benzimidazole profile

Benzimidazole is a heterocyclic aromatic organic compound with the formula C7H6N2. It is a white solid that is soluble in most organic solvents. Benzimidazole is an important building block in many pharmaceuticals, including antifungal agents, antiparasitic drugs, and anti-cancer agents. Benzimidazole derivatives are also used as dyes, pigments, and antioxidants. The structure of benzimidazole can be viewed as a benzene ring fused with an imidazole ring. The imidazole ring in benzimidazole is weakly basic and readily undergoes reactions with electrophiles. The most common synthetic route to benzimidazole derivatives involves the condensation of o-phenylenediamine with a carboxylic acid or a carboxylic acid derivative. Benzimidazoles have been studied for their medicinal properties for many years. For example, mebendazole and albendazole are benzimidazole derivatives that are used to treat parasitic infections. The anti-cancer drug tirapazamine is also a benzimidazole derivative. The importance of benzimidazoles in medicinal chemistry lies in their ability to bind to a variety of biological targets. Benzimidazoles are known to interact with DNA, proteins, and enzymes. These interactions can lead to a variety of biological effects, including inhibition of cell growth, modulation of immune function, and anti-inflammatory activity.'

1H-benzimidazole : The 1H-tautomer of benzimidazole. [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	5798
CHEMBL ID	306226
CHEBI ID	41275
CHEBI ID	36622
SCHEMBL ID	5197771
SCHEMBL ID	6010
SCHEMBL ID	6009
MeSH ID	M0097720

Synonym
MLS001066336
smr000471839
ai3-03737
hsdb 2797
brn 0109682
einecs 200-081-4
ccris 5967
bdbm7939
1h-1,3-benzodiazole
inchi=1/c7h6n2/c1-2-4-7-6(3-1)8-5-9-7/h1-5h,(h,8,9
NCGC00091255-01
nsc-759
wln: t56 bm dnj
51-17-2
benzoimidazole
3-azaindole
bzi ,
1h-benzimidazole
benzoglyoxaline
nsc 759
n,n'-methenyl-o-phenylenediamine
azindole
1,3-diazaindene
nsc759
C02009
benziminazole
o-benzimidazole
benzimidazole ,
1,3-benzodiazole
CHEBI:41275 ,
DB02962
benzimidazole, 98%
STK397462
B0054
1h-benzoimidazole
1h-benzo[d]imidazole
CHEMBL306226
AKOS000119163
NCGC00091255-02
NCGC00257173-01
tox21_303321
dtxcid704573
dtxsid8024573 ,
cas-51-17-2
tox21_202107
NCGC00259656-01
HMS2233D03
benzimidazol
e24gx49ld8 ,
5-23-06-00196 (beilstein handbook reference)
unii-e24gx49ld8
FT-0606545
PS-5765
26985-65-9
benzimidazole [hsdb]
benzimidazole [inci]
benzimidazole [mi]
EPITOPE ID:140095
hbzim
hbim
F3366-5347
HMS3370L16
SCHEMBL5197771
AM81999
SCHEMBL6010
SCHEMBL6009
4DSU
bezimidazole
1h-benzimidazol
benz-imidazole
W-105914
CS-W019944
mfcd00005585
SY012765
Q415190
benzimidazole phase betaetha
benzimidazole phase alphalpha
benzimidazole phase gammaamma
D70829
1,3-benzodiazole, bzi
HY-Y1825
1h-1,3-benzimidazole
EN300-33475
chebi:36622

Excerpt	Reference	Relevance
"The benzimidazole is an effective structural unit in which the benzene ring is fused at the 4 and 5 positions of the imidazole ring and wildly used in drug design."	( Recent progress of research on anti-tumor agents using benzimidazole as the structure unit. Cao, X; Chen, M; Li, Y; Peng, J; Peng, X; Peng, Y; Tang, G; Wu, K, 2022)	1.45
"Benzimidazole is a nitrogen-containing fused heterocycle which has been extensively explored in medicinal chemistry. "	( Recent Advancements on Benzimidazole: A Versatile Scaffold in Medicinal Chemistry. Alam, MM; Alzhrani, ZMM; Nazreen, S, 2022)	2.47
"Benzimidazole is an organic compound that is heterocyclic and aromatic in nature."	( Benzimidazole Scaffold as Anticancer Agent: Synthetic Approaches and Structure-Activity Relationship. Ahmed, S; Alam, MJ; Alam, O; Naim, MJ; Nawaz, F; Shrivastava, N, 2017)	2.62
"Benzimidazole is a common kinase inhibitor scaffold and benzimidazole-based compounds interact with enzymes by multiple binding modes. "	( Benzimidazole derivatives as kinase inhibitors. Bottegoni, G; Garuti, L; Roberti, M, 2014)	3.29
"The benzimidazole core is a common moiety in a large number of natural products and pharmacologically active small molecules. "	( An efficient one-pot two catalyst system in the construction of 2-substituted benzimidazoles: synthesis of benzimidazo[1,2-c]quinazolines. Cimarelli, C; Di Nicola, M; Diomedi, S; Giovannini, R; Hamprecht, D; Marcantoni, E; Properzi, R; Sorana, F, 2015)	1.2

Excerpt	Reference	Relevance
"Benzimidazoles (BZ) have been the anthelmintic of choice for controlling Nematodirus battus infections since their release in the 1950s. "	( Large scale screening for benzimidazole resistance mutations in Nematodirus battus, using both pyrosequence genotyping and deep amplicon sequencing, indicates the early emergence of resistance on UK sheep farms. Aitken, C; Avramenko, R; Bartley, DJ; Gilleard, JS; Innocent, G; Melville, LA; Mitchell, S; Morrison, AA; Rebecca Chen, PC; Redman, E; Sargison, F; Van Dijk, J, 2020)	2.3
"Benzimidazoles have been intensively (for over 40 years) used in the livestock sector, particularly in small ruminants. "	( Emergence and the spread of the F200Y benzimidazole resistance mutation in Haemonchus contortus and Haemonchus placei from buffalo and cattle. Ali, Q; Ashraf, K; Chaudhry, U; Rashid, I; Sargison, ND; Shabbir, MZ; Shahzad, K, 2019)	2.23
"Benzimidazole resistance has evolved in a variety of organisms and typically results from mutations in the beta-tubulin locus at specific amino acid sites. "	( Sequence variation in the Trichuris trichiura beta-tubulin locus: implications for the development of benzimidazole resistance. Anderson, TJ; Barker, GC; Bennett, AB; Bundy, DA; Michael, E, 2002)	1.97
"The benzimidazoles (BZ), which have been used for more than 40 years, were chosen as an example."	( Benzimidazole-resistant beta-tubulin alleles in a population of parasitic nematodes (Cooperia oncophora) of cattle. Geary, TG; Johnson, SS; Pomroy, WE; Sangster, NC; Winterrowd, CA, 2003)	2.24

Excerpt	Reference	Relevance
"Benzimidazole plays an important role in the medicinal chemistry and drug discovery with many pharmacological activities which have made an indispensable anchor for discovery of novel therapeutic agents. "	( Novel research strategies of benzimidazole derivatives: a review. Barot, KP; Ghate, MD; Ivanov, I; Nikolova, S, 2013)	2.12

Excerpt	Reference	Relevance
"Benzimidazole (BZM) treatment is given in inoperable cases but these compounds are only parasitostatic, and lifelong therapy is required."	( Indications and results of liver transplantation for Echinococcus alveolar infection: an overview. Bresson-Hadni, S; Gillet, M; Heyd, B; Koch, S; Mantion, GA; Miguet, JP; Vuitton, DA, 2003)	1.04

Excerpt	Reference	Relevance
" In contrast, 2-aromatic ring substituted (benzimidazole-4,7-diones) analogues, benzimidazolequinone with a pyridine ring and mitomycin C were more toxic than the highly conjugated naphthyl fused benzimidazolequinone towards the normal cell line."	( Synthesis and toxicity towards normal and cancer cell lines of benzimidazolequinones containing fused aromatic rings and 2-aromatic ring substituents. Aldabbagh, F; Bonham, S; Carr, M; Carty, MP; Moriarty, E, 2010)	0.86

Excerpt	Reference	Relevance
" Pharmacokinetic descriptors of the compounds investigated were calculated in silico with the use of the established drug design software."	( RP TLC data in correlation studies with in silico pharmacokinetic properties of benzimidazole and benztriazole derivatives. Dimova, VB; Milošević, NP; Perišić-Janjić, NU, 2013)	0.62
"This review provides an update on the following points: pharmacokinetic profile and metabolism of ilaprazole in relation to its pharmacodynamic properties; comparative data on the pharmacokinetics and pharmacodynamics of ilaprazole with currently available PPIs; and implications for studies on the therapeutic efficacy of ilaprazole in GERD."	( The pharmacokinetics of ilaprazole for gastro-esophageal reflux treatment. Blandizzi, C; de Bortoli, N; Giacchino, M; Marchi, S; Martinucci, I; Savarino, E; Savarino, V, 2013)	0.39
"Different studies show that ilaprazole, a benzimidazole derivative, has an extended plasma half-life in comparison with all other approved PPIs."	( The pharmacokinetics of ilaprazole for gastro-esophageal reflux treatment. Blandizzi, C; de Bortoli, N; Giacchino, M; Marchi, S; Martinucci, I; Savarino, E; Savarino, V, 2013)	0.65

Excerpt	Reference	Relevance
" In our continuing efforts to identify small molecule alpha(V)beta(3) and alpha(V)beta(5) dual antagonists, we recently reported indoles 2-4 as potent and selective alpha(V)beta(3)/alpha(V)beta(5) antagonists with good oral bioavailability profile."	( Novel potent and selective alphavbeta3/alphavbeta5 integrin dual antagonists with reduced binding affinity for human serum albumin. Chaikin, M; Crysler, C; Lattanze, J; Leonard, K; Manthey, CL; Marugán, JJ; Pan, W; Raboisson, P; Tomczuk, BE, 2006)	0.33
" Compound 18c demonstrates in vivo CB1 antagonist efficacy (CB1 agonist induced hypothermia model) and is orally bioavailable in rat."	( Identification and hit-to-lead optimization of a novel class of CB1 antagonists. Baker, J; Cowley, P; Edwards, D; Ho, KK; Jokiel, P; Letourneau, JJ; McAleer, L; Ohlmeyer, MH; Olson, J; Riviello, CM; Swanson, RN; Ward, N; Webb, ML; Yang, J, 2010)	0.36

Excerpt	Relevance	Reference
" Lambs from ewes dosed with a benzimidazole (mebendazole) before turn out, developed clinical signs of haemonchosis later in the season."	( Effectiveness of clean grazing strategies in controlling Haemonchus contortus infections in sheep in the United Kingdom. Hunt, KR; Taylor, MA; Wilson, CA, 1991)	0.57
" During 12 weeks of twice-weekly dosing with 3000 parasite larvae (L3), eggs were observed in faeces from CRC-treated and untreated lambs given RES L3, but not CRC-treated lambs given SUS L3."	( The effect of continuous drug exposure on the immune response to Trichostrongylus colubriformis in sheep. Brown, AE; Green, R; Leathwick, DM; Miller, CM; Sutherland, IA, 1999)	0.3
" Over the five generations, LD(50) values on dose-response were increased and worm survival occurred at higher dose rates of TBZ irrespective of the parasite stage exposed to treatment."	( The effects of stage-specific selection on the development of benzimidazole resistance in Haemonchus contortus in sheep. Goodyear, KL; Hunt, KR; Taylor, MA, 2002)	0.56
" Ewes were dosed after lambing with the aim of controlling their periparturient rise in faecal egg output and lambs were dosed at six-week intervals throughout the summer."	( Failure of moxidectin to control benzimidazole-, levamisole- and ivermectin-resistant Teladorsagia circumcinda in a sheep flock. Bartley, DJ; Jackson, F; Moir, AC; Sargison, ND, 2005)	0.61
" The most active compounds 5b and e gave 3/4 cures on an IP dosage of 20 mg/kg."	( Dicationic near-linear biphenyl benzimidazole derivatives as DNA-targeted antiprotozoal agents. Batista-Parra, A; Boykin, DW; Brun, R; Ismail, MA; Miao, Y; Wenzler, T; Wilson, WD, 2005)	0.61
" Two of the compounds showed good activity in vivo in the STIB900 model for acute African trypanosomiasis; one gave 3/4 cures and the other gave 4/4 cures on ip dosage of 20 mg/kg for 4 days."	( Dicationic DNA-targeted antiprotozoal agents: naphthalene replacement of benzimidazole. Boykin, DW; Brun, R; Chackal-Catoen, S; Miao, Y; Wenzler, T; Wilson, WD, 2006)	0.57
" In an ex vivo occupancy assay, Compound A dosed orally to rats caused a concentration dependent inhibition of the specific binding of [(125)I]-S36057 to rat caudate putamen."	( Localisation of melanin-concentrating hormone receptor 1 in rat brain and evidence that sleep parameters are not altered despite high central receptor occupancy. Able, SL; Clarke, TL; Duckworth, JM; Fish, RL; Ivarsson, M; Katugampola, SD; McCourt, C; Napier, C, 2009)	0.35
" The most active compound, 2-[2-(5-nitro-1H-benzimidazol-1-yl)ethyl]-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one 22 revealed 95% activity at a dosage of 5 mg/kg mw after 24 h, while compounds 8 and 10 applied at the same dose showed efficacy of 90% after 48 h."	( Synthesis, antitrichinnellosis and antiprotozoal activity of some novel thieno[2,3-d]pyrimidin-4(3H)-ones containing benzimidazole ring. Anichina, K; Mavrova, ATs; Vassilev, N; Vuchev, D, 2010)	0.57
" The combination of 2,4-difluorobenzyl benzimidazole derivative 5m and its hydrochloride 7 respectively with antibacterial Chloromycin, Norfloxacin or antifungal Fluconazole showed better antimicrobial efficiency with less dosage and broader antimicrobial spectrum than the separated use of them alone."	( Design, synthesis and antimicrobial evaluation of novel benzimidazole type of Fluconazole analogues and their synergistic effects with Chloromycin, Norfloxacin and Fluconazole. Cai, GX; Damu, GL; Zhang, HZ; Zhou, CH, 2013)	0.91
" It was found that even a very low dosage of MNBI-stabilized GNPs exhibit appreciable tumor cell mortality against cervical cancer cell lines, demonstrating the role of NO in killing cancer cells."	( Nitric oxide releasing photoresponsive nanohybrids as excellent therapeutic agent for cervical cancer cell lines. Arumugam, P; Berchmans, S; Sudhesh, P; Tamilarasan, K, 2013)	0.39

Class	Description
benzimidazole	A mancude organic heterobicyclic parent that is a heterocyclic organic compound comprising fused benzene and imidazole rings.
polycyclic heteroarene
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathway	Proteins	Compounds
benzimidazolyl adenosylcobamide biosynthesis from adenosylcobinamide-GDP	3	8

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
progesterone receptor	Homo sapiens (human)	Potency	2.4287	0.0004	17.9460	75.1148	AID1346795
retinoic acid nuclear receptor alpha variant 1	Homo sapiens (human)	Potency	65.7208	0.0030	41.6115	22,387.1992	AID1159552; AID1159553
estrogen-related nuclear receptor alpha	Homo sapiens (human)	Potency	68.5896	0.0015	30.6073	15,848.9004	AID1224841
geminin	Homo sapiens (human)	Potency	3.1623	0.0046	11.3741	33.4983	AID624297
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Membrane primary amine oxidase	Rattus norvegicus (Norway rat)	IC50 (µMol)	100.0000	0.0060	0.5030	1.0000	AID753428
Cytochrome P450 2B1	Rattus norvegicus (Norway rat)	IC50 (µMol)	978.6185	7.4000	7.8000	8.2000	AID38392; AID38394
Glutaminyl-peptide cyclotransferase	Homo sapiens (human)	Ki	144.0000	0.2620	2.9358	7.0000	AID1796109; AID765872
Lanosterol 14-alpha demethylase	Homo sapiens (human)	IC50 (µMol)	200.0000	0.0500	1.4390	4.0000	AID322753
Membrane primary amine oxidase	Homo sapiens (human)	IC50 (µMol)	100.0000	0.0200	1.0400	4.1000	AID753430
Glutaminyl-peptide cyclotransferase	Mus musculus (house mouse)	Ki	192.0000	6.4000	6.4000	6.4000	AID1796111
[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)
Chain A, GTPase KRas, isoform 2B	Homo sapiens (human)	Kd	1,500.0000	1,500.0000	1,500.0000	1,500.0000	AID977611
Chain A, GTPase KRas, isoform 2B	Homo sapiens (human)	Kd	1,500.0000	1,500.0000	1,500.0000	1,500.0000	AID977611
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Cytochrome P450 2B1	Rattus norvegicus (Norway rat)	Ks	110.0000	1.1000	1.1000	1.1000	AID184443
Cytochrome P450 1A1	Rattus norvegicus (Norway rat)	Ks	3,200.0000	1.7000	1.7000	1.7000	AID184441
Polyunsaturated fatty acid 5-lipoxygenase	Rattus norvegicus (Norway rat)	Ks	3,200.0000	1.7000	1.7000	1.7000	AID184441
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
MAPK cascade	GTPase KRas	Homo sapiens (human)
positive regulation of protein phosphorylation	GTPase KRas	Homo sapiens (human)
visual learning	GTPase KRas	Homo sapiens (human)
gene expression	GTPase KRas	Homo sapiens (human)
positive regulation of gene expression	GTPase KRas	Homo sapiens (human)
glial cell proliferation	GTPase KRas	Homo sapiens (human)
Rac protein signal transduction	GTPase KRas	Homo sapiens (human)
forebrain astrocyte development	GTPase KRas	Homo sapiens (human)
actin cytoskeleton organization	GTPase KRas	Homo sapiens (human)
negative regulation of epithelial cell differentiation	GTPase KRas	Homo sapiens (human)
regulation of synaptic transmission, GABAergic	GTPase KRas	Homo sapiens (human)
positive regulation of Rac protein signal transduction	GTPase KRas	Homo sapiens (human)
skeletal muscle cell differentiation	GTPase KRas	Homo sapiens (human)
negative regulation of neuron apoptotic process	GTPase KRas	Homo sapiens (human)
regulation of long-term neuronal synaptic plasticity	GTPase KRas	Homo sapiens (human)
homeostasis of number of cells within a tissue	GTPase KRas	Homo sapiens (human)
striated muscle cell differentiation	GTPase KRas	Homo sapiens (human)
neuron apoptotic process	GTPase KRas	Homo sapiens (human)
positive regulation of glial cell proliferation	GTPase KRas	Homo sapiens (human)
epithelial tube branching involved in lung morphogenesis	GTPase KRas	Homo sapiens (human)
type I pneumocyte differentiation	GTPase KRas	Homo sapiens (human)
Ras protein signal transduction	GTPase KRas	Homo sapiens (human)
peptidyl-pyroglutamic acid biosynthetic process, using glutaminyl-peptide cyclotransferase	Glutaminyl-peptide cyclotransferase	Homo sapiens (human)
protein modification process	Glutaminyl-peptide cyclotransferase	Homo sapiens (human)
steroid biosynthetic process	Lanosterol 14-alpha demethylase	Homo sapiens (human)
cholesterol biosynthetic process	Lanosterol 14-alpha demethylase	Homo sapiens (human)
sterol metabolic process	Lanosterol 14-alpha demethylase	Homo sapiens (human)
negative regulation of protein catabolic process	Lanosterol 14-alpha demethylase	Homo sapiens (human)
negative regulation of protein secretion	Lanosterol 14-alpha demethylase	Homo sapiens (human)
negative regulation of amyloid-beta clearance	Lanosterol 14-alpha demethylase	Homo sapiens (human)
inflammatory response	Membrane primary amine oxidase	Homo sapiens (human)
cell adhesion	Membrane primary amine oxidase	Homo sapiens (human)
amine metabolic process	Membrane primary amine oxidase	Homo sapiens (human)
response to antibiotic	Membrane primary amine oxidase	Homo sapiens (human)
negative regulation of primary amine oxidase activity	Membrane primary amine oxidase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
GTPase activity	GTPase KRas	Homo sapiens (human)
G protein activity	GTPase KRas	Homo sapiens (human)
protein binding	GTPase KRas	Homo sapiens (human)
protein-membrane adaptor activity	GTPase KRas	Homo sapiens (human)
protein-containing complex binding	GTPase KRas	Homo sapiens (human)
GDP binding	GTPase KRas	Homo sapiens (human)
GTP binding	GTPase KRas	Homo sapiens (human)
protein binding	Glutaminyl-peptide cyclotransferase	Homo sapiens (human)
zinc ion binding	Glutaminyl-peptide cyclotransferase	Homo sapiens (human)
glutaminyl-peptide cyclotransferase activity	Glutaminyl-peptide cyclotransferase	Homo sapiens (human)
iron ion binding	Lanosterol 14-alpha demethylase	Homo sapiens (human)
sterol 14-demethylase activity	Lanosterol 14-alpha demethylase	Homo sapiens (human)
heme binding	Lanosterol 14-alpha demethylase	Homo sapiens (human)
oxidoreductase activity	Lanosterol 14-alpha demethylase	Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen	Lanosterol 14-alpha demethylase	Homo sapiens (human)
copper ion binding	Membrane primary amine oxidase	Homo sapiens (human)
calcium ion binding	Membrane primary amine oxidase	Homo sapiens (human)
protein binding	Membrane primary amine oxidase	Homo sapiens (human)
primary amine oxidase activity	Membrane primary amine oxidase	Homo sapiens (human)
identical protein binding	Membrane primary amine oxidase	Homo sapiens (human)
protein heterodimerization activity	Membrane primary amine oxidase	Homo sapiens (human)
quinone binding	Membrane primary amine oxidase	Homo sapiens (human)
aliphatic amine oxidase activity	Membrane primary amine oxidase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
Golgi membrane	GTPase KRas	Homo sapiens (human)
cytoplasm	GTPase KRas	Homo sapiens (human)
mitochondrial outer membrane	GTPase KRas	Homo sapiens (human)
endoplasmic reticulum membrane	GTPase KRas	Homo sapiens (human)
cytosol	GTPase KRas	Homo sapiens (human)
plasma membrane	GTPase KRas	Homo sapiens (human)
focal adhesion	GTPase KRas	Homo sapiens (human)
cytoplasmic side of plasma membrane	GTPase KRas	Homo sapiens (human)
membrane	GTPase KRas	Homo sapiens (human)
plasma membrane	GTPase KRas	Homo sapiens (human)
extracellular region	Glutaminyl-peptide cyclotransferase	Homo sapiens (human)
specific granule lumen	Glutaminyl-peptide cyclotransferase	Homo sapiens (human)
extracellular exosome	Glutaminyl-peptide cyclotransferase	Homo sapiens (human)
tertiary granule lumen	Glutaminyl-peptide cyclotransferase	Homo sapiens (human)
ficolin-1-rich granule lumen	Glutaminyl-peptide cyclotransferase	Homo sapiens (human)
endoplasmic reticulum membrane	Lanosterol 14-alpha demethylase	Homo sapiens (human)
membrane	Lanosterol 14-alpha demethylase	Homo sapiens (human)
cytoplasm	Membrane primary amine oxidase	Homo sapiens (human)
plasma membrane	Membrane primary amine oxidase	Homo sapiens (human)
microvillus	Membrane primary amine oxidase	Homo sapiens (human)
cell surface	Membrane primary amine oxidase	Homo sapiens (human)
membrane	Membrane primary amine oxidase	Homo sapiens (human)
early endosome	Membrane primary amine oxidase	Homo sapiens (human)
endoplasmic reticulum	Membrane primary amine oxidase	Homo sapiens (human)
Golgi apparatus	Membrane primary amine oxidase	Homo sapiens (human)
early endosome	Membrane primary amine oxidase	Homo sapiens (human)
plasma membrane	Membrane primary amine oxidase	Homo sapiens (human)
endoplasmic reticulum	Membrane primary amine oxidase	Homo sapiens (human)
Golgi apparatus	Membrane primary amine oxidase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (96)

Assay ID	Title	Year	Journal	Article
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
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.
AID1745845	Primary qHTS for Inhibitors of ATXN expression
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1543821	Antiproliferative activity against human A549 cells assessed as reduction in cell viability incubated for 48 hrs by MTS assay	2019	European journal of medicinal chemistry, Apr-15, Volume: 168	Synthesis and antitumor activity of novel steroidal imidazolium salt derivatives.
AID1519676	Retention time of compound at pH 7.4 by LC-UV analysis	2020	European journal of medicinal chemistry, Jan-01, Volume: 185	Design of novel monoamine oxidase-B inhibitors based on piperine scaffold: Structure-activity-toxicity, drug-likeness and efflux transport studies.
AID374579	Apparent permeability across bovine cornea assessed as lag time of permeation by UV-visible spectrophotometer	2009	European journal of medicinal chemistry, May, Volume: 44, Issue:5	Synthesis, pharmacological screening, quantum chemical and in vitro permeability studies of N-Mannich bases of benzimidazoles through bovine cornea.
AID658935	Aqueous solubility of the compound	2012	European journal of medicinal chemistry, Jun, Volume: 52	Exploring the interplay of physicochemical properties, membrane permeability and giardicidal activity of some benzimidazole derivatives.
AID1543822	Antiproliferative activity against human SW480 cells assessed as reduction in cell viability incubated for 48 hrs by MTS assay	2019	European journal of medicinal chemistry, Apr-15, Volume: 168	Synthesis and antitumor activity of novel steroidal imidazolium salt derivatives.
AID698041	Antimicrobial activity against metronidazole and clarithromycin-resistant Helicobacter pylori v1254 at pH 8 by microdilution method	2012	European journal of medicinal chemistry, Feb, Volume: 48	Synthesis and bioevaluation of novel 3,4,5-trimethoxybenzylbenzimidazole derivatives that inhibit Helicobacter pylori-induced pathogenesis in human gastric epithelial cells.
AID184441	Interaction with cytochrome P450 in 3-methylcholanthrene-induced rat hepatic microsomes	1982	Journal of medicinal chemistry, Jun, Volume: 25, Issue:6	Inhibitors of hepatic mixed-function oxidases. 4. Effects of benzimidazole and related compounds on aryl hydrocarbon hydroxylase activity from phenobarbitone and 3-methylcholanthrene induced rats.
AID697914	Antimicrobial activity against Helicobacter pylori 26695 ATCC 700392 at 100 ug/ml by disk agar diffusion method	2012	European journal of medicinal chemistry, Feb, Volume: 48	Synthesis and bioevaluation of novel 3,4,5-trimethoxybenzylbenzimidazole derivatives that inhibit Helicobacter pylori-induced pathogenesis in human gastric epithelial cells.
AID765859	Selectivity ratio of Ki for human glutaminyl cyclase H206A mutant to Ki for wild type human glutaminyl cyclase	2013	Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17	Structure-activity relationships of benzimidazole-based glutaminyl cyclase inhibitors featuring a heteroaryl scaffold.
AID698044	Inhibition of Helicobacter pylori 26695 ATCC 700392 cytotoxin A-induced vacuolation in human AGS cells after 24 hrs by neutral red uptake assay	2012	European journal of medicinal chemistry, Feb, Volume: 48	Synthesis and bioevaluation of novel 3,4,5-trimethoxybenzylbenzimidazole derivatives that inhibit Helicobacter pylori-induced pathogenesis in human gastric epithelial cells.
AID1893869	Binding affinity to KRAS (unknown origin) assessed as dissociation constant	2021	European journal of medicinal chemistry, Feb-05, Volume: 211	Targeting KRAS mutant cancers by preventing signaling transduction in the MAPK pathway.
AID753430	Inhibition of human VAP-1 expressed in CHO cells using [14C]-benzylamine as substrate preincubated for 30 mins prior to substrate addition measured after 1 hr by scintillation spectrometric analysis	2013	Bioorganic & medicinal chemistry, Jul-01, Volume: 21, Issue:13	Novel 1H-imidazol-2-amine derivatives as potent and orally active vascular adhesion protein-1 (VAP-1) inhibitors for diabetic macular edema treatment.
AID1231615	Cytotoxicity against human A549 cells assessed as inhibition of cell proliferation rate after 72 hrs by MTT assay	2015	Bioorganic & medicinal chemistry, Jul-01, Volume: 23, Issue:13	Synthesis and biological evaluation of thiabendazole derivatives as anti-angiogenesis and vascular disrupting agents.
AID236904	Partition coefficient (logP)	2005	Bioorganic & medicinal chemistry letters, Jul-01, Volume: 15, Issue:13	Synthesis of selective SRPK-1 inhibitors: novel tricyclic quinoxaline derivatives.
AID1082988	Antifungal activity against Leptosphaeria maculans isolate BJ-125/UAMH-9410 assessed as mycelial growth inhibition at 0.1 mM incubated under constant light for 5 days by mycelial radial growth bioassay	2012	Journal of agricultural and food chemistry, Aug-15, Volume: 60, Issue:32	Metabolism and metabolites of dithiocarbamates in the plant pathogenic fungus Leptosphaeria maculans.
AID1231612	Cytotoxicity against HUVEC assessed as inhibition of cell proliferation rate after 72 hrs by MTT assay	2015	Bioorganic & medicinal chemistry, Jul-01, Volume: 23, Issue:13	Synthesis and biological evaluation of thiabendazole derivatives as anti-angiogenesis and vascular disrupting agents.
AID765869	Selectivity ratio of Ki for human glutaminyl cyclase I303N mutant to Ki for wild type human glutaminyl cyclase	2013	Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17	Structure-activity relationships of benzimidazole-based glutaminyl cyclase inhibitors featuring a heteroaryl scaffold.
AID698052	Antimicrobial activity against metronidazole and clarithromycin-resistant Helicobacter pylori v633 at pH 7 by microdilution method	2012	European journal of medicinal chemistry, Feb, Volume: 48	Synthesis and bioevaluation of novel 3,4,5-trimethoxybenzylbenzimidazole derivatives that inhibit Helicobacter pylori-induced pathogenesis in human gastric epithelial cells.
AID1422527	Antiplasmodial activity against asexual erythrocyte stage of chloroquine-sensitive Plasmodium falciparum NF54 infected in human red blood cells after 48 hrs by lactate dehydrogenase assay	2018	European journal of medicinal chemistry, Nov-05, Volume: 159	Hemozoin inhibiting 2-phenylbenzimidazoles active against malaria parasites.
AID1231626	Induction of vascular disruption in HUVEC after 16 hrs by inverted microscopic analysis	2015	Bioorganic & medicinal chemistry, Jul-01, Volume: 23, Issue:13	Synthesis and biological evaluation of thiabendazole derivatives as anti-angiogenesis and vascular disrupting agents.
AID1231611	Cytotoxicity against HUVEC assessed as inhibition of cell proliferation rate at 100 uM after 72 hrs by MTT assay relative to control	2015	Bioorganic & medicinal chemistry, Jul-01, Volume: 23, Issue:13	Synthesis and biological evaluation of thiabendazole derivatives as anti-angiogenesis and vascular disrupting agents.
AID765864	Selectivity ratio of Ki for human glutaminyl cyclase W329Y mutant to Ki for wild type human glutaminyl cyclase	2013	Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17	Structure-activity relationships of benzimidazole-based glutaminyl cyclase inhibitors featuring a heteroaryl scaffold.
AID765866	Selectivity ratio of Ki for human glutaminyl cyclase F325N mutant to Ki for wild type human glutaminyl cyclase	2013	Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17	Structure-activity relationships of benzimidazole-based glutaminyl cyclase inhibitors featuring a heteroaryl scaffold.
AID765862	Selectivity ratio of Ki for human glutaminyl cyclase W207F mutant to Ki for wild type human glutaminyl cyclase	2013	Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17	Structure-activity relationships of benzimidazole-based glutaminyl cyclase inhibitors featuring a heteroaryl scaffold.
AID1148422	Octanol-water partition coefficient, log P of the compound	1978	Journal of medicinal chemistry, Jan, Volume: 21, Issue:1	Synthesis and adrenergic activity of benzimidazole bioisosteres of norepinephrine and isoproterenol.
AID25099	Acid dissociation constant was determined	1984	Journal of medicinal chemistry, Mar, Volume: 27, Issue:3	Synthesis of a novel class of heteroaromatic amino acids and their use in the preparation of analogues of luteinizing hormone-releasing hormone.
AID765857	Selectivity ratio of Ki for human glutaminyl cyclase K144A mutant to Ki for wild type human glutaminyl cyclase	2013	Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17	Structure-activity relationships of benzimidazole-based glutaminyl cyclase inhibitors featuring a heteroaryl scaffold.
AID765855	Selectivity ratio of Ki for human glutaminyl cyclase K144R mutant to Ki for wild type human glutaminyl cyclase	2013	Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17	Structure-activity relationships of benzimidazole-based glutaminyl cyclase inhibitors featuring a heteroaryl scaffold.
AID39088	Inhibition of Aryl hydrocarbon hydroxylase in phenobarbitone-treated rats	1982	Journal of medicinal chemistry, Jun, Volume: 25, Issue:6	Inhibitors of hepatic mixed-function oxidases. 4. Effects of benzimidazole and related compounds on aryl hydrocarbon hydroxylase activity from phenobarbitone and 3-methylcholanthrene induced rats.
AID38394	Inhibitory potency to aminopyrine N-demethylase activity (P450) in hepatic microsomes from phenobarbitone-induced rats.	1982	Journal of medicinal chemistry, Aug, Volume: 25, Issue:8	Inhibition of rat hepatic microsomal aminopyrine N-demethylase activity by benzimidazole derivatives. Quantitative structure-activity relationships.
AID213502	Anti parasitic activity against Trypanosoma cruzi	2001	Bioorganic & medicinal chemistry letters, Oct-08, Volume: 11, Issue:19	Antiprotozoal and cytotoxicity evaluation of sulfonamide and urea analogues of quinacrine.
AID551809	Displacement of Y-27632 from ROCK-1 assessed as drop in intensity of binding signals by NMR competition experiment	2011	Bioorganic & medicinal chemistry letters, Jan-01, Volume: 21, Issue:1	Fragment-based discovery of 6-substituted isoquinolin-1-amine based ROCK-I inhibitors.
AID765870	Selectivity ratio of Ki for human glutaminyl cyclase I303F mutant to Ki for wild type human glutaminyl cyclase	2013	Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17	Structure-activity relationships of benzimidazole-based glutaminyl cyclase inhibitors featuring a heteroaryl scaffold.
AID698045	Antimicrobial activity against metronidazole and clarithromycin-resistant Helicobacter pylori v1254 at pH 5 by microdilution method	2012	European journal of medicinal chemistry, Feb, Volume: 48	Synthesis and bioevaluation of novel 3,4,5-trimethoxybenzylbenzimidazole derivatives that inhibit Helicobacter pylori-induced pathogenesis in human gastric epithelial cells.
AID765872	Inhibition of human glutaminyl cyclase expressed in Escherichia coli DH5alpha using H-Gln-AMC as substrate by fluorometric analysis in presence of pyroglutamyl aminopeptidase	2013	Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17	Structure-activity relationships of benzimidazole-based glutaminyl cyclase inhibitors featuring a heteroaryl scaffold.
AID698047	Antimicrobial activity against metronidazole and clarithromycin-resistant Helicobacter pylori v633 at pH 8 by microdilution method	2012	European journal of medicinal chemistry, Feb, Volume: 48	Synthesis and bioevaluation of novel 3,4,5-trimethoxybenzylbenzimidazole derivatives that inhibit Helicobacter pylori-induced pathogenesis in human gastric epithelial cells.
AID658931	Antiparasitic activity against Giardia duodenalis IMSS:0989 after 48 hrs	2012	European journal of medicinal chemistry, Jun, Volume: 52	Exploring the interplay of physicochemical properties, membrane permeability and giardicidal activity of some benzimidazole derivatives.
AID1231613	Cytotoxicity against human HCT116 cells assessed as inhibition of cell proliferation rate after 72 hrs by MTT assay	2015	Bioorganic & medicinal chemistry, Jul-01, Volume: 23, Issue:13	Synthesis and biological evaluation of thiabendazole derivatives as anti-angiogenesis and vascular disrupting agents.
AID658934	Lipophilicity, logkw of the compound by RP-HPLC analysis	2012	European journal of medicinal chemistry, Jun, Volume: 52	Exploring the interplay of physicochemical properties, membrane permeability and giardicidal activity of some benzimidazole derivatives.
AID698051	Antimicrobial activity against metronidazole and clarithromycin-resistant Helicobacter pylori v633 at pH 5 by microdilution method	2012	European journal of medicinal chemistry, Feb, Volume: 48	Synthesis and bioevaluation of novel 3,4,5-trimethoxybenzylbenzimidazole derivatives that inhibit Helicobacter pylori-induced pathogenesis in human gastric epithelial cells.
AID753428	Inhibition of rat VAP-1 expressed in CHO cells using [14C]-benzylamine as substrate preincubated for 30 mins prior to substrate addition measured after 1 hr by scintillation spectrometric analysis	2013	Bioorganic & medicinal chemistry, Jul-01, Volume: 21, Issue:13	Novel 1H-imidazol-2-amine derivatives as potent and orally active vascular adhesion protein-1 (VAP-1) inhibitors for diabetic macular edema treatment.
AID23454	Partition coefficient (logP)	1990	Journal of medicinal chemistry, Sep, Volume: 33, Issue:9	Synthesis and in vitro LTD4 antagonist activity of bicyclic and monocyclic cyclopentylurethane and cyclopentylacetamide N-arylsulfonyl amides.
AID39078	Effect on Aryl hydrocarbon hydroxylase activity in 3-methylcolanthrene-induced rat liver microsomes at 1.2x10E-3M	1982	Journal of medicinal chemistry, Jun, Volume: 25, Issue:6	Inhibitors of hepatic mixed-function oxidases. 4. Effects of benzimidazole and related compounds on aryl hydrocarbon hydroxylase activity from phenobarbitone and 3-methylcholanthrene induced rats.
AID284279	Antiamnesic activity against Entamoeba histolytica	2007	Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2	Molecular modeling of some 1H-benzimidazole derivatives with biological activity against Entamoeba histolytica: a comparative molecular field analysis study.
AID1231610	Cytotoxicity against HUVEC assessed as inhibition of cell proliferation rate at 10 uM after 72 hrs by MTT assay relative to control	2015	Bioorganic & medicinal chemistry, Jul-01, Volume: 23, Issue:13	Synthesis and biological evaluation of thiabendazole derivatives as anti-angiogenesis and vascular disrupting agents.
AID184443	Interaction with cytochrome P450 in Phenobarbitone-induced rat hepatic microsomes	1982	Journal of medicinal chemistry, Jun, Volume: 25, Issue:6	Inhibitors of hepatic mixed-function oxidases. 4. Effects of benzimidazole and related compounds on aryl hydrocarbon hydroxylase activity from phenobarbitone and 3-methylcholanthrene induced rats.
AID765867	Selectivity ratio of Ki for human glutaminyl cyclase F325A mutant to Ki for wild type human glutaminyl cyclase	2013	Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17	Structure-activity relationships of benzimidazole-based glutaminyl cyclase inhibitors featuring a heteroaryl scaffold.
AID1543818	Antiproliferative activity against human HL60 cells assessed as reduction in cell viability incubated for 48 hrs by MTS assay	2019	European journal of medicinal chemistry, Apr-15, Volume: 168	Synthesis and antitumor activity of novel steroidal imidazolium salt derivatives.
AID765865	Selectivity ratio of Ki for human glutaminyl cyclase F325Y mutant to Ki for wild type human glutaminyl cyclase	2013	Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17	Structure-activity relationships of benzimidazole-based glutaminyl cyclase inhibitors featuring a heteroaryl scaffold.
AID210974	Percentage viability reduction of Trichinella spiralis muscle larvae after 3 days of incubation; No reduction observed	2002	Bioorganic & medicinal chemistry letters, Aug-19, Volume: 12, Issue:16	Synthesis and antiparasitic activity of 1H-benzimidazole derivatives.
AID658936	Distribution coefficient, log D of the compound	2012	European journal of medicinal chemistry, Jun, Volume: 52	Exploring the interplay of physicochemical properties, membrane permeability and giardicidal activity of some benzimidazole derivatives.
AID765858	Selectivity ratio of Ki for human glutaminyl cyclase H206Q mutant to Ki for wild type human glutaminyl cyclase	2013	Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17	Structure-activity relationships of benzimidazole-based glutaminyl cyclase inhibitors featuring a heteroaryl scaffold.
AID1231621	Inhibition of alpha-tubulin formation in human A549 cells at 250 uM after 24 hrs by TRITC/Hoechst 33258 staining-based immunofluorescence microscopic analysis	2015	Bioorganic & medicinal chemistry, Jul-01, Volume: 23, Issue:13	Synthesis and biological evaluation of thiabendazole derivatives as anti-angiogenesis and vascular disrupting agents.
AID1543819	Antiproliferative activity against human SMMC7721 cells assessed as reduction in cell viability incubated for 48 hrs by MTS assay	2019	European journal of medicinal chemistry, Apr-15, Volume: 168	Synthesis and antitumor activity of novel steroidal imidazolium salt derivatives.
AID698053	Antimicrobial activity against Helicobacter pylori 26695 ATCC 700392 at pH 8 by microdilution method	2012	European journal of medicinal chemistry, Feb, Volume: 48	Synthesis and bioevaluation of novel 3,4,5-trimethoxybenzylbenzimidazole derivatives that inhibit Helicobacter pylori-induced pathogenesis in human gastric epithelial cells.
AID322753	Inhibition of human CYP51 expressed in Topp 3 cells by lanosterol demethylase assay	2007	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 35, Issue:3	Three-dimensional quantitative structure-activity relationship analysis of human CYP51 inhibitors.
AID374578	Apparent permeability across bovine cornea by UV-visible spectrophotometer	2009	European journal of medicinal chemistry, May, Volume: 44, Issue:5	Synthesis, pharmacological screening, quantum chemical and in vitro permeability studies of N-Mannich bases of benzimidazoles through bovine cornea.
AID765856	Selectivity ratio of Ki for human glutaminyl cyclase K144M mutant to Ki for wild type human glutaminyl cyclase	2013	Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17	Structure-activity relationships of benzimidazole-based glutaminyl cyclase inhibitors featuring a heteroaryl scaffold.
AID697912	Antimicrobial activity against Helicobacter pylori 26695 ATCC 700392 at pH 7 by microdilution method	2012	European journal of medicinal chemistry, Feb, Volume: 48	Synthesis and bioevaluation of novel 3,4,5-trimethoxybenzylbenzimidazole derivatives that inhibit Helicobacter pylori-induced pathogenesis in human gastric epithelial cells.
AID697913	Antimicrobial activity against Helicobacter pylori 26695 ATCC 700392 at pH 5 by microdilution method	2012	European journal of medicinal chemistry, Feb, Volume: 48	Synthesis and bioevaluation of novel 3,4,5-trimethoxybenzylbenzimidazole derivatives that inhibit Helicobacter pylori-induced pathogenesis in human gastric epithelial cells.
AID26812	Partition coefficient (logP)	1982	Journal of medicinal chemistry, Jun, Volume: 25, Issue:6	Inhibitors of hepatic mixed-function oxidases. 4. Effects of benzimidazole and related compounds on aryl hydrocarbon hydroxylase activity from phenobarbitone and 3-methylcholanthrene induced rats.
AID1231614	Cytotoxicity against human HepG2 cells assessed as inhibition of cell proliferation rate after 72 hrs by MTT assay	2015	Bioorganic & medicinal chemistry, Jul-01, Volume: 23, Issue:13	Synthesis and biological evaluation of thiabendazole derivatives as anti-angiogenesis and vascular disrupting agents.
AID765861	Selectivity ratio of Ki for human glutaminyl cyclase W207L mutant to Ki for wild type human glutaminyl cyclase	2013	Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17	Structure-activity relationships of benzimidazole-based glutaminyl cyclase inhibitors featuring a heteroaryl scaffold.
AID1743052	Antigiardial activity against Giardia lamblia IMSS:0989:1 incubated for 48 hrs followed by compound wash out and measured after 48 hrs	2020	Journal of medicinal chemistry, 11-25, Volume: 63, Issue:22	Anti-
AID667489	Inhibition of recombinant type N-terminal His6-tagged 2 R67 DHFR expressed in Escherichia coli BL21 using DHF as substrate by spectrophotometry	2012	Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7	Fragment-based design of symmetrical bis-benzimidazoles as selective inhibitors of the trimethoprim-resistant, type II R67 dihydrofolate reductase.
AID765868	Selectivity ratio of Ki for human glutaminyl cyclase I303V mutant to Ki for wild type human glutaminyl cyclase	2013	Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17	Structure-activity relationships of benzimidazole-based glutaminyl cyclase inhibitors featuring a heteroaryl scaffold.
AID698036	Inhibition of NFkappaB activation expressed in human AGS cells infected with Helicobacter pylori at 20 ug/ml relative to control	2012	European journal of medicinal chemistry, Feb, Volume: 48	Synthesis and bioevaluation of novel 3,4,5-trimethoxybenzylbenzimidazole derivatives that inhibit Helicobacter pylori-induced pathogenesis in human gastric epithelial cells.
AID1082989	Antifungal activity against Leptosphaeria maculans isolate BJ-125/UAMH-9410 assessed as mycelial growth inhibition at 0.2 mM incubated under constant light for 5 days by mycelial radial growth bioassay	2012	Journal of agricultural and food chemistry, Aug-15, Volume: 60, Issue:32	Metabolism and metabolites of dithiocarbamates in the plant pathogenic fungus Leptosphaeria maculans.
AID67529	The compound was tested in vitro against the protozoa Entamoeba histolytica, for the inhibition of tubulin polymerization in rat brain	2002	Bioorganic & medicinal chemistry letters, Aug-19, Volume: 12, Issue:16	Synthesis and antiparasitic activity of 1H-benzimidazole derivatives.
AID765860	Selectivity ratio of Ki for human glutaminyl cyclase W207Q mutant to Ki for wild type human glutaminyl cyclase	2013	Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17	Structure-activity relationships of benzimidazole-based glutaminyl cyclase inhibitors featuring a heteroaryl scaffold.
AID1543820	Antiproliferative activity against human MCF7 cells assessed as reduction in cell viability incubated for 48 hrs by MTS assay	2019	European journal of medicinal chemistry, Apr-15, Volume: 168	Synthesis and antitumor activity of novel steroidal imidazolium salt derivatives.
AID1519674	Chromatographic hydrophobicity index of compound at 250 uM at pH 7.4 by HPLC analysis	2020	European journal of medicinal chemistry, Jan-01, Volume: 185	Design of novel monoamine oxidase-B inhibitors based on piperine scaffold: Structure-activity-toxicity, drug-likeness and efflux transport studies.
AID75268	The compound was tested in vitro against the protozoa Giardia lamblia, for the inhibition of tubulin polymerization in rat brain	2002	Bioorganic & medicinal chemistry letters, Aug-19, Volume: 12, Issue:16	Synthesis and antiparasitic activity of 1H-benzimidazole derivatives.
AID698042	Antimicrobial activity against metronidazole and clarithromycin-resistant Helicobacter pylori v1254 at pH 7 by microdilution method	2012	European journal of medicinal chemistry, Feb, Volume: 48	Synthesis and bioevaluation of novel 3,4,5-trimethoxybenzylbenzimidazole derivatives that inhibit Helicobacter pylori-induced pathogenesis in human gastric epithelial cells.
AID1422526	Inhibition of beta hematin formation after 5 to 6 hrs by NP40 detergent-based assay	2018	European journal of medicinal chemistry, Nov-05, Volume: 159	Hemozoin inhibiting 2-phenylbenzimidazoles active against malaria parasites.
AID38392	Inhibition of Aminopyrine N-demethylase in Phenobarbitone-treated rats	1982	Journal of medicinal chemistry, Jun, Volume: 25, Issue:6	Inhibitors of hepatic mixed-function oxidases. 4. Effects of benzimidazole and related compounds on aryl hydrocarbon hydroxylase activity from phenobarbitone and 3-methylcholanthrene induced rats.
AID765871	Selectivity ratio of Ki for human glutaminyl cyclase I303A mutant to Ki for wild type human glutaminyl cyclase	2013	Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17	Structure-activity relationships of benzimidazole-based glutaminyl cyclase inhibitors featuring a heteroaryl scaffold.
AID24235	Partition coefficient (logP)	1982	Journal of medicinal chemistry, Aug, Volume: 25, Issue:8	Inhibition of rat hepatic microsomal aminopyrine N-demethylase activity by benzimidazole derivatives. Quantitative structure-activity relationships.
AID39090	Inhibition of Aryl hydrocarbon hydroxylase in phenobarbitone-treated rats	1982	Journal of medicinal chemistry, Jun, Volume: 25, Issue:6	Inhibitors of hepatic mixed-function oxidases. 4. Effects of benzimidazole and related compounds on aryl hydrocarbon hydroxylase activity from phenobarbitone and 3-methylcholanthrene induced rats.
AID1082990	Antifungal activity against Leptosphaeria maculans isolate BJ-125/UAMH-9410 assessed as mycelial growth inhibition at 0.5 mM incubated under constant light for 5 days by mycelial radial growth bioassay	2012	Journal of agricultural and food chemistry, Aug-15, Volume: 60, Issue:32	Metabolism and metabolites of dithiocarbamates in the plant pathogenic fungus Leptosphaeria maculans.
AID765863	Selectivity ratio of Ki for human glutaminyl cyclase W329F mutant to Ki for wild type human glutaminyl cyclase	2013	Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17	Structure-activity relationships of benzimidazole-based glutaminyl cyclase inhibitors featuring a heteroaryl scaffold.
AID1796111	QC Inhibition Testing from Article 10.1021/bi051142e: \\Isolation, catalytic properties, and competitive inhibitors of the zinc-dependent murine glutaminyl cyclase.\\	2005	Biochemistry, Oct-11, Volume: 44, Issue:40	Isolation, catalytic properties, and competitive inhibitors of the zinc-dependent murine glutaminyl cyclase.
AID1796109	QC Inhibition Testing from Article 10.1074/jbc.M309077200: \\Identification of human glutaminyl cyclase as a metalloenzyme. Potent inhibition by imidazole derivatives and heterocyclic chelators.\\	2003	The Journal of biological chemistry, Dec-12, Volume: 278, Issue:50	Identification of human glutaminyl cyclase as a metalloenzyme. Potent inhibition by imidazole derivatives and heterocyclic chelators.
AID1802737	Resonance Raman Assay from Article 10.1021/acs.biochem.7b00041: \\Interaction of Azole-Based Environmental Pollutants with the Coelomic Hemoglobin from Amphitrite ornata: A Molecular Basis for Toxicity.\\	2017	Biochemistry, 05-02, Volume: 56, Issue:17	Interaction of Azole-Based Environmental Pollutants with the Coelomic Hemoglobin from Amphitrite ornata: A Molecular Basis for Toxicity.
AID977611	Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB	2012	Proceedings of the National Academy of Sciences of the United States of America, Apr-03, Volume: 109, Issue:14	Small-molecule ligands bind to a distinct pocket in Ras and inhibit SOS-mediated nucleotide exchange activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	94 (8.08)	18.7374
1990's	49 (4.21)	18.2507
2000's	265 (22.79)	29.6817
2010's	629 (54.08)	24.3611
2020's	126 (10.83)	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	16 (1.35%)	5.53%
Reviews	52 (4.38%)	6.00%
Case Studies	5 (0.42%)	4.05%
Observational	0 (0.00%)	0.25%
Other	1,113 (93.84%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Trial	Phase	Enrollment	Study Type	Start Date	Status
Establishing a Surveillance System to Monitor the Global Patterns of Drug Efficacy and Emergence of Anthelmintic Resistance in Soil-transmitted Helminth Programs [NCT04177654]		9,457 participants (Actual)	Observational	2019-05-15	Completed
Alveolar Echinococcosis: Parasite Viability and Innovative Markers for Follow-up of Patients Treated With Albendazole - EchinoVISTA Prospective Clinical Study [NCT02876146]		50 participants (Actual)	Interventional	2012-06-30	Completed
A Phase 3, Randomized, Double-blind, Active Controlled Study to Compare the Efficacy and Safety of Ridinilazole (200 mg, Bid) for 10 Days With Vancomycin (125 mg, Qid) for 10 Days in the Treatment of Clostridium Difficile Infection (CDI) [NCT03595553]	Phase 3	759 participants (Actual)	Interventional	2019-01-28	Completed
Phase 1 Study to Evaluate the Effect of CYP Polymorphism and Gender on the Pharmacokinetics and Pharmacodynamics of Ilaprazole After Multiple Dosing [NCT01688544]	Phase 1	27 participants (Actual)	Interventional	2009-01-31	Completed
Human Soil Transmitted Helminths (STH) Resistance to Benzimidazole in School Aged Children Living in Gabon [NCT04326868]	Phase 4	255 participants (Actual)	Interventional	2019-11-11	Completed
A Phase I Study to Investigate the Safety, Pharmacokinetic Profile and the Efficacy of EDO-S101, a First-in-Class Alkylating HDACi Fusion Molecule in Patients With Newly Di-Agnosed MGMT-Promoter Unmethylated Glioblastoma [NCT03452930]	Phase 1	92 participants (Anticipated)	Interventional	2018-08-13	Active, not recruiting
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Trial	Outcome
NCT03595553 (8) [back to overview]	Measure of β-diversity of the Gut Microbiota Between Baseline and EOT Stool Samples (Bray-Curtis Index/Dissimilarity).
NCT03595553 (8) [back to overview]	Percentage of Change of α-diversity (Shannon Index) of the Microbiota in Stool Samples From Baseline to EOT.
NCT03595553 (8) [back to overview]	Clinical Cure
NCT03595553 (8) [back to overview]	Clinical Response
NCT03595553 (8) [back to overview]	Number of Participants With Sustained Clinical Response (SCR) Defined as Clinical Response and no Recurrence of CDI Through 30 Days Post End of Treatment (EOT).
NCT03595553 (8) [back to overview]	Relative Abundance of the 3 Main Bile Acid Groups (Conjugated Primary, Primary and Secondary Bile Acids) From Baseline to EOT.
NCT03595553 (8) [back to overview]	Sustained Clinical Response Over 60 Days
NCT03595553 (8) [back to overview]	Sustained Clinical Response Over 90 Days

Intervention	Bray-Curtis Index (Mean)
Ridinilazole	0.7
Vancomycin	0.81

Intervention	percent change in Shannon Index (Mean)
Ridinilazole	37.06
Vancomycin	-7.32

Intervention	Participants (Count of Participants)
	Clinical Cure	Clinical Cure Failure
Ridinilazole	275	95
Vancomycin	292	83

Intervention	Participants (Count of Participants)
	Clinical Response	Clinical Response Failure
Ridinilazole	320	50
Vancomycin	346	29

Intervention	Participants (Count of Participants)
	SCR based on Clinical Cure	SCR based on Clinical Cure Failure
Ridinilazole	238	132
Vancomycin	225	150

Intervention	percentage of abundance (Mean)
	Secondary Bile Acid Group at Baseline	Secondary Bile Acid Group at EOT	Primary Bile Acid Group at Baseline	Primary Bile Acid Group at EOT	Conjugated Primary Bile Acid Group at Baseline	Conjugated Primary Bile Acid Group at EOT
Ridinilazole	33.34	38.13	55.03	55.99	11.64	5.88
Vancomycin	30.25	7.87	57.44	65.72	12.31	26.42

Intervention	Participants (Count of Participants)
	Sustained Clinical Response 60 Days Post EOT	Sustained Clinical Response 60 Days Post EOT Failure
Ridinilazole	262	108
Vancomycin	258	117

Intervention	Participants (Count of Participants)
	Sustained Clinical Response 90 Days Post EOT	Sustained Clinical Response 90 Days Post EOT Failure
Ridinilazole	259	111
Vancomycin	249	126

Substance	Relationship Strength	Studies	Trials	Classes	Roles
5-hydroxytryptophan 5-Hydroxytryptophan: The immediate precursor in the biosynthesis of SEROTONIN from tryptophan. It is used as an antiepileptic and antidepressant.. 5-hydroxytryptophan : A tryptophan derivative that is tryptophan substituted by a hydroxy group at position 5.	2.01	1	0	hydroxytryptophan	human metabolite; neurotransmitter
ethylene glycol Ethylene Glycol: A colorless, odorless, viscous dihydroxy alcohol. It has a sweet taste, but is poisonous if ingested. Ethylene glycol is the most important glycol commercially available and is manufactured on a large scale in the United States. It is used as an antifreeze and coolant, in hydraulic fluids, and in the manufacture of low-freezing dynamites and resins.. ethanediol : Any diol that is ethane or substituted ethane carrying two hydroxy groups.. ethylene glycol : A 1,2-glycol compound produced via reaction of ethylene oxide with water.	2.08	1	0	ethanediol; glycol	metabolite; mouse metabolite; solvent; toxin
acetic acid Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.	2.48	2	0	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
adenine [no description available]	8.06	5	0	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
quinacrine Quinacrine: An acridine derivative formerly widely used as an antimalarial but superseded by chloroquine in recent years. It has also been used as an anthelmintic and in the treatment of giardiasis and malignant effusions. It is used in cell biological experiments as an inhibitor of phospholipase A2.. quinacrine : A member of the class of acridines that is acridine substituted by a chloro group at position 6, a methoxy group at position 2 and a [5-(diethylamino)pentan-2-yl]nitrilo group at position 9.	3.56	2	0	acridines; aromatic ether; organochlorine compound; tertiary amino compound	antimalarial; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor
beta-alanine [no description available]	2	1	0	amino acid zwitterion; beta-amino acid	agonist; fundamental metabolite; human metabolite; inhibitor; neurotransmitter
benzene [no description available]	8.89	3	0	aromatic annulene; benzenes; volatile organic compound	carcinogenic agent; environmental contaminant; non-polar solvent
1-butanol 1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.	2.5	2	0	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
butyric acid Butyric Acid: A four carbon acid, CH3CH2CH2COOH, with an unpleasant odor that occurs in butter and animal fat as the glycerol ester.. butyrate : A short-chain fatty acid anion that is the conjugate base of butyric acid, obtained by deprotonation of the carboxy group.. butyric acid : A straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group.	6.96	1	0	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
carbamates [no description available]	5.47	14	1	amino-acid anion
carbon monoxide Carbon Monoxide: Carbon monoxide (CO). A poisonous colorless, odorless, tasteless gas. It combines with hemoglobin to form carboxyhemoglobin, which has no oxygen carrying capacity. The resultant oxygen deprivation causes headache, dizziness, decreased pulse and respiratory rates, unconsciousness, and death. (From Merck Index, 11th ed). carbon monoxide : A one-carbon compound in which the carbon is joined only to a single oxygen. It is a colourless, odourless, tasteless, toxic gas.	2.17	1	0	carbon oxide; gas molecular entity; one-carbon compound	biomarker; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; human metabolite; ligand; metabolite; mitochondrial respiratory-chain inhibitor; mouse metabolite; neurotoxin; neurotransmitter; P450 inhibitor; probe; signalling molecule; vasodilator agent
formic acid formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.	2.05	1	0	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
catechol [no description available]	1.95	1	0	catechols	allelochemical; genotoxin; plant metabolite
methane Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).	8.41	7	0	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	2.92	4	0	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
hydrochloric acid Hydrochloric Acid: A strong corrosive acid that is commonly used as a laboratory reagent. It is formed by dissolving hydrogen chloride in water. GASTRIC ACID is the hydrochloric acid component of GASTRIC JUICE.. hydrogen chloride : A mononuclear parent hydride consisting of covalently bonded hydrogen and chlorine atoms.	2.47	2	0	chlorine molecular entity; gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
coumarin 2H-chromen-2-one: coumarin derivative	3.92	3	0	coumarins	fluorescent dye; human metabolite; plant metabolite
2,3-diaminopropionic acid 3-aminoalanine : A diamino acid that is alanine in which one of the hydrogens of the methyl group is replaced by an amino group.	2	1	0	alanine derivative; amino acid zwitterion; beta-amino acid; diamino acid; non-proteinogenic alpha-amino acid	Escherichia coli metabolite
hydrogen sulfide Hydrogen Sulfide: A flammable, poisonous gas with a characteristic odor of rotten eggs. It is used in the manufacture of chemicals, in metallurgy, and as an analytical reagent. (From Merck Index, 11th ed). hydrogen sulfide : A sulfur hydride consisting of a single sulfur atom bonded to two hydrogen atoms. A highly poisonous, flammable gas with a characteristic odour of rotten eggs, it is often produced by bacterial decomposition of organic matter in the absence of oxygen.. thiol : An organosulfur compound in which a thiol group, -SH, is attached to a carbon atom of any aliphatic or aromatic moiety.	7.52	2	0	gas molecular entity; hydracid; mononuclear parent hydride; sulfur hydride	Escherichia coli metabolite; genotoxin; metabolite; signalling molecule; toxin; vasodilator agent
cytosine [no description available]	2.02	1	0	aminopyrimidine; pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	2.07	1	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
5,6-dimethylbenzimidazole 5,6-dimethylbenzimidazole: RN given refers to parent cpd. 5,6-dimethylbenzimidazole : A dimethylbenzimidazole carrying methyl substituents at positions 5 and 6.	3.05	5	0	dimethylbenzimidazole	Escherichia coli metabolite; human 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.	7.85	3	0	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
ethanolamine [no description available]	2.02	1	0	ethanolamines; primary alcohol; primary amine	Escherichia coli metabolite; human metabolite; mouse metabolite
glycine [no description available]	2.02	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
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	1.96	1	0	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
alpha-glycerophosphoric acid [no description available]	2.02	1	0	glycerol monophosphate	algal metabolite; human metabolite
histamine [no description available]	2.38	2	0	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.	7.96	4	0	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
imidazole imidazole: RN given refers to parent cpd. 1H-imidazole : An imidazole tautomer which has the migrating hydrogen at position 1.	6.63	27	0	imidazole
indole [no description available]	3.93	12	0	indole; polycyclic heteroarene	Escherichia coli metabolite
iodine Iodine: A nonmetallic element of the halogen group that is represented by the atomic symbol I, atomic number 53, and atomic weight of 126.90. It is a nutritionally essential element, especially important in thyroid hormone synthesis. In solution, it has anti-infective properties and is used topically.. diiodine : Molecule comprising two covalently bonded iodine atoms with overall zero charge..	7.48	2	0	diatomic iodine	nutrient
malonic acid malonic acid : An alpha,omega-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group.. dicarboxylic acid : Any carboxylic acid containing two carboxy groups.	2.06	1	0	alpha,omega-dicarboxylic acid	human metabolite
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	2.99	4	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
acetanilide acetanilide: a phenylacetamide; use ACETANILIDES for the plural group meaning of the singular term. N-phenylacetamide : A member of the class of acetamides that is acetamide in which one of the hydrogens attached to the nitrogen is substituted by a phenyl group.	2.17	1	0	acetamides; anilide	analgesic
naphthalene [no description available]	7.8	3	0	naphthalenes; ortho-fused bicyclic arene	apoptosis inhibitor; carcinogenic agent; environmental contaminant; mouse metabolite; plant metabolite; volatile oil component
nickel Nickel: A trace element with the atomic symbol Ni, atomic number 28, and atomic weight 58.69. It is a cofactor of the enzyme UREASE.. nickel ion : A nickel atom having a net electric charge.. nickel atom : Chemical element (nickel group element atom) with atomic number 28.	3.47	7	0	metal allergen; nickel group element atom	epitope; micronutrient
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	2.43	2	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
orotic acid Orotic Acid: An intermediate product in PYRIMIDINE synthesis which plays a role in chemical conversions between DIHYDROFOLATE and TETRAHYDROFOLATE.. orotic acid : A pyrimidinemonocarboxylic acid that is uracil bearing a carboxy substituent at position C-6.	1.94	1	0	pyrimidinemonocarboxylic acid	Escherichia coli metabolite; metabolite; mouse metabolite
4-aminobenzoic acid 4-Aminobenzoic Acid: An aminobenzoic acid isomer that combines with pteridine and GLUTAMIC ACID to form FOLIC ACID. The fact that 4-aminobenzoic acid absorbs light throughout the UVB range has also resulted in its use as an ingredient in SUNSCREENS.. 4-ammoniobenzoate : A zwitterion obtained by transfer of a proton from the carboxy to the amino group of 4-aminobenzoic acid.. 4-aminobenzoic acid : An aminobenzoic acid in which the amino group is para to the carboxy group.	2.06	1	0	aminobenzoic acid; aromatic amino-acid zwitterion	allergen; Escherichia coli metabolite; plant metabolite
phenol [no description available]	2.78	3	0	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
phthalic acid phthalic acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7178. phthalic acid : A benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions.	2.04	1	0	benzenedicarboxylic acid	human xenobiotic metabolite
porphobilinogen [no description available]	2.1	1	0	aralkylamino compound; dicarboxylic acid; pyrroles	Escherichia coli metabolite; metabolite; mouse metabolite
propylene glycol Propylene Glycol: A clear, colorless, viscous organic solvent and diluent used in pharmaceutical preparations.. propane-1,2-diol : The simplest member of the class of propane-1,2-diols, consisting of propane in which a hydrogen at position 1 and a hydrogen at position 2 are substituted by hydroxy groups. A colourless, viscous, hygroscopic, low-melting (-59degreeC) and high-boiling (188degreeC) liquid with low toxicity, it is used as a solvent, emulsifying agent, and antifreeze.	1.96	1	0	glycol; propane-1,2-diols	allergen; human xenobiotic metabolite; mouse metabolite; protic solvent
propionic acid propionic acid : A short-chain saturated fatty acid comprising ethane attached to the carbon of a carboxy group.	2	1	0	saturated fatty acid; short-chain fatty acid	antifungal drug
purine 1H-purine : The 1H-tautomer of purine.. 3H-purine : The 3H-tautomer of purine.. 9H-purine : The 9H-tautomer of purine.. 7H-purine : The 7H-tautomer of purine.	2.9	4	0	purine
pyrazole 1H-pyrazole : The 1H-tautomer of pyrazole.	5.93	11	0	pyrazole
pyridine azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.	3.79	10	0	azaarene; mancude organic heteromonocyclic parent; monocyclic heteroarene; pyridines	environmental contaminant; NMR chemical shift reference compound
pyridoxal [no description available]	2.06	1	0	hydroxymethylpyridine; methylpyridines; monohydroxypyridine; pyridinecarbaldehyde; vitamin B6	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
pyruvic acid Pyruvic Acid: An intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed). pyruvic acid : A 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis.	2.44	2	0	2-oxo monocarboxylic acid	cofactor; fundamental metabolite
sulfur dioxide Sulfur Dioxide: A highly toxic, colorless, nonflammable gas. It is used as a pharmaceutical aid and antioxidant. It is also an environmental air pollutant.	2.21	1	0	sulfur oxide	Escherichia coli metabolite; food bleaching agent; refrigerant
taurine [no description available]	2.11	1	0	amino sulfonic acid; zwitterion	antioxidant; Escherichia coli metabolite; glycine receptor agonist; human metabolite; mouse metabolite; nutrient; radical scavenger; Saccharomyces cerevisiae metabolite
thymine [no description available]	2.41	2	0	pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	2	1	0	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
tryptamine [no description available]	2.07	1	0	aminoalkylindole; aralkylamino compound; indole alkaloid; tryptamines	human metabolite; mouse metabolite; plant metabolite
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	1.94	1	0	pyrimidine nucleobase; pyrimidone	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; prodrug; Saccharomyces cerevisiae metabolite
uric acid Uric Acid: An oxidation product, via XANTHINE OXIDASE, of oxypurines such as XANTHINE and HYPOXANTHINE. It is the final oxidation product of purine catabolism in humans and primates, whereas in most other mammals URATE OXIDASE further oxidizes it to ALLANTOIN.. uric acid : An oxopurine that is the final oxidation product of purine metabolism.. 6-hydroxy-1H-purine-2,8(7H,9H)-dione : A tautomer of uric acid having oxo groups at C-2 and C-8 and a hydroxy group at C-6.. 7,9-dihydro-1H-purine-2,6,8(3H)-trione : An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8.	2.25	1	0	uric acid	Escherichia coli metabolite; human metabolite; mouse metabolite
urea pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.	9.74	5	0	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
xanthine 7H-xanthine : An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-7 is protonated.. 9H-xanthine : An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-9 is protonated.	2.07	1	0	xanthine	Saccharomyces cerevisiae metabolite
1,10-phenanthroline 1,10-phenanthroline: RN given refers to parent cpd; inhibits Zn-dependent metalloproteinases	2.01	1	0	phenanthroline	EC 2.7.1.1 (hexokinase) inhibitor; EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor
1-methylimidazole 1-methyl-1H-imidazole : A 1H-imidazole having a methyl substituent at the N-1 position.	2.68	3	0	imidazoles
2,2'-dipyridyl 2,2'-Dipyridyl: A reagent used for the determination of iron.. 2,2'-bipyridine : A bipyridine in which the two pyridine moieties are linked by a bond between positions C-2 and C-2'.	2.11	1	0	bipyridine	chelator; ferroptosis inhibitor
mercaptoethanol Mercaptoethanol: A water-soluble thiol derived from hydrogen sulfide and ethanol. It is used as a reducing agent for disulfide bonds and to protect sulfhydryl groups from oxidation.	2.02	1	0	alkanethiol; primary alcohol	geroprotector
3-methylcholanthrene Methylcholanthrene: A carcinogen that is often used in experimental cancer studies.. 3-methylcholanthrene : A pentacyclic ortho- and peri-fused polycyclic arene consisting of a dihydrocyclopenta[ij]tetraphene ring system with a methyl substituent at the 3-position.	2.39	2	0	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
4,5,6,7-tetrabromo-2-azabenzimidazole 4,5,6,7-tetrabromobenzotriazole: a CK2 kinase inhibitor	2.44	2	0
8-phenyltheophylline 8-phenyltheophylline: purinergic P1 receptor antagonist	2.02	1	0
oxyquinoline Oxyquinoline: An antiseptic with mild fungistatic, bacteriostatic, anthelmintic, and amebicidal action. It is also used as a reagent and metal chelator, as a carrier for radio-indium for diagnostic purposes, and its halogenated derivatives are used in addition as topical anti-infective agents and oral antiamebics.. quinolin-8-ol : A monohydroxyquinoline that is quinoline substituted by a hydroxy group at position 8. Its fungicidal properties are used for the control of grey mould on vines and tomatoes.	2.31	1	0	monohydroxyquinoline	antibacterial agent; antifungal agrochemical; antiseptic drug; iron chelator
acetaminophen Acetaminophen: Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage.. paracetamol : A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.	2.51	2	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
albendazole [no description available]	10.52	34	5	aryl sulfide; benzimidazoles; benzimidazolylcarbamate fungicide; carbamate ester	anthelminthic drug; microtubule-destabilising agent; tubulin modulator
theophylline [no description available]	2.48	2	0	dimethylxanthine	adenosine receptor antagonist; anti-asthmatic drug; anti-inflammatory agent; bronchodilator agent; drug metabolite; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; fungal metabolite; human blood serum metabolite; immunomodulator; muscle relaxant; vasodilator agent
amodiaquine Amodiaquine: A 4-aminoquinoline compound with anti-inflammatory properties.. amodiaquine : A quinoline having a chloro group at the 7-position and an aryl amino group at the 4-position.	2.07	1	0	aminoquinoline; organochlorine compound; phenols; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; drug allergen; EC 2.1.1.8 (histamine N-methyltransferase) inhibitor; non-steroidal anti-inflammatory drug; prodrug
aspirin Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.	1.97	1	0	benzoic acids; phenyl acetates; salicylates	anticoagulant; antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; EC 1.1.1.188 (prostaglandin-F synthase) inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; plant activator; platelet aggregation inhibitor; prostaglandin antagonist; teratogenic agent
astemizole Astemizole: Antihistamine drug now withdrawn from the market in many countries because of rare but potentially fatal side effects.. astemizole : A piperidine compound having a 2-(4-methoxyphenyl)ethyl group at the 1-position and an N-[(4-fluorobenzyl)benzimidazol-2-yl]amino group at the 4-position.	7.08	1	0	benzimidazoles; piperidines	anti-allergic agent; anticoronaviral agent; H1-receptor antagonist
atenolol Atenolol: A cardioselective beta-1 adrenergic blocker possessing properties and potency similar to PROPRANOLOL, but without a negative inotropic effect.. atenolol : An ethanolamine compound having a (4-carbamoylmethylphenoxy)methyl group at the 1-position and an N-isopropyl substituent.	2.07	1	0	ethanolamines; monocarboxylic acid amide; propanolamine	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; sympatholytic agent; xenobiotic
azinphosmethyl Azinphosmethyl: An organothiophosphorus cholinesterase inhibitor. It has been used as an acaricide and as an insecticide.. azinphos-methyl : A member of the class of benzotriazines that is 1,2,3-benzotriazine substituted by an oxo group at position 4 and a [(dimethoxyphosphorothioyl)sulfanyl]methyl group at position 3.	2.08	1	0	benzotriazines; organic thiophosphate; organothiophosphate insecticide	agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor
mellitic acid mellitic acid: RN given refers to parent cpd; structure. mellitic acid : A benzene-derived hexacarboxylic acid in which each carbon of benzene carries a carboxy substituent.	1.98	1	0	hexacarboxylic acid
beta-naphthoflavone beta-Naphthoflavone: A polyaromatic hydrocarbon inducer of P4501A1 and P4501A2 cytochromes. (Proc Soc Exp Biol Med 1994 Dec:207(3):302-308). beta-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the f side of flavone.	1.99	1	0	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist
bay h 4502 bifonazole : A racemate comprising equimolar amounts of R- and S-bifonazole. It is a broad spectrum antifungal drug used for the treatment of fungal skin and nail infections.. 1-[biphenyl-4-yl(phenyl)methyl]imidazole : A member of the class of imidazoles carrying an alpha-(biphenyl-4-yl)benzyl substituent at position 1.	2.03	1	0	biphenyls; imidazoles
bisbenzimidazole Bisbenzimidazole: A benzimidazole antifilarial agent; it is fluorescent when it binds to certain nucleotides in DNA, thus providing a tool for the study of DNA replication; it also interferes with mitosis.	9.04	4	0	bibenzimidazole; N-methylpiperazine	anthelminthic drug; fluorochrome
caffeine [no description available]	2.49	2	0	purine alkaloid; trimethylxanthine	adenosine A2A receptor antagonist; adenosine receptor antagonist; adjuvant; central nervous system stimulant; diuretic; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; environmental contaminant; food additive; fungal metabolite; geroprotector; human blood serum metabolite; mouse metabolite; mutagen; plant metabolite; psychotropic drug; ryanodine receptor agonist; xenobiotic
carbamazepine Carbamazepine: A dibenzazepine that acts as a sodium channel blocker. It is used as an anticonvulsant for the treatment of grand mal and psychomotor or focal SEIZURES. It may also be used in the management of BIPOLAR DISORDER, and has analgesic properties.. carbamazepine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine carrying a carbamoyl substituent at the azepine nitrogen, used as an anticonvulsant.	2.25	1	0	dibenzoazepine; ureas	analgesic; anticonvulsant; antimanic drug; drug allergen; EC 3.5.1.98 (histone deacetylase) inhibitor; environmental contaminant; glutamate transporter activator; mitogen; non-narcotic analgesic; sodium channel blocker; xenobiotic
chloroquine Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.	5.42	4	1	aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug
chlorpropamide Chlorpropamide: A sulfonylurea hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. (From Martindale, The Extra Pharmacopoeia, 30th ed, p277). chlorpropamide : An N-sulfonylurea that is urea in which a hydrogen attached to one of the nitrogens is substituted by 4-chlorobenzenesulfonyl group and a hydrogen attached to the other nitrogen is substituted by propyl group. Chlorpropamide is a hypoglycaemic agent used in the treatment of type 2 (non-insulin-dependent) diabetes mellitus not responding to dietary modification.	2.03	1	0	monochlorobenzenes; N-sulfonylurea	hypoglycemic agent; insulin secretagogue
chlorzoxazone Chlorzoxazone: A centrally acting central muscle relaxant with sedative properties. It is claimed to inhibit muscle spasm by exerting an effect primarily at the level of the spinal cord and subcortical areas of the brain. (From Martindale, The Extra Pharmacopoea, 30th ed, p1202). chlorzoxazone : A member of the class of 1,3-benzoxazoles that is 1,3-benzoxazol-2-ol in which the hydrogen atom at position 5 is substituted by chlorine. A centrally acting muscle relaxant with sedative properties, it is used for the symptomatic treatment of painful muscle spasm.	1.97	1	0	1,3-benzoxazoles; heteroaryl hydroxy compound; organochlorine compound	muscle relaxant; sedative
clemizole clemizole: was heading 1966-94 (see under BENZIMIDAZOLES 1966-90); use BENZIMIDAZOLES to search CLEMIZOLE 1966-94; a histamine H1- blocker used to treat allergies. clemizole : A member of the class of benzimidazoles that is 1H-benzimidazole substituted by a pyrrolidin-1-ylmethyl and a 4-chlorobenzyl groups at positions 2 and 1 respectively.	7.08	1	0	benzimidazoles; monochlorobenzenes; pyrrolidines	histamine antagonist
clofibrate angiokapsul: contains clofibrate & insoitolnicotinate	1.97	1	0	aromatic ether; ethyl ester; monochlorobenzenes	anticholesteremic drug; antilipemic drug; geroprotector; PPARalpha agonist
clotrimazole [no description available]	2.03	1	0	conazole antifungal drug; imidazole antifungal drug; imidazoles; monochlorobenzenes	antiinfective agent; environmental contaminant; xenobiotic
dapi DAPI: RN given refers to parent cpd.	7.13	1	0	indoles	fluorochrome
diazepam Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.	2.31	1	0	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; xenobiotic
diclofenac Diclofenac: A non-steroidal anti-inflammatory agent (NSAID) with antipyretic and analgesic actions. It is primarily available as the sodium salt.. diclofenac : A monocarboxylic acid consisting of phenylacetic acid having a (2,6-dichlorophenyl)amino group at the 2-position.	2.78	3	0	amino acid; aromatic amine; dichlorobenzene; monocarboxylic acid; secondary amino compound	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
diethylcarbamazine Diethylcarbamazine: An anthelmintic used primarily as the citrate in the treatment of filariasis, particularly infestations with Wucheria bancrofti or Loa loa.	7.05	1	0	N-carbamoylpiperazine; N-methylpiperazine
benzophenone benzophenone : The simplest member of the class of benzophenones, being formaldehyde in which both hydrogens are replaced by phenyl groups.	7.08	1	0	benzophenones	photosensitizing agent; plant metabolite
stallimycin [no description available]	3.1	1	0
disulfiram [no description available]	3.35	1	0	organic disulfide; organosulfur acaricide	angiogenesis inhibitor; antineoplastic agent; apoptosis inducer; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; EC 3.1.1.1 (carboxylesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; ferroptosis inducer; fungicide; NF-kappaB inhibitor
econazole Econazole: An imidazole derivative that is commonly used as a topical antifungal agent.. econazole : A racemate composed of equimolar amounts of (R)- and (S)-econazole. Used (as its nitrate salt) to treat skin infections such as athlete's foot, jock itch, ringworm and other fungal skin infections.. 1-{2-(4-chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl}imidazole : A member of the class of imidazoles that is 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanol in which the hydroxyl hydrogen is replaced by a 4-chlorobenzyl group.	2.03	1	0	dichlorobenzene; ether; imidazoles; monochlorobenzenes
ethylenediamine ethylenediamine: RN given refers to parent cpd; edamine is the recommended contraction for the ethylenediamine radical. ethylenediamine : An alkane-alpha,omega-diamine in which the alkane is ethane.	2.02	1	0	alkane-alpha,omega-diamine	GABA agonist
fenbendazole Fenbendazole: Antinematodal benzimidazole used in veterinary medicine.. fenbendazole : A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted at positons 2 and 5 by (methoxycarbonyl)amino and phenylsulfanediyl groups, respectively. A broad-spectrum anthelmintic, it is used, particularly in veterinary medicine, for the treatment of nematodal infections.	10.76	11	2	aryl sulfide; benzimidazoles; carbamate ester	antinematodal drug
fluconazole Fluconazole: Triazole antifungal agent that is used to treat oropharyngeal CANDIDIASIS and cryptococcal MENINGITIS in AIDS.. fluconazole : A member of the class of triazoles that is propan-2-ol substituted at position 1 and 3 by 1H-1,2,4-triazol-1-yl groups and at position 2 by a 2,4-difluorophenyl group. It is an antifungal drug used for the treatment of mucosal candidiasis and for systemic infections including systemic candidiasis, coccidioidomycosis, and cryptococcosis.	7.46	2	0	conazole antifungal drug; difluorobenzene; tertiary alcohol; triazole antifungal drug	environmental contaminant; P450 inhibitor; xenobiotic
fluorouracil Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.	2.17	1	0	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
fomepizole Fomepizole: A pyrazole and competitive inhibitor of ALCOHOL DEHYDROGENASE that is used for the treatment of poisoning by ETHYLENE GLYCOL or METHANOL.. fomepizole : A member of the class of pyrazoles that is 1H-pyrazole substituted by a methyl group at position 4.	2	1	0	pyrazoles	antidote; EC 1.1.1.1 (alcohol dehydrogenase) inhibitor; protective agent
2,5-dihydroxybenzoic acid 2,5-dihydroxybenzoic acid: RN given refers to parent cpd; a oxidative product of saligenin. 2,5-dihydroxybenzoic acid : A dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions.	2.07	1	0	dihydroxybenzoic acid	EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; fungal metabolite; human metabolite; MALDI matrix material; mouse metabolite
guanidine Guanidine: A strong organic base existing primarily as guanidium ions at physiological pH. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed) It is also used in the treatment of myasthenia and as a fluorescent probe in HPLC.. guanidine : An aminocarboxamidine, the parent compound of the guanidines.	2.34	2	0	carboxamidine; guanidines; one-carbon compound
fasudil fasudil: intracellular calcium antagonist; structure in first source. fasudil : An isoquinoline substituted by a (1,4-diazepan-1-yl)sulfonyl group at position 5. It is a Rho-kinase inhibitor and its hydrochloride hydrate form is approved for the treatment of cerebral vasospasm and cerebral ischemia.	2.06	1	0	isoquinolines; N-sulfonyldiazepane	antihypertensive agent; calcium channel blocker; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; geroprotector; neuroprotective agent; nootropic agent; vasodilator agent
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	7.11	1	0	monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; radical scavenger; xenobiotic
isoproterenol Isoproterenol: Isopropyl analog of EPINEPHRINE; beta-sympathomimetic that acts on the heart, bronchi, skeletal muscle, alimentary tract, etc. It is used mainly as bronchodilator and heart stimulant.. isoprenaline : A secondary amino compound that is noradrenaline in which one of the hydrogens attached to the nitrogen is replaced by an isopropyl group. A sympathomimetic acting almost exclusively on beta-adrenergic receptors, it is used (mainly as the hydrochloride salt) as a bronghodilator and heart stimulant for the management of a variety of cardiac disorders.	6.95	1	0	catechols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; sympathomimetic agent
itraconazole [no description available]	2.03	1	0	piperazines
ketoconazole 1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine : A dioxolane that is 1,3-dioxolane which is substituted at positions 2, 2, and 4 by imidazol-1-ylmethyl, 2,4-dichlorophenyl, and [para-(4-acetylpiperazin-1-yl)phenoxy]methyl groups, respectively.	2.03	1	0	dichlorobenzene; dioxolane; ether; imidazoles; N-acylpiperazine; N-arylpiperazine
ketoprofen Ketoprofen: An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It is used in the treatment of rheumatoid arthritis and osteoarthritis.. ketoprofen : An oxo monocarboxylic acid that consists of propionic acid substituted by a 3-benzoylphenyl group at position 2.	3.34	1	1	benzophenones; oxo monocarboxylic acid	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic
lansoprazole Lansoprazole: A 2,2,2-trifluoroethoxypyridyl derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS. Lansoprazole is a racemic mixture of (R)- and (S)-isomers.	7.71	3	0	benzimidazoles; pyridines; sulfoxide	anti-ulcer drug; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor
losartan Losartan: An antagonist of ANGIOTENSIN TYPE 1 RECEPTOR with antihypertensive activity due to the reduced pressor effect of ANGIOTENSIN II.. losartan : A biphenylyltetrazole where a 1,1'-biphenyl group is attached at the 5-position and has an additional trisubstituted imidazol-1-ylmethyl group at the 4'-position	2.11	1	0	biphenylyltetrazole; imidazoles	angiotensin receptor antagonist; anti-arrhythmia drug; antihypertensive agent; endothelin receptor antagonist
mebendazole Mebendazole: A benzimidazole that acts by interfering with CARBOHYDRATE METABOLISM and inhibiting polymerization of MICROTUBULES.. mebendazole : A carbamate ester that is methyl 1H-benzimidazol-2-ylcarbamate substituted by a benzoyl group at position 5.	12.81	12	2	aromatic ketone; benzimidazoles; carbamate ester	antinematodal drug; microtubule-destabilising agent; tubulin modulator
mechlorethamine nitrogen mustard : Compounds having two beta-haloalkyl groups bound to a nitrogen atom, as in (X-CH2-CH2)2NR.	1.93	1	0	nitrogen mustard; organochlorine compound	alkylating agent
mefenamic acid Mefenamic Acid: A non-steroidal anti-inflammatory agent with analgesic, anti-inflammatory, and antipyretic properties. It is an inhibitor of cyclooxygenase.. mefenamic acid : An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 2,3-dimethylphenyl group. Although classed as a non-steroidal anti-inflammatory drug, its anti-inflammatory properties are considered to be minor. It is used to relieve mild to moderate pain, including headaches, dental pain, osteoarthritis and rheumatoid arthritis.	2.25	1	0	aminobenzoic acid; secondary amino compound	analgesic; antipyretic; antirheumatic drug; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic
mesalamine Mesalamine: An anti-inflammatory agent, structurally related to the SALICYLATES, which is active in INFLAMMATORY BOWEL DISEASE. It is considered to be the active moiety of SULPHASALAZINE. (From Martindale, The Extra Pharmacopoeia, 30th ed). mesalamine : A monohydroxybenzoic acid that is salicylic acid substituted by an amino group at the 5-position.	7.11	1	0	amino acid; aromatic amine; monocarboxylic acid; monohydroxybenzoic acid; phenols	non-steroidal anti-inflammatory drug
methoxyamine methoxyamine: analytical reagent for aldehydes and ketones; strong irritant, can probably produce methemoglobinemia; RN given refers to parent cpd; structure	2	1	0	organooxygen compound
nocodazole [no description available]	2.11	1	0	aromatic ketone; benzimidazoles; carbamate ester; thiophenes	antimitotic; antineoplastic agent; microtubule-destabilising agent; tubulin modulator
metronidazole Metronidazole: A nitroimidazole used to treat AMEBIASIS; VAGINITIS; TRICHOMONAS INFECTIONS; GIARDIASIS; ANAEROBIC BACTERIA; and TREPONEMAL INFECTIONS.. metronidazole : A member of the class of imidazoles substituted at C-1, -2 and -5 with 2-hydroxyethyl, nitro and methyl groups respectively. It has activity against anaerobic bacteria and protozoa, and has a radiosensitising effect on hypoxic tumour cells. It may be given by mouth in tablets, or as the benzoate in an oral suspension. The hydrochloride salt can be used in intravenous infusions. Metronidazole is a prodrug and is selective for anaerobic bacteria due to their ability to intracellularly reduce the nitro group of metronidazole to give nitroso-containing intermediates. These can covalently bind to DNA, disrupting its helical structure, inducing DNA strand breaks and inhibiting bacterial nucleic acid synthesis, ultimately resulting in bacterial cell death.	5.18	8	0	C-nitro compound; imidazoles; primary alcohol	antiamoebic agent; antibacterial drug; antimicrobial agent; antiparasitic agent; antitrichomonal drug; environmental contaminant; prodrug; radiosensitizing agent; xenobiotic
metyrapone Metyrapone: An inhibitor of the enzyme STEROID 11-BETA-MONOOXYGENASE. It is used as a test of the feedback hypothalamic-pituitary mechanism in the diagnosis of CUSHING SYNDROME.. metyrapone : An aromatic ketone that is 3,3-dimethylbutan-2-one in which the methyl groups at positions 1 and 4 are replaced by pyridin-3-yl groups. A steroid 11beta-monooxygenase (EC 1.14.15.4) inhibitor, it is used in the diagnosis of adrenal insufficiency.	1.98	1	0	aromatic ketone	antimetabolite; diagnostic agent; EC 1.14.15.4 (steroid 11beta-monooxygenase) inhibitor
miconazole Miconazole: An imidazole antifungal agent that is used topically and by intravenous infusion.. 1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole : A member of the class of imidazoles that is 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanol in which the hydroxyl hydrogen is replaced by a 2,4-dichlorobenzyl group.. miconazole : A racemate composed of equimolar amounts of (R)- and (S)-miconazole. Used (as its nitrate salt) to treat skin infections such as athlete's foot, jock itch, ringworm and other fungal skin infections. It inhibits the synthesis of ergosterol, a critical component of fungal cell membranes.	2.03	1	0	dichlorobenzene; ether; imidazoles
clorgyline Clorgyline: An antidepressive agent and monoamine oxidase inhibitor related to PARGYLINE.. clorgyline : An aromatic ether that is the 2,4-dichlorophenyl ether of 3-aminopropan-1-ol in which the nitrogen is substituted by a methyl group and a prop-1-yn-3-yl group. A monoamine oxidase inhibitor, it was formerly used as an antidepressant.	2.25	1	0	aromatic ether; dichlorobenzene; terminal acetylenic compound; tertiary amino compound	antidepressant; EC 1.4.3.4 (monoamine oxidase) inhibitor
netropsin Netropsin: A basic polypeptide isolated from Streptomyces netropsis. It is cytotoxic and its strong, specific binding to A-T areas of DNA is useful to genetics research.	3.1	1	0
norfloxacin Norfloxacin: A synthetic fluoroquinolone (FLUOROQUINOLONES) with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin inhibits bacterial DNA GYRASE.. norfloxacin : A quinolinemonocarboxylic acid with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase.	7.08	1	0	fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antibacterial drug; DNA synthesis inhibitor; environmental contaminant; xenobiotic
omeprazole Omeprazole: A 4-methoxy-3,5-dimethylpyridyl, 5-methoxybenzimidazole derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits an H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS.. omeprazole : A racemate comprising equimolar amounts of (R)- and (S)-omeprazole.. 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole : A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted by a [4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl group at position 2 and a methoxy group at position 5.	9.89	6	0	aromatic ether; benzimidazoles; pyridines; sulfoxide
ondansetron Ondansetron: A competitive serotonin type 3 receptor antagonist. It is effective in the treatment of nausea and vomiting caused by cytotoxic chemotherapy drugs, including cisplatin, and has reported anxiolytic and neuroleptic properties.	2.01	1	0	carbazoles
oxonic acid Oxonic Acid: Antagonist of urate oxidase.	2.25	1	0	1,3,5-triazines; monocarboxylic acid
oxibendazole oxibendazole: structure	1.96	1	0	benzimidazoles; carbamate ester
pantoprazole Pantoprazole: 2-pyridinylmethylsulfinylbenzimidazole proton pump inhibitor that is used in the treatment of GASTROESOPHAGEAL REFLUX and PEPTIC ULCER.. pantoprazole : A member of the class of benzimidazoles that is 1H-benzimidazole substituted by a difluoromethoxy group at position 5 and a [(3,4-dimethoxypyridin-2-yl)methyl]sulfinyl group at position 2.	1.99	1	0	aromatic ether; benzimidazoles; organofluorine compound; pyridines; sulfoxide	anti-ulcer drug; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; environmental contaminant; xenobiotic
patulin Patulin: 4-Hydroxy-4H-furo(3,2-c)pyran-2(6H)-one. A mycotoxin produced by several species of Aspergillus and Penicillium. It is found in unfermented apple and grape juice and field crops. It has antibiotic properties and has been shown to be carcinogenic and mutagenic and causes chromosome damage in biological systems.. patulin : A furopyran and lactone that is (2H-pyran-3(6H)-ylidene)acetic acid which is substituted by hydroxy groups at positions 2 and 4 and in which the hydroxy group at position 4 has condensed with the carboxy group to give the corresponding bicyclic lactone. A mycotoxin produced by several species of Aspergillus and Penicillium, it has antibiotic properties but has been shown to be carcinogenic and mutagenic.	2.08	1	0	furopyran; gamma-lactone; lactol	antimicrobial agent; Aspergillus metabolite; carcinogenic agent; mutagen; mycotoxin; Penicillium metabolite
pentamidine Pentamidine: Antiprotozoal agent effective in trypanosomiasis, leishmaniasis, and some fungal infections; used in treatment of PNEUMOCYSTIS pneumonia in HIV-infected patients. It may cause diabetes mellitus, central nervous system damage, and other toxic effects.. pentamidine : A diether consisting of pentane-1,5-diol in which both hydroxyl hydrogens have been replaced by 4-amidinophenyl groups. A trypanocidal drug that is used for treatment of cutaneous leishmaniasis and Chagas disease.	2.98	4	0	aromatic ether; carboxamidine; diether	anti-inflammatory agent; antifungal agent; calmodulin antagonist; chemokine receptor 5 antagonist; EC 2.3.1.48 (histone acetyltransferase) inhibitor; NMDA receptor antagonist; S100 calcium-binding protein B inhibitor; trypanocidal drug; xenobiotic
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.	2.67	3	0	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
piperazine [no description available]	2.4	2	0	azacycloalkane; piperazines; saturated organic heteromonocyclic parent	anthelminthic drug
potassium chloride Potassium Chloride: A white crystal or crystalline powder used in BUFFERS; FERTILIZERS; and EXPLOSIVES. It can be used to replenish ELECTROLYTES and restore WATER-ELECTROLYTE BALANCE in treating HYPOKALEMIA.. potassium chloride : A metal chloride salt with a K(+) counterion.	1.96	1	0	inorganic chloride; inorganic potassium salt; potassium salt	fertilizer
4-aminobenzoic acid para-Aminobenzoates: Benzoic acids, salts, or esters that contain an amino group attached to carbon number 4 of the benzene ring structure.. 4-aminobenzoate : An aromatic amino-acid anion that is the conjugate base of 4-aminobenzoic acid.	2.06	1	0	aminobenzoate; aromatic amino-acid anion	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
praziquantel azinox: Russian drug	7.05	5	2	isoquinolines
proadifen Proadifen: An inhibitor of drug metabolism and CYTOCHROME P-450 ENZYME SYSTEM activity.	2.39	2	0	diarylmethane
propafenone Propafenone: An antiarrhythmia agent that is particularly effective in ventricular arrhythmias. It also has weak beta-blocking activity.. propafenone : An aromatic ketone that is 3-(propylamino)propane-1,2-diol in which the hydrogen of the primary hydroxy group is replaced by a 2-(3-phenylpropanoyl)phenyl group. It is a class 1C antiarrhythmic drug with local anesthetic effects, and is used as the hydrochloride salt in the management of supraventricular and ventricular arrhythmias.	2.03	1	0	aromatic ketone; secondary alcohol; secondary amino compound	anti-arrhythmia drug
propranolol Propranolol: A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs.. propranolol : A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.	2.42	2	0	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic
rabeprazole Rabeprazole: A 4-(3-methoxypropoxy)-3-methylpyridinyl derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS.	2.42	2	0	benzimidazoles; pyridines; sulfoxide	anti-ulcer drug; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor
salicylamide salamide: a major impurity of hydrochlorothiazide; structure in first source	2.06	1	0	phenols; salicylamides	antirheumatic drug; non-narcotic analgesic
sulfanilamide [no description available]	1.93	1	0	substituted aniline; sulfonamide antibiotic; sulfonamide	antibacterial agent; drug allergen; EC 4.2.1.1 (carbonic anhydrase) inhibitor
sulfaphenazole Sulfaphenazole: A sulfonilamide anti-infective agent.. sulfaphenazole : A sulfonamide that is sulfanilamide in which the sulfonamide nitrogen is substituted by a 1-phenyl-1H-pyrazol-5-yl group. It is a selective inhibitor of cytochrome P450 (CYP) 2C9 isozyme, and antibacterial agent.	2.03	1	0	primary amino compound; pyrazoles; substituted aniline; sulfonamide antibiotic; sulfonamide	antibacterial drug; EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor; EC 1.14.13.67 (quinine 3-monooxygenase) inhibitor; P450 inhibitor
sulfinpyrazone Sulfinpyrazone: A uricosuric drug that is used to reduce the serum urate levels in gout therapy. It lacks anti-inflammatory, analgesic, and diuretic properties.	2.03	1	0	pyrazolidines; sulfoxide	uricosuric drug
temozolomide [no description available]	2.13	1	0	imidazotetrazine; monocarboxylic acid amide; triazene derivative	alkylating agent; antineoplastic agent; prodrug
thiabendazole Tresaderm: dermatologic soln containing dexamethasone, thiabendazole & neomycin sulfate	3.69	10	0	1,3-thiazoles; benzimidazole fungicide; benzimidazoles	antifungal agrochemical; antinematodal drug
2,4-thiazolidinedione thiazolidine-2,4-dione: structure in first source. 1,3-thiazolidine-2,4-dione : A thiazolidenedione carrying oxo substituents at positions 2 and 4.	2.15	1	0	thiazolidenedione
tinidazole Tinidazole: A nitroimidazole alkylating agent that is used as an antitrichomonal agent against TRICHOMONAS VAGINALIS; ENTAMOEBA HISTOLYTICA; and GIARDIA LAMBLIA infections. It also acts as an antibacterial agent for the treatment of BACTERIAL VAGINOSIS and anaerobic bacterial infections.. tinidazole : 1H-imidazole substituted at C-1 by a (2-ethylsulfonyl)ethyl group, at C-2 by a methyl group and at C-5 by a nitro group. It is used as an antiprotozoal, antibacterial agent.	4.24	2	0	imidazoles	antiamoebic agent; antibacterial drug; antiparasitic agent; antiprotozoal drug
tolbutamide Tolbutamide: A sulphonylurea hypoglycemic agent with actions and uses similar to those of CHLORPROPAMIDE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p290). tolbutamide : An N-sulfonylurea that consists of 1-butylurea having a tosyl group attached at the 3-position.	2.03	1	0	N-sulfonylurea	human metabolite; hypoglycemic agent; insulin secretagogue; potassium channel blocker
tolnaftate [no description available]	2.03	1	0	monothiocarbamic ester	antifungal drug
trimethoprim Trimethoprim: A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM, SULFAMETHOXAZOLE DRUG COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported.. trimethoprim : An aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge.	7.07	1	0	aminopyrimidine; methoxybenzenes	antibacterial drug; diuretic; drug allergen; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; environmental contaminant; xenobiotic
2-hydroxybenzylbenzimidazole 2-hydroxybenzylbenzimidazole: RN given refers to cpd without isomeric designation	1.96	1	0
carbachol Carbachol: A slowly hydrolyzed CHOLINERGIC AGONIST that acts at both MUSCARINIC RECEPTORS and NICOTINIC RECEPTORS.	2.01	1	0	ammonium salt; carbamate ester	cardiotonic drug; miotic; muscarinic agonist; nicotinic acetylcholine receptor agonist; non-narcotic analgesic
trichlorfon Trichlorfon: An organochlorophosphate cholinesterase inhibitor that is used as an insecticide for the control of flies and roaches. It is also used in anthelmintic compositions for animals. (From Merck, 11th ed). trichlorfon : A phosphonic ester that is dimethyl phosphonate in which the hydrogen atom attched to the phosphorous is substituted by a 2,2,2-trichloro-1-hydroxyethyl group.	1.97	1	0	organic phosphonate; organochlorine compound; phosphonic ester	agrochemical; anthelminthic drug; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; insecticide
methylprednisolone acetate Methylprednisolone Acetate: Methylprednisolone derivative that is used as an anti-inflammatory agent for the treatment of ALLERGY and ALLERGIC RHINITIS; ASTHMA; and BURSITIS; and for the treatment of ADRENAL INSUFFICIENCY.. methylprednisolone acetate : An acetate ester resulting from the formal condensation of the 21-hydroxy function of 6alpha-methylprednisolone compound with acetic acid.	2.06	1	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 3-oxo-Delta(1),Delta(4)-steroid; acetate ester; glucocorticoid; steroid ester; tertiary alpha-hydroxy ketone	anti-inflammatory drug
dehydroepiandrosterone Dehydroepiandrosterone: A major C19 steroid produced by the ADRENAL CORTEX. It is also produced in small quantities in the TESTIS and the OVARY. Dehydroepiandrosterone (DHEA) can be converted to TESTOSTERONE; ANDROSTENEDIONE; ESTRADIOL; and ESTRONE. Most of DHEA is sulfated (DEHYDROEPIANDROSTERONE SULFATE) before secretion.. dehydroepiandrosterone : An androstanoid that is androst-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 17. It is a naturally occurring steroid hormone produced by the adrenal glands.	2.21	1	0	17-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; androstanoid	androgen; human metabolite; mouse metabolite
alanine Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.	2.93	4	0	alanine zwitterion; alanine; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid	EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor; fundamental metabolite
serine Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.	2.7	3	0	L-alpha-amino acid; proteinogenic amino acid; serine family amino acid; serine zwitterion; serine	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	6.93	1	0	C-nitro compound; carboxamide; diol; organochlorine compound	antibacterial drug; antimicrobial agent; Escherichia coli metabolite; geroprotector; Mycoplasma genitalium metabolite; protein synthesis inhibitor
aspartic acid Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.	2	1	0	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
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.	7.38	2	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
cyanides Cyanides: Inorganic salts of HYDROGEN CYANIDE containing the -CN radical. The concept also includes isocyanides. It is distinguished from NITRILES, which denotes organic compounds containing the -CN radical.. cyanides : Salts and C-organyl derivatives of hydrogen cyanide, HC#N.. isocyanide : The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)).. cyanide : A pseudohalide anion that is the conjugate base of hydrogen cyanide.	2.96	4	0	pseudohalide anion	EC 1.9.3.1 (cytochrome c oxidase) inhibitor
physostigmine Physostigmine: A cholinesterase inhibitor that is rapidly absorbed through membranes. It can be applied topically to the conjunctiva. It also can cross the blood-brain barrier and is used when central nervous system effects are desired, as in the treatment of severe anticholinergic toxicity.	2.08	1	0	carbamate ester; indole alkaloid	antidote to curare poisoning; EC 3.1.1.8 (cholinesterase) inhibitor; miotic
2,3,4,6-tetrachlorophenol 2,3,4,6-tetrachlorophenol: RN given refers to parent cpd; see also record for tetrachlorophenol with locants for chloro groups not specified. 2,3,4,6-tetrachlorophenol : A tetrachlorophenol in which the chlorines are located at positions 2, 3, 4, and 6.	2.04	1	0	tetrachlorophenol	xenobiotic metabolite
uridine diphosphate Uridine Diphosphate: A uracil nucleotide containing a pyrophosphate group esterified to C5 of the sugar moiety.	2.17	1	0	pyrimidine ribonucleoside 5'-diphosphate; uridine 5'-phosphate	Escherichia coli metabolite; mouse metabolite
carbostyril Quinolones: A group of derivatives of naphthyridine carboxylic acid, quinoline carboxylic acid, or NALIDIXIC ACID.. quinolin-2(1H)-one : A quinolone that is 1,2-dihydroquinoline substituted by an oxo group at position 2.	3.56	2	0	monohydroxyquinoline; quinolone	bacterial xenobiotic metabolite
phenylephrine Phenylephrine: An alpha-1 adrenergic agonist used as a mydriatic, nasal decongestant, and cardiotonic agent.. phenylephrine : A member of the class of the class of phenylethanolamines that is (1R)-2-(methylamino)-1-phenylethan-1-ol carrying an additional hydroxy substituent at position 3 on the phenyl ring.	2.07	1	0	phenols; phenylethanolamines; secondary amino compound	alpha-adrenergic agonist; cardiotonic drug; mydriatic agent; nasal decongestant; protective agent; sympathomimetic agent; vasoconstrictor agent
benzoxazolone benzoxazolone: RN given refers to parent cpd; structure. 2-benzoxazolinone : A member of the class of benzoxazoles that is 2,3-dihydro-1,3-benzoxazole carrying an oxo group at position 2.	2.11	1	0	benzoxazole	allelochemical; phytoalexin
edetic acid Edetic Acid: A chelating agent that sequesters a variety of polyvalent cations such as CALCIUM. It is used in pharmaceutical manufacturing and as a food additive.	2.01	1	0	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	7.97	4	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
cysteamine Cysteamine: A mercaptoethylamine compound that is endogenously derived from the COENZYME A degradative pathway. The fact that cysteamine is readily transported into LYSOSOMES where it reacts with CYSTINE to form cysteine-cysteamine disulfide and CYSTEINE has led to its use in CYSTINE DEPLETING AGENTS for the treatment of CYSTINOSIS.. cysteamine : An amine that consists of an ethane skeleton substituted with a thiol group at C-1 and an amino group at C-2.	2.02	1	0	amine; thiol	geroprotector; human metabolite; mouse metabolite; radiation protective agent
adenosine monophosphate Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.	2.05	1	0	adenosine 5'-phosphate; purine ribonucleoside 5'-monophosphate	adenosine A1 receptor agonist; cofactor; EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.11 (fructose-bisphosphatase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
zoxazolamine Zoxazolamine: A uricosuric and muscle relaxant. Zoxazolamine acts centrally as a muscle relaxant, but the mechanism of its action is not understood.	1.97	1	0	benzoxazole
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.	10.39	11	11	amino acid zwitterion; L-alpha-amino acid; leucine; proteinogenic amino acid; pyruvate family amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
ethyl methanesulfonate Ethyl Methanesulfonate: An antineoplastic agent with alkylating properties. It also acts as a mutagen by damaging DNA and is used experimentally for that effect.. ethyl methanesulfonate : A methanesulfonate ester resulting from the formal condensation of methanesulfonic acid with ethanol.	1.97	1	0	methanesulfonate ester	alkylating agent; antineoplastic agent; carcinogenic agent; genotoxin; mutagen; teratogenic agent
aniline [no description available]	2.75	3	0	anilines; primary arylamine
methionine Methionine: A sulfur-containing essential L-amino acid that is important in many body functions.. methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4.	7.1	1	0	aspartate family amino acid; L-alpha-amino acid; methionine zwitterion; methionine; proteinogenic amino acid	antidote to paracetamol poisoning; human metabolite; micronutrient; mouse metabolite; nutraceutical
phenylalanine Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.	2.49	2	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; phenylalanine; proteinogenic amino acid	algal metabolite; EC 3.1.3.1 (alkaline phosphatase) inhibitor; Escherichia coli metabolite; human xenobiotic metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
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.	2.97	4	0	alkaloid; colchicine	anti-inflammatory agent; gout suppressant; mutagen
ampicillin Ampicillin: Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.. ampicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group.	2.05	1	0	beta-lactam antibiotic; penicillin allergen; penicillin	antibacterial drug
histidine Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.	3.44	7	0	amino acid zwitterion; histidine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
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.	2.03	1	0	amino acid zwitterion; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid; threonine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
tryptophan Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.	7.43	2	0	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
4-chlorobenzoic acid 4-chlorobenzoic acid: RN given refers to parent cpd. 4-chlorobenzoic acid : A monochlorobenzoic acid carrying a chloro substituent at position 4.	2	1	0	monochlorobenzoic acid	bacterial xenobiotic metabolite
acetylene [no description available]	2.21	1	0	alkyne; gas molecular entity; terminal acetylenic compound
methylamine methyl group : An alkyl group that is the univalent group derived from methane by removal of a hydrogen atom.	2.05	1	0	methylamines; one-carbon compound; primary aliphatic amine	mouse metabolite
boranes Boranes: The collective name for the boron hydrides, which are analogous to the alkanes and silanes. Numerous boranes are known. Some have high calorific values and are used in high-energy fuels. (From Grant & Hackh's Chemical Dictionary, 5th ed). borane : The simplest borane, consisting of a single boron atom carrying three hydrogens.. boranes : The molecular hydrides of boron.	2.05	1	0	boranes; mononuclear parent hydride
propane Propane: A three carbon alkane with the formula H3CCH2CH3.	2.01	1	0	alkane; gas molecular entity	food propellant
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	2.05	1	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
cyclopropane cyclopropane : A cycloalkane composed of three carbon atoms to form a ring.	2.01	1	0	cycloalkane; cyclopropanes	inhalation anaesthetic
fluoroform fluoroform: structure	2.04	1	0	fluoromethanes	refrigerant
methylprednisolone Methylprednisolone: A PREDNISOLONE derivative with similar anti-inflammatory action.. 6alpha-methylprednisolone : The 6alpha-stereoisomer of 6-methylprednisolone.	2.06	1	0	6-methylprednisolone; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antiemetic; environmental contaminant; neuroprotective agent; xenobiotic
phthalimide phthalimide: RN given refers to parent cpd. phthalimide : A dicarboximide that is 2,3-dihydro-1H-isoindole substituted by oxo groups at positions 1 and 3.	7.08	1	0	phthalimides
carbazole carbazole: structure in first source	2.51	2	0	carbazole
2,4-dinitrobenzenesulfonic acid 2,4-dinitrobenzenesulfonic acid: RN given refers to parent cpd; structure. 2,4-dinitrobenzenesulfonic acid : The arenesulfonic acid that is benzenesulfonic acid with two nitro substituents in the 2- and 4-positions.	2.21	1	0	arenesulfonic acid; C-nitro compound
salicylaldehyde o-hydroxybenzaldehyde: structure in first source	7.11	1	0	hydroxybenzaldehyde	nematicide; plant metabolite
bicyclohexanone bicyclohexanone: structure	2.21	1	0
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	15.59	15	11	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
quinoline [no description available]	3.58	8	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinolines
diphenyl diphenyl: RN given refers to unlabeled cpd; structure	2.48	2	0	aromatic fungicide; benzenes; biphenyls	antifungal agrochemical; antimicrobial food preservative
phenothiazine 10H-phenothiazine : The 10H-tautomer of phenothiazine.	3.41	1	0	phenothiazine	ferroptosis inhibitor; plant metabolite; radical scavenger
piperonylic acid piperonylic acid: RN given refers to parent cpd; structure. piperonylic acid : A member of the class of benzodioxoles that is 1,3-benzodioxole substituted by a carboxy group at position 5. It is a natural product isolated from several plant species. It is a selective mechanism-based inactivator of the trans-cinnamate 4-hydroxylase enzyme and exhibits antifungal and skin wound healing properties.	2.07	1	0	aromatic carboxylic acid; benzodioxoles; monocarboxylic acid	antifungal agent; EC 1.14.14.91 ( trans-cinnamate 4-monooxygenase) inhibitor; plant metabolite; vulnerary
benzotriazole benzotriazole: inhibitor of atmospheric metal corrosion; also component of motion picture film & Neva brake fluid. benzotriazole : The simplest member of the class of benzotriazoles that consists of a benzene nucleus fused to a 1H-1,2,3-triazole ring.	4.18	16	0	benzotriazoles	environmental contaminant; xenobiotic
benzothiophene [no description available]	7.72	3	0	1-benzothiophenes; benzothiophene
benzothiazole benzothiazole: structure. benzothiazole : An organic heterobicyclic compound that is a fusion product between benzene and thiazole. The parent of the class of benzothiazoles.	5.87	17	0	benzothiazoles	environmental contaminant; plant metabolite; xenobiotic
1,2-diaminobenzene 1,2-diaminobenzene: RN given refers to parent cpd. 1,2-phenylenediamine : A phenylenediamine in which the two amino groups are ortho to each other.	3.16	5	0	phenylenediamine	hydrogen donor
styrene oxide styrene oxide: structure. styrene oxide : An epoxide that is oxirane in which one of the hydrogens has been replaced by a phenyl group.	2.03	1	0	epoxide	human xenobiotic metabolite
n-methylpyrrole [no description available]	2.02	1	0	pyrroles
lactobionic acid [no description available]	2.11	1	0	disaccharide	antioxidant
benzenesulfonic acid benzenesulfonic acid: RN given refers to parent cpd. benzenesulfonic acid : The simplest member of the class of a benzenesulfonic acids that consists of a benzene carrying a single sulfo group.	2.08	1	0	benzenesulfonic acids
pyrrolidonecarboxylic acid Pyrrolidonecarboxylic Acid: A cyclized derivative of L-GLUTAMIC ACID. Elevated blood levels may be associated with problems of GLUTAMINE or GLUTATHIONE metabolism.. 5-oxo-L-proline : An optically active form of 5-oxoproline having L-configuration.	2.31	1	0	5-oxoproline; L-proline derivative; non-proteinogenic L-alpha-amino acid	algal metabolite
acetophenone acetophenone : A methyl ketone that is acetone in which one of the methyl groups has been replaced by a phenyl group.	2.44	2	0	acetophenones	animal metabolite; photosensitizing agent; xenobiotic
trehalose alpha,alpha-trehalose : A trehalose in which both glucose residues have alpha-configuration at the anomeric carbon.	1.96	1	0	trehalose	Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
benzyl bromide benzyl bromide: structure given in first source. benzyl bromide : A member of the class of benzyl bromides that is toluene substituted on the alpha-carbon with bromine.	2.03	1	0	benzyl bromides	lachrymator
ethylbenzene [no description available]	7	1	0	alkylbenzene
styrene Styrene: A colorless, toxic liquid with a strong aromatic odor. It is used to make rubbers, polymers and copolymers, and polystyrene plastics.. styrene : A vinylarene that is benzene carrying a vinyl group. It has been isolated from the benzoin resin produced by Styrax species.	2.06	1	0	styrenes; vinylarene; volatile organic compound	mouse metabolite; mutagen; plant metabolite
benzylamine aminotoluene : Any member of the class of toluenes carrying one or more amino groups.	2.03	1	0	aralkylamine; primary amine	allergen; EC 3.5.5.1 (nitrilase) inhibitor; plant metabolite
phenyl ether diphenyl ether : An aromatic ether in which the oxygen is attached to two phenyl substituents. It has been found in muscat grapes and vanilla.	2.03	1	0	aromatic ether	plant metabolite
acrylonitrile [no description available]	3.02	4	0	aliphatic nitrile; volatile organic compound	antifungal agent; carcinogenic agent; fungal metabolite; mutagen; polar aprotic solvent
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	2.1	1	0	alkane
3-hydroxybutanal [no description available]	2.08	1	0
melamine melamine: RN given refers to parent cpd; structure. melamine : A trimer of cyanamide, with a 1,3,5-triazine skeleton.	2.1	1	0	triamino-1,3,5-triazine	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.	2.11	1	0	cyclohexanols; secondary alcohol	solvent
thiophenol thiophenol : A thiol in which the sulfanyl group is attached to a phenyl group.	2.21	1	0	aryl thiol
3-hydroxypyridine 3-hydroxypyridine: RN given refeirs to parent cpd. 3-pyridinol : A monohydroxypyridine that is pyridine in which the hydrogen at position 3 has been replaced by a hydroxy group. It has been detected as a thermal degradation product from the smoke of the burning leaves of Salvia divinorum, a Mexican psychoactive plant.	2.07	1	0	monohydroxypyridine
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.	8.56	8	0	pyrrole; secondary amine
furan furan : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing four carbons and one oxygen, with formula C4H4O. It is a toxic, flammable, low-boiling (31degreeC) colourless liquid.	2.21	1	0	furans; mancude organic heteromonocyclic parent; monocyclic heteroarene	carcinogenic agent; hepatotoxic agent; Maillard reaction product
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	3.62	8	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
n-hexane hexane : An unbranched alkane containing six carbon atoms.	2.1	1	0	alkane; volatile organic compound	neurotoxin; non-polar solvent
cyclohexane Cyclohexane: C6H12. cyclohexane : An alicyclic hydrocarbon comprising a ring of six carbon atoms; the cyclic form of hexane, used as a raw material in the manufacture of nylon.	2.08	1	0	cycloalkane; volatile organic compound	non-polar solvent
trinitrotoluene Trinitrotoluene: A 2,4,6-trinitrotoluene, which is an explosive chemical that can cause skin irritation and other toxic consequences.. 2,4,6-trinitrotoluene : A trinitrotoluene having the nitro groups at positions 2, 4 and 6.	7.08	1	0	trinitrotoluene	explosive
framycetin Framycetin: A component of NEOMYCIN that is produced by Streptomyces fradiae. On hydrolysis it yields neamine and neobiosamine B. (From Merck Index, 11th ed). framycetin : A tetracyclic antibacterial agent derived from neomycin, being a glycoside ester of neamine and neobiosamine B.	2.51	2	0	aminoglycoside	allergen; antibacterial drug; Escherichia coli metabolite
1-hydroxyphthalazine 1-hydroxyphthalazine: RN given refers to cpd with unspecified locants; do not confuse with cpd phthalazinol RN: 56611-65-5	2.07	1	0	phthalazines
isoquinoline [no description available]	2.76	3	0	azaarene; isoquinolines; mancude organic heterobicyclic parent; ortho-fused heteroarene
2-naphthol 2-naphthol: RN given refers to parent cpd. 2-naphthol : A naphthol carrying a hydroxy group at position 2.. naphthols : Any hydroxynaphthalene derivative that has a single hydroxy substituent.	2.77	3	0	naphthol	antinematodal drug; genotoxin; human urinary metabolite; human xenobiotic metabolite; mouse metabolite; radical scavenger
2-aminobenzothiazole [no description available]	2.08	1	0	benzothiazoles
2-hydroxypyridine hydroxypyridine : Any member of the class of pyridines with at least one hydroxy substituent.. pyridin-2-ol : A monohydroxypyridine that is pyridine substituted by a hydroxy group at position 2.	2.1	1	0	monohydroxypyridine	plant metabolite
pregnenolone [no description available]	2.03	1	0	20-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; C21-steroid	human metabolite; mouse 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.	2.17	1	0	dithiocarbamic acids	chelator; copper chelator
potassium cyanide [no description available]	1.96	1	0	cyanide salt; one-carbon compound; potassium salt	EC 1.15.1.1 (superoxide dismutase) inhibitor; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; neurotoxin
perylene Perylene: A 20-carbon dibenz(de,kl)anthracene that can be viewed as a naphthalene fused to a phenalene or as dinaphthalene. It is used as fluorescent lipid probe in the cytochemistry of membranes and is a polycyclic hydrocarbon pollutant in soil and water. Derivatives may be carcinogenic.. perylene : An ortho- and peri-fused polycyclic arene comprising of five benzene rings that is anthracene in which the d,e and k,l sides are fused to benzene rings.	7.1	1	0	ortho- and peri-fused polycyclic arene; perylenes
quinazolines Quinazolines: A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.. quinazoline : A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.. quinazolines : Any organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.	9.05	13	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
acridines Acridines: Compounds that include the structure of acridine.. acridine : A polycyclic heteroarene that is anthracene in which one of the central CH groups is replaced by a nitrogen atom.	3.55	2	0	acridines; mancude organic heterotricyclic parent; polycyclic heteroarene	genotoxin
5-azaindole [no description available]	2.11	1	0
indazoles Indazoles: A group of heterocyclic aromatic organic compounds consisting of the fusion of BENZENE and PYRAZOLES.	3.64	9	0	indazole
benzofuran benzofuran: RN & structure given in first source. 1-benzofuran : A benzofuran consisting of fused benzene and furan rings. It is the parent compound of the class of 1-benzofurans.	2.46	2	0	1-benzofurans; benzofuran
4-azaindole [no description available]	2.5	2	0
benzoxazoles 1,3-benzoxazole : A benzoxazole in which the benzene ring is fused to a 1,3-oxazole ring across positions 4 and 5.. benzoxazole : Compounds based on a fused 1,2- or 1,3-oxazole and benzene bicyclic ring skeleton.	5.65	22	0	1,3-benzoxazoles; mancude organic heterobicyclic parent
adamantane Adamantane: A tricyclo bridged hydrocarbon.	2.31	1	0	adamantanes; polycyclic alkane
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	2.69	2	0	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
isoxazoles Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.	7.75	3	0	isoxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
oxazoles Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.	2.5	2	0	1,3-oxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiazoles [no description available]	5.61	13	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
1,2,4-triazole 1,2,4-triazole: RN given refers to 1H-1,2,4-triazole	2.08	1	0	1,2,4-triazole
pyridazine pyridazine: structure given in first source	3.9	3	0	diazine; pyridazines
pyrimidine pyrimidine : The parent compound of the pyrimidines; a diazine having the two nitrogens at the 1- and 3-positions.	3.33	6	0	diazine; pyrimidines	Daphnia magna metabolite
pyrazines Pyrazines: A heterocyclic aromatic organic compound with the chemical formula C4H4N2.. pyrazine : A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms.	2.94	4	0	diazine; pyrazines	Daphnia magna metabolite
hydrazine diamine : Any polyamine that contains two amino groups.	8.48	7	0	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
aminoimidazole carboxamide Aminoimidazole Carboxamide: An imidazole derivative which is a metabolite of the antineoplastic agents BIC and DIC. By itself, or as the ribonucleotide, it is used as a condensation agent in the preparation of nucleosides and nucleotides. Compounded with orotic acid, it is used to treat liver diseases.. 5-aminoimidazole-4-carboxamide : An aminoimidazole in which the amino group is at C-5 with a carboxamido group at C-4.	2.73	3	0	aminoimidazole; monocarboxylic acid amide	mouse metabolite
2-aminopurine 2-Aminopurine: A purine that is an isomer of ADENINE (6-aminopurine).. aminopurine : Any purine having at least one amino substituent.. 2-aminopurine : The parent compound of the 2-aminopurines, comprising a purine core carrying an amino substituent at the 2-position.	1.93	1	0	2-aminopurines; nucleobase analogue	antimetabolite
hydantoins Hydantoins: Compounds based on imidazolidine dione. Some derivatives are ANTICONVULSANTS.. imidazolidine-2,4-dione : An imidazolidinone with oxo groups at position 2 and 4.	2.74	3	0	imidazolidine-2,4-dione
fluorobenzenes Fluorobenzenes: Derivatives of BENZENE that contain FLUORINE.. monofluorobenzene : The simplest member of the class of monofluorobenzenes that is benzene carrying a single fluoro substituent.. fluorobenzenes : Any fluoroarene that is a benzene or a substituted benzene carrying at least one fluoro group.	2.02	1	0	monofluorobenzenes	NMR chemical shift reference compound
ketene ketene: structure. ketene : Carbonyl compounds where the C=O bond is conjugated to an alkylidene group.	7.13	1	0	ketene
propiolic acid propiolic acid: RN given refers to parent cpd; structure. propynoic acid : A terminal acetylenic compound that is a 3-carbon, straight-chain, monounsaturated fatty acid having one acetylenic bond.	2.03	1	0	acetylenic fatty acid; alpha,beta-unsaturated monocarboxylic acid; monounsaturated fatty acid; short-chain fatty acid; terminal acetylenic compound	xenobiotic metabolite
emetine Emetine: The principal alkaloid of ipecac, from the ground roots of Uragoga (or Cephaelis) ipecacuanha or U. acuminata, of the Rubiaceae. It is used as an amebicide in many different preparations and may cause serious cardiac, hepatic, or renal damage and violent diarrhea and vomiting. Emetine inhibits protein synthesis in EUKARYOTIC CELLS but not PROKARYOTIC CELLS.. emetine : A pyridoisoquinoline comprising emetam having methoxy substituents at the 6'-, 7'-, 10- and 11-positions. It is an antiprotozoal agent and emetic. It inhibits SARS-CoV2, Zika and Ebola virus replication and displays antimalarial, antineoplastic and antiamoebic properties.	2.17	1	0	isoquinoline alkaloid; pyridoisoquinoline	antiamoebic agent; anticoronaviral agent; antiinfective agent; antimalarial; antineoplastic agent; antiprotozoal drug; antiviral agent; autophagy inhibitor; emetic; expectorant; plant metabolite; protein synthesis inhibitor
benzohydroxamic acid [no description available]	2.03	1	0
indan indan: structure in first source. indane : An ortho-fused bicyclic hydrocarbon consisting of a benzene ring fused to a cyclopentane ring; a high-boiling (176 (o)C) colourless liquid.	2.08	1	0	indanes; ortho-fused bicyclic hydrocarbon
indoline indoline: structure given in first source	2.42	2	0	indoles
dipicolinic acid dipicolinic acid : A pyridinedicarboxylic acid carrying two carboxy groups at positions 2 and 6.	2.01	1	0	pyridinedicarboxylic acid	bacterial metabolite
oxetane oxetane: structure. oxetane : A saturated organic heteromonocyclic parent that is a four-membered ring comprising of three carbon atoms and an oxygen atom.	7.11	1	0	oxetanes; saturated organic heteromonocyclic parent
alpha-aminopyridine alpha-aminopyridine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #485. aminopyridine : Compounds containing a pyridine skeleton substituted by one or more amine groups.	2.11	1	0
thiazolidines Thiazolidines: Reduced (protonated) form of THIAZOLES. They can be oxidized to THIAZOLIDINEDIONES.	2.05	1	0	thiazolidine
podophyllotoxin Podophyllum: A genus of poisonous American herbs, family BERBERIDACEAE. The roots yield PODOPHYLLOTOXIN and other pharmacologically important agents. The plant was formerly used as a cholagogue and cathartic. It is different from the European mandrake, MANDRAGORA.	2	1	0	furonaphthodioxole; lignan; organic heterotetracyclic compound	antimitotic; antineoplastic agent; keratolytic drug; microtubule-destabilising agent; plant metabolite; tubulin modulator
tryptophol tryptophol : An indolyl alcohol that is ethanol substituted by a 1H-indol-3-yl group at position 2.	2.07	1	0	indolyl alcohol	auxin; plant metabolite; Saccharomyces cerevisiae metabolite
gluconic acid gluconic acid: zinc gluconate has anti-inflammatory activity; RN given refers to (D)-isomer; all RRs refers to (D)-isomer unless otherwise noted. ketogluconic acid : A gluconic acid that contains a ketonic carbonyl group.. D-gluconic acid : A gluconic acid having D-configuration.	2.15	1	0	gluconic acid	chelator; Penicillium metabolite
copper gluconate Gluconates: Derivatives of gluconic acid (the structural formula HOCH2(CHOH)4COOH), including its salts and esters.	2.15	1	0	organic molecular entity
azomycin azomycin: RN given refers to parent cpd with specified locant; structure	4.87	3	0	C-nitro compound; imidazoles	antitubercular agent
aminoacetonitrile Aminoacetonitrile: Cyanomethylamine.	2.48	2	0
maleimide [no description available]	6.94	1	0	dicarboximide; maleimides	EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	2.04	1	0	dialdehyde	biomarker
eosine yellowish-(ys) Eosine Yellowish-(YS): A versatile red dye used in cosmetics, pharmaceuticals, textiles, etc., and as tissue stain, vital stain, and counterstain with HEMATOXYLIN. It is also used in special culture media.. eosin YS dye : An organic sodium salt that is 2',4',5',7'-tetrabromofluorescein in which the carboxy group and the phenolic hydroxy group have been deprotonated and the resulting charge is neutralised by two sodium ions.	2.13	1	0	organic sodium salt; organobromine compound	fluorochrome; histological dye
lucanthone hydrochloride Schistosomicides: Agents that act systemically to kill adult schistosomes.	2.53	2	0
4,4'-bipyridyl 4,4'-bipyridine : A bipyridine in which the two pyridine moieties are linked by a bond between positions C-4 and C-4'.	2.08	1	0	bipyridine
congo red Congo Red: An acid dye used in testing for hydrochloric acid in gastric contents. It is also used histologically to test for AMYLOIDOSIS.. Congo Red : An indicator dye that is blue-violet at pH 3.0 and red at pH 5.0.	2.07	1	0	bis(azo) compound
1-hexene 1-hexene: structure in first source. 1-hexene : An alkene that is hexane carrying a double bond at position 1.	2.01	1	0	alkene
n-methylhydroxylamine [no description available]	2	1	0
methyl carbamate methyl carbamate : A carbamate ester resulting from the formal condensation of the carboxy group of carbamic acid with methanol.	2.81	3	0	carbamate ester
1-methylindole 1-methylindole: SKATOLE refers to 3-methylindole; RN given refers to parent cpd; structure. methylindole : Any member of the class of indoles carrying one or more methyl substituents.	1.97	1	0
5-methylbenzimidazole 5-methylbenzimidazole: structure in first source. 5-methyl-1H-benzimidazole : A member of the class of imidazoles that is 1H-benzimidazole in which the hydrogen at position 5 is substituted by a methyl group.	2.88	4	0	imidazoles
2-methylbenzimidazole [no description available]	3.35	7	0	benzimidazoles
2-hydroxy benzimidazole 2-hydroxy benzimidazole: structure in first source	7.03	1	0
2-iodobenzenamine 2-iodobenzenamine: structure in first source	2.08	1	0
bendazole bendazole: also an NSAID; Russian drug; RN given refers to parent cpd; structure	1.96	1	0	benzimidazoles
erythromycin Erythromycin: A bacteriostatic antibiotic macrolide produced by Streptomyces erythreus. Erythromycin A is considered its major active component. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins.. erythromycin : Any of several wide-spectrum macrolide antibiotics obtained from actinomycete Saccharopolyspora erythraea (formerly known as Streptomyces erythraeus).. erythromycin A : An erythromycin that consists of erythronolide A having 2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl and 3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl residues attahced at positions 4 and 6 respectively.	2.41	2	0	cyclic ketone; erythromycin
formal glycol [no description available]	2.04	1	0	cyclic acetal; dioxolane
2-piperidone 2-piperidone: structure given in first source. piperidin-2-one : A delta-lactam that is piperidine which is substituted by an oxo group at position 2.	2.11	1	0	delta-lactam; piperidones	EC 1.2.1.88 (L-glutamate gamma-semialdehyde dehydrogenase) inhibitor
2-methylimidazole [no description available]	2.11	1	0
2-phenylbenzimidazole 2-phenylbenzimidazole: structure in first source	1.96	1	0
vinblastine [no description available]	2.11	1	0
hexafluoroisopropanol 1,1,1,3,3,3-hexafluoropropan-2-ol : An organofluorine compound formed by substitution of all the methyl protons in propan-2-ol by fluorine. It is a metabolite of inhalation anesthetic sevoflurane.	2.15	1	0	organofluorine compound; secondary alcohol	drug metabolite
2-aminobenzimidazole 2-aminobenzimidazole: metabolite of benomyl; RN given refers to parent cpd. 2-aminobenzimidazole : A member of the class of benzimidazoles that is benzimidazole in which the hydrogen at position 2 is replaced by an amino group.	3.14	5	0	benzimidazoles	marine xenobiotic metabolite
deoxyuridine [no description available]	2.07	1	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
2'-deoxyadenosine 2'-deoxyformycin A: RN not in Chemline 9/85; RN and structure given in first source	2.15	1	0	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
2-phenylpyridine 2-phenylpyridine: structure given in first source	2.21	1	0
pyridine-2-carboxaldehyde pyridine-2-carboxaldehyde: structure in first source. 2-formylpyridine : A pyridinecarbaldehyde that is pyridine in which the hydrogen at position 2 is replaced by a formyl group.	2.08	1	0	pyridinecarbaldehyde
methyl phenyl sulfoxide (methylsulfinyl)benzene : A sulfoxide resulting from the formal oxidation of the sulfur atom of thioanisole.	2.03	1	0	benzenes; sulfoxide
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	2.04	1	0	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
pregnenolone carbonitrile Pregnenolone Carbonitrile: A catatoxic steroid and microsomal enzyme inducer having significant effects on the induction of cytochrome P450. It has also demonstrated the potential for protective capability against acetaminophen-induced liver damage.	1.98	1	0	aliphatic nitrile
nitroxinil Nitroxinil: Proposed anthelmintic for fasciola and liver fluke infestations.	1.97	1	0
2-ethylbenzimidazole [no description available]	2.36	2	0
tetrabutylammonium tetrabutylammonium: lipophilic probe; RN given refers to parent cpd	2.05	1	0	quaternary ammonium ion
phenylguanidine phenylguanidine: RN given refers to parent cpd	2.08	1	0
amiloride Amiloride: A pyrazine compound inhibiting SODIUM reabsorption through SODIUM CHANNELS in renal EPITHELIAL CELLS. This inhibition creates a negative potential in the luminal membranes of principal cells, located in the distal convoluted tubule and collecting duct. Negative potential reduces secretion of potassium and hydrogen ions. Amiloride is used in conjunction with DIURETICS to spare POTASSIUM loss. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p705). amiloride : A member of the class of pyrazines resulting from the formal monoacylation of guanidine with the carboxy group of 3,5-diamino-6-chloropyrazine-2-carboxylic acid.	1.96	1	0	aromatic amine; guanidines; organochlorine compound; pyrazines	diuretic; sodium channel blocker
n-acetylimidazole [no description available]	2.01	1	0	N-acylimidazole
4-nitroimidazole 5-nitroimidazole : A C-nitro compound that is imidazole bearing a nitro substituent at position 5.	4.24	2	0	C-nitro compound; imidazoles
fluorescein-5-isothiocyanate Fluorescein-5-isothiocyanate: Fluorescent probe capable of being conjugated to tissue and proteins. It is used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.. fluorescein 5-isothiocyanate : The 5-isomer of fluorescein isothiocyanate. Acts as a fluorescent probe capable of being conjugated to tissue and proteins; used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.	2.53	2	0	fluorescein isothiocyanate
carbonates Carbonates: Salts or ions of the theoretical carbonic acid, containing the radical CO2(3-). Carbonates are readily decomposed by acids. The carbonates of the alkali metals are water-soluble; all others are insoluble. (From Grant & Hackh's Chemical Dictionary, 5th ed). carbonates : Organooxygen compounds that are salts or esters of carbonic acid, H2CO3.	2.06	1	0	carbon oxoanion
2-amino-1,3,4-thiadiazole 2-amino-1,3,4-thiadiazole: structure; RN given refers to parent cpd	2.03	1	0
2-Butyl-1H-benzimidazole [no description available]	1.96	1	0	benzimidazoles
nsc 520594 [no description available]	2.01	1	0
tiadenol tiadenol: structure	1.97	1	0	aliphatic sulfide
iridium Iridium: A metallic element with the atomic symbol Ir, atomic number 77, and atomic weight 192.22.	3.37	6	0	cobalt group element atom; platinum group metal atom
manganese Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.	2.07	1	0	elemental manganese; manganese group element atom	Escherichia coli metabolite; micronutrient
mercury Mercury: A silver metallic element that exists as a liquid at room temperature. It has the atomic symbol Hg (from hydrargyrum, liquid silver), atomic number 80, and atomic weight 200.59. Mercury is used in many industrial applications and its salts have been employed therapeutically as purgatives, antisyphilitics, disinfectants, and astringents. It can be absorbed through the skin and mucous membranes which leads to MERCURY POISONING. Because of its toxicity, the clinical use of mercury and mercurials is diminishing.. mercury(0) : Elemental mercury of oxidation state zero.	7.49	2	0	elemental mercury; zinc group element atom	neurotoxin
neodymium Neodymium: An element of the rare earth family of metals. It has the atomic symbol Nd, atomic number 60, and atomic weight 144.24, and is used in industrial applications.	2.07	1	0	f-block element atom; lanthanoid atom
palladium Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.	8.19	5	0	metal allergen; nickel group element atom; platinum group metal atom
platinum Platinum: A heavy, soft, whitish metal, resembling tin, with atomic number 78, atomic weight 195.084, symbol Pt. It is used in manufacturing equipment for laboratory and industrial use. It occurs as a black powder (platinum black) and as a spongy substance (spongy platinum) and may have been known in Pliny's time as alutiae.	2.8	3	0	elemental platinum; nickel group element atom; platinum group metal atom
rhenium Rhenium: A metal, atomic number 75, atomic weight 186.207, symbol Re.	2.43	2	0	manganese group element atom
rhodium Rhodium: A hard and rare metal of the platinum group, atomic number 45, atomic weight 102.905, symbol Rh.. rhodium atom : A cobalt group element atom of atomic number 45.	3.01	4	0	cobalt group element atom
ruthenium Ruthenium: A hard, brittle, grayish-white rare earth metal with an atomic symbol Ru, atomic number 44, and atomic weight 101.07. It is used as a catalyst and hardener for PLATINUM and PALLADIUM.	4.2	15	0	iron group element atom; platinum group metal atom
silver Silver: An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.	7.8	3	0	copper group element atom; elemental silver	Escherichia coli metabolite
terbium Terbium: An element of the rare earth family of metals. It has the atomic symbol Tb, atomic number 65, and atomic weight 158.92.	2.1	1	0	f-block element atom; lanthanoid atom
cadmium Cadmium: An element with atomic symbol Cd, atomic number 48, and atomic weight 112.41. It is a metal and ingestion will lead to CADMIUM POISONING.. elemental cadmium : An element in the zinc group of the periodic table with atomic number 48, atomic mass 112, M.P. 321degreeC, and B.P. 765degreeC). An odourless, tasteless, and highly poisonous soft, ductile, lustrous metal with electropositive properties. It has eight stable isotopes: (106)Cd, (108)Cd,(110)Cd, (111)Cd, (112)Cd, (113)Cd, (114)Cd and (116)Cd, with (112)Cd and (114)Cd being the most common.	2.1	1	0	cadmium molecular entity; zinc group element atom
chromium Chromium: A trace element that plays a role in glucose metabolism. It has the atomic symbol Cr, atomic number 24, and atomic weight 52. According to the Fourth Annual Report on Carcinogens (NTP85-002,1985), chromium and some of its compounds have been listed as known carcinogens.. chromium ion : An chromium atom having a net electric charge.. chromium atom : A chromium group element atom that has atomic number 24.	2.17	1	0	chromium group element atom; metal allergen	micronutrient
europium Europium: An element of the rare earth family of metals. It has the atomic symbol Eu, atomic number 63, and atomic weight 152. Europium is used in the form of its salts as coatings for cathode ray tubes and in the form of its organic derivatives as shift reagents in NMR spectroscopy.	7.5	2	0	f-block element atom; lanthanoid atom
gadolinium Gadolinium: An element of the rare earth family of metals. It has the atomic symbol Gd, atomic number 64, and atomic weight 157.25. Its oxide is used in the control rods of some nuclear reactors.	2.1	1	0	f-block element atom; lanthanoid atom
gold Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.	8.35	6	0	copper group element atom; elemental gold
vanadium Vanadium: A metallic element with the atomic symbol V, atomic number 23, and atomic weight 50.94. It is used in the manufacture of vanadium steel. Prolonged exposure can lead to chronic intoxication caused by absorption usually via the lungs.	2.73	3	0	elemental vanadium; vanadium group element atom	micronutrient
ytterbium Ytterbium: An element of the rare earth family of metals. It has the atomic symbol Yb, atomic number 70, and atomic weight 173. Ytterbium has been used in lasers and as a portable x-ray source.	2.1	1	0	f-block element atom; lanthanoid atom
zirconium Zirconium: A rather rare metallic element with atomic number 40, atomic weight 91.224, and symbol Zr.	2.31	1	0	titanium group element atom
mercuric chloride Mercuric Chloride: Mercury chloride (HgCl2). A highly toxic compound that volatizes slightly at ordinary temperature and appreciably at 100 degrees C. It is corrosive to mucous membranes and used as a topical antiseptic and disinfectant.. mercury dichloride : A mercury coordination entity made up of linear triatomic molecules in which a mercury atom is bonded to two chlorines. Water-soluble, it is highly toxic. Once used in a wide variety of applications, including preserving wood and anatomical specimens, embalming and disinfecting, as an intensifier in photography, as a mordant for rabbit and beaver furs, and freeing gold from lead, its use has markedly declined as less toxic alternatives have been developed.	2.08	1	0	mercury coordination entity	sensitiser
hypochlorous acid Hypochlorous Acid: An oxyacid of chlorine (HClO) containing monovalent chlorine that acts as an oxidizing or reducing agent.. hypochlorous acid : A chlorine oxoacid with formula HOCl; a weak, unstable acid, it is the active form of chlorine in water.	2.17	1	0	chlorine oxoacid; reactive oxygen species	EC 2.5.1.18 (glutathione transferase) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; human metabolite
bromine Bromine: A halogen with the atomic symbol Br, atomic number 35, and atomic weight 79.904. It is a volatile reddish-brown liquid that gives off suffocating vapors, is corrosive to the skin, and may cause severe gastroenteritis if ingested.	2.42	2	0	diatomic bromine
ferrous chloride ferrous chloride: induces convulsions; RN given refers to parent cpd	2.15	1	0	iron coordination entity
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	2.42	2	0	dihydrogen
fluorine Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.	8.71	2	0	diatomic fluorine; gas molecular entity	NMR chemical shift reference compound
galactose aldohexose : A hexose with a (potential) aldehyde group at one end.	1.92	1	0
ozone Ozone: The unstable triatomic form of oxygen, O3. It is a powerful oxidant that is produced for various chemical and industrial uses. Its production is also catalyzed in the ATMOSPHERE by ULTRAVIOLET RAY irradiation of oxygen or other ozone precursors such as VOLATILE ORGANIC COMPOUNDS and NITROGEN OXIDES. About 90% of the ozone in the atmosphere exists in the stratosphere (STRATOSPHERIC OZONE).. ozone : An elemental molecule with formula O3. An explosive, pale blue gas (b.p. -112degreeC) that has a characteristic, pungent odour, it is continuously produced in the upper atmosphere by the action of solar ultraviolet radiation on atmospheric oxygen. It is an antimicrobial agent used in the production of bottled water, as well as in the treatment of meat, poultry and other foodstuffs.	7.02	1	0	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
cadmium nitrate cadmium nitrate: RN given refers to parent cpd. cadmium nitrate : An inorganic nitrate salt having Cd(2+) as the counterion.	2.03	1	0	cadmium salt; inorganic nitrate salt	carcinogenic agent; genotoxin; hepatotoxic agent
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.	4.96	11	0	benzimidazole fungicide; benzimidazoles; benzimidazolylcarbamate fungicide; carbamate ester	antifungal agrochemical; antinematodal drug; metabolite; microtubule-destabilising agent
tiletamine hydrochloride Cyclohexanones: Cyclohexane ring substituted by one or more ketones in any position.. cyclohexanones : Any alicyclic ketone based on a cyclohexane skeleton and its substituted derivatives thereof.	2.21	1	0
parbendazole parbendazole: anthelmintic used against a variety of gastrointestinal parasites; minor descriptor (75-86); on-line & INDEX MEDICUS search BENZIMIDAZOLES; RN given refers to parent cpd	6.97	1	0	benzimidazoles; carbamate ester
selegiline Selegiline: A selective, irreversible inhibitor of Type B monoamine oxidase that is used for the treatment of newly diagnosed patients with PARKINSON DISEASE, and for the treatment of depressive disorders. The compound without isomeric designation is Deprenyl.	2.25	1	0	selegiline; terminal acetylenic compound	geroprotector
levamisole Levamisole: An antihelminthic drug that has been tried experimentally in rheumatic disorders where it apparently restores the immune response by increasing macrophage chemotaxis and T-lymphocyte function. Paradoxically, this immune enhancement appears to be beneficial in rheumatoid arthritis where dermatitis, leukopenia, and thrombocytopenia, and nausea and vomiting have been reported as side effects. (From Smith and Reynard, Textbook of Pharmacology, 1991, p435-6). levamisole : A 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole that has S configuration. It is used (generally as the monohydrochloride salt) to treat parasitic worm infections in pigs, sheep and cattle and was formerly used in humans as an adjuvant to chemotherapy for the treatment of various cancers. It is also widely used as an adulterant to coccaine.	7.58	24	2	6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole	antinematodal drug; antirheumatic drug; EC 3.1.3.1 (alkaline phosphatase) inhibitor; immunological adjuvant; immunomodulator
fluorides [no description available]	2.77	3	0	halide anion; monoatomic fluorine
benomyl [no description available]	1.97	1	0	aromatic amide; benzimidazole fungicide; benzimidazoles; benzimidazolylcarbamate fungicide; carbamate ester	acaricide; anthelminthic drug; antifungal agrochemical; microtubule-destabilising agent; tubulin modulator
1-(trimethylsilyl)-1h-imidazole N-trimethylsilylimidazole : A member of the class of imidazoles in which the hydrogen at position 1 is replaced by a trimethylsilyl group. N-trimethylsilylimidazole is a derivatisation agent used in gas chromatography/mass spectrometry applications.	2.01	1	0	imidazoles; N-silyl compound	chromatographic reagent
tert-butyldimethylsilyl chloride tert-butyldimethylsilyl chloride: structure in first source. tert-butyldimethylsilyl chloride : A silyl chloride consisting of a central silicon atom covalently bound to one chloro, one tert-butyl and two methyl groups. tert-Butyldimethylsilyl chloride is a derivatisation agent used in gas chromatography/mass spectrometry applications.	2.05	1	0	silyl chloride	chromatographic reagent
iodine [no description available]	2.03	1	0	halide anion; monoatomic iodine	human metabolite
2,6-diaminopurine 9H-purine-2,6-diamine : A member of the class of 2,6-diaminopurines that is 9H-purine in which the hydrogens at positions 2 and 6 are replaced by amino groups.	1.93	1	0	2,6-diaminopurines; primary amino compound	antineoplastic agent
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.	2.05	1	0	benzenes; phenyl acetates
pyrrolidine [no description available]	9.22	8	7	azacycloalkane; pyrrolidines; saturated organic heteromonocyclic parent
1,4-dioxane 1,4-dioxane: dehydrating agent; polar solvent miscible both with water & most organic solvents. dioxane : Any member of the class of dioxanes that is a cyclohexane in which two carbon atoms are replaced by oxygen atoms.. 1,4-dioxane : A dioxane with oxygen atoms at positions 1 and 4.	2.11	1	0	dioxane; volatile organic compound	carcinogenic agent; metabolite; NMR chemical shift reference compound; non-polar solvent
tetrachloroethylene Tetrachloroethylene: A chlorinated hydrocarbon used as an industrial solvent and cooling liquid in electrical transformers. It is a potential carcinogen.	1.94	1	0	chlorocarbon; chloroethenes	nephrotoxic agent
dimethylacetamide hallucinogen : Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations and other alterations of mood and thinking.. N,N-dimethylacetamide : A member of the class of acetamides that is acetamide in which the hydrogens attached to the N atom have been replaced by two methyl groups respectively. Metabolite observed in cancer metabolism.	2.47	2	0	acetamides; monocarboxylic acid amide	human metabolite
pyrene pyrene: structure in Merck Index, 9th ed, #7746. pyrene : An ortho- and peri-fused polycyclic arene consisting of four fused benzene rings, resulting in a flat aromatic system.	2.11	1	0	ortho- and peri-fused polycyclic arene	fluorescent probe; persistent organic pollutant
rafoxanide Rafoxanide: Veterinary anthelmintic for grazing animals; used to treat fluke, hookworm and other infestations.	1.97	1	0
2-tert-butylbenzimidazole 2-tert-butylbenzimidazole: structure in first source	1.96	1	0
alkenes [no description available]	2.47	2	0
amoxicillin Amoxicillin: A broad-spectrum semisynthetic antibiotic similar to AMPICILLIN except that its resistance to gastric acid permits higher serum levels with oral administration.. amoxicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-(4-hydroxyphenyl)acetamido group.	2.07	1	0	penicillin allergen; penicillin	antibacterial drug
ensulizole ensulizole: sunscreening agent; structure in first source	2.02	1	0	benzimidazoles
zidovudine Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.	2.05	1	0	azide; pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
flubendazole flubendazole: the p-fluoro analog of mebendazole. flubendazole : A member of the class of mebendazole in which the benzoyl group is replaced by a p-fluorobenzoyl group. A broad-spectrum anthelmintic, it is used, particularly in veterinary medicine, for the treatment of nematodal infections.	2.08	1	0	aromatic ketone; benzimidazoles; carbamate ester; organofluorine compound	antinematodal drug; teratogenic agent
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	2.78	3	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
iprodione iprodione : An imidazolidine-2,4-dione in which the nitrogen at position 1 is substituted by an N-(isopropyl)carboxamide group while that at position 3 is substituted by a 3,5-dichlorophenyl group. A contact fungicide, it blocks the growth of the fungal mycelium and inhibits the germination of fungal spores. It is used on fruit and vegetable crops affected by various fungal diseases. It is also used as a nematicide.	2.46	2	0	benzenes; dichlorophenyl dicarboximide fungicide; imidazole fungicide; imidazolidine-2,4-dione; ureas	antifungal agrochemical; nematicide
ribavirin Rebetron: Rebetron is tradename	9.13	7	7	1-ribosyltriazole; aromatic amide; monocarboxylic acid amide; primary carboxamide	anticoronaviral agent; antiinfective agent; antimetabolite; antiviral agent; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
chlorodiphenyl (54% chlorine) Chlorodiphenyl (54% Chlorine): A mixture of polychlorinated biphenyls that induces hepatic microsomal UDP-glucuronyl transferase activity towards thyroxine.. Aroclor 1254 : A mixture of polychlorobiphenyls of unspecified composition, containing 54% chlorine (X = Cl or H).	1.97	1	0
oxfendazole [no description available]	6.35	8	2	benzimidazoles; carbamate ester; sulfoxide	antinematodal drug
nitazoxanide nitazoxanide: a 5-nitrothiazolyl derivative used for a broad range of intestinal parasitic infections including CRYPTOSPORIDIUM and GIARDIA; it is a redox-active nitrothiazolyl-salicylamide prodrug	4.24	2	0	benzamides; carboxylic ester
indacrinone indacrinone: polyvalent saluretic; RN given refers to parent cpd without isomeric designation; structure	2.05	1	0
closantel closantel: structure. N-{5-chloro-4-[(4-chlorophenyl)(cyano)methyl]-2-methylphenyl}-2-hydroxy-3,5-diiodobenzamide : An aromatic amide resulting from the formal condensation of the carboxy group of 3,5-diiodosalicylic acid with the amino group of aniline substituted at positions 2, 4, and 5 by methyl, (4-chlorophenyl)(cyano)methyl, and methyl groups respectively.. closantel : A racemate comprising equimolar amounts of (R)- and (S)-clostanel. An anthelmintic, it is used (as the dihydrate of the sodium salt) in veterinary medicine for the treatment of fluke and nematode infections.	4.28	4	1	aromatic amide; monocarboxylic acid amide; monochlorobenzenes; nitrile; organoiodine compound; phenols
azaconazole azaconazole: structure given in first source. azaconazole : A member of the class of dioxolanes that is 1,3-dioxolane substituted at position 2 by 2,4-dichlorophenyl and 1,2,4-triazol-1-ylmethyl groups. A fungicide used mainly in ornamental crops to control canker and other diseases. Azaconazole is moderately toxic to mammals but is not expected to bioaccumulate. It is moderately toxic to birds, fish and aquatic invertebrates.	2.03	1	0	conazole fungicide; cyclic ketal; dichlorobenzene; dioxolane; triazole fungicide; triazoles	antifungal agrochemical; EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor
propiconazole Orbit: Bony cavity that holds the eyeball and its associated tissues and appendages.	2.04	1	0	conazole fungicide; cyclic ketal; dichlorobenzene; triazole fungicide; triazoles	antifungal agrochemical; EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor; environmental contaminant; xenobiotic
dazoxiben dazoxiben: RN given refers to parent cpd	2.01	1	0
lovastatin Lovastatin: A fungal metabolite isolated from cultures of Aspergillus terreus. The compound is a potent anticholesteremic agent. It inhibits 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It also stimulates the production of low-density lipoprotein receptors in the liver.. lovastatin : A fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as Aspergillus terreus and Pleurotus ostreatus (oyster mushroom).	2.03	1	0	delta-lactone; fatty acid ester; hexahydronaphthalenes; polyketide; statin (naturally occurring)	anticholesteremic drug; antineoplastic agent; Aspergillus metabolite; prodrug
imiquimod Imiquimod: A topically-applied aminoquinoline immune modulator that induces interferon production. It is used in the treatment of external genital and perianal warts, superficial CARCINOMA, BASAL CELL; and ACTINIC KERATOSIS.. imiquimod : An imidazoquinoline fused [4,5-c] carrying isobutyl and amino substituents at N-1 and C-4 respectively. A prescription medication, it acts as an immune response modifier and is used to treat genital warts, superficial basal cell carcinoma, and actinic keratosis.	2.31	1	0	imidazoquinoline	antineoplastic agent; interferon inducer
mibefradil Mibefradil: A benzimidazoyl-substituted tetraline that selectively binds and inhibits CALCIUM CHANNELS, T-TYPE.	2.1	1	0	tetralins	T-type calcium channel blocker
u 77779 bizelesin: structure given in first source	3.1	1	0
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	2.38	2	0	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
glycoluril glycoluril: a compound made of two 2-imidazolidinone fused at the 4 and 5 positions	2.07	1	0	azabicycloalkane; ureas
guanidine thiocyanate guanidine thiocyanate: a powerful chaotropic agent	2.11	1	0
phenylalanylphenylalanine phenylalanylphenylalanine: RN given refers to (L,L)-isomer	2.13	1	0
tris(2,2'-bipyridine)ruthenium(II) tris(2,2'-bipyridyl)ruthenium(II): a fluorescent dye; structure in first source	2.15	1	0	ruthenium coordination entity	fluorochrome
proadifen hydrochloride [no description available]	1.96	1	0
telmisartan Telmisartan: A biphenyl compound and benzimidazole derivative that acts as an angiotensin II type 1 receptor antagonist. It is used in the management of HYPERTENSION.. telmisartan : A member of the class of benzimidazoles used widely in the treatment of hypertension.	2.46	2	0	benzimidazoles; biphenyls; carboxybiphenyl	angiotensin receptor antagonist; antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; environmental contaminant; xenobiotic
valerophenone [no description available]	2.48	2	0	aromatic ketone	plant metabolite; volatile oil component
perylenediimide perylenediimide: structure in first source. perylenediimide : The 3,4,9,10-tetracarboxylic diimide derivative of perylene.	2.1	1	0	dicarboximide; organic heteropolycyclic compound	fluorochrome
naphthalimides Naphthalimides: Compounds with three fused rings that appear like a naphthalene fused to piperidone or like a benz(de)isoquinoline-1,3-dione (not to be confused with BENZYLISOQUINOLINES which have a methyl separating the naphthyl from the benzyl rings). Members are CYTOTOXINS.	2.21	1	0
1,7-phenanthroline [no description available]	2.01	1	0	phenanthroline
1h-imidazo(4,5-b)pyridine 1H-imidazo(4,5-b)pyridine: structure given in first source. 4-azabenzimidazole : The [4,5-b]-fused isomer of imidazopyridine.	1.98	1	0	imidazopyridine
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	4.77	29	0	1,2,3-triazole
1h-tetrazole tetrazole : An azaarene that is a five-membered ring composed of 4 nitrogen and 1 carbon atom.. 2H-tetrazole : A tetrazole tautomer where the proton is located on the 2 position.	2.13	1	0	one-carbon compound; tetrazole
difluorotoluene difluorotoluene: structure in first source	2	1	0
4-fluoro-3-nitrobenzoic acid [no description available]	2.08	1	0
fluorodeoxyglucose f18 Fluorodeoxyglucose F18: The compound is given by intravenous injection to do POSITRON-EMISSION TOMOGRAPHY for the assessment of cerebral and myocardial glucose metabolism in various physiological or pathological states including stroke and myocardial ischemia. It is also employed for the detection of malignant tumors including those of the brain, liver, and thyroid gland. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1162)	3.82	2	1	2-deoxy-2-((18)F)fluoro-D-glucose; 2-deoxy-2-fluoro-aldehydo-D-glucose
3-methylhistamine 3-methylhistamine: RN given refers to parent cpd	2.01	1	0
4(5)-phenylimidazole 4(5)-phenylimidazole: tautomeric cpd; cytochrome P450 14alpha-sterol demethylase, CYP51 antagonist	1.96	1	0
n-acetylhistamine N-acetylhistamine : A member of the class of acetamides that is acetamide comprising histamine having an acetyl group attached to the side-chain amino function.	2.01	1	0	acetamides; imidazoles	human metabolite
n-acetyltryptamine N-acetyltryptamine: antagonizes the melatonin-induced inhibition of dopamine release from retina; RN given refers to parent cpd. N-acetyltryptamine : A tryptamine compound having an acetyl substituent attached to the side-chain amino function.	2.07	1	0	acetamides; indoles
2-(2'-pyridyl)benzimidazole 2-(2'-pyridyl)benzimidazole: structure in first source	1.96	1	0
7-methyladenine 7-methyladenine: potential marker for monitoring exposure to methylatingcarcinogens. 7-methyladenine : Adenine substituted with a methyl group at position N-7.	2.07	1	0	methyladenine	metabolite
secnidazole [no description available]	3.35	1	0	C-nitro compound; imidazoles; secondary alcohol	epitope
methanesulfonamide [no description available]	2.15	1	0
1h-benzotriazole-5-carboxylic acid 1H-benzotriazole-5-carboxylic acid: structure given in first source	2.07	1	0
xanthosine 5'-triphosphate xanthosine 5'-phosphate : xanthosine phosphate compounds having phosphate groups at position 5'.. 5'-xanthylic acid : A purine ribonucleoside 5'-monophosphate having xanthine as the nucleobase.	2.07	1	0	purine ribonucleoside 5'-monophosphate; xanthosine 5'-phosphate	Escherichia coli metabolite; metabolite; mouse metabolite
carbohydrazide carbohydrazide: structure. carbohydrazide : A hydrazide consisting of hydrazine carrying one or more carboacyl groups.. carbonyl dihydrazine : A carbohydrazide obtained by formal condensation between hydrazinecarboxylic acid and hydrazine.	2.49	2	0	carbohydrazide; one-carbon compound
oxazolidin-2-one Oxazolidinones: Derivatives of oxazolidin-2-one. They represent an important class of synthetic antibiotic agents.. oxazolidin-2-one : An oxazolidinone that is 1,3-oxazolidine with an oxo substituent at position 2.. oxazolidinone : An oxazolidine containing one or more oxo groups.	2.02	1	0	carbamate ester; oxazolidinone	metabolite
2-amino-1-methylbenzimidazole 2-amino-1-methylbenzimidazole: structure in first source	2.08	1	0	benzimidazoles
benzylvanillin benzylvanillin: structure given in first source	7.08	1	0
1-benzylimidazole 1-benzylimidazole: inhibits human thromboxane synthetase	2.02	1	0
1-(3-aminopropyl)imidazole [no description available]	2.01	1	0	imidazoles
imidazo(1,2-a)pyridine imidazo(1,2-a)pyridine: structure	3.84	3	0
albendazole sulfoxide albendazole sulfoxide: RN given refers to parent cpd; structure given in first source	2.94	4	0	sulfoxide
clarithromycin Clarithromycin: A semisynthetic macrolide antibiotic derived from ERYTHROMYCIN that is active against a variety of microorganisms. It can inhibit PROTEIN SYNTHESIS in BACTERIA by reversibly binding to the 50S ribosomal subunits. This inhibits the translocation of aminoacyl transfer-RNA and prevents peptide chain elongation.. clarithromycin : The 6-O-methyl ether of erythromycin A, clarithromycin is a macrolide antibiotic used in the treatment of respiratory-tract, skin and soft-tissue infections. It is also used to eradicate Helicobacter pylori in the treatment of peptic ulcer disease. It prevents bacteria from growing by interfering with their protein synthesis.	2.44	2	0	macrolide antibiotic	antibacterial drug; environmental contaminant; protein synthesis inhibitor; xenobiotic
4-aminoquinazoline 4-aminoquinazoline: structure in first source	2.06	1	0
tebuconazole Lynx: A genus in the family FELIDAE comprising felines with long legs, ear tufts, and a short tail.. 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol : A tertiary alcohol that is pentan-3-ol substituted by a 4-chlorophenyl, methyl, methyl, and a 1H-1,2,4-triazol-1-ylmethyl at positions 1, 4, 4 and 3 respectively.. tebuconazole : A racemate composed of equimolar amounts of (R)- and (S)-tebuconazole. A fungicide effective against various smut and bunt diseases in cereals and other field crops.	2.08	1	0	monochlorobenzenes; tertiary alcohol; triazoles
cyprodinil cyprodinil: structure in first source. cyprodinil : A member of the class of aminopyrimidine that is N-phenylpyrimidin-2-amine carrying additional cyclopropyl and methyl substituents at positions 4 and 6 respectively. A broad spectrum fungicide used to control a range of pathogens including Tapesia yallundae, Botrytis spp., Alternaria spp. and Rhynchospium secalis. Whilst it is a recognised irritant no serious human health concerns have been identified. It is moderately toxic to birds as well as most aquatic organisms and earthworms, but it is not considered toxic to honeybees.	2.08	1	0	aminopyrimidine; anilinopyrimidine fungicide; cyclopropanes; secondary amino compound	antifungal agrochemical; aryl hydrocarbon receptor agonist; environmental contaminant; xenobiotic
fludioxonil fludioxonil: structure in first source. fludioxonil : A member of the class of benzodioxoles that is 2,2-difluoro-1,3-benzodioxole substituted at position 4 by a 3-cyanopyrrol-4-yl group. A fungicide seed treatment for control of a range of diseases including Fusarium, Rhizoctonia and Alternaria.	2.08	1	0	benzodioxoles; nitrile; organofluorine compound; pyrroles	androgen antagonist; antifungal agrochemical; estrogen receptor agonist
5-bromonicotinic acid 5-bromonicotinic acid: structure given in first source	2.17	1	0
diethofencarb diethofencarb: structure given in first source. diethofencarb : A carbamate ester that is the isopropyl ester of (3,4-diethoxyphenyl)carbamic acid. A fungicide with strong activity against Botrytis cinerea and benzimidazole-resistant strains of Botryis spp.	2.46	2	0	aromatic ether; carbamate ester; carbanilate fungicide	antifungal agrochemical
norcantharidin norcantharidin: structure given in first source; RN given refers to cpds without isomeric designation	7.11	1	0	furofuran
glucuronic acid Glucuronic Acid: A sugar acid formed by the oxidation of the C-6 carbon of GLUCOSE. In addition to being a key intermediate metabolite of the uronic acid pathway, glucuronic acid also plays a role in the detoxification of certain drugs and toxins by conjugating with them to form GLUCURONIDES.. D-glucuronic acid : The D-enantiomer of glucuronic acid.. D-glucopyranuronic acid : A D-glucuronic acid in cyclic pyranose form.	2.47	2	0	D-glucuronic acid	algal metabolite
phosphoramide mustard [no description available]	1.97	1	0	nitrogen mustard; phosphorodiamide
benzothiazoline [no description available]	2.11	1	0
hydroxybenzindazole hydroxybenzindazole: structure	2.02	1	0
5-formyl-2'-deoxyuridine 5-formyl-2'-deoxyuridine: structure given in first source	2.07	1	0
diosgenin [no description available]	2.21	1	0	3beta-sterol; hexacyclic triterpenoid; sapogenin; spiroketal	antineoplastic agent; antiviral agent; apoptosis inducer; metabolite
cobalt Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.	2.47	2	0	cobalt group element atom; metal allergen	micronutrient
1,4,7-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane 1,4,7-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane: structure in first source	2.1	1	0
tryptoline tryptoline: neurotoxic factor that may be involved in development of Parkinson's disease; enzymatic prep from human brain converts tryptamine to tryptoline; RN given refers to parent cpd; structure	2.13	1	0	beta-carbolines
phosphites Phosphites: Inorganic salts or organic esters of phosphorous acid that contain the (3-)PO3 radical. (From Grant & Hackh's Chemical Dictionary, 5th ed). phosphite(3-) : A trivalent inorganic anion obtained by removal of all three protons from phosphorous acid.	2.06	1	0	phosphite ion; trivalent inorganic anion
5-hydroxythiabendazole 5-hydroxythiabendazole: thiabendazole metabolite	2	1	0	benzimidazoles
thromboxanes thromboxane : A class of oxygenated oxane derivatives, originally derived from prostaglandin precursors in platelets, that stimulate aggregation of platelets and constriction of blood vessels.	1.96	1	0
ici 198615 ICI 198615: an LTD4 receptor antagonist; SRS-A antagonist; structure given in first source	1.97	1	0
n,n-dipropyl-2-(4-methoxy-3-(2-phenylethoxy)phenyl)ethylamine monohydrochloride N,N-dipropyl-2-(4-methoxy-3-(2-phenylethoxy)phenyl)ethylamine monohydrochloride: structure given in first source; a sigma receptor ligand	2.31	1	0
lexitropsin lexitropsin: structure given in first source; information reading oligopeptide	3.1	1	0
perimidine [no description available]	7.17	1	0	perimidine
celastrol [no description available]	2.31	1	0	monocarboxylic acid; pentacyclic triterpenoid	anti-inflammatory drug; antineoplastic agent; antioxidant; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; Hsp90 inhibitor; metabolite
imidodiphosphonic acid imidodiphosphonic acid: in combination with technetrium, a superior radiopharmaceutical for myocardial infarct imaging; RN given refers to parent cpd	2.25	1	0
carbene carbene: electrically neutral species H2C: and its derivatives, in which the carbon is covalently bonded to two univalent groups of any kind or a divalent group and bears two nonbonding electrons; carbene is the name of the parent hydride :CH2 ; hence, the name dichlorocarbene for :CCl2. However, names for acyclic and cyclic hydrocarbons containing one or more divalent carbon atoms are derived from the name of the corresponding all-4-hydrocarbon using the suffix -ylidene; methylene carbene also available. carbene : The electrically neutral species H2C(2.) and its derivatives, in which the carbon is covalently bonded to two univalent groups of any kind or a divalent group and bears two nonbonding electrons, which may be spin-paired (singlet state) or spin-non-paired (triplet state).	3.01	4	0	carbene; methanediyl
glycyl-arginyl-glycyl-aspartyl-serine glycyl-arginyl-glycyl-aspartyl-serine: synthetic peptide from fibronectins; inhibits experimental metastasis of murine melanoma cells	2.31	1	0
dehydroalanine 2-ammonioprop-2-enoate : An amino acid zwitterion resulting from a transfer of a proton from the carboxy group to the amino group of 2-aminoacrylic acid.. 2-aminoacrylic acid : A 2,3-dehydroamino acid that is alanine which has been dehydrogenated to introduce a double bond between positions 2 and 3.	2.02	1	0	2,3-dehydroamino acid; alpha,beta-unsaturated monocarboxylic acid; amino acid zwitterion; enamine; non-proteinogenic alpha-amino acid	alkylating agent; human metabolite; mouse metabolite
2',6'-dimethyltyrosine 2',6'-dimethyltyrosine: structure given in first source	2	1	0
furamidine furamidine: RN given refers to parent cpd; WR 199385 refers to di-HCl; pafuramidine is a prodrug of this	2.06	1	0
bis-benzimidazole bis-benzimidazole: in vitro inhibitor of arenavirus synthesis; studied in treatment of lymphocytic choriomeningitis virus infections; also used as its di-HCl salt, A37536; RN given refers to parent cpd with unspecified isomeric designation; structure	7.07	1	0
safinamide safinamide: short-acting inhibitor of MOA-B; FCE 26743 is (S)-isomer, FCE 28073 is (R)-isomer; structure in first source	2.25	1	0	amino acid amide
proline Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.	10.42	12	11	amino acid zwitterion; glutamine family amino acid; L-alpha-amino acid; proline; proteinogenic amino acid	algal metabolite; compatible osmolytes; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
lonafarnib lonafarnib: inhibitor of farnesyl protein transferase. lonafarnib : A 4-{2-[4-(3,10-dibromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl)piperidin-1-yl]-2-oxoethyl}piperidine-1-carboxamide that has R configuration. It is used as oral farnesyltransferase inhibitor.	3.41	1	0	4-{2-[4-(3,10-dibromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl)piperidin-1-yl]-2-oxoethyl}piperidine-1-carboxamide	antineoplastic agent; EC 2.5.1.58 (protein farnesyltransferase) inhibitor
moxifloxacin Moxifloxacin: A fluoroquinolone that acts as an inhibitor of DNA TOPOISOMERASE II and is used as a broad-spectrum antibacterial agent.. moxifloxacin : A quinolone that consists of 4-oxo-1,4-dihydroquinoline-3-carboxylic acid bearing a cyclopropyl substituent at position 1, a fluoro substitiuent at position 6, a (4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl group at position 7 and a methoxy substituent at position 8. A member of the fluoroquinolone class of antibacterial agents.	2.11	1	0	aromatic ether; cyclopropanes; fluoroquinolone antibiotic; pyrrolidinopiperidine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antibacterial drug
schizandrin a schizandrin A: the major lignan, 2-9%, of Schisandra plant; has hepatoprotective, antioxidant, and antineoplastic activities	3.27	1	0
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	3.14	5	0	oxygen hydride; oxygen radical; reactive oxygen species
tipifarnib [no description available]	3.41	1	0	imidazoles; monochlorobenzenes; primary amino compound; quinolone	antineoplastic agent; apoptosis inducer; EC 2.5.1.58 (protein farnesyltransferase) inhibitor
histidinol L-histidinol : An amino alcohol that is propanol substituted by 1H-imidazol-4-yl group at position 3 and an amino group at position 2 (the 2S stereoisomer).	2.01	1	0	amino alcohol; imidazoles	EC 2.3.1.97 (glycylpeptide N-tetradecanoyltransferase) inhibitor; Escherichia coli metabolite; human metabolite; Saccharomyces cerevisiae metabolite
paromomycin Paromomycin: An aminoglycoside antibacterial and antiprotozoal agent produced by species of STREPTOMYCES.. paromomycin : An amino cyclitol glycoside that is the 1-O-(2-amino-2-deoxy-alpha-D-glucopyranoside) and the 3-O-(2,6-diamino-2,6-dideoxy-beta-L-idopyranosyl)-beta-D-ribofuranoside of 4,6-diamino-2,3-dihydroxycyclohexane (the 1R,2R,3S,4R,6S diastereoisomer). It is obtained from various Streptomyces species. A broad-spectrum antibiotic, it is used (generally as the sulfate salt) for the treatment of acute and chronic intestinal protozoal infections, but is not effective for extraintestinal protozoal infections. It is also used as a therapeutic against visceral leishmaniasis.	3.31	1	0	amino cyclitol glycoside; aminoglycoside antibiotic	anthelminthic drug; antibacterial drug; antiparasitic agent; antiprotozoal drug
angiotensin ii Giapreza: injectable form of angiotensin II used to increase blood pressure in adult patients with septic or other distributive shock. Ile(5)-angiotensin II : An angiotensin II that acts on the central nervous system (PDB entry: 1N9V).	7.5	2	0	amino acid zwitterion; angiotensin II	human metabolite
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	2.05	1	0	divalent inorganic anion; phosphite ion
nickel monoxide [no description available]	2.13	1	0
1,4,7-triazacyclononane 1,4,7-triazacyclononane: structure given in first source	7.02	1	0	azacycloalkane; crown amine; saturated organic heteromonocyclic parent
bd 1047 N-(2-(3,4-Dichlorphenyl)ethyl)-N,N',N'-trimethyl-1,2-ethandiamin: sigma receptor ligand; putative sigma receptor antagonist with antidystonic activity	2.31	1	0	primary amine
methyl-1alpha, 7alpha-dihydroxy-3-oxopregn-4-en-21-oate methyl-1alpha, 7alpha-dihydroxy-3-oxopregn-4-en-21-oate: structure; RN given refers to (1alpha,7alpha)-isomer	1.93	1	0
phenserine phenserine: a carbamate analog of physostigmine; a long-acting inhibitor of cholinesterase	2.08	1	0
maltotriose Porcelite: a light-cured composite resin. alpha-maltotriose : A maltotriose trisaccharide in which the glucose residue at the reducing end is in the pyranose ring form and has alpha configuration at the anomeric carbon atom..	2.13	1	0	maltotriose trisaccharide	human metabolite
3-(3-amino-1,2,4-oxadiazol-5-yl)-5-chloro-2,6-pyrazinediamine 3-(3-amino-1,2,4-oxadiazol-5-yl)-5-chloro-2,6-pyrazinediamine: amiloride prodrug; structure given in first source	1.96	1	0
troleandomycin Troleandomycin: A macrolide antibiotic that is similar to ERYTHROMYCIN.. troleandomycin : A semi-synthetic macrolide antibiotic obtained by acetylation of the three free hydroxy groups of oleandomycin. Troleandomycin is only found in individuals that have taken the drug.	1.98	1	0	acetate ester; epoxide; macrolide antibiotic; monosaccharide derivative; polyketide; semisynthetic derivative	EC 1.14.13.97 (taurochenodeoxycholate 6alpha-hydroxylase) inhibitor; xenobiotic
ilaprazole ilaprazole: structure in first source	3.18	1	0	benzimidazoles; sulfoxide
dabigatran Dabigatran: A THROMBIN inhibitor which acts by binding and blocking thrombogenic activity and the prevention of thrombus formation. It is used to reduce the risk of stroke and systemic EMBOLISM in patients with nonvalvular atrial fibrillation.. dabigatran : An aromatic amide obtained by formal condensation of the carboxy group of 2-{[(4-carbamimidoylphenyl)amino]methyl}-1-methyl-1H-benzimidazole-5-carboxylic acid with the secondary amoino group of N-pyridin-2-yl-beta-alanine. The active metabolite of the prodrug dabigatran etexilate, it acts as an anticoagulant which is used for the prevention of stroke and systemic embolism.	2.07	1	0	aromatic amide; benzimidazoles; beta-alanine derivative; carboxamidine; pyridines	anticoagulant; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; EC 3.4.21.5 (thrombin) inhibitor
sorafenib [no description available]	9.03	3	0	(trifluoromethyl)benzenes; aromatic ether; monochlorobenzenes; phenylureas; pyridinecarboxamide	angiogenesis inhibitor; anticoronaviral agent; antineoplastic agent; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; ferroptosis inducer; tyrosine kinase inhibitor
l 778,123 L-778,123 (free base) : A member of the class of imidazoles that is 1H-imidazole substituted by (4-cyanophenyl)methyl and [4-(3-chlorophenyl)-3-oxopiperazin-1-yl]methyl groups at positions 1 and 5, respectively. It is a dual inhibitor of FPTase and GGPTase-I.	3.41	1	0	imidazoles; monochlorobenzenes; nitrile; piperazinone; tertiary amino compound	antineoplastic agent; EC 2.5.1.58 (protein farnesyltransferase) inhibitor; EC 2.5.1.59 (protein geranylgeranyltransferase type I) inhibitor
santonin Santonin: Anthelmintic isolated from the dried unexpanded flower heads of Artemisia maritima and other species of Artemisia found principally in Russian and Chinese Turkestan and the Southern Ural region. (From Merck, 11th ed.)	1.94	1	0	botanical anti-fungal agent; santonin	plant metabolite
lanosterol [no description available]	2.03	1	0	14alpha-methyl steroid; 3beta-sterol; tetracyclic triterpenoid	bacterial metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	2.46	2	0
2-oxindole 2-oxindole: RN given refers to parent cpd; structure. indolin-2-one : An indolinone carrying an oxo group at position 2.	2.52	2	0	gamma-lactam; indolinone
5,6-dichlorobenzimidazole 5,6-dichlorobenzimidazole: inhibits transcript elongation	3.07	5	0
6-Methoxy-2-naphthoic acid [no description available]	2.07	1	0	naphthoic acid
carboplatin [no description available]	2.05	1	0
glycogen glycogen : A polydisperse, highly branched glucan composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage, joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some cumulative alpha(1->6) links also may occur. The branches in glycogen typically contain 8 to 12 glucose residues.	1.96	1	0
epiglucan epiglucan: a highly side-chain/branched alkali-insoluble cell wall glucan from fungus such as Epicoccum nigrum, Botrytis cinerea, ascomycetes & basidiomycetes; also isolated S-4001 from Lei Wan (polyporus mylitiae), HA-beta-glucan from mushroom Pleutotus ostreatus (Fr.) Quel., and translam from seaweed Laminaria cichorioides; with commercially important functional properties including emulsification and friction reduction.	2.05	1	0
strychnine Strychnine: An alkaloid found in the seeds of STRYCHNOS NUX-VOMICA. It is a competitive antagonist at glycine receptors and thus a convulsant. It has been used as an analeptic, in the treatment of nonketotic hyperglycinemia and sleep apnea, and as a rat poison.. strychnine : A monoterpenoid indole alkaloid that is strychnidine bearing a keto substituent at the 10-position.	1.97	1	0	monoterpenoid indole alkaloid; organic heteroheptacyclic compound	avicide; cholinergic antagonist; glycine receptor antagonist; neurotransmitter agent; rodenticide
griseofulvin Griseofulvin: An antifungal agent used in the treatment of TINEA infections.. griseofulvin : An oxaspiro compound produced by Penicillium griseofulvum. It is used by mouth as an antifungal drug for infections involving the scalp, hair, nails and skin that do not respond to topical treatment.	2.03	1	0	1-benzofurans; antibiotic antifungal drug; benzofuran antifungal drug; organochlorine compound; oxaspiro compound	antibacterial agent; Penicillium metabolite
terconazole terconazole: structure & RN for (cis)-isomer from first source. terconazole : A racemate consisting of equimolar amounts of (2R,4S)- and (2S,4R)-terconazole. It has broad-spectrum antifungal activitiy and is used for the treatment of vaginal yeast infections (Candida).. (2R,4S)-terconazole : A 1-(4-{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-isopropylpiperazine in which positions 2 and 4 of the 1,3-dioxolane moiety have R and S configuration, respectively.	2.03	1	0	1-(4-{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-isopropylpiperazine
linezolid [no description available]	2.02	1	0	acetamides; morpholines; organofluorine compound; oxazolidinone	antibacterial drug; protein synthesis inhibitor
lignans Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	3.27	1	0
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	3.76	9	0	cyclodextrin
indoleglycerol phosphate indoleglycerol phosphate: inducer of tryptophan synthase. (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate : The (1S,2R)-diastereomer of 1-C-(indol-3-yl)glycerol 3-phosphate.	2.02	1	0	1-C-(indol-3-yl)glycerol 3-phosphate
cp 320626 CP 320626: structure in first source	2.03	1	0
arachidonic acid icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.	2.03	1	0	icosa-5,8,11,14-tetraenoic acid; long-chain fatty acid; omega-6 fatty acid	Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite; mouse metabolite
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	4.14	2	0	resveratrol	antioxidant; phytoalexin; plant metabolite; quorum sensing inhibitor; radical scavenger
mycophenolic acid Mycophenolic Acid: Compound derived from Penicillium stoloniferum and related species. It blocks de novo biosynthesis of purine nucleotides by inhibition of the enzyme inosine monophosphate dehydrogenase (IMP DEHYDROGENASE). Mycophenolic acid exerts selective effects on the immune system in which it prevents the proliferation of T-CELLS, LYMPHOCYTES, and the formation of antibodies from B-CELLS. It may also inhibit recruitment of LEUKOCYTES to sites of INFLAMMATION.. mycophenolate : A monocarboxylic acid anion resulting from the removal of a proton from the carboxy group of mycophenolic acid.. mycophenolic acid : A member of the class of 2-benzofurans that is 2-benzofuran-1(3H)-one which is substituted at positions 4, 5, 6, and 7 by methyl, methoxy, (2E)-5-carboxy-3-methylpent-2-en-1-yl, and hydroxy groups, respectively. It is an antibiotic produced by Penicillium brevi-compactum, P. stoloniferum, P. echinulatum and related species. An immunosuppressant, it is widely used (partiularly as its sodium salt and as the 2-(morpholin-4-yl)ethyl ester prodrug, mycophenolate mofetil) to prevent tissue rejection following organ transplants and for the treatment of certain autoimmune diseases.	2.07	1	0	2-benzofurans; gamma-lactone; monocarboxylic acid; phenols	anticoronaviral agent; antimicrobial agent; antineoplastic agent; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; environmental contaminant; immunosuppressive agent; mycotoxin; Penicillium metabolite; xenobiotic
y 27632 Y 27632: RN given for di-HCl salt; inhibits Rho-associated protein kinase; inhibits calcium sensitization to affect smooth muscle relaxation; structure in first source. Y-27632 : A monocarboxylic acid amide that is trans-[(1R)-1-aminoethyl]cyclohexanecarboxamide in which one of the nitrogens of the aminocarbony group is substituted by a pyridine nucleus. It has been shown to exhibit inhibitory activity against Rho-associated protein kinase (ROCK) enzyme.	2.06	1	0	aromatic amide
bms 214662 7-cyano-2,3,4,5-tetrahydro-1-(1H-imidazol-4-ylmethyl)-3-(phenylmethyl)-4-(2-thienylsulfonyl)-1H-1,4-benzodiazepine: a farnesyltransferase inhibitor; structure in first source. BMS-214662 : A member of the class of benzodiazepines that is 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine substituted by (1H-imidazol-5-yl)methyl, benzyl, (thiophen-2-yl)sulfonyl, and cyano groups at positions 1, 3R, 4 and 7, respectively. It is a potent inhibitor of farnesyltransferase (IC50 = 1.35nM) which was under clinical development for the treatment of solid tumors.	3.41	1	0	benzenes; benzodiazepine; imidazoles; nitrile; sulfonamide; thiophenes	antineoplastic agent; apoptosis inducer; EC 2.5.1.58 (protein farnesyltransferase) inhibitor
epothilone a Epothilones: A group of 16-member MACROLIDES which stabilize MICROTUBULES in a manner similar to PACLITAXEL. They were originally found in the myxobacterium Sorangium cellulosum, now renamed to Polyangium (MYXOCOCCALES).	7.03	1	0	epothilone; epoxide	antineoplastic agent; metabolite; microtubule-stabilising agent; tubulin modulator
5-benzimidazolecarboxylic acid 5-benzimidazolecarboxylic acid: structure in first source	2.07	1	0
bms 433771 BMS 433771: a fusion inhibitor of respiratory syncytial virus; structure in first source	2.03	1	0
sodium bicarbonate Sodium Bicarbonate: A white, crystalline powder that is commonly used as a pH buffering agent, an electrolyte replenisher, systemic alkalizer and in topical cleansing solutions.	2.07	1	0	one-carbon compound; organic sodium salt	antacid; food anticaking agent
zn(ii)-phthalocyanine [no description available]	2.17	1	0	metallophthalocyanine; zinc tetrapyrrole	fluorochrome
calix(4)arene calix(4)arene: a cyclophane consisting of four phenolic units linked by methylene groups; structure in first source	2.48	2	0
pyrrolopyrimidine pyrrolopyrimidine: structure in first source	2.21	1	0
carbenoxolone sodium Carbenoxolone: An agent derived from licorice root. It is used for the treatment of digestive tract ulcers, especially in the stomach. Antidiuretic side effects are frequent, but otherwise the drug is low in toxicity.	2.37	2	0	triterpenoid
glycosides [no description available]	3.04	5	0
chalcone trans-chalcone : The trans-isomer of chalcone.	7.25	1	0	chalcone	EC 3.2.1.1 (alpha-amylase) inhibitor
piperine piperine : A N-acylpiperidine that is piperidine substituted by a (1E,3E)-1-(1,3-benzodioxol-5-yl)-5-oxopenta-1,3-dien-5-yl group at the nitrogen atom. It is an alkaloid isolated from the plant Piper nigrum.	2.25	1	0	benzodioxoles; N-acylpiperidine; piperidine alkaloid; tertiary carboxamide	food component; human blood serum metabolite; NF-kappaB inhibitor; plant metabolite
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	4.39	3	0	stilbene
pyrophosphate Diphosphates: Inorganic salts of phosphoric acid that contain two phosphate groups.	1.94	1	0	diphosphate ion
propylthiouracil Propylthiouracil: A thiourea antithyroid agent. Propythiouracil inhibits the synthesis of thyroxine and inhibits the peripheral conversion of throxine to tri-iodothyronine. It is used in the treatment of hyperthyroidism. (From Martindale, The Extra Pharmacopeoia, 30th ed, p534). 6-propyl-2-thiouracil : A pyrimidinethione consisting of uracil in which the 2-oxo group is substituted by a thio group and the hydrogen at position 6 is substituted by a propyl group.	6.92	1	0	pyrimidinethione	antidote to paracetamol poisoning; antimetabolite; antioxidant; antithyroid drug; carcinogenic agent; EC 1.14.13.39 (nitric oxide synthase) inhibitor; hormone antagonist
5,6-diphenyl-1,2,4-triazine-3-thiol 5,6-diphenyl-1,2,4-triazine-3-thiol: RN given refers to parent cpd; structure given in first source	2.02	1	0
2-mercaptobenzimidazole 2-mercaptobenzimidazole: purine synthesis antimetabolite; RN given refers to parent cpd	7.66	3	0
pyrantel Pyrantel: A depolarizing neuromuscular-blocking agent, that causes persistent nicotinic activation resulting in spastic paralysis of susceptible nematodes. It is a drug of second-choice after benzimidazoles for treatment of ascariasis, hookworm, and pinworm infections, being effective after a single dose. (From Smith and Reynard, Textbook of Pharmacology, 1992, p920). pyrantel : A carboxamidine that is 1,4,5,6-tetrahydropyrimidine that is substituted at position 1 by a methyl group and at position 2 by an (E)-2-(2-thienyl)vinyl group. It is used, particularly as the embonate [4,4'-methylenebis(3-hydroxy-2-naphthoate)] salt, as an anthelmintic that is effective against intestinal nematodes including threadworms, roundworms and hookworms, and is included in the WHO 'Model List of Essential Medicines'.	2.01	1	0	1,4,5,6-tetrahydropyrimidines; carboxamidine; thiophenes	antinematodal drug
curcumin Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.	7.1	1	0	aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger
1-benzyl-2-phenylbenzimidazole 1-benzyl-2-phenylbenzimidazole: has antineoplastic activity; structure in first source	2.11	1	0
thiouracil Thiouracil: Occurs in seeds of Brassica and Crucifera species. Thiouracil has been used as antithyroid, coronary vasodilator, and in congestive heart failure although its use has been largely supplanted by other drugs. It is known to cause blood dyscrasias and suspected of terato- and carcinogenesis.. thiouracil : A nucleobase analogue that is uracil in which the oxo group at C-2 is replaced by a thioxo group.	6.92	1	0	nucleobase analogue; thiocarbonyl compound	antithyroid drug; metabolite
methimazole Methimazole: A thioureylene antithyroid agent that inhibits the formation of thyroid hormones by interfering with the incorporation of iodine into tyrosyl residues of thyroglobulin. This is done by interfering with the oxidation of iodide ion and iodotyrosyl groups through inhibition of the peroxidase enzyme.. methimazole : A member of the class of imidazoles that it imidazole-2-thione in which a methyl group replaces the hydrogen which is attached to a nitrogen.	2.03	1	0	1,3-dihydroimidazole-2-thiones	antithyroid drug
capsaicin ALGRX-4975: an injectable capsaicin (TRPV1 receptor agonist) formulation for longlasting pain relief. capsaicinoid : A family of aromatic fatty amides produced as secondary metabolites by chilli peppers.	8.57	2	0	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
5-chloro-1h-benzimidazole-2-thiol 5-chloro-1H-benzimidazole-2-thiol: trypanocidal	2.42	2	0
thiourea Thiourea: A photographic fixative used also in the manufacture of resins. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance may reasonably be anticipated to be a carcinogen (Merck Index, 9th ed). Many of its derivatives are ANTITHYROID AGENTS and/or FREE RADICAL SCAVENGERS.. thiourea : The simplest member of the thiourea class, consisting of urea with the oxygen atom substituted by sulfur.	8.85	3	0	one-carbon compound; thioureas; ureas	antioxidant; chromophore
potassium oxonate potassium oxonate: used to induce hyperuricemia in mice	2.25	1	0	organic molecular entity
thioacetamide Thioacetamide: A crystalline compound used as a laboratory reagent in place of HYDROGEN SULFIDE. It is a potent hepatocarcinogen.. thioacetamide : A thiocarboxamide consiting of acetamide having the oxygen replaced by sulfur.	2.02	1	0	thiocarboxamide	hepatotoxic agent
tempo TEMPO: structure. TEMPO : A member of the class of aminoxyls that is piperidine that carries an oxidanediyl group at position 1 and methyl groups at positions 2, 2, 6, and 6, respectively.	2.07	1	0	aminoxyls; piperidines	catalyst; ferroptosis inhibitor; radical scavenger
tamoxifen [no description available]	1.98	1	0	stilbenoid; tertiary amino compound	angiogenesis inhibitor; antineoplastic agent; bone density conservation agent; EC 1.2.3.1 (aldehyde oxidase) inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; estrogen antagonist; estrogen receptor antagonist; estrogen receptor modulator
lithium bis(trimethylsilyl)amide lithium bis(trimethylsilyl)amide: structure in first source	2.13	1	0
nadp [no description available]	2	1	0
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	3.38	6	0
1-propan-2-yl-5-benzotriazolecarboxylic acid [no description available]	2.07	1	0	benzotriazoles
ethionamide Ethionamide: A second-line antitubercular agent that inhibits mycolic acid synthesis.. ethionamide : A thiocarboxamide that is pyridine-4-carbothioamide substituted by an ethyl group at position 2. A prodrug that undergoes metabolic activation by conversion to the corresponding S-oxide.	7.41	1	0	pyridines; thiocarboxamide	antilipemic drug; antitubercular agent; fatty acid synthesis inhibitor; leprostatic drug; prodrug
lithium Lithium: An element in the alkali metals family. It has the atomic symbol Li, atomic number 3, and atomic weight [6.938; 6.997]. Salts of lithium are used in treating BIPOLAR DISORDER.	2.03	1	0	alkali metal atom
nitrogen dioxide Nitrogen Dioxide: Nitrogen oxide (NO2). A highly poisonous gas. Exposure produces inflammation of lungs that may only cause slight pain or pass unnoticed, but resulting edema several days later may cause death. (From Merck, 11th ed) It is a major atmospheric pollutant that is able to absorb UV light that does not reach the earth's surface.	7.02	1	0	nitrogen oxide
thiophanate Thiophanate: Nematocide used in livestock; also has fungicidal properties.. thiophanate : A member of the class of thioureas that is the diethyl ester of (1,2-phenylenedicarbamothioyl)biscarbamic acid. A fungicide effective against a broad spectrum of diseases in fruit, vegetables, turf and other crops including eyespot, scab, powdery mildew and grey mould.	4.11	3	1	benzimidazole precursor fungicide; carbamate ester; carbamate fungicide; thioureas	antifungal drug
orlistat Orlistat: A lactone derivative of LEUCINE that acts as a pancreatic lipase inhibitor to limit the absorption of dietary fat; it is used in the management of obesity.. orlistat : A carboxylic ester resulting from the formal condensation of the carboxy group of N-formyl-L-leucine with the hydroxy group of (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one. A pancreatic lipase inhibitor, it is used as an anti-obesity drug.	3.35	1	0	beta-lactone; carboxylic ester; formamides; L-leucine derivative	anti-obesity agent; bacterial metabolite; EC 2.3.1.85 (fatty acid synthase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor
azoxystrobin azoxystrobin: a methoxyacrylate analog; a strobilurin fungicide; structure given in first source. azoxystrobin : An aryloxypyrimidine having a 4,6-diphenoxypyrimidine skeleton in which one of the phenyl rings is cyano-substituted at C-2 and the other carries a 2-methoxy-1-(methoxycarbonyl)vinyl substituent, also at C-2. An inhibitor of mitochondrial respiration by blocking electron transfer between cytochromes b and c1, it is used widely as a fungicide in agriculture.	2.04	1	0	aryloxypyrimidine; enoate ester; enol ether; methoxyacrylate strobilurin antifungal agent; methyl ester; nitrile	antifungal agrochemical; environmental contaminant; mitochondrial cytochrome-bc1 complex inhibitor; quinone outside inhibitor; xenobiotic
brassinin [no description available]	2.07	1	0	dithiocarbamic ester; indole phytoalexin
rasagiline [no description available]	2.25	1	0	indanes; secondary amine; terminal acetylenic compound	EC 1.4.3.4 (monoamine oxidase) inhibitor; neuroprotective agent
ha 1100 HA 1100: intracellular calcium antagonist	2.06	1	0
calixarenes Calixarenes: Phenolic metacyclophanes derived from condensation of PHENOLS and ALDEHYDES. The name derives from the vase-like molecular structures. A bracketed [n] indicates the number of aromatic rings.. calixarenes : Originally macrocyclic compounds capable of assuming a basket (or "calix") shaped conformation. They are formed from p-hydrocarbyl phenols and formaldehyde. The term now applies to a variety of derivatives by substitution of the hydrocarbon cyclo{oligo[(1,3-phenylene)methylene]}.. calixarene : A macrocycle composed of 1,3-phenylene groups linked by methylene groups. The number of 1,3-phenylene units in the macrocycle is denoted by the "n" in calix[n]arene name.	2.48	2	0
dipyrromethene dipyrromethene: structure in first source. dipyrrin : A dipyrrin that consists of pyrrole bearing a pyrrol-2-ylidenemethyl substituent at the 2-position.	2.1	1	0	dipyrrins
phosphonic acid phosphonic acid : A phosphorus oxoacid that consists of a single pentavalent phosphorus covalently bound via single bonds to a single hydrogen and two hydroxy groups and via a double bond to an oxygen. The parent of the class of phosphonic acids.	2.11	1	0
ginsenosides ginsenoside : Triterpenoid saponins with a dammarane-like skeleton originally isolated from ginseng (Panax) species. Use of the term has been extended to include semi-synthetic derivatives.	3.27	1	0
3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol 3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol: (-)-CP-55,940 and (+)-CP-56,667 are enantiomers; RN refers to CP-55,940	2.11	1	0	alkylbenzene; ring assembly
9-(2-morpholinoethyl)-2-(4-fluorophenyl)imidazo(1,2-alpha)benzimidazole [no description available]	2.17	1	0
4,5,6,7-tetrabromobenzimidazole 4,5,6,7-tetrabromobenzimidazole: structure in first source	2.02	1	0
quercetin [no description available]	7.1	1	0	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	2.39	2	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
beta carotene beta Carotene: A carotenoid that is a precursor of VITAMIN A. Beta carotene is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (PORPHYRIA, ERYTHROPOIETIC).. provitamin A : A provitamin that can be converted into vitamin A by enzymes from animal tissues.	3.34	1	1	carotenoid beta-end derivative; cyclic carotene	antioxidant; biological pigment; cofactor; ferroptosis inhibitor; human metabolite; mouse metabolite; plant metabolite; provitamin A
thromboxane a2 Thromboxane A2: An unstable intermediate between the prostaglandin endoperoxides and thromboxane B2. The compound has a bicyclic oxaneoxetane structure. It is a potent inducer of platelet aggregation and causes vasoconstriction. It is the principal component of rabbit aorta contracting substance (RCS).. thromboxane A2 : A thromboxane which is produced by activated platelets and has prothrombotic properties: it stimulates activation of new platelets as well as increases platelet aggregation.	1.96	1	0	epoxy monocarboxylic acid; thromboxanes A	mouse metabolite
pyrantel pamoate Pyrantel Pamoate: Broad spectrum antinematodal anthelmintic used also in veterinary medicine.	2.02	1	0	organic molecular entity
7-hydroxycoumarin 7-oxycoumarin: derivatives have anti-oxidant properties. umbelliferone : A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7.	2.25	1	0	hydroxycoumarin	fluorescent probe; food component; plant metabolite
anandamide anandamide : An N-acylethanolamine 20:4 resulting from the formal condensation of carboxy group of arachidonic acid with the amino group of ethanolamine.	2.03	1	0	endocannabinoid; N-acylethanolamine 20:4	human blood serum metabolite; neurotransmitter; vasodilator agent
6-methylpurine 6-methylpurine : Purine bearing a methyl substituent at position 6.	7	1	0	purines	EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor
pyoverdin pyoverdin: a partly cyclic octapeptide linked to a chromophore, derived from 2,3-diamino-6,7-dihydroxyquinoline, which confers color and fluorescence to the molecule; yellow-green pigment produced by Pseudomonas aeruginosa; pyoverdin Pf from P. fluorescens; structure has been determined	2.21	1	0
nalbuphine Nalbuphine: A narcotic used as a pain medication. It appears to be an agonist at KAPPA RECEPTORS and an antagonist or partial agonist at MU RECEPTORS.	2.31	1	0	organic heteropentacyclic compound	mu-opioid receptor antagonist; opioid analgesic
andrographolide [no description available]	3.41	1	0	carbobicyclic compound; gamma-lactone; labdane diterpenoid; primary alcohol; secondary alcohol	anti-HIV agent; anti-inflammatory drug; antineoplastic agent; metabolite
casein kinase ii Casein Kinase II: A ubiquitous casein kinase that is comprised of two distinct catalytic subunits and dimeric regulatory subunit. Casein kinase II has been shown to phosphorylate a large number of substrates, many of which are proteins involved in the regulation of gene expression.	3.46	7	0
su 11248 [no description available]	2.11	1	0	monocarboxylic acid amide; pyrroles	angiogenesis inhibitor; antineoplastic agent; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; immunomodulator; neuroprotective agent; vascular endothelial growth factor receptor antagonist
morantel Morantel: Antinematodal agent used mainly for livestock.	6.98	1	0
diamide Diamide: A sulfhydryl reagent which oxidizes sulfhydryl groups to the disulfide form. It is a radiation-sensitizing agent of anoxic bacterial and mammalian cells.	2.06	1	0	1,1'-azobis(N,N-dimethylformamide)
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	2.71	3	0	boron group element atom; elemental aluminium; metal atom
bismuth Bismuth: A metallic element that has the atomic symbol Bi, and atomic number 83. Its principal isotope is Bismuth 209.	2.17	1	0	metal atom; pnictogen
sulfur Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.	2.75	3	0	chalcogen; nonmetal atom	macronutrient
piperic acid piperinic acid: from Piper longum; structure in first source. (E,E)-piperic acid : A monocarboxylic acid that is (E)-penta-2,4-dienoic acid substituted by a 1,3-benzodioxol-5-yl group at position 5. It has been isolated from black pepper (Piper nigrum).	2.25	1	0	alpha,beta-unsaturated monocarboxylic acid; benzodioxoles	plant metabolite
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	7.41	1	0	cysteinium	fundamental metabolite
boron Boron: A trace element with the atomic symbol B, atomic number 5, and atomic weight [10.806; 10.821]. Boron-10, an isotope of boron, is used as a neutron absorber in BORON NEUTRON CAPTURE THERAPY.	7.78	3	0	boron group element atom; metalloid atom; nonmetal atom	micronutrient
s-trans,trans-farnesylthiosalicylic acid farnesylthiosalicylic acid: structure in first source	3.41	1	0	sesquiterpenoid
selenium Selenium: An element with the atomic symbol Se, atomic number 34, and atomic weight 78.97. It is an essential micronutrient for mammals and other animals but is toxic in large amounts. Selenium protects intracellular structures against oxidative damage. It is an essential component of GLUTATHIONE PEROXIDASE.	2.47	2	0	chalcogen; nonmetal atom	micronutrient
pyrachlostrobin pyraclostrobin : A carbamate ester that is the methyl ester of [2-({[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}methyl)phenyl]methoxycarbamic acid. A fungicide used to control major plant pathogens including Septoria tritici, Puccinia spp. and Pyrenophora teres.	2.08	1	0	aromatic ether; carbamate ester; carbanilate fungicide; methoxycarbanilate strobilurin antifungal agent; monochlorobenzenes; pyrazoles	antifungal agrochemical; environmental contaminant; mitochondrial cytochrome-bc1 complex inhibitor; xenobiotic
rhizoxin rhizoxin: from Rhizopus chinensis; causal agent of rice seedling blight; structure given in first source. rhizoxin : An macrolide antibiotic isolated from the pathogenic plant fungus Rhizopus microsporus. It also exhibits antitumour and antimitotic activity.	1.97	1	0	1,3-oxazoles; epoxide; macrolide antibiotic	antimitotic; antineoplastic agent; metabolite
manumycin manumycin: an NSAID; RN given for (1S-(1alpha,3(2E,4E,6S*),5alpha,5(1E,3E,5E),6alpha))-isomer; a farnesyl protein transferase inhibitor; from Streptomyces parvulus; MF C31-H38-N2-O7; structure given in first source. manumycin A : A polyketide with formula C31H38N2O7 initially isolated from Streptomyces parvulus as a result of a random screening program for farnesyl transferase (FTase) inhibitors. It is a natural product that exhibits anticancer and antibiotic properties.	3.41	1	0	enamide; epoxide; organic heterobicyclic compound; polyketide; secondary carboxamide; tertiary alcohol	antiatherosclerotic agent; antimicrobial agent; antineoplastic agent; apoptosis inducer; bacterial metabolite; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.5.1.58 (protein farnesyltransferase) inhibitor; marine metabolite
ispinesib [no description available]	2.05	1	0	benzamides
mannich bases Mannich Bases: Ketonic amines prepared from the condensation of a ketone with formaldehyde and ammonia or a primary or secondary amine. A Mannich base can act as the equivalent of an alpha,beta unsaturated ketone in synthesis or can be reduced to form physiologically active amino alcohols.	7.53	2	0
6-(7-nitro-2,1,3-benzoxadiazol-4-ylthio)hexanol 6-(7-nitro-2,1,3-benzoxadiazol-4-ylthio)hexanol: a specific glutathione S-transferase inhibitor; structure in first source	3.35	1	0
sb 705498 SB 705498: structure in first source	3.14	1	0
cc 1065 CC 1065: from Streptomyces zelensis; structure in second sourc	3.1	1	0
zeolites [no description available]	2.06	1	0
aluminum oxide Aluminum Oxide: An oxide of aluminum, occurring in nature as various minerals such as bauxite, corundum, etc. It is used as an adsorbent, desiccating agent, and catalyst, and in the manufacture of dental cements and refractories.	2.06	1	0
alpha-synuclein alpha-Synuclein: A synuclein that is a major component of LEWY BODIES and plays a role in SYNUCLEINOPATHIES, neurodegeneration and neuroprotection.	2.52	2	0
oxadiazoles Oxadiazoles: Compounds containing five-membered heteroaromatic rings containing two carbons, two nitrogens, and one oxygen atom which exist in various regioisomeric forms.	7.69	3	0
oxazolopyridinone oxazolopyridinone: structure in first source	2.31	1	0
ribose ribopyranose : The pyranose form of ribose.	2	1	0	D-ribose; ribopyranose
pyrazolone pyrazolone: non-steroid antirheumatic agent. pyrazolone : A member of the class of pyrazoles in which one of the carbons of the pyrazole ring is substituted by an oxo group.	7.53	2	0
sitagliptin phosphate Sitagliptin Phosphate: A pyrazine-derived DIPEPTIDYL-PEPTIDASE IV INHIBITOR and HYPOGLYCEMIC AGENT that increases the levels of the INCRETIN hormones GLUCAGON-LIKE PEPTIDE-1 (GLP-1) and glucose-dependent insulinotropic polypeptide (GIP). It is used in the treatment of TYPE 2 DIABETES.	2.05	1	0
td-5108 TD-5108: a selective 5-HT(4) receptor agonist with high intrinsic activity; structure in first source	2.08	1	0
doramectin [no description available]	2	1	0	macrolide
dextrothyroxine [no description available]	9.39	44	3
rifamycins [no description available]	2.1	1	0
thienopyrimidine thienopyrimidine: structure in first source. thienopyrimidine : A class of aromatic heterobicyclic compounds each of which contains a pyrimidine ring ortho fused to a 5-membered thiophene ring.	2.52	2	0
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	2.68	3	0	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
bms-650032 asunaprevir: an NS3 protease inhibitor against hepatitis C virus	5.91	2	2	oligopeptide
sch 54292 SCH 54292: structure in first source	3.41	1	0
histogranin histogranin: NMDA receptor antagonist isolated from bovine adrenal medulla; amino acid sequence given in first source	7.02	1	0
gastrins Gastrins: A family of gastrointestinal peptide hormones that excite the secretion of GASTRIC JUICE. They may also occur in the central nervous system where they are presumed to be neurotransmitters.	1.96	1	0
tannins Tannins: Polyphenolic compounds with molecular weights of around 500-3000 daltons and containing enough hydroxyl groups (1-2 per 100 MW) for effective cross linking of other compounds (ASTRINGENTS). The two main types are HYDROLYZABLE TANNINS and CONDENSED TANNINS. Historically, the term has applied to many compounds and plant extracts able to render skin COLLAGEN impervious to degradation. The word tannin derives from the Celtic word for OAK TREE which was used for leather processing.	1.99	1	0
oligonucleotides [no description available]	2.1	1	0
glucagon-like peptide 1 Glucagon-Like Peptide 1: A peptide of 36 or 37 amino acids that is derived from PROGLUCAGON and mainly produced by the INTESTINAL L CELLS. GLP-1(1-37 or 1-36) is further N-terminally truncated resulting in GLP-1(7-37) or GLP-1-(7-36) which can be amidated. These GLP-1 peptides are known to enhance glucose-dependent INSULIN release, suppress GLUCAGON release and gastric emptying, lower BLOOD GLUCOSE, and reduce food intake.	2.05	1	0
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	7.17	1	0	glycoside
chlorophyll a Chlorophyll: Porphyrin derivatives containing magnesium that act to convert light energy in photosynthetic organisms.. chlorophyll : A family of magnesium porphyrins, defined by the presence of a fifth ring beyond the four pyrrole-like rings. The rings can have various side chains which usually include a long phytol chain.	2.17	1	0	chlorophyll; methyl ester	cofactor
hoe 33342 bisbenzimide ethoxide trihydrochloride: benzimidazole fluorescent dye	2	1	0
rs 39604 RS 39604 hydrochloride : A hydrochloride salt obtained by mixing equimolar amounts of RS 39604 with hydrochloric acid. A potent and selective 5-HT4 antagonist, with a pKi of 9.1 at 5-HT4 receptors in guinea pig striatal membranes and greater than 1000-fold selectivity over 5-HT1A, 2C, 3 and D1, D2, M1, M2, AT1, B1 and alpha1C receptors. The ketone group gives RS 39604 a relatively long half life; it is also orally active and so suitable for in vivo studies.. RS 39604 : An aromatic ether that is the 3,5-dimethoxybenzyl derivative of N-(2-{4-[3-(4-amino-5-chloro-2-hydroxyphenyl)-3-oxopropyl]piperidin-1-yl}ethyl)methanesulfonamide. A potent and selective 5-HT4 antagonist, with a pKi of 9.1 at 5-HT4 receptors in guinea pig striatal membranes and greater than 1000-fold selectivity over 5-HT1A, 2C, 3 and D1, D2, M1, M2, AT1, B1 and alpha1C receptors. The ketone group gives RS 39604 a relatively long half life; it is also orally active and so suitable for in vivo studies.	2.01	1	0	hydrochloride	serotonergic antagonist
chitosan [no description available]	2.31	1	0
tert-butoxide, potassium [no description available]	2.08	1	0
chiniofon Hydroxyquinolines: The 8-hydroxy derivatives inhibit various enzymes and their halogenated derivatives, though neurotoxic, are used as topical anti-infective agents, among other uses.	2.15	1	0
hygromycin b [no description available]	2.1	1	0
srt1720 [no description available]	3.27	1	0
cx 4945 [no description available]	2.17	1	0
s-adenosylmethionine (R)-S-adenosyl-L-methionine : An S-adenosyl-L-methionine that has R-configuration.. S-adenosyl-L-methionine zwitterion : A zwitterionic tautomer of S-adenosyl-L-methionine arising from shift of the proton from the carboxy group to the amino group.. (R)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has R-configuration; major species at pH 7.3.. (S)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has S-configuration; major species at pH 7.3.. S-adenosyl-L-methionine : A sulfonium compound that is the S-adenosyl derivative of L-methionine. It is an intermediate in the metabolic pathway of methionine.	2.13	1	0	organic cation; sulfonium compound	coenzyme; cofactor; human metabolite; micronutrient; Mycoplasma genitalium metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
picrotoxin Picrotoxin: A noncompetitive antagonist at GABA-A receptors and thus a convulsant. Picrotoxin blocks the GAMMA-AMINOBUTYRIC ACID-activated chloride ionophore. Although it is most often used as a research tool, it has been used as a CNS stimulant and an antidote in poisoning by CNS depressants, especially the barbiturates.. picrotoxin : A mixture consisting of equimolar amounts of picrotoxinin and picrotin found in the climbing plant Anamirta cocculus.	2.17	1	0
intrinsic factor Intrinsic Factor: A glycoprotein secreted by the cells of the GASTRIC GLANDS that is required for the absorption of VITAMIN B 12 (cyanocobalamin). Deficiency of intrinsic factor leads to VITAMIN B 12 DEFICIENCY and ANEMIA, PERNICIOUS.	6.93	1	0
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [no description available]	2.49	2	0	BODIPY compound
cardiovascular agents Cardiovascular Agents: Agents that affect the rate or intensity of cardiac contraction, blood vessel diameter, or blood volume.	2.31	1	0
gsk 1363089 GSK 1363089: a multikinase inhibitor that acts on Met, RON, Axl, and VEGFR; structure in first source	2.17	1	0	aromatic ether
piperidines Piperidines: A family of hexahydropyridines.	3.16	5	0
monepantel monepantel: Anthelmintic; effective gainst fourth stage gastro-intestinal nematode larvae infecting sheep. monepantel : A secondary carboxamide resulting from the formal condensation of the carboxy group of p-[(trifluoromethyl)sulfanyl]benzoic acid with the amino group of (2S)-2-amino-3-hydroxy-2-methylpropanenitrile in which the hydroxy group has been converted to the corresponding 5-cyano-2-(trifluoromethyl)phenyl ether. A broad-spectrum nematicide, it is used to control gastrointestinal roundworms in sheep and goats.	2.48	2	0	(trifluoromethyl)benzenes; aromatic ether; aryl sulfide; nitrile; secondary carboxamide	anthelminthic drug; nematicide
sofosbuvir Sofosbuvir: A uridine monophosphate analog inhibitor of HEPATITIS C VIRUS (HCV) polymerase NS5B that is used as an ANTIVIRAL AGENT in the treatment of CHRONIC HEPATITIS C.. sofosbuvir : A nucleotide conjugate that is used in combination with ledipasvir (under the trade name Harvoni) for the treatment of chronic hepatitis C genotype 1 infection.	9.13	7	7	isopropyl ester; L-alanyl ester; nucleotide conjugate; organofluorine compound; phosphoramidate ester	antiviral drug; hepatitis C protease inhibitor; prodrug
heme Heme: The color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins.. ferroheme : Any iron(II)--porphyrin coordination complex.. ferroheme b : Heme b in which the iron has oxidation state +2.. heme : A heme is any tetrapyrrolic chelate of iron.	7.37	2	0
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	2.15	1	0	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
novobiocin Novobiocin: An antibiotic compound derived from Streptomyces niveus. It has a chemical structure similar to coumarin. Novobiocin binds to DNA gyrase, and blocks adenosine triphosphatase (ATPase) activity. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p189). novobiocin : A coumarin-derived antibiotic obtained from Streptomyces niveus.	2.07	1	0	carbamate ester; ether; hexoside; hydroxycoumarin; monocarboxylic acid amide; monosaccharide derivative; phenols	antibacterial agent; antimicrobial agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; Escherichia coli metabolite; hepatoprotective agent
piroxicam [no description available]	2.25	1	0	benzothiazine; monocarboxylic acid amide; pyridines	analgesic; antirheumatic drug; cyclooxygenase 1 inhibitor; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-steroidal anti-inflammatory drug
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	4.49	6	0	benzenes; hydroxycoumarin; methyl ketone
kaolinite Kaolin: The most common mineral of a group of hydrated aluminum silicates, approximately H2Al2Si2O8-H2O. It is prepared for pharmaceutical and medicinal purposes by levigating with water to remove sand, etc. (From Merck Index, 11th ed) The name is derived from Kao-ling (Chinese: high ridge), the original site. (From Grant & Hackh's Chemical Dictionary, 5th ed). kaolin : An aluminosilicate soft white mineral named after the hill in China (Kao-ling) from which it was mined for centuries. In its natural state kaolin is a white, soft powder consisting principally of the mineral kaolinite, and varying amounts of other minerals such as muscovite, quartz, feldspar, and anatase. It is used in the manufacture of china and porcelain and also widely used in the production of paper, rubber, paint, drying agents, and many other products.	2.31	1	0	aluminosilicate mineral; mixture	antidiarrhoeal drug; excipient
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	2.41	2	0
hyaluronoglucosaminidase Hyaluronoglucosaminidase: An enzyme that catalyzes the random hydrolysis of 1,4-linkages between N-acetyl-beta-D-glucosamine and D-glucuronate residues in hyaluronate. (From Enzyme Nomenclature, 1992) There has been use as ANTINEOPLASTIC AGENTS to limit NEOPLASM METASTASIS.	2.04	1	0
vitamin b 12 Vitamin B 12: A cobalt-containing coordination compound produced by intestinal micro-organisms and found also in soil and water. Higher plants do not concentrate vitamin B 12 from the soil and so are a poor source of the substance as compared with animal tissues. INTRINSIC FACTOR is important for the assimilation of vitamin B 12.	3.04	5	0
moxidectin moxidectin: family of macrolide antibiotics with insecticidal & acaricidal activity	3.83	11	0
cyclosporine Cyclosporine: A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).	3.35	1	0
muramidase Muramidase: A basic enzyme that is present in saliva, tears, egg white, and many animal fluids. It functions as an antibacterial agent. The enzyme catalyzes the hydrolysis of 1,4-beta-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrin. EC 3.2.1.17.	2.1	1	0
guanosine diphosphate Guanosine Diphosphate: A guanine nucleotide containing two phosphate groups esterified to the sugar moiety.	2.17	1	0	guanosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor
guanosine triphosphate Guanosine Triphosphate: Guanosine 5'-(tetrahydrogen triphosphate). A guanine nucleotide containing three phosphate groups esterified to the sugar moiety.	2.17	1	0	guanosine 5'-phosphate; purine ribonucleoside 5'-triphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor
guanine [no description available]	3.07	5	0	2-aminopurines; oxopurine; purine nucleobase	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanosine ribonucleoside : Any nucleoside where the sugar component is D-ribose.	7.03	1	0	guanosines; purines D-ribonucleoside	fundamental metabolite
inosinic acid Inosine Monophosphate: Inosine 5'-Monophosphate. A purine nucleotide which has hypoxanthine as the base and one phosphate group esterified to the sugar moiety.	2.07	1	0	inosine phosphate; purine ribonucleoside 5'-monophosphate	Escherichia coli metabolite; human metabolite; mouse metabolite
folic acid folcysteine: used to promote fertility in chickens. vitamin B9 : Any B-vitamin that exhibits biological activity against vitamin B9 deficiency. Vitamin B9 refers to the many forms of folic acid and its derivatives, including tetrahydrofolic acid (the active form), methyltetrahydrofolate (the primary form found in blood), methenyltetrahydrofolate, folinic acid amongst others. They are present in abundance in green leafy vegetables, citrus fruits, and animal products. Lack of vitamin B9 leads to anemia, a condition in which the body cannot produce sufficient number of red blood cells. Symptoms of vitamin B9 deficiency include fatigue, muscle weakness, and pale skin.	7.67	3	0	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
rifampin Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)	2.46	2	0	cyclic ketal; hydrazone; N-iminopiperazine; N-methylpiperazine; rifamycins; semisynthetic derivative; zwitterion	angiogenesis inhibitor; antiamoebic agent; antineoplastic agent; antitubercular agent; DNA synthesis inhibitor; EC 2.7.7.6 (RNA polymerase) inhibitor; Escherichia coli metabolite; geroprotector; leprostatic drug; neuroprotective agent; pregnane X receptor agonist; protein synthesis inhibitor
dacarbazine (E)-dacarbazine : A dacarbazine in which the N=N double bond adopts a trans-configuration.	2.13	1	0	dacarbazine
allopurinol Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.	2.54	2	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
4-hydroxyquinazoline 4-oxo-3,4-dihydroquinazoline: structure in first source	2.03	1	0	quinazolines
2-amino-4-hydroxy-6-formylpteridine 2-amino-4-hydroxy-6-formylpteridine: pteridine precursor in biosynthesis of dihydropteroate; structure. 6-formylpterin : Pterin carrying a formyl group at position 6.	1.93	1	0	aldehyde; pterins	EC 1.17.3.2 (xanthine oxidase) inhibitor; reactive oxygen species generator
bms 536924 BMS 536924: inhibits insulin-like growth factor I receptor kinase; structure in first source	2.05	1	0
7-methylguanosine-5'-monophosphate 7-methylguanosine 5'-phosphate(1-) : An organophosphate oxoanion arising from deprotonation of the phosphate OH groups of 7-methylguanosine 5'-phosphate; major species at pH 7.3.	2	1	0	organophosphate oxoanion
ARS-1620 ARS-1620: covalent S-IIP G12C inhibitor for targeting of KRAS G12C mutant tumors. ARS-1620 : A qinazoline derivative carrying chloro and fluoro substituents at positions 6 and 8 respectively, a 2-fluoro-6-hydroxyphenyl group at position 7, and a 4-(prop-2-enoyl)piperazin-1-yl group at position 4. A potent, selective, and orally bioavailable covalent KRAS-G12C inhibitor, it inhibits the protein coding gene KRAS (Kirsten rat sarcoma virus) with high potency in cells and animals.	3.41	1	0	quinazolines	antineoplastic agent; antiviral agent; inhibitor
avermectin avermectin: produced by actinomycete, Streptomyces avermitilis; structure; see also records for specific avermectins. avermectin : Any of the macrolides obtained as fermentation products from the bacterium Streptomyces avermitilis and consisting of a 16-membered macrocyclic backbone that is fused both benzofuran and spiroketal functions and contains a disaccharide substituent. They have significant anthelmintic and insecticidal properties.	10.78	6	1
concanavalin a Concanavalin A: A MANNOSE/GLUCOSE binding lectin isolated from the jack bean (Canavalia ensiformis). It is a potent mitogen used to stimulate cell proliferation in lymphocytes, primarily T-lymphocyte, cultures.	2	1	0
pyrimidinones Pyrimidinones: Heterocyclic compounds known as 2-pyrimidones (or 2-hydroxypyrimidines) and 4-pyrimidones (or 4-hydroxypyrimidines) with the general formula C4H4N2O.	2.08	1	0

benzimidazole

Description

Cross-References

Synonyms (84)

Research Excerpts

Overview

Effects

Actions

Treatment

Toxicity

Pharmacokinetics

Bioavailability

Dosage Studied

Drug Classes (2)

Pathways (1)

Protein Targets (15)

Potency Measurements

Inhibition Measurements

Activation Measurements

Other Measurements

Biological Processes (35)

Molecular Functions (21)

Ceullar Components (19)

Bioassays (96)

Research

Studies (1,163)

Market Indicators

Research Demand Index: 67.93

Study Types

Clinical Trials (6)

Trial Overview

Trial Outcomes

Measure of β-diversity of the Gut Microbiota Between Baseline and EOT Stool Samples (Bray-Curtis Index/Dissimilarity).

Percentage of Change of α-diversity (Shannon Index) of the Microbiota in Stool Samples From Baseline to EOT.

Clinical Cure

Clinical Response

Number of Participants With Sustained Clinical Response (SCR) Defined as Clinical Response and no Recurrence of CDI Through 30 Days Post End of Treatment (EOT).

Relative Abundance of the 3 Main Bile Acid Groups (Conjugated Primary, Primary and Secondary Bile Acids) From Baseline to EOT.

Sustained Clinical Response Over 60 Days

Sustained Clinical Response Over 90 Days

Condition	Relationship Strength	Studies	Trials
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.	2.69	3	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	5.23	6	2
Hepatitis B Virus Infection [description not available]	2.02	1	0
Hepatitis B INFLAMMATION of the LIVER in humans caused by a member of the ORTHOHEPADNAVIRUS genus, HEPATITIS B VIRUS. It is primarily transmitted by parenteral exposure, such as transfusion of contaminated blood or blood products, but can also be transmitted via sexual or intimate personal contact.	2.02	1	0
Innate Inflammatory Response [description not available]	3.69	3	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.	3.69	3	0
Infections, Helicobacter [description not available]	2.44	2	0
Gastritis Inflammation of the GASTRIC MUCOSA, a lesion observed in a number of unrelated disorders.	2.07	1	0
Helicobacter Infections Infections with organisms of the genus HELICOBACTER, particularly, in humans, HELICOBACTER PYLORI. The clinical manifestations are focused in the stomach, usually the gastric mucosa and antrum, and the upper duodenum. This infection plays a major role in the pathogenesis of type B gastritis and peptic ulcer disease.	2.44	2	0
Alloxan Diabetes [description not available]	2.75	3	0
Central Retinal Edema, Cystoid [description not available]	2.08	1	0
Diabetic Retinopathy Disease of the RETINA as a complication of DIABETES MELLITUS. It is characterized by the progressive microvascular complications, such as ANEURYSM, interretinal EDEMA, and intraocular PATHOLOGIC NEOVASCULARIZATION.	2.08	1	0
Macular Edema Fluid accumulation in the outer layer of the MACULA LUTEA that results from intraocular or systemic insults. It may develop in a diffuse pattern where the macula appears thickened or it may acquire the characteristic petaloid appearance referred to as cystoid macular edema. Although macular edema may be associated with various underlying conditions, it is most commonly seen following intraocular surgery, venous occlusive disease, DIABETIC RETINOPATHY, and posterior segment inflammatory disease. (From Survey of Ophthalmology 2004; 49(5) 470-90)	2.08	1	0
Plasmodium falciparum Malaria [description not available]	2.78	3	0
Malaria, Falciparum Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.	2.78	3	0
Giardia duodenalis Infection [description not available]	4.93	5	0
Giardiasis An infection of the SMALL INTESTINE caused by the flagellated protozoan GIARDIA. It is spread via contaminated food and water and by direct person-to-person contact.	4.93	5	0
ER-Negative PR-Negative HER2-Negative Breast Cancer [description not available]	2.96	3	0
Cancer of Lung [description not available]	3.26	5	0
Lung Neoplasms Tumors or cancer of the LUNG.	3.26	5	0
Triple Negative Breast Neoplasms Breast neoplasms that do not express ESTROGEN RECEPTORS; PROGESTERONE RECEPTORS; and do not overexpress the NEU RECEPTOR/HER-2 PROTO-ONCOGENE PROTEIN.	2.96	3	0
Acute Confusional Senile Dementia [description not available]	3.77	9	0
Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)	3.77	9	0
Ascariasis Infection by nematodes of the genus ASCARIS. Ingestion of infective eggs causes diarrhea and pneumonitis. Its distribution is more prevalent in areas of poor sanitation and where human feces are used for fertilizer.	3.13	5	0
Cystic Echinococcosis [description not available]	13.38	12	1
Benign Neoplasms [description not available]	5.99	17	0
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	5.99	17	0
Helminthiasis, Animal Infestation of animals with parasitic worms of the helminth class. The infestation may be experimental or veterinary.	3.33	6	0
Hepatocellular Carcinoma [description not available]	3.22	5	0
Cancer of Liver [description not available]	4.3	6	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.	3.22	5	0
Liver Neoplasms Tumors or cancer of the LIVER.	4.3	6	0
Ovine Diseases [description not available]	9.33	73	5
Angiostrongylus Infections [description not available]	3.85	11	0
African Sleeping Sickness [description not available]	2.59	2	0
Trypanosomiasis, African A disease endemic among people and animals in Central Africa. It is caused by various species of trypanosomes, particularly T. gambiense and T. rhodesiense. Its second host is the TSETSE FLY. Involvement of the central nervous system produces African sleeping sickness. Nagana is a rapidly fatal trypanosomiasis of horses and other animals.	2.59	2	0
Carcinoma, Non-Small Cell Lung [description not available]	2.21	1	0
Carcinoma, Non-Small-Cell Lung A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.	2.21	1	0
Margins of Excision The edges of tissue removed in a surgery for assessment of the effectiveness of a surgical procedure in achieving the local control of a neoplasm and the adequacy of tumor removal. When the margin is negative or not involved by tumor (e.g., CANCER) it suggests all of the tumor has been removed by the surgery.	3.17	1	0
Alveolar Echinococcosis, Hepatic [description not available]	8.56	15	1

benzimidazole

Description

Cross-References

Synonyms (84)

Research Excerpts

Overview

Effects

Actions

Treatment

Toxicity

Pharmacokinetics

Bioavailability

Dosage Studied

Drug Classes (2)

Pathways (1)

Protein Targets (15)

Potency Measurements

Inhibition Measurements

Activation Measurements

Other Measurements

Biological Processes (35)

Molecular Functions (21)

Ceullar Components (19)

Bioassays (96)

Research

Studies (1,163)

Market Indicators

Research Demand Index: 67.93

Study Types

Clinical Trials (6)

Trial Overview

Trial Outcomes

Measure of β-diversity of the Gut Microbiota Between Baseline and EOT Stool Samples (Bray-Curtis Index/Dissimilarity).

Percentage of Change of α-diversity (Shannon Index) of the Microbiota in Stool Samples From Baseline to EOT.

Clinical Cure

Clinical Response

Number of Participants With Sustained Clinical Response (SCR) Defined as Clinical Response and no Recurrence of CDI Through 30 Days Post End of Treatment (EOT).

Relative Abundance of the 3 Main Bile Acid Groups (Conjugated Primary, Primary and Secondary Bile Acids) From Baseline to EOT.

Sustained Clinical Response Over 60 Days

Sustained Clinical Response Over 90 Days

Related Drugs (646)

Related Conditions (275)