S; Taniguchi, C; Wada, K; Yamada, S; Yamashita, K; Yamauchi, Y, 2012)	0.38
" Pharmacokinetic studies on rats showed that the glutarate salt exhibits doubled plasma AUC values in a single dose within an hour compared to the citrate salt."	( Salt and cocrystals of sildenafil with dicarboxylic acids: solubility and pharmacokinetic advantage of the glutarate salt. Desiraju, GR; Ganguly, S; Sanphui, P; Tothadi, S, 2013)	0.39

Excerpt	Reference	Relevance
" The potential for use in combination with other systemic drugs has not been explored."	( Fumaric acid esters in severe psoriasis, including experience of use in combination with other systemic modalities. Balasubramaniam, P; Berth-Jones, J; Stevenson, O, 2004)	1.77
"To present data relating to the efficacy of FAE in severe psoriasis and to examine the potential dose-sparing effect and safety issues when FAE are combined with other systemic agents."	( Fumaric acid esters in severe psoriasis, including experience of use in combination with other systemic modalities. Balasubramaniam, P; Berth-Jones, J; Stevenson, O, 2004)	1.77
" Nine patients received FAE in combination with other systemic therapies including ciclosporin, acitretin, hydroxyurea and methotrexate."	( Fumaric acid esters in severe psoriasis, including experience of use in combination with other systemic modalities. Balasubramaniam, P; Berth-Jones, J; Stevenson, O, 2004)	1.77
" FAE were used successfully in combination with other systemic agents and generally enabled the doses of the more hazardous drugs to be reduced."	( Fumaric acid esters in severe psoriasis, including experience of use in combination with other systemic modalities. Balasubramaniam, P; Berth-Jones, J; Stevenson, O, 2004)	1.77
"Two trials were conducted to identify the optimal levels of essential oil active components (EOAC) and their combination with fumarate on in vitro rumen fermentation."	( In vitro rumen fermentation and methane production are influenced by active components of essential oils combined with fumarate. Liang, Q; Lin, B; Liu, JX; Lu, Y; Wang, JH, 2013)	0.39
"We collected data on frequency of use, demographics, treatment characteristics and drug survival of biologics combined with conventional systemic agents or phototherapy in five PSONET registries."	( Biologics combined with conventional systemic agents or phototherapy for the treatment of psoriasis: real-life data from PSONET registries. Addis, A; Adenubiova, E; Busard, CI; Cazzaniga, S; Cohen, AD; Feldhamer, I; Gkalpakiotis, S; Hutten, BA; Kojanova, M; Lichem, R; Naldi, L; Quehenberger, F; Spuls, PI; Stern, RS; Wolf, P, 2018)	0.48
" Longest survival on a biologic combined with methotrexate, acitretin or cyclosporin was 103, 78 and 34 months, respectively."	( Biologics combined with conventional systemic agents or phototherapy for the treatment of psoriasis: real-life data from PSONET registries. Addis, A; Adenubiova, E; Busard, CI; Cazzaniga, S; Cohen, AD; Feldhamer, I; Gkalpakiotis, S; Hutten, BA; Kojanova, M; Lichem, R; Naldi, L; Quehenberger, F; Spuls, PI; Stern, RS; Wolf, P, 2018)	0.48
"Management of drug-drug interactions (DDIs) for ensitrelvir, a novel 3-chymotrypsin-like protease inhibitor of SARS-CoV-2 infection is crucial."	( Evaluation of the Drug-Drug Interaction Potential of Ensitrelvir Fumaric Acid with Cytochrome P450 3A Substrates in Healthy Japanese Adults. Fukuhara, T; Kubota, R; Kuwata, A; Matsuo, Y; Matsuzaki, T; Shimizu, R; Sonoyama, T, 2023)	1.15
" Either dexamethasone, prednisolone, or midazolam was administered alone (Day - 2) or in combination with ensitrelvir (Day 5) in each of the cohorts."	( Evaluation of the Drug-Drug Interaction Potential of Ensitrelvir Fumaric Acid with Cytochrome P450 3A Substrates in Healthy Japanese Adults. Fukuhara, T; Kubota, R; Kuwata, A; Matsuo, Y; Matsuzaki, T; Shimizu, R; Sonoyama, T, 2023)	1.15

Excerpt	Reference	Relevance
" The results may be important for elucidating factors affecting iron bioavailability in the small intestine and for the development of foods with improved iron bioavailability."	( Organic acids influence iron uptake in the human epithelial cell line Caco-2. Andlid, T; Salovaara, S; Sandberg, AS, 2002)	0.31
"Weakly basic drugs, such as verapamil hydrochloride, that are poorly soluble in neutral/alkaline medium may have poor oral bioavailability due to reduced solubility in the small intestine and colon."	( Film coated pellets containing verapamil hydrochloride: enhanced dissolution into neutral medium. Munday, DL, 2003)	0.32
" The fumaric acid based dry granulated product demonstrated a mean bioavailability comparable to an oral solution dose in a dog model."	( Fumaric acid microenvironment tablet formulation and process development for crystalline cenicriviroc mesylate, a BCS IV compound. Dalziel, SM; Menning, MM, 2013)	2.35
" Thus, to improve solubility and bioavailability characteristics, cocrystals and salts of the drug have been prepared by treating aliphatic dicarboxylic acids with sildenafil; the N-methylated piperazine of the drug molecule interacts with the carboxyl group of the acid to form a heterosynthon."	( Salt and cocrystals of sildenafil with dicarboxylic acids: solubility and pharmacokinetic advantage of the glutarate salt. Desiraju, GR; Ganguly, S; Sanphui, P; Tothadi, S, 2013)	0.39
"The aim of the present work was to design a pH-modified solid dispersion (pH(M)-SD) that can improve the dissolution and bioavailability of poorly water-soluble weakly basic GT0918, a developing anti-prostate cancer drug."	( Microenvironmental pH-modified solid dispersions to enhance the dissolution and bioavailability of poorly water-soluble weakly basic GT0918, a developing anti-prostate cancer drug: preparation, characterization and evaluation in vivo. Fan, Y; Gao, C; Ge, Z; Gong, W; He, S; Huang, X; Shan, L; Tong, Y; Wang, Y; Yang, M, 2014)	0.4
" We hypothesized that the dissolution rate and oral bioavailability of NAF would increase through hydrogen bonding between NAF and weak acids/hydrophilic polymers."	( Naftopidil-fumaric acid interaction in a solid dispersion system: Improving the dissolution rate and oral absorption of naftopidil in rats. Byeon, JC; Choi, JS; Park, JS, 2019)	0.9
" Herein, we prepared a biodegradable super paramagnetic starch-based hydrogel grafted onto fumaric acid for increasing Quer bioavailability and controlling its release."	( Enhancing quercetin bioavailability by super paramagnetic starch-based hydrogel grafted with fumaric acid: An in vitro and in vivo study. Doosti, M; Hosseini, SH; Mousavi, SN; Rasoulifard, MH; Seyed Dorraji, MS, 2019)	0.95
" In the present work, sustained-release (SR) formulations of the PFD-FA cocrystal of two different strengths such as 200 and 600 mg were prepared and its comparative bioavailability in healthy human volunteers was studied against the reference formulation PIRFENEX (200 mg)."	( Investigating the Role of the Reduced Solubility of the Pirfenidone-Fumaric Acid Cocrystal in Sustaining the Release Rate from Its Tablet Dosage Form by Conducting Comparative Bioavailability Study in Healthy Human Volunteers. Bansal, AK; Bose, A; Chakraborty, S; Das, S; Ghosh, A; Kumari, N; Pandey, N; Parmar, PK; Roy, P; Roy, S, 2022)	0.96

Excerpt	Relevance	Reference
" Mild disturbances of liver and kidney function during treatment were observed with the 720 mg dosage of MEFAE and with the 240 mg dosage of DMFAE."	( Systemic therapy with fumaric acid derivates: new possibilities in the treatment of psoriasis. de Hoop, D; Langendijk, PN; Nieboer, C; van Dijk, E; van Loenen, AC, 1989)	0.59
"5 mg/kg) reduced the semiconservative DNA synthesis of the hepatocytes, but simultaneous dosing of fumaric acid (40 mg/kg) enhanced the recovery of the DNA synthesis."	( Fumaric acid enhances DNA synthesis of rat hepatocytes by counteracting the toxicities of mitomycin C and aflatoxin B1. Akao, M; Kuroda, K; Terao, K, 1986)	1.93
" A high fumarate level resulted in a dose-response curve linking bias and cytoplasmic CheY concentration that was offset but with a slope similar to that for a low fumarate level."	( Regulation of switching frequency and bias of the bacterial flagellar motor by CheY and fumarate. Eisenbach, M; Marwan, W; Montrone, M; Oesterhelt, D, 1998)	0.3
" The potential use of this information as a baseline dataset for future toxicological or physiological studies was demonstrated by a metabonomic analysis: a series of earthworms were dosed with the model compound 3-fluoro-4-nitrophenol, and toxic effects followed by multivariate analysis of the spectral data of the coelomic fluid."	( An NMR-based metabonomic approach to the investigation of coelomic fluid biochemistry in earthworms under toxic stress. Bundy, JG; Lindon, JC; Nicholson, JK; Osborn, D; Weeks, JM, 2001)	0.31
"Utilizing a double-blind design, 21 hospitalized adult men or women with DSM-IV schizophrenia or schizoaffective disorder, who had received unchanged doses (for 2 weeks) of either 400 or 600 mg daily of quetiapine administered in 2 doses, were randomly assigned to once- or twice-daily administration for 4 weeks and then crossed over to the opposite dosing regimen for an additional 4 weeks."	( A random-assignment, double-blind, clinical trial of once- vs twice-daily administration of quetiapine fumarate in patients with schizophrenia or schizoaffective disorder: a pilot study. Brar, JS; Chengappa, KN; Goldstein, JM; Mullen, J; Parepally, H; Shilling, A, 2003)	0.32
"These pilot data suggest that it is clinically feasible to switch most quetiapine-treated subjects receiving a therapeutic twice-daily dosing schedule to a once-daily regimen."	( A random-assignment, double-blind, clinical trial of once- vs twice-daily administration of quetiapine fumarate in patients with schizophrenia or schizoaffective disorder: a pilot study. Brar, JS; Chengappa, KN; Goldstein, JM; Mullen, J; Parepally, H; Shilling, A, 2003)	0.32
"Incorporation of pH modifiers is a commonly used strategy to enhance the dissolution rate of weakly basic drugs from sustained release solid dosage forms."	( Microenvironmental pH and microviscosity inside pH-controlled matrix tablets: an EPR imaging study. Borchert, HH; Gurny, R; Herrmann, W; Kramer, A; Lueckel, B; Ries, A; Siepe, S, 2006)	0.33
" Pharmacokinetic profiling of orally dosed DPG or DPG with 60% loading of FA (DPG/FA60) was carried out in omeprazole-treated rats as a hypochlorhydric model."	( Improved dissolution and pharmacokinetic behavior of dipyridamole formulation with microenvironmental pH-modifier under hypochlorhydria. Inoue, R; Kawabata, Y; Onoue, S; Taniguchi, C; Wada, K; Yamada, S; Yamashita, K; Yamauchi, Y, 2012)	0.38
" The drugs were used in a dosage of 2 mg/kg/day in 2 divided doses for 14 days."	( [Comparative efficacy of nitrofurans in children and adolescents with pyelonephritis in presence of crystalluria]. Aver'anova, NI; Balueva, LG; Ivanova, NV, 2013)	0.39
" Thus, this montelukast sodium-loaded oral suspension, with bioequivalence to the commercial granules and excellent stability, could be a prospective dosage form for the treatment of asthma."	( Novel montelukast sodium-loaded stable oral suspension bioequivalent to the commercial granules in rats. Cho, KH; Choi, HG; Jin, SG; Kim, DS; Kim, DW; Kim, JO; Kim, KS; Kim, YH; Kim, YI; Kwon, TK; Li, DX; Park, JH; Woo, JS; Yong, CS; Yousaf, AM, 2016)	0.43
" FADs were used at an average dosage of 361."	( Use of fumaric acid derivatives in Italian reference centers for psoriasis. Cazzaniga, S; Damiani, G; Naldi, L, 2021)	1.08
"Orally dosed drugs must dissolve in the gastrointestinal (GI) tract before being absorbed through the epithelial cell membrane."	( Improving Dissolution Behavior and Oral Absorption of Drugs with pH-Dependent Solubility Using pH Modifiers: A Physiologically Realistic Mass Transport Analysis. Al-Gousous, J; Amidon, GE; Amidon, GL; Greenwood, DE; Kuminek, G; Salehi, N; Sperry, DC; Waltz, NM; Ziff, RM, 2021)	0.62
" The recommended daily dosage of PFD in patients with IPF is very high (2403 mg/day) and must be mitigated through additives."	( Investigating the Role of the Reduced Solubility of the Pirfenidone-Fumaric Acid Cocrystal in Sustaining the Release Rate from Its Tablet Dosage Form by Conducting Comparative Bioavailability Study in Healthy Human Volunteers. Bansal, AK; Bose, A; Chakraborty, S; Das, S; Ghosh, A; Kumari, N; Pandey, N; Parmar, PK; Roy, P; Roy, S, 2022)	0.96

Item	Process	Frequency
Snacks	core-ingredient	731
Sweet snacks	core-ingredient	704
Confectioneries	core-ingredient	695
Plant-based foods and beverages	core-ingredient	456
Beverages	core-ingredient	370
Plant-based beverages	core-ingredient	322
Plant-based foods	core-ingredient	132
Candies	core-ingredient	124
Cereals and potatoes	core-ingredient	109
Breads	core-ingredient	100
Mexican Dinner Mixes	core-ingredient	94
Gummi candies	core-ingredient	54
Meals	core-ingredient	40
Pizzas	core-ingredient	35
Pizzas pies and quiches	core-ingredient	33
Groceries	core-ingredient	29
Condiments	core-ingredient	29
Dried products to be rehydrated	core-ingredient	28
Dried products	core-ingredient	28
Sauces	core-ingredient	27
Dehydrated beverages	core-ingredient	27
Fruit-based beverages	core-ingredient	26
Jelly beans	core-ingredient	24
Desserts	core-ingredient	18
Special breads	core-ingredient	18
Flatbreads	core-ingredient	16
Gelatin	core-ingredient	14
Thickeners	core-ingredient	13
Food additives	core-ingredient	13
Gummy bears	core-ingredient	12
Sodas	core-ingredient	12
Carbonated drinks	core-ingredient	12
Fruit and vegetable preserves	core-ingredient	12
Sweet spreads	core-ingredient	12
Plant-based spreads	core-ingredient	12
Spreads	core-ingredient	12
Breakfasts	core-ingredient	12
Pie dough	core-ingredient	10
Cereals and their products	core-ingredient	10
Juices and nectars	core-ingredient	10
Jelly desserts	core-ingredient	10
Wheat breads	core-ingredient	10
Cooking helpers	core-ingredient	9
Biscuits and cakes	core-ingredient	9
Sandwiches	core-ingredient	9
White breads	core-ingredient	9
Fruit juices	core-ingredient	8
Fruits and vegetables based foods	core-ingredient	8
English muffins	core-ingredient	8
Frozen foods	core-ingredient	7
Cakes	core-ingredient	7
Dessert mixes	core-ingredient	6
Cranberry juices	core-ingredient	6
Fruits based foods	core-ingredient	6
Wheat flatbreads	core-ingredient	6
Licensed products	core-ingredient	6
Pitas	core-ingredient	5
Acid gummy candies	core-ingredient	5
Pains	core-ingredient	5
Céréales et pommes de terre	core-ingredient	5
Aliments d'origine végétale	core-ingredient	5
Aliments et boissons à base de végétaux	core-ingredient	5
Pastry helpers	core-ingredient	4
Iced teas	core-ingredient	4
Tea-based beverages	core-ingredient	4
Specific products	core-ingredient	4
tortillas	core-ingredient	4
Pepperoni pizzas	core-ingredient	4
Sugar-free chewing gum	core-ingredient	3
Vitamins	core-ingredient	3
Dietary supplements	core-ingredient	3
Canned fruits	core-ingredient	3
Canned plant-based foods	core-ingredient	3
Canned foods	core-ingredient	3
en:candies	core-ingredient	3
Crisps	core-ingredient	3
Chips and fries	core-ingredient	3
Appetizers	core-ingredient	3
Salty snacks	core-ingredient	3
Alcoholic beverages	core-ingredient	3
Pains plats	core-ingredient	3
Cheese pizzas	core-ingredient	3
Gummy cola bottles	core-ingredient	3
Frozen seafood	core-ingredient	2
Seafood	core-ingredient	2
Cake mixes	core-ingredient	2
Baking Mixes	core-ingredient	2
Hot sauces	core-ingredient	2
Chewing gum	core-ingredient	2
Beverages with cranberry	core-ingredient	2
Waters	core-ingredient	2
Mandarin oranges	core-ingredient	2
Citrus	core-ingredient	2
Fruits	core-ingredient	2
Tortillas de blé	core-ingredient	2
Pains de blé	core-ingredient	2
Pains blancs	core-ingredient	2
Meal kits	core-ingredient	2
Naans	core-ingredient	2
Wraps	core-ingredient	2
Corn chips	core-ingredient	2
Mixes for jelly desserts	core-ingredient	2
Whole-wheat English muffins	core-ingredient	2
Marshmallows	core-ingredient	2
Pastries	core-ingredient	2
Vegetarian pizzas	core-ingredient	2
Corn flatbreads	core-ingredient	2
Baking decorations	core-ingredient	1
Non-dairy desserts	core-ingredient	1
Dairy substitutes	core-ingredient	1
Pizza Crust	core-ingredient	1
Daily multivitamin	core-ingredient	1
Artificially sweetened beverages	core-ingredient	1
Grape juices	core-ingredient	1
Juice Drinks	core-ingredient	1
Cotton candy	core-ingredient	1
Dips	core-ingredient	1
Stews	core-ingredient	1
Potato crisps	core-ingredient	1
Lemon meringue pies	core-ingredient	1
Lemon tarts	core-ingredient	1
Pies	core-ingredient	1
Fruit tarts	core-ingredient	1
Sweet pies	core-ingredient	1
Jello	core-ingredient	1
en:Tortillas	core-ingredient	1
hu:rágógumi	core-ingredient	1
Farines	core-ingredient	1
Muffins anglais au blé entier	core-ingredient	1
Mandarins-in-orange-gel	core-ingredient	1
Whole grain English muffins	core-ingredient	1
Bagel breads	core-ingredient	1
Pains Bagel	core-ingredient	1
Pains spéciaux	core-ingredient	1
Crust	core-ingredient	1
gela	core-ingredient	1
fruity candy	core-ingredient	1
Sweetened beverages	core-ingredient	1
Torillas	core-ingredient	1
Mixed vegetables	core-ingredient	1
Vegetables based foods	core-ingredient	1
en:open-beauty-facts	core-ingredient	1
Lollipops	core-ingredient	1
Bakery	core-ingredient	1
Salted snacks	core-ingredient	1
en:food-additives	core-ingredient	1
Muffins	core-ingredient	1
Confiseries	core-ingredient	1
sucrés	core-ingredient	1
Gelatina	core-ingredient	1
Gelificantes	core-ingredient	1
Aditivos alimentarios	core-ingredient	1
Tortillas de maïs	core-ingredient	1
Minestrone soups	core-ingredient	1
Soups	core-ingredient	1
Energy drinks	core-ingredient	1
Tandoori Baked Naan bread	core-ingredient	1
Chicken wraps	core-ingredient	1
Burritos	core-ingredient	1
sald	core-ingredient	1
Rūgštūs guminukai	core-ingredient	1
Guminukai	core-ingredient	1
Saldainiai	core-ingredient	1
Saldumynai	core-ingredient	1
Saldūs užkandžiai	core-ingredient	1
Užkandžiai	core-ingredient	1
Open Beauty Facts	core-ingredient	1
Non food products	core-ingredient	1
Biscuits	core-ingredient	1
Trifles	core-ingredient	1
Fruit cakes	core-ingredient	1
Sour snakes	core-ingredient	1
Fruit-flavoured beverages	core-ingredient	1

Role	Description
food acidity regulator	A food additive that is used to change or otherwise control the acidity or alkalinity of foods. They may be acids, bases, neutralising agents or buffering agents.
fundamental metabolite	Any metabolite produced by all living cells.
geroprotector	Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
[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
butenedioic acid
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathway	Proteins	Compounds
Metabolism	1496	1108
The citric acid (TCA) cycle and respiratory electron transport	147	56
Pyruvate metabolism and Citric Acid (TCA) cycle	41	46
Citric acid cycle (TCA cycle)	18	27
Alanine,Aspartic acid and Asparagine metabolism ( Alanine,Aspartic acid and Asparagine metabolism )	22	37
L-Arginino-succinic acid = L-Arginine + Fumaric acid ( Citrate cycle )	1	3
Adenylo-succinic acid = AMP + Fumaric acid ( Purine nucleotides and Nucleosides metabolism )	1	3
Succinic acid + Ubiquinone = Fumaric acid + Ubiquinol ( Tyrosine metabolism )	2	4
(S)-Malic acid = Fumaric acid + H2O ( Tyrosine metabolism )	1	3
Arginine and Proline metabolism ( Arginine and Proline metabolism )	42	55
Citrate cycle ( Citrate cycle )	21	29
Purine nucleotides and Nucleosides metabolism ( Purine nucleotides and Nucleosides metabolism )	105	77
5'-Phospho-ribosyl-4-(N-succino-carboxamide)-5-amino-imidazole = 5'-Phospho-ribosyl-4-carboxamido-5-amino-imidazole + Fumaric acid ( Purine nucleotides and Nucleosides metabolism )	1	3
Tyrosine metabolism ( Tyrosine metabolism )	28	41
Amino acid metabolism pathway excerpt: histidine catabolism extension	0	16
TCA cycle (plant)	1	21
Metabolic Epileptic Disorders	25	89
superpathway of histidine, purine and pyrimidine biosynthesis	0	31
aerobic respiration (cyanide insensitive, alternative oxidase) -- electron donors	0	6
TCA cycle, aerobic respiration	0	20
glutamine degradation	0	7
aerobic respiration (cyanide sensitive) -- electron donors	0	6
Central carbon metabolism	0	19
TCA cycle	0	10
Principal pathways of carbon metabolism	0	7
Primary carbon metabolism	23	30
Krebs cycle	1	10
TCA cycle (Krebs cycle)	30	19
AtMetExpress overview	0	109
Alanine and aspartate metabolism	0	15
TCA cycle and deficiency of pyruvate dehydrogenase complex (PDHc)	0	15
Metabolism overview	0	78
Biochemical pathways: part I	0	466
Amino acid metabolism	0	94
Krebs cycle disorders	12	14
Type 2 papillary renal cell carcinoma	0	3
Metabolic reprogramming in colon cancer	0	29
Urea cycle and metabolism of amino groups	21	16
TCA cycle (aka Krebs or citric acid cycle)	0	24
TCA cycle (plant)	7	21
tyrosine degradation I	2	12
The tricarboxylic acid cycle	4	22

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASE	Homo sapiens (human)	Potency	39.8107	0.0032	45.4673	12,589.2998	AID2517
ATAD5 protein, partial	Homo sapiens (human)	Potency	32.6294	0.0041	10.8903	31.5287	AID504467
AR protein	Homo sapiens (human)	Potency	72.3733	0.0002	21.2231	8,912.5098	AID743042
thyroid stimulating hormone receptor	Homo sapiens (human)	Potency	3.9811	0.0013	18.0743	39.8107	AID926; AID938
glucocorticoid receptor [Homo sapiens]	Homo sapiens (human)	Potency	25.9046	0.0002	14.3764	60.0339	AID720691
estrogen nuclear receptor alpha	Homo sapiens (human)	Potency	31.5217	0.0002	29.3054	16,493.5996	AID743075; AID743077; AID743079
peroxisome proliferator activated receptor gamma	Homo sapiens (human)	Potency	61.6524	0.0010	19.4141	70.9645	AID743191
aryl hydrocarbon receptor	Homo sapiens (human)	Potency	72.3733	0.0007	23.0674	1,258.9301	AID743122
chromobox protein homolog 1	Homo sapiens (human)	Potency	3.1623	0.0060	26.1688	89.1251	AID540317
nuclear factor erythroid 2-related factor 2 isoform 1	Homo sapiens (human)	Potency	16.7628	0.0006	27.2152	1,122.0200	AID651741; AID743202; AID743219
geminin	Homo sapiens (human)	Potency	0.9200	0.0046	11.3741	33.4983	AID624297
[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)
Lysine-specific demethylase 4E	Homo sapiens (human)	IC50 (µMol)	1,600.0000	0.2000	1.9569	6.3096	AID1798635
Solute carrier family 22 member 20	Mus musculus (house mouse)	Ki	30,811.4004	1.1000	6.6789	9.1201	AID360149
Prolyl 4-hydroxylase	Paramecium bursaria Chlorella virus 1	IC50 (µMol)	1,000.0000	5.0000	6.2667	8.5000	AID1543452
Solute carrier family 22 member 6	Mus musculus (house mouse)	Ki	613.2975	0.4074	5.0217	9.4000	AID360150
Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens (human)	IC50 (µMol)	150.0000	3.0000	6.1000	9.8000	AID734755
Egl nine homolog 1	Homo sapiens (human)	IC50 (µMol)	119.5000	0.0070	1.8614	8.0000	AID344926; AID721523
[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)
Egl nine homolog 1	Homo sapiens (human)	Kd	200.0000	0.4200	1.9586	3.4000	AID721525
Methyl-accepting chemotaxis protein NahY	Pseudomonas putida	Kd	17.0000	8.5000	8.5000	8.5000	AID1799787
[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)
Carbonic anhydrase 1	Homo sapiens (human)	Kinact	395.0000	0.0100	0.9387	8.6000	AID456398
Carbonic anhydrase 2	Homo sapiens (human)	Kinact	10.5000	0.0030	0.7946	10.0000	AID456397
Carbonic anhydrase 5A, mitochondrial	Homo sapiens (human)	Kinact	0.0970	0.0200	0.8580	9.4000	AID456399
Carbonic anhydrase 5B, mitochondrial	Homo sapiens (human)	Kinact	0.0900	0.0090	0.9231	9.0400	AID456400
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
regulation of gene expression	Lysine-specific demethylase 4E	Homo sapiens (human)
chromatin remodeling	Lysine-specific demethylase 4E	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 1	Homo sapiens (human)
morphogenesis of an epithelium	Carbonic anhydrase 2	Homo sapiens (human)
positive regulation of synaptic transmission, GABAergic	Carbonic anhydrase 2	Homo sapiens (human)
positive regulation of cellular pH reduction	Carbonic anhydrase 2	Homo sapiens (human)
angiotensin-activated signaling pathway	Carbonic anhydrase 2	Homo sapiens (human)
regulation of monoatomic anion transport	Carbonic anhydrase 2	Homo sapiens (human)
secretion	Carbonic anhydrase 2	Homo sapiens (human)
regulation of intracellular pH	Carbonic anhydrase 2	Homo sapiens (human)
neuron cellular homeostasis	Carbonic anhydrase 2	Homo sapiens (human)
positive regulation of dipeptide transmembrane transport	Carbonic anhydrase 2	Homo sapiens (human)
regulation of chloride transport	Carbonic anhydrase 2	Homo sapiens (human)
carbon dioxide transport	Carbonic anhydrase 2	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 2	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 5A, mitochondrial	Homo sapiens (human)
pyruvate metabolic process	NADP-dependent malic enzyme, mitochondrial	Homo sapiens (human)
malate metabolic process	NADP-dependent malic enzyme, mitochondrial	Homo sapiens (human)
aerobic respiration	NADP-dependent malic enzyme, mitochondrial	Homo sapiens (human)
oxygen metabolic process	NADP-dependent malic enzyme, mitochondrial	Homo sapiens (human)
temperature homeostasis	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens (human)
DNA alkylation repair	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens (human)
regulation of lipid storage	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens (human)
snRNA processing	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens (human)
regulation of multicellular organism growth	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens (human)
RNA repair	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens (human)
regulation of respiratory system process	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens (human)
adipose tissue development	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens (human)
mRNA destabilization	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens (human)
regulation of white fat cell proliferation	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens (human)
regulation of brown fat cell differentiation	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens (human)
response to hypoxia	Egl nine homolog 1	Homo sapiens (human)
intracellular iron ion homeostasis	Egl nine homolog 1	Homo sapiens (human)
intracellular oxygen homeostasis	Egl nine homolog 1	Homo sapiens (human)
negative regulation of DNA-binding transcription factor activity	Egl nine homolog 1	Homo sapiens (human)
regulation of angiogenesis	Egl nine homolog 1	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Egl nine homolog 1	Homo sapiens (human)
negative regulation of cyclic-nucleotide phosphodiesterase activity	Egl nine homolog 1	Homo sapiens (human)
cardiac muscle tissue morphogenesis	Egl nine homolog 1	Homo sapiens (human)
heart trabecula formation	Egl nine homolog 1	Homo sapiens (human)
ventricular septum morphogenesis	Egl nine homolog 1	Homo sapiens (human)
labyrinthine layer development	Egl nine homolog 1	Homo sapiens (human)
response to nitric oxide	Egl nine homolog 1	Homo sapiens (human)
regulation of modification of postsynaptic structure	Egl nine homolog 1	Homo sapiens (human)
regulation protein catabolic process at postsynapse	Egl nine homolog 1	Homo sapiens (human)
peptidyl-proline hydroxylation to 4-hydroxy-L-proline	Egl nine homolog 1	Homo sapiens (human)
cellular response to hypoxia	Egl nine homolog 1	Homo sapiens (human)
response to bacterium	Carbonic anhydrase 5B, mitochondrial	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 5B, mitochondrial	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
metal ion binding	Lysine-specific demethylase 4E	Homo sapiens (human)
histone H3K9me2/H3K9me3 demethylase activity	Lysine-specific demethylase 4E	Homo sapiens (human)
histone H3K9 demethylase activity	Lysine-specific demethylase 4E	Homo sapiens (human)
arylesterase activity	Carbonic anhydrase 1	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 1	Homo sapiens (human)
protein binding	Carbonic anhydrase 1	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 1	Homo sapiens (human)
hydro-lyase activity	Carbonic anhydrase 1	Homo sapiens (human)
cyanamide hydratase activity	Carbonic anhydrase 1	Homo sapiens (human)
arylesterase activity	Carbonic anhydrase 2	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 2	Homo sapiens (human)
protein binding	Carbonic anhydrase 2	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 2	Homo sapiens (human)
cyanamide hydratase activity	Carbonic anhydrase 2	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 5A, mitochondrial	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 5A, mitochondrial	Homo sapiens (human)
malic enzyme activity	NADP-dependent malic enzyme, mitochondrial	Homo sapiens (human)
malate dehydrogenase (decarboxylating) (NADP+) activity	NADP-dependent malic enzyme, mitochondrial	Homo sapiens (human)
oxaloacetate decarboxylase activity	NADP-dependent malic enzyme, mitochondrial	Homo sapiens (human)
metal ion binding	NADP-dependent malic enzyme, mitochondrial	Homo sapiens (human)
NAD binding	NADP-dependent malic enzyme, mitochondrial	Homo sapiens (human)
NADP+ binding	NADP-dependent malic enzyme, mitochondrial	Homo sapiens (human)
ferrous iron binding	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens (human)
transferase activity	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens (human)
oxidative RNA demethylase activity	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens (human)
broad specificity oxidative DNA demethylase activity	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens (human)
mRNA N6-methyladenosine dioxygenase activity	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens (human)
tRNA demethylase activity	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens (human)
protein binding	Egl nine homolog 1	Homo sapiens (human)
ferrous iron binding	Egl nine homolog 1	Homo sapiens (human)
2-oxoglutarate-dependent dioxygenase activity	Egl nine homolog 1	Homo sapiens (human)
enzyme binding	Egl nine homolog 1	Homo sapiens (human)
L-ascorbic acid binding	Egl nine homolog 1	Homo sapiens (human)
peptidyl-proline dioxygenase activity	Egl nine homolog 1	Homo sapiens (human)
hypoxia-inducible factor-proline dioxygenase activity	Egl nine homolog 1	Homo sapiens (human)
peptidyl-proline 4-dioxygenase activity	Egl nine homolog 1	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 5B, mitochondrial	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 5B, mitochondrial	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
nucleus	Lysine-specific demethylase 4E	Homo sapiens (human)
nucleoplasm	Lysine-specific demethylase 4E	Homo sapiens (human)
chromatin	Lysine-specific demethylase 4E	Homo sapiens (human)
nucleus	Lysine-specific demethylase 4E	Homo sapiens (human)
cytosol	Carbonic anhydrase 1	Homo sapiens (human)
extracellular exosome	Carbonic anhydrase 1	Homo sapiens (human)
cytoplasm	Carbonic anhydrase 2	Homo sapiens (human)
cytosol	Carbonic anhydrase 2	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 2	Homo sapiens (human)
myelin sheath	Carbonic anhydrase 2	Homo sapiens (human)
apical part of cell	Carbonic anhydrase 2	Homo sapiens (human)
extracellular exosome	Carbonic anhydrase 2	Homo sapiens (human)
cytoplasm	Carbonic anhydrase 2	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 2	Homo sapiens (human)
apical part of cell	Carbonic anhydrase 2	Homo sapiens (human)
mitochondrial matrix	Carbonic anhydrase 5A, mitochondrial	Homo sapiens (human)
mitochondrion	Carbonic anhydrase 5A, mitochondrial	Homo sapiens (human)
cytoplasm	Carbonic anhydrase 5A, mitochondrial	Homo sapiens (human)
mitochondrion	Carbonic anhydrase 5A, mitochondrial	Homo sapiens (human)
mitochondrion	NADP-dependent malic enzyme, mitochondrial	Homo sapiens (human)
mitochondrial matrix	NADP-dependent malic enzyme, mitochondrial	Homo sapiens (human)
mitochondrion	NADP-dependent malic enzyme, mitochondrial	Homo sapiens (human)
nucleus	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens (human)
nucleoplasm	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens (human)
cytoplasm	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens (human)
cytosol	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens (human)
plasma membrane	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens (human)
nuclear speck	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens (human)
intracellular membrane-bounded organelle	Alpha-ketoglutarate-dependent dioxygenase FTO	Homo sapiens (human)
cytoplasm	Egl nine homolog 1	Homo sapiens (human)
cytosol	Egl nine homolog 1	Homo sapiens (human)
postsynaptic density	Egl nine homolog 1	Homo sapiens (human)
intracellular membrane-bounded organelle	Egl nine homolog 1	Homo sapiens (human)
glutamatergic synapse	Egl nine homolog 1	Homo sapiens (human)
nucleus	Egl nine homolog 1	Homo sapiens (human)
cytoplasm	Egl nine homolog 1	Homo sapiens (human)
mitochondrion	Carbonic anhydrase 5B, mitochondrial	Homo sapiens (human)
mitochondrial matrix	Carbonic anhydrase 5B, mitochondrial	Homo sapiens (human)
mitochondrion	Carbonic anhydrase 5B, mitochondrial	Homo sapiens (human)
cytoplasm	Carbonic anhydrase 5B, mitochondrial	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Assay ID	Title	Year	Journal	Article
AID1543452	Inhibition of N-terminal His6-tagged recombinant Paramecium bursaria chlorella virus 1 CPH expressed in Escherichia coli Rosetta 2 (DE3) cells pre-incubated for 5 mins before 2OG as substrate and Fe2 as co-factor addition in presence of L-ascorbate and me	2019	Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12	Inhibition of a viral prolyl hydroxylase.
AID1432752	Cytotoxicity against mouse BALB/3T3 cells assessed as reduction in cell proliferation after 72 hrs by SRB assay	2017	Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6	Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
AID1079946	Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079939	Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID344916	Inhibition of 2-oxoglutarate-dependent human JMJD2E in presence of excess 2-oxoglutarate and 10 uM Fe2 by FDH coupled assay	2008	Journal of medicinal chemistry, Nov-27, Volume: 51, Issue:22	Inhibitor scaffolds for 2-oxoglutarate-dependent histone lysine demethylases.
AID721525	Binding affinity to human PHD2 catalytic domain (181 to 426) Mn2 expressed in Escherichia coli by NMR spectroscopic analysis	2013	Journal of medicinal chemistry, Jan-24, Volume: 56, Issue:2	Reporter ligand NMR screening method for 2-oxoglutarate oxygenase inhibitors.
AID594382	Displacement of [3H]nicotinic acid from human GPR109a receptor expressed in human HEK293T cells at 10 uM by liquid scintillation counting	2011	Bioorganic & medicinal chemistry letters, May-01, Volume: 21, Issue:9	Structure-activity relationships of trans-substituted-propenoic acid derivatives on the nicotinic acid receptor HCA2 (GPR109A).
AID1079935	Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1079942	Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079938	Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1432763	Glutathione reactivity in pH 7.4 PBS measured after 6 to 36 hrs in presence of 1.375 mmol GSH by DTNB reagent based spectrophotometric method	2017	Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6	Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
AID456402	Selectivity ratio of Kinact for human recombinant carbonic anhydrase 2 to Kinact for human recombinant carbonic anhydrase 5A	2010	Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1	Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID721529	Displacement of 2OG from catalytic domain of PHD2 (181 to 426) (unknown origin) expressed in Escherichia coli at 400 uM	2013	Journal of medicinal chemistry, Jan-24, Volume: 56, Issue:2	Reporter ligand NMR screening method for 2-oxoglutarate oxygenase inhibitors.
AID1079941	Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID360151	Ratio of pKi for mouse Oat1 expressed in Xenopus oocytes to pKi for mouse Oat6 expressed in Xenopus oocytes	2007	The Journal of biological chemistry, Aug-17, Volume: 282, Issue:33	Structural variation governs substrate specificity for organic anion transporter (OAT) homologs. Potential remote sensing by OAT family members.
AID1432760	Inhibition of Sporosarcina pasteurii CCM 2056 urease assessed as reduction in ammonia production by measuring steady state enzyme-inhibitor complex using urea as substrate measured for 120 mins by phenol-hypochlorite method	2017	Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6	Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
AID1079949	Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID349747	Inhibition of human recombinant PHD2 (181-426) expressed in Escherichia coli BL21 (DE3) by TR-FRET assay	2009	Journal of medicinal chemistry, May-14, Volume: 52, Issue:9	Application of a proteolysis/mass spectrometry method for investigating the effects of inhibitors on hydroxylase structure.
AID456404	Selectivity ratio of Kinact for human recombinant carbonic anhydrase 2 to Kinact for human recombinant carbonic anhydrase 5B	2010	Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1	Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID1079945	Animal toxicity known. [column 'TOXIC' in source]
AID360150	Inhibition of mouse Oat1-mediated [3H]PAH uptake in Xenopus oocytes after 1 hr	2007	The Journal of biological chemistry, Aug-17, Volume: 282, Issue:33	Structural variation governs substrate specificity for organic anion transporter (OAT) homologs. Potential remote sensing by OAT family members.
AID456400	Inhibition of human recombinant carbonic anhydrase 5B by stopped flow CO2 hydration method	2010	Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1	Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID1432759	Inhibition of Sporosarcina pasteurii CCM 2056 urease assessed as reduction in ammonia production by measuring initial state enzyme-inhibitor complex using urea as substrate measured for 120 mins by phenol-hypochlorite method	2017	Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6	Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
AID1432764	Inhibition of Carica papaya papain at 0.1 to 1 mM using BzArgOEt as substrate measured for 30 mins	2017	Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6	Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
AID1079931	Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID429169	Activation of human mitochondrial NADP-ME E59L mutant expressed in Escherichia coli XL-1 by spectrophotometry	2009	Bioorganic & medicinal chemistry, Aug-01, Volume: 17, Issue:15	Effects of structural analogues of the substrate and allosteric regulator of the human mitochondrial NAD(P)+-dependent malic enzyme.
AID344918	Inhibition of 2-oxoglutarate-dependent human JMJD2E preincubated for 30 mins by FDH coupled assay	2008	Journal of medicinal chemistry, Nov-27, Volume: 51, Issue:22	Inhibitor scaffolds for 2-oxoglutarate-dependent histone lysine demethylases.
AID1580649	Anti-immunosuppressive activity in LPS-activated mouse MDSC assessed as reduction in PD-L1 expression at 20 to 40 uM incubated for 24 hrs by flow cytometry	2019	Journal of natural products, 11-22, Volume: 82, Issue:11	Diterpenoids and Bisnorditerpenoids from
AID1432751	Inhibition of Sporosarcina pasteurii CCM 2056 urease assessed as reduction in ammonia production using urea as substrate measured for 120 mins by phenol-hypochlorite method	2017	Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6	Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
AID1517970	Inhibition of human FBPase expressed in Escherichia coli BL21 (DE3) at 500 uM using FBP as substrate incubated for 5 mins by malachite green dye based spectrophotometry relative to control	2019	European journal of medicinal chemistry, Dec-15, Volume: 184	Discovery of novel allosteric site and covalent inhibitors of FBPase with potent hypoglycemic effects.
AID1079934	Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079948	Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079933	Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID349748	Destabilizing effect on human recombinant PHD2 (181-426) expressed in Escherichia coli BL21 (DE3) assessed as half life by limited trypsinolysis/MALDI-MS analysis in presence of ferrous ion	2009	Journal of medicinal chemistry, May-14, Volume: 52, Issue:9	Application of a proteolysis/mass spectrometry method for investigating the effects of inhibitors on hydroxylase structure.
AID1079944	Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID734755	Inhibition of human hexahistidine-tagged full-length FTO expressed in Escherichia coli BL21 (DE3) using 3-methylthymidine as substrate assessed as inhibition of 3-methylthymidine conversion to thymidine after 1 hr by liquid chromatographic analysis	2013	Journal of medicinal chemistry, May-09, Volume: 56, Issue:9	Structural basis for inhibition of the fat mass and obesity associated protein (FTO).
AID1079943	Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID721523	Inhibition of human PHD2 catalytic domain (181 to 426) Mn2 expressed in Escherichia coli by NMR spectroscopic analysis	2013	Journal of medicinal chemistry, Jan-24, Volume: 56, Issue:2	Reporter ligand NMR screening method for 2-oxoglutarate oxygenase inhibitors.
AID1432754	Time-dependent Sporosarcina pasteurii CCM 2056 urease assessed as reduction in ammonia production using urea as substrate by phenol-hypochlorite method	2017	Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6	Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
AID456397	Inhibition of human recombinant carbonic anhydrase 2 by stopped flow CO2 hydration method	2010	Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1	Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID1079937	Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID456398	Inhibition of human recombinant carbonic anhydrase 1 by stopped flow CO2 hydration method	2010	Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1	Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID1079947	Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID344917	Inhibition of 2-oxoglutarate-dependent human JMJD2E in presence of excess H3K9me3 peptide and 10 uM Fe2 by FDH coupled assay	2008	Journal of medicinal chemistry, Nov-27, Volume: 51, Issue:22	Inhibitor scaffolds for 2-oxoglutarate-dependent histone lysine demethylases.
AID1079936	Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID1079940	Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1432758	Inhibition of Proteus mirabilis 543 urease at pH 5.5 assessed as reduction in ammonia production using urea as substrate preincubated for 120 mins followed by substrate addition measured after 15 mins by NaOH-hypochlorite method	2017	Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6	Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
AID1432766	Inhibition of Proteus mirabilis 543 urease at pH 5.5 assessed as reduction in ammonia production using urea as substrate followed by substrate addition by NaOH-hypochlorite method	2017	Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6	Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
AID344926	Inhibition of 2-oxoglutarate-dependent human recombinant HIF PHD2 preincubated for 1 hr	2008	Journal of medicinal chemistry, Nov-27, Volume: 51, Issue:22	Inhibitor scaffolds for 2-oxoglutarate-dependent histone lysine demethylases.
AID360149	Inhibition of mouse Oat6-mediated [3H]ES uptake in Xenopus oocytes after 1 hr	2007	The Journal of biological chemistry, Aug-17, Volume: 282, Issue:33	Structural variation governs substrate specificity for organic anion transporter (OAT) homologs. Potential remote sensing by OAT family members.
AID456403	Selectivity ratio of Kinact for human recombinant carbonic anhydrase 1 to Kinact for human recombinant carbonic anhydrase 5B	2010	Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1	Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID456399	Inhibition of human recombinant carbonic anhydrase 5A by stopped flow CO2 hydration method	2010	Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1	Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID1432757	Inhibition of Proteus mirabilis 543 urease at pH 5.5 assessed as reduction in ammonia production using urea as substrate measured after 15 mins by NaOH-hypochlorite method	2017	Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6	Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
AID1079932	Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1432756	Reversible inhibition of Sporosarcina pasteurii CCM 2056 urease assessed as reduction in ammonia production by measuring recovery of enzyme activity at 10 times IC50 preincubated for 60 mins followed by 100-fold dilution in to PBS containing urea as subst	2017	Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6	Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
AID1432755	Competitive inhibition of Sporosarcina pasteurii CCM 2056 urease assessed as reduction in ammonia production preincubated with enzyme followed by addition of varying levels of urea as substrate measured for 120 mins by Lineweaver-Burk plot analysis	2017	Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6	Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
AID429168	Activation of human recombinant wild type mitochondrial NADP-ME expressed in Escherichia coli BL21 assessed as one-half maximal activation by spectrophotometry	2009	Bioorganic & medicinal chemistry, Aug-01, Volume: 17, Issue:15	Effects of structural analogues of the substrate and allosteric regulator of the human mitochondrial NAD(P)+-dependent malic enzyme.
AID1763191	Inhibition of TET (unknown origin)	2021	Bioorganic & medicinal chemistry, 06-01, Volume: 39	SAR insights into TET2 catalytic domain inhibition: Synthesis of 2-Hydroxy-4-Methylene-pentanedicarboxylates.
AID456401	Selectivity ratio of Kinact for human recombinant carbonic anhydrase 1 to Kinact for human recombinant carbonic anhydrase 5A	2010	Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1	Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID1745845	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.
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
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.
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.
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.
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.
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.
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.
AID1799787	Isothermal Titration Calorimetry from Article 10.1074/jbc.M110.110403: \\Identification of a chemoreceptor for tricarboxylic acid cycle intermediates: differential chemotactic response towards receptor ligands.\\	2010	The Journal of biological chemistry, Jul-23, Volume: 285, Issue:30	Identification of a chemoreceptor for tricarboxylic acid cycle intermediates: differential chemotactic response towards receptor ligands.
AID1798635	FDH Coupled Inhibition Assay from Article 10.1021/jm800936s: \\Inhibitor Scaffolds for 2-Oxoglutarate-Dependent Histone Lysine Demethylases.\\	2008	Journal of medicinal chemistry, Nov-27, Volume: 51, Issue:22	Inhibitor scaffolds for 2-oxoglutarate-dependent histone lysine demethylases.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	99 (12.72)	18.7374
1990's	163 (20.95)	18.2507
2000's	224 (28.79)	29.6817
2010's	241 (30.98)	24.3611
2020's	51 (6.56)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	26 (3.21%)	5.53%
Reviews	50 (6.17%)	6.00%
Case Studies	25 (3.09%)	4.05%
Observational	1 (0.12%)	0.25%
Other	708 (87.41%)	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
alpha-hydroxyglutarate 2-hydroxyglutarate : A dicarboxylic acid anion obtained by deprotonation of at least one of the carboxy groups of 2-hydroxyglutaric acid.. 2-hydroxyglutaric acid : A 2-hydroxydicarboxylic acid that is glutaric acid in which one hydrogen alpha- to a carboxylic acid group is substituted by a hydroxy group.	2.49	2	0	2-hydroxydicarboxylic acid; dicarboxylic fatty acid	metabolite; mouse metabolite
2-oxo-3-methylvalerate alpha-keto-beta-methylvaleric acid: RN given refers to parent cpd. 3-methyl-2-oxovaleric acid : A 2-oxo monocarboxylic acid that is valeric acid carrying oxo- and methyl substituents at C-2 and C-3, respectively. An alpha-keto acid analogue and metabolite of isoleucine in man, animals and bacteria. Used as a clinical marker for maple syrup urine disease (MSUD).	1.97	1	0	2-oxo monocarboxylic acid; branched-chain keto acid	human metabolite
alpha-ketoglutaric acid 2-oxoglutaric acid : An oxo dicarboxylic acid that consists of glutaric acid bearing an oxo substituent at position 2. It is an intermediate metabolite in Krebs cycle.	2.47	2	0	oxo dicarboxylic acid	fundamental metabolite
2-keto-4-methylvalerate alpha-ketoisocaproic acid: RN given refers to parent cpd. 4-methyl-2-oxopentanoate : A 2-oxo monocarboxylic acid anion that is the conjugate base of 4-methyl-2-oxopentanoic acid.. 4-methyl-2-oxopentanoic acid : A 2-oxo monocarboxylic acid that is pentanoic acid (valeric acid) substituted with a keto group at C-2 and a methyl group at C-4. A metabolite that has been found to accumulate in maple syrup urine disease.	2	1	0	2-oxo monocarboxylic acid; branched-chain keto acid	algal metabolite; human metabolite
protocatechuic acid protocatechuic acid: RN given refers to parent cpd; structure. 3,4-dihydroxybenzoic acid : A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.	2.08	1	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.	2.46	2	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
4-hydroxyphenylacetic acid 4-hydroxyphenylacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group.	2.05	1	0	monocarboxylic acid; phenols	fungal metabolite; human metabolite; mouse metabolite; plant metabolite
4-hydroxybenzoic acid 4-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring.	2.13	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.	4.07	14	0	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	2.04	1	0	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
adenine [no description available]	7.13	1	0	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
adipic acid adipic acid : An alpha,omega-dicarboxylic acid that is the 1,4-dicarboxy derivative of butane.	2.98	4	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	food acidity regulator; human xenobiotic metabolite
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	3.38	7	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
anthranilic acid anthranilic acid: RN given refers to parent cpd; structure in Negwer, 5th ed, #565. anthranilic acid : An aminobenzoic acid that is benzoic acid having a single amino substituent located at position 2. It is a metabolite produced in L-tryptophan-kynurenine pathway in the central nervous system.	2.02	1	0	aminobenzoic acid	human metabolite; mouse metabolite
arsenic acid arsenic acid: RN given refers to orthoarsenic acid(H3AsO4); see also sodium arsenate. arsenic acid : An arsenic oxoacid comprising one oxo group and three hydroxy groups attached to a central arsenic atom.	2	1	0	arsenic oxoacid	Escherichia coli metabolite
quinacrine Quinacrine: An acridine derivative formerly widely used as an antimalarial but superseded by chloroquine in recent years. It has also been used as an anthelmintic and in the treatment of giardiasis and malignant effusions. It is used in cell biological experiments as an inhibitor of phospholipase A2.. quinacrine : A member of the class of acridines that is acridine substituted by a chloro group at position 6, a methoxy group at position 2 and a [5-(diethylamino)pentan-2-yl]nitrilo group at position 9.	1.97	1	0	acridines; aromatic ether; organochlorine compound; tertiary amino compound	antimalarial; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor
beta-alanine [no description available]	2.72	2	0	amino acid zwitterion; beta-amino acid	agonist; fundamental metabolite; human metabolite; inhibitor; neurotransmitter
benzene [no description available]	3.53	2	0	aromatic annulene; benzenes; volatile organic compound	carcinogenic agent; environmental contaminant; non-polar solvent
benzoic acid Benzoic Acid: A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid.. benzoic acid : A compound comprising a benzene ring core carrying a carboxylic acid substituent.. aromatic carboxylic acid : Any carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.	3.1	5	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
betaine glycine betaine : The amino acid betaine derived from glycine.	2.8	3	0	amino-acid betaine; glycine derivative	fundamental metabolite
bromide Bromides: Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	2.02	1	0	halide anion; monoatomic bromine
2,3-butylene glycol 2,3-butylene glycol: RN given refers to cpd without isomeric designation. butane-2,3-diol : A butanediol in which hydroxylation is at C-2 and C-3.	2.08	1	0	butanediol; glycol; secondary alcohol
butyric acid Butyric Acid: A four carbon acid, CH3CH2CH2COOH, with an unpleasant odor that occurs in butter and animal fat as the glycerol ester.. butyrate : A short-chain fatty acid anion that is the conjugate base of butyric acid, obtained by deprotonation of the carboxy group.. butyric acid : A straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group.	2.96	4	0	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
carbamates [no description available]	2.37	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.	2.61	2	0	carbon oxide; gas molecular entity; one-carbon compound	biomarker; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; human metabolite; ligand; metabolite; mitochondrial respiratory-chain inhibitor; mouse metabolite; neurotoxin; neurotransmitter; P450 inhibitor; probe; signalling molecule; vasodilator agent
formic acid formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.	5.18	15	0	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
carnitine [no description available]	3.78	2	1	amino-acid betaine	human metabolite; mouse metabolite
catechol [no description available]	2.43	2	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).	5.92	13	2	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
choline [no description available]	2.1	1	0	cholines	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter; nutrient; plant metabolite; Saccharomyces cerevisiae metabolite
aconitic acid Aconitic Acid: A tricarboxylic acid with the formula (COOH)-CH2-C(COOH)=CH-COOH.. aconitic acid : A tricarboxylic acid that is prop-1-ene substituted by carboxy groups at positions 1, 2 and 3.	2.92	4	0	tricarboxylic acid
citric acid, anhydrous Citric Acid: A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability.. citric acid : A tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms.	6.94	54	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.	1.98	1	0	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
hydrochloric acid Hydrochloric Acid: A strong corrosive acid that is commonly used as a laboratory reagent. It is formed by dissolving hydrogen chloride in water. GASTRIC ACID is the hydrochloric acid component of GASTRIC JUICE.. hydrogen chloride : A mononuclear parent hydride consisting of covalently bonded hydrogen and chlorine atoms.	2.51	2	0	chlorine molecular entity; gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse 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).	2.43	2	0	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
phloroglucinol Phloroglucinol: A trinitrobenzene derivative with antispasmodic properties that is used primarily as a laboratory reagent.. phloroglucinol : A benzenetriol with hydroxy groups at position 1, 3 and 5.	2.06	1	0	benzenetriol; phenolic donor	algal metabolite
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	4.04	4	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
2-butynedioic acid 2-butynedioic acid: RN given refers to parent cpd. butynedioic acid : An acetylenic compound that is acetylene in which the hydrogens are replaced by carboxy groups.	2.15	1	0	acetylenic compound; C4-dicarboxylic acid
nornicotine nornicotine: agricultural or horticultural insecticide; RN given refers to (+-)-isomer; structure	1.96	1	0
3-hydroxybutyric acid 3-Hydroxybutyric Acid: BUTYRIC ACID substituted in the beta or 3 position. It is one of the ketone bodies produced in the liver.. 3-hydroxybutyric acid : A straight-chain 3-hydroxy monocarboxylic acid comprising a butyric acid core with a single hydroxy substituent in the 3- position; a ketone body whose levels are raised during ketosis, used as an energy source by the brain during fasting in humans. Also used to synthesise biodegradable plastics.	2.96	4	0	(omega-1)-hydroxy fatty acid; 3-hydroxy monocarboxylic acid; hydroxybutyric acid	human metabolite
hippuric acid hippuric acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #4591. N-benzoylglycine : An N-acylglycine in which the acyl group is specified as benzoyl.	2.03	1	0	N-acylglycine	human blood serum metabolite; uremic toxin
methylmalonic acid Methylmalonic Acid: A malonic acid derivative which is a vital intermediate in the metabolism of fat and protein. Abnormalities in methylmalonic acid metabolism lead to methylmalonic aciduria. This metabolic disease is attributed to a block in the enzymatic conversion of methylmalonyl CoA to succinyl CoA.. methylmalonic acid : A dicarboxylic acid that is malonic acid in which one of the methylene hydrogens is substituted by a methyl group.	2.69	3	0	C4-dicarboxylic acid	human 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.	8.2	107	0	2-hydroxydicarboxylic acid; C4-dicarboxylic acid	food acidity regulator; fundamental metabolite
creatine [no description available]	2.01	1	0	glycine derivative; guanidines; zwitterion	geroprotector; human metabolite; mouse metabolite; neuroprotective agent; nutraceutical
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	13.13	44	1	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
5,6-dihydroorotate 4,5-dihydroorotic acid: RN given refers to cpd without isomeric designation; structure. dihydroorotic acid : A pyrimidinemonocarboxylic acid that results from the base-catalysed cyclisation of N(alpha)-carbethoxyasparagine.	4.37	6	0	monocarboxylic acid; N-acylurea; pyrimidinemonocarboxylic acid; secondary amide
dihydroxyacetone phosphate Dihydroxyacetone Phosphate: An important intermediate in lipid biosynthesis and in glycolysis.. dihydroxyacetone phosphate : A member of the class of glycerone phosphates that consists of glycerone bearing a single phospho substituent.	2.05	1	0	glycerone phosphates; primary alpha-hydroxy ketone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	3.11	5	0	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
3-phosphoglycerate 3-phosphoglycerate : An organic anion obtained by deprotonation of at least one of the acidic groups of 3-phosphoglyceric acid.	2.42	2	0	monophosphoglyceric acid; tetronic acid derivative	algal metabolite; fundamental metabolite
glutaric acid glutaric acid: RN given refers to parent cpd. glutaric acid : An alpha,omega-dicarboxylic acid that is a linear five-carbon dicarboxylic acid.	3.54	8	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	Daphnia magna metabolite; human metabolite
glycine [no description available]	4.65	6	1	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	3.9	12	0	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
alpha-glycerophosphoric acid [no description available]	2.39	2	0	glycerol monophosphate	algal metabolite; human metabolite
glycolic acid glycolic acid: RN given refers to parent cpd. glycolic acid : A 2-hydroxy monocarboxylic acid that is acetic acid where the methyl group has been hydroxylated.	2.41	2	0	2-hydroxy monocarboxylic acid; primary alcohol	keratolytic drug; metabolite
hydrogen carbonate Bicarbonates: Inorganic salts that contain the -HCO3 radical. They are an important factor in determining the pH of the blood and the concentration of bicarbonate ions is regulated by the kidney. Levels in the blood are an index of the alkali reserve or buffering capacity.. hydrogencarbonate : The carbon oxoanion resulting from the removal of a proton from carbonic acid.	3.77	2	1	carbon oxoanion	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
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.	3.86	12	0	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
hydroxylamine amino alcohol : An alcohol containing an amino functional group in addition to the alcohol-defining hydroxy group.	7.36	2	0	hydroxylamines	algal metabolite; bacterial xenobiotic metabolite; EC 1.1.3.13 (alcohol oxidase) inhibitor; EC 4.2.1.22 (cystathionine beta-synthase) inhibitor; EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor; nitric oxide donor; nucleophilic reagent
indole [no description available]	1.99	1	0	indole; polycyclic heteroarene	Escherichia coli metabolite
indoleacetic acid indoleacetic acid: RN given refers to unlabeled parent cpd; structure in Merck Index, 9th ed, #4841. auxin : Any of a group of compounds, both naturally occurring and synthetic, that induce cell elongation in plant stems (from Greek alphaupsilonxialphanuomega, "to grow").. indole-3-acetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.	2.05	1	0	indole-3-acetic acids; monocarboxylic acid	auxin; human metabolite; mouse metabolite; plant hormone; plant metabolite
itaconic acid itaconic acid : A dicarboxylic acid that is methacrylic acid in which one of the methyl hydrogens is substituted by a carboxylic acid group.	5.24	6	0	dicarboxylic acid; dicarboxylic fatty acid; olefinic compound	fungal metabolite; human metabolite
aspartic semialdehyde aspartic semialdehyde: RN given refers to cpd without isomeric designation	1.99	1	0
malonic acid malonic acid : An alpha,omega-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group.. dicarboxylic acid : Any carboxylic acid containing two carboxy groups.	3.89	12	0	alpha,omega-dicarboxylic acid	human metabolite
pyruvaldehyde Pyruvaldehyde: An organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.. methylglyoxal : A 2-oxo aldehyde derived from propanal.	2.21	1	0	2-oxo aldehyde; propanals	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	2.95	4	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
phytic acid Phytic Acid: Complexing agent for removal of traces of heavy metal ions. It acts also as a hypocalcemic agent.. myo-inositol hexakisphosphate : A myo-inositol hexakisphosphate in which each hydroxy group of myo-inositol is monophosphorylated.	2.44	2	0	inositol phosphate
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.	1.96	1	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.	2.25	1	0	pyridine alkaloid; pyridinecarboxamide; vitamin B3	anti-inflammatory agent; antioxidant; cofactor; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; Escherichia coli metabolite; geroprotector; human urinary metabolite; metabolite; mouse metabolite; neuroprotective agent; Saccharomyces cerevisiae metabolite; Sir2 inhibitor
niacin Niacin: A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has PELLAGRA-curative, vasodilating, and antilipemic properties.. vitamin B3 : Any member of a group of vitamers that belong to the chemical structural class called pyridines that exhibit biological activity against vitamin B3 deficiency. Vitamin B3 deficiency causes a condition known as pellagra whose symptoms include depression, dermatitis and diarrhea. The vitamers include nicotinic acid and nicotinamide (and their ionized and salt forms).. nicotinic acid : A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group.	1.96	1	0	pyridine alkaloid; pyridinemonocarboxylic acid; vitamin B3	antidote; antilipemic drug; EC 3.5.1.19 (nicotinamidase) inhibitor; Escherichia coli metabolite; human urinary metabolite; metabolite; mouse metabolite; plant metabolite; vasodilator agent
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	4.4	21	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
nitric acid Nitric Acid: Nitric acid (HNO3). A colorless liquid that is used in the manufacture of inorganic and organic nitrates and nitro compounds for fertilizers, dye intermediates, explosives, and many different organic chemicals. Continued exposure to vapor may cause chronic bronchitis; chemical pneumonitis may occur. (From Merck Index, 11th ed). nitric acid : A nitrogen oxoacid of formula HNO3 in which the nitrogen atom is bonded to a hydroxy group and by equivalent bonds to the remaining two oxygen atoms.	2	1	0	nitrogen oxoacid	protic solvent; reagent
nitrites Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)	2.4	2	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human 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.	11.02	8	1	pyrimidinemonocarboxylic acid	Escherichia coli metabolite; metabolite; mouse metabolite
oxaloacetic acid Oxaloacetic Acid: A dicarboxylic acid ketone that is an important metabolic intermediate of the CITRIC ACID CYCLE. It can be converted to ASPARTIC ACID by ASPARTATE TRANSAMINASE.. oxaloacetic acid : An oxodicarboxylic acid that is succinic acid bearing a single oxo group.	3.15	5	0	C4-dicarboxylic acid; oxo dicarboxylic acid	geroprotector; metabolite
oxalic acid Oxalic Acid: A strong dicarboxylic acid occurring in many plants and vegetables. It is produced in the body by metabolism of glyoxylic acid or ascorbic acid. It is not metabolized but excreted in the urine. It is used as an analytical reagent and general reducing agent.. oxalic acid : An alpha,omega-dicarboxylic acid that is ethane substituted by carboxyl groups at positions 1 and 2.	5.37	18	0	alpha,omega-dicarboxylic acid	algal metabolite; human metabolite; plant metabolite
4-hydroxyphenylpyruvic acid 4-hydroxyphenylpyruvic acid: RN given refers to parent cpd. 4-hydroxyphenylpyruvic acid : A 2-oxo monocarboxylic acid that is pyruvic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group.	2.03	1	0	2-oxo monocarboxylic acid; phenols	human metabolite
pentachlorophenol PENTA: structure given in first source	2	1	0	aromatic fungicide; chlorophenol; organochlorine pesticide; pentachlorobenzenes	human xenobiotic metabolite
phenol [no description available]	2.13	1	0	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
phenylpyruvic acid phenylpyruvic acid: RN given refers to parent cpd. phenylpyruvate : A 2-oxo monocarboxylic acid anion resulting from deprotonation of the carboxy group of either keto- or enol-phenylpyruvic acid.. keto-phenylpyruvic acid : A 2-oxo monocarboxylic acid that is 3-phenylpropanoic acid substituted by an oxo group at position 2. It is an intermediate metabolite in the phenylalanine pathway.	2.03	1	0	2-oxo monocarboxylic acid	chromogenic compound; EC 6.4.1.1 (pyruvate carboxylase) inhibitor; fundamental metabolite
phosphoric acid phosphoric acid: concise etchant is 37% H3PO4. phosphoric acid : A phosphorus oxoacid that consists of one oxo and three hydroxy groups joined covalently to a central phosphorus atom.	2.41	2	0	phosphoric acids	algal metabolite; fertilizer; human metabolite; NMR chemical shift reference compound; solvent
phosphoenolpyruvate Phosphoenolpyruvate: A monocarboxylic acid anion derived from selective deprotonation of the carboxy group of phosphoenolpyruvic acid. It is a metabolic intermediate in GLYCOLYSIS; GLUCONEOGENESIS; and other pathways.. phosphoenolpyruvate : A monocarboxylic acid anion resuting from selective deprotonation of the carboxy group of phosphoenolpyruvic acid.. phosphoenolpyruvic acid : A monocarboxylic acid that is acrylic acid substituted by a phosphonooxy group at position 2. It is a metabolic intermediate in pathways like glycolysis and gluconeogenesis.	2.42	2	0	carboxyalkyl phosphate; monocarboxylic acid	fundamental 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.	2.05	1	0	benzenedicarboxylic acid	human xenobiotic metabolite
propylene glycol Propylene Glycol: A clear, colorless, viscous organic solvent and diluent used in pharmaceutical preparations.. propane-1,2-diol : The simplest member of the class of propane-1,2-diols, consisting of propane in which a hydrogen at position 1 and a hydrogen at position 2 are substituted by hydroxy groups. A colourless, viscous, hygroscopic, low-melting (-59degreeC) and high-boiling (188degreeC) liquid with low toxicity, it is used as a solvent, emulsifying agent, and antifreeze.	1.99	1	0	glycol; propane-1,2-diols	allergen; human xenobiotic metabolite; mouse metabolite; protic solvent
propionic acid propionic acid : A short-chain saturated fatty acid comprising ethane attached to the carbon of a carboxy group.	4.62	8	0	saturated fatty acid; short-chain fatty acid	antifungal drug
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.	4.64	27	0	2-oxo monocarboxylic acid	cofactor; fundamental metabolite
quinolinic acid Quinolinic Acid: A metabolite of tryptophan with a possible role in neurodegenerative disorders. Elevated CSF levels of quinolinic acid are correlated with the severity of neuropsychological deficits in patients who have AIDS.. pyridinedicarboxylic acid : Any member of the class of pyridines carrying two carboxy groups.. quinolinic acid : A pyridinedicarboxylic acid that is pyridine substituted by carboxy groups at positions 2 and 3. It is a metabolite of tryptophan.	2.04	1	0	pyridinedicarboxylic acid	Escherichia coli metabolite; human metabolite; mouse metabolite; NMDA receptor agonist
thiosulfates Thiosulfates: Inorganic salts of thiosulfuric acid possessing the general formula R2S2O3.. thiosulfate(2-) : A divalent inorganic anion obtained by removal of both protons from thiosulfuric acid.	2.7	3	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion	human metabolite
dithionite Dithionite: Dithionite. The dithionous acid ion and its salts.	2	1	0	sulfur oxide; sulfur oxoanion
sarcosine cocobetaine: N-alkyl-betaine; cause of shampoo dermatitis	2.07	1	0	N-alkylglycine zwitterion; N-alkylglycine; N-methyl-amino acid; N-methylglycines	Escherichia coli metabolite; glycine receptor agonist; glycine transporter 1 inhibitor; human metabolite; mouse metabolite
selenic acid Selenic Acid: A strong dibasic acid with the molecular formula H2SeO4. Included under this heading is the acid form, and inorganic salts of dihydrogen selenium tetraoxide.	2	1	0	selenium oxoacid
sulfites Sulfites: Inorganic salts of sulfurous acid.. sulfites : Any sulfurous acid derivative that is a salt or an ester of sulfurous acid.. organosulfonate oxoanion : An organic anion obtained by deprotonation of the sufonate group(s) of any organosulfonic acid.. sulfite : A sulfur oxoanion that is the conjugate base of hydrogen sulfite (H2SO3).	2.05	1	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion
succinic acid Succinic Acid: A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawley's Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851). succinic acid : An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.	10.61	129	1	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
sulfuric acid sulfuric acid : A sulfur oxoacid that consists of two oxo and two hydroxy groups joined covalently to a central sulfur atom.	2.06	1	0	sulfur oxoacid	catalyst
taurine [no description available]	2.1	1	0	amino sulfonic acid; zwitterion	antioxidant; Escherichia coli metabolite; glycine receptor agonist; human metabolite; mouse metabolite; nutrient; radical scavenger; Saccharomyces cerevisiae metabolite
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	4.81	10	0	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
trimethyloxamine trimethyloxamine: used in manufacture of quaternary ammonium cpds; insect attractant; warming agent for gas; oxidant; structure. trimethylamine N-oxide : A tertiary amine oxide resulting from the oxidation of the amino group of trimethylamine.	3.24	6	0	tertiary amine oxide	Escherichia coli metabolite; metabolite; osmolyte
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	2.02	1	0	pyrimidine nucleobase; pyrimidone	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; prodrug; Saccharomyces cerevisiae metabolite
uric acid Uric Acid: An oxidation product, via XANTHINE OXIDASE, of oxypurines such as XANTHINE and HYPOXANTHINE. It is the final oxidation product of purine catabolism in humans and primates, whereas in most other mammals URATE OXIDASE further oxidizes it to ALLANTOIN.. uric acid : An oxopurine that is the final oxidation product of purine metabolism.. 6-hydroxy-1H-purine-2,8(7H,9H)-dione : A tautomer of uric acid having oxo groups at C-2 and C-8 and a hydroxy group at C-6.. 7,9-dihydro-1H-purine-2,6,8(3H)-trione : An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8.	1.99	1	0	uric acid	Escherichia coli metabolite; human metabolite; mouse metabolite
urea pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.	3.51	8	0	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
isocitric acid isocitric acid: RN given refers to unlabeled parent cpd. isocitric acid : A tricarboxylic acid that is propan-1-ol with a hydrogen at each of the 3 carbon positions replaced by a carboxy group.	3.31	6	0	secondary alcohol; tricarboxylic acid	fundamental metabolite
mandelic acid SAMMA: mandelic acid condensation polymer	2.15	1	0	2-hydroxy monocarboxylic acid; benzenes	antibacterial agent; human xenobiotic metabolite
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'.	1.98	1	0	bipyridine	chelator; ferroptosis inhibitor
2-(n-heptyl)-4-hydroxyquinoline n-oxide 2-(n-heptyl)-4-hydroxyquinoline N-oxide: structure. 2-heptyl-4-hydroxyquinoline N-oxide : An inhibitor of the mitochondrial respiratory chain at cytochrome bc1 and of photosynthetic electron flow immediately before cytochrome b559.	2.39	2	0	monohydroxyquinoline
mercaptoethanol Mercaptoethanol: A water-soluble thiol derived from hydrogen sulfide and ethanol. It is used as a reducing agent for disulfide bonds and to protect sulfhydryl groups from oxidation.	1.97	1	0	alkanethiol; primary alcohol	geroprotector
meglutol Meglutol: An antilipemic agent which lowers cholesterol, triglycerides, serum beta-lipoproteins and phospholipids. It acts by interfering with the enzymatic steps involved in the conversion of acetate to hydroxymethylglutaryl coenzyme A as well as inhibiting the activity of HYDROXYMETHYLGLUTARYL COA REDUCTASES which is the rate limiting enzyme in the biosynthesis of cholesterol.. 3-hydroxy-3-methylglutaric acid : A dicarboxylic acid that is glutaric acid in which one of the two hydrogens at position 3 is substituted by a hydroxy group, while the other is substituted by a methyl group. It has been found to accumulate in urine of patients suffering from HMG-CoA lyase (3-hydroxy-3-methylglutaryl-CoA lyase, EC 4.1.3.4) deficiency. It occurs as a plant metabolite in Crotalaria dura.	2	1	0	3-hydroxy carboxylic acid; dicarboxylic acid; tertiary alcohol	anticholesteremic drug; antimetabolite; EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor; human metabolite; plant metabolite
3-nitropropionic acid 3-nitropropionic acid: succinate dehydrogenase inactivator; biosynthesized by FABACEAE plants from ASPARAGINE. 3-nitropropanoic acid : A C-nitro compound that is propanoic acid in which one of the methyl hydrogens has been replaced by a nitro group.	2.02	1	0	C-nitro compound	antimycobacterial drug; EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor; mycotoxin; neurotoxin
oxyquinoline Oxyquinoline: An antiseptic with mild fungistatic, bacteriostatic, anthelmintic, and amebicidal action. It is also used as a reagent and metal chelator, as a carrier for radio-indium for diagnostic purposes, and its halogenated derivatives are used in addition as topical anti-infective agents and oral antiamebics.. quinolin-8-ol : A monohydroxyquinoline that is quinoline substituted by a hydroxy group at position 8. Its fungicidal properties are used for the control of grey mould on vines and tomatoes.	2.05	1	0	monohydroxyquinoline	antibacterial agent; antifungal agrochemical; antiseptic drug; iron chelator
acetaminophen Acetaminophen: Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage.. paracetamol : A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.	2.02	1	0	acetamides; phenols	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; cyclooxygenase 3 inhibitor; environmental contaminant; ferroptosis inducer; geroprotector; hepatotoxic agent; human blood serum metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
acetazolamide Acetazolamide: One of the CARBONIC ANHYDRASE INHIBITORS that is sometimes effective against absence seizures. It is sometimes useful also as an adjunct in the treatment of tonic-clonic, myoclonic, and atonic seizures, particularly in women whose seizures occur or are exacerbated at specific times in the menstrual cycle. However, its usefulness is transient often because of rapid development of tolerance. Its antiepileptic effect may be due to its inhibitory effect on brain carbonic anhydrase, which leads to an increased transneuronal chloride gradient, increased chloride current, and increased inhibition. (From Smith and Reynard, Textbook of Pharmacology, 1991, p337)	2.05	1	0	monocarboxylic acid amide; sulfonamide; thiadiazoles	anticonvulsant; diuretic; EC 4.2.1.1 (carbonic anhydrase) inhibitor
acetohydroxamic acid acetohydroxamic acid: urease inhibitor. oxime : Compounds of structure R2C=NOH derived from condensation of aldehydes or ketones with hydroxylamine. Oximes from aldehydes may be called aldoximes; those from ketones may be called ketoximes.. N-hydroxyacetimidic acid : A carbohydroximic acid consisting of acetimidic acid having a hydroxy group attached to the imide nitrogen.. acetohydroxamic acid : A member of the class of acetohydroxamic acids that is acetamide in which one of the amino hydrogens has been replaced by a hydroxy group.	2.15	1	0	acetohydroxamic acids; carbohydroximic acid	algal metabolite; EC 3.5.1.5 (urease) inhibitor
p-aminohippuric acid p-Aminohippuric Acid: The glycine amide of 4-aminobenzoic acid. Its sodium salt is used as a diagnostic aid to measure effective renal plasma flow (ERPF) and excretory capacity.. p-aminohippurate : A hippurate that is the conjugate base of p-aminohippuric acid, arising from deprotonation of the carboxy group.. p-aminohippuric acid : An N-acylglycine that is the 4-amino derivative of hippuric acid; used as a diagnostic agent in the measurement of renal plasma flow.	2.7	3	0	N-acylglycine	Daphnia magna metabolite
2-aminothiazole 2-aminothiazole: RN given refers to parent cpd; structure. 1,3-thiazol-2-amine : A primary amino compound that is 1,3-thiazole substituted by an amino group at position 2.	2.05	1	0	1,3-thiazoles; primary amino compound
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.	2.76	3	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
azathioprine Azathioprine: An immunosuppressive agent used in combination with cyclophosphamide and hydroxychloroquine in the treatment of rheumatoid arthritis. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance has been listed as a known carcinogen. (Merck Index, 11th ed). azathioprine : A thiopurine that is 6-mercaptopurine in which the mercapto hydrogen is replaced by a 1-methyl-4-nitroimidazol-5-yl group. It is a prodrug for mercaptopurine and is used as an immunosuppressant, prescribed for the treatment of inflammatory conditions and after organ transplantation and also for treatment of Crohn's didease and MS.	3.1	1	0	aryl sulfide; C-nitro compound; imidazoles; thiopurine	antimetabolite; antineoplastic agent; carcinogenic agent; DNA synthesis inhibitor; hepatotoxic agent; immunosuppressive agent; prodrug
benzyl isothiocyanate benzyl isothiocyanate: inhibits carcinogen-induced neoplasia; structure in Negwer, 5th ed, #715; also promotes urinary bladder carcinoma	2.21	1	0	benzenes; isothiocyanate	antibacterial drug
bisoprolol Bisoprolol: A cardioselective beta-1 adrenergic blocker. It is effective in the management of HYPERTENSION and ANGINA PECTORIS.	1.96	1	0	secondary alcohol; secondary amine	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; sympatholytic agent
bupranolol Bupranolol: An adrenergic-beta-2 antagonist that has been used for cardiac arrhythmia, angina pectoris, hypertension, glaucoma, and as an antithrombotic.	1.96	1	0	aromatic ether
verapamil Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.	2.43	2	0	aromatic ether; nitrile; polyether; tertiary amino compound
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.	7.25	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
carvedilol [no description available]	2.15	1	0	carbazoles; secondary alcohol; secondary amino compound	alpha-adrenergic antagonist; antihypertensive agent; beta-adrenergic antagonist; cardiovascular drug; vasodilator agent
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.	2.02	1	0	quaternary ammonium ion
ciprofloxacin Ciprofloxacin: A broad-spectrum antimicrobial carboxyfluoroquinoline.. ciprofloxacin : A quinolone that is quinolin-4(1H)-one bearing cyclopropyl, carboxylic acid, fluoro and piperazin-1-yl substituents at positions 1, 3, 6 and 7, respectively.	2.13	1	0	aminoquinoline; cyclopropanes; fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone; zwitterion	antibacterial drug; antiinfective agent; antimicrobial agent; DNA synthesis inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; environmental contaminant; topoisomerase IV inhibitor; xenobiotic
diethyl pyrocarbonate Diethyl Pyrocarbonate: Preservative for wines, soft drinks, and fruit juices and a gentle esterifying agent.. diethyl pyrocarbonate : The diethyl ester of dicarbonic acid.	1.98	1	0	acyclic carboxylic anhydride
dipyridamole Dipyridamole: A phosphodiesterase inhibitor that blocks uptake and metabolism of adenosine by erythrocytes and vascular endothelial cells. Dipyridamole also potentiates the antiaggregating action of prostacyclin. (From AMA Drug Evaluations Annual, 1994, p752). dipyridamole : A pyrimidopyrimidine that is 2,2',2'',2'''-(pyrimido[5,4-d]pyrimidine-2,6-diyldinitrilo)tetraethanol substituted by piperidin-1-yl groups at positions 4 and 8 respectively. A vasodilator agent, it inhibits the formation of blood clots.	2.74	3	0	piperidines; pyrimidopyrimidine; tertiary amino compound; tetrol	adenosine phosphodiesterase inhibitor; EC 3.5.4.4 (adenosine deaminase) inhibitor; platelet aggregation inhibitor; vasodilator agent
ethacrynic acid Ethacrynic Acid: A compound that inhibits symport of sodium, potassium, and chloride primarily in the ascending limb of Henle, but also in the proximal and distal tubules. This pharmacological action results in excretion of these ions, increased urinary output, and reduction in extracellular fluid. This compound has been classified as a loop or high ceiling diuretic.. etacrynic acid : An aromatic ether that is phenoxyacetic acid in which the phenyl ring is substituted by chlorines at positions 2 and 3, and by a 2-methylidenebutanoyl group at position 4. It is a loop diuretic used to treat high blood pressure resulting from diseases such as congestive heart failure, liver failure, and kidney failure. It is also a glutathione S-transferase (EC 2.5.1.18) inhibitor.	2.21	1	0	aromatic ether; aromatic ketone; dichlorobenzene; monocarboxylic acid	EC 2.5.1.18 (glutathione transferase) inhibitor; ion transport inhibitor; loop diuretic
ethylenediamine ethylenediamine: RN given refers to parent cpd; edamine is the recommended contraction for the ethylenediamine radical. ethylenediamine : An alkane-alpha,omega-diamine in which the alkane is ethane.	2.06	1	0	alkane-alpha,omega-diamine	GABA agonist
fluorescite fluorescein (acid form) : A xanthene dye that is highly fluorescent and commonly used as a fluorescent tracer.	2.03	1	0	benzoic acids; cyclic ketone; hydroxy monocarboxylic acid; organic heterotricyclic compound; phenols; xanthene dye	fluorescent dye; radioopaque medium
fluoxetine Fluoxetine: The first highly specific serotonin uptake inhibitor. It is used as an antidepressant and often has a more acceptable side-effects profile than traditional antidepressants.. fluoxetine : A racemate comprising equimolar amounts of (R)- and (S)-fluoxetine. A selective serotonin reuptake inhibitor (SSRI), it is used (generally as the hydrochloride salt) for the treatment of depression (and the depressive phase of bipolar disorder), bullimia nervosa, and obsessive-compulsive disorder.. N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine : An aromatic ether consisting of 4-trifluoromethylphenol in which the hydrogen of the phenolic hydroxy group is replaced by a 3-(methylamino)-1-phenylpropyl group.	7.02	1	0	(trifluoromethyl)benzenes; aromatic ether; secondary amino compound
furosemide Furosemide: A benzoic-sulfonamide-furan. It is a diuretic with fast onset and short duration that is used for EDEMA and chronic RENAL INSUFFICIENCY.. furosemide : A chlorobenzoic acid that is 4-chlorobenzoic acid substituted by a (furan-2-ylmethyl)amino and a sulfamoyl group at position 2 and 5 respectively. It is a diuretic used in the treatment of congestive heart failure.	2.41	1	0	chlorobenzoic acid; furans; sulfonamide	environmental contaminant; loop diuretic; xenobiotic
fusaric acid Fusaric Acid: A picolinic acid derivative isolated from various Fusarium species. It has been proposed for a variety of therapeutic applications but is primarily used as a research tool. Its mechanisms of action are poorly understood. It probably inhibits DOPAMINE BETA-HYDROXYLASE, the enzyme that converts dopamine to norepinephrine. It may also have other actions, including the inhibition of cell proliferation and DNA synthesis.	1.96	1	0	aromatic carboxylic acid; pyridines
gentamicin Gentamicins: A complex of closely related aminoglycosides obtained from MICROMONOSPORA purpurea and related species. They are broad-spectrum antibiotics, but may cause ear and kidney damage. They act to inhibit PROTEIN BIOSYNTHESIS.	2.13	1	0
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	2.03	1	0	monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; radical scavenger; xenobiotic
isoproterenol Isoproterenol: Isopropyl analog of EPINEPHRINE; beta-sympathomimetic that acts on the heart, bronchi, skeletal muscle, alimentary tract, etc. It is used mainly as bronchodilator and heart stimulant.. isoprenaline : A secondary amino compound that is noradrenaline in which one of the hydrogens attached to the nitrogen is replaced by an isopropyl group. A sympathomimetic acting almost exclusively on beta-adrenergic receptors, it is used (mainly as the hydrochloride salt) as a bronghodilator and heart stimulant for the management of a variety of cardiac disorders.	1.96	1	0	catechols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; sympathomimetic agent
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.	2.21	1	0	dichlorobenzene; dioxolane; ether; imidazoles; N-acylpiperazine; N-arylpiperazine
kojic acid [no description available]	2.13	1	0	4-pyranones; enol; primary alcohol	Aspergillus metabolite; EC 1.10.3.1 (catechol oxidase) inhibitor; EC 1.10.3.2 (laccase) inhibitor; EC 1.13.11.24 (quercetin 2,3-dioxygenase) inhibitor; EC 1.14.18.1 (tyrosinase) inhibitor; EC 1.4.3.3 (D-amino-acid oxidase) inhibitor; NF-kappaB inhibitor; skin lightening agent
benzylsuccinic acid benzylsuccinic acid: inhibitor of carboxypeptidase A. 2-benzylsuccinic acid : A dicarboxylic acid consisting of succinic acid carrying a 2-benzyl substituent.	2.4	2	0	dicarboxylic acid	bacterial xenobiotic metabolite
loratadine Loratadine: A second-generation histamine H1 receptor antagonist used in the treatment of allergic rhinitis and urticaria. Unlike most classical antihistamines (HISTAMINE H1 ANTAGONISTS) it lacks central nervous system depressing effects such as drowsiness.. loratadine : A benzocycloheptapyridine that is 6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine substituted by a chloro group at position 8 and a 1-(ethoxycarbonyl)piperidin-4-ylidene group at position 11. It is a H1-receptor antagonist commonly employed in the treatment of allergic disorders.	2.02	1	0	benzocycloheptapyridine; ethyl ester; N-acylpiperidine; organochlorine compound; tertiary carboxamide	anti-allergic agent; cholinergic antagonist; geroprotector; H1-receptor antagonist
loxoprofen loxoprofen: RN given refers to parent cpd without isomeric designation; structure in first source. loxoprofen : A monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-[(2-oxocyclopentyl)methyl]phenyl group. A prodrug that is rapidly converted into its active trans-alcohol metabolite following oral administration.	7.25	1	0	cyclopentanones; monocarboxylic acid	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug
miconazole Miconazole: An imidazole antifungal agent that is used topically and by intravenous infusion.. 1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole : A member of the class of imidazoles that is 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanol in which the hydroxyl hydrogen is replaced by a 2,4-dichlorobenzyl group.. miconazole : A racemate composed of equimolar amounts of (R)- and (S)-miconazole. Used (as its nitrate salt) to treat skin infections such as athlete's foot, jock itch, ringworm and other fungal skin infections. It inhibits the synthesis of ergosterol, a critical component of fungal cell membranes.	2.44	2	0	dichlorobenzene; ether; imidazoles
midazolam Midazolam: A short-acting hypnotic-sedative drug with anxiolytic and amnestic properties. It is used in dentistry, cardiac surgery, endoscopic procedures, as preanesthetic medication, and as an adjunct to local anesthesia. The short duration and cardiorespiratory stability makes it useful in poor-risk, elderly, and cardiac patients. It is water-soluble at pH less than 4 and lipid-soluble at physiological pH.. midazolam : An imidazobenzodiazepine that is 4H-imidazo[1,5-a][1,4]benzodiazepine which is substituted by a methyl, 2-fluorophenyl and chloro groups at positions 1, 6 and 8, respectively.	3.99	1	1	imidazobenzodiazepine; monofluorobenzenes; organochlorine compound	anticonvulsant; antineoplastic agent; anxiolytic drug; apoptosis inducer; central nervous system depressant; GABAA receptor agonist; general anaesthetic; muscle relaxant; sedative
ethylmaleimide Ethylmaleimide: A sulfhydryl reagent that is widely used in experimental biochemical studies.	2.88	4	0	maleimides	anticoronaviral agent; EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.1.1 (hexokinase) inhibitor
nafronyl Nafronyl: A drug used in the management of peripheral and cerebral vascular disorders. It is claimed to enhance cellular oxidative capacity and to be a spasmolytic. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1310) It may also be an antagonist at 5HT-2 serotonin receptors.	1.98	1	0	naphthalenes
naftopidil [no description available]	2.66	2	0	piperazines
nalidixic acid [no description available]	1.96	1	0	1,8-naphthyridine derivative; monocarboxylic acid; quinolone antibiotic	antibacterial drug; antimicrobial agent; DNA synthesis inhibitor
norfloxacin Norfloxacin: A synthetic fluoroquinolone (FLUOROQUINOLONES) with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin inhibits bacterial DNA GYRASE.. norfloxacin : A quinolinemonocarboxylic acid with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase.	2.13	1	0	fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antibacterial drug; DNA synthesis inhibitor; environmental contaminant; xenobiotic
omeprazole Omeprazole: A 4-methoxy-3,5-dimethylpyridyl, 5-methoxybenzimidazole derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits an H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS.. omeprazole : A racemate comprising equimolar amounts of (R)- and (S)-omeprazole.. 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole : A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted by a [4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl group at position 2 and a methoxy group at position 5.	2.07	1	0	aromatic ether; benzimidazoles; pyridines; sulfoxide
oxonic acid Oxonic Acid: Antagonist of urate oxidase.	3.14	1	0	1,3,5-triazines; monocarboxylic acid
oxybutynin oxybutynin: RN given refers to parent cpd. oxybutynin : A racemate comprising equimolar amounts of (R)-oxybutynin and esoxybutynin. An antispasmodic used for the treatment of overactive bladder.	2.02	1	0	acetylenic compound; carboxylic ester; racemate; tertiary alcohol; tertiary amino compound	antispasmodic drug; calcium channel blocker; local anaesthetic; muscarinic antagonist; muscle relaxant; parasympatholytic
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).	3.11	1	0	1,4-benzoquinones	cofactor; human xenobiotic metabolite; mouse metabolite
patulin Patulin: 4-Hydroxy-4H-furo(3,2-c)pyran-2(6H)-one. A mycotoxin produced by several species of Aspergillus and Penicillium. It is found in unfermented apple and grape juice and field crops. It has antibiotic properties and has been shown to be carcinogenic and mutagenic and causes chromosome damage in biological systems.. patulin : A furopyran and lactone that is (2H-pyran-3(6H)-ylidene)acetic acid which is substituted by hydroxy groups at positions 2 and 4 and in which the hydroxy group at position 4 has condensed with the carboxy group to give the corresponding bicyclic lactone. A mycotoxin produced by several species of Aspergillus and Penicillium, it has antibiotic properties but has been shown to be carcinogenic and mutagenic.	7.01	1	0	furopyran; gamma-lactone; lactol	antimicrobial agent; Aspergillus metabolite; carcinogenic agent; mutagen; mycotoxin; Penicillium metabolite
piperazine [no description available]	2.5	2	0	azacycloalkane; piperazines; saturated organic heteromonocyclic parent	anthelminthic drug
piracetam Piracetam: A compound suggested to be both a nootropic and a neuroprotective agent.	1.98	1	0	organonitrogen compound; organooxygen compound
probenecid Probenecid: The prototypical uricosuric agent. It inhibits the renal excretion of organic anions and reduces tubular reabsorption of urate. Probenecid has also been used to treat patients with renal impairment, and, because it reduces the renal tubular excretion of other drugs, has been used as an adjunct to antibacterial therapy.. probenecid : A sulfonamide in which the nitrogen of 4-sulfamoylbenzoic acid is substituted with two propyl groups.	2.03	1	0	benzoic acids; sulfonamide	uricosuric drug
propofol Propofol: An intravenous anesthetic agent which has the advantage of a very rapid onset after infusion or bolus injection plus a very short recovery period of a couple of minutes. (From Smith and Reynard, Textbook of Pharmacology, 1992, 1st ed, p206). Propofol has been used as ANTICONVULSANTS and ANTIEMETICS.. propofol : A phenol resulting from the formal substitution of the hydrogen at the 2 position of 1,3-diisopropylbenzene by a hydroxy group.	2.05	1	0	phenols	anticonvulsant; antiemetic; intravenous anaesthetic; radical scavenger; sedative
saccharin Saccharin: Flavoring agent and non-nutritive sweetener.. saccharin : A 1,2-benzisothiazole having a keto-group at the 3-position and two oxo substituents at the 1-position. It is used as an artificial sweetening agent.	7.76	2	0	1,2-benzisothiazole; N-sulfonylcarboxamide	environmental contaminant; sweetening agent; xenobiotic
sebacic acid sebacic acid : An alpha,omega-dicarboxylic acid that is the 1,8-dicarboxy derivative of octane.	3.1	5	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	human metabolite; plant metabolite
vorinostat Vorinostat: A hydroxamic acid and anilide derivative that acts as a HISTONE DEACETYLASE inhibitor. It is used in the treatment of CUTANEOUS T-CELL LYMPHOMA and SEZARY SYNDROME.. vorinostat : A dicarboxylic acid diamide comprising suberic (octanedioic) acid coupled to aniline and hydroxylamine. A histone deacetylase inhibitor, it is marketed under the name Zolinza for the treatment of cutaneous T cell lymphoma (CTCL).	2.04	1	0	dicarboxylic acid diamide; hydroxamic acid	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor
sulfanilamide [no description available]	2.05	1	0	substituted aniline; sulfonamide antibiotic; sulfonamide	antibacterial agent; drug allergen; EC 4.2.1.1 (carbonic anhydrase) inhibitor
sulfasalazine Sulfasalazine: A drug that is used in the management of inflammatory bowel diseases. Its activity is generally considered to lie in its metabolic breakdown product, 5-aminosalicylic acid (see MESALAMINE) released in the colon. (From Martindale, The Extra Pharmacopoeia, 30th ed, p907). sulfasalazine : An azobenzene consisting of diphenyldiazene having a carboxy substituent at the 4-position, a hydroxy substituent at the 3-position and a 2-pyridylaminosulphonyl substituent at the 4'-position.	3.1	1	0
tazarotene tazarotene: a topical acetylenic retinoid; a topical kerytolytic. tazarotene : The ethyl ester of tazarotenic acid. A prodrug for tazarotenic acid, it is used for the treatment of psoriasis, acne, and sun-damaged skin.	3.12	1	0	acetylenic compound; ethyl ester; pyridines; retinoid; thiochromane	keratolytic drug; prodrug; teratogenic agent
terbutaline Terbutaline: A selective beta-2 adrenergic agonist used as a bronchodilator and tocolytic.. terbutaline : A member of the class of phenylethanolamines that is catechol substituted at position 5 by a 2-(tert-butylamino)-1-hydroxyethyl group.	2.06	1	0	phenylethanolamines; resorcinols	anti-asthmatic drug; beta-adrenergic agonist; bronchodilator agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; hypoglycemic agent; sympathomimetic agent; tocolytic agent
thalidomide Thalidomide: A piperidinyl isoindole originally introduced as a non-barbiturate hypnotic, but withdrawn from the market due to teratogenic effects. It has been reintroduced and used for a number of immunological and inflammatory disorders. Thalidomide displays immunosuppressive and anti-angiogenic activity. It inhibits release of TUMOR NECROSIS FACTOR-ALPHA from monocytes, and modulates other cytokine action.. thalidomide : A racemate comprising equimolar amounts of R- and S-thalidomide.. 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione : A dicarboximide that is isoindole-1,3(2H)-dione in which the hydrogen attached to the nitrogen is substituted by a 2,6-dioxopiperidin-3-yl group.	2.21	1	0	phthalimides; piperidones
thiabendazole Tresaderm: dermatologic soln containing dexamethasone, thiabendazole & neomycin sulfate	2.45	2	0	1,3-thiazoles; benzimidazole fungicide; benzimidazoles	antifungal agrochemical; antinematodal drug
thenoyltrifluoroacetone Thenoyltrifluoroacetone: Chelating agent and inhibitor of cellular respiration.	2.68	3	0
tyramine [no description available]	2.67	3	0	monoamine molecular messenger; primary amino compound; tyramines	EC 3.1.1.8 (cholinesterase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter
tyrphostin a9 [no description available]	2	1	0	alkylbenzene	geroprotector
zonisamide Zonisamide: A benzisoxazole and sulfonamide derivative that acts as a CALCIUM CHANNEL blocker. It is used primarily as an adjunctive antiepileptic agent for the treatment of PARTIAL SEIZURES, with or without secondary generalization.. zonisamide : A 1,2-benzoxazole compound having a sulfamoylmethyl substituent at the 3-position.	2.05	1	0	1,2-benzoxazoles; sulfonamide	anticonvulsant; antioxidant; central nervous system drug; protective agent; T-type calcium channel blocker
mitomycin Mitomycin: An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.. mitomycin : A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.	6.96	1	0	mitomycin	alkylating agent; antineoplastic agent
prednisolone Prednisolone: A glucocorticoid with the general properties of the corticosteroids. It is the drug of choice for all conditions in which routine systemic corticosteroid therapy is indicated, except adrenal deficiency states.. prednisolone : A glucocorticoid that is prednisone in which the oxo group at position 11 has been reduced to the corresponding beta-hydroxy group. It is a drug metabolite of prednisone.	3.99	1	1	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antineoplastic agent; drug metabolite; environmental contaminant; immunosuppressive agent; xenobiotic
sorbitol D-glucitol : The D-enantiomer of glucitol (also known as D-sorbitol).	1.98	1	0	glucitol	cathartic; Escherichia coli metabolite; food humectant; human metabolite; laxative; metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite; sweetening agent
adrenochrome Adrenochrome: Pigment obtained by the oxidation of epinephrine.	6.93	1	0	indoles
methyldimethylaminoazobenzene Methyldimethylaminoazobenzene: A very potent liver carcinogen.. 3-methyl-4'-dimethylaminoazobenzene : A member of the class of azobenzenes that is azobenzene in which one of the phenyl groups is substituted at position 3 by a methyl group, while the other is substituted at position 4 by a dimethylamino group. It is a potent liver carcinogen.	1.97	1	0
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.	1.98	1	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
alanine Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.	4.46	7	0	alanine zwitterion; alanine; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid	EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor; fundamental metabolite
serine Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.	2.43	2	0	L-alpha-amino acid; proteinogenic amino acid; serine family amino acid; serine zwitterion; serine	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	2.38	2	0	C-nitro compound; carboxamide; diol; organochlorine compound	antibacterial drug; antimicrobial agent; Escherichia coli metabolite; geroprotector; Mycoplasma genitalium metabolite; protein synthesis inhibitor
aspartic acid Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.	5.77	28	0	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
glutamine Glutamine: A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from GLUTAMIC ACID and AMMONIA. It is the principal carrier of NITROGEN in the body and is an important energy source for many cells.. L-glutamine : An optically active form of glutamine having L-configuration.. glutamine : An alpha-amino acid that consists of butyric acid bearing an amino substituent at position 2 and a carbamoyl substituent at position 4.	4.91	8	1	amino acid zwitterion; glutamine family amino acid; glutamine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
lysine Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.	2.93	4	0	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
allyl isothiocyanate allyl isothiocyanate: used in the manufacture of flavors, war gases; medical use as a counterirritant; structure. allyl isothiocyanate : An isothiocyanate with the formula CH2=CHCH2N=C=S. A colorless oil with boiling point 152degreeC, it is responsible for the pungent taste of mustard, horseradish, and wasabi.	7.05	1	0	alkenyl isothiocyanate; isothiocyanate	antimicrobial agent; antineoplastic agent; apoptosis inducer; lachrymator; metabolite
cyanides Cyanides: Inorganic salts of HYDROGEN CYANIDE containing the -CN radical. The concept also includes isocyanides. It is distinguished from NITRILES, which denotes organic compounds containing the -CN radical.. cyanides : Salts and C-organyl derivatives of hydrogen cyanide, HC#N.. isocyanide : The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)).. cyanide : A pseudohalide anion that is the conjugate base of hydrogen cyanide.	2.36	2	0	pseudohalide anion	EC 1.9.3.1 (cytochrome c oxidase) inhibitor
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	3.04	4	0	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening 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.	2.39	2	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.	2.39	2	0	tetrachlorophenol	xenobiotic metabolite
kanamycin a Kanamycin: Antibiotic complex produced by Streptomyces kanamyceticus from Japanese soil. Comprises 3 components: kanamycin A, the major component, and kanamycins B and C, the minor components.. kanamycin : Kanamycin is a naturally occurring antibiotic complex from Streptomyces kanamyceticus that consists of several components: kanamycin A, the major component (also usually designated as kanamycin), and kanamycins B, C, D and X the minor components.	2.13	1	0	kanamycins	bacterial metabolite
carbostyril Quinolones: A group of derivatives of naphthyridine carboxylic acid, quinoline carboxylic acid, or NALIDIXIC ACID.. quinolin-2(1H)-one : A quinolone that is 1,2-dihydroquinoline substituted by an oxo group at position 2.	4.91	4	0	monohydroxyquinoline; quinolone	bacterial xenobiotic metabolite
edetic acid Edetic Acid: A chelating agent that sequesters a variety of polyvalent cations such as CALCIUM. It is used in pharmaceutical manufacturing and as a food additive.	3.1	5	0	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	1.97	1	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
cysteamine Cysteamine: A mercaptoethylamine compound that is endogenously derived from the COENZYME A degradative pathway. The fact that cysteamine is readily transported into LYSOSOMES where it reacts with CYSTINE to form cysteine-cysteamine disulfide and CYSTEINE has led to its use in CYSTINE DEPLETING AGENTS for the treatment of CYSTINOSIS.. cysteamine : An amine that consists of an ethane skeleton substituted with a thiol group at C-1 and an amino group at C-2.	1.98	1	0	amine; thiol	geroprotector; human metabolite; mouse metabolite; radiation protective agent
adenosine monophosphate Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.	3.27	6	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
aniline [no description available]	2.03	1	0	anilines; primary arylamine
dimethylnitrosamine Dimethylnitrosamine: A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties. It causes serious liver damage and is a hepatocarcinogen in rodents.	1.98	1	0	nitrosamine	geroprotector; mutagen
lactose Lactose: A disaccharide of GLUCOSE and GALACTOSE in human and cow milk. It is used in pharmacy for tablets, in medicine as a nutrient, and in industry.. lactose : A glycosylglucose disaccharide, found most notably in milk, that consists of D-galactose and D-glucose fragments bonded through a beta-1->4 glycosidic linkage. The glucose fragment can be in either the alpha- or beta-pyranose form, whereas the galactose fragment can only have the beta-pyranose form.. beta-lactose : The beta-anomer of lactose.	2.4	2	0	lactose
methionine Methionine: A sulfur-containing essential L-amino acid that is important in many body functions.. methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4.	2.02	1	0	aspartate family amino acid; L-alpha-amino acid; methionine zwitterion; methionine; proteinogenic amino acid	antidote to paracetamol poisoning; human metabolite; micronutrient; mouse metabolite; nutraceutical
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.	2.01	1	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; phenylalanine; proteinogenic amino acid	algal metabolite; EC 3.1.3.1 (alkaline phosphatase) inhibitor; Escherichia coli metabolite; human xenobiotic metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
barbituric acid barbituric acid: RN given refers to parent cpd; structure from Merck Index, 9th ed, #966. barbituric acid : A barbiturate, the structure of which is that of perhydropyrimidine substituted at C-2, -4 and -6 by oxo groups. Barbituric acid is the parent compound of barbiturate drugs, although it is not itself pharmacologically active.	2	1	0	barbiturates	allergen; xenobiotic
norethindrone Norethindrone: A synthetic progestational hormone with actions similar to those of PROGESTERONE but functioning as a more potent inhibitor of ovulation. It has weak estrogenic and androgenic properties. The hormone has been used in treating amenorrhea, functional uterine bleeding, endometriosis, and for CONTRACEPTION.. norethisterone : A 17beta-hydroxy steroid that is testosterone in which the hydrogen at position 17 is replaced by an ethynyl group and in which the methyl group attached to position 10 is replaced by hydrogen.	1.96	1	0	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; terminal acetylenic compound; tertiary alcohol	progestin; synthetic oral contraceptive
ampicillin Ampicillin: Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.. ampicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group.	2.45	2	0	beta-lactam antibiotic; penicillin allergen; penicillin	antibacterial drug
mannitol [no description available]	2.81	3	0	mannitol	allergen; antiglaucoma drug; compatible osmolytes; Escherichia coli metabolite; food anticaking agent; food bulking agent; food humectant; food stabiliser; food thickening agent; hapten; metabolite; osmotic diuretic; sweetening agent
asparagine Asparagine: A non-essential amino acid that is involved in the metabolic control of cell functions in nerve and brain tissue. It is biosynthesized from ASPARTIC ACID and AMMONIA by asparagine synthetase. (From Concise Encyclopedia Biochemistry and Molecular Biology, 3rd ed). asparagine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 2-amino-2-oxoethyl group.	2.66	2	0	amino acid zwitterion; asparagine; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
histidine Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.	3.26	6	0	amino acid zwitterion; histidine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
mestranol [no description available]	1.96	1	0	17beta-hydroxy steroid; aromatic ether; terminal acetylenic compound	prodrug; xenoestrogen
isoleucine Isoleucine: An essential branched-chain aliphatic amino acid found in many proteins. It is an isomer of LEUCINE. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels.. isoleucine : A 2-amino-3-methylpentanoic acid having either (2R,3R)- or (2S,3S)-configuration.. L-isoleucine : The L-enantiomer of isoleucine.	2.36	2	0	aspartate family amino acid; isoleucine; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
4-chlorobenzoic acid 4-chlorobenzoic acid: RN given refers to parent cpd. 4-chlorobenzoic acid : A monochlorobenzoic acid carrying a chloro substituent at position 4.	2.02	1	0	monochlorobenzoic acid	bacterial xenobiotic 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.	8.08	5	0	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
ethylene Plastipore: high density polyethylene sponge biocompatible material; used as posts in dental bridges	2.01	1	0	alkene; gas molecular entity	plant hormone; refrigerant
acetylene [no description available]	2	1	0	alkyne; gas molecular entity; terminal acetylenic compound
propane Propane: A three carbon alkane with the formula H3CCH2CH3.	2	1	0	alkane; gas molecular entity	food propellant
methylene chloride Methylene Chloride: A chlorinated hydrocarbon that has been used as an inhalation anesthetic and acts as a narcotic in high concentrations. Its primary use is as a solvent in manufacturing and food technology.. dichloromethane : A member of the class of chloromethanes that is methane in which two of the hydrogens have been replaced by chlorine. A dense, non-flammible colourless liquid at room temperature (b.p. 40degreeC, d = 1.33) which is immiscible with water, it is widely used as a solvent, a paint stripper, and for the removal of caffeine from coffee and tea.	2.41	1	0	chloromethanes; volatile organic compound	carcinogenic agent; polar aprotic solvent; refrigerant
quinic acid (-)-quinic acid : The (-)-enantiomer of quinic acid.	2.78	3	0
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.	2.02	1	0	chloroethenes	inhalation anaesthetic; mouse metabolite
acrylamide [no description available]	2.02	1	0	acrylamides; N-acylammonia; primary carboxamide	alkylating agent; carcinogenic agent; Maillard reaction product; mutagen; neurotoxin
acrylic acid acrylic acid: RN given refers to parent cpd. acrylic acid : A alpha,beta-unsaturated monocarboxylic acid that is ethene substituted by a carboxy group.	2.44	2	0	alpha,beta-unsaturated monocarboxylic acid	metabolite
rotenone Derris: A plant genus of the family FABACEAE. The root is a source of rotenoids (ROTENONE) and flavonoids. Some species of Pongamia have been reclassified to this genus and some to MILLETTIA. Some species of Deguelia have been reclassified to this genus.. rotenoid : Members of the class of tetrahydrochromenochromene that consists of a cis-fused tetrahydrochromeno[3,4-b]chromene skeleton and its substituted derivatives. The term was originally restricted to natural products, but is now also used to describe semi-synthetic and fully synthetic compounds.	2.68	3	0	organic heteropentacyclic compound; rotenones	antineoplastic agent; metabolite; mitochondrial NADH:ubiquinone reductase inhibitor; phytogenic insecticide; piscicide; toxin
9,10-anthraquinone 9,10-anthraquinone : An anthraquinone that is anthracene in which positions 9 and 10 have been oxidised to carbonyls.	7.06	1	0	anthraquinone
xylitol xylooligosaccharide: structure in first source. pentitol : An alditol obtained by reduction of any pentose.. xylooligosaccharide : An oligosaccharide comprised of xylose residues.	2.48	2	0
n-vinyl-2-pyrrolidinone N-vinyl-2-pyrrolidinone: monomer of POVIDONE; structure given in first source	2.46	2	0	pyrrolidin-2-ones
2-furoic acid 2-furoic acid: RN given refers to parent cpd. furoic acid : A monocarboxylic acid that consists of a furan ring having a single carboxylic acid group on any ring position and derivatives thereof.. 2-furoic acid : A furoic acid having the carboxylic acid group located at position 2.	2.06	1	0	furoic acid	bacterial xenobiotic metabolite; human xenobiotic metabolite; inhibitor; plant metabolite; Saccharomyces cerevisiae metabolite
1-naphthylphenylamine N-phenyl-1-naphthylamine: RN given refers to 1-naphthylamine cpd; structure	1.97	1	0	naphthalenes
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.	1.97	1	0	hydroxybiphenyls	antifungal agrochemical; environmental food contaminant
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)	2.13	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.	2.41	2	0	xylene
styrene oxide styrene oxide: structure. styrene oxide : An epoxide that is oxirane in which one of the hydrogens has been replaced by a phenyl group.	2.21	1	0	epoxide	human xenobiotic metabolite
4-butyrolactone 4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.	2.03	1	0	butan-4-olide	metabolite; neurotoxin
sulfosalicylic acid 5-sulfosalicylic acid : An arenesulfonic acid that is benzoic acid substituted by a hydroxy at position C-2 and a sulfo group at C-5.	2.1	1	0	arenesulfonic acid; benzoic acids; phenols	metabolite
furaldehyde Furaldehyde: A heterocyclic compound consisting of a furan where the hydrogen at position 2 is substituted by a formyl group.. furfural : An aldehyde that is furan with the hydrogen at position 2 substituted by a formyl group.	2.13	1	0	aldehyde; furans	Maillard reaction product; metabolite
pyrrolidonecarboxylic acid Pyrrolidonecarboxylic Acid: A cyclized derivative of L-GLUTAMIC ACID. Elevated blood levels may be associated with problems of GLUTAMINE or GLUTATHIONE metabolism.. 5-oxo-L-proline : An optically active form of 5-oxoproline having L-configuration.	2.49	2	0	5-oxoproline; L-proline derivative; non-proteinogenic L-alpha-amino acid	algal metabolite
dimethyl-4-phenylenediamine dimethyl-4-phenylenediamine: RN given refers to parent cpd; structure	1.99	1	0	diamine; substituted aniline
terephthalic acid terephthalic acid: RN given refers to 1,4-benzenedicarboxylic acid. terephthalic acid : A benzenedicarboxylic acid carrying carboxy groups at positions 1 and 4. One of three possible isomers of benzenedicarboxylic acid, the others being phthalic and isophthalic acids.	1.98	1	0	benzenedicarboxylic acid
2,5-pyridinedicarboxylic acid 2,5-Pyridinedicarboxylic acid: RN given refers to parent cpd. isocinchomeronic acid : A pyridinedicarboxylic acid carrying carboxy groups at positions 2 and 5.	2.04	1	0	pyridinedicarboxylic acid
ethylbenzene [no description available]	3.12	1	0	alkylbenzene
anisole anisole : A monomethoxybenzene that is benzene substituted by a methoxy group.	2.02	1	0	monomethoxybenzene	plant metabolite
dimethyl succinate dimethyl succinate: potent insulin secretagogue	2.46	2	0	fatty acid methyl ester
acrolein [no description available]	2.06	1	0	enal	herbicide; human xenobiotic metabolite; toxin
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	2.01	1	0	alkane
maleic anhydride Maleic Anhydrides: Used in copolymerization reactions, in the Diels-Alder(diene)synthesis, in the preparation of resins, pharmaceuticals and agricultural chemicals. It is a powerful irritant and causes burns.. maleic anhydride : A cyclic dicarboxylic anhydride that is the cyclic anhydride of maleic acid.	7.44	2	0	cyclic dicarboxylic anhydride; furans	allergen
3-xylene m-xylene : A xylene carrying methyl groups at positions 1 and 3.	2.02	1	0	xylene
succinamide [no description available]	2.05	1	0
n-hexane hexane : An unbranched alkane containing six carbon atoms.	2.01	1	0	alkane; volatile organic compound	neurotoxin; non-polar solvent
piperidine [no description available]	2.11	1	0	azacycloalkane; piperidines; saturated organic heteromonocyclic parent; secondary amine	base; catalyst; human metabolite; non-polar solvent; plant metabolite; protic solvent; reagent
heptanoic acid heptanoic acid : A C7, straight-chain fatty acid that contributes to the odour of some rancid oils. Used in the preparation of esters for the fragrance industry, and as an additive in cigarettes.	2.03	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	plant metabolite
2-methylbutanoic acid 2-methylbutanoic acid: RN given refers to parent cpd without isomeric designation. 2-methylbutyric acid : A methylbutyric acid comprising a butyric acid core carrying a 2-methyl substituent. Produced from amino acid leucine during nutrient starvation in bacteria.	2.03	1	0	methylbutyric acid	bacterial metabolite; human metabolite
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.	2.07	1	0	diester; phthalate ester	androstane receptor agonist; apoptosis inhibitor; plasticiser
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.	6.92	1	0	acene; anthracenes; ortho-fused tricyclic hydrocarbon
vanillic acid Vanillic Acid: A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13).. vanillic acid : A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3.	3.19	5	0	methoxybenzoic acid; monohydroxybenzoic acid	plant metabolite
meglumine Meglumine: 1-Deoxy-1-(methylamino)-D-glucitol. A derivative of sorbitol in which the hydroxyl group in position 1 is replaced by a methylamino group. Often used in conjunction with iodinated organic compounds as contrast medium.. N-methylglucamine : A hexosamine that is D-glucitol in which the hydroxy group at position 1 is substituted by the nitrogen of a methylamino group. A crystalline base, it is used in preparing salts of certain acids for use as diagnostic radiopaque media, while its antimonate is used as an antiprotozoal in the treatment of leishmaniasis.	2.15	1	0	hexosamine; secondary amino compound
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.	1.97	1	0	naphthylamine	human xenobiotic metabolite
2-naphthol 2-naphthol: RN given refers to parent cpd. 2-naphthol : A naphthol carrying a hydroxy group at position 2.. naphthols : Any hydroxynaphthalene derivative that has a single hydroxy substituent.	2.39	2	0	naphthol	antinematodal drug; genotoxin; human urinary metabolite; human xenobiotic metabolite; mouse metabolite; radical scavenger
2-ethylhexanoic acid 2-ethylhexanoic acid: structure in first source; wood preservative; 2-ethylhexanoic acid is active ingredient in Sinesto B	2.03	1	0	branched-chain fatty acid
shikimic acid Shikimic Acid: A tri-hydroxy cyclohexene carboxylic acid important in biosynthesis of so many compounds that the shikimate pathway is named after it.. shikimic acid : A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3R,4S,5R stereoisomer). It is an intermediate metabolite in plants and microorganisms.	2.99	4	0	alpha,beta-unsaturated monocarboxylic acid; cyclohexenecarboxylic acid; hydroxy monocarboxylic acid	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
protocatechualdehyde protocatechualdehyde: found in wheat grains, wheat seedlings, & other plants; RN given refers to parent cpd; see also rancinamycins; structure	2.02	1	0	dihydroxybenzaldehyde
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	2.06	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.	2.42	2	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).	2.41	1	0	alkane; volatile organic compound	non-polar solvent; plant metabolite
potassium cyanide [no description available]	2.67	3	0	cyanide salt; one-carbon compound; potassium salt	EC 1.15.1.1 (superoxide dismutase) inhibitor; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; neurotoxin
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.	2.07	1	0	catechin	antioxidant; plant metabolite
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.	2.05	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
indazoles Indazoles: A group of heterocyclic aromatic organic compounds consisting of the fusion of BENZENE and PYRAZOLES.	3.99	1	1	indazole
benzoxazoles 1,3-benzoxazole : A benzoxazole in which the benzene ring is fused to a 1,3-oxazole ring across positions 4 and 5.. benzoxazole : Compounds based on a fused 1,2- or 1,3-oxazole and benzene bicyclic ring skeleton.	2.17	1	0	1,3-benzoxazoles; mancude organic heterobicyclic parent
oxazoles Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.	2.1	1	0	1,3-oxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiazoles [no description available]	4.32	4	1	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
triphenyltetrazolium triphenyltetrazolium: RN given refers to parent cpd. 2,3,5-triphenyltetrazolium : An organic cation that is tetrazole carrying three phenyl substituents at positions 2, 3 and 5.	2.39	2	0	organic cation
calcium gluconate [no description available]	2.02	1	0	calcium salt	nutraceutical
hydrazine diamine : Any polyamine that contains two amino groups.	1.94	1	0	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
4-hydroxyphenyllactic acid 4-hydroxyphenyllactic acid: tyrosing metabolite; RN given refers to cpd without isomeric designation. 3-(4-hydroxyphenyl)lactic acid : A 2-hydroxy carboxylic acid that is lactic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group.	2.03	1	0	2-hydroxy carboxylic acid; phenols	bacterial metabolite; human metabolite
aminoimidazole carboxamide Aminoimidazole Carboxamide: An imidazole derivative which is a metabolite of the antineoplastic agents BIC and DIC. By itself, or as the ribonucleotide, it is used as a condensation agent in the preparation of nucleosides and nucleotides. Compounded with orotic acid, it is used to treat liver diseases.. 5-aminoimidazole-4-carboxamide : An aminoimidazole in which the amino group is at C-5 with a carboxamido group at C-4.	2.39	2	0	aminoimidazole; monocarboxylic acid amide	mouse metabolite
citrulline citrulline : The parent compound of the citrulline class consisting of ornithine having a carbamoyl group at the N(5)-position.	6.94	1	0	amino acid zwitterion; citrulline	Daphnia magna metabolite; EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; protective agent; Saccharomyces cerevisiae metabolite
betamethasone Betamethasone: A glucocorticoid given orally, parenterally, by local injection, by inhalation, or applied topically in the management of various disorders in which corticosteroids are indicated. Its lack of mineralocorticoid properties makes betamethasone particularly suitable for treating cerebral edema and congenital adrenal hyperplasia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p724)	7.21	1	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; fluorinated steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	anti-asthmatic agent; anti-inflammatory drug; immunosuppressive agent
cyanogen cyanogen: structure. oxalonitrile : A dinitrile that is ethane substituted by two cyano groups.	2.41	1	0	dinitrile; pseudohalogen
propiolic acid propiolic acid: RN given refers to parent cpd; structure. propynoic acid : A terminal acetylenic compound that is a 3-carbon, straight-chain, monounsaturated fatty acid having one acetylenic bond.	2.15	1	0	acetylenic fatty acid; alpha,beta-unsaturated monocarboxylic acid; monounsaturated fatty acid; short-chain fatty acid; terminal acetylenic compound	xenobiotic metabolite
funiculosin (anthraquinone) funiculosin (anthraquinone): see also a pyridone cpd called funiculosin; structure	1.97	1	0	trihydroxyanthraquinone
rhein [no description available]	2.08	1	0	dihydroxyanthraquinone
indole-3-carbaldehyde indole-3-carbaldehyde: metabolite of tryptophan; structure. indole-3-carbaldehyde : A heteroarenecarbaldehyde that is indole in which the hydrogen at position 3 has been replaced by a formyl group.	2.21	1	0	heteroarenecarbaldehyde; indole alkaloid; indoles	bacterial metabolite; human xenobiotic metabolite; marine metabolite; plant metabolite
3,4-pyridinedicarboxylic acid 3,4-pyridinedicarboxylic acid: structure in first source	2.04	1	0	pyridinedicarboxylic acid
2,4-pyridinedicarboxylic acid lutidinic acid : A pyridinedicarboxylic acid carrying carboxy groups at positions 2 and 4.	3.17	5	0	pyridinedicarboxylic acid
3,5-pyridinedicarboxylic acid 3,5-pyridinedicarboxylic acid: structure in first source	2.04	1	0	pyridinedicarboxylic acid
dipicolinic acid dipicolinic acid : A pyridinedicarboxylic acid carrying two carboxy groups at positions 2 and 6.	2.04	1	0	pyridinedicarboxylic acid	bacterial metabolite
4-hydroxyphenylethanol 4-hydroxyphenylethanol: in chest gland secretion of galagos. 2-(4-hydroxyphenyl)ethanol : A phenol substituted at position 4 by a 2-hydroxyethyl group.	2.05	1	0	phenols	anti-arrhythmia drug; antioxidant; cardiovascular drug; fungal metabolite; geroprotector; plant metabolite; protective agent
isovaleric acid isovaleric acid: structure. isovaleric acid : A C5, branched-chain saturated fatty acid.	2.03	1	0	branched-chain saturated fatty acid; methylbutyric acid; short-chain fatty acid	mammalian metabolite; plant metabolite
1,3-propanediol propane-1,3-diol : The simplest member of the class of propane-1,3-diols, consisting of propane in which one hydrogen from each methyl group is substituted by a hydroxy group. A colourless, viscous, water-miscible liquid with a high (210degreeC) boiling point, it is used in the synthesis of certain polymers and as a solvent and antifreeze.	2.02	1	0	propane-1,3-diols	metabolite; protic solvent
suberic acid suberic acid: used in plastics industry; inhibits activity of some enzymes; RN given refers to parent cpd; structure. suberic acid : An alpha,omega-dicarboxylic acid that is the 1,6-dicarboxy derivative of hexane.	2.7	3	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	human metabolite
oleanolic acid [no description available]	3.06	1	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	plant metabolite
abietic acid abietic acid : An abietane diterpenoid that is abieta-7,13-diene substituted by a carboxy group at position 18.	7.03	1	0	abietane diterpenoid; monocarboxylic acid	plant metabolite
gluconic acid gluconic acid: zinc gluconate has anti-inflammatory activity; RN given refers to (D)-isomer; all RRs refers to (D)-isomer unless otherwise noted. ketogluconic acid : A gluconic acid that contains a ketonic carbonyl group.. D-gluconic acid : A gluconic acid having D-configuration.	2.42	2	0	gluconic acid	chelator; Penicillium metabolite
copper gluconate Gluconates: Derivatives of gluconic acid (the structural formula HOCH2(CHOH)4COOH), including its salts and esters.	2.72	3	0	organic molecular entity
syringic acid syringic acid: RN given refers to parent cpd; structure in third source. syringic acid : A dimethoxybenzene that is 3,5-dimethyl ether derivative of gallic acid.	2.02	1	0	benzoic acids; dimethoxybenzene; phenols	plant metabolite
2-n-butylmalonate 2-n-butylmalonate: structure	1.96	1	0
senecioic acid senecioic acid: structure. 3-methylbut-2-enoic acid : A methyl-branched fatty acid that is but-2-enoic acid bearing a methyl substituent at position 3.	2.06	1	0	alpha,beta-unsaturated monocarboxylic acid; methyl-branched fatty acid; monounsaturated fatty acid; short-chain fatty acid	plant metabolite
gentian violet Gentian Violet: A dye that is a mixture of violet rosanilinis with antibacterial, antifungal, and anthelmintic properties.. crystal violet : An organic chloride salt that is the monochloride salt of crystal violet cation. It has been used in creams for the topical treatment of bacterial and fungal infections, being effective against some Gram-positive bacteria (notably Staphylococcus species) and some pathogenic fungi (including Candida species) but use declined following reports of animal carcinogenicity. It has also been used for dying wood, silk, and paper, as well as a histological stain.	2.02	1	0	organic chloride salt	anthelminthic drug; antibacterial agent; antifungal agent; antiseptic drug; histological dye
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	1	0	hydrochloride	acid-base indicator; dye; two-colour indicator
octamethylcyclotetrasiloxane octamethylcyclotetrasiloxane: structure. octamethylcyclotetrasiloxane : A cyclosiloxane that is the octamethyl derivative of cyclotetrasiloxane.	2.1	1	0	cyclosiloxane; organosilicon compound
3-hydroxyflavone 3-hydroxyflavone: structure given in first source. flavonol : A monohydroxyflavone that is the 3-hydroxy derivative of flavone.	2.13	1	0	flavonols; monohydroxyflavone
anatabine anatabine: alkaloid found in tobacco; structure	1.96	1	0	bipyridines
alpha-hydroxy-gamma-methylmercaptobutyric acid alpha-hydroxy-gamma-methylmercaptobutyric acid: RN given refers to parent cpd	2.02	1	0	thia fatty acid
ethylmalonic acid ethylmalonic acid: don't confuse with diethyl malonate, which is a diester. ethylmalonate : A dicarboxylic acid anion obtained by deprotonation of at least one of the carboxy groups of ethylmalonic acid.. ethylmalonic acid : A dicarboxylic acid obtained by substitution of one of the methylene hydrogens of malonic acid by an ethyl group.	2.94	4	0	dicarboxylic acid; dicarboxylic fatty acid	human metabolite
1,1'-binaphthyl 1,1'-binaphthyl: structure in first source	7.06	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.	6.99	1	0	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
3-methylglutaric acid [no description available]	2	1	0	alpha,omega-dicarboxylic acid	metabolite
mannoheptulose Mannoheptulose: A 7-carbon keto sugar having the mannose configuration.. D-keto-manno-heptulose : The open chain form of D-manno-heptulose.. D-manno-heptulose : A manno-heptulose with a D-configuration. It has been found in avocados.	1.98	1	0	D-manno-heptulose
diphenyliodonium diphenyliodonium: RN given refers to the parent coumpound; inhibitor of neutrophil superoxide generating oxidase; structure has been determined	2.01	1	0
ethylnitrosourea Ethylnitrosourea: A nitrosourea compound with alkylating, carcinogenic, and mutagenic properties.. N-ethyl-N-nitrosourea : A member of the class of N-nitrosoureas that is urea in which one of the nitrogens is substituted by ethyl and nitroso groups.	1.98	1	0	N-nitrosoureas	alkylating agent; carcinogenic agent; genotoxin; mutagen
acetylenedicarboxylic acid dimethyl ester acetylenedicarboxylic acid dimethyl ester: inhibitor of oxidative phosphorylation	2.15	1	0
cyclopentenone 2-cyclopenten-1-one : An enone that is cyclopentanone having a C=C double bond at position 2.	2.58	2	0	alicyclic ketone; enone	Hsp70 inducer
2-cyclohexen-1-one 2-cyclohexen-1-one: RN given refers to unlabeled cpd with specified locant for double bond. cyclohexenone : The parent compound of the cyclohexenones, composed of cyclohexanone having one double bond in the ring.. cyclohex-2-enone : A cyclohexenone having its C=C double bond at the 2-position.	2.15	1	0	cyclohexenone
nitrosobenzylmethylamine nitrosobenzylmethylamine: structure	1.98	1	0
4-ethyl-1-phospha-2,6,7 trioxabicyclo(2.2.2)octane-1-oxide [no description available]	2.02	1	0
benzyl viologen Benzyl Viologen: 1,1'-Bis(phenylmethyl)4,4'-bipyridinium dichloride. Oxidation-reduction indicator.	2.38	2	0	bipyridines
sodium hydroxide Sodium Hydroxide: A highly caustic substance that is used to neutralize acids and make sodium salts. (From Merck Index, 11th ed)	2.15	1	0	alkali metal hydroxide
zinc oxide Zinc Oxide: A mild astringent and topical protectant with some antiseptic action. It is also used in bandages, pastes, ointments, dental cements, and as a sunblock.	7.01	1	0	zinc molecular entity
vancomycin Vancomycin: Antibacterial obtained from Streptomyces orientalis. It is a glycopeptide related to RISTOCETIN that inhibits bacterial cell wall assembly and is toxic to kidneys and the inner ear.. vancomycin : A complex glycopeptide from Streptomyces orientalis. It inhibits a specific step in the synthesis of the peptidoglycan layer in the Gram-positive bacteria Staphylococcus aureus and Clostridium difficile.	2	1	0	glycopeptide	antibacterial drug; antimicrobial agent; bacterial metabolite
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	3.83	2	1	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
tocopherols [no description available]	3.41	1	1
daminozide daminozide: induces tumors	2.21	1	0	straight-chain fatty acid
paraquat Paraquat: A poisonous dipyridilium compound used as contact herbicide. Contact with concentrated solutions causes irritation of the skin, cracking and shedding of the nails, and delayed healing of cuts and wounds.. paraquat : An organic cation that consists of 4,4'-bipyridine bearing two N-methyl substituents loctated at the 1- and 1'-positions.	2.4	2	0	organic cation	geroprotector; herbicide
heptazine heptazine: structure in first source	7.41	1	0	1,3,5-triazines
2,5-dichloro-4-bromophenol 2,5-dichloro-4-bromophenol: RN given refers to parent cpd	1.97	1	0
methionine sulfoximine methionine sulfoximine : A non-proteinogenic alpha-amino acid that is the sulfoximine derivative of methionine .	1.98	1	0	methionine derivative; non-proteinogenic alpha-amino acid; sulfoximide
2,4-diacetylphloroglucinol 2,4-diacetylphloroglucinol: produced by Pseudomonas aurantiaca. 2,4-diacetylphloroglucinol : A benzenetriol that is phloroglucinol in which two of the ring hydrogens are replaced by acetyl groups.	2.06	1	0	aromatic ketone; benzenetriol; diketone; methyl ketone	antifungal agent; bacterial metabolite
3-chlorocatechol 3-chlorocatechol: inhibits catechol-2,3-dioxygenase. chlorocatechol : Any member of the class of catechols that is catechol substituted by at least one chloro group.. 3-chlorocatechol : A chlorocatechol that is catechol in which the hydrogen adjacent to one of the hydroxy groups is replaced by a chlorine.	1.99	1	0	chlorocatechol; monochlorobenzenes
cladribine [no description available]	4.91	4	0	organochlorine compound; purine 2'-deoxyribonucleoside	antineoplastic agent; immunosuppressive agent
3-phenylbutyric acid 3-phenylbutyric acid : A monocarboxylic acid that is butanoic acid substituted by a phenyl group at position 3.	2	1	0	benzenes; monocarboxylic acid	antibacterial agent; bacterial xenobiotic metabolite
carbenicillin disodium [no description available]	2.03	1	0	organic sodium salt
d-glutamate [no description available]	2.08	1	0	D-alpha-amino acid; glutamic acid	Escherichia coli metabolite; mouse metabolite
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.	4.91	8	1	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.	2.08	1	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	0	chromium group element atom	micronutrient
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.	2.49	2	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.	2.46	2	0	copper group element atom; elemental silver	Escherichia coli metabolite
titanium Titanium: A dark-gray, metallic element of widespread distribution but occurring in small amounts with atomic number, 22, atomic weight, 47.867 and symbol, Ti; specific gravity, 4.5; used for fixation of fractures.	2.46	2	0	titanium group element atom
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.	7.25	1	0	cadmium molecular entity; zinc group element atom
gadolinium Gadolinium: An element of the rare earth family of metals. It has the atomic symbol Gd, atomic number 64, and atomic weight 157.25. Its oxide is used in the control rods of some nuclear reactors.	2.05	1	0	f-block element atom; lanthanoid atom
gold Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.	2	1	0	copper group element atom; elemental gold
sodium nitrate sodium nitrate : The inorganic nitrate salt of sodium.	1.97	1	0	inorganic nitrate salt; inorganic sodium salt	fertilizer; NMR chemical shift reference compound
isopentenyladenosine Isopentenyladenosine: N(6)-[delta(3)-isopentenyl]adenosine. Isopentenyl derivative of adenosine which is a member of the cytokinin family of plant growth regulators.. N(6)-(Delta(2)-isopentenyl)adenosine : A nucleoside analogue in which adenosine has been modified by substitution at the 6-amino nitrogen by a Delta(2)-isopentenyl group.	1.99	1	0	N-ribosyl-N(6)-isopentenyladenine; nucleoside analogue	antineoplastic agent; plant growth regulator; plant metabolite
tricalcium phosphate tricalcium phosphate: a form of tricalcium phosphate used as bioceramic bone replacement material; see also records for alpha-tricalcium phosphate, beta-tricalcium phosphate, calcium phosphate; apatitic tricalcium phosphate Ca9(HPO4)(PO4)5(OH) is the calcium orthophosphate leading to beta tricalcium phosphate Ca3(PO4)2 (b-TCP). calcium phosphate : A calcium salt composed of calcium and phosphate/diphosphate ions; present in milk and used for the mineralisation of calcified tissues.	2.74	3	0	calcium phosphate
chromates Chromates: Salts of chromic acid containing the CrO(2-)4 radical.. chromate(2-) : A chromium oxoanion resulting from the removal of two protons from chromic acid.	2.01	1	0	chromium oxoanion; divalent inorganic anion	oxidising agent
copper sulfate Copper Sulfate: A sulfate salt of copper. It is a potent emetic and is used as an antidote for poisoning by phosphorus. It also can be used to prevent the growth of algae.. copper(II) sulfate : A metal sulfate compound having copper(2+) as the metal ion.	1.96	1	0	metal sulfate	emetic; fertilizer; sensitiser
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	8.35	7	0	dihydrogen
chlorine Chlorine: An element with atomic symbol Cl, atomic number 17, and atomic weight 35, and member of the halogen family.	2	1	0	diatomic chlorine; gas molecular entity	bleaching agent
silver chloride [no description available]	2.08	1	0	inorganic chloride; silver salt
deuterium oxide Deuterium Oxide: The isotopic compound of hydrogen of mass 2 (deuterium) with oxygen. (From Grant & Hackh's Chemical Dictionary, 5th ed) It is used to study mechanisms and rates of chemical or nuclear reactions, as well as biological processes.	2.41	2	0	deuterated compound; water	NMR solvent
galactose aldohexose : A hexose with a (potential) aldehyde group at one end.	2.05	1	0
ozone Ozone: The unstable triatomic form of oxygen, O3. It is a powerful oxidant that is produced for various chemical and industrial uses. Its production is also catalyzed in the ATMOSPHERE by ULTRAVIOLET RAY irradiation of oxygen or other ozone precursors such as VOLATILE ORGANIC COMPOUNDS and NITROGEN OXIDES. About 90% of the ozone in the atmosphere exists in the stratosphere (STRATOSPHERIC OZONE).. ozone : An elemental molecule with formula O3. An explosive, pale blue gas (b.p. -112degreeC) that has a characteristic, pungent odour, it is continuously produced in the upper atmosphere by the action of solar ultraviolet radiation on atmospheric oxygen. It is an antimicrobial agent used in the production of bottled water, as well as in the treatment of meat, poultry and other foodstuffs.	2.02	1	0	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
sodium selenite disodium selenite : An inorganic sodium salt composed of sodium and selenite ions in a 2:1 ratio.	2.07	1	0	inorganic sodium salt; selenite salt	nutraceutical
dimethyl alpha-ketoglutarate [no description available]	2.31	1	0	oxo carboxylic acid
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	2.91	1	0	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
fluorides [no description available]	2.03	1	0	halide anion; monoatomic fluorine
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	4.2	17	0	benzenes; phenyl acetates
butyl acetate butyl acetate: structure. butyl acetate : The acetate ester of butanol.	2.41	1	0	acetate ester	metabolite
triamcinolone Triamcinolone: A glucocorticoid given, as the free alcohol or in esterified form, orally, intramuscularly, by local injection, by inhalation, or applied topically in the management of various disorders in which corticosteroids are indicated. (From Martindale, The Extra Pharmacopoeia, 30th ed, p739). triamcinolone : A C21-steroid hormone that is 1,4-pregnadiene-3,20-dione carrying four hydroxy substituents at positions 11beta, 16alpha, 17alpha and 21 as well as a fluoro substituent at position 9. Used in the form of its 16,17-acetonide to treat various skin infections.	8.48	1	1	11beta-hydroxy steroid; 16alpha-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid hormone; fluorinated steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	anti-allergic agent; anti-inflammatory drug
serum p-component citrate anion : A tricarboxylic acid anion obtained by deprotonation of at least one of the carboxy groups of citric acid.. citrate(3-) : A tricarboxylic acid trianion, obtained by deprotonation of the three carboxy groups of citric acid.	2.05	1	0	citrate anion; tricarboxylic acid trianion	fundamental 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
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	9.07	15	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
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).	1.97	1	0	inorganic sodium salt	antibacterial agent; explosive; mitochondrial respiratory-chain inhibitor; mutagen
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	1.97	1	0	pseudohalide anion	mitochondrial respiratory-chain inhibitor
nigericin Nigericin: A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus. (From Merck Index, 11th ed). nigericin : A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus.	1.97	1	0	polycyclic ether	antibacterial agent; antimicrobial agent; bacterial metabolite; potassium ionophore
2,3,5,6-tetrachlorobiphenyl 2,3,5,6-tetrachlorobiphenyl : A tetrachlorobiphenyl that is biphenyl in which one of the phenyl groups is substituted by chlorines at positions 2, 3, 5, and 6.	2	1	0	tetrachlorobenzene; tetrachlorobiphenyl
ticarcillin Ticarcillin: An antibiotic derived from penicillin similar to CARBENICILLIN in action.. ticarcillin : A penicillin compound having a 6beta-[(2R)-2-carboxy-2-thiophen-3-ylacetyl]amino side-group.	2.03	1	0	penicillin allergen; penicillin	antibacterial drug
pirfenidone pirfenidone : A pyridone that is 2-pyridone substituted at positions 1 and 5 by phenyl and methyl groups respectively. An anti-inflammatory drug used for the treatment of idiopathic pulmonary fibrosis.	7.41	1	0	pyridone	antipyretic; non-narcotic analgesic; non-steroidal anti-inflammatory drug
nicorandil Nicorandil: A derivative of the NIACINAMIDE that is structurally combined with an organic nitrate. It is a potassium-channel opener that causes vasodilatation of arterioles and large coronary arteries. Its nitrate-like properties produce venous vasodilation through stimulation of guanylate cyclase.. nicorandil : A pyrimidinecarboxamide that is nicotinamide in which one of the hydrogens attached to the carboxamide nitrogen is replaced by a 2-(nitrooxy)ethyl group. It has both nitrate-like and ATP-sensitive potassium channel activator properties, and is used for the prevention and treatment of angina pectoris.	2.04	1	0	nitrate ester; pyridinecarboxamide	potassium channel opener; vasodilator agent
bambuterol bambuterol: selective inhibitor of butyrylcholinesterase & acetylcholinesterase. bambuterol : A carbamate ester that is terbutaline in which both of the phenolic hydroxy groups have been protected as the corresponding N,N-dimethylcarbamates. A long acting beta-adrenoceptor agonist used in the treatment of asthma, it is a prodrug for terbutaline.	2.06	1	0	carbamate ester; phenylethanolamines	anti-asthmatic drug; beta-adrenergic agonist; bronchodilator agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; prodrug; sympathomimetic agent; tocolytic agent
itraconazole Itraconazole: A triazole antifungal agent that inhibits cytochrome P-450-dependent enzymes required for ERGOSTEROL synthesis.. itraconazole : An N-arylpiperazine that is cis-ketoconazole in which the imidazol-1-yl group is replaced by a 1,2,4-triazol-1-yl group and in which the actyl group attached to the piperazine moiety is replaced by a p-[(+-)1-sec-butyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]phenyl group. A potent P-glycoprotein and CYP3A4 inhibitor, it is used as an antifungal drug for the treatment of various fungal infections, including aspergillosis, blastomycosis, candidiasis, chromoblastomycosis, coccidioidomycosis, cryptococcosis, histoplasmosis, and sporotrichosis.	2.13	1	0	aromatic ether; conazole antifungal drug; cyclic ketal; dichlorobenzene; dioxolane; N-arylpiperazine; triazole antifungal drug; triazoles	EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor; Hedgehog signaling pathway inhibitor; P450 inhibitor
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	2.41	2	0	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
ferric citrate ferric citrate: RN given refers to Fe(+3)[1:1] salt. iron(III) citrate : An iron chelate resulting from the combination of iron(3+) and citrate(3-).	3.15	5	0	iron chelate	anti-anaemic agent; nutraceutical
d-lactic acid (R)-lactic acid : An optically active form of lactic acid having (R)-configuration.	2.08	1	0	2-hydroxypropanoic acid	Escherichia coli metabolite; human metabolite
cuprous chloride cuprous chloride: RN given refers to unlabeled cpd. copper(I) chloride : An inorganic chloride of copper in which the metal is in the +1 oxidation state.	6.92	1	0	copper molecular entity; inorganic chloride	agrochemical; molluscicide
n-acetylaspartic acid N-acetyl-L-aspartic acid : An N-acyl-L-aspartic acid in which the acyl group is specified as acetyl.	2.03	1	0	N-acetyl-L-amino acid; N-acyl-L-aspartic acid	antioxidant; human metabolite; mouse metabolite; nutraceutical; rat metabolite
glucose-1-phosphate glucose-1-phosphate: RN given refers to (alpha-D-Glc)-isomer. alpha-D-glucose 1-phosphate : A D-glucopyranose 1-phosphate in which the anomeric centre has alpha-configuration.	2.25	1	0	D-glucopyranose 1-phosphate
cephalosporin c cephalosporin C: RN given refers to parent cpd; structure in Merck, 9th ed, #1937. cephalosporin C : A cephalosporin antibiotic carrying a 3-acetoxymethyl substituent and a 6-oxo-N(6)-L-lysino group at position 7.	3.48	1	1	cephalosporin	fungal metabolite
estradiol 3,17-disulfate estradiol 3,17-disulfate: RN given refers to (17beta)-isomer	2.03	1	0	steroid sulfate
anthraquinone-2,6-disulfonate anthraquinone-2,6-disulfonate: structure in first source. anthraquinone-2,6-disulfonic acid : A member of the class of anthraquinones that is 9,10-anthraquinone substituted at positions 2 and 6 by sulfo groups.	2.02	1	0	anthraquinone; arenesulfonic acid
salicylhydroxamic acid [no description available]	1.97	1	0	hydroxamic acid; phenols	antibacterial drug; EC 1.11.2.2 (myeloperoxidase) inhibitor; EC 3.5.1.5 (urease) inhibitor; trypanocidal drug
1,7-phenanthroline [no description available]	1.97	1	0	phenanthroline
1h-imidazo(4,5-b)pyridine 1H-imidazo(4,5-b)pyridine: structure given in first source. 4-azabenzimidazole : The [4,5-b]-fused isomer of imidazopyridine.	2.21	1	0	imidazopyridine
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.	3.99	1	1	1,2,3-triazole
duroquinone tetramethyl-1,4-benzoquinone: structure in first source. duroquinone : A member of the class of 1,4-benzoquinones that is 1,4-benzoquinone in which all four hydrogens are substituted by methyl groups.	2	1	0	1,4-benzoquinones
2-butynoic acid [no description available]	2.15	1	0
ubiquinone-o 2,3-dimethoxy-5-methyl-p-benzoquinone: from solid-cultured Antrodia camphorata; structure in first source. ubiquinone-0 : A derivative of benzoquinone carrying a 5-methyl substituent; and methoxy substituents at positions 2 and 3. The core structure of the ubiquinone group of compounds.	2	1	0	ubiquinones	Escherichia coli metabolite; human metabolite
beta-hydroxyisovaleric acid 3-hydroxyisovaleric acid : A 3-hydroxy monocarboxylic acid that is isovaleric acid substituted at position 3 by a hydroxy group. Used as indicator of biotin deficiency.	2	1	0	3-hydroxy monocarboxylic acid	human metabolite
phenylpropiolic acid phenylpropiolic acid: structure. phenylpropiolic acid : An acetylenic compound that is propynoic acid in which the acetylenic hydrogen is replaced by a phenyl group.	2.15	1	0	acetylenic compound; alpha,beta-unsaturated monocarboxylic acid; benzenes
morpholinopropane sulfonic acid 3-(N-morpholino)propanesulfonic acid : A Good's buffer substance, pKa = 7.2 at 20 degreeC.	1.99	1	0	MOPS; morpholines; organosulfonic acid
trichlorofluoroethene [no description available]	2.02	1	0
tocophersolan tocophersolan: RN given refers to parent cpd	2.05	1	0	tocol
bathophenanthroline 4,7-diphenyl-1,10-phenanthroline : A member of the class of phenanthrolines that is 1,10-phenanthroline bearing two phenyl substituents at positions 4 and 7.	1.97	1	0	benzenes; phenanthrolines	chelator
6-hydroxynicotinic acid 6-hydroxynicotinic acid : A monohydroxypyridine that is the 6-hydroxy derivative of nicotinic acid.	1.96	1	0	monohydroxypyridine	Arabidopsis thaliana metabolite; human urinary metabolite; mouse metabolite
ethyl protocatechuate ethyl protocatechuate: structure. ethyl 3,4-dihydroxybenzoate : An ethyl ester resulting from the formal condensation of the carboxy group of 3,4-dihydroxybenzoic acid with ethanol. It is the anti-oxidative component of peanut seed testa.	2.08	1	0	catechols; ethyl ester	antibacterial agent; antioxidant; apoptosis inducer; EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor; plant metabolite
ethyl 2-butynoate [no description available]	2.15	1	0
4-(hydroxyphenyl)acetamide 4-(hydroxyphenyl)acetamide: structure given in first source; an impurity found in the HPLC assay for atenolol; do not confuse with acetaminophen	2.05	1	0	acetamides
coenzyme a [no description available]	2.46	2	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.	2.42	2	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
6-phosphogluconic acid gluconic acid-6-phosphate: structure. 6-phospho-D-gluconate : A monocarboxylic acid anion resulting from the removal of a proton from the carboxy group of 6-phospho-D-gluconic acid.. 6-phospho-D-gluconic acid : A gluconic acid phosphate having the phosphate group at the 6-position. It is an intermediate in the pentose phosphate pathway.	2.05	1	0	gluconic acid phosphate	fundamental metabolite
ethylphenylpropiolate ethylphenylpropiolate: structure	2.15	1	0
methylglucoside [no description available]	2.37	2	0
maleopimaric acid maleopimaric acid: RN given refers to (4 alpha,8 alpha,12 alpha,13R,14R)-isomer	2.03	1	0
3-hydroxybutyric acid (R)-3-hydroxybutyric acid : The R-enantiomer of 3-hydroxybutyric acid. Involved in the synthesis and degradation of ketone bodies, it can be used as an energy source by the brain during hypoglycaemia, and for the synthesis of biodegradable plastics. It is a sex pheremone in the European spider Linyphia triangularis.	2.03	1	0	3-hydroxybutyric acid; ketone body	fungal metabolite; human metabolite; pheromone
arabitol arabitol: RN given refers to cpd without isomeric designation. arabinitol : A pentitol that is the sugar alcohol produced by the reduction of arabinose or lyxose. It is found in serum or urine of human infected with Candida albicans.. D-arabinitol : The D-enantiomer of arabinitol.	2.05	1	0	arabinitol
(S)-3-hydroxybutyric acid (S)-3-hydroxybutyric acid : The S-enantiomer of 3-hydroxybutyric acid; a normal human metabolite, that has been found elevated in geriatric patients remitting from depression.	2.03	1	0	3-hydroxybutyric acid
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	1	0	D-glucuronic acid	algal metabolite
2-phenylsuccinate [no description available]	2.38	2	0
N-Acetyl-DL-aspartic acid [no description available]	2.03	1	0	aspartic acid derivative
n-acetyldehydroalanine methyl ester N-acetyldehydroalanine methyl ester: modifies amino & sulfhydryl groups in amino acids & proteins; structure	2.31	1	0
2-hydroxyisovaleric acid 2-hydroxyisovaleric acid: RN given refers to parent cpd without isomeric designation. 2-hydroxy-3-methylbutyric acid : A valine derivative that is valine in which the amino group has been replaced by a hydroxy group.	2.03	1	0	2-hydroxy monocarboxylic acid	human metabolite
n-succinimidyl 3-(2-pyridyldithio)propionate N-succinimidyl 3-(2-pyridyldithio)propionate: heterobifunctional reagent	2	1	0
cobalt Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.	2.13	1	0	cobalt group element atom; metal allergen	micronutrient
eudragit rs Eudragit RS: copolymer of acrylic & methacrylic acid esters & quaternary ammonium groups; used for microcapsules	2.01	1	0
fingolimod hydrochloride Fingolimod Hydrochloride: A sphingosine-derivative and IMMUNOSUPPRESSIVE AGENT that blocks the migration and homing of LYMPHOCYTES to the CENTRAL NERVOUS SYSTEM through its action on SPHINGOSINE 1-PHOSPHATE RECEPTORS. It is used in the treatment of MULTIPLE SCLEROSIS.. fingolimod hydrochloride : The hydrochloride salt of 2-amino-2-[2-(4-octylphenyl) ethyl]-1,3-propanediol (fingolimod).	4.91	4	0	hydrochloride	immunosuppressive agent; prodrug; sphingosine-1-phosphate receptor agonist
triptolide [no description available]	3.16	1	0	diterpenoid; epoxide; gamma-lactam; organic heteroheptacyclic compound	antispermatogenic agent; plant metabolite
deoxyglucose Deoxyglucose: 2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.. deoxyglucose : A deoxyhexose comprising glucose having at least one hydroxy group replaced by hydrogen.	7.69	3	0
valerates Valerates: Derivatives of valeric acid, including its salts and esters.	2	1	0	short-chain fatty acid anion; straight-chain saturated fatty acid anion	plant metabolite
3-chloro-4-hydroxyphenylacetic acid 3-chloro-4-hydroxyphenylacetic acid: RN given refers to parent cpd. (3-chloro-4-hydroxyphenyl)acetic acid : A hydroxy monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by a 3-chloro-4-hydroxyphenyl group. It is a major chlorinated metabolite of chlorotyrosine.	2.05	1	0	hydroxy monocarboxylic acid; monochlorobenzenes; phenols	mammalian metabolite
3-mercaptopicolinic acid 3-mercaptopicolinic acid: gluconeogenesis inhibitor; may also inhibit ATP-dependentphosphoenolpyruvate carboxykinase	1.96	1	0
matairesinol matairesinol: lignan that is a central precursor in plants in the biosynthesis of numerous lignans (coordinate with specific); RN refers to (3R-trans)-isomer. (-)-matairesinol : A lignan that is gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer).	2.03	1	0	gamma-lactone; lignan; polyphenol	angiogenesis inhibitor; anti-asthmatic agent; phytoestrogen; plant metabolite
caprylates Caprylates: Derivatives of caprylic acid. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain a carboxy terminated eight carbon aliphatic structure.. octanoate : A straight-chain saturated fatty acid anion that is the conjugate base of octanoic acid (caprylic acid); believed to block adipogenesis.	2.4	2	0	fatty acid anion 8:0; straight-chain saturated fatty acid anion	human metabolite; Saccharomyces cerevisiae metabolite
hydroxypropylmethylcellulose acetate succinate hydroxypropylmethylcellulose acetate succinate: structure given in first source	2.01	1	0
benzoyl-coenzyme a benzoyl-coenzyme A: RN given refers to unlabeled cpd	1.99	1	0
hydroxycitric acid hydroxycitric acid: RN given refers to cpd without isomeric designation; structure	2.31	1	0	carbonyl compound
desloratadine desloratadine: major metabolite of loratadine. desloratadine : Loratadine in which the ethoxycarbonyl group attached to the piperidine ring is replaced by hydrogen. The major metabolite of loratidine, desloratadine is an antihistamine which is used for the symptomatic relief of allergic conditions including rhinitis and chronic urticaria. It does not readily enter the central nervous system, so does not cause drowsiness.	2.02	1	0	benzocycloheptapyridine	anti-allergic agent; cholinergic antagonist; drug metabolite; H1-receptor antagonist
methotrexate [no description available]	9.28	5	0	dicarboxylic acid; monocarboxylic acid amide; pteridines	abortifacient; antimetabolite; antineoplastic agent; antirheumatic drug; dermatologic drug; DNA synthesis inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; immunosuppressive agent
xylose xylopyranose: structure in first source	3.71	9	0	D-xylose
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.	2.4	2	0	amino acid zwitterion; glutamine family amino acid; L-alpha-amino acid; proline; proteinogenic amino acid	algal metabolite; compatible osmolytes; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
betamethasone-17,21-dipropionate betamethasone-17,21-dipropionate: may also contain chlorocresol (UD 25:22R)	2.21	1	0
saicar SAICAR: adenosylsuccinase catalyzes its conversion to AICAR. SAICAR : A 1-(phosphoribosyl)imidazolecarboxamide resulting from the formal condesation of the darboxy group of 5-amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid with the amino group of L-aspartic acid.	1.97	1	0	1-(phosphoribosyl)imidazolecarboxamide	Escherichia coli metabolite; mouse metabolite
2-methylthio-n-6-isopentenyladenosine 2-methylthio-N(6)-(Delta(2)-isopentenyl)adenosine : A nucleoside analogue in which adenosine has been modified by substitution at C-2 by a methylthio (methylsulfanyl) group and at the 6-amino nitrogen by a Delta(2)-isopentenyl group.	1.99	1	0	nucleoside analogue
sedoheptulose 7-phosphate sedoheptulose 7-phosphate : A ketoheptose phosphate consisting of sedoheptulose having a phosphate group at the 7-position. It is an intermediate metabolite in the pentose phosphate pathway.	2.48	2	0	ketoheptose phosphate; sedoheptulose derivative	Escherichia coli metabolite; human metabolite; mouse metabolite
3,4-dihydroxybenzophenone 3,4-dihydroxybenzophenone: structure in first source	2.08	1	0
biotin vitamin B7 : Any member of a group of vitamers that belong to the chemical structural class called biotins that exhibit biological activity against vitamin B7 deficiency. Vitamin B7 deficiency is very rare in individuals who take a normal balanced diet. Foods rich in biotin are egg yolk, liver, cereals, vegetables (spinach, mushrooms) and rice. Symptoms associated with vitamin B7 deficiency include thinning hair, scaly skin rashes around eyes, nose and mouth, and brittle nails. The vitamers include biotin and its ionized and salt forms.	2.08	1	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.	4.47	6	0
erlotinib hydrochloride [no description available]	2.05	1	0	hydrochloride; terminal acetylenic compound	antineoplastic agent; protein kinase inhibitor
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	1.99	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.	6.96	1	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
anabasine Anabasine: A piperidine botanical insecticide.. (S)-anabasine : The (S)-enantiomer of anabasine.. anabasine : A pyridine alkaloid that is pyridine substituted by a piperidin-2-yl group at position 3.	1.96	1	0	anabasine
n-phenylacrylamide N-phenylacrylamide: structure in first source	2.21	1	0
sitosterol, (3beta)-isomer Sobatum: tradename; active fraction of Solanum trilobatum; reduces side-effects of radiation-induced toxicity. sitosterol : A member of the class of phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3.	2.21	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; C29-steroid; phytosterols; stigmastane sterol	anticholesteremic drug; antioxidant; mouse metabolite; plant metabolite; sterol methyltransferase inhibitor
erythritol [no description available]	2.01	1	0	butane-1,2,3,4-tetrol	antioxidant; human metabolite; plant metabolite
glycogen glycogen : A polydisperse, highly branched glucan composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage, joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some cumulative alpha(1->6) links also may occur. The branches in glycogen typically contain 8 to 12 glucose residues.	2.35	2	0
ribulose 5-phosphate ribulose 5-phosphate: RN given refers to cpd without isomeric designation. D-ribulose 5-phosphate : The D-enantiomer of ribulose 5-phosphate that is one of the end-products of the pentose phosphate pathway.. ribulose 5-phosphate : A ribulose phosphate in which the phosphate group is attached at position 5.	2.48	2	0	ribulose 5-phosphate	mouse metabolite
arabinose [no description available]	1.99	1	0	L-arabinose	Escherichia coli metabolite; mouse metabolite
hexacyanoferrate iii hexacyanoferrate III: RN given refers to parent cpd	1.97	1	0
d-2-hydroxyglutarate (R)-2-hydroxyglutaric acid : The (R)-enantiomer of 2-hydroxyglutaric acid.	2.86	3	0	2-hydroxyglutaric acid	algal metabolite
casein hydrolysate casein hydrolysate: an ingredient of trypticase soy broth; casitone is a tryptic digest of casein	1.94	1	0
tartaric acid tartaric acid: RN given refers to cpd with unspecified isomeric designation. D-tartaric acid : The D-enantiomer of tartaric acid.	4.09	15	0	tartaric acid	Escherichia coli metabolite
alpha-hydroxyglutarate, (l)-isomer [no description available]	2.86	3	0	2-hydroxyglutaric acid
monensin Monensin: An antiprotozoal agent produced by Streptomyces cinnamonensis. It exerts its effect during the development of first-generation trophozoites into first-generation schizonts within the intestinal epithelial cells. It does not interfere with hosts' development of acquired immunity to the majority of coccidial species. Monensin is a sodium and proton selective ionophore and is widely used as such in biochemical studies.. monensin A : A spiroketal, monensin A is the major component of monensin, a mixture of antibiotic substances produced by Streptomyces cinnamonensis. An antiprotozoal, it is used as the sodium salt as a feed additive for the prevention of coccidiosis in poultry and as a growth promoter in cattle.	8.4	1	1	cyclic hemiketal; monocarboxylic acid; polyether antibiotic; spiroketal	antifungal agent; coccidiostat; ionophore
ochratoxin a ochratoxin A: structure in first source & in Merck, 9th ed, #6549. ochratoxin A : A phenylalanine derivative resulting from the formal condensation of the amino group of L-phenylalanine with the carboxy group of (3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid (ochratoxin alpha). It is among the most widely occurring food-contaminating mycotoxins, produced by Aspergillus ochraceus, Aspergillus carbonarius and Penicillium verrucosum.	2.03	1	0	isochromanes; monocarboxylic acid amide; N-acyl-L-phenylalanine; organochlorine compound; phenylalanine derivative	Aspergillus metabolite; calcium channel blocker; carcinogenic agent; mycotoxin; nephrotoxin; Penicillium metabolite; teratogenic agent
lignans Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	2.03	1	0
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2.45	2	0	cyclodextrin
aconitic acid trans-aconitic acid : The trans-isomer of aconitic acid.	2.15	1	0	aconitic acid	fundamental metabolite
maleic acid maleic acid: RN given refers to parent cpd(Z)-isomer which is maleic acid; all RR's given refer to (Z)-isomer; (E)-isomer is fumaric acid. maleic acid : A butenedioic acid in which the double bond has cis- (Z)-configuration.	6.63	39	0	butenedioic acid	algal metabolite; mouse metabolite; plant metabolite
acetyl coenzyme a Acetyl Coenzyme A: Acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.	2.42	2	0	acyl-CoA	acyl donor; coenzyme; effector; fundamental metabolite
e-z cinnamic acid cinnamic acid : A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.. trans-cinnamic acid : The E (trans) isomer of cinnamic acid	3.02	4	0	cinnamic acid	plant metabolite
trichostatin a trichostatin A: chelates zinc ion in the active site of histone deacetylases, resulting in preventing histone unpacking so DNA is less available for transcription; do not confuse with TRICHOSANTHIN which is a protein; found in STREPTOMYCES	2.04	1	0	antibiotic antifungal agent; hydroxamic acid; trichostatin	bacterial metabolite; EC 3.5.1.98 (histone deacetylase) inhibitor; geroprotector
retinol Vitamin A: Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of CAROTENOIDS found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.. vitamin A : Any member of a group of fat-soluble retinoids produced via metabolism of provitamin A carotenoids that exhibit biological activity against vitamin A deficiency. Vitamin A is involved in immune function, vision, reproduction, and cellular communication.. all-trans-retinol : A retinol in which all four exocyclic double bonds have E- (trans-) geometry.. retinol : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraen-1-ol substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).	1.93	1	0	retinol; vitamin A	human metabolite; mouse metabolite; plant metabolite
tacrolimus Tacrolimus: A macrolide isolated from the culture broth of a strain of Streptomyces tsukubaensis that has strong immunosuppressive activity in vivo and prevents the activation of T-lymphocytes in response to antigenic or mitogenic stimulation in vitro.. tacrolimus (anhydrous) : A macrolide lactam containing a 23-membered lactone ring, originally isolated from the fermentation broth of a Japanese soil sample that contained the bacteria Streptomyces tsukubaensis.	3.12	1	0	macrolide lactam	bacterial metabolite; immunosuppressive agent
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	2.51	2	0	ferulic acids	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; MALDI matrix material; plant metabolite
pectins Pectins: High molecular weight polysaccharides present in the cell walls of all plants. Pectins cement cell walls together. They are used as emulsifiers and stabilizers in the food industry. They have been tried for a variety of therapeutic uses including as antidiarrheals, where they are now generally considered ineffective, and in the treatment of hypercholesterolemia.. alpha-D-galacturonic acid : The alpha-anomer of D-galacturonic acid.	2.02	1	0	D-galactopyranuronic acid
fumaramide [no description available]	2.4	2	0
fosfomycin Fosfomycin: An antibiotic produced by Streptomyces fradiae.. fosfomycin : A phosphonic acid having an (R,S)-1,2-epoxypropyl group attached to phosphorus.	3.46	1	1	epoxide; phosphonic acids	antimicrobial agent; EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor
adenylosuccinate aspartyl adenylate: RN given refers to (L)-isomer	1.97	1	0
stigmatellin stigmatellin: isolated from myxobacterium Stigmatella aurantiaca; structure in first source. stigmatellin A : A member of the class of chromones that is isolated from Stigmatella aurantiaca Sg a15.	2.01	1	0	aromatic ether; chromones; olefinic compound; phenols	bacterial metabolite; quinol oxidation site inhibitor
5-carboxy-8-hydroxyquinoline 5-carboxy-8-hydroxyquinoline: a JmjC histone demethylase inhibitor; structure in first source	2.8	3	0	quinolines
tenofovir tenofovir (anhydrous) : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens is replaced by a [(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(isopropyloxycarbonyloxymethyl) ester (disoproxil ester) prodrug is used as the fumaric acid salt in combination therapy for the treatment of HIV infection.	8.53	1	1	nucleoside analogue; phosphonic acids	antiviral drug; drug metabolite; HIV-1 reverse transcriptase inhibitor
bx 471 BX 471: a CC chemokine receptor-1 antagonist; structure in first source	2.02	1	0
sodium bicarbonate Sodium Bicarbonate: A white, crystalline powder that is commonly used as a pH buffering agent, an electrolyte replenisher, systemic alkalizer and in topical cleansing solutions.	9.47	5	1	one-carbon compound; organic sodium salt	antacid; food anticaking agent
sodium benzoate Sodium Benzoate: The sodium salt of BENZOIC ACID. It is used as an antifungal preservative in pharmaceutical preparations and foods. It may also be used as a test for liver function.. sodium benzoate : An organic sodium salt resulting from the replacement of the proton from the carboxy group of benzoic acid by a sodium ion.	7.81	3	0	organic sodium salt	algal metabolite; antimicrobial food preservative; drug allergen; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; human xenobiotic metabolite; plant metabolite
potassium fluoride potassium fluoride : A fluoride salt having K+ as the counterion.	2.03	1	0	fluoride salt; potassium salt	NMR chemical shift reference compound; poison
dimethyloxalylglycine dimethyloxallyl glycine: structure in first source	2.31	1	0	glycine derivative; methyl ester; secondary carboxamide	EC 1.14.11.29 (hypoxia-inducible factor-proline dioxygenase) inhibitor; neuroprotective agent
crotonic acid crotonic acid: a stereospecific unsaturated carboxylic acid found in CROTON OIL. butenoic acid : Any C4, straight-chain fatty acid containing one double bond.. crotonic acid : A but-2-enoic acid with a trans- double bond at C-2. It has been isolated from Daucus carota.	2.06	1	0	2-butenoic acid	plant metabolite
cinnamaldehyde 3-phenylprop-2-enal : A member of the class of cinnamaldehydes that is prop-2-enal in which a hydrogen at position 3 has been replaced by a phenyl group. The configuration of the double bond is not specified; the name "cinnamaldehyde" is widely used to refer to the E (trans) isomer.. (E)-cinnamaldehyde : The E (trans) stereoisomer of cinnamaldehyde, the parent of the class of cinnamaldehydes.	7.52	2	0	3-phenylprop-2-enal; cinnamaldehydes	antifungal agent; EC 4.3.1.24 (phenylalanine ammonia-lyase) inhibitor; flavouring agent; hypoglycemic agent; plant metabolite; sensitiser; vasodilator agent
2-hydroxycinnamic acid trans-2-coumaric acid : The trans-isomer of 2-coumaric acid.. 2-coumaric acid : A monohydroxycinnamic acid in which the hydroxy substituent is located at C-2 of the phenyl ring.	2.06	1	0	2-coumaric acid; phenols	antioxidant; metabolite
3-coumaric acid 3-coumaric acid: RN given refers to cpd without isomeric designation in Chemline. trans-3-coumaric acid : A 3-coumaric acid that is phenol substituted with trans-2-propenoic acid at position C-3.. 3-coumaric acid : A monohydroxycinnamic acid in which the hydroxy substituent is located at C-3 of the phenyl ring.	2.06	1	0	3-coumaric acid
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.	2.76	3	0	4-coumaric acid	food component; mouse metabolite; plant metabolite
dimethyl fumarate [no description available]	8.44	14	1	diester; enoate ester; methyl ester	antipsoriatic; immunomodulator
ethyl cinnamate ethyl cinnamate: a pine weevil antifeedant; structure in first source	2.15	1	0	alkyl cinnamate; ethyl ester
4-chlorocinnamic acid 4-chlorocinnamic acid : An organochlorine compound comprising trans-cinnamic acid having a chloro substituent at the 4-position on the phenyl ring.	2.06	1	0	monochlorobenzenes
diethyl fumarate diethyl fumarate : A dieter obtained by the formal condensation of fumaric acid with ethanol.	2.69	3	0	diester	metabolite
Methylenedioxycinnamic acid [no description available]	2.06	1	0	hydroxycinnamic acid
furanacrylic acid [no description available]	2.06	1	0
sorbic acid Sorbic Acid: Mold and yeast inhibitor. Used as a fungistatic agent for foods, especially cheeses.. (2E,4E)-hexa-2,4-dienoic acid : A sorbic acid having trans-double bonds at positions 2 and 4; a food preservative that can induce cutaneous vasodilation and stinging upon topical application to humans. It is the most thermodynamically stable of the four possible geometric isomers possible, as well as the one with the highest antimicrobial activity.. sorbic acid : A hexadienoic acid with double bonds at C-2 and C-4; it has four geometrical isomers, of which the trans,trans-form is naturally occurring.	3.15	5	0	alpha,beta-unsaturated monocarboxylic acid; sorbic acid
aconitic acid cis-aconitic acid : The cis-isomer of aconitic acid.	2.53	2	0	aconitic acid	fundamental metabolite
citraconic acid citraconic acid: was MH 1975-92 (see under MALEATES 1975-90); METHYLMALEIC ACID was see CITRACONIC ACID 1975-92; use MALEATES to search CITRACONIC ACID 1975-92; RN refers to (Z)-isomer; SO refers to (E)-isomer. citraconic acid : A dicarboxylic acid consisting of maleic acid having a methyl substituent at the 2-position.	3.06	5	0	dicarboxylic acid; dicarboxylic fatty acid	human metabolite
flavin-adenine dinucleotide Flavin-Adenine Dinucleotide: A condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972)	3.37	7	0	flavin adenine dinucleotide; vitamin B2	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; prosthetic group
sodium metabisulfite sodium metabisulfite: request from searcher; RN given refers to disulfurous acid, di-Na salt. sodium disulfite : An inorganic sodium salt composed of sodium and disulfite ions in a 2:1 ratio.	2.05	1	0	inorganic sodium salt	food antioxidant
sesquiterpenes [no description available]	1.92	1	0
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	2.48	2	0	caffeic acid	geroprotector; mouse metabolite
3-(4-methylbenzoyl)acrylic acid [no description available]	2.15	1	0	carbonyl compound
4-methoxycinnamic acid [no description available]	2.06	1	0	cinnamic acids
thiohydantoins Thiohydantoins: Sulfur analogs of hydantoins with one or both carbonyl groups replaced by thiocarbonyl groups.	2.1	1	0
3-methylglutaconic acid (E)-3-methylglutaconic acid : A dicarboxylic acid comprising (E)-glutaconic acid carrying a 3-methyl substituent.	2	1	0	dicarboxylic acid
chlorogenic acid caffeoylquinic acid: Antiviral Agent; structure in first source. chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3.	2.13	1	0	cinnamate ester; tannin	food component; plant metabolite
D-fructopyranose [no description available]	2.75	3	0	cyclic hemiketal; D-fructose; fructopyranose	sweetening agent
thioacetamide Thioacetamide: A crystalline compound used as a laboratory reagent in place of HYDROGEN SULFIDE. It is a potent hepatocarcinogen.. thioacetamide : A thiocarboxamide consiting of acetamide having the oxygen replaced by sulfur.	2.37	2	0	thiocarboxamide	hepatotoxic agent
1-butyl-3-methylimidazolium chloride 1-butyl-3-methylimidazolium chloride: structure in first source	7.17	1	0
nadp [no description available]	3.27	6	0
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	2.52	2	0
erythronic acid erythronic acid : The erythro-isomer of 2,3,4-trihydroxybutanoic acid.. D-erythronic acid : An erythronic acid in which the stereocentres at positions 2 and 3 both have R-configuration (the D-enantiomer).. erythronate : A hydroxy monocarboxylic acid anion obtained by deprotonation of the carboxy group of any erythronic acid; major species at pH 7.3.	2.05	1	0	erythronic acid
uc-781 [no description available]	2.05	1	0
estrone sulfate estrone sulfate: sulfoconjugated estrone; RN given refers to parent cpd	2.03	1	0	17-oxo steroid; steroid sulfate	human metabolite; mouse metabolite
cystine [no description available]	2.02	1	0
fospropofol [no description available]	2.05	1	0	alkylbenzene
oxalylglycine oxalylglycine: structure given in first source. N-oxalylglycine : An amino dicarboxylic acid that is iminodiacetic acid with an oxo substituent. It is used as an inhibitor of alpha-ketoglutarate dependent (EC 1.14.11.*) enzymes.	3.35	6	0	amino dicarboxylic acid; N-acylglycine	EC 1.14.11.* (oxidoreductase acting on paired donors, 2-oxoglutarate as one donor, incorporating 1 atom each of oxygen into both donors) inhibitor
phosphothreonine Phosphothreonine: The phosphoric acid ester of threonine. Used as an identifier in the analysis of peptides, proteins, and enzymes.. O-phospho-L-threonine : A L-threonine derivative phosphorylated at the side-chain hydroxy function.	1.97	1	0	L-threonine derivative; non-proteinogenic L-alpha-amino acid; O-phosphoamino acid	Escherichia coli metabolite
alpha-chymotrypsin Chymotrypsin: A serine endopeptidase secreted by the pancreas as its zymogen, CHYMOTRYPSINOGEN and carried in the pancreatic juice to the duodenum where it is activated by TRYPSIN. It selectively cleaves aromatic amino acids on the carboxyl side.	1.96	1	0
osteoprotegerin Osteoprotegerin: A secreted member of the TNF receptor superfamily that negatively regulates osteoclastogenesis. It is a soluble decoy receptor of RANK LIGAND that inhibits both CELL DIFFERENTIATION and function of OSTEOCLASTS by inhibiting the interaction between RANK LIGAND and RECEPTOR ACTIVATOR OF NUCLEAR FACTOR-KAPPA B.	2.01	1	0	long-chain fatty acid
dimethyl maleate dimethyl maleate: structure. dimethyl maleate : A maleate ester resulting from the formal condensation of both carboxy groups of maleic acid with methanol. It is commonly used as a dienophile for Diels-Alder-type cycloaddition reactions in organic synthesis.	2.15	1	0	diester; maleate ester; methyl ester
sphingosine sphing-4-enine : A sphingenine in which the C=C double bond is located at the 4-position.. sphingenine : A 2-aminooctadecene-1,3-diol having (2S,3R)-configuration.. sphingoid : Sphinganine, its homologs and stereoisomers, and the hydroxy and unsaturated derivatives of these compounds.. 2-aminooctadec-4-ene-1,3-diol : A 2-aminooctadecene-1,3-diol having its double bond at position 4.	4.91	4	0	sphing-4-enine	human metabolite; mouse metabolite
quercetin [no description available]	7.74	3	0	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger
bilirubin [no description available]	2.06	1	0	biladienes; dicarboxylic acid	antioxidant; human metabolite; mouse metabolite
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	2.03	1	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
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.	2.11	1	0	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
calcitriol dihydroxy-vitamin D3: as a major in vitro metabolite of 1alpha,25-dihydroxyvitamin D3, produced in primary cultures of neonatal human keratinocytes	2.21	1	0	D3 vitamins; hydroxycalciol; triol	antineoplastic agent; antipsoriatic; bone density conservation agent; calcium channel agonist; calcium channel modulator; hormone; human metabolite; immunomodulator; metabolite; mouse metabolite; nutraceutical
vitamin k semiquinone radical vitamin K semiquinone radical: found in active preparations of vitamin K-dependent carboxylase. vitamin K : Any member of a group of fat-soluble 2-methyl-1,4-napthoquinones that exhibit biological activity against vitamin K deficiency. Vitamin K is required for the synthesis of prothrombin and certain other blood coagulation factors.	2.88	4	0
beta carotene beta Carotene: A carotenoid that is a precursor of VITAMIN A. Beta carotene is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (PORPHYRIA, ERYTHROPOIETIC).. provitamin A : A provitamin that can be converted into vitamin A by enzymes from animal tissues.	1.99	1	0	carotenoid beta-end derivative; cyclic carotene	antioxidant; biological pigment; cofactor; ferroptosis inhibitor; human metabolite; mouse metabolite; plant metabolite; provitamin A
11-cis-retinal Rhodopsin: A purplish-red, light-sensitive pigment found in RETINAL ROD CELLS of most vertebrates. It is a complex consisting of a molecule of ROD OPSIN and a molecule of 11-cis retinal (RETINALDEHYDE). Rhodopsin exhibits peak absorption wavelength at about 500 nm.. 11-cis-retinal : A retinal having 2E,4Z,6E,8E-double bond geometry.	1.98	1	0	retinal	chromophore; human metabolite; mouse metabolite
glutaconic acid glutaconic acid: RN given refers to parent cpd without isomeric designation; structure. glutaconic acid : A pentenedioic acid that is pent-2-ene substituted by carboxy groups at positions 1 and 5.. (E)-glutaconic acid : The (E)-isomer of glutaconic acid.	2.43	2	0	glutaconic acid
rosin rosin: Resin from plant. Do not confuse with the specific compound: 3-phenyl-2-propenyl-(E)-beta-D-glucopyranoside, also know as rosin.	2.03	1	0
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	1	0	D3 vitamins; hydroxy seco-steroid; seco-cholestane; secondary alcohol; steroid hormone	geroprotector; human metabolite
montelukast montelukast: a leukotriene D4 receptor antagonist	2.13	1	0	aliphatic sulfide; monocarboxylic acid; quinolines	anti-arrhythmia drug; anti-asthmatic drug; leukotriene antagonist
astaxanthine astaxanthine: a keto form of carotene; pigment in flesh of Scottish salmon (Salmo salar) crustacoa-lobster (Homarus gammarus, flamingo feathers; structure; a carotenoid without vitamin A activity, has shown anti-oxidant and anti-inflammatory activities. astaxanthin : A carotenone that consists of beta,beta-carotene-4,4'-dione bearing two hydroxy substituents at positions 3 and 3' (the 3S,3'S diastereomer). A carotenoid pigment found mainly in animals (crustaceans, echinoderms) but also occurring in plants. It can occur free (as a red pigment), as an ester, or as a blue, brown or green chromoprotein.	2.31	1	0	carotenol; carotenone	animal metabolite; anticoagulant; antioxidant; food colouring; plant metabolite
santin santin: from Tanacetum microphyllum; structure given in first source. santin : A trimethoxyflavone that is flavone substituted by methoxy groups at positions 3, 6 and 4' and hydroxy groups at positions 5 and 7 respectively.	2.21	1	0	dihydroxyflavone; trimethoxyflavone	plant metabolite
astragalin kaempferol-3-O-glucoside: isolated from the pit of Mahkota dewa; structure in first source. kaempferol 3-O-beta-D-glucoside : A kaempferol O-glucoside in which a glucosyl residue is attached at position 3 of kaempferol via a beta-glycosidic linkage.	2.21	1	0	beta-D-glucoside; kaempferol O-glucoside; monosaccharide derivative; trihydroxyflavone	plant metabolite; trypanocidal drug
etretinate retinoid : Oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.	3.1	1	0	enoate ester; ethyl ester; retinoid	keratolytic drug
menaquinone 6 menaquinone 6: RN given refers to (all-E)-isomer	2.42	2	0
beta-nitrostyrene beta-nitrostyrene: RN given refers to cpd without isomeric designation	2.21	1	0
acitretin Acitretin: An oral retinoid effective in the treatment of psoriasis. It is the major metabolite of ETRETINATE with the advantage of a much shorter half-life when compared with etretinate.. acitretin : A retinoid that consists of 3,7-dimethylnona-2,4,6,8-tetraenoic acid having a 4-methoxy-2,3,6-trimethylphenyl group attached at position 9.	7.59	2	0	acitretin; alpha,beta-unsaturated monocarboxylic acid; retinoid	keratolytic drug
topiramate Topiramate: A sulfamate-substituted fructose analog that was originally identified as a hypoglycemic agent. It is used for the treatment of EPILEPSY and MIGRAINE DISORDERS, and may also promote weight loss.. topiramate : A hexose derivative that is 2,3:4,5-di-O-isopropylidene-beta-D-fructopyranose in which the hydroxy group has been converted to the corresponding sulfamate ester. It blocks voltage-dependent sodium channels and is used as an antiepileptic and for the prevention of migraine.	2.05	1	0	cyclic ketal; ketohexose derivative; sulfamate ester	anticonvulsant; sodium channel blocker
fenretinide Fenretinide: A synthetic retinoid that is used orally as a chemopreventive against prostate cancer and in women at risk of developing contralateral breast cancer. It is also effective as an antineoplastic agent.. 4-hydroxyphenyl retinamide : A retinoid obtained by formal condensation of the carboxy group of all-trans retinoic acid and the anilino group of 4-hydroxyaniline. Synthetic retinoid agonist. Antiproliferative, antioxidant and anticancer agent with a long half-life in vivo. Apoptotic effects appear to be mediated by a mechanism distinct from that of 'classical' retinoids.	1.99	1	0	monocarboxylic acid amide; retinoid	antineoplastic agent; antioxidant
isofraxidin isofraxidin: also see fraxidin	2.04	1	0	hydroxycoumarin
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	7.48	2	0	carbon group element atom; elemental lead; metal atom	neurotoxin
5,5',6,6'-tetrachloro-1,1',3,3'-tetraethylbenzimidazolocarbocyanine 5,5',6,6'-tetrachloro-1,1',3,3'-tetraethylbenzimidazolocarbocyanine: structure given in first source. 1,1',3,3'-tetraethyl-5,5',6,6'-tetrachloroimidacarbocyanine : The cationic form of a C3 cyanine dye having 1,3-diethyl-5,6-dichloroindoleinine units at each end.	2	1	0	cyanine dye; indolium ion	fluorochrome
diamide Diamide: A sulfhydryl reagent which oxidizes sulfhydryl groups to the disulfide form. It is a radiation-sensitizing agent of anoxic bacterial and mammalian cells.	2.05	1	0	1,1'-azobis(N,N-dimethylformamide)
muconic acid muconic acid: a metabolite of benzene; reported to be a reliable indicator of occupational exposure to benzene; structure given in first source. trans,trans-muconic acid : The trans,trans-isomer of muconic acid. It is metabolite of benzene in humans and serves as a biomarker of occupational exposure to benzene.. muconic acid : A hexadienedioic acid with unsaturation at positions 2 and 4.	1.99	1	0	muconic acid	biomarker; human xenobiotic metabolite
ethyl fumarate [no description available]	5.69	7	1
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	2.47	2	0	boron group element atom; elemental aluminium; metal atom
alternariol alternariol: structure. alternariol : A benzochromenone that is 6H-benzo[c]chromen-6-one which is substituted by a methyl group at position 1 and by hydroxy groups at positions 3, 7, and 9. It is the most important mycotoxin produced by the black mould Alternaria species, which are the most common mycoflora infecting small grain cereals worldwide.	1.97	1	0	benzochromenone; phenols	EC 3.1.1.8 (cholinesterase) inhibitor; metabolite; mycotoxin
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)	7.43	2	0	metalloid atom; pnictogen	micronutrient
alternariol monomethyl ether djalonensone : A benzochromenone that is alternariol in which the hydroxy group at position 9 has been converted into the corresponding methyl ether. A natural product found in Chaetomium globosum as well as being one of the two most important compounds belonging to the group of Altenaria mycotoxins.	1.97	1	0	aromatic ether; benzochromenone	antifungal agent; fungal metabolite; mycotoxin
sulfur Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.	2.41	2	0	chalcogen; nonmetal atom	macronutrient
monomethyl fumarate monomethyl fumarate : A dicarboxylic acid monoester resulting from the formal condensation of one of the carboxy groups of fumaric acid with methanol. Is is a metabolite of dimethyl fumarate and used for the the treatment of patients with relapsing multiple sclerosis (MS). It also induces the NFE2L2 (Nrf2) transcription factor by binding to KEAP1.	2.46	2	0	dicarboxylic acid monoester; enoate ester; methyl ester	antioxidant; drug metabolite; immunomodulator
sedoheptulose [no description available]	2.05	1	0	ketoheptose
formylmethanofuran formylmethanofuran: proposed as intermediate in reduction of CO2 to methane	1.97	1	0	pentacarboxylic acid
fumarates Fumarates: Compounds based on fumaric acid.. fumarate(2-) : A C4-dicarboxylate that is the E-isomer of but-2-enedioate(2-)	18.73	750	24	butenedioate; C4-dicarboxylate	human metabolite; metabolite; Saccharomyces cerevisiae metabolite
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	3.54	8	0	cysteinium	fundamental metabolite
isophthalate isophthalate: RN given refers to parent cpd	1.98	1	0	dicarboxylic acid dianion
crotonic acid betaine crotonic acid betaine: RN given refers to inner salt without isomeric designation	2.01	1	0	4-(trimethylammonio)but-2-enoate
7-mercaptoheptanoylthreonine phosphate 7-mercaptoheptanoylthreonine phosphate: component B of the methylcoenzyme M methylreductase system of Methanobacterium thermoautotrophicum; structure given in first source	1.97	1	0	L-threonine derivative	coenzyme
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.	7.94	4	0	monoatomic phosphorus; nonmetal atom; pnictogen	macronutrient
ici 118551 ICI 118551: RN given refers to (R,R)-(+-)-isomer; structure in first source; ICI 111581 is hydrochloride of ICI 118551. ICI 118551 : An indane substituted at position 7 by a methyl group and at position 4 by a 3-(isopropylamino)-2-hydroxybutoxy group (the 2R,3S-diastereomer).	1.96	1	0	aromatic ether; indanes; secondary alcohol; secondary amino compound	beta-adrenergic antagonist
carbocyanines Carbocyanines: Compounds that contain three methine groups. They are frequently used as cationic dyes used for differential staining of biological materials.	2	1	0	cyanine dye; organic iodide salt	fluorochrome
ammonium sulfate Ammonium Sulfate: Sulfuric acid diammonium salt. It is used in CHEMICAL FRACTIONATION of proteins.. ammonium sulfate : An inorganic sulfate salt obtained by reaction of sulfuric acid with two equivalents of ammonia. A high-melting (decomposes above 280degreeC) white solid which is very soluble in water (70.6 g/100 g water at 0degreeC; 103.8 g/100 g water at 100degreeC), it is widely used as a fertilizer for alkaline soils.	1.96	1	0	ammonium salt; inorganic sulfate salt	fertilizer
selenium Selenium: An element with the atomic symbol Se, atomic number 34, and atomic weight 78.97. It is an essential micronutrient for mammals and other animals but is toxic in large amounts. Selenium protects intracellular structures against oxidative damage. It is an essential component of GLUTATHIONE PEROXIDASE.	2.43	2	0	chalcogen; nonmetal atom	micronutrient
oxalates Oxalates: Derivatives of OXALIC ACID. Included under this heading are a broad variety of acid forms, salts, esters, and amides that are derived from the ethanedioic acid structure.	4.33	6	0
antimycin a Antimycin A: An antibiotic substance produced by Streptomyces species. It inhibits mitochondrial respiration and may deplete cellular levels of ATP. Antimycin A1 has been used as a fungicide, insecticide, and miticide. (From Merck Index, 12th ed). antimycin A : A nine-membered bis-lactone having methyl substituents at the 2- and 6-positions, an n-hexyl substituent at the 8-position, an acyloxy substituent at the 7-position and an aroylamido substituent at the 3-position. It is produced by Streptomyces bacteria and has found commercial use as a fish poison.	2.89	4	0	amidobenzoic acid
ferrous fumarate ferrous fumarate: used in treatment of iron deficiency anemia; RN given refers to Fe(+2)[1:1] salt	1.93	1	0	dicarboxylic acid
myxothiazol myxothiazol: strobilurin analogue; methoxyacrylamide derivative; antifungal antibiotic from Myxococcus fulvus; structure given in first source. myxothiazol : A 2,4'-bi-1,3-thiazole substituted at the 4-position with a (1E,3S,4R,5E)-7-amino-3,5-dimethoxy-4-methyl-7-oxohepta-1,5-dien-1-yl] group and at the 2'-position with a (2S,3E,5E)-7-methylocta-3,5-dien-2-yl group. It is an inhibitor of coenzyme Q - cytochrome c reductase.	2.39	2	0
mucidin mucidin: produced by basidiomycete Oudemansiella mucida; strobilurin A produced by wood rot fungus Strobilurus tenacellus;. mucidin : An enoate ester that is the methyl ester of (2E,3Z,5E)-2-(methoxymethylene)-3-methyl-6-phenylhexa-3,5-dienoic acid.	1.98	1	0	enoate ester; enol ether	antifungal agent; fungal metabolite
menaquinol 6 menaquinol 6: a short chain analog of vitamin K2; physiological electron donor. menaquinol-6 : A menaquinol whose structure comprises a 2-methylbenzohydroquinone nucleus and a side chain of six isoprenoid units.	2.39	2	0	menaquinol	electron donor
rhodoquinone rhodoquinone: methoxy group of ubiquinone substituted with amino group; RN given refers to parent cpd	2.39	2	0
4,5-di-O-caffeoylquinic acid [no description available]	2.21	1	0	quinic acid
indigo carmine 3,5-di-O-(E)-caffeoylquinic acid: from roots of Lychnophora ericoides; structure in first source. 3,5-di-O-caffeoyl quinic acid : A carboxylic ester that is the diester obtained by the condensation of the hydroxy groups at positions 3 and 5 of (-)-quinic acid with the carboxy group of trans-caffeic acid. Isolated from Brazilian propolis and Suaeda glauca, it exhibits hepatoprotective and cytotoxic activities.	2.21	1	0
beta-tocopherol [no description available]	2.13	1	0	tocopherol; vitamin E	food component; plant metabolite
furagin Furagin: Nitrofuran derivative anti-infective agent used for urinary tract infections.. furagin : An imidazolidine-2,4-dione that is hydantoin substituted at position 1 by a [3-(5-nitro-2-furyl)prop-2-en-1-ylidene]amino group (the configuration of the C=C and C=N bonds in the grouping that links the two heterocycles is not specified). A nitrofuran antibiotic with properties similar to nitrofurantoin, furagin is used in the treatment of urinary tract infections.	3.47	1	1
fumagillin [no description available]	1.92	1	0	antibiotic antifungal drug; carboxylic ester; dicarboxylic acid monoester; meroterpenoid; organooxygen heterocyclic antibiotic; spiro-epoxide	angiogenesis inhibitor; antibacterial drug; antimicrobial agent; antiprotozoal drug; fungal metabolite; methionine aminopeptidase 2 inhibitor
voclosporin voclosporin: semi-synthetic cyclosporine A analog & calcineurin inhibitor; FDA approved use to treat lupus nephritis.	3.12	1	0	homodetic cyclic peptide
phosphocreatine Phosphocreatine: An endogenous substance found mainly in skeletal muscle of vertebrates. It has been tried in the treatment of cardiac disorders and has been added to cardioplegic solutions. (Reynolds JEF(Ed): Martindale: The Extra Pharmacopoeia (electronic version). Micromedex, Inc, Englewood, CO, 1996). phosphagen : Any of a group of guanidine or amidine phosphates that function as storage depots for high-energy phosphate in muscle with the purpose of regenerating ATP from ADP during muscular contraction.. N-phosphocreatine : A phosphoamino acid consisting of creatine having a phospho group attached at the primary nitrogen of the guanidino group.	2.91	4	0	phosphagen; phosphoamino acid	human metabolite; mouse metabolite
ubiquinol ubiquinol: reduced forms of ubiquinone; see also record for ubiquinol 10. ubiquinol-10 : A ubiquinol in which the polyprenyl substituent is decaprenyl.	1.97	1	0	polyprenylhydroquinone; ubiquinol	biomarker; metabolite
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.	2.03	1	0
edoxaban edoxaban : A monocarboxylic acid amide that is used (as its tosylate monohydrate) for the treatment of deep vein thrombosis and pulmonary embolism.	3.5	1	1	chloropyridine; monocarboxylic acid amide; tertiary amino compound; thiazolopyridine	anticoagulant; EC 3.4.21.6 (coagulation factor Xa) inhibitor; platelet aggregation inhibitor
fg-4592 roxadustat: structure in first source. roxadustat : An N-acylglycine resulting from the formal condensation of the amino group of glycine with the carboxy group of 4-hydroxy-1-methyl-7-phenoxyisoquinoline-3-carboxylic acid. It is an inhibitor of hypoxia inducible factor prolyl hydroxylase (HIF-PH).	2.53	2	0	aromatic ether; isoquinolines; N-acylglycine	EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor; EC 1.14.11.29 (hypoxia-inducible factor-proline dioxygenase) inhibitor
apremilast [no description available]	7.69	2	0	aromatic ether; N-acetylarylamine; phthalimides; sulfone	non-steroidal anti-inflammatory drug; phosphodiesterase IV inhibitor
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	5.34	18	0	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
cytochrome c-t Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.	2.47	2	0
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	3	4	0	glycoside
sodium borate borax: see also sodium borate. borax : A hydrate that is the decahydrate form of disodium tetraborate.	2.06	1	0
chlorophyll a Chlorophyll: Porphyrin derivatives containing magnesium that act to convert light energy in photosynthetic organisms.. chlorophyll : A family of magnesium porphyrins, defined by the presence of a fifth ring beyond the four pyrrole-like rings. The rings can have various side chains which usually include a long phytol chain.	2.05	1	0	chlorophyll; methyl ester	cofactor
endiandrin a endiandrin A: a potent glucocorticoid receptor binder isolated from the Australian plant Endiandra anthropophagorum; structure in first source	2.05	1	0
sodium salicylate [no description available]	2.01	1	0	organic molecular entity
ubiquinone Ubiquinone: A lipid-soluble benzoquinone which is involved in ELECTRON TRANSPORT in mitochondrial preparations. The compound occurs in the majority of aerobic organisms, from bacteria to higher plants and animals.	3.38	7	0
succinyladenosine succinyladenosine: found in body fluids of children with severe psychomotor delay & autism; RN given refers to (L)-isomer. succinyladenosine : An aspartic acid derivative that is L-aspartic acid in which one of the amine hydrogens is substituted by a 9-beta-D-ribofuranosyl-9H-purin-6-yl group.	2	1	0	adenosines; amino dicarboxylic acid; L-aspartic acid derivative	metabolite
chitosan [no description available]	3.23	5	0
mesna Mesna: A sulfhydryl compound used to prevent urothelial toxicity by inactivating metabolites from ANTINEOPLASTIC AGENTS, such as IFOSFAMIDE or CYCLOPHOSPHAMIDE.	1.97	1	0	organosulfonic acid
sodium stearyl fumarate sodium stearyl fumarate: an excipient	2.17	1	0
sodium hypochlorite Sodium Hypochlorite: It is used as an oxidizing and bleaching agent and as a disinfectant. (From Grant & Hackh's Chemical Dictionary, 5th ed). sodium hypochlorite : An inorganic sodium salt in which hypochlorite is the counterion. It is used as a bleaching and disinfecting agent and is commonly found in household bleach.	7.46	2	0	inorganic sodium salt	bleaching agent; disinfectant
sodium lactate Sodium Lactate: The sodium salt of racemic or inactive lactic acid. It is a hygroscopic agent used intravenously as a systemic and urinary alkalizer.. sodium lactate : An organic sodium salt having lactate as the counterion.	2	1	0	lactate salt; organic sodium salt	food acidity regulator; food preservative
penicillin g sodium [no description available]	2.03	1	0	organic sodium salt
stearates Stearates: Salts and esters of the 18-carbon saturated, monocarboxylic acid--stearic acid.	2.17	1	0
mersalyl Mersalyl: A toxic thiol mercury salt formerly used as a diuretic. It inhibits various biochemical functions, especially in mitochondria, and is used to study those functions.	1.96	1	0
chiniofon Hydroxyquinolines: The 8-hydroxy derivatives inhibit various enzymes and their halogenated derivatives, though neurotoxic, are used as topical anti-infective agents, among other uses.	2.39	2	0
ethyl cellulose [no description available]	2.45	2	0	glycoside
quetiapine fumarate Quetiapine Fumarate: A dibenzothiazepine and ANTIPSYCHOTIC AGENT that targets the SEROTONIN 5-HT2 RECEPTOR; HISTAMINE H1 RECEPTOR, adrenergic alpha1 and alpha2 receptors, as well as the DOPAMINE D1 RECEPTOR and DOPAMINE D2 RECEPTOR. It is used in the treatment of SCHIZOPHRENIA; BIPOLAR DISORDER and DEPRESSIVE DISORDER.	4.31	1	1	fumarate salt
s-(1,2-dicarboxyethyl)cysteine S-(1,2-dicarboxyethyl)cysteine: isolated from a toadstool, Amanita pantherina as a mixture of (2R),(1'R) and (2R),(1'S) diastereomers. S-(2-succinyl)-L-cysteine : An L-cysteine thioether that is L-cysteine in which the hydrogen of the thiol group has been replaced by a 1,2-dicarboxyethyl group. It is a chemical modification which occurs in tissue proteins and formed by a Michael addition of cysteine to fumaric acid.	2.47	2	0	L-cysteine thioether; tricarboxylic acid	human metabolite; Maillard reaction product
mannans [no description available]	2.07	1	0
glycolipids [no description available]	3.27	1	0
piperidines Piperidines: A family of hexahydropyridines.	2.73	3	0
fructose-1,6-diphosphate fructose-1,6-diphosphate: RN refers to (D)-isomer	2.43	2	0
calcipotriene calcipotriene: a topical dermatologic for the treatment of moderate plaque psoriasis; structure in first source. calcipotriol hydrate : A hydrate that is the monohydrate form of calcipotriol. It is used in combination with betamethasone dipropionate, a corticosteroid, for the topical treatment of plaque psoriasis in adult patients.	2.21	1	0	hydrate	antipsoriatic
methylcellulose Methylcellulose: Methylester of cellulose. Methylcellulose is used as an emulsifying and suspending agent in cosmetics, pharmaceutics and the chemical industry. It is used therapeutically as a bulk laxative.	2.95	4	0
heme Heme: The color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins.. ferroheme : Any iron(II)--porphyrin coordination complex.. ferroheme b : Heme b in which the iron has oxidation state +2.. heme : A heme is any tetrapyrrolic chelate of iron.	4.71	9	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.	3.73	10	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.	2.1	1	0	monohydroxybenzoate	plant metabolite
dicumarol Dicumarol: An oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases.	1.99	1	0	hydroxycoumarin	anticoagulant; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; Hsp90 inhibitor; vitamin K antagonist
laquinimod [no description available]	4.91	4	0	aromatic amide
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.	2.04	1	0	benzenes; hydroxycoumarin; methyl ketone
antimycin [no description available]	1.97	1	0
teriflunomide [no description available]	4.91	4	0	(trifluoromethyl)benzenes; aromatic amide; enamide; enol; nitrile; secondary carboxamide	drug metabolite; EC 1.3.98.1 [dihydroorotate oxidase (fumarate)] inhibitor; hepatotoxic agent; non-steroidal anti-inflammatory drug; tyrosine kinase inhibitor
2-[[[4-hydroxy-2-oxo-1-(phenylmethyl)-3-quinolinyl]-oxomethyl]amino]acetic acid [no description available]	2.21	1	0	quinolines
transforming growth factor beta Transforming Growth Factor beta: A factor synthesized in a wide variety of tissues. It acts synergistically with TGF-alpha in inducing phenotypic transformation and can also act as a negative autocrine growth factor. TGF-beta has a potential role in embryonal development, cellular differentiation, hormone secretion, and immune function. TGF-beta is found mostly as homodimer forms of separate gene products TGF-beta1, TGF-beta2 or TGF-beta3. Heterodimers composed of TGF-beta1 and 2 (TGF-beta1.2) or of TGF-beta2 and 3 (TGF-beta2.3) have been isolated. The TGF-beta proteins are synthesized as precursor proteins.	2.01	1	0
3-[[2-(2-pyridinyl)-6-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)-4-pyrimidinyl]amino]propanoic acid [no description available]	2.21	1	0	organonitrogen heterocyclic compound
brine brine: not from seawater; contains sodium chloride; calcium chloride; magnesium chloride; one or all of the above	2.8	3	0
bay 85-3934 [no description available]	2.21	1	0
gt0918 proxalutamide: has antineoplastic activity	2.1	1	0
agar Agar: A complex sulfated polymer of galactose units, extracted from Gelidium cartilagineum, Gracilaria confervoides, and related red algae. It is used as a gel in the preparation of solid culture media for microorganisms, as a bulk laxative, in making emulsions, and as a supporting medium for immunodiffusion and immunoelectrophoresis.. agar : A complex mixture of polysaccharides extracted from species of red algae. Its two main components are agarose and agaropectin. Agarose is the component responsible for the high-strength gelling properties of agar, while agaropectin provides the viscous properties.	7.25	1	0
caseins Caseins: A mixture of related phosphoproteins occurring in milk and cheese. The group is characterized as one of the most nutritive milk proteins, containing all of the common amino acids and rich in the essential ones.	2.36	2	0
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	2	1	0
lewis x antigen Lewis X Antigen: A trisaccharide antigen expressed on glycolipids and many cell-surface glycoproteins. In the blood the antigen is found on the surface of NEUTROPHILS; EOSINOPHILS; and MONOCYTES. In addition, Lewis X antigen is a stage-specific embryonic antigen.	1.98	1	0
humulin s Insulin, Regular, Human: Regular insulin preparations that contain the HUMAN insulin peptide sequence.. insulin (human) : An insulin that is produced in the pancreas and involved in regulating the metabolism of carbohydrates (particularly glucose) and fats. Commonly thought of as a protein, it consists of two peptide chains, one containing 21 amino acid residues and the other containing 30; the chains are joined together by 2 disulfide bonds. Recombinant insulin is identical to human insulin, but is synthesised by inserting the human insulin gene into E. coli, which then produces insulin for human use. It is used in the treatment of type I and type II diabetes.	2.03	1	0
cyclosporine Cyclosporine: A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).	3.84	3	0
orabase Orabase: used in therapy of oral mucosal ulcers	2.07	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.	1.93	1	0
acyclovir Acyclovir: A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.. acyclovir : An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.	7.8	3	0	2-aminopurines; oxopurine	antimetabolite; antiviral drug
inosinic acid Inosine Monophosphate: Inosine 5'-Monophosphate. A purine nucleotide which has hypoxanthine as the base and one phosphate group esterified to the sugar moiety.	1.97	1	0	inosine phosphate; purine ribonucleoside 5'-monophosphate	Escherichia coli metabolite; human metabolite; mouse metabolite
pheophytin a pheophytin a: structure given in first source; RN given refers to (3S-(3alpha(2E,7S,11S),4beta,21beta))-isomer	2.41	1	0
rifampin Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)	2	1	0	cyclic ketal; hydrazone; N-iminopiperazine; N-methylpiperazine; rifamycins; semisynthetic derivative; zwitterion	angiogenesis inhibitor; antiamoebic agent; antineoplastic agent; antitubercular agent; DNA synthesis inhibitor; EC 2.7.7.6 (RNA polymerase) inhibitor; Escherichia coli metabolite; geroprotector; leprostatic drug; neuroprotective agent; pregnane X receptor agonist; protein synthesis inhibitor
sildenafil citrate Sildenafil Citrate: A PHOSPHODIESTERASE TYPE-5 INHIBITOR; VASODILATOR AGENT and UROLOGICAL AGENT that is used in the treatment of ERECTILE DYSFUNCTION and PRIMARY PULMONARY HYPERTENSION.. sildenafil citrate : The citrate salt of sildenafil.	2.08	1	0	citrate salt	EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor; vasodilator agent
phosphocreatinine phosphocreatinine: cyclic deriv of phosphocreatine; RN given refers to parent cpd	1.98	1	0	organonitrogen compound; organooxygen compound
reamberin [no description available]	2.15	1	0
phenanthrenes Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.	3.16	1	0

Condition	Indicated	Relationship Strength	Studies	Trials
Innate Inflammatory Response [description not available]	0	3.03	4	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.	0	8.03	4	0
Benign Neoplasms [description not available]	0	3.64	2	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.	0	3.64	2	0
Cancer of Kidney [description not available]	0	4.22	6	0
Ischemia A hypoperfusion of the BLOOD through an organ or tissue caused by a PATHOLOGIC CONSTRICTION or obstruction of its BLOOD VESSELS, or an absence of BLOOD CIRCULATION.	0	2.58	2	0
Kidney Neoplasms Tumors or cancers of the KIDNEY.	0	4.22	6	0
Palmoplantaris Pustulosis [description not available]	0	11.28	40	4
Psoriasis A common genetically determined, chronic, inflammatory skin disease characterized by rounded erythematous, dry, scaling patches. The lesions have a predilection for nails, scalp, genitalia, extensor surfaces, and the lumbosacral region. Accelerated epidermopoiesis is considered to be the fundamental pathologic feature in psoriasis.	1	13.28	40	4
2019 Novel Coronavirus Disease [description not available]	0	3.99	1	1
Metabolic Acidosis [description not available]	0	2.46	2	0
Acidosis A pathologic condition of acid accumulation or depletion of base in the body. The two main types are RESPIRATORY ACIDOSIS and metabolic acidosis, due to metabolic acid build up.	0	2.46	2	0
ST Elevated Myocardial Infarction [description not available]	0	2.25	1	0
ST Elevation Myocardial Infarction A clinical syndrome defined by MYOCARDIAL ISCHEMIA symptoms; persistent elevation in the ST segments of the ELECTROCARDIOGRAM; and release of BIOMARKERS of myocardial NECROSIS (e.g., elevated TROPONIN levels). ST segment elevation in the ECG is often used in determining the treatment protocol (see also NON-ST ELEVATION MYOCARDIAL INFARCTION).	0	2.25	1	0
Acute Liver Injury, Drug-Induced [description not available]	0	2.25	1	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.	0	2.25	1	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	0	3.13	5	0
Hepatocellular Carcinoma [description not available]	0	2.25	1	0
Cancer of Liver [description not available]	0	2.25	1	0
Metastase [description not available]	0	2.25	1	0
Angiogenesis, Pathologic [description not available]	0	2.25	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.	0	2.25	1	0
Liver Neoplasms Tumors or cancer of the LIVER.	0	2.25	1	0
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	0	2.25	1	0
Allergic Encephalomyelitis [description not available]	0	2.17	1	0
MS (Multiple Sclerosis) [description not available]	0	5.27	6	0
Multiple Sclerosis An autoimmune disorder mainly affecting young adults and characterized by destruction of myelin in the central nervous system. Pathologic findings include multiple sharply demarcated areas of demyelination throughout the white matter of the central nervous system. Clinical manifestations include visual loss, extra-ocular movement disorders, paresthesias, loss of sensation, weakness, dysarthria, spasticity, ataxia, and bladder dysfunction. The usual pattern is one of recurrent attacks followed by partial recovery (see MULTIPLE SCLEROSIS, RELAPSING-REMITTING), but acute fulminating and chronic progressive forms (see MULTIPLE SCLEROSIS, CHRONIC PROGRESSIVE) also occur. (Adams et al., Principles of Neurology, 6th ed, p903)	0	10.27	6	0
Diabetic Glomerulosclerosis [description not available]	0	3.09	1	0
Diabetic Nephropathies KIDNEY injuries associated with diabetes mellitus and affecting KIDNEY GLOMERULUS; ARTERIOLES; KIDNEY TUBULES; and the interstitium. Clinical signs include persistent PROTEINURIA, from microalbuminuria progressing to ALBUMINURIA of greater than 300 mg/24 h, leading to reduced GLOMERULAR FILTRATION RATE and END-STAGE RENAL DISEASE.	0	3.09	1	0
Anesthesia Related Hyperthermia [description not available]	0	2.15	1	0
Lymphocytopenia [description not available]	0	2.21	1	0
Lymphopenia Reduction in the number of lymphocytes.	0	7.21	1	0
Carcinogenesis The origin, production or development of cancer through genotypic and phenotypic changes which upset the normal balance between cell proliferation and cell death. Carcinogenesis generally requires a constellation of steps, which may occur quickly or over a period of many years.	0	2.21	1	0
Carcinoma, Anaplastic [description not available]	0	2.21	1	0
Cancer of Nasopharynx [description not available]	0	2.21	1	0
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	0	2.21	1	0
Nasopharyngeal Neoplasms Tumors or cancer of the NASOPHARYNX.	0	2.21	1	0
Genital Tract Infections [description not available]	0	3.46	1	1
Urinary Tract Infections Inflammatory responses of the epithelium of the URINARY TRACT to microbial invasions. They are often bacterial infections with associated BACTERIURIA and PYURIA.	0	4.43	2	2
Cancer of Skin [description not available]	0	2.48	2	0
Cancer of the Uterus [description not available]	0	2.48	2	0
Leiomyomatosis The state of having multiple leiomyomas throughout the body. (Stedman, 25th ed)	0	3.66	3	0
Cancer Syndromes, Hereditary [description not available]	0	2.48	2	0
Skin Neoplasms Tumors or cancer of the SKIN.	0	2.48	2	0
Uterine Neoplasms Tumors or cancer of the UTERUS.	0	2.48	2	0
Antibody Deficiency Syndrome [description not available]	0	2.49	2	0
Immune Reconstitution Disease [description not available]	0	2.08	1	0
Encephalitis, JC Polyomavirus [description not available]	0	2.49	2	0
Immunologic Deficiency Syndromes Syndromes in which there is a deficiency or defect in the mechanisms of immunity, either cellular or humoral.	0	2.49	2	0
Leukoencephalopathy, Progressive Multifocal An opportunistic viral infection of the central nervous system associated with conditions that impair cell-mediated immunity (e.g., ACQUIRED IMMUNODEFICIENCY SYNDROME and other IMMUNOLOGIC DEFICIENCY SYNDROMES; HEMATOLOGIC NEOPLASMS; IMMUNOSUPPRESSION; and COLLAGEN DISEASES). The causative organism is JC Polyomavirus (JC VIRUS) which primarily affects oligodendrocytes, resulting in multiple areas of demyelination. Clinical manifestations include DEMENTIA; ATAXIA; visual disturbances; and other focal neurologic deficits, generally progressing to a vegetative state within 6 months. (From Joynt, Clinical Neurology, 1996, Ch26, pp36-7)	0	2.49	2	0
Tooth Erosion Progressive loss of the hard substance of a tooth by chemical processes that do not involve bacterial action. (Jablonski, Dictionary of Dentistry, 1992, p296)	0	2.08	1	0
Chronic Illness [description not available]	0	3.8	2	1
Necrotizing Pyelonephritis [description not available]	0	3.47	1	1
Urinary Calculi Low-density crystals or stones in any part of the URINARY TRACT. Their chemical compositions often include CALCIUM OXALATE, magnesium ammonium phosphate (struvite), CYSTINE, or URIC ACID.	0	3.47	1	1
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	0	3.8	2	1
Pyelonephritis Inflammation of the KIDNEY involving the renal parenchyma (the NEPHRONS); KIDNEY PELVIS; and KIDNEY CALICES. It is characterized by ABDOMINAL PAIN; FEVER; NAUSEA; VOMITING; and occasionally DIARRHEA.	0	3.47	1	1
Acute Relapsing Multiple Sclerosis [description not available]	0	4.49	3	0
Cholera Infantum [description not available]	0	4.76	2	1
Flushing A transient reddening of the face that may be due to fever, certain drugs, exertion, or stress.	0	3.67	3	0
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	0	3.33	2	0
Multiple Sclerosis, Relapsing-Remitting The most common clinical variant of MULTIPLE SCLEROSIS, characterized by recurrent acute exacerbations of neurologic dysfunction followed by partial or complete recovery. Common clinical manifestations include loss of visual (see OPTIC NEURITIS), motor, sensory, or bladder function. Acute episodes of demyelination may occur at any site in the central nervous system, and commonly involve the optic nerves, spinal cord, brain stem, and cerebellum. (Adams et al., Principles of Neurology, 6th ed, pp903-914)	0	4.49	3	0
Orphan Diseases Rare diseases that have not been well studied.	0	3.01	1	0
Pulmonary Sarcoidosis [description not available]	0	3.01	1	0
Besnier-Boeck Disease [description not available]	0	4.76	2	1
Dermatoses [description not available]	0	5.82	4	2
Sarcoidosis An idiopathic systemic inflammatory granulomatous disorder comprised of epithelioid and multinucleated giant cells with little necrosis. It usually invades the lungs with fibrosis and may also involve lymph nodes, skin, liver, spleen, eyes, phalangeal bones, and parotid glands.	0	9.76	2	1
Skin Diseases Diseases involving the DERMIS or EPIDERMIS.	0	10.82	4	2
Sarcoidosis, Pulmonary Sarcoidosis affecting predominantly the lungs, the site most frequently involved and most commonly causing morbidity and mortality in sarcoidosis. Pulmonary sarcoidosis is characterized by sharply circumscribed granulomas in the alveolar, bronchial, and vascular walls, composed of tightly packed cells derived from the mononuclear phagocyte system. The clinical symptoms when present are dyspnea upon exertion, nonproductive cough, and wheezing. (Cecil Textbook of Medicine, 19th ed, p431)	0	3.01	1	0
Dermatitis, Eczematous [description not available]	0	3.48	1	1
Eczema A pruritic papulovesicular dermatitis occurring as a reaction to many endogenous and exogenous agents (Dorland, 27th ed).	0	8.48	1	1
Cancer of Prostate [description not available]	0	2.48	2	0
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	0	2.48	2	0
Apoplexy [description not available]	0	2.1	1	0
Cardiovascular Stroke [description not available]	0	2.1	1	0
Injury, Ischemia-Reperfusion [description not available]	0	2.1	1	0
Myocardial Infarction NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).	0	2.1	1	0
Reperfusion Injury Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.	0	2.1	1	0
Stroke A group of pathological conditions characterized by sudden, non-convulsive loss of neurological function due to BRAIN ISCHEMIA or INTRACRANIAL HEMORRHAGES. Stroke is classified by the type of tissue NECROSIS, such as the anatomic location, vasculature involved, etiology, age of the affected individual, and hemorrhagic vs. non-hemorrhagic nature. (From Adams et al., Principles of Neurology, 6th ed, pp777-810)	0	2.1	1	0
Health Care Associated Infection [description not available]	0	3.48	1	1
Cross Infection Any infection which a patient contracts in a health-care institution.	0	3.48	1	1
Genetic Predisposition [description not available]	0	2.11	1	0
Paraganglioma, Gangliocytic [description not available]	0	2.11	1	0
Pheochromocytoma, Extra-Adrenal [description not available]	0	2.11	1	0
Paraganglioma A neural crest tumor usually derived from the chromoreceptor tissue of a paraganglion, such as the carotid body, or medulla of the adrenal gland (usually called a chromaffinoma or pheochromocytoma). It is more common in women than in men. (Stedman, 25th ed; from Segen, Dictionary of Modern Medicine, 1992)	0	2.11	1	0
Pheochromocytoma A usually benign, well-encapsulated, lobular, vascular tumor of chromaffin tissue of the ADRENAL MEDULLA or sympathetic paraganglia. The cardinal symptom, reflecting the increased secretion of EPINEPHRINE and NOREPINEPHRINE, is HYPERTENSION, which may be persistent or intermittent. During severe attacks, there may be HEADACHE; SWEATING, palpitation, apprehension, TREMOR; PALLOR or FLUSHING of the face, NAUSEA and VOMITING, pain in the CHEST and ABDOMEN, and paresthesias of the extremities. The incidence of malignancy is as low as 5% but the pathologic distinction between benign and malignant pheochromocytomas is not clear. (Dorland, 27th ed; DeVita Jr et al., Cancer: Principles & Practice of Oncology, 3d ed, p1298)	0	2.11	1	0
Cancer of Head [description not available]	0	2.11	1	0
Head and Neck Neoplasms Soft tissue tumors or cancer arising from the mucosal surfaces of the LIP; oral cavity; PHARYNX; LARYNX; and cervical esophagus. Other sites included are the NOSE and PARANASAL SINUSES; SALIVARY GLANDS; THYROID GLAND and PARATHYROID GLANDS; and MELANOMA and non-melanoma skin cancers of the head and neck. (from Holland et al., Cancer Medicine, 4th ed, p1651)	0	2.11	1	0
Acute Myelogenous Leukemia [description not available]	0	2.13	1	0
Neuroblastoma A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)	0	2.13	1	0
Leukemia, Myeloid, Acute Clonal expansion of myeloid blasts in bone marrow, blood, and other tissue. Myeloid leukemias develop from changes in cells that normally produce NEUTROPHILS; BASOPHILS; EOSINOPHILS; and MONOCYTES.	0	2.13	1	0
Brain Disorders [description not available]	0	2.15	1	0
Brain Diseases Pathologic conditions affecting the BRAIN, which is composed of the intracranial components of the CENTRAL NERVOUS SYSTEM. This includes (but is not limited to) the CEREBRAL CORTEX; intracranial white matter; BASAL GANGLIA; THALAMUS; HYPOTHALAMUS; BRAIN STEM; and CEREBELLUM.	0	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)	0	2.42	2	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	0	2.05	1	0
Inborn Errors of Metabolism [description not available]	0	5.46	8	0
Metabolism, Inborn Errors Errors in metabolic processes resulting from inborn genetic mutations that are inherited or acquired in utero.	0	5.46	8	0
Dental Plaque A film that attaches to teeth, often causing DENTAL CARIES and GINGIVITIS. It is composed of MUCINS, secreted from salivary glands, and microorganisms.	0	2.41	2	0
Acute Kidney Failure [description not available]	0	7.41	2	0
Acute Kidney Injury Abrupt reduction in kidney function. Acute kidney injury encompasses the entire spectrum of the syndrome including acute kidney failure; ACUTE KIDNEY TUBULAR NECROSIS; and other less severe conditions.	0	2.41	2	0
Cerebral Cortical Dysplasia [description not available]	0	2.06	1	0
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	0	3.1	5	0
Swine Diseases Diseases of domestic swine and of the wild boar of the genus Sus.	0	2.44	2	0
Salmonella Infections, Animal Infections in animals with bacteria of the genus SALMONELLA.	0	2.44	2	0
Granuloma Annulare Benign granulomatous disease of unknown etiology characterized by a ring of localized or disseminated papules or nodules on the skin and palisading histiocytes surrounding necrobiotic tissue resulting from altered collagen structures.	0	9.11	3	1
Weight Gain Increase in BODY WEIGHT over existing weight.	0	4.88	8	1
Achlorhydria A lack of HYDROCHLORIC ACID in GASTRIC JUICE despite stimulation of gastric secretion.	0	2.07	1	0
Colorectal Cancer [description not available]	0	2.07	1	0
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	0	2.07	1	0
Leishmania Infection [description not available]	0	2.07	1	0
Leishmaniasis A disease caused by any of a number of species of protozoa in the genus LEISHMANIA. There are four major clinical types of this infection: cutaneous (Old and New World) (LEISHMANIASIS, CUTANEOUS), diffuse cutaneous (LEISHMANIASIS, DIFFUSE CUTANEOUS), mucocutaneous (LEISHMANIASIS, MUCOCUTANEOUS), and visceral (LEISHMANIASIS, VISCERAL).	0	2.07	1	0
Urinary Lithiasis [description not available]	0	2.07	1	0
Complication, Postoperative [description not available]	0	2.07	1	0
Adenoma, Prostatic [description not available]	0	2.07	1	0
Postoperative Complications Pathologic processes that affect patients after a surgical procedure. They may or may not be related to the disease for which the surgery was done, and they may or may not be direct results of the surgery.	0	2.07	1	0
Prostatic Hyperplasia Increase in constituent cells in the PROSTATE, leading to enlargement of the organ (hypertrophy) and adverse impact on the lower urinary tract function. This can be caused by increased rate of cell proliferation, reduced rate of cell death, or both.	0	2.07	1	0
Urolithiasis Formation of stones in any part of the URINARY TRACT, usually in the KIDNEY; URINARY BLADDER; or the URETER.	0	2.07	1	0
Cystic Echinococcosis [description not available]	0	2.01	1	0
Coenuri Infection [description not available]	0	2.01	1	0
Cysticercosis Infection with CYSTICERCUS, the larval form of the various tapeworms of the genus Taenia (usually T. solium in man). In humans they penetrate the intestinal wall and invade subcutaneous tissue, brain, eye, muscle, heart, liver, lung, and peritoneum. Brain involvement results in NEUROCYSTICERCOSIS.	0	2.01	1	0
Epulides, Giant Cell [description not available]	0	3.81	2	1
Granuloma, Giant Cell A non-neoplastic inflammatory lesion, usually of the jaw or gingiva, containing large, multinucleated cells. It includes reparative giant cell granuloma. Peripheral giant cell granuloma refers to the gingiva (giant cell epulis); central refers to the jaw.	0	3.81	2	1
Psychoses [description not available]	0	4.31	1	1
Dementia Praecox [description not available]	0	4.31	1	1
Psychotic Disorders Disorders in which there is a loss of ego boundaries or a gross impairment in reality testing with delusions or prominent hallucinations. (From DSM-IV, 1994)	0	4.31	1	1
Schizophrenia A severe emotional disorder of psychotic depth characteristically marked by a retreat from reality with delusion formation, HALLUCINATIONS, emotional disharmony, and regressive behavior.	0	4.31	1	1
Adhesions, Tissue [description not available]	0	2.01	1	0
E coli Infections [description not available]	0	2.42	2	0
Diarrhea An increased liquidity or decreased consistency of FECES, such as running stool. Fecal consistency is related to the ratio of water-holding capacity of insoluble solids to total water, rather than the amount of water present. Diarrhea is not hyperdefecation or increased fecal weight.	0	2.42	2	0
Escherichia coli Infections Infections with bacteria of the species ESCHERICHIA COLI.	0	2.42	2	0
EHS Tumor [description not available]	0	1.93	1	0
Reticulum Cell-Like Sarcoma, Yoshida [description not available]	0	1.93	1	0
Adrenal Gland Hypofunction [description not available]	0	1.93	1	0
Starvation Lengthy and continuous deprivation of food. (Stedman, 25th ed)	0	1.93	1	0
Adrenal Insufficiency Conditions in which the production of adrenal CORTICOSTEROIDS falls below the requirement of the body. Adrenal insufficiency can be caused by defects in the ADRENAL GLANDS, the PITUITARY GLAND, or the HYPOTHALAMUS.	0	6.93	1	0
Anemia, Hypochromic Anemia characterized by a decrease in the ratio of the weight of hemoglobin to the volume of the erythrocyte, i.e., the mean corpuscular hemoglobin concentration is less than normal. The individual cells contain less hemoglobin than they could have under optimal conditions. Hypochromic anemia may be caused by iron deficiency from a low iron intake, diminished iron absorption, or excessive iron loss. It can also be caused by infections or other diseases, therapeutic drugs, lead poisoning, and other conditions. (Stedman, 25th ed; from Miale, Laboratory Medicine: Hematology, 6th ed, p393)	0	1.93	1	0
Anemia A reduction in the number of circulating ERYTHROCYTES or in the quantity of HEMOGLOBIN.	0	1.93	1	0
Poultry Diseases Diseases of birds which are raised as a source of meat or eggs for human consumption and are usually found in barnyards, hatcheries, etc. The concept is differentiated from BIRD DISEASES which is for diseases of birds not considered poultry and usually found in zoos, parks, and the wild.	0	2.43	2	0
Anoxemia [description not available]	0	4.29	4	1
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	0	4.29	4	1
Dehydration The condition that results from excessive loss of water from a living organism.	0	2.02	1	0
Necrobiosis Lipoidica Diabeticorum [description not available]	0	3.41	1	1
Cheilitis Inflammation of the lips. It is of various etiologies and degrees of pathology.	0	3.41	1	1
Necrobiosis Lipoidica A degenerative disease of the dermal connective tissue characterized by the development of erythematous papules or nodules in the pretibial area. The papules form plaques covered with telangiectatic vessels. More than half of the affected patients have diabetes.	0	3.41	1	1
Adenocarcinoma Of Kidney [description not available]	0	2.94	1	0
Symptom Cluster [description not available]	0	2.94	1	0
Carcinoma, Renal Cell A heterogeneous group of sporadic or hereditary carcinoma derived from cells of the KIDNEYS. There are several subtypes including the clear cells, the papillary, the chromophobe, the collecting duct, the spindle cells (sarcomatoid), or mixed cell-type carcinoma.	0	2.94	1	0
Syndrome A characteristic symptom complex.	0	2.94	1	0
Cyst [description not available]	0	2.43	2	0
Cystic Periventricular Leukomalacia [description not available]	0	2.02	1	0
Leukomalacia, Periventricular Degeneration of white matter adjacent to the CEREBRAL VENTRICLES following cerebral hypoxia or BRAIN ISCHEMIA in neonates. The condition primarily affects white matter in the perfusion zone between superficial and deep branches of the MIDDLE CEREBRAL ARTERY. Clinical manifestations include VISION DISORDERS; CEREBRAL PALSY; PARAPLEGIA; SEIZURES; and cognitive disorders. (From Adams et al., Principles of Neurology, 6th ed, p1021; Joynt, Clinical Neurology, 1997, Ch4, pp30-1)	0	2.02	1	0
Chronic Insomnia [description not available]	0	3.41	1	1
Anxiety Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.	0	3.41	1	1
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	0	3.41	1	1
Sleep Initiation and Maintenance Disorders Disorders characterized by impairment of the ability to initiate or maintain sleep. This may occur as a primary disorder or in association with another medical or psychiatric condition.	0	3.41	1	1
Hot Flashes A sudden, temporary sensation of heat predominantly experienced by some women during MENOPAUSE. (Random House Unabridged Dictionary, 2d ed)	0	3.41	1	1
Complications, Hematologic Pregnancy [description not available]	0	3.41	1	1
Anemias, Iron-Deficiency [description not available]	0	3.41	1	1
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	0	4.08	3	1
Anemia, Iron-Deficiency Anemia characterized by decreased or absent iron stores, low serum iron concentration, low transferrin saturation, and low hemoglobin concentration or hematocrit value. The erythrocytes are hypochromic and microcytic and the iron binding capacity is increased.	0	3.41	1	1
Decreased Muscle Tone [description not available]	0	2.91	4	0
Absence Seizure [description not available]	0	2.02	1	0
Brain Diseases, Metabolic, Familial [description not available]	0	2.02	1	0
Seizures Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.	0	2.02	1	0
Developmental Psychomotor Disorders [description not available]	0	2.03	1	0
Alloxan Diabetes [description not available]	0	2.03	1	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	0	3.47	8	0
Rachitis [description not available]	0	2.04	1	0
Adenocarcinoma, Basal Cell [description not available]	0	1.96	1	0
Carcinoma, Epidermoid [description not available]	0	1.96	1	0
Cancer of Lung [description not available]	0	2.38	2	0
Papilloma, Squamous Cell [description not available]	0	1.96	1	0
Cancer of Stomach [description not available]	0	1.96	1	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	0	1.96	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)	0	1.96	1	0
Lung Neoplasms Tumors or cancer of the LUNG.	0	2.38	2	0
Papilloma A circumscribed benign epithelial tumor projecting from the surrounding surface; more precisely, a benign epithelial neoplasm consisting of villous or arborescent outgrowths of fibrovascular stroma covered by neoplastic cells. (Stedman, 25th ed)	0	1.96	1	0
Stomach Neoplasms Tumors or cancer of the STOMACH.	0	1.96	1	0
Carcinoma, Ehrlich Tumor A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.	0	1.96	1	0
Leukemia L 1210 [description not available]	0	1.96	1	0
Experimental Neoplasms [description not available]	0	1.96	1	0
Cerebral Ischemia [description not available]	0	1.98	1	0
Brain Embolism and Thrombosis [description not available]	0	1.98	1	0
Brain Ischemia Localized reduction of blood flow to brain tissue due to arterial obstruction or systemic hypoperfusion. This frequently occurs in conjunction with brain hypoxia (HYPOXIA, BRAIN). Prolonged ischemia is associated with BRAIN INFARCTION.	0	1.98	1	0
Keratoderma Blennorrhagicum [description not available]	0	1.99	1	0
Keratosis Any horny growth such as a wart or callus.	0	1.99	1	0
Atrophy Decrease in the size of a cell, tissue, organ, or multiple organs, associated with a variety of pathological conditions such as abnormal cellular changes, ischemia, malnutrition, or hormonal changes.	0	2.91	1	0
Acute Confusional Senile Dementia [description not available]	0	1.99	1	0
Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)	0	1.99	1	0
Degenerative Diseases, Central Nervous System [description not available]	0	1.99	1	0
Amino Acid Metabolism Disorders, Inborn [description not available]	0	1.99	1	0
Neurodegenerative Diseases Hereditary and sporadic conditions which are characterized by progressive nervous system dysfunction. These disorders are often associated with atrophy of the affected central or peripheral nervous system structures.	0	1.99	1	0
Elaeophoriasis [description not available]	0	2	1	0
Setariasis Infection with nematodes of the genus Setaria. This condition is usually seen in cattle and equines and is of little pathogenic significance, although migration of the worm to the eye may lead to blindness.	0	2	1	0
Filariasis Infections with nematodes of the superfamily FILARIOIDEA. The presence of living worms in the body is mainly asymptomatic but the death of adult worms leads to granulomatous inflammation and permanent fibrosis. Organisms of the genus Elaeophora infect wild elk and domestic sheep causing ischemic necrosis of the brain, blindness, and dermatosis of the face.	0	2	1	0
Infections, Helicobacter [description not available]	0	2	1	0
Helicobacter Infections Infections with organisms of the genus HELICOBACTER, particularly, in humans, HELICOBACTER PYLORI. The clinical manifestations are focused in the stomach, usually the gastric mucosa and antrum, and the upper duodenum. This infection plays a major role in the pathogenesis of type B gastritis and peptic ulcer disease.	0	2	1	0
Auditory Processing Disorder, Central [description not available]	0	2	1	0
Adult Fanconi Syndrome [description not available]	0	2.68	3	0
Glycosuria The appearance of an abnormally large amount of GLUCOSE in the urine, such as more than 500 mg/day in adults. It can be due to HYPERGLYCEMIA or genetic defects in renal reabsorption (RENAL GLYCOSURIA).	0	2	1	0
Proteinuria The presence of proteins in the urine, an indicator of KIDNEY DISEASES.	0	2	1	0
Hypophosphatemia A condition of an abnormally low level of PHOSPHATES in the blood.	0	2	1	0
Psoriasis Arthropathica [description not available]	0	4.7	2	1
Arthritis, Psoriatic A type of inflammatory arthritis associated with PSORIASIS, often involving the axial joints and the peripheral terminal interphalangeal joints. It is characterized by the presence of HLA-B27-associated SPONDYLARTHROPATHY, and the absence of rheumatoid factor.	0	4.7	2	1
Central Nervous System Disease [description not available]	0	2	1	0
Central Nervous System Diseases Diseases of any component of the brain (including the cerebral hemispheres, diencephalon, brain stem, and cerebellum) or the spinal cord.	0	2	1	0
Complications, Pregnancy [description not available]	0	2	1	0
Femur Neck Fractures [description not available]	0	2	1	0
Fracture, Pathologic [description not available]	0	2	1	0
Segond Fracture [description not available]	0	2	1	0
Ankle Injuries Harm or hurt to the ankle or ankle joint usually inflicted by an external source.	0	2	1	0
Femoral Neck Fractures Fractures of the short, constricted portion of the thigh bone between the femur head and the trochanters. It excludes intertrochanteric fractures which are HIP FRACTURES.	0	2	1	0
Tibial Fractures Fractures of the TIBIA.	0	2	1	0
Atrophy, Muscle [description not available]	0	1.97	1	0
Muscular Atrophy Derangement in size and number of muscle fibers occurring with aging, reduction in blood supply, or following immobilization, prolonged weightlessness, malnutrition, and particularly in denervation.	0	1.97	1	0
Heart Disease, Ischemic [description not available]	0	2	1	0
Myocardial Ischemia A disorder of cardiac function caused by insufficient blood flow to the muscle tissue of the heart. The decreased blood flow may be due to narrowing of the coronary arteries (CORONARY ARTERY DISEASE), to obstruction by a thrombus (CORONARY THROMBOSIS), or less commonly, to diffuse narrowing of arterioles and other small vessels within the heart. Severe interruption of the blood supply to the myocardial tissue may result in necrosis of cardiac muscle (MYOCARDIAL INFARCTION).	0	2	1	0
Electron Transport Chain Deficiencies, Mitochondrial [description not available]	0	2.92	1	0
Mitochondrial Diseases Diseases caused by abnormal function of the MITOCHONDRIA. They may be caused by mutations, acquired or inherited, in mitochondrial DNA or in nuclear genes that code for mitochondrial components. They may also be the result of acquired mitochondria dysfunction due to adverse effects of drugs, infections, or other environmental causes.	0	2.92	1	0
Bone Loss, Osteoclastic [description not available]	0	2.01	1	0
Caprine Diseases [description not available]	0	2.01	1	0
Cancer of Esophagus [description not available]	0	1.98	1	0
Neoplasms, Nervous System [description not available]	0	1.98	1	0
Delayed Effects, Prenatal Exposure [description not available]	0	1.98	1	0
Esophageal Neoplasms Tumors or cancer of the ESOPHAGUS.	0	1.98	1	0
Adult Rickets [description not available]	0	1.98	1	0
Osteomalacia Disorder caused by an interruption of the mineralization of organic bone matrix leading to bone softening, bone pain, and weakness. It is the adult form of rickets resulting from disruption of VITAMIN D; PHOSPHORUS; or CALCIUM homeostasis.	0	6.98	1	0
Cerebral Palsy, Athetoid [description not available]	0	1.98	1	0
Deficiency, Mental [description not available]	0	2.38	2	0
Cerebral Palsy A heterogeneous group of nonprogressive motor disorders caused by chronic brain injuries that originate in the prenatal period, perinatal period, or first few years of life. The four major subtypes are spastic, athetoid, ataxic, and mixed cerebral palsy, with spastic forms being the most common. The motor disorder may range from difficulties with fine motor control to severe spasticity (see MUSCLE SPASTICITY) in all limbs. Spastic diplegia (Little disease) is the most common subtype, and is characterized by spasticity that is more prominent in the legs than in the arms. Pathologically, this condition may be associated with LEUKOMALACIA, PERIVENTRICULAR. (From Dev Med Child Neurol 1998 Aug;40(8):520-7)	0	1.98	1	0
Intellectual Disability Subnormal intellectual functioning which originates during the developmental period. This has multiple potential etiologies, including genetic defects and perinatal insults. Intelligence quotient (IQ) scores are commonly used to determine whether an individual has an intellectual disability. IQ scores between 70 and 79 are in the borderline range. Scores below 67 are in the disabled range. (from Joynt, Clinical Neurology, 1992, Ch55, p28)	0	2.38	2	0
Aqueductal Stenosis [description not available]	0	2.89	1	0
Hydramnios [description not available]	0	2.89	1	0
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	0	1.98	1	0
Candida Infection [description not available]	0	1.97	1	0
Candidiasis Infection with a fungus of the genus CANDIDA. It is usually a superficial infection of the moist areas of the body and is generally caused by CANDIDA ALBICANS. (Dorland, 27th ed)	0	1.97	1	0
Pericementitis [description not available]	0	1.97	1	0
Periodontitis Inflammation and loss of connective tissues supporting or surrounding the teeth. This may involve any part of the PERIODONTIUM. Periodontitis is currently classified by disease progression (CHRONIC PERIODONTITIS; AGGRESSIVE PERIODONTITIS) instead of age of onset. (From 1999 International Workshop for a Classification of Periodontal Diseases and Conditions, American Academy of Periodontology)	0	1.97	1	0
Experimental Hepatoma [description not available]	0	2.66	3	0
Abnormalities, Multiple Congenital abnormalities that affect more than one organ or body structure.	0	1.97	1	0
Microcephaly A congenital abnormality in which the CEREBRUM is underdeveloped, the fontanels close prematurely, and, as a result, the head is small. (Desk Reference for Neuroscience, 2nd ed.)	0	1.97	1	0
Anterior Choroidal Artery Infarction [description not available]	0	1.97	1	0
Cerebral Infarction The formation of an area of NECROSIS in the CEREBRUM caused by an insufficiency of arterial or venous blood flow. Infarcts of the cerebrum are generally classified by hemisphere (i.e., left vs. right), lobe (e.g., frontal lobe infarction), arterial distribution (e.g., INFARCTION, ANTERIOR CEREBRAL ARTERY), and etiology (e.g., embolic infarction).	0	1.97	1	0

fumaric acid

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