2,5-hexanedione profile

2,5-hexanedione: metabolite of methyl-n-butyl ketone [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

2,5-hexanedione : A diketone that is hexane substituted by oxo groups at positions 2 and 5. It is a toxic metabolite of hexane and of 2-hexanone [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	8035
CHEMBL ID	1564795
CHEBI ID	85014
SCHEMBL ID	10001
MeSH ID	M0057431

Synonym
nsc7621
acetonyl acetone
.alpha.,.beta.-diacetylethane
wln: 1v2v1
2,5-diketohexane
acetone, acetonyl-
nsc-7621
2,5-hexadione
diacetonyl
1,2-diacetylethane
110-13-4
2,5-hexanedione
2,5-dioxohexane
hexanedione, 2,5-
acetonylacetone
hexane-2,5-dione
inchi=1/c6h10o2/c1-5(7)3-4-6(2)8/h3-4h2,1-2h
NCGC00091466-01
smr000568468
MLS001065580 ,
einecs 203-738-3
ccris 2919
2,5-hexandione
alpha,beta-diacetylethane
nsc 7621
ai3-02399
brn 0506525
2,5-hexanedione, >=98%
H0101
AKOS000119007
A802149
NCGC00091466-02
c0z8884j3p ,
unii-c0z8884j3p
4-01-00-03688 (beilstein handbook reference)
LMFA12000081
tox21_200618
dtxcid6010138
NCGC00258172-01
cas-110-13-4
dtxsid8030138 ,
FT-0621812
acan
acetonylacetone [mi]
BBL027731
SCHEMBL10001
cid_8035
bdbm73981
hexan-2,5-dione
hexan-2,5-dion
acetonylaceton
2,5-hexane-di-one
chebi:85014 ,
CHEMBL1564795
Q-200202
ch3coch2ch2coch3
hexanedione-(2,5)
mfcd00008792
acetonylacetone/2,5-diketohexane
2,5-hexanedione, 97%
F0001-0216
GS-3782
2,5-hexanedione, analytical standard
2,5-hexanedione, puriss. p.a., >=99.0%
D71099
EN300-19144
2,5-hexanedione, vetec(tm) reagent grade, 98%
CS-D1203
Q209264
AMY25528
STL194267
hexan-2

Research Excerpts

Toxicity

Chronic exposure to n-hexane causes sensorimotor neuropathy. Neuropathy is mainly mediated by its toxic metabolite, 2,5-hexanedione (HD) NAC protects against 2, 5-HD neurotoxicity and DMPN may be proposed as a new sensitive and specific biomarker.

Excerpt	Reference	Relevance
" This dose approximates the single dose LD50 (2."	( Further studies on ketone neurotoxicity and interactions. DiVincenzo, GD; Katz, GV; Krasavage, WJ; O'Donoghue, JL, 1984)	0.27
" These observations support the hypothesis that covalent crosslinking of the stable neurofilament is the primary event in the molecular pathogenesis of these toxic neuropathies, and that the rate of crosslinking of neurofilaments determines the proximodistal location of the axonal swelling."	( The effect of 3,4-dimethyl substitution on the neurotoxicity of 2,5-hexanedione. I. Accelerated clinical neuropathy is accompanied by more proximal axonal swellings. Anthony, DC; Boekelheide, K; Graham, DG, 1983)	0.5
" In addition, chloroform was significantly more toxic than deutero-chloroform in hepatocytes from either corn oil- or HD-pretreated rats."	( Potentiation of chlorinated hydrocarbon toxicity by 2,5-hexanedione in primary cultures of adult rat hepatocytes. Harbison, RD; Jernigan, JD; Pounds, JG, )	0.38
"The protective role of zinc against the toxic effects of 2, 5-hexanedione (2,5-HD), the main neurotoxic metabolite of n-hexane, was investigated by studying the interference of zinc on the toxicokinetics of 2,5-HD."	( Evidence for zinc protection against 2,5-hexanedione toxicity by co-exposure of rats to zinc chloride. Batoreu, MC; Mateus, ML; Santos, AP, )	0.4
" These alpha-diketones also display a degree of toxic selectivity towards neuroblastoma cells, which may have therapeutic implications."	( A comparison of the apoptotic and cytotoxic effects of hexanedione derivatives on human non-neuronal lines and the neuroblastoma line SH-SY5Y. Coleman, MD; Griffiths, HR; Woehrling, EK; Zilz, TR, 2008)	0.35
" The toxic effect of this compound was similar in control cells irrespective of the mtDNA background."	( The background of mitochondrial DNA haplogroup J increases the sensitivity of Leber's hereditary optic neuropathy cells to 2,5-hexanedione toxicity. Achilli, A; Barbieri, A; Carelli, V; Ghelli, A; Iommarini, L; Mattioli, S; Pala, M; Porcelli, AM; Rugolo, M; Torroni, A; Vidoni, S; Zanna, C, 2009)	0.56
" Taken together, our findings suggest that at the studied conditions NAC protects against 2,5-HD neurotoxicity and DMPN may be proposed as a new sensitive and specific biomarker of 2,5-HD neurotoxicity in animals treated with a toxic amount of 2,5-hexanedione."	( Role of N-acetylcysteine in protecting against 2,5-hexanedione neurotoxicity in a rat model: changes in urinary pyrroles levels and motor activity performance. Andrade, V; Batoréu, MC; dos Santos, AP; Gonçalves, LL; Mateus, ML; Torres, ME, 2014)	0.84
"Chronic exposure to n-hexane, a widely used solvent in industry, causes sensorimotor neuropathy, which is mainly mediated by its toxic metabolite, 2,5-hexanedione (HD)."	( Glibenclamide attenuates 2,5-hexanedione-induced neurotoxicity in the spinal cord of rats through mitigation of NLRP3 inflammasome activation, neuroinflammation and oxidative stress. Hou, L; Huang, R; Li, S; Wang, Q; Yang, J; Zhang, D; Zhao, J, 2020)	1.06
"Currently, whether nod-like receptor family pyrin domain-containing 3 (NLRP3) inflammasome activation contributes to neuropathy induced by 2,5-Hexanedione (HD), the toxic metabolite of n-hexane, remains unknown."	( NLRP3 inflammasome mediates 2,5-hexanedione-induced neurotoxicity through regulation of macrophage infiltration in rats. Hou, L; Huang, R; Ruan, Z; Sun, W; Wang, Q; Zhang, D, 2020)	1.05
"Chronic exposure to n-hexane causes sensorimotor neuropathy, which is mediated by 2,5-hexanedione (HD), a toxic metabolite of n-hexane."	( 2,5-hexanedione induces NLRP3 inflammasome activation and neurotoxicity through NADPH oxidase-dependent pathway. Hou, L; Huang, R; Ruan, Z; Sun, W; Wang, Q; Zhai, X; Zhang, D; Zhao, X, 2021)	2.29

Pharmacokinetics

Excerpt	Reference	Relevance
"Biological exposure index (BEI) of n-hexane was studied for accuracy using a physiologically based pharmacokinetic (PB-PK) model."	( "Dynamic" biological exposure indexes for n-hexane and 2,5-hexanedione, suggested by a physiologically based pharmacokinetic model. Brugnone, F; Mozzo, P; Olivato, D; Perbellini, L, 1990)	0.53
" 2,5-HD disappeared monoexponentially from the application site with a half-life of 6 hr."	( Disposition, pharmacokinetics, and metabolism of a dermal dose of [14C]2,5-hexanedione in hens. Abou-Donia, MB; Nomeir, AA; Suwita, E, )	0.36
" Many pharmacokinetic processes such as metabolism and absorption can be impacted by the presence of other chemicals in the environment and diet and as a result of medication."	( Pharmacokinetics, chemical interactions, and toxicological risk assessment in perspective. Blancato, JN, 1994)	0.29

Compound-Compound Interactions

Excerpt	Reference	Relevance
"This investigation was designed to study the neurotoxicity produced in hens by the aliphatic hexacarbons n-hexane, methyl n-butyl ketone (MnBK), 2,5-hexanediol (2,5-HDOH), and 2,5-hexanedione (2,5-HD) following daily dermal application of each chemical alone and in combination with O-ethyl O-4-nitrophenyl phenylphosphonothioate (EPN)."	( Pattern of neurotoxicity of n-hexane, methyl n-butyl ketone, 2,5-hexanediol, and 2,5-hexanedione alone and in combination with O-ethyl O-4-nitrophenyl phenylphosphonothioate in hens. Abou-Donia, MB; Campbell, GM; Makkawy, HM, 1985)	0.69

Dosage Studied

Rats were dosed with 2,5-hexanedione (2, 5-HD), acetone, ethanol or combinations of these for 6 weeks. Deaths occurred in all groups of hens given 2,4- Hexanedione before sacrifice at 3 wk. All rats given 2,.5- hexanedione survived a 4-wk study period.

Excerpt	Relevance	Reference
" Therefore, both ACR and 2,5-HD produce a transient and repeated compromise of fast anterograde transport during the dosing regimen which results in distal nerve degeneration."	( Toxic neurofilamentous axonopathies and fast anterograde axonal transport. III. Recovery from single injections and multiple dosing effects of acrylamide and 2,5-hexanedione. Sickles, DW, 1991)	0.48
" Anatomical findings indicate damage to one type of retinal ganglion cell, the large (alpha) or Y-cell class, both during dosing and after a long recovery period."	( Selective damage to large cells in the cat retinogeniculate pathway by 2,5-hexanedione. Eskin, TA; Flood, DG; Merigan, WH; Pasternak, T, 1985)	0.5
" The exact location at which axonal enlargements occur appears to be a continuous function, dependent on both the structure and dosage schedule of the chemical toxin."	( Pathogenesis of experimental giant neurofilamentous axonopathies: a unified hypothesis based on chemical modification of neurofilaments. Autilio-Gambetti, L; Gambetti, P; Sayre, LM, 1985)	0.27
"Rats were dosed with 2,5-hexanedione (2,5-HD), acetone, ethanol or combinations of these for 6 weeks."	( Neurophysiological and behavioural effects of combined exposure to 2,5-hexanedione and acetone or ethanol in rats. Hass, U; Ladefoged, O; Simonsen, L, 1989)	0.83
" Both the extent of this crosslinking and its localization in particular portions of peripheral nerves showed a correlation with HD dosage and with the known progression of ultrastructural features during HD-induced neuropathy."	( 2,5-Hexanedione neuropathy is associated with the covalent crosslinking of neurofilament proteins. Carden, MJ; Lee, VM; Schlaepfer, WW, 1986)	1.71
" Simultaneous dosing with acetone altered the toxicokinetic model which best described the plasma concentration versus time data."	( Acetone-induced changes in the toxicokinetics of 2,5-hexanedione in rabbits. Ladefoged, O; Perbellini, L, 1986)	0.53
" Cessation of dosing resulted in some recovery from clinical neuropathy but virtually no change in histopathologically demonstrable CNS damage."	( Alterations in rat axonal cytoskeletal proteins induced by in vitro and in vivo 2,5-hexanedione exposure. DeCaprio, AP; O'Neill, EA, 1985)	0.5
" Baseline data were collected before dosing started."	( Assessment of the effects of acrylamide, methylmercury, and 2,5-hexanedione on motor functions in mice. Gilbert, SG; Maurissen, JP, 1982)	0.51
" Onset of behavioral deficits appeared after four dosage weeks."	( A neurobehavioral model of 2,5-hexanedione-induced neuropathy. Sheppard, RC; Sterman, AB, )	0.43
" High pressure liquid chromatography (HPLC) permitted the detection of the dicarboxylic acids malonic acid and glutaric acid in the n-nonane dosed rat urines."	( The metabolism of n-nonane in male Fischer 344 rats. Baughman, TM; Bombick, DD; Jarnot, BM; Ketcha, M; Mattie, DR; Serve, MP, 1995)	0.29
" Animals were intoxicated with 2,5-hexanedione by two dosing paradigms: intraperitoneal or oral."	( 2,5-Hexanedione alters elemental composition and water content of rat peripheral nerve myelinated axons. Hussein, SJ; Lehning, EJ; LoPachin, RM; Saubermann, AJ; Stack, EC, 1994)	2.02
" Deaths occurred in all groups of hens given 2,5-hexanedione (75, 105, or 150 mg/kg) before sacrifice at 3 wk, but all rats given 2,5-hexanedione (150, 225, 350 mg/kg) survived a 4-wk study period, even though gait changes were evident in the 225 and 350 mg/kg dosage groups by 3 wk."	( Comparison of toxicities of acrylamide and 2,5-hexanedione in hens and rats on 3-week dosing regimens. Ehrich, M; Jortner, BS, 1993)	0.81
" We employed two differently designed experiments with respect to the dosage levels and treatment periods for developing clinical neuropathies."	( The effects of 2,5-hexanedione and acrylamide on myosin heavy chain isoforms of slow and fast skeletal muscles of the rat. Futatsuka, M; Miyamoto, E; Nagano, M; Oishi, Y; Yamamoto, H, 1996)	0.65
" vs gavage) of intoxication have shown that swelling and degeneration were related to neurotoxicant dosing conditions (i."	( Redefining toxic distal axonopathies. LoPachin, RM, 2000)	0.31
" HD was administered by gavage according to different daily dosing regiments (100, 175, 250, or 400 mg/kg/day) and four proximodistal nerve regions (5th lumbar spinal nerve, proximal and distal sciatic nerve, and tibial nerve) were examined morphometrically."	( gamma-diketone peripheral neuropathy. I. Quality morphometric analyses of axonal atrophy and swelling. Arezzo, JC; Fox, JH; Jortner, BS; Kitano, T; Lehning, EJ; LoPachin, RM, 2000)	0.31
" Therefore, as a possible mechanism of atrophy, NF subunit (NF-L, -M, and -H) proteins were quantitated in moderately affected rats intoxicated with HD at three daily dosing rates (175, 250, and 400 mg/kg/day)."	( gamma-diketone peripheral neuropathy. II. Neurofilament subunit content. Chiu, FC; He, DK; Lehning, EJ; LoPachin, RM; Opanashuk, LA, 2000)	0.31
" To investigate the mechanism of diminished NF content, subunit (NF-L, -M and -H) gene expression was quantified in dorsal root ganglion (DRG) of slightly affected and moderately intoxicated groups of rats exposed to 2,5-hexanedione (HD) at one of three daily dosing rates (175, 250 and 400 mg/kg per day)."	( Gamma-diketone peripheral neuropathy III. Neurofilament gene expression. He, DK; Lehning, EJ; LoPachin, RM; Opanashuk, LA, 2001)	0.5
" To evaluate this possibility, groups of rats were exposed to HD at dosing schedules (175 mg/kg x 101 days or 400 mg/kg x 26 days) that produced moderate levels of neurological deficits and prevalent axon atrophy in spinal cord white matter tracts."	( 2,5-Hexanedione-induced changes in the monomeric neurofilament protein content of rat spinal cord fractions. He, D; LoPachin, RM; Opanashuk, LA; Reid, ML, 2004)	1.77
" To determine the effects of HD on the stationary and mobile NF pools, groups of rats were exposed to HD at dosing schedules (175 mg/kg x 101 days or 400 mg/kg x 26 days) that produced moderate levels of neurological deficits and, as assessed by previous studies, prevalent axon atrophy in peripheral nerve."	( 2,5-Hexanedione-induced changes in the neurofilament subunit pools of rat peripheral nerve. He, D; LoPachin, RM; Reid, ML, 2005)	1.77
" HD was administrated to Wistar rats by intraperitoneal injection at dosage of 200 or 400 mg/kg/day (five-times per week)."	( 2,5-Hexanedione induced decrease in cytoskeletal proteins of rat sciatic-tibial nerve. Han, X; Xie, K; Yu, L; Zhang, C; Zhang, T; Zhao, X; Zhu, Z, 2005)	1.77
" The above changes of gene expression were detectable within a short period after the dosing prior to the appearance of obvious pathological changes."	( Effects of male reproductive toxicants on gene expression in rat testes. Fukushima, T; Hamada, Y; Horii, I; Kikkawa, R; Komiyama, M; Mori, C; Yamamoto, T, 2005)	0.33
"To investigate the mechanisms of the axonopathy induced by 2,5-hexanedione (2,5-HD), male Wistar rats were administered at a dosage of 400 mg/kg/day 2,5-HD (five times per week)."	( Time-dependent alteration of cytoskeletal proteins in cerebral cortex of rat during 2,5-hexanedione-induced neuropathy. Song, F; Xie, K; Yu, L; Yu, S; Zhang, C; Zhao, X, 2007)	0.81
" Male adult Wistar rats were administered by intraperitoneal injection at a dosage of 200 or 400 mg/kg HD, five days per week for 8 weeks."	( Expression of Bcl-2, Bax and Caspase-3 in nerve tissues of rats chronically exposed to 2,5-hexanedione. Cui, N; Li, S; Xie, K; Yu, L; Zhang, C; Zhang, T; Zhao, X; Zhu, Z, 2007)	0.56
" The present study investigates dose-response relationships for these classic Sertoli cell toxicants using histopathology endpoints."	( Dose-dependent effects of sertoli cell toxicants 2,5-hexanedione, carbendazim, and mono-(2-ethylhexyl) phthalate in adult rat testis. Boekelheide, K; Bryant, BH; Hall, SJ; Moffit, JS, 2007)	0.59
"To investigate the reversibility of the neuropathy induced by 2,5-HD, adult male rats were administered at a dosage of 400 mg/kg/day 2,5-HD (five times per week) for 2, 4, and 8 weeks, respectively."	( The reversibility of neurofilaments decline induced by 2,5-hexanedione in rat nerve tissues. Song, F; Wang, Q; Xie, K; Yu, S; Zhang, C; Zhou, G, 2008)	0.59
"To investigate the mechanisms and biomarker of the neuropathy induced by 2,5-hexanedione (HD), male Wistar rats were administrated HD at dosage of 200 or 400mg/kg for 8 weeks (five-times per week)."	( Changes of cytoskeletal proteins in nerve tissues and serum of rats treated with 2,5-hexanedione. Hou, LY; Song, FY; Wang, QS; Xie, KQ; Zhang, CL, 2008)	0.8
"Male Wistar rats were administered at a dosage of 400 mg/kg/day 2, 5-HD for 2, 4 and 8 weeks respectively."	( [Dynamic study of neurofilament contents in rat's spinal cord induced by 2, 5-hexanedione]. Song, FY; Wang, QS; Xie, KQ; Yu, LH; Zeng, T; Zhu, ZP, 2008)	0.35
" To investigate the change of NFs degradation and their possible role in n-hexane neuropathy, adult male Wistar rats were administered intraperitoneally at a dosage of 400 mg/kg/day 2,5-hexanedione (2,5-HD) for 4 weeks."	( 2,5-hexanedione altered the degradation of low-molecular-weight neurofilament in rat nerve tissues. Gao, Y; Kou, R; Song, F; Xie, K; Zhang, Q; Zou, C, 2012)	2.01
"Dose-dependent effects were observed between the dosage of n-hexane and 2, 5-hexanedione, and pyrrole adducts in tissues."	( Correlation between levels of 2, 5-hexanedione and pyrrole adducts in tissues of rats exposure to n-hexane for 5-days. Guo, Y; Xie, K; Yin, H; Zeng, T; Zhao, X, 2013)	0.39
" Dose-response studies using adult male Fischer 344 rats subchronically exposed to model Sertoli cell toxicants (0."	( From the Cover: Sperm Molecular Biomarkers Are Sensitive Indicators of Testicular Injury following Subchronic Model Toxicant Exposure. Anderson, LM; Boekelheide, K; Dere, E; Wilson, SK, 2016)	0.43
" Results showed that the increased pyrrole adducts in hair, urine and serum accumulated in dose-response relationship."	( Hair pyrrole adducts serve as biomarkers for peripheral nerve impairment induced by 2,5-hexanedione and n-hexane in rats. Li, M; Li, X; Wang, Q; Wang, S; Xie, K; Zhang, C, 2018)	0.71
"Nine-week old SPF male Wistar rats were administered at daily dosing of 100 and 300 mg/kg by intraperitoneal injection for continuous 8 weeks(five times every week)."	( [Effects of 2, 5-hexanedione on S100β of Schwann cells in rat sciatic nerves]. Cheng, D; Guo, J; Li, H; Yan, Y; Yang, F; Yao, W; Zhang, T; Zhou, W, 2020)	0.56

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

Role	Description
human xenobiotic metabolite	Any human metabolite produced by metabolism of a xenobiotic compound in humans.
neurotoxin	A poison that interferes with the functions of the nervous system.
[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
diketone	A compound that contains two ketone functionalities.
methyl ketone	A ketone of formula RC(=O)CH3 (R =/= H).
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASE	Homo sapiens (human)	Potency	0.0562	0.0032	45.4673	12,589.2998	AID2517
RAR-related orphan receptor gamma	Mus musculus (house mouse)	Potency	3.5880	0.0060	38.0041	19,952.5996	AID1159521; AID1159523
aldehyde dehydrogenase 1 family, member A1	Homo sapiens (human)	Potency	22.3872	0.0112	12.4002	100.0000	AID1030
retinoic acid nuclear receptor alpha variant 1	Homo sapiens (human)	Potency	35.2872	0.0030	41.6115	22,387.1992	AID1159552
retinoid X nuclear receptor alpha	Homo sapiens (human)	Potency	22.4678	0.0008	17.5051	59.3239	AID1159527
67.9K protein	Vaccinia virus	Potency	8.8006	0.0001	8.4406	100.0000	AID720579; AID720580
thyroid stimulating hormone receptor	Homo sapiens (human)	Potency	55.9264	0.0016	28.0151	77.1139	AID1259385
Nuclear receptor ROR-gamma	Homo sapiens (human)	Potency	0.3758	0.0266	22.4482	66.8242	AID651802
[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)
ORF73	Human gammaherpesvirus 8	EC50 (µMol)	75.0000	0.0600	8.1346	32.1400	AID435023
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
negative regulation of transcription by RNA polymerase II	Nuclear receptor ROR-gamma	Homo sapiens (human)
xenobiotic metabolic process	Nuclear receptor ROR-gamma	Homo sapiens (human)
regulation of glucose metabolic process	Nuclear receptor ROR-gamma	Homo sapiens (human)
regulation of steroid metabolic process	Nuclear receptor ROR-gamma	Homo sapiens (human)
intracellular receptor signaling pathway	Nuclear receptor ROR-gamma	Homo sapiens (human)
circadian regulation of gene expression	Nuclear receptor ROR-gamma	Homo sapiens (human)
cellular response to sterol	Nuclear receptor ROR-gamma	Homo sapiens (human)
positive regulation of circadian rhythm	Nuclear receptor ROR-gamma	Homo sapiens (human)
regulation of fat cell differentiation	Nuclear receptor ROR-gamma	Homo sapiens (human)
positive regulation of DNA-templated transcription	Nuclear receptor ROR-gamma	Homo sapiens (human)
adipose tissue development	Nuclear receptor ROR-gamma	Homo sapiens (human)
T-helper 17 cell differentiation	Nuclear receptor ROR-gamma	Homo sapiens (human)
regulation of transcription by RNA polymerase II	Nuclear receptor ROR-gamma	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
RNA polymerase II cis-regulatory region sequence-specific DNA binding	Nuclear receptor ROR-gamma	Homo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specific	Nuclear receptor ROR-gamma	Homo sapiens (human)
DNA-binding transcription repressor activity, RNA polymerase II-specific	Nuclear receptor ROR-gamma	Homo sapiens (human)
DNA-binding transcription factor activity	Nuclear receptor ROR-gamma	Homo sapiens (human)
protein binding	Nuclear receptor ROR-gamma	Homo sapiens (human)
oxysterol binding	Nuclear receptor ROR-gamma	Homo sapiens (human)
zinc ion binding	Nuclear receptor ROR-gamma	Homo sapiens (human)
ligand-activated transcription factor activity	Nuclear receptor ROR-gamma	Homo sapiens (human)
sequence-specific double-stranded DNA binding	Nuclear receptor ROR-gamma	Homo sapiens (human)
nuclear receptor activity	Nuclear receptor ROR-gamma	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
nucleus	Nuclear receptor ROR-gamma	Homo sapiens (human)
nucleoplasm	Nuclear receptor ROR-gamma	Homo sapiens (human)
nuclear body	Nuclear receptor ROR-gamma	Homo sapiens (human)
chromatin	Nuclear receptor ROR-gamma	Homo sapiens (human)
nucleus	Nuclear receptor ROR-gamma	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Assay ID	Title	Year	Journal	Article
AID1745845	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.
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.
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.
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.
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	132 (31.73)	18.7374
1990's	132 (31.73)	18.2507
2000's	79 (18.99)	29.6817
2010's	59 (14.18)	24.3611
2020's	14 (3.37)	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	3 (0.66%)	5.53%
Reviews	17 (3.72%)	6.00%
Case Studies	1 (0.22%)	4.05%
Observational	0 (0.00%)	0.25%
Other	436 (95.40%)	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
aminolevulinic acid Aminolevulinic Acid: A compound produced from succinyl-CoA and GLYCINE as an intermediate in heme synthesis. It is used as a PHOTOCHEMOTHERAPY for actinic KERATOSIS.. 5-aminolevulinic acid : The simplest delta-amino acid in which the hydrogens at the gamma position are replaced by an oxo group. It is metabolised to protoporphyrin IX, a photoactive compound which accumulates in the skin. Used (in the form of the hydrochloride salt)in combination with blue light illumination for the treatment of minimally to moderately thick actinic keratosis of the face or scalp.	1.99	1	0	4-oxo monocarboxylic acid; amino acid zwitterion; delta-amino acid	antineoplastic agent; dermatologic drug; Escherichia coli metabolite; human metabolite; mouse metabolite; photosensitizing agent; plant metabolite; prodrug; Saccharomyces cerevisiae metabolite
acetic acid Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.	7.25	1	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).	3.85	12	0	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
beta-alanine [no description available]	7.03	1	0	amino acid zwitterion; beta-amino acid	agonist; fundamental metabolite; human metabolite; inhibitor; neurotransmitter
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.	1.99	1	0	benzoic acids	algal metabolite; antimicrobial food preservative; drug allergen; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; human xenobiotic metabolite; plant metabolite
benzyl alcohol Benzyl Alcohol: A colorless liquid with a sharp burning taste and slight odor. It is used as a local anesthetic and to reduce pain associated with LIDOCAINE injection. Also, it is used in the manufacture of other benzyl compounds, as a pharmaceutic aid, and in perfumery and flavoring.. hydroxytoluene : Any member of the class of toluenes carrying one or more hydroxy substituents.. benzyl alcohol : An aromatic alcohol that consists of benzene bearing a single hydroxymethyl substituent.. aromatic alcohol : Any alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.. aromatic primary alcohol : Any primary alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.	2	1	0	benzyl alcohols	antioxidant; fragrance; metabolite; solvent
carbamates [no description available]	3.44	7	0	amino-acid anion
formic acid formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.	2.13	1	0	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
2-cresol 2-cresol: RN given refers to parent cpd. o-cresol : A cresol that is phenol substituted by a methyl group at position 2. It is a minor urinary metabolite of toluene.	2.05	1	0	cresol	human xenobiotic 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.	3.09	5	0	N-acylglycine	human blood serum metabolite; uremic toxin
3,4-dihydroxyphenylacetic acid 3,4-Dihydroxyphenylacetic Acid: A deaminated metabolite of LEVODOPA.. (3,4-dihydroxyphenyl)acetic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine.. dihydroxyphenylacetic acid : A dihydroxy monocarboxylic acid consisting of phenylacetic acid having two phenolic hydroxy substituents.	1.98	1	0	catechols; dihydroxyphenylacetic acid	human metabolite
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	2.39	2	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
diacetyl butane-2,3-dione : An alpha-diketone that is butane substituted by oxo groups at positions 2 and 3. It is a metabolite produced during the malolactic fermentation.	1.96	1	0	alpha-diketone	Escherichia coli 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.	1.99	1	0	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
glycine [no description available]	7.03	1	0	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical
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.	2.1	1	0	metal allergen; nickel group element atom	epitope; micronutrient
pyridoxamine [no description available]	2.02	1	0	aminoalkylpyridine; hydroxymethylpyridine; monohydroxypyridine; vitamin B6	Escherichia coli metabolite; human metabolite; iron chelator; mouse metabolite; nephroprotective agent; plant metabolite; Saccharomyces cerevisiae metabolite
pyridoxine 4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol: structure in first source. vitamin B6 : Any member of the group of pyridines that exhibit biological activity against vitamin B6 deficiency. Vitamin B6 deficiency is associated with microcytic anemia, electroencephalographic abnormalities, dermatitis with cheilosis (scaling on the lips and cracks at the corners of the mouth) and glossitis (swollen tongue), depression and confusion, and weakened immune function. Vitamin B6 consists of the vitamers pyridoxine, pyridoxal, and pyridoxamine and their respective 5'-phosphate esters (and includes their corresponding ionized and salt forms).	1.96	1	0	hydroxymethylpyridine; methylpyridines; monohydroxypyridine; vitamin B6	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
taurine [no description available]	7.15	1	0	amino sulfonic acid; zwitterion	antioxidant; Escherichia coli metabolite; glycine receptor agonist; human metabolite; mouse metabolite; nutrient; radical scavenger; Saccharomyces cerevisiae metabolite
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	4	14	0	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
urea pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.	2.66	3	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
mandelic acid SAMMA: mandelic acid condensation polymer	2.69	3	0	2-hydroxy monocarboxylic acid; benzenes	antibacterial agent; human xenobiotic metabolite
pyrithione pyrithione: split from cephalosporin molecule; some metal complexes of this have fumarate reductase inhibitory activity and may be useful against trypanosomes; RN given refers to parent cpd; structure. pyrithione : A pyridinethione that is pyridine-2(1H)-thione in which the hydrogen attached to the nitrogen is replaced by a hydroxy group. It is a Zn(2+) ionophore; the zinc salt is used as an antifungal and antibacterial agent.	1.98	1	0	monohydroxypyridine; pyridinethione	ionophore
homovanillic acid Homovanillic Acid: A 3-O-methyl ETHER of (3,4-dihydroxyphenyl)acetic acid.. homovanillate : A hydroxy monocarboxylic acid anion which is obtained by deprotonation of the carboxy group of homovanillic acid.. homovanillic acid : A monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite.	2.38	2	0	guaiacols; monocarboxylic acid	human metabolite; mouse metabolite
hydroxyindoleacetic acid (5-hydroxyindol-3-yl)acetic acid : A member of the class of indole-3-acetic acids that is indole-3-acetic acid substituted by a hydroxy group at C-5.	1.97	1	0	indole-3-acetic acids	drug metabolite; human metabolite; mouse metabolite
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.	3.09	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
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.	1.95	1	0	N-acylglycine	Daphnia magna metabolite
clioquinol Clioquinol: A potentially neurotoxic 8-hydroxyquinoline derivative long used as a topical anti-infective, intestinal antiamebic, and vaginal trichomonacide. The oral preparation has been shown to cause subacute myelo-optic neuropathy and has been banned worldwide.. 5-chloro-7-iodoquinolin-8-ol : A monohydroxyquinoline that is quinolin-8-ol in which the hydrogens at positions 5 and 7 are replaced by chlorine and iodine, respectively. It has antibacterial and atifungal properties, and is used in creams for the treatment of skin infections. It has also been investigated as a chelator of copper and zinc ions for the possible treatment of Alzheimer's disease.	6.96	1	0	monohydroxyquinoline; organochlorine compound; organoiodine compound	antibacterial agent; antifungal agent; antimicrobial agent; antineoplastic agent; antiprotozoal drug; chelator; copper chelator
diazepam Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.	1.96	1	0	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; xenobiotic
dibutyl phthalate Dibutyl Phthalate: A plasticizer used in most plastics and found in water, air, soil, plants and animals. It may have some adverse effects with long-term exposure.. dibutyl phthalate : A phthalate ester that is the diester obtained by the formal condensation of the carboxy groups of phthalic acid with two molecules of butan-1-ol. Although used extensively as a plasticiser, it is a ubiquitous environmental contaminant that poses a risk to humans.	2.08	1	0	diester; phthalate ester	EC 3.2.1.20 (alpha-glucosidase) inhibitor; environmental contaminant; metabolite; plasticiser; teratogenic agent
ether Ether: A mobile, very volatile, highly flammable liquid used as an inhalation anesthetic and as a solvent for waxes, fats, oils, perfumes, alkaloids, and gums. It is mildly irritating to skin and mucous membranes.. ether : An organooxygen compound with formula ROR, where R is not hydrogen.. diethyl ether : An ether in which the oxygen atom is linked to two ethyl groups.	2	1	0	ether; volatile organic compound	inhalation anaesthetic; non-polar solvent; refrigerant
glutaral Glutaral: One of the protein CROSS-LINKING REAGENTS that is used as a disinfectant for sterilization of heat-sensitive equipment and as a laboratory reagent, especially as a fixative.. glutaraldehyde : A dialdehyde comprised of pentane with aldehyde functions at C-1 and C-5.	2.38	2	0	dialdehyde	cross-linking reagent; disinfectant; fixative
glyburide Glyburide: An antidiabetic sulfonylurea derivative with actions like those of chlorpropamide. glyburide : An N-sulfonylurea that is acetohexamide in which the acetyl group is replaced by a 2-(5-chloro-2-methoxybenzamido)ethyl group.	2.66	2	0	monochlorobenzenes; N-sulfonylurea	anti-arrhythmia drug; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor; hypoglycemic agent
halothane [no description available]	3.09	1	0	haloalkane; organobromine compound; organochlorine compound; organofluorine compound	inhalation anaesthetic
hexachlorophene Hexachlorophene: A chlorinated bisphenol antiseptic with a bacteriostatic action against Gram-positive organisms, but much less effective against Gram-negative organisms. It is mainly used in soaps and creams and is an ingredient of various preparations used for skin disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p797). hexachlorophene : An organochlorine compound that is diphenylmethane in which each of the phenyl groups is substituted by chlorines at positions 2, 3, and 5, and by a hydroxy group at position 6. An antiseptic that is effective against Gram-positive organisms, it is used in soaps and creams for the treatment of various skin disorders. It is also used in agriculture as an acaricide and fungicide, but is not approved for such use within the European Union.	7.08	1	0	bridged diphenyl fungicide; polyphenol; trichlorobenzene	acaricide; antibacterial agent; antifungal agrochemical; antiseptic drug
isoniazid Hydra: A genus of freshwater polyps in the family Hydridae, order Hydroida, class HYDROZOA. They are of special interest because of their complex organization and because their adult organization corresponds roughly to the gastrula of higher animals.. hydrazide : Compounds derived from oxoacids RkE(=O)l(OH)m (l =/= 0) by replacing -OH by -NRNR2 (R groups are commonly H). (IUPAC).	1.95	1	0	carbohydrazide	antitubercular agent; drug allergen
2-propanol 2-Propanol: An isomer of 1-PROPANOL. It is a colorless liquid having disinfectant properties. It is used in the manufacture of acetone and its derivatives and as a solvent. Topically, it is used as an antiseptic.. propan-2-ol : A secondary alcohol that is propane in which one of the hydrogens attached to the central carbon is substituted by a hydroxy group.	2	1	0	secondary alcohol; secondary fatty alcohol	protic solvent
methoxyamine methoxyamine: analytical reagent for aldehydes and ketones; strong irritant, can probably produce methemoglobinemia; RN given refers to parent cpd; structure	1.97	1	0	organooxygen compound
phenobarbital Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.	2.38	2	0	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
phenylmethylsulfonyl fluoride Phenylmethylsulfonyl Fluoride: An enzyme inhibitor that inactivates IRC-50 arvin, subtilisin, and the fatty acid synthetase complex.. phenylmethanesulfonyl fluoride : An acyl fluoride with phenylmethanesulfonyl as the acyl group.	1.98	1	0	acyl fluoride	serine proteinase inhibitor
proadifen Proadifen: An inhibitor of drug metabolism and CYTOCHROME P-450 ENZYME SYSTEM activity.	1.97	1	0	diarylmethane
salicylamide salamide: a major impurity of hydrochlorothiazide; structure in first source	2.1	1	0	phenols; salicylamides	antirheumatic drug; non-narcotic analgesic
iodoacetic acid Iodoacetic Acid: A derivative of ACETIC ACID that contains one IODINE atom attached to its methyl group.. iodoacetic acid : A haloacetic acid that is acetic acid in which one of the hydrogens of the methyl group is replaced by an iodine atom.	1.96	1	0	haloacetic acid; organoiodine compound	alkylating agent
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.	2.02	1	0
tremorine [no description available]	1.96	1	0	N-alkylpyrrolidine
thymidine [no description available]	1.96	1	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
penicillamine Penicillamine: 3-Mercapto-D-valine. The most characteristic degradation product of the penicillin antibiotics. It is used as an antirheumatic and as a chelating agent in Wilson's disease.. penicillamine : An alpha-amino acid having the structure of valine substituted at the beta position with a sulfanyl group.	7.39	2	0	non-proteinogenic alpha-amino acid; penicillamine	antirheumatic drug; chelator; copper chelator; drug allergen
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.	1.97	1	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
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.	8.07	5	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
ethinyl estradiol Ethinyl Estradiol: A semisynthetic alkylated ESTRADIOL with a 17-alpha-ethinyl substitution. It has high estrogenic potency when administered orally, and is often used as the estrogenic component in ORAL CONTRACEPTIVES.. 17alpha-ethynylestradiol : A 3-hydroxy steroid that is estradiol substituted by a ethynyl group at position 17. It is a xenoestrogen synthesized from estradiol and has been shown to exhibit high estrogenic potency on oral administration.	2.08	1	0	17-hydroxy steroid; 3-hydroxy steroid; terminal acetylenic compound	xenoestrogen
leucine Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.	2.37	2	0	amino acid zwitterion; L-alpha-amino acid; leucine; proteinogenic amino acid; pyruvate family amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
uridine triphosphate Uridine Triphosphate: Uridine 5'-(tetrahydrogen triphosphate). A uracil nucleotide containing three phosphate groups esterified to the sugar moiety.	1.99	1	0	pyrimidine ribonucleoside 5'-triphosphate; uridine 5'-phosphate	Escherichia coli metabolite; mouse metabolite
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.	1.96	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
colchicine (S)-colchicine : A colchicine that has (S)-configuration. It is a secondary metabolite, has anti-inflammatory properties and is used to treat gout, crystal-induced joint inflammation, familial Mediterranean fever, and many other conditions.	2.89	4	0	alkaloid; colchicine	anti-inflammatory agent; gout suppressant; mutagen
chloroform Chloroform: A commonly used laboratory solvent. It was previously used as an anesthetic, but was banned from use in the U.S. due to its suspected carcinogenicity.. chloroform : A one-carbon compound that is methane in which three of the hydrogens are replaced by chlorines.	7.66	3	0	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
dimethylformamide Dimethylformamide: A formamide in which the amino hydrogens are replaced by methyl groups.. N,N-dimethylformamide : A member of the class of formamides that is formamide in which the amino hydrogens are replaced by methyl groups.	1.99	1	0	formamides; volatile organic compound	geroprotector; hepatotoxic agent; polar aprotic solvent
threonine Threonine: An essential amino acid occurring naturally in the L-form, which is the active form. It is found in eggs, milk, gelatin, and other proteins.. threonine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 1-hydroxyethyl group.	2.04	1	0	amino acid zwitterion; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid; threonine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	1.98	1	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
carbon disulfide Carbon Disulfide: A colorless, flammable, poisonous liquid, CS2. It is used as a solvent, and is a counterirritant and has local anesthetic properties but is not used as such. It is highly toxic with pronounced CNS, hematologic, and dermatologic effects.	7.67	3	0	one-carbon compound; organosulfur compound
trichloroacetic acid Trichloroacetic Acid: A strong acid used as a protein precipitant in clinical chemistry and also as a caustic for removing warts.. trichloroacetic acid : A monocarboxylic acid that is acetic acid in which all three methyl hydrogens are substituted by chlorine.	1.99	1	0	monocarboxylic acid; organochlorine compound	carcinogenic agent; metabolite; mouse metabolite
trifluoroacetic acid Trifluoroacetic Acid: A very strong halogenated derivative of acetic acid. It is used in acid catalyzed reactions, especially those where an ester is cleaved in peptide synthesis.. trifluoroacetic acid : A monocarboxylic acid that is the trifluoro derivative of acetic acid.	2.01	1	0	fluoroalkanoic acid	human xenobiotic metabolite; NMR chemical shift reference compound; reagent
tri-o-cresyl phosphate tri-o-cresyl phosphate: see also related IMOL S-140	1.97	1	0
methylethyl ketone methylethyl ketone: solvent; colorless synthetic resins, smokeless powders; may be irritating to eyes, mucous membranes; may be toxic in high concentrations; structure. butanone : Any ketone that is butane substituted by an oxo group at unspecified position.. butan-2-one : A dialkyl ketone that is a four-carbon ketone carrying a single keto- group at position C-2.	3.85	12	0	butanone; dialkyl ketone; methyl ketone; volatile organic compound	bacterial metabolite; polar aprotic solvent
propionamide [no description available]	2	1	0	monocarboxylic acid amide; primary fatty amide
acrylamide [no description available]	6.07	23	0	acrylamides; N-acylammonia; primary carboxamide	alkylating agent; carcinogenic agent; Maillard reaction product; mutagen; neurotoxin
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.	2.58	2	0	aldehyde; furans	Maillard reaction product; metabolite
4-(dimethylamino)benzaldehyde p-dimethylaminobenzaldehyde: structure in first source. 4-(dimethylamino)benzaldehyde : A member of the class of benzaldehydes that is benzaldehyde carrying a dimethylamino substituent at position 4. Used as an indicator for detection of indoles and hydrazine.	2.41	2	0	benzaldehydes; substituted aniline; tertiary amino compound	chromogenic compound
styrene Styrene: A colorless, toxic liquid with a strong aromatic odor. It is used to make rubbers, polymers and copolymers, and polystyrene plastics.. styrene : A vinylarene that is benzene carrying a vinyl group. It has been isolated from the benzoin resin produced by Styrax species.	3.78	3	0	styrenes; vinylarene; volatile organic compound	mouse metabolite; mutagen; plant metabolite
allyl chloride [no description available]	6.98	1	0	organochlorine compound
sarin Sarin: An organophosphorus ester compound that produces potent and irreversible inhibition of cholinesterase. It is toxic to the nervous system and is a chemical warfare agent.. isopropyl methylphosphonofluoridate : A phosphinic ester that is the isopropyl ester of methylphosphonofluoridic acid.. sarin : A racemate composed of equal amounts of (R)- and (S)-sarin. A potent and irreversible inhibitor of acetylcholinesterase that is toxic to the nervous system and is employed as a chemical warfare agent.	2.01	1	0	fluorine molecular entity; phosphinic ester
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	10.56	95	3	alkane
methyl isobutyl ketone [no description available]	2.38	2	0	ketone
gamma-valerolactone gamma-valerolactone: metabolite of n-hexane; RN given refers to cpd with methyl moiety in position 5. gamma-valerolactone : A butan-4-olide that is dihydrofuran-2(3H)-one substituted by a methyl group at position 5. It has been found in the urine samples of humans exposed to n-hexane.	2.36	2	0	butan-4-olide	flavouring agent; human xenobiotic metabolite
cyclohexanol Cyclohexanols: Monohydroxy derivatives of cyclohexanes that contain the general formula R-C6H11O. They have a camphorlike odor and are used in making soaps, insecticides, germicides, dry cleaning, and plasticizers.. cyclohexanols : An alcohol in which one or more hydroxy groups are attached to a cyclohexane skeleton.	2	1	0	cyclohexanols; secondary alcohol	solvent
pentane Pentanes: Five-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives.. pentane : A straight chain alkane consisting of 5 carbon atoms.	2	1	0	alkane; volatile organic compound	non-polar solvent; refrigerant
methyl cellosolve methyl cellosolve: widely used industrial solvent for resins, lacquers, dyes & inks; may cause anemia macrocytosis, appearance of young granulocytes in blood; RN given refers to parent cpd	2.02	1	0	glycol ether	protic solvent; solvent
pyrroles 1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.	7.9	36	1	pyrrole; secondary amine
n-hexane hexane : An unbranched alkane containing six carbon atoms.	10.26	86	3	alkane; volatile organic compound	neurotoxin; non-polar solvent
1,2-dimethoxyethane 1,2-dimethoxyethane: RN given refers to cpd with specified locants for methoxy moieties. 1,2-dimethoxyethane : A diether that is the 1,2-dimethyl ether of ethane-1,2-diol.	2	1	0	diether	non-polar solvent
1-hexanol 1-hexanol: RN given refers to parent cpd. hexanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of six carbon atoms.. hexan-1-ol : A primary alcohol that is hexane substituted by a hydroxy group at position 1.	3.36	7	0	hexanol; primary alcohol	alarm pheromone; antibacterial agent; fragrance; plant metabolite
1,5-pentanediol [no description available]	2	1	0	primary alcohol
nonane iotrochotin: toxin from the Caribbean sponge Iotrochota birotulata, which selectively permeabilizes synaptosomes. nonane : A straight chain alkane composed of 9 carbon atoms.	1.98	1	0	alkane	plant metabolite; volatile oil component
3,3'-iminodipropionitrile 3,3'-iminodipropionitrile: lathyrogen; RN refers to parent cpd; blocks axoplasmic transport of neurofilament proteins with subsequent axon swelling typical of some motor neuron diseases	4.45	7	0
diethylhexyl phthalate Diethylhexyl Phthalate: An ester of phthalic acid. It appears as a light-colored, odorless liquid and is used as a plasticizer for many resins and elastomers.. bis(2-ethylhexyl) phthalate : A phthalate ester that is the bis(2-ethylhexyl) ester of benzene-1,2-dicarboxylic acid.	2.42	2	0	diester; phthalate ester	androstane receptor agonist; apoptosis inhibitor; plasticiser
1,2-diethylbenzene [no description available]	7.1	1	0
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	2.39	2	0	acetate ester; ethyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; metabolite; polar aprotic solvent; Saccharomyces cerevisiae metabolite
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).	8.37	1	1	alkane; volatile organic compound	non-polar solvent; plant metabolite
ditiocarb Ditiocarb: A chelating agent that has been used to mobilize toxic metals from the tissues of humans and experimental animals. It is the main metabolite of DISULFIRAM.. diethyldithiocarbamic acid : A member of the class of dithiocarbamic acids that is diethylcarbamic acid in which both of the oxygens are replaced by sulfur.	1.99	1	0	dithiocarbamic acids	chelator; copper chelator
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	1.98	1	0	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
thiazoles [no description available]	2.47	2	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
hydrazine diamine : Any polyamine that contains two amino groups.	1.98	1	0	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
evans blue Evans Blue: An azo dye used in blood volume and cardiac output measurement by the dye dilution method. It is very soluble, strongly bound to plasma albumin, and disappears very slowly.. Evans blue : An organic sodium salt that is the tetrasodium salt of 6,6'-{(3,3'-dimethyl[1,1'-biphenyl]-4,4'-diyl)bis[diazene-2,1-diyl]}bis(4-amino-5-hydroxynaphthalene-1,3-disulfonate). It is sometimes used as a counterstain, especially in fluorescent methods to suppress background autofluorescence.	2.05	1	0	organic sodium salt	fluorochrome; histological dye; sodium channel blocker; teratogenic agent
lithocholic acid Lithocholic Acid: A bile acid formed from chenodeoxycholate by bacterial action, usually conjugated with glycine or taurine. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as cholagogue and choleretic.. lithocholic acid : A monohydroxy-5beta-cholanic acid with a alpha-hydroxy substituent at position 3. It is a bile acid obtained from chenodeoxycholic acid by bacterial action.. lithocholate : A bile acid anion that is the conjugate base of lithocholic acid.	1.96	1	0	bile acid; C24-steroid; monohydroxy-5beta-cholanic acid	geroprotector; human metabolite; mouse metabolite
cyanogen bromide Cyanogen Bromide: Cyanogen bromide (CNBr). A compound used in molecular biology to digest some proteins and as a coupling reagent for phosphoroamidate or pyrophosphate internucleotide bonds in DNA duplexes.	1.99	1	0
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	2.79	3	0	dialdehyde	biomarker
methyl n-butyl ketone Methyl n-Butyl Ketone: An industrial solvent which causes nervous system degeneration. MBK is an acronym often used to refer to it.. hexanone : A ketone that is a hexane carrying an oxo substituent at unspecified position.	5.82	18	0	ketone
allyl sulfide allyl sulfide: essence of garlic; inhibits CYP2E1	2.77	3	0	organic sulfide
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	7.52	2	0	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
2,5-dimethylpyrrole 2,5-dimethylpyrrole: structure given in first source	2.68	3	0	pyrroles
2,5-dimethylfuran 2,5-dimethylfuran: metabolite of n-hexane. 2,5-dimethylfuran : A member of the class of furans that is furan in which the hydrogens at positions 2 and 5 are replaced by methyl groups.	2.36	2	0	furans	antifungal agent; bacterial metabolite; fuel; fumigant; human urinary metabolite; Maillard reaction product; plant metabolite
2-hexanol hexan-2-ol : A hexanol in which the hydroxy group is at position 2.	3.08	5	0	hexanol; secondary alcohol	human metabolite; plant metabolite; semiochemical
hexamethylene glycol hexane-1,6-diol : A diol that is hexane substituted by hydroxy groups at positions 1 and 6.	1.95	1	0	diol; primary alcohol
undecane undecane : A straight-chain alkane with 11 carbon atoms.	1.99	1	0	alkane
2-acetylfuran 2-acetylfuran : A furan carrying an acetyl substituent at the 2-position. Used in the production of the antibiotic cefuroxime (CHEBI:3515).	7.38	2	0	aromatic ketone; furans; methyl ketone
digoxigenin Digoxigenin: 3 beta,12 beta,14-Trihydroxy-5 beta-card-20(22)-enolide. A cardenolide which is the aglycon of digoxin. Can be obtained by hydrolysis of digoxin or from Digitalis orientalis L. and Digitalis lanata Ehrh.. digoxigenin : A hydroxy steroid that consists of 5beta-cardanolide having a double bond at the 20(22)-position as well as hydroxy groups at the 3beta-, 12beta- and 14beta-positions. It has been isolated from the plant species of the genus Digitalis.	1.99	1	0	12beta-hydroxy steroid; 14beta-hydroxy steroid; 3beta-hydroxy steroid; 3beta-sterol	hapten; plant metabolite
pimozide Pimozide: A diphenylbutylpiperidine that is effective as an antipsychotic agent and as an alternative to HALOPERIDOL for the suppression of vocal and motor tics in patients with Tourette syndrome. Although the precise mechanism of action is unknown, blockade of postsynaptic dopamine receptors has been postulated. (From AMA Drug Evaluations Annual, 1994, p403). pimozide : A member of the class of benzimidazoles that is 1,3-dihydro-2H-benzimidazol-2-one in which one of the nitrogens is substituted by a piperidin-4-yl group, which in turn is substituted on the nitrogen by a 4,4-bis(p-fluorophenyl)butyl group.	2.03	1	0	benzimidazoles; heteroarylpiperidine; organofluorine compound	antidyskinesia agent; dopaminergic antagonist; first generation antipsychotic; H1-receptor antagonist; serotonergic antagonist
phenylphosphonothioic acid, 2-ethyl 2-(4-nitrophenyl) ester Phenylphosphonothioic Acid, 2-Ethyl 2-(4-Nitrophenyl) Ester: An organothiophosphorus cholinesterase inhibitor that is used as an insecticide and as a acaricide.	2.37	2	0	organic phosphonate; organothiophosphate insecticide; phosphonic ester	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor
fucose Fucose: A six-member ring deoxysugar with the chemical formula C6H12O5. It lacks a hydroxyl group on the carbon at position 6 of the molecule.. L-fucopyranose : The pyranose form of L-fucose.. fucose : Any deoxygalactose that is deoxygenated at the 6-position.	1.96	1	0	fucopyranose; L-fucose	Escherichia coli metabolite; mouse metabolite
2,5-hexanediol hexane-2,5-diol : A glycol that is hexane substituted by hydroxy groups at positions 2 and 5.	3.21	6	0	glycol; secondary alcohol
dithiothreitol 1,4-dimercaptobutane-2,3-diol : A glycol that is butane-2,3-diol in which a hydrogen from each of the methyl groups is replaced by a thiol group.. 1,4-dithiothreitol : The threo-diastereomer of 1,4-dimercaptobutane-2,3-diol.	1.97	1	0	1,4-dimercaptobutane-2,3-diol; butanediols; dithiol; glycol; thiol	chelator; human metabolite; reducing agent
2,3-hexanedione hexane-2,3-dione : An alpha-diketone that is hexane substituted by oxo groups at positions 2 and 3 respectively.	2.69	3	0	alpha-diketone	metabolite
mono-(2-ethylhexyl)phthalate mono-(2-ethylhexyl)phthalate: RN given refers to parent cpd. mono(2-ethylhexyl) phthalate : The mono(2-ethylhexyl) ester of benzene-1,2-dicarboxylic acid.	2.42	2	0	phthalic acid monoester
ethylene dimethanesulfonate ethylene dimethanesulfonate: antispermatogenic agent; structure	2.08	1	0
norleucine Norleucine: An unnatural amino acid that is used experimentally to study protein structure and function. It is structurally similar to METHIONINE, however it does not contain SULFUR.. L-norleucine : A non-proteinogenic L-alpha-amino acid comprising hexanoic acid carrying an amino group at C-2. It does not occur naturally.	2.1	1	0	2-aminohexanoic acid; L-alpha-amino acid zwitterion; non-proteinogenic L-alpha-amino acid
iridium Iridium: A metallic element with the atomic symbol Ir, atomic number 77, and atomic weight 192.22.	2.13	1	0	cobalt group element atom; platinum group metal atom
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	1.97	1	0	dihydrogen
carbendazim carbendazim: carcinogen when combined with sodium nitrite; principle metabolite of thiophanate methyl & benomyl; structure. carbendazim : A member of the class of benzimidazoles that is 2-aminobenzimidazole in which the primary amino group is substituted by a methoxycarbonyl group. A fungicide, carbendazim controls Ascomycetes, Fungi Imperfecti, and Basidiomycetes on a wide variety of crops, including bananas, cereals, cotton, fruits, grapes, mushrooms, ornamentals, peanuts, sugarbeet, soybeans, tobacco, and vegetables.	3.44	7	0	benzimidazole fungicide; benzimidazoles; benzimidazolylcarbamate fungicide; carbamate ester	antifungal agrochemical; antinematodal drug; metabolite; microtubule-destabilising agent
ethionine L-ethionine : An S-ethylhomocysteine that has S-configuration at the chiral centre.	7.08	1	0	S-ethylhomocysteine	antimetabolite; carcinogenic agent
misonidazole Misonidazole: A nitroimidazole that sensitizes normally radio-resistant hypoxic cells to radiation. It may also be directly cytotoxic to hypoxic cells and has been proposed as an antineoplastic.	1.95	1	0
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.	1.99	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
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	3.22	6	0	benzenes; phenyl acetates
methylformamide N-methylformamide : A member of the class of formamides having a N-methyl substituent.	7.39	2	0	formamides
acetylacetone acetylacetone : A beta-diketone that is pentane in which the hydrogens at positions 2 and 4 are replaced by oxo groups.	1.96	1	0	beta-diketone
tetrachloroethylene Tetrachloroethylene: A chlorinated hydrocarbon used as an industrial solvent and cooling liquid in electrical transformers. It is a potential carcinogen.	1.97	1	0	chlorocarbon; chloroethenes	nephrotoxic agent
transferrin Transferrin: An iron-binding beta1-globulin that is synthesized in the LIVER and secreted into the blood. It plays a central role in the transport of IRON throughout the circulation. A variety of transferrin isoforms exist in humans, including some that are considered markers for specific disease states.	1.98	1	0
3,4-dimethyl-2,5-hexanedione [no description available]	10.52	13	0
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	2.4	2	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
1,2-diacetylbenzene [no description available]	7.75	3	0
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	2.01	1	0	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
thiazolyl blue thiazolyl blue: RN & II refers to bromide. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide : The bromide salt of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium.	2.47	2	0	organic bromide salt	colorimetric reagent; dye
2,4-hexanedione [no description available]	2.88	4	0
dansyl hydrazine [no description available]	1.98	1	0
4-bromophenylacetylurea 4-bromophenylacetylurea: structure	2.37	2	0
florox reagent Florox Reagent: reagent for analysis of ketosteroids; structure	1.97	1	0
5,5'-bis(8-(phenylamino)-1-naphthalenesulfonate) [no description available]	1.97	1	0
4-oxopentanal 4-oxopentanal: an indoor pollutant; structure in first source. 4-oxopentanal : A ketoaldehyde that is pentanal substituted by an oxo group at position 4.	2.02	1	0	ketoaldehyde	metabolite
atropine tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate : A tropane alkaloid that is (1R,5)-8-methyl-8-azabicyclo[3.2.1]octane substituted by a (3-hydroxy-2-phenylpropanoyl)oxy group at position 3.	6.98	1	0
5-hydroxymethylfurfural 5-hydroxymethylfurfural: has antisickling activity; HMF is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo. 5-hydroxymethylfurfural : A member of the class of furans that is furan which is substituted at positions 2 and 5 by formyl and hydroxymethyl substituents, respectively. Virtually absent from fresh foods, it is naturally generated in sugar-containing foods during storage, and especially by drying or cooking. It is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo.	2.58	2	0	arenecarbaldehyde; furans; primary alcohol	indicator; Maillard reaction product
mevalonic acid Mevalonic Acid: A dihydroxy monocarboxylic acid and precursor in the biosynthetic pathway known as the mevalonate pathway, which produces terpenes and steroids that are vital for diverse cellular functions.. mevalonic acid : A racemate composed of equimolar amounts of (R)- and (S)-mevalonic acid.. (R)-mevalonic acid : The (R)-enantiomer of mevalonic acid.	1.95	1	0	3,5-dihydroxy-3-methylpentanoic acid
ouabain Ouabain: A cardioactive glycoside consisting of rhamnose and ouabagenin, obtained from the seeds of Strophanthus gratus and other plants of the Apocynaceae; used like DIGITALIS. It is commonly used in cell biological studies as an inhibitor of the NA(+)-K(+)-EXCHANGING ATPASE.. cardiac glycoside : Steroid lactones containing sugar residues that act on the contractile force of the cardiac muscles.. ouabain : A steroid hormone that is a multi-hydroxylated alpha-L-rhamnosyl cardenoloide. It binds to and inhibits the plasma membrane Na(+)/K(+)-ATPase (sodium pump). It has been isolated naturally from Strophanthus gratus.	1.99	1	0	11alpha-hydroxy steroid; 14beta-hydroxy steroid; 5beta-hydroxy steroid; alpha-L-rhamnoside; cardenolide glycoside; steroid hormone	anti-arrhythmia drug; cardiotonic drug; EC 2.3.3.1 [citrate (Si)-synthase] inhibitor; EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; ion transport inhibitor; plant metabolite
taurolithocholic acid Taurolithocholic Acid: A bile salt formed in the liver from lithocholic acid conjugation with taurine, usually as the sodium salt. It solubilizes fats for absorption and is itself absorbed. It is a cholagogue and choleretic.. taurolithocholic acid : The bile acid taurine conjugate of lithocholic acid.	1.96	1	0	bile acid taurine conjugate; monocarboxylic acid amide	human metabolite
n-formylmethionine leucyl-phenylalanine N-Formylmethionine Leucyl-Phenylalanine: A formylated tripeptide originally isolated from bacterial filtrates that is positively chemotactic to polymorphonuclear leucocytes, and causes them to release lysosomal enzymes and become metabolically activated.. N-formyl-L-methionyl-L-leucyl-L-phenylalanine : A tripeptide composed of L-Met, L-Leu and L-Phe in a linear sequence with a formyl group at the amino terminus. It acts as a potent inducer of leucocyte chemotaxis and macrophage activator as well as a ligand for the FPR receptor.	3.37	1	1	tripeptide
ergosterol [no description available]	2.05	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; ergostanoid; phytosterols	fungal metabolite; Saccharomyces cerevisiae metabolite
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	7.44	2	0	resveratrol	antioxidant; phytoalexin; plant metabolite; quorum sensing inhibitor; radical scavenger
thapsigargin Thapsigargin: A sesquiterpene lactone found in roots of THAPSIA. It inhibits SARCOPLASMIC RETICULUM CALCIUM-TRANSPORTING ATPASES.. thapsigargin : An organic heterotricyclic compound that is a hexa-oxygenated 6,7-guaianolide isolated fron the roots of Thapsia garganica L., Apiaceae. A potent skin irritant, it is used in traditional medicine as a counter-irritant. Thapsigargin inhibits Ca(2+)-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum and is used in experimentation examining the impacts of increasing cytosolic calcium concentrations.	1.99	1	0	butyrate ester; organic heterotricyclic compound; sesquiterpene lactone	calcium channel blocker; EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor
diethylstilbestrol Diethylstilbestrol: A synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen. (Merck, 11th ed). diethylstilbestrol : An olefinic compound that is trans-hex-3-ene in which the hydrogens at positions 3 and 4 have been replaced by p-hydroxyphenyl groups.	7.04	1	0	olefinic compound; polyphenol	antifungal agent; antineoplastic agent; autophagy inducer; calcium channel blocker; carcinogenic agent; EC 1.1.1.146 (11beta-hydroxysteroid dehydrogenase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; endocrine disruptor; xenoestrogen
bromochloroacetic acid Keratins: A class of fibrous proteins or scleroproteins that represents the principal constituent of EPIDERMIS; HAIR; NAILS; horny tissues, and the organic matrix of tooth ENAMEL. Two major conformational groups have been characterized, alpha-keratin, whose peptide backbone forms a coiled-coil alpha helical structure consisting of TYPE I KERATIN and a TYPE II KERATIN, and beta-keratin, whose backbone forms a zigzag or pleated sheet structure. alpha-Keratins have been classified into at least 20 subtypes. In addition multiple isoforms of subtypes have been found which may be due to GENE DUPLICATION.. bromochloroacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by bromine while a second is replaced by chlorine. A low-melting (27.5-31.5degreeC), hygroscopic crystalline solid, it can be formed during the disinfection (by chlorination) of water that contains bromide ions and organic matter, so can occur in drinking water as a byproduct of the disinfection process.	2.66	3	0	2-bromocarboxylic acid; monocarboxylic acid; organochlorine compound
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	2.44	2	0	stilbene
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.	2.04	1	0	alpha,beta-unsaturated monocarboxylic acid; sorbic acid
leuprolide Leuprolide: A potent synthetic long-acting agonist of GONADOTROPIN-RELEASING HORMONE that regulates the synthesis and release of pituitary gonadotropins, LUTEINIZING HORMONE and FOLLICLE STIMULATING HORMONE.. leuprolide : An oligopeptide comprising pyroglutamyl, histidyl, tryptophyl, seryl, tyrosyl, D-leucyl, leucyl, arginyl, and N-ethylprolinamide residues joined in sequence. It is a synthetic nonapeptide analogue of gonadotropin-releasing hormone, and is used as a subcutaneous hydrogel implant (particularly as the acetate salt) for the treatment of prostate cancer and for the suppression of gonadal sex hormone production in children with central precocious puberty.	8.5	2	0	oligopeptide	anti-estrogen; antineoplastic agent; gonadotropin releasing hormone agonist
thiourea Thiourea: A photographic fixative used also in the manufacture of resins. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance may reasonably be anticipated to be a carcinogen (Merck Index, 9th ed). Many of its derivatives are ANTITHYROID AGENTS and/or FREE RADICAL SCAVENGERS.. thiourea : The simplest member of the thiourea class, consisting of urea with the oxygen atom substituted by sulfur.	1.96	1	0	one-carbon compound; thioureas; ureas	antioxidant; chromophore
nadp [no description available]	2.05	1	0
2,4-dithiobiuret 2,4-dithiobiuret: structure	6.96	1	0
sodium dodecyl sulfate Sodium Dodecyl Sulfate: An anionic surfactant, usually a mixture of sodium alkyl sulfates, mainly the lauryl; lowers surface tension of aqueous solutions; used as fat emulsifier, wetting agent, detergent in cosmetics, pharmaceuticals and toothpastes; also as research tool in protein biochemistry.. sodium dodecyl sulfate : An organic sodium salt that is the sodium salt of dodecyl hydrogen sulfate.	1.97	1	0	organic sodium salt	detergent; protein denaturant
mtt formazan MTT formazan: a blue MEM-insoluble mitochondrial byproduct; used to determine viability of cells with active mitochondrial dehydrogenase enzymes	2.44	2	0
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.	1.97	1	0
4-hydroxy-2-nonenal 4-hydroxy-2-nonenal: cytotoxic product from peroxidation of liver microsomal lipids; RN given refers to cpd without isomeric designation. 4-hydroxynon-2-enal : An enal consisting of non-2-ene having an oxo group at the 1-position and a hydroxy group at the 4-position.. 4-hydroxynonenal : A monounsaturated fatty aldehyde that is nonanal that has undergone dehydrogenation to introduce a double bond at any position in the aliphatic chain and in which a hydrogen at position 4 has been replaced by a hydroxy group.	2	1	0	4-hydroxynon-2-enal; 4-hydroxynonenal
naloxone Naloxone: A specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors.. naloxone : A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.	1.96	1	0	morphinane alkaloid; organic heteropentacyclic compound; tertiary alcohol	antidote to opioid poisoning; central nervous system depressant; mu-opioid receptor antagonist
sirolimus Sirolimus: A macrolide compound obtained from Streptomyces hygroscopicus that acts by selectively blocking the transcriptional activation of cytokines thereby inhibiting cytokine production. It is bioactive only when bound to IMMUNOPHILINS. Sirolimus is a potent immunosuppressant and possesses both antifungal and antineoplastic properties.. sirolimus : A macrolide lactam isolated from Streptomyces hygroscopicus consisting of a 29-membered ring containing 4 trans double bonds, three of which are conjugated. It is an antibiotic, immunosupressive and antineoplastic agent.	2.17	1	0	antibiotic antifungal drug; cyclic acetal; cyclic ketone; ether; macrolide lactam; organic heterotricyclic compound; secondary alcohol	antibacterial drug; anticoronaviral agent; antineoplastic agent; bacterial metabolite; geroprotector; immunosuppressive agent; mTOR inhibitor
brefeldin a [no description available]	1.98	1	0	macrolide antibiotic	Penicillium metabolite
lysophosphatidylcholines lysophosphatidylcholine : An acylglycerophosphocholine resulting from partial hydrolysis of a phosphatidylcholine, which removes one of the fatty acyl groups. The structure is depicted in the image where R1 = acyl, R2 = H or where R1 = H, R2 = acyl.	1.96	1	0	1-O-acyl-sn-glycero-3-phosphocholine
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	1.99	1	0	carbon group element atom; elemental lead; metal atom	neurotoxin
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.	2.04	1	0	muconic acid	biomarker; human xenobiotic metabolite
nitrofurazone Nitrofurazone: A topical anti-infective agent effective against gram-negative and gram-positive bacteria. It is used for superficial WOUNDS AND INJURIES and skin infections. Nitrofurazone has also been administered orally in the treatment of TRYPANOSOMIASIS.. nitrofurazone : A semicarbazone resulting from the formal condensation of semicarbazide with 5-nitrofuraldehyde. A broad spectrum antibacterial drug, although with little activity against Pseudomonas species, it is used as a local application for burns, ulcers, wounds and skin infections.	7.08	1	0
tetrodotoxin Tetrodotoxin: An aminoperhydroquinazoline poison found mainly in the liver and ovaries of fishes in the order TETRAODONTIFORMES, which are eaten. The toxin causes paresthesia and paralysis through interference with neuromuscular conduction.. tetrodotoxin : A quinazoline alkaloid that is a marine toxin isolated from fish such as puffer fish. It has been shown to exhibit potential neutotoxicity due to its ability to block voltage-gated sodium channels.	1.98	1	0	azatetracycloalkane; oxatetracycloalkane; quinazoline alkaloid	animal metabolite; bacterial metabolite; marine metabolite; neurotoxin; voltage-gated sodium channel blocker
triethyllead triethyllead: RN given refers to parent cpd	6.97	1	0
formazans Formazans: Colored azo compounds formed by the reduction of tetrazolium salts. Employing this reaction, oxidoreductase activity can be determined quantitatively in tissue sections by allowing the enzymes to act on their specific substrates in the presence of tetrazolium salts.	2.44	2	0
acid phosphatase Acid Phosphatase: An enzyme that catalyzes the conversion of an orthophosphoric monoester and water to an alcohol and orthophosphate. EC 3.1.3.2.	1.96	1	0
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.	2.57	2	0
calpain Calpain: Cysteine proteinase found in many tissues. Hydrolyzes a variety of endogenous proteins including NEUROPEPTIDES; CYTOSKELETAL PROTEINS; proteins from SMOOTH MUSCLE; CARDIAC MUSCLE; liver; platelets; and erythrocytes. Two subclasses having high and low calcium sensitivity are known. Removes Z-discs and M-lines from myofibrils. Activates phosphorylase kinase and cyclic nucleotide-independent protein kinase. This enzyme was formerly listed as EC 3.4.22.4.	7	1	0
s-nitro-n-acetylpenicillamine S-nitro-N-acetylpenicillamine: a NO donor	2.03	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.	1.96	1	0
mk 2206 MK 2206: a protein kinase inhibitor and antineoplastic agent	2.13	1	0	organic heterotricyclic compound	EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor
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.	1.96	1	0	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
vitamin b 12 Vitamin B 12: A cobalt-containing coordination compound produced by intestinal micro-organisms and found also in soil and water. Higher plants do not concentrate vitamin B 12 from the soil and so are a poor source of the substance as compared with animal tissues. INTRINSIC FACTOR is important for the assimilation of vitamin B 12.	1.96	1	0
angiogenin angiogenin: human tumor protein which stimulates growth of blood vessels; contains 123 amino acids; member of the pancreatic ribonuclease superfamily; MW 14,400	2.11	1	0
cyclic gmp Cyclic GMP: Guanosine cyclic 3',5'-(hydrogen phosphate). A guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger. Its levels increase in response to a variety of hormones, including acetylcholine, insulin, and oxytocin and it has been found to activate specific protein kinases. (From Merck Index, 11th ed). 3',5'-cyclic GMP : A 3',5'-cyclic purine nucleotide in which the purine nucleobase is specified as guanidine.	7.43	2	0	3',5'-cyclic purine nucleotide; guanyl ribonucleotide	Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
guanosine triphosphate Guanosine Triphosphate: Guanosine 5'-(tetrahydrogen triphosphate). A guanine nucleotide containing three phosphate groups esterified to the sugar moiety.	1.97	1	0	guanosine 5'-phosphate; purine ribonucleoside 5'-triphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor
guanosine ribonucleoside : Any nucleoside where the sugar component is D-ribose.	2.01	1	0	guanosines; purines D-ribonucleoside	fundamental metabolite

Condition	Relationship Strength	Studies	Trials
Innate Inflammatory Response [description not available]	2.05	1	0
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	2.05	1	0
Autosomal Dominant Juvenile Parkinson Disease [description not available]	2.25	1	0
Idiopathic Parkinson Disease [description not available]	2.25	1	0
Parkinson Disease A progressive, degenerative neurologic disease characterized by a TREMOR that is maximal at rest, retropulsion (i.e. a tendency to fall backwards), rigidity, stooped posture, slowness of voluntary movements, and a masklike facial expression. Pathologic features include loss of melanin containing neurons in the substantia nigra and other pigmented nuclei of the brainstem. LEWY BODIES are present in the substantia nigra and locus coeruleus but may also be found in a related condition (LEWY BODY DISEASE, DIFFUSE) characterized by dementia in combination with varying degrees of parkinsonism. (Adams et al., Principles of Neurology, 6th ed, p1059, pp1067-75)	2.25	1	0
Parkinsonian Disorders A group of disorders which feature impaired motor control characterized by bradykinesia, MUSCLE RIGIDITY; TREMOR; and postural instability. Parkinsonian diseases are generally divided into primary parkinsonism (see PARKINSON DISEASE), secondary parkinsonism (see PARKINSON DISEASE, SECONDARY) and inherited forms. These conditions are associated with dysfunction of dopaminergic or closely related motor integration neuronal pathways in the BASAL GANGLIA.	2.25	1	0
Encephalopathy, Toxic [description not available]	4.77	11	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	5.2	49	0
Degenerative Diseases, Central Nervous System [description not available]	2.5	2	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.	2.5	2	0
Peripheral Nerve Diseases [description not available]	6.35	28	0
Peripheral Nervous System Diseases Diseases of the peripheral nerves external to the brain and spinal cord, which includes diseases of the nerve roots, ganglia, plexi, autonomic nerves, sensory nerves, and motor nerves.	6.35	28	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	7.46	2	0
Central Nervous System Disease [description not available]	3.03	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.	3.03	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)	3.39	7	0
Asymmetric Diabetic Proximal Motor Neuropathy [description not available]	2.42	2	0
Nerve Pain [description not available]	2.13	1	0
Diabetic Neuropathies Peripheral, autonomic, and cranial nerve disorders that are associated with DIABETES MELLITUS. These conditions usually result from diabetic microvascular injury involving small blood vessels that supply nerves (VASA NERVORUM). Relatively common conditions which may be associated with diabetic neuropathy include third nerve palsy (see OCULOMOTOR NERVE DISEASES); MONONEUROPATHY; mononeuropathy multiplex; diabetic amyotrophy; a painful POLYNEUROPATHY; autonomic neuropathy; and thoracoabdominal neuropathy. (From Adams et al., Principles of Neurology, 6th ed, p1325)	2.42	2	0
Neuralgia Intense or aching pain that occurs along the course or distribution of a peripheral or cranial nerve.	2.13	1	0
Alcohol Drinking Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.	2.13	1	0
Injuries, Spinal Cord [description not available]	2.13	1	0
Spinal Cord Injuries Penetrating and non-penetrating injuries to the spinal cord resulting from traumatic external forces (e.g., WOUNDS, GUNSHOT; WHIPLASH INJURIES; etc.).	2.13	1	0
Ambulation Disorders, Neurologic [description not available]	2.04	1	0
Gait Disorders, Animal [description not available]	2.44	2	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	4.81	5	0
Myelopathy [description not available]	2.72	3	0
Spinal Cord Diseases Pathologic conditions which feature SPINAL CORD damage or dysfunction, including disorders involving the meninges and perimeningeal spaces surrounding the spinal cord. Traumatic injuries, vascular diseases, infections, and inflammatory/autoimmune processes may affect the spinal cord.	2.72	3	0
Hereditary Optic Neuroretinopathy [description not available]	2.05	1	0
Optic Atrophy, Hereditary, Leber A maternally linked genetic disorder that presents in mid-life as acute or subacute central vision loss leading to central scotoma and blindness. The disease has been associated with missense mutations in the mtDNA, in genes for Complex I, III, and IV polypeptides, that can act autonomously or in association with each other to cause the disease. (from Online Mendelian Inheritance in Man, http://www.ncbi.nlm.nih.gov/Omim/, MIM#535000 (April 17, 2001))	2.05	1	0
Polyneuropathy, Acquired [description not available]	3.33	2	0
Polyneuropathies Diseases of multiple peripheral nerves simultaneously. Polyneuropathies usually are characterized by symmetrical, bilateral distal motor and sensory impairment with a graded increase in severity distally. The pathological processes affecting peripheral nerves include degeneration of the axon, myelin or both. The various forms of polyneuropathy are categorized by the type of nerve affected (e.g., sensory, motor, or autonomic), by the distribution of nerve injury (e.g., distal vs. proximal), by nerve component primarily affected (e.g., demyelinating vs. axonal), by etiology, or by pattern of inheritance.	3.33	2	0
Nervous System Disorders [description not available]	7.87	25	1
Nervous System Diseases Diseases of the central and peripheral nervous system. This includes disorders of the brain, spinal cord, cranial nerves, peripheral nerves, nerve roots, autonomic nervous system, neuromuscular junction, and muscle.	7.87	25	1
Testicular Diseases Pathological processes of the TESTIS.	4	5	0
Nerve Degeneration Loss of functional activity and trophic degeneration of nerve axons and their terminal arborizations following the destruction of their cells of origin or interruption of their continuity with these cells. The pathology is characteristic of neurodegenerative diseases. Often the process of nerve degeneration is studied in research on neuroanatomical localization and correlation of the neurophysiology of neural pathways.	3.92	13	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.	5.21	19	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)	3.25	6	0
Adenocarcinoma, Basal Cell [description not available]	2.04	1	0
Breast Cancer [description not available]	2.4	2	0
Cancer of Colon [description not available]	2.04	1	0
Hepatocellular Carcinoma [description not available]	2.04	1	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	2.04	1	0
Breast Neoplasms Tumors or cancer of the human BREAST.	2.4	2	0
Colonic Neoplasms Tumors or cancer of the COLON.	2.04	1	0
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	2.04	1	0
Chemical Dependence [description not available]	2.39	2	0
Substance-Related Disorders Disorders related to substance use or abuse.	2.39	2	0
Diseases, Occupational [description not available]	4.86	8	0
Muscle Contraction A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.	2.37	2	0
Amyotonia Congenita [description not available]	2.65	3	0
Neuromuscular Diseases A general term encompassing lower MOTOR NEURON DISEASE; PERIPHERAL NERVOUS SYSTEM DISEASES; and certain MUSCULAR DISEASES. Manifestations include MUSCLE WEAKNESS; FASCICULATION; muscle ATROPHY; SPASM; MYOKYMIA; MUSCLE HYPERTONIA, myalgias, and MUSCLE HYPOTONIA.	2.65	3	0
Wallerian Degeneration Degeneration of distal aspects of a nerve axon following injury to the cell body or proximal portion of the axon. The process is characterized by fragmentation of the axon and its MYELIN SHEATH.	1.96	1	0
Allodynia [description not available]	1.96	1	0
Hyperesthesia Increased sensitivity to cutaneous stimulation due to a diminished threshold or an increased response to stimuli.	1.96	1	0
Ache [description not available]	2.37	2	0
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	2.37	2	0
Clinically Isolated CNS Demyelinating Syndrome [description not available]	2.36	2	0
Demyelinating Diseases Diseases characterized by loss or dysfunction of myelin in the central or peripheral nervous system.	2.36	2	0
Acute Liver Injury, Drug-Induced [description not available]	3.29	2	0
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	1.95	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.	3.29	2	0
Aneuploid [description not available]	1.98	1	0
Chromosome Deletion Actual loss of portion of a chromosome.	1.98	1	0
Intradural-Extramedullary Spinal Cord Neoplasms [description not available]	1.98	1	0
Spinal Cord Neoplasms Benign and malignant neoplasms which occur within the substance of the spinal cord (intramedullary neoplasms) or in the space between the dura and spinal cord (intradural extramedullary neoplasms). The majority of intramedullary spinal tumors are primary CNS neoplasms including ASTROCYTOMA; EPENDYMOMA; and LIPOMA. Intramedullary neoplasms are often associated with SYRINGOMYELIA. The most frequent histologic types of intradural-extramedullary tumors are MENINGIOMA and NEUROFIBROMA.	1.98	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)	1.98	1	0
Alloxan Diabetes [description not available]	2.38	2	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	2.67	3	0
Poisoning Used with drugs, chemicals, and industrial materials for human or animal poisoning, acute or chronic, whether the poisoning is accidental, occupational, suicidal, by medication error, or by environmental exposure.	8.31	2	0
Ataxia Impairment of the ability to perform smoothly coordinated voluntary movements. This condition may affect the limbs, trunk, eyes, pharynx, larynx, and other structures. Ataxia may result from impaired sensory or motor function. Sensory ataxia may result from posterior column injury or PERIPHERAL NERVE DISEASES. Motor ataxia may be associated with CEREBELLAR DISEASES; CEREBRAL CORTEX diseases; THALAMIC DISEASES; BASAL GANGLIA DISEASES; injury to the RED NUCLEUS; and other conditions.	2.89	4	0
Hyperglycemia, Postprandial Abnormally high BLOOD GLUCOSE level after a meal.	1.98	1	0
Hyperglycemia Abnormally high BLOOD GLUCOSE level.	6.98	1	0
Weight Gain Increase in BODY WEIGHT over existing weight.	1.98	1	0
Palsy [description not available]	2.38	2	0
Paralysis A general term most often used to describe severe or complete loss of muscle strength due to motor system disease from the level of the cerebral cortex to the muscle fiber. This term may also occasionally refer to a loss of sensory function. (From Adams et al., Principles of Neurology, 6th ed, p45)	2.38	2	0
Anoxemia [description not available]	1.99	1	0
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	1.99	1	0
Age-Related Memory Disorders [description not available]	2.01	1	0
Memory Disorders Disturbances in registering an impression, in the retention of an acquired impression, or in the recall of an impression. Memory impairments are associated with DEMENTIA; CRANIOCEREBRAL TRAUMA; ENCEPHALITIS; ALCOHOLISM (see also ALCOHOL AMNESTIC DISORDER); SCHIZOPHRENIA; and other conditions.	2.01	1	0
Poisoning, Lead [description not available]	2.01	1	0
Lead Poisoning Poisoning that results from chronic or acute ingestion, injection, inhalation, or skin absorption of LEAD or lead compounds.	2.01	1	0
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	2.38	2	0
Anaplastic Astrocytoma [description not available]	1.98	1	0
Benign Cerebellar Neoplasms [description not available]	1.98	1	0
Astrocytoma Neoplasms of the brain and spinal cord derived from glial cells which vary from histologically benign forms to highly anaplastic and malignant tumors. Fibrillary astrocytomas are the most common type and may be classified in order of increasing malignancy (grades I through IV). In the first two decades of life, astrocytomas tend to originate in the cerebellar hemispheres; in adults, they most frequently arise in the cerebrum and frequently undergo malignant transformation. (From Devita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2013-7; Holland et al., Cancer Medicine, 3d ed, p1082)	1.98	1	0
Abdominal Cryptorchidism [description not available]	1.98	1	0
Axon Reaction [description not available]	1.98	1	0
Atherosclerotic Parkinsonism [description not available]	1.97	1	0
Parkinson Disease, Secondary Conditions which feature clinical manifestations resembling primary Parkinson disease that are caused by a known or suspected condition. Examples include parkinsonism caused by vascular injury, drugs, trauma, toxin exposure, neoplasms, infections and degenerative or hereditary conditions. Clinical features may include bradykinesia, rigidity, parkinsonian gait, and masked facies. In general, tremor is less prominent in secondary parkinsonism than in the primary form. (From Joynt, Clinical Neurology, 1998, Ch38, pp39-42)	1.97	1	0
Sterility, Male [description not available]	1.97	1	0
Infertility, Male The inability of the male to effect FERTILIZATION of an OVUM after a specified period of unprotected intercourse. Male sterility is permanent infertility.	1.97	1	0
Vision, Diminished [description not available]	1.97	1	0
Malignant Melanoma [description not available]	2.37	2	0
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	2.37	2	0
Bile Duct Obstruction [description not available]	1.96	1	0
Cholestasis Impairment of bile flow due to obstruction in small bile ducts (INTRAHEPATIC CHOLESTASIS) or obstruction in large bile ducts (EXTRAHEPATIC CHOLESTASIS).	1.96	1	0

2,5-hexanedione

Description

Cross-References

Synonyms (72)

Research Excerpts

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Dosage Studied

Roles (2)

Drug Classes (2)

Protein Targets (9)

Potency Measurements

Activation Measurements

Biological Processes (13)

Molecular Functions (10)

Ceullar Components (4)

Bioassays (13)

Research

Studies (416)

Market Indicators

Research Demand Index: 39.91

Study Types

2,5-hexanedione

Description

Cross-References

Synonyms (72)

Research Excerpts

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Dosage Studied

Roles (2)

Drug Classes (2)

Protein Targets (9)

Potency Measurements

Activation Measurements

Biological Processes (13)

Molecular Functions (10)

Ceullar Components (4)

Bioassays (13)

Research

Studies (416)

Market Indicators

Research Demand Index: 39.91

Study Types

Related Drugs (179)

Related Conditions (97)