isatin profile

Isatin is a heterocyclic compound with a structure similar to indigo. It occurs naturally in some plants and is synthesized by the oxidation of indole. Isatin has been studied for its potential medicinal properties, including its ability to inhibit cancer cell growth and to act as an anti-inflammatory agent. The compound is also used in the synthesis of other pharmaceuticals and dyes. Isatin has been shown to have a variety of biological activities, including antioxidant, anti-inflammatory, and anti-cancer effects. It is also used in the synthesis of other pharmaceuticals and dyes. Its importance lies in its potential as a drug candidate for a variety of diseases, including cancer, Alzheimer's disease, and Parkinson's disease.'

tribulin: endogenous MONOAMINE OXIDASE inhibitory activity extractable into ethyl acetate found in brain and many mammalian tissues and fluids; ISATIN is a major component; produced in excess following alcohol withdrawal; [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Related Flora

Flora	Rank	Flora Definition	Family	Family Definition
Indigo	genus	[no description available]	Fabaceae	The large family of plants characterized by pods. Some are edible and some cause LATHYRISM or FAVISM and other forms of poisoning. Other species yield useful materials like gums from ACACIA and various LECTINS like PHYTOHEMAGGLUTININS from PHASEOLUS. Many of them harbor NITROGEN FIXATION bacteria on their roots. Many but not all species of beans belong to this family.[MeSH]

ID Source	ID
PubMed CID	7054
CHEMBL ID	326294
CHEBI ID	27539
SCHEMBL ID	34016
MeSH ID	M0011733

Synonym
MLS001066355
smr000471835
CHEBI:27539 ,
nsc 9262
tribulin
ai3-03111
2,3-dioxo-2,3-dihydroindole
einecs 202-077-8
brn 0383659
2,3-indolinedione
wln: t56 bmvvj
nsc9262
nsc-9262
pseudoisatin
isatic acid lactam
2,3-ketoindoline
2,3-diketoindoline
o-aminobenzoylformic anhydride
isatine
isatinic acid anhydride
isotin
indole-2,3-dione
2,3-dioxoindoline
S00335A
indoline-2,3-dione
inchi=1/c8h5no2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4h,(h,9,10,11
1h-indole-2,3-dione
91-56-5
isatin ,
isatin (compound 1)
2,3-dihydro-1h-indole-2,3-dione
DB02095
chembl326294 ,
bdbm11022
I-7800
STK387523
AC-10666
I0080
AKOS000119125
A843979
NCGC00246983-01
84788-92-1
tox21_202876
cas-91-56-5
NCGC00260422-01
dtxsid3038694 ,
dtxcid1018694
HMS2267D18
S4717
ec 202-077-8
82x95s7m06 ,
unii-82x95s7m06
5-21-10-00221 (beilstein handbook reference)
FT-0627212
AM20050218
isatin [inci]
isatin [mi]
1186480-61-4
SCHEMBL34016
2,3-dihydroindole-2,3-dione
2,3-dihydro-indole-2,3-dione
2h-indole-2,3-dione
2,3-dihydro-1h-indol-2,3-dione
mfcd00005718
HY-Y0265
F9995-1662
I-7801
isatin, for spectrophotometric det. of proline and thiophene, >=99.0%
3-hydroxy-2-indolone
hydroxy-3-indolone
D70304
isatin, technical grade
isatin, p.a.
SY005277
FT-0728767
CS-W020128
BCP15996
indoline-2,3-dione;2,3-dioxo-2,3-dihydroindole; isatic acid lactam; isotin
Q421348
EN300-17956
3-indolinedione
AS-10908
HMS3885P18
CCG-266182
BB 0295136
indole-2
indol-2
SB64041

Excerpt	Reference	Relevance
"Isatin is a selective inhibitor of monoamine oxidase B."	( [Tribulin--a novel endogenous monoaminoxidase inhibitor (dedicated to the memory of Merton Sandler)]. Medvedev, AR, )	0.85
"Isatin is an endogenous selective inhibitor of MAO-B (K1 approximately 3 microM)."	( Function of endogenous monoamine oxidase inhibitors (tribulin). Glover, V, 1998)	1.02
"Isatin is an endogenous indole which was initially derived from a tribulin fraction."	( [Monoamine oxidase, tribulin, isatin: basic and applied medical aspects]. Medvedev, AE, 1999)	1.31
"Isatin is a known compound with a broad range of biological activity; this is the first report of its presence in the animal body."	( Isatin: identity with the purified endogenous monoamine oxidase inhibitor tribulin. Clow, A; Glover, V; Goodwin, BL; Halket, JM; Sandler, M; Watkins, PJ, 1988)	2.44
"Isatin (IST) is an endogenous molecule that is a principal class of heterocyclic compounds and exhibits a wide range of therapeutic activities which can be used as a starting material for the synthesis of several drug molecules. "	( In-vitro Evaluation of Isatin Derivatives as Potent Anti-Breast Cancer Agents against MCF-7, MDA MB 231, MDA-MB 435 and MDA-MB 468 Breast Cancers Cell Lines: A Review. Ali, F; Chauhan, G; Dubey, P; Khasimbi, S; Pathak, DP, 2022)	2.47
"Isatin is a versatile structure, and its derivatives are potent inhibitors of many enzymes and receptors."	( Moxifloxacin Derivatives with Potential Antibacterial Activity against Methicillin- Resistant Staphylococcus Aureus (MRSA). Chen, R; Guo, D; Liu, Y; Ma, T; Shi, X; Xu, Y; Xue, H; Zhang, J, 2021)	1.34
"Isatin or tribulin is an indole derivative; the compound was first obtained by Erdmann [1] and Laurent [2] and Erdmann in 1841 as a product from the oxidation of indigo dye by nitric acid and chromic acids. "	( Designing and Screening of New Schiff Bases of Isatins for Antibacterial Activity by In Silico Methods and Docking Studies. Lakshmi Manasa, G; Meghana, B; Munemma, R; Sowjanya, K; Swathi, K, 2021)	2.32
"Isatins are a class of compounds that target activated caspase-3 during apoptosis."	( One-Pot Radiosynthesis and Biological Evaluation of a Caspase-3 Selective 5-[ Aboagye, EO; Årstad, E; Carroll, L; Diocou, S; Gendron, T; Glaser, M; Pedley, RB; Rajkumar, V; Sander, K; Sin, PKB; Witney, TH; Yan, R, 2019)	1.24
"The isatin framework is a useful template for the development of novel anticancer agents. "	( Recent advances in isatin hybrids as potential anticancer agents. Ding, Z; Zeng, C; Zhou, M, 2020)	1.44
"Isatin is an endogenous indole that inhibits monoamine oxidase (MAO). "	( Possible synergies between isatin, an endogenous MAO inhibitor, and antiparkinsonian agents on the dopamine release from striatum of freely moving rats. Alfonso, M; Durán, R; Faro, LRF; Justo, LA, 2020)	2.3
"Isatin (IST) is a crucial pharmacologically active compound, chemically known as indole- 1H-2,3-dione. "	( Advances in Synthesis, Derivatization and Bioactivity of Isatin: A Review. Ali, F; Bhutani, R; Chauhan, G; Kapoor, G; Khasimbi, S; Pathak, DP, 2021)	2.31
"Isatin is an endogenous and a significant category of fused heterocyclic components and has widely been a part of several potential biologically useful synthetics. "	( Isatin: A Scaffold with Immense Biodiversity. Banerjee, S; Das, S; Mukherjee, A; Mukherjee, S; Nath, P, 2021)	3.51
"Isatin is a biofactor with different biochemical and pharmacological properties whose effects attract much attention because it is an endogenous inhibitor of the monoamine oxidase in the brain. "	( Participation of glutamatergic and nitrergic systems in the striatal dopamine release induced by isatin, a MAO inhibitor. Durán, R; Faro, LRF; Gómez, R; Justo, L, 2021)	2.28
"Isatin is an example of a privileged molecular framework, displaying a broad spectrum of biological activities, including antiviral action."	( Isatin Derivatives and Their Antiviral Properties Against Arboviruses: A Review. De Moraes Gomes, PAT; Leite, ACL; Pena, LJ, 2019)	2.68
"Isatin is a biologically active chemical produced by an Alteromonas sp."	( Design and synthesis of marine natural product-based 1H-indole-2,3-dione scaffold as a new antifouling/antibacterial agent against fouling bacteria. D'Souza, L; Majik, MS; Mascarenhas, S; Rodrigues, C, 2014)	1.12
"Isatin is an endogenous indole in mammalian tissues and fluids that is expected to have antitumor effects in human breast cancer cells. "	( The endogenous oxindole isatin induces apoptosis of MCF‑7 breast cancer cells through a mitochondrial pathway. Chen, Y; Hou, L; Jiang, Y; Ma, Z; Song, J, 2014)	2.15
"Isatin is a heterocyclic moiety which can be used for the synthesis of a large variety of heterocyclic compounds such as quinolines, indoles and as raw material for medicinal important drugs. "	( A mini review on central nervous system potential of isatin derivatives. Phogat, P; Singh, P, 2015)	2.11
"Isatin is an endogenous inhibitor of monoamine oxidase B and is found in human blood and tissue. "	( Enzymatic detection and quantification assay of isatin, a putative stress biomarker in blood. Bjerregaard-Andersen, K; Etzerodt, M; Jensen, JK; Jochimsen, B; Morth, JP; Riss, PJ; Simensen, SM; Sommer, T, 2015)	2.12
"Isatin is an endogenous indole that inhibits monoamine oxidase (MAO), being more selective for MAO-B than MAO-A isoform. "	( Effects and mechanism of action of isatin, a MAO inhibitor, on in vivo striatal dopamine release. Alfonso, M; Durán, R; Fajardo, D; Faro, LRF; Justo, LA, 2016)	2.15
"Isatin is an endogenous indole, which is increased in mammalian brain and peripheral tissues under conditions of stress. "	( [Isatin causes a rapid accumulation of ATP in synaptosomes: implication for stress and regulation of natriuretic peptide receptors]. , )	2.48
"Isatin is an important compound from the biological aspect of view. "	( QM study and conformational analysis of an isatin Schiff base as a potential cytotoxic agent. Miri, R; Mohammadi, MK; Razzaghi-asl, N, 2013)	2.1
"Isatin is an endogenous indole that influences a range of processes both in vivo and in vitro. "	( In situ imaging of specific binding of [3H]isatin in rat brain. Barritault, D; Cardona, A; Crumeyrolle-Arias, M; Glover, V; Medvedev, A, 2003)	2.02
"Isatin is an endogenous indole present in mammalian tissues and fluids. "	( Effect of acute stress and gender on isatin in rat tissues and serum. Glover, V; Igosheva, N; Matta, S, 2004)	2.04
"Isatin is an endogenous indole, which has a distinct and discontinuous distribution in the brain and exhibits a wide range of physiological and pharmacological effects. "	( Natriuretic peptide interaction with [3H]isatin binding sites in rat brain. Cardona, A; Crumeyrolle-Arias, M; Glover, V; Medvedev, A; Sandler, M, 2005)	2.04
"Isatin is an endogenous indole that is increased in stress, inhibits monoamine oxidase (MAO) B and improves bradykinesia and striatal dopamine levels in rat models of Parkinson's disease. "	( Isatin, an endogenous monoamine oxidase inhibitor, triggers a dose- and time-dependent switch from apoptosis to necrosis in human neuroblastoma cells. Glover, V; Igosheva, N; Lorz, C; Mehmet, H; O'Conner, E, 2005)	3.21
"Isatin is an endogenous compound identified in humans that possesses a wide range of biological activities. "	( Biological activities of isatin and its derivatives. Jyoti, M; Pandeya, SN; Smitha, S; Sridhar, SK, 2005)	2.07
"Isatin is an endogenous indole widely distributed in mammalian tissues and body fluids. "	( [Glycerol-3-phosphate dehydrogenase--cytosolic isatin-binding protein]. Buneeva, OA; Gnedenko, OV; Ivanov, IuD; Medvedev, AE; Medvedeva, MV; Panova, NG, )	1.83
"Isatin is a versatile compound with a diversity of effects. "	( Isatins inhibit cyclooxygenase-2 and inducible nitric oxide synthase in a mouse macrophage cell line. Fernandes, PD; Garden, SJ; Matheus, ME; Pinto, AC; Violante, Fde A, 2007)	3.23
"Isatin is an endogenous oxidized indole that influences a range of processes in vivo and in vitro. "	( Endogenous oxidized indoles share inhibitory potency against [3H]isatin binding in rat brain. Cardona, A; Crumeyrolle-Arias, M; Glover, V; Medvedev, A; Tournaire, MC, 2007)	2.02
"Isatin (ISA) is a natural material that exists in mammalian body fluids and tissues. "	( [Effects of isatin on cell cycle arrest and apoptosis of neuroblastoma cell line SH-SY5Y]. Ge, YL; Hou, L; Song, JL; Yue, W, 2008)	2.17
"Isatin is an endogenous selective inhibitor of monoamine oxidase (MAO) B, related to tribulin, whose activity and excretion in urine is increased during stress and anxiety. "	( Behavioral effects of isatin on open field activity and immobility in the forced swim test in rats. Abel, EL, 1995)	2.05
"Isatin is an endogenous indole with a distinctive distribution in brain and tissues. "	( Isatin: a link between natriuretic peptides and monoamines? Clow, A; Glover, V; Medvedev, AE; Sandler, M, 1996)	3.18
"Isatin is a reversible endogenous monoamine oxidase (MAO) inhibitor found in the brain. "	( Does isatin interact with rat brain monoamine oxidases in vivo? Axenova, LN; Medvedev, AE; Panova, NG; Zemskova, MA, 1997)	2.25
"Isatin is an endogenous compound recently discovered in mammalian tissues and body fluids. "	( [Isatin: possible role in functional interaction of natriuretic peptides and monoamines]. Glover, V; Medvedev, AE; Sandler, M, )	2.48
"Isatin is an endogenous indole and an inhibitor of atrial natriuretic peptide (ANP) receptors coupled with particulate guanylyl cyclase (GC). "	( Efficacy of isatin analogues as antagonists of rat brain and heart atrial natriuretic peptide receptors coupled to particulate guanylyl cyclase. Glover, V; Goodwin, BL; Medvedev, AE; Sandler, M, 1999)	2.13
"Isatin is an endogenous anxiogenic factor which is also a potent inhibitor of the ANP receptor."	( Stress and water balance: the roles of ANP, AVP and isatin. Bhattacharya, SK; Chakrabarti, A; Glover, V, 1998)	1.27
"Isatin is an endogenous indole which has been shown to counteract some of the effects of atrial natriuretic peptide (ANP) both in vitro and in vivo. "	( The action of isatin (2,3-dioxoindole) an endogenous indole on brain natriuretic and C-type natriuretic peptide-induced facilitation of memory consolidation in passive-avoidance learning in rats. Adamik, A; Glover, V; Telegdy, G, 2000)	2.11
"Isatin is a potent inhibitor of atrial natriuretic peptide (ANP) receptors and ANP-induced generation of cGMP in vitro. "	( Cyclic GMP excretion blocked by isatin administration under conditions of fluid overload. Adamik, A; Glover, V; Medvedev, A; Telegdy, G, 2001)	2.04
"Isatin is an endogenous compound which acts as a selective inhibitor of monoamine oxidase (MAO) B. "	( Inhibitory potency of some isatin analogues on human monoamine oxidase A and B. Clow, A; Glover, V; Goodwin, B; Halket, J; Medvedev, AE; Sandler, M, 1992)	2.02

Excerpt	Reference	Relevance
"Isatin has a wide spectrum of behavioural and metabolic effects."	( Isatin: role in stress and anxiety. Crumeyrolle-Arias, M; Glover, V; Igosheva, N; Medvedev, A, 2005)	2.49
"Isatin has recently been identified in rat tissues and normal human urine where it constitutes the major part of the endogenous monoamine oxidase inhibitor, tribulin. "	( Isatin and tribulin concentrations are increased in rabbit brain but not liver following pentylenetetrazole administration. Clow, A; Davidson, J; Glover, V; Halket, JM; Milton, AS; Sandler, M; Watkins, PJ, 1989)	3.16
"Isatins have been found to have various activities such as antiviral, antibacterial, anti-inflammatory, analgesic, anticonvulsan, antidepressant anti-HIV, fungicidal, etc."	( Designing and Screening of New Schiff Bases of Isatins for Antibacterial Activity by In Silico Methods and Docking Studies. Lakshmi Manasa, G; Meghana, B; Munemma, R; Sowjanya, K; Swathi, K, 2021)	1.6
"Isatin sulfonamides have been identified as potent inhibitors of these executing caspases."	( Isatin sulfonamides: potent caspases-3 and -7 inhibitors, and promising PET and SPECT radiotracers for apoptosis imaging. Haufe, G; Limpachayaporn, P; Schäfers, M, 2015)	2.58
"Isatin has been shown to initiate apoptotic processes in SH‑SY5Y neuroblastoma cells. "	( Isatin inhibits the proliferation and invasion of SH-SY5Y neuroblastoma cells. Chen, Z; Hou, L; Ju, C; Liu, L; Lv, Y; Song, J; Sun, W; Wang, Y; Xu, P; Zhang, L; Zhang, Z, 2016)	3.32
"Isatin has anxiogenic, sedative, anticonvulsant activities and acts as a potent antagonist on atrial natriuretic peptide receptors in vitro."	( Biological activities of isatin and its derivatives. Jyoti, M; Pandeya, SN; Smitha, S; Sridhar, SK, 2005)	1.35
"Isatin has a wide spectrum of behavioural and metabolic effects."	( Isatin: role in stress and anxiety. Crumeyrolle-Arias, M; Glover, V; Igosheva, N; Medvedev, A, 2005)	2.49
"Isatin has been found to inhibit rat kidney alkaline phosphatase (EC 3.1.3.1). "	( Isatin-enzyme interactions. VII. Mechanism of inhibition of rat kidney alkaline phosphatase. Bansal, RC; Kumar, P; Nagpaul, JP; Sharma, R; Singh, B, 1979)	3.15
"Isatin has been found to inhibit rat testicular alkaline phosphatase (EC 3.1.3.1) uncompetitively. "	( Isatin inhibition of rat testicular alkaline phosphatase. A non-allosteric phenomenon. Kumar, P, 1979)	3.15
"Isatin has been found to inhibit rat testicular alkaline phosphatase (EC 3.1.3.1). "	( Nature of inhibition of rat testicular alkaline phosphatase by isatin. Bansal, RC; Kumar, P; Nagpaul, JP; Sharma, R; Singh, B, 1978)	1.94

Excerpt	Reference	Relevance
"Isatins inhibit TNF-alpha production and iNOS and COX-2 protein expression resulting on reduced levels of NO and PGE(2)."	( Isatins inhibit cyclooxygenase-2 and inducible nitric oxide synthase in a mouse macrophage cell line. Fernandes, PD; Garden, SJ; Matheus, ME; Pinto, AC; Violante, Fde A, 2007)	2.5

Excerpt	Reference	Relevance
"Isatins are treated with Grignard reagents to yield oxindoles."	( Schwartz's Reagent-Mediated Regiospecific Synthesis of 2,3-Disubstituted Indoles from Isatins. Furman, B; Ulikowski, A, 2016)	1.38
"The isatin-treated cells underwent apoptosis and DNA fragmentation."	( Antioxidant & anticancer activities of isatin (1H-indole-2,3-dione), isolated from the flowers of Couroupita guianensis Aubl. Kathiresan, K; Kulangiappar, K; Premanathan, M; Radhakrishnan, S; Singaravelu, G; Sivakumar, T; Thirumalaiarasu, V, 2012)	1.13
"Isatin treatment (1-400 microM) for 24h induced a significant dose-dependent increase in MTT metabolism by SH-SY5Y cells in culture, but this was not due to an increase in cell division."	( Isatin, an endogenous monoamine oxidase inhibitor, triggers a dose- and time-dependent switch from apoptosis to necrosis in human neuroblastoma cells. Glover, V; Igosheva, N; Lorz, C; Mehmet, H; O'Conner, E, 2005)	2.49

Excerpt	Reference	Relevance
" Comparison of saline- and AOM-injected controls revealed that potential toxic side effects can be interpreted from blood biochemistry and hematology using this short-term model, although AOM negatively affected the ability to detect histopathological effects in the liver."	( Simultaneous Assessment of the Efficacy and Toxicity of Marine Mollusc-Derived Brominated Indoles in an In Vivo Model for Early Stage Colon Cancer. Abbott, CA; Benkendorff, K; Esmaeelian, B; Le Leu, RK, 2018)	0.48
" Chelation therapy was used to reduce the adverse effects of acute and chronic poisoning by metals."	( Protective effects of isatin and its synthetic derivatives against iron, copper and lead toxicity. Ahmadi, S; Faraji, H; Hakimi, M; Mashkani, B; Moghimi Benhangi, H; Molafilabi, A, 2019)	0.83
" In the search for compounds that interact with Aβ and disrupt its typical aggregation course toward oligomeric or polymeric toxic assemblies, small organic molecules of natural origin, combining low molecular weight (necessary blood-brain barrier penetration) and low toxicity (necessary for pharmacological application), are greatly sought after."	( Novel Isatin Thiosemicarbazone Derivatives as Potent Inhibitors of β-Amyloid Peptide Aggregation and Toxicity. Boukos, N; Kaminari, A; Mavroidi, B; Pelecanou, M; Sagnou, M, 2020)	1.04

Excerpt	Reference	Relevance
"This method has been applied successfully to a pharmacokinetic study involving the oral and intravenous administration of isatin to beagle dogs."	( Pharmacokinetic study of isatin in dog plasma by liquid chromatography tandem mass spectrometry. Ding, B; Fang, Z; Gao, M; Li, X; Liu, Z; Ren, A; Wang, H; Wang, Q; Xu, W; Yin, L; Yue, W; Zhang, J, 2015)	0.93

Excerpt	Relevance	Reference
" In this range dose-response curves become progressively flatter and their maxima decline in a non-competitive way."	( [Studies of the effect of 2,3-dioxoindolin (isatin) in comparison with serotonin on the isolated guinea pig ileum]. Fischer, W; Jordan, D; Müller, M, 1980)	0.52
"Dark liver pigmentation was observed in F344 rats in a subchronic toxicology study after daily dosing of LY368842 glycolate."	( Characterization of dark liver pigment observed in rats after subchronic dosing of the beta3-adrenergic receptor agonist LY368842. Abraham, TL; Ackermann, BL; Barbuch, RJ; He, MM; Jackson, DA; Jensen, CB; Lindsay, TJ; Wilke, AV, 2003)	0.32

Role	Description
EC 1.4.3.4 (monoamine oxidase) inhibitor	An EC 1.4.3.* (oxidoreductase acting on donor CH-NH2 group, oxygen as acceptor) inhibitor that interferes with the action of monoamine oxidase (EC 1.4.3.4).
plant metabolite	Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Class	Description
indoledione
[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
indole-3-acetate degradation	2	16

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
GLI family zinc finger 3	Homo sapiens (human)	Potency	18.1184	0.0007	14.5928	83.7951	AID1259369; AID1259392
nuclear receptor subfamily 1, group I, member 3	Homo sapiens (human)	Potency	40.1086	0.0010	22.6508	76.6163	AID1224838; AID1224839; AID1224893
estrogen-related nuclear receptor alpha	Homo sapiens (human)	Potency	13.5742	0.0015	30.6073	15,848.9004	AID1224841; AID1259401
aryl hydrocarbon receptor	Homo sapiens (human)	Potency	27.9789	0.0007	23.0674	1,258.9301	AID743085; AID743122
nuclear factor erythroid 2-related factor 2 isoform 1	Homo sapiens (human)	Potency	31.2573	0.0006	27.2152	1,122.0200	AID743202; AID743219
geminin	Homo sapiens (human)	Potency	20.5962	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)
Acetylcholinesterase	Electrophorus electricus (electric eel)	IC50 (µMol)	1,000.0000	0.0000	0.9453	9.9400	AID1896375
Coagulation factor XII	Homo sapiens (human)	Ki	100.0000	0.0025	1.8669	7.2500	AID1798240
Transthyretin	Homo sapiens (human)	IC50 (µMol)	50.0000	0.1600	4.2921	10.0000	AID448548
Cholinesterase	Homo sapiens (human)	Ki	100.0000	0.0000	1.5173	9.7300	AID1798240; AID281481
Liver carboxylesterase 1	Oryctolagus cuniculus (rabbit)	Ki	100.0000	0.0136	1.7025	7.2500	AID1798240
Amine oxidase [flavin-containing] B	Rattus norvegicus (Norway rat)	Ki	6.1250	0.0008	1.0927	6.0000	AID1796581
Amine oxidase [flavin-containing] A	Homo sapiens (human)	IC50 (µMol)	107.4824	0.0000	2.3789	9.7700	AID1602879; AID1896381; AID1917481; AID509549; AID528278; AID551122
Amine oxidase [flavin-containing] A	Homo sapiens (human)	Ki	9.8600	0.0019	2.3797	10.0000	AID1054594; AID1796581; AID352911; AID551122; AID612383
Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)	IC50 (µMol)	250.0000	0.0450	2.6742	8.0000	AID594815
Acetylcholinesterase	Homo sapiens (human)	Ki	100.0000	0.0000	1.2786	9.7300	AID1798240; AID281480
Liver carboxylesterase 1	Homo sapiens (human)	Ki	100.0000	0.0025	2.0136	8.4800	AID1798240; AID281478
Cruzipain	Trypanosoma cruzi	IC50 (µMol)	10.0000	0.0002	2.0450	8.0000	AID200223; AID213673
Amine oxidase [flavin-containing] B	Homo sapiens (human)	IC50 (µMol)	41.6612	0.0000	1.8914	9.5700	AID1140812; AID1301267; AID1602880; AID1896382; AID1917482; AID468865; AID497343; AID509550; AID514142; AID528279; AID551123; AID619468; AID693561; AID733502
Amine oxidase [flavin-containing] B	Homo sapiens (human)	Ki	4.0873	0.0006	1.7771	10.0000	AID1054591; AID1796581; AID254307; AID352912; AID551123; AID611924; AID612384
Amine oxidase [flavin-containing] B	Bos taurus (cattle)	Ki	6.1250	0.0540	1.8390	6.0000	AID1796581
Cholinesterase	Equus caballus (horse)	IC50 (µMol)	1,000.0000	0.0000	2.2214	9.4000	AID1896376
Secreted chorismate mutase	Mycobacterium tuberculosis H37Rv	IC50 (µMol)	1.0800	0.9900	1.2725	1.9600	AID1800202
Amine oxidase [flavin-containing] B	Mus musculus (house mouse)	Ki	6.1250	0.1000	2.3790	6.0000	AID1796581
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
plasma kallikrein-kinin cascade	Coagulation factor XII	Homo sapiens (human)
Factor XII activation	Coagulation factor XII	Homo sapiens (human)
blood coagulation, intrinsic pathway	Coagulation factor XII	Homo sapiens (human)
positive regulation of plasminogen activation	Coagulation factor XII	Homo sapiens (human)
protein processing	Coagulation factor XII	Homo sapiens (human)
protein autoprocessing	Coagulation factor XII	Homo sapiens (human)
positive regulation of blood coagulation	Coagulation factor XII	Homo sapiens (human)
zymogen activation	Coagulation factor XII	Homo sapiens (human)
fibrinolysis	Coagulation factor XII	Homo sapiens (human)
innate immune response	Coagulation factor XII	Homo sapiens (human)
response to misfolded protein	Coagulation factor XII	Homo sapiens (human)
positive regulation of fibrinolysis	Coagulation factor XII	Homo sapiens (human)
blood coagulation	Coagulation factor XII	Homo sapiens (human)
signal transduction	Transthyretin	Homo sapiens (human)
purine nucleobase metabolic process	Transthyretin	Homo sapiens (human)
xenobiotic metabolic process	Cholinesterase	Homo sapiens (human)
learning	Cholinesterase	Homo sapiens (human)
negative regulation of cell population proliferation	Cholinesterase	Homo sapiens (human)
neuroblast differentiation	Cholinesterase	Homo sapiens (human)
peptide hormone processing	Cholinesterase	Homo sapiens (human)
response to alkaloid	Cholinesterase	Homo sapiens (human)
cocaine metabolic process	Cholinesterase	Homo sapiens (human)
negative regulation of synaptic transmission	Cholinesterase	Homo sapiens (human)
response to glucocorticoid	Cholinesterase	Homo sapiens (human)
response to folic acid	Cholinesterase	Homo sapiens (human)
choline metabolic process	Cholinesterase	Homo sapiens (human)
acetylcholine catabolic process	Cholinesterase	Homo sapiens (human)
biogenic amine metabolic process	Amine oxidase [flavin-containing] A	Homo sapiens (human)
positive regulation of signal transduction	Amine oxidase [flavin-containing] A	Homo sapiens (human)
dopamine catabolic process	Amine oxidase [flavin-containing] A	Homo sapiens (human)
gene expression	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
dopamine secretion	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
chromatin remodeling	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
proteolysis	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathway	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
peptide cross-linking	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
protein deamination	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
negative regulation of endoplasmic reticulum calcium ion concentration	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
regulation of apoptotic process	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
positive regulation of apoptotic process	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
apoptotic cell clearance	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
positive regulation of GTPase activity	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
positive regulation of cell adhesion	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
positive regulation of neurogenesis	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
positive regulation of small GTPase mediated signal transduction	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
positive regulation of mitochondrial calcium ion concentration	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
bone development	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
branching involved in salivary gland morphogenesis	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
salivary gland cavitation	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
cellular response to cocaine	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
cellular response to dopamine	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
positive regulation of sprouting angiogenesis	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
cellular response to serotonin	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
regulation of apoptotic cell clearance	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
acetylcholine catabolic process in synaptic cleft	Acetylcholinesterase	Homo sapiens (human)
regulation of receptor recycling	Acetylcholinesterase	Homo sapiens (human)
osteoblast development	Acetylcholinesterase	Homo sapiens (human)
acetylcholine catabolic process	Acetylcholinesterase	Homo sapiens (human)
cell adhesion	Acetylcholinesterase	Homo sapiens (human)
nervous system development	Acetylcholinesterase	Homo sapiens (human)
synapse assembly	Acetylcholinesterase	Homo sapiens (human)
receptor internalization	Acetylcholinesterase	Homo sapiens (human)
negative regulation of synaptic transmission, cholinergic	Acetylcholinesterase	Homo sapiens (human)
amyloid precursor protein metabolic process	Acetylcholinesterase	Homo sapiens (human)
positive regulation of protein secretion	Acetylcholinesterase	Homo sapiens (human)
retina development in camera-type eye	Acetylcholinesterase	Homo sapiens (human)
acetylcholine receptor signaling pathway	Acetylcholinesterase	Homo sapiens (human)
positive regulation of cold-induced thermogenesis	Acetylcholinesterase	Homo sapiens (human)
cholesterol biosynthetic process	Liver carboxylesterase 1	Homo sapiens (human)
cholesterol metabolic process	Liver carboxylesterase 1	Homo sapiens (human)
response to toxic substance	Liver carboxylesterase 1	Homo sapiens (human)
positive regulation of cholesterol efflux	Liver carboxylesterase 1	Homo sapiens (human)
negative regulation of cholesterol storage	Liver carboxylesterase 1	Homo sapiens (human)
epithelial cell differentiation	Liver carboxylesterase 1	Homo sapiens (human)
cholesterol homeostasis	Liver carboxylesterase 1	Homo sapiens (human)
reverse cholesterol transport	Liver carboxylesterase 1	Homo sapiens (human)
medium-chain fatty acid metabolic process	Liver carboxylesterase 1	Homo sapiens (human)
regulation of bile acid biosynthetic process	Liver carboxylesterase 1	Homo sapiens (human)
cellular response to cholesterol	Liver carboxylesterase 1	Homo sapiens (human)
cellular response to low-density lipoprotein particle stimulus	Liver carboxylesterase 1	Homo sapiens (human)
cholesterol ester hydrolysis involved in cholesterol transport	Liver carboxylesterase 1	Homo sapiens (human)
positive regulation of cholesterol metabolic process	Liver carboxylesterase 1	Homo sapiens (human)
regulation of bile acid secretion	Liver carboxylesterase 1	Homo sapiens (human)
lipid catabolic process	Liver carboxylesterase 1	Homo sapiens (human)
response to xenobiotic stimulus	Amine oxidase [flavin-containing] B	Homo sapiens (human)
response to toxic substance	Amine oxidase [flavin-containing] B	Homo sapiens (human)
response to aluminum ion	Amine oxidase [flavin-containing] B	Homo sapiens (human)
response to selenium ion	Amine oxidase [flavin-containing] B	Homo sapiens (human)
negative regulation of serotonin secretion	Amine oxidase [flavin-containing] B	Homo sapiens (human)
phenylethylamine catabolic process	Amine oxidase [flavin-containing] B	Homo sapiens (human)
substantia nigra development	Amine oxidase [flavin-containing] B	Homo sapiens (human)
response to lipopolysaccharide	Amine oxidase [flavin-containing] B	Homo sapiens (human)
dopamine catabolic process	Amine oxidase [flavin-containing] B	Homo sapiens (human)
response to ethanol	Amine oxidase [flavin-containing] B	Homo sapiens (human)
positive regulation of dopamine metabolic process	Amine oxidase [flavin-containing] B	Homo sapiens (human)
hydrogen peroxide biosynthetic process	Amine oxidase [flavin-containing] B	Homo sapiens (human)
response to corticosterone	Amine oxidase [flavin-containing] B	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
serine-type endopeptidase activity	Coagulation factor XII	Homo sapiens (human)
calcium ion binding	Coagulation factor XII	Homo sapiens (human)
protein binding	Coagulation factor XII	Homo sapiens (human)
misfolded protein binding	Coagulation factor XII	Homo sapiens (human)
hormone activity	Transthyretin	Homo sapiens (human)
protein binding	Transthyretin	Homo sapiens (human)
identical protein binding	Transthyretin	Homo sapiens (human)
thyroid hormone binding	Transthyretin	Homo sapiens (human)
amyloid-beta binding	Cholinesterase	Homo sapiens (human)
catalytic activity	Cholinesterase	Homo sapiens (human)
acetylcholinesterase activity	Cholinesterase	Homo sapiens (human)
cholinesterase activity	Cholinesterase	Homo sapiens (human)
protein binding	Cholinesterase	Homo sapiens (human)
hydrolase activity, acting on ester bonds	Cholinesterase	Homo sapiens (human)
enzyme binding	Cholinesterase	Homo sapiens (human)
choline binding	Cholinesterase	Homo sapiens (human)
identical protein binding	Cholinesterase	Homo sapiens (human)
protein binding	Amine oxidase [flavin-containing] A	Homo sapiens (human)
primary amine oxidase activity	Amine oxidase [flavin-containing] A	Homo sapiens (human)
aliphatic amine oxidase activity	Amine oxidase [flavin-containing] A	Homo sapiens (human)
monoamine oxidase activity	Amine oxidase [flavin-containing] A	Homo sapiens (human)
flavin adenine dinucleotide binding	Amine oxidase [flavin-containing] A	Homo sapiens (human)
protein-glutamine gamma-glutamyltransferase activity	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
calcium ion binding	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
protein binding	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
GTP binding	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
peptidase activity	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
protein-glutamine glutaminase activity	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
histone serotonyltransferase activity	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
histone dopaminyltransferase activity	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
peptide noradrenalinyltransferase activity	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
peptide histaminyltransferase activity	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
amyloid-beta binding	Acetylcholinesterase	Homo sapiens (human)
acetylcholinesterase activity	Acetylcholinesterase	Homo sapiens (human)
cholinesterase activity	Acetylcholinesterase	Homo sapiens (human)
protein binding	Acetylcholinesterase	Homo sapiens (human)
collagen binding	Acetylcholinesterase	Homo sapiens (human)
hydrolase activity	Acetylcholinesterase	Homo sapiens (human)
serine hydrolase activity	Acetylcholinesterase	Homo sapiens (human)
acetylcholine binding	Acetylcholinesterase	Homo sapiens (human)
protein homodimerization activity	Acetylcholinesterase	Homo sapiens (human)
laminin binding	Acetylcholinesterase	Homo sapiens (human)
sterol esterase activity	Liver carboxylesterase 1	Homo sapiens (human)
methylumbelliferyl-acetate deacetylase activity	Liver carboxylesterase 1	Homo sapiens (human)
carboxylesterase activity	Liver carboxylesterase 1	Homo sapiens (human)
carboxylic ester hydrolase activity	Liver carboxylesterase 1	Homo sapiens (human)
protein binding	Amine oxidase [flavin-containing] B	Homo sapiens (human)
primary amine oxidase activity	Amine oxidase [flavin-containing] B	Homo sapiens (human)
electron transfer activity	Amine oxidase [flavin-containing] B	Homo sapiens (human)
identical protein binding	Amine oxidase [flavin-containing] B	Homo sapiens (human)
aliphatic amine oxidase activity	Amine oxidase [flavin-containing] B	Homo sapiens (human)
monoamine oxidase activity	Amine oxidase [flavin-containing] B	Homo sapiens (human)
flavin adenine dinucleotide binding	Amine oxidase [flavin-containing] B	Homo sapiens (human)
primary amine oxidase activity	Amine oxidase [flavin-containing] B	Bos taurus (cattle)
aliphatic amine oxidase activity	Amine oxidase [flavin-containing] B	Bos taurus (cattle)
monoamine oxidase activity	Amine oxidase [flavin-containing] B	Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
extracellular region	Coagulation factor XII	Homo sapiens (human)
extracellular space	Coagulation factor XII	Homo sapiens (human)
plasma membrane	Coagulation factor XII	Homo sapiens (human)
collagen-containing extracellular matrix	Coagulation factor XII	Homo sapiens (human)
extracellular exosome	Coagulation factor XII	Homo sapiens (human)
extracellular space	Coagulation factor XII	Homo sapiens (human)
rough endoplasmic reticulum	Coagulation factor XII	Homo sapiens (human)
extracellular region	Transthyretin	Homo sapiens (human)
extracellular space	Transthyretin	Homo sapiens (human)
azurophil granule lumen	Transthyretin	Homo sapiens (human)
extracellular exosome	Transthyretin	Homo sapiens (human)
extracellular space	Transthyretin	Homo sapiens (human)
extracellular region	Cholinesterase	Homo sapiens (human)
nuclear envelope lumen	Cholinesterase	Homo sapiens (human)
endoplasmic reticulum lumen	Cholinesterase	Homo sapiens (human)
blood microparticle	Cholinesterase	Homo sapiens (human)
plasma membrane	Cholinesterase	Homo sapiens (human)
extracellular space	Cholinesterase	Homo sapiens (human)
mitochondrion	Amine oxidase [flavin-containing] A	Homo sapiens (human)
mitochondrial outer membrane	Amine oxidase [flavin-containing] A	Homo sapiens (human)
cytosol	Amine oxidase [flavin-containing] A	Homo sapiens (human)
mitochondrion	Amine oxidase [flavin-containing] A	Homo sapiens (human)
collagen-containing extracellular matrix	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
nucleus	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
mitochondrion	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
endoplasmic reticulum	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
cytosol	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
plasma membrane	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
focal adhesion	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
extracellular matrix	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
perinuclear region of cytoplasm	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
collagen-containing extracellular matrix	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
extracellular exosome	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
chromatin	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
nucleosome	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
mitochondrion	Protein-glutamine gamma-glutamyltransferase 2	Homo sapiens (human)
extracellular region	Acetylcholinesterase	Homo sapiens (human)
basement membrane	Acetylcholinesterase	Homo sapiens (human)
extracellular space	Acetylcholinesterase	Homo sapiens (human)
nucleus	Acetylcholinesterase	Homo sapiens (human)
Golgi apparatus	Acetylcholinesterase	Homo sapiens (human)
plasma membrane	Acetylcholinesterase	Homo sapiens (human)
cell surface	Acetylcholinesterase	Homo sapiens (human)
membrane	Acetylcholinesterase	Homo sapiens (human)
neuromuscular junction	Acetylcholinesterase	Homo sapiens (human)
synaptic cleft	Acetylcholinesterase	Homo sapiens (human)
synapse	Acetylcholinesterase	Homo sapiens (human)
perinuclear region of cytoplasm	Acetylcholinesterase	Homo sapiens (human)
side of membrane	Acetylcholinesterase	Homo sapiens (human)
cytoplasm	Liver carboxylesterase 1	Homo sapiens (human)
endoplasmic reticulum	Liver carboxylesterase 1	Homo sapiens (human)
endoplasmic reticulum lumen	Liver carboxylesterase 1	Homo sapiens (human)
lipid droplet	Liver carboxylesterase 1	Homo sapiens (human)
cytosol	Liver carboxylesterase 1	Homo sapiens (human)
lipid droplet	Liver carboxylesterase 1	Homo sapiens (human)
endoplasmic reticulum	Liver carboxylesterase 1	Homo sapiens (human)
mitochondrion	Amine oxidase [flavin-containing] B	Homo sapiens (human)
mitochondrial envelope	Amine oxidase [flavin-containing] B	Homo sapiens (human)
mitochondrial outer membrane	Amine oxidase [flavin-containing] B	Homo sapiens (human)
dendrite	Amine oxidase [flavin-containing] B	Homo sapiens (human)
neuronal cell body	Amine oxidase [flavin-containing] B	Homo sapiens (human)
mitochondrion	Amine oxidase [flavin-containing] B	Homo sapiens (human)
mitochondrion	Amine oxidase [flavin-containing] B	Bos taurus (cattle)
mitochondrial outer membrane	Amine oxidase [flavin-containing] B	Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Assay ID	Title	Year	Journal	Article
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.
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.
AID1745845	Primary qHTS for Inhibitors of ATXN expression
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1798240	Enzyme Inhibition Assay from Article 10.1021/jm061471k: \\Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.\\	2007	Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8	Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
AID1796581	MAO Inhibition Assay from Article 10.1074/jbc.M500949200: \\Demonstration of isoleucine 199 as a structural determinant for the selective inhibition of human monoamine oxidase B by specific reversible inhibitors.\\	2005	The Journal of biological chemistry, Apr-22, Volume: 280, Issue:16	Demonstration of isoleucine 199 as a structural determinant for the selective inhibition of human monoamine oxidase B by specific reversible inhibitors.
AID1800202	CM Assay from Article 10.1111/cbdd.12265: \\Discovery and Structure Optimization of a Series of Isatin Derivatives as Mycobacterium tuberculosis Chorismate Mutase Inhibitors.\\	2014	Chemical biology & drug design, Apr, Volume: 83, Issue:4	Discovery and structure optimization of a series of isatin derivatives as Mycobacterium tuberculosis chorismate mutase inhibitors.
AID1602881	Selectivity index, ratio of IC50 for human recombinant MAO-A expressed in insect cells to IC50 for human recombinant MAO-B expressed in insect cells	2019	Bioorganic & medicinal chemistry letters, 04-15, Volume: 29, Issue:8	Design, synthesis and biological evaluation of novel human monoamine oxidase B inhibitors based on a fragment in an X-ray crystal structure.
AID1301267	Inhibition of human recombinant microsomal MAO-B expressed in baculovirus infected BTI-TN-5B1-4 cells using p-tyramine as substrate assessed as reduction in H2O2 production preincubated for 15 mins followed by substrate addition measured for 15 mins Ample	2016	European journal of medicinal chemistry, Jul-19, Volume: 117	(E)-3-Heteroarylidenechroman-4-ones as potent and selective monoamine oxidase-B inhibitors.
AID281481	Inhibition of human BChE	2007	Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8	Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
AID352914	Inhibition of human MAOB 1199A mutant	2009	Bioorganic & medicinal chemistry letters, May-01, Volume: 19, Issue:9	Inhibition of monoamine oxidase by (E)-styrylisatin analogues.
AID200223	Inhibitory activity against Trypanosoma brucei rhodesiense cysteine protease rhodesain	2003	Bioorganic & medicinal chemistry letters, Oct-20, Volume: 13, Issue:20	Synthesis and evaluation of isatins and thiosemicarbazone derivatives against cruzain, falcipain-2 and rhodesain.
AID610976	Irreversible inhibition of human MAOB expressed assessed as inhibition of p-tyramine oxidation to p-hydroxyphenyl-acetaldehyde at 25 uM measured after repeated washing by centrifugation-ultrafiltration method	2011	Journal of medicinal chemistry, Jul-28, Volume: 54, Issue:14	Chromone, a privileged scaffold for the development of monoamine oxidase inhibitors.
AID1055715	Antiproliferative activity against human AsPC1 cells after 48 hrs by SRB assay	2013	European journal of medicinal chemistry, , Volume: 70	Novel isatin-based hydroxamic acids as histone deacetylase inhibitors and antitumor agents.
AID497343	Inhibition of human MAOB by fluorimetry	2010	Bioorganic & medicinal chemistry, Aug-01, Volume: 18, Issue:15	Investigations on the 2-thiazolylhydrazyne scaffold: synthesis and molecular modeling of selective human monoamine oxidase inhibitors.
AID733495	Reversible inhibition of human MAO-B expressed in baculovirus infected BT1-TN-5B1-4 cells measured after repeated wash-out by centrifugation-ultrafiltration method	2013	European journal of medicinal chemistry, Jan, Volume: 59	1,5-Diphenylpenta-2,4-dien-1-ones as potent and selective monoamine oxidase-B inhibitors.
AID281477	Inhibition of human intestinal carboxylesterase expressed in sf21 cells	2007	Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8	Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
AID733502	Inhibition of recombinant human MAO-B expressed in baculovirus infected BT1-TN-5B1-4 cells assessed as inhibition of production of hydrogen peroxide from p-tyramine after 15 mins by Amplex Red assay	2013	European journal of medicinal chemistry, Jan, Volume: 59	1,5-Diphenylpenta-2,4-dien-1-ones as potent and selective monoamine oxidase-B inhibitors.
AID448548	Inhibition of TTR mediated fibrillogenesis assessed as acid-induced protein aggregation turbidity after 1.5 hrs by turbidimetric assay	2009	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17	Isatin derivatives, a novel class of transthyretin fibrillogenesis inhibitors.
AID1896375	Inhibition of electric eel AChE by Ellman's method	2022	Bioorganic & medicinal chemistry letters, Dec-01, Volume: 77	Selective butyrylcholinesterase inhibition by isatin dimers and 3-indolyl-3-hydroxy-2-oxindole dimers.
AID551122	Inhibition of human recombinant MAOA expressed in insect cells by fluorescence assay	2011	Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1	Inhibition of monoamine oxidase by selected C5- and C6-substituted isatin analogues.
AID509550	Inhibition of human recombinant MAOB expressed in baculovirus infected insect BTI-TN-5B1-4 cells assessed as production of hydrogen peroxide from p-tyramine by amplex red assay	2010	Journal of medicinal chemistry, Sep-09, Volume: 53, Issue:17	Synthesis, stereochemical separation, and biological evaluation of selective inhibitors of human MAO-B: 1-(4-arylthiazol-2-yl)-2-(3-methylcyclohexylidene)hydrazines.
AID733503	Inhibition of recombinant human MAO-A expressed in baculovirus infected BT1-TN-5B1-4 cells assessed as inhibition of production of hydrogen peroxide from p-tyramine at 100 uM after 15 mins by Amplex Red assay	2013	European journal of medicinal chemistry, Jan, Volume: 59	1,5-Diphenylpenta-2,4-dien-1-ones as potent and selective monoamine oxidase-B inhibitors.
AID1917481	Inhibition of human recombinant MAO-A assessed as inhibition of 4-hydroxyquinoline formation using kynuramine as substrate incubated for 20 mins by fluorescence spectrophotometry	2022	Bioorganic & medicinal chemistry, 11-01, Volume: 73	Isatoic anhydrides as novel inhibitors of monoamine oxidase.
AID1054589	Selectivity ratio of Ki for recombinant human MAO-A to Ki for recombinant human MAO-B	2013	European journal of medicinal chemistry, , Volume: 70	Novel polyamine analogues: from substrates towards potential inhibitors of monoamine oxidases.
AID448551	Displacement of [125I]thyroxin from TTR	2009	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17	Isatin derivatives, a novel class of transthyretin fibrillogenesis inhibitors.
AID497523	Inhibition of human MAOB at 50 uM	2010	Bioorganic & medicinal chemistry, Aug-01, Volume: 18, Issue:15	Investigations on the 2-thiazolylhydrazyne scaffold: synthesis and molecular modeling of selective human monoamine oxidase inhibitors.
AID1082383	Inhibition of Brassica rapa subsp. oleifera root growth at 10 mg/L	2011	Journal of agricultural and food chemistry, Sep-28, Volume: 59, Issue:18	Chemical synthesis, in vitro acetohydroxyacid synthase (AHAS) inhibition, herbicidal activity, and computational studies of isatin derivatives.
AID1819261	Binding affinity to Pseudomonas aeruginosa MurB assessed as change in melting temperature at 5 mM by differential scanning fluorimetry	2022	Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3	Discovery of Novel Inhibitors of Uridine Diphosphate-
AID72521	Inhibitory activity against Falcipain-2; No effect	2003	Bioorganic & medicinal chemistry letters, Oct-20, Volume: 13, Issue:20	Synthesis and evaluation of isatins and thiosemicarbazone derivatives against cruzain, falcipain-2 and rhodesain.
AID1602879	Inhibition of human recombinant MAO-A expressed in insect cells using p-tyramine as substrate preincubated for 30 mins followed by substrate addition measured for 15 mins by resorufin dye-based fluorescence assay	2019	Bioorganic & medicinal chemistry letters, 04-15, Volume: 29, Issue:8	Design, synthesis and biological evaluation of novel human monoamine oxidase B inhibitors based on a fragment in an X-ray crystal structure.
AID1896381	Inhibition of recombinant human MAO-A using using kynuramine as substrate assessed as inhibition of 4-hydroxyquinoline formation incubated for 20 mins by fluorescence spectrophotometric analysis	2022	Bioorganic & medicinal chemistry letters, Dec-01, Volume: 77	The inhibition of monoamine oxidase by 2H-1,4-benzothiazin-3(4H)-ones.
AID1176899	Reversible inhibition of human recombinant MAOA expressed in BTI-TN-5B1-4 cells assessed as AUF/t ratio at 35 uM by effective dilution method relative to untreated control	2015	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 25, Issue:3	Potent and selective MAO-B inhibitory activity: amino- versus nitro-3-arylcoumarin derivatives.
AID1430457	Antibacterial activity against Mycobacterium tuberculosis H37Rv after 7 days by microplate alamar blue assay	2017	Bioorganic & medicinal chemistry, 03-15, Volume: 25, Issue:6	Mycobacterium tuberculosis chorismate mutase: A potential target for TB.
AID1706700	Reversible inhibition of recombinant human MAO-B expressed in baculovirus infected BTI-TN-5B1-4 insect cells at 10 times IC50 using p-tyramine as substrate preincubated for 15 mins followed by 100 fold dilution and subsequent substrate addition and measur	2021	European journal of medicinal chemistry, Jan-01, Volume: 209	Pyrimido[1,2-b]indazole derivatives: Selective inhibitors of human monoamine oxidase B with neuroprotective activity.
AID1063516	Cytotoxicity against human HT-29 cells after 48 hrs by MTT assay	2014	Bioorganic & medicinal chemistry letters, Jan-15, Volume: 24, Issue:2	Design, synthesis and in vitro cytotoxicity evaluation of 5-(2-carboxyethenyl)isatin derivatives as anticancer agents.
AID1140814	Inhibition of human recombinant MAO-A expressed in baculovirus-infected BTI-TN-5B1-4 cell microsomes assessed as decrease in H2O2 production using p-tyramine as substrate at 100 uM preincubated for 15 mins by Amplex Red reagent based fluorimetric method	2014	Bioorganic & medicinal chemistry, May-15, Volume: 22, Issue:10	Identification of the stereochemical requirements in the 4-aryl-2-cycloalkylidenhydrazinylthiazole scaffold for the design of selective human monoamine oxidase B inhibitors.
AID693562	Selectivity ratio of IC50 for human MAO-A to IC50 for human MAO-B	2012	European journal of medicinal chemistry, Dec, Volume: 58	Recent advances in the development of selective human MAO-B inhibitors: (hetero)arylidene-(4-substituted-thiazol-2-yl)hydrazines.
AID1602878	Inhibition of human recombinant MAO-B expressed in insect cells at 1 uM using p-tyramine as substrate preincubated for 30 mins followed by substrate addition measured for 15 mins by resorufin dye-based fluorescence assay relative to control	2019	Bioorganic & medicinal chemistry letters, 04-15, Volume: 29, Issue:8	Design, synthesis and biological evaluation of novel human monoamine oxidase B inhibitors based on a fragment in an X-ray crystal structure.
AID469780	Reversible inhibition of human recombinant MAOB after washing with sodium phosphate buffer at 50 nM by centrifugation-ultrafiltration method	2010	European journal of medicinal chemistry, Feb, Volume: 45, Issue:2	Synthesis and inhibitory activity against human monoamine oxidase of N1-thiocarbamoyl-3,5-di(hetero)aryl-4,5-dihydro-(1H)-pyrazole derivatives.
AID652685	Cytotoxicity against human MDA-MB-231 cells after 48 hrs by MTT assay	2012	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 22, Issue:7	Iodine-catalyzed condensation of isatin with indoles: a facile synthesis of di(indolyl)indolin-2-ones and evaluation of their cytotoxicity.
AID551123	Inhibition of human recombinant MAOB expressed in insect cells by fluorescence assay	2011	Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1	Inhibition of monoamine oxidase by selected C5- and C6-substituted isatin analogues.
AID610980	Reversible inhibition of human MAOB expressed assessed as inhibition of p-tyramine oxidation to p-hydroxyphenyl-acetaldehyde at 20 uM measured before repeated washing by centrifugation-ultrafiltration method	2011	Journal of medicinal chemistry, Jul-28, Volume: 54, Issue:14	Chromone, a privileged scaffold for the development of monoamine oxidase inhibitors.
AID514143	Inhibition of human recombinant MAOA expressed in baculovirus infected BTI-TN-5B1-4 insect cells assessed as hydrogen peroxide production from p-tyramine at 100 uM by amplex red assay	2010	Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14	Synthesis, semipreparative HPLC separation, biological evaluation, and 3D-QSAR of hydrazothiazole derivatives as human monoamine oxidase B inhibitors.
AID448550	Inhibition of TTR mediated fibrillogenesis assessed as acid-induced protein aggregation turbidity at 40 mM after 1.5 hrs by turbidimetric assay relative to control	2009	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17	Isatin derivatives, a novel class of transthyretin fibrillogenesis inhibitors.
AID281480	Inhibition of human AChE	2007	Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8	Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
AID352913	Selectivity ratio of Ki for recombinant wild-type MAOA from human liver to Ki for recombinant wild-type MAOB from human liver	2009	Bioorganic & medicinal chemistry letters, May-01, Volume: 19, Issue:9	Inhibition of monoamine oxidase by (E)-styrylisatin analogues.
AID528279	Inhibition of human recombinant MAO-B expressed in baculovirus infected BT1 cells	2010	Bioorganic & medicinal chemistry letters, Nov-15, Volume: 20, Issue:22	Synthesis and molecular modelling studies of prenylated pyrazolines as MAO-B inhibitors.
AID497517	Selectivity index, ratio of IC50 for human recombinant MAOA to IC50 for human recombinant MAOB	2010	Bioorganic & medicinal chemistry, Aug-01, Volume: 18, Issue:15	Investigations on the 2-thiazolylhydrazyne scaffold: synthesis and molecular modeling of selective human monoamine oxidase inhibitors.
AID1054591	Competitive inhibition of recombinant human MAO-B expressed in baculovirus infected BT1 cells using benzylamine as substrate at 200 uM preincubated for 30 mins by Lineweaver-Burk plot analysis	2013	European journal of medicinal chemistry, , Volume: 70	Novel polyamine analogues: from substrates towards potential inhibitors of monoamine oxidases.
AID497520	Reversible inhibition of human MAOA at 100 uM by centrifugation-ultrafiltration method	2010	Bioorganic & medicinal chemistry, Aug-01, Volume: 18, Issue:15	Investigations on the 2-thiazolylhydrazyne scaffold: synthesis and molecular modeling of selective human monoamine oxidase inhibitors.
AID497344	Inhibition of human MAOA at 100 uM by fluorimetry	2010	Bioorganic & medicinal chemistry, Aug-01, Volume: 18, Issue:15	Investigations on the 2-thiazolylhydrazyne scaffold: synthesis and molecular modeling of selective human monoamine oxidase inhibitors.
AID281478	Inhibition of human liver CE1 expressed in sf21 cells	2007	Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8	Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
AID468864	Inhibition of human recombinant MAOA at 100 mM	2010	European journal of medicinal chemistry, Feb, Volume: 45, Issue:2	Synthesis and inhibitory activity against human monoamine oxidase of N1-thiocarbamoyl-3,5-di(hetero)aryl-4,5-dihydro-(1H)-pyrazole derivatives.
AID509549	Inhibition of human recombinant MAOA expressed in baculovirus infected insect BTI-TN-5B1-4 cells assessed as production of hydrogen peroxide from p-tyramine by amplex red assay	2010	Journal of medicinal chemistry, Sep-09, Volume: 53, Issue:17	Synthesis, stereochemical separation, and biological evaluation of selective inhibitors of human MAO-B: 1-(4-arylthiazol-2-yl)-2-(3-methylcyclohexylidene)hydrazines.
AID619468	Inhibition of human recombinant MAO-B expressed in baculovirus infected BTI-TN-5B1-4 cells assessed as production of hydrogen peroxide from p-tyramine after 15 mins by microplate fluorescence assay	2011	European journal of medicinal chemistry, Oct, Volume: 46, Issue:10	Synthesis and selective human monoamine oxidase inhibition of 3-carbonyl, 3-acyl, and 3-carboxyhydrazido coumarin derivatives.
AID619471	Selectivity ratio of IC50 for human recombinant MAO-A to IC50 for human recombinant MAO-B	2011	European journal of medicinal chemistry, Oct, Volume: 46, Issue:10	Synthesis and selective human monoamine oxidase inhibition of 3-carbonyl, 3-acyl, and 3-carboxyhydrazido coumarin derivatives.
AID1140813	Selectivity index, ratio of IC50 for human recombinant MAO-A expressed in baculovirus-infected BTI-TN-5B1-4 cell microsomes to IC50 for human recombinant MAO-B expressed in baculovirus-infected BTI-TN-5B1-4 cell microsomes	2014	Bioorganic & medicinal chemistry, May-15, Volume: 22, Issue:10	Identification of the stereochemical requirements in the 4-aryl-2-cycloalkylidenhydrazinylthiazole scaffold for the design of selective human monoamine oxidase B inhibitors.
AID1768350	Inhibition of recombinant human MAO-B expressed in baculovirus infected BTI cells assessed as inhibition of H2O2 production using kynuramine as substrate preincubated for 5 mins followed by substrate addition by Amplex Red reagent based fluorescence analy	2021	ACS medicinal chemistry letters, Jul-08, Volume: 12, Issue:7	Promising Non-cytotoxic Monosubstituted Chalcones to Target Monoamine Oxidase-B.
AID281479	Inhibition of rabbit liver carboxylesterase expressed in sf21 cells	2007	Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8	Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
AID594815	Inhibition of human transglutaminase 2 using Cbz-Gln-Gly as a substrate by GDH-coupled assay	2011	Bioorganic & medicinal chemistry letters, May-01, Volume: 21, Issue:9	Acylideneoxoindoles: a new class of reversible inhibitors of human transglutaminase 2.
AID1301268	Inhibition of human recombinant microsomal MAO-A expressed in baculovirus infected BTI-TN-5B1-4 cells using p-tyramine as substrate assessed as reduction in H2O2 production at 100 uM preincubated for 15 mins followed by substrate addition measured for 15	2016	European journal of medicinal chemistry, Jul-19, Volume: 117	(E)-3-Heteroarylidenechroman-4-ones as potent and selective monoamine oxidase-B inhibitors.
AID652688	Cytotoxicity against human MRC5 cells after 48 hrs by MTT assay	2012	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 22, Issue:7	Iodine-catalyzed condensation of isatin with indoles: a facile synthesis of di(indolyl)indolin-2-ones and evaluation of their cytotoxicity.
AID1389532	Inhibition of DAAO (unknown origin) at 20 uM	2018	Bioorganic & medicinal chemistry, 05-01, Volume: 26, Issue:8	Discovery of isatin and 1H-indazol-3-ol derivatives as d-amino acid oxidase (DAAO) inhibitors.
AID284490	Cytotoxicity against human U937 cells	2007	Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2	In vitro cytotoxicity evaluation of some substituted isatin derivatives.
AID1082888	Nematicidal activity against Meloidogyne incognita (root-knot nematode) juveniles J2 assessed as paralysis after 1 day	2012	Journal of agricultural and food chemistry, Aug-01, Volume: 60, Issue:30	Nematicidal activity of 2-thiophenecarboxaldehyde and methylisothiocyanate from caper (Capparis spinosa) against Meloidogyne incognita.
AID611924	Inhibition of MAO-B	2011	Journal of medicinal chemistry, Aug-11, Volume: 54, Issue:15	Tryptophan 2,3-dioxygenase (TDO) inhibitors. 3-(2-(pyridyl)ethenyl)indoles as potential anticancer immunomodulators.
AID1140812	Inhibition of human recombinant MAO-B expressed in baculovirus-infected BTI-TN-5B1-4 cell microsomes assessed as decrease in H2O2 production using p-tyramine as substrate preincubated for 15 mins by Amplex Red reagent based fluorimetric method	2014	Bioorganic & medicinal chemistry, May-15, Volume: 22, Issue:10	Identification of the stereochemical requirements in the 4-aryl-2-cycloalkylidenhydrazinylthiazole scaffold for the design of selective human monoamine oxidase B inhibitors.
AID352911	Inhibition of recombinant wild-type MAOA from human liver expressed in Pichia pastoris	2009	Bioorganic & medicinal chemistry letters, May-01, Volume: 19, Issue:9	Inhibition of monoamine oxidase by (E)-styrylisatin analogues.
AID1896376	Inhibition of equine serum BuChE by Ellman's method	2022	Bioorganic & medicinal chemistry letters, Dec-01, Volume: 77	Selective butyrylcholinesterase inhibition by isatin dimers and 3-indolyl-3-hydroxy-2-oxindole dimers.
AID1768351	Selectivity index, ratio of inhibition of recombinant human MAO-A to inhibition of recombinant human MAO-B	2021	ACS medicinal chemistry letters, Jul-08, Volume: 12, Issue:7	Promising Non-cytotoxic Monosubstituted Chalcones to Target Monoamine Oxidase-B.
AID733496	Reversible inhibition of human MAO-B expressed in baculovirus infected BT1-TN-5B1-4 cells by centrifugation-ultrafiltration method	2013	European journal of medicinal chemistry, Jan, Volume: 59	1,5-Diphenylpenta-2,4-dien-1-ones as potent and selective monoamine oxidase-B inhibitors.
AID509551	Selectivity ratio of IC50 for human recombinant MAOA to IC50 for human recombinant MAOB	2010	Journal of medicinal chemistry, Sep-09, Volume: 53, Issue:17	Synthesis, stereochemical separation, and biological evaluation of selective inhibitors of human MAO-B: 1-(4-arylthiazol-2-yl)-2-(3-methylcyclohexylidene)hydrazines.
AID350248	Cytotoxicity against human P-glycoprotein-expressing KBV1 cells after 72 hrs by MTT assay	2009	Journal of medicinal chemistry, May-28, Volume: 52, Issue:10	Synthesis, activity, and pharmacophore development for isatin-beta-thiosemicarbazones with selective activity toward multidrug-resistant cells.
AID1301270	Selectivity index, ratio of IC50 for human recombinant microsomal MAO-A expressed in baculovirus infected BTI-TN-5B1-4 cells to IC50 for human recombinant microsomal MAO-B expressed in baculovirus infected BTI-TN-5B1-4 cells	2016	European journal of medicinal chemistry, Jul-19, Volume: 117	(E)-3-Heteroarylidenechroman-4-ones as potent and selective monoamine oxidase-B inhibitors.
AID468868	Selectivity, ratio of IC50 for human recombinant MAOA to human recombinant MAOB	2010	European journal of medicinal chemistry, Feb, Volume: 45, Issue:2	Synthesis and inhibitory activity against human monoamine oxidase of N1-thiocarbamoyl-3,5-di(hetero)aryl-4,5-dihydro-(1H)-pyrazole derivatives.
AID612383	Inhibition of human MAOA	2011	Bioorganic & medicinal chemistry, Aug-15, Volume: 19, Issue:16	Inhibition of monoamine oxidase by C5-substituted phthalimide analogues.
AID1082384	Inhibition of Brassica rapa subsp. oleifera at 100 mg/L	2011	Journal of agricultural and food chemistry, Sep-28, Volume: 59, Issue:18	Chemical synthesis, in vitro acetohydroxyacid synthase (AHAS) inhibition, herbicidal activity, and computational studies of isatin derivatives.
AID1063518	Cytotoxicity against human K562 cells after 48 hrs by MTT assay	2014	Bioorganic & medicinal chemistry letters, Jan-15, Volume: 24, Issue:2	Design, synthesis and in vitro cytotoxicity evaluation of 5-(2-carboxyethenyl)isatin derivatives as anticancer agents.
AID213673	Inhibitory activity against the Trypanosoma cruzi cysteine protease cruzain	2003	Bioorganic & medicinal chemistry letters, Oct-20, Volume: 13, Issue:20	Synthesis and evaluation of isatins and thiosemicarbazone derivatives against cruzain, falcipain-2 and rhodesain.
AID1602880	Inhibition of human recombinant MAO-B expressed in insect cells using p-tyramine as substrate preincubated for 30 mins followed by substrate addition measured for 15 mins by resorufin dye-based fluorescence assay	2019	Bioorganic & medicinal chemistry letters, 04-15, Volume: 29, Issue:8	Design, synthesis and biological evaluation of novel human monoamine oxidase B inhibitors based on a fragment in an X-ray crystal structure.
AID619467	Inhibition of human recombinant MAO-A expressed in baculovirus infected BTI-TN-5B1-4 cells assessed as production of hydrogen peroxide from p-tyramine at 100 uM after 15 mins by microplate fluorescence assay	2011	European journal of medicinal chemistry, Oct, Volume: 46, Issue:10	Synthesis and selective human monoamine oxidase inhibition of 3-carbonyl, 3-acyl, and 3-carboxyhydrazido coumarin derivatives.
AID612384	Inhibition of human MAOB	2011	Bioorganic & medicinal chemistry, Aug-15, Volume: 19, Issue:16	Inhibition of monoamine oxidase by C5-substituted phthalimide analogues.
AID1063517	Cytotoxicity against human HepG2 cells after 48 hrs by MTT assay	2014	Bioorganic & medicinal chemistry letters, Jan-15, Volume: 24, Issue:2	Design, synthesis and in vitro cytotoxicity evaluation of 5-(2-carboxyethenyl)isatin derivatives as anticancer agents.
AID693561	Inhibition of human MAO-B expressed in baculovirus infected BTI-TN-5B1-4 cells using p-tyramine as substrate incubated for 15 mins prior to substrate addition measured for 15 mins by Amplex red assay	2012	European journal of medicinal chemistry, Dec, Volume: 58	Recent advances in the development of selective human MAO-B inhibitors: (hetero)arylidene-(4-substituted-thiazol-2-yl)hydrazines.
AID733499	Selectivity index, ratio of IC50 for recombinant human MAO-A expressed in baculovirus infected BT1-TN-5B1-4 cells to recombinant human MAO-B expressed in baculovirus infected BT1-TN-5B1-4 cells	2013	European journal of medicinal chemistry, Jan, Volume: 59	1,5-Diphenylpenta-2,4-dien-1-ones as potent and selective monoamine oxidase-B inhibitors.
AID1055717	Antiproliferative activity against human SW620 cells after 48 hrs by SRB assay	2013	European journal of medicinal chemistry, , Volume: 70	Novel isatin-based hydroxamic acids as histone deacetylase inhibitors and antitumor agents.
AID528278	Inhibition of human recombinant MAO-A expressed in baculovirus infected BT1 cells	2010	Bioorganic & medicinal chemistry letters, Nov-15, Volume: 20, Issue:22	Synthesis and molecular modelling studies of prenylated pyrazolines as MAO-B inhibitors.
AID693563	Inhibition of human MAO-A expressed in baculovirus infected BTI-TN-5B1-4 cells using p-tyramine as substrate at 100 uM incubated for 15 mins prior to substrate addition measured for 15 mins by Amplex red assay	2012	European journal of medicinal chemistry, Dec, Volume: 58	Recent advances in the development of selective human MAO-B inhibitors: (hetero)arylidene-(4-substituted-thiazol-2-yl)hydrazines.
AID1054594	Competitive inhibition of recombinant human MAO-A expressed in baculovirus infected BT1 cells using p-tyramine as substrate by Lineweaver-Burk plot analysis	2013	European journal of medicinal chemistry, , Volume: 70	Novel polyamine analogues: from substrates towards potential inhibitors of monoamine oxidases.
AID1055716	Antiproliferative activity against human MCF7 cells after 48 hrs by SRB assay	2013	European journal of medicinal chemistry, , Volume: 70	Novel isatin-based hydroxamic acids as histone deacetylase inhibitors and antitumor agents.
AID1768349	Inhibition of recombinant human MAO-A expressed in baculovirus infected BTI cells assessed as inhibition of H2O2 production using kynuramine as substrate preincubated for 5 mins followed by substrate addition by Amplex Red reagent based fluorescence analy	2021	ACS medicinal chemistry letters, Jul-08, Volume: 12, Issue:7	Promising Non-cytotoxic Monosubstituted Chalcones to Target Monoamine Oxidase-B.
AID1406678	Antiproliferative activity against human K562 cells after 48 hrs by MTT assay
AID1284106	Anticancer activity against human Jurkat cells after 48 hrs by MTT assay	2016	European journal of medicinal chemistry, Apr-13, Volume: 112	Synthesis and anti-cancer activity evaluation of 5-(2-carboxyethenyl)-isatin derivatives.
AID1416665	Reversible inhibition of recombinant human MAO-B expressed in baculovirus infected insect cells assessed as residual activity at 10 times IC50 pretreated for 30 mins followed by 100 fold compound dilution and p-tyramine substrate addition measured for 15	2017	MedChemComm, Sep-01, Volume: 8, Issue:9	MAO inhibitory activity of bromo-2-phenylbenzofurans: synthesis,
AID352912	Inhibition of recombinant wild-type MAOB from human liver expressed in Pichia pastoris	2009	Bioorganic & medicinal chemistry letters, May-01, Volume: 19, Issue:9	Inhibition of monoamine oxidase by (E)-styrylisatin analogues.
AID465619	Anticancer activity against human U937 cells by MTS assay	2010	European journal of medicinal chemistry, Mar, Volume: 45, Issue:3	QSAR study of isatin analogues as in vitro anti-cancer agents.
AID1082889	Nematicidal activity against Meloidogyne incognita (root-knot nematode) juveniles J2 assessed as paralysis after 1 hr	2012	Journal of agricultural and food chemistry, Aug-01, Volume: 60, Issue:30	Nematicidal activity of 2-thiophenecarboxaldehyde and methylisothiocyanate from caper (Capparis spinosa) against Meloidogyne incognita.
AID1917482	Inhibition of human recombinant MAO-B assessed as inhibition of 4-hydroxyquinoline formation using kynuramine as substrate incubated for 20 mins by fluorescence spectrophotometry	2022	Bioorganic & medicinal chemistry, 11-01, Volume: 73	Isatoic anhydrides as novel inhibitors of monoamine oxidase.
AID254307	Inhibition constant against human recombinant Monoamine oxidase-B	2005	Bioorganic & medicinal chemistry letters, Oct-15, Volume: 15, Issue:20	Docking studies on monoamine oxidase-B inhibitors: estimation of inhibition constants (K(i)) of a series of experimentally tested compounds.
AID474757	Antimicrobial activity against chloroquine-resistant Plasmodium falciparum W2	2010	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 20, Issue:7	Comparison of the antiplasmodial and falcipain-2 inhibitory activity of beta-amino alcohol thiolactone-chalcone and isatin-chalcone hybrids.
AID352910	Inhibition of baboon liver MAOB	2009	Bioorganic & medicinal chemistry letters, May-01, Volume: 19, Issue:9	Inhibition of monoamine oxidase by (E)-styrylisatin analogues.
AID514142	Inhibition of human recombinant MAOB expressed in baculovirus infected BTI-TN-5B1-4 insect cells assessed as hydrogen peroxide production from p-tyramine by amplex red assay	2010	Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14	Synthesis, semipreparative HPLC separation, biological evaluation, and 3D-QSAR of hydrazothiazole derivatives as human monoamine oxidase B inhibitors.
AID1082385	Inhibition of Arabidopsis thaliana AHAS at 100 mg/L colorimetric assay	2011	Journal of agricultural and food chemistry, Sep-28, Volume: 59, Issue:18	Chemical synthesis, in vitro acetohydroxyacid synthase (AHAS) inhibition, herbicidal activity, and computational studies of isatin derivatives.
AID497526	Inhibition of human MAOB at 50 uM by centrifugation-ultrafiltration method	2010	Bioorganic & medicinal chemistry, Aug-01, Volume: 18, Issue:15	Investigations on the 2-thiazolylhydrazyne scaffold: synthesis and molecular modeling of selective human monoamine oxidase inhibitors.
AID1378859	Reversible inhibition of human recombinant MAO-B expressed in baculovirus infected BTI-TN5B1-4 cells using p-tyramine as substrate assessed as recovery of enzyme activity at 10 fold IC50 preincubated for 30 mins followed by 100 fold dilution and substrate	2017	European journal of medicinal chemistry, Oct-20, Volume: 139	Synthesis and structure-activity relationship study of novel 3-heteroarylcoumarins based on pyridazine scaffold as selective MAO-B inhibitors.
AID350249	Cytotoxicity against human P-gp-negative KB-3-1 cells after 72 hrs by MTT assay	2009	Journal of medicinal chemistry, May-28, Volume: 52, Issue:10	Synthesis, activity, and pharmacophore development for isatin-beta-thiosemicarbazones with selective activity toward multidrug-resistant cells.
AID652686	Cytotoxicity against human SK-N-SH cells after 48 hrs by MTT assay	2012	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 22, Issue:7	Iodine-catalyzed condensation of isatin with indoles: a facile synthesis of di(indolyl)indolin-2-ones and evaluation of their cytotoxicity.
AID652687	Cytotoxicity against human A549 cells after 48 hrs by MTT assay	2012	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 22, Issue:7	Iodine-catalyzed condensation of isatin with indoles: a facile synthesis of di(indolyl)indolin-2-ones and evaluation of their cytotoxicity.
AID497340	Inhibition of human MAOA at 100 nM	2010	Bioorganic & medicinal chemistry, Aug-01, Volume: 18, Issue:15	Investigations on the 2-thiazolylhydrazyne scaffold: synthesis and molecular modeling of selective human monoamine oxidase inhibitors.
AID1406679	Antiproliferative activity against human HepG2 cells after 48 hrs by MTT assay
AID514145	Selectivity ratio of IC50 for human recombinant MAOA to IC50 for human recombinant MAOB	2010	Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14	Synthesis, semipreparative HPLC separation, biological evaluation, and 3D-QSAR of hydrazothiazole derivatives as human monoamine oxidase B inhibitors.
AID474758	Inhibition of recombinant Plasmodium falciparum falcipain-2	2010	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 20, Issue:7	Comparison of the antiplasmodial and falcipain-2 inhibitory activity of beta-amino alcohol thiolactone-chalcone and isatin-chalcone hybrids.
AID1055714	Antiproliferative activity against human PC3 cells after 48 hrs by SRB assay	2013	European journal of medicinal chemistry, , Volume: 70	Novel isatin-based hydroxamic acids as histone deacetylase inhibitors and antitumor agents.
AID1819260	Binding affinity to Pseudomonas aeruginosa MurB assessed as change in melting temperature at 1 mM by differential scanning fluorimetry	2022	Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3	Discovery of Novel Inhibitors of Uridine Diphosphate-
AID1896382	Inhibition of recombinant human MAO-B using using kynuramine as substrate assessed as inhibition of 4-hydroxyquinoline formation incubated for 20 mins by fluorescence spectrophotometric analysis	2022	Bioorganic & medicinal chemistry letters, Dec-01, Volume: 77	The inhibition of monoamine oxidase by 2H-1,4-benzothiazin-3(4H)-ones.
AID578272	Cytotoxicity against human U937 cells	2011	Bioorganic & medicinal chemistry, Mar-01, Volume: 19, Issue:5	Synthesis and hydrolytic evaluation of acid-labile imine-linked cytotoxic isatin model systems.
AID468870	Reversible inhibition of human recombinant MAOB before washing with sodium phosphate buffer at 50 nM by centrifugation-ultrafiltration method	2010	European journal of medicinal chemistry, Feb, Volume: 45, Issue:2	Synthesis and inhibitory activity against human monoamine oxidase of N1-thiocarbamoyl-3,5-di(hetero)aryl-4,5-dihydro-(1H)-pyrazole derivatives.
AID551124	Selectivity ratio of Ki for human recombinant MAOA to Ki for human recombinant MAOB	2011	Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1	Inhibition of monoamine oxidase by selected C5- and C6-substituted isatin analogues.
AID1055713	Antiproliferative activity against human NCI-H460 cells after 48 hrs by SRB assay	2013	European journal of medicinal chemistry, , Volume: 70	Novel isatin-based hydroxamic acids as histone deacetylase inhibitors and antitumor agents.
AID468865	Inhibition of human recombinant MAOB	2010	European journal of medicinal chemistry, Feb, Volume: 45, Issue:2	Synthesis and inhibitory activity against human monoamine oxidase of N1-thiocarbamoyl-3,5-di(hetero)aryl-4,5-dihydro-(1H)-pyrazole derivatives.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	146 (14.11)	18.7374
1990's	92 (8.89)	18.2507
2000's	185 (17.87)	29.6817
2010's	435 (42.03)	24.3611
2020's	177 (17.10)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	3 (0.27%)	5.53%
Reviews	51 (4.67%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	1,039 (95.06%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
keto-pantoyllactone [no description available]	1.97	1	tetrahydrofurandione
gamma-aminobutyric acid gamma-Aminobutyric Acid: The most common inhibitory neurotransmitter in the central nervous system.. gamma-aminobutyric acid : A gamma-amino acid that is butanoic acid with the amino substituent located at C-4.	2.4	2	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
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	1	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
acetaldehyde Acetaldehyde: A colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis.. acetaldehyde : The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.. aldehyde : A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.. acetyl group : A group, formally derived from acetic acid by dehydroxylation, which is fundamental to the biochemistry of all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.	7.05	1	aldehyde	carcinogenic agent; EC 3.5.1.4 (amidase) inhibitor; electron acceptor; Escherichia coli metabolite; human metabolite; mouse metabolite; mutagen; oxidising agent; Saccharomyces cerevisiae metabolite; teratogenic agent
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	2.68	3	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
agmatine Agmatine: Decarboxylated arginine, isolated from several plant and animal sources, e.g., pollen, ergot, herring sperm, octopus muscle.	2	1	guanidines; primary amino compound	Escherichia coli metabolite; mouse metabolite
anthranilic acid anthranilic acid: RN given refers to parent cpd; structure in Negwer, 5th ed, #565. anthranilic acid : An aminobenzoic acid that is benzoic acid having a single amino substituent located at position 2. It is a metabolite produced in L-tryptophan-kynurenine pathway in the central nervous system.	7.58	2	aminobenzoic acid	human metabolite; mouse metabolite
benzaldehyde [no description available]	2.08	1	benzaldehydes	EC 3.1.1.3 (triacylglycerol lipase) inhibitor; EC 3.5.5.1 (nitrilase) inhibitor; flavouring agent; fragrance; odorant receptor agonist; plant metabolite
betaine glycine betaine : The amino acid betaine derived from glycine.	2.51	2	amino-acid betaine; glycine derivative	fundamental metabolite
bromide Bromides: Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	2.05	1	halide anion; monoatomic bromine
carbamates [no description available]	2.04	1	amino-acid anion
carnitine [no description available]	1.96	1	amino-acid betaine	human metabolite; mouse 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).	9.12	14	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
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.	2.08	1	chlorine molecular entity; gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
coumarin 2H-chromen-2-one: coumarin derivative	2.88	3	coumarins	fluorescent dye; human metabolite; plant metabolite
salicylic acid Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).	2.11	1	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
4-nitrophenylphosphate nitrophenylphosphate: RN given refers to mono(4-nitrophenyl) ester of phosphoric acid. 4-nitrophenyl phosphate : An aryl phosphate resulting from the mono-esterification of phosphoric acid with 4-nitrophenol.	1.97	1	aryl phosphate	mouse metabolite
methylmalonic acid Methylmalonic Acid: A malonic acid derivative which is a vital intermediate in the metabolism of fat and protein. Abnormalities in methylmalonic acid metabolism lead to methylmalonic aciduria. This metabolic disease is attributed to a block in the enzymatic conversion of methylmalonyl CoA to succinyl CoA.. methylmalonic acid : A dicarboxylic acid that is malonic acid in which one of the methylene hydrogens is substituted by a methyl group.	2.13	1	C4-dicarboxylic acid	human metabolite
3,4-dihydroxyphenylacetic acid 3,4-Dihydroxyphenylacetic Acid: A deaminated metabolite of LEVODOPA.. (3,4-dihydroxyphenyl)acetic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine.. dihydroxyphenylacetic acid : A dihydroxy monocarboxylic acid consisting of phenylacetic acid having two phenolic hydroxy substituents.	2.58	2	catechols; dihydroxyphenylacetic acid	human metabolite
creatine [no description available]	1.94	1	glycine derivative; guanidines; zwitterion	geroprotector; human metabolite; mouse metabolite; neuroprotective agent; nutraceutical
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	2.05	1	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
diacetyl butane-2,3-dione : An alpha-diketone that is butane substituted by oxo groups at positions 2 and 3. It is a metabolite produced during the malolactic fermentation.	6.93	1	alpha-diketone	Escherichia coli metabolite; Saccharomyces cerevisiae metabolite
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	2.51	2	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
formaldehyde paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy	8.11	5	aldehyde; one-carbon compound	allergen; carcinogenic agent; disinfectant; EC 3.5.1.4 (amidase) inhibitor; environmental contaminant; Escherichia coli metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
glycine [no description available]	2.35	2	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
glyoxylic acid glyoxylic acid: RN given refers to parent cpd. glyoxylic acid : A 2-oxo monocarboxylic acid that is acetic acid bearing an oxo group at the alpha carbon atom.	2.41	1	2-oxo monocarboxylic acid; aldehydic acid	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
histamine [no description available]	2.65	3	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.	2.74	3	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
hydroquinone [no description available]	2.31	1	benzenediol; hydroquinones	antioxidant; carcinogenic agent; cofactor; Escherichia coli metabolite; human xenobiotic metabolite; mouse metabolite; skin lightening agent
indole [no description available]	5.19	15	indole; polycyclic heteroarene	Escherichia coli metabolite
indoleacetic acid indoleacetic acid: RN given refers to unlabeled parent cpd; structure in Merck Index, 9th ed, #4841. auxin : Any of a group of compounds, both naturally occurring and synthetic, that induce cell elongation in plant stems (from Greek alphaupsilonxialphanuomega, "to grow").. indole-3-acetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.	1.98	1	indole-3-acetic acids; monocarboxylic acid	auxin; human metabolite; mouse metabolite; plant hormone; plant metabolite
iodine Iodine: A nonmetallic element of the halogen group that is represented by the atomic symbol I, atomic number 53, and atomic weight of 126.90. It is a nutritionally essential element, especially important in thyroid hormone synthesis. In solution, it has anti-infective properties and is used topically.. diiodine : Molecule comprising two covalently bonded iodine atoms with overall zero charge..	3.44	7	diatomic iodine	nutrient
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	7.42	2	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
melatonin [no description available]	2.9	4	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
n-acetylserotonin N-acetylserotonin : An N-acylserotonin resulting from the formal condensation of the primary amino group of serotonin with the carboxy group of acetic acid.	2.38	2	acetamides; N-acylserotonin; phenols	antioxidant; human metabolite; mouse metabolite; tropomyosin-related kinase B receptor agonist
naphthalene [no description available]	2.08	1	naphthalenes; ortho-fused bicyclic arene	apoptosis inhibitor; carcinogenic agent; environmental contaminant; mouse metabolite; plant metabolite; volatile oil component
nickel Nickel: A trace element with the atomic symbol Ni, atomic number 28, and atomic weight 58.69. It is a cofactor of the enzyme UREASE.. nickel ion : A nickel atom having a net electric charge.. nickel atom : Chemical element (nickel group element atom) with atomic number 28.	3.31	6	metal allergen; nickel group element atom	epitope; micronutrient
nitrites Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)	2.15	1	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
phenylacetic acid phenylacetic acid : A monocarboxylic acid that is toluene in which one of the hydrogens of the methyl group has been replaced by a carboxy group.	2.41	1	benzenes; monocarboxylic acid; phenylacetic acids	allergen; Aspergillus metabolite; auxin; EC 6.4.1.1 (pyruvate carboxylase) inhibitor; Escherichia coli metabolite; human metabolite; plant growth retardant; plant metabolite; Saccharomyces cerevisiae metabolite; toxin
phosphoric acid phosphoric acid: concise etchant is 37% H3PO4. phosphoric acid : A phosphorus oxoacid that consists of one oxo and three hydroxy groups joined covalently to a central phosphorus atom.	7.85	3	phosphoric acids	algal metabolite; fertilizer; human metabolite; NMR chemical shift reference compound; solvent
pyrazole 1H-pyrazole : The 1H-tautomer of pyrazole.	7.11	1	pyrazole
pyridine azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.	3.06	4	azaarene; mancude organic heteromonocyclic parent; monocyclic heteroarene; pyridines	environmental contaminant; NMR chemical shift reference compound
pyridoxal phosphate Pyridoxal Phosphate: This is the active form of VITAMIN B 6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (PYRIDOXAMINE).. pyridoxal 5'-phosphate : The monophosphate ester obtained by condensation of phosphoric acid with the primary hydroxy group of pyridoxal.	2.4	2	methylpyridines; monohydroxypyridine; pyridinecarbaldehyde; vitamin B6 phosphate	coenzyme; cofactor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; 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.	2.08	1	2-oxo monocarboxylic acid	cofactor; fundamental metabolite
sarcosine cocobetaine: N-alkyl-betaine; cause of shampoo dermatitis	2.02	1	N-alkylglycine zwitterion; N-alkylglycine; N-methyl-amino acid; N-methylglycines	Escherichia coli metabolite; glycine receptor agonist; glycine transporter 1 inhibitor; human metabolite; mouse metabolite
spermine [no description available]	2.08	1	polyazaalkane; tetramine	antioxidant; fundamental metabolite; immunosuppressive agent
tryptamine [no description available]	2.89	4	aminoalkylindole; aralkylamino compound; indole alkaloid; tryptamines	human metabolite; mouse metabolite; plant metabolite
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	2.92	4	pyrimidine nucleobase; pyrimidone	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; prodrug; Saccharomyces cerevisiae 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.	4.4	6	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.	1.99	1	xanthine	Saccharomyces cerevisiae metabolite
8-hydroxy-2-(di-n-propylamino)tetralin 8-Hydroxy-2-(di-n-propylamino)tetralin: A serotonin 1A-receptor agonist that is used experimentally to test the effects of serotonin.. 8-OH-DPAT : A tetralin substituted at positions 1 and 7 by hydroxy and dipropylamino groups respectively	2.06	1	phenols; tertiary amino compound; tetralins	serotonergic antagonist
4-iodo-2,5-dimethoxyphenylisopropylamine 4-iodo-2,5-dimethoxyphenylisopropylamine: RN given refers to unlabeled parent cpd without isomeric designation; a serotonin agonist. 2-(4-iodo-2,5-dimethoxyphenyl)-1-methylethylamine : An organoiodine compound that is amphetamine bearing two methoxy substituents at positions 2 and 5 as well as an iodo substituent at position 4.	2.06	1	amphetamines; dimethoxybenzene; organoiodine compound
1-(3-chlorophenyl)piperazine 1-(3-chlorophenyl)piperazine: supposed metabolite of TRAZODONE; RN given refers to parent cpd; structure. 1-(3-chlorophenyl)piperazine : A N-arylpiperazine that is piperazine carrying a 3-chlorophenyl substituent at position 1. It is a metabolite of the antidepressant drug trazodone.	2	1	monochlorobenzenes; N-arylpiperazine	drug metabolite; environmental contaminant; serotonergic agonist; xenobiotic
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine: A dopaminergic neurotoxic compound which produces irreversible clinical, chemical, and pathological alterations that mimic those found in Parkinson disease.. 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine : A tetrahydropyridine that is 1,2,3,6-tetrahydropyridine substituted by a methyl group at position 1 and a phenyl group at position 4.	2.98	4	methylpyridines; phenylpyridine; tetrahydropyridine	neurotoxin
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.	2.36	2	alkanethiol; primary alcohol	geroprotector
ro 5-4864 4'-chlorodiazepam: selectively binds peripheral benzodiazepine receptor	1.97	1
homovanillic acid Homovanillic Acid: A 3-O-methyl ETHER of (3,4-dihydroxyphenyl)acetic acid.. homovanillate : A hydroxy monocarboxylic acid anion which is obtained by deprotonation of the carboxy group of homovanillic acid.. homovanillic acid : A monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite.	2.25	1	guaiacols; monocarboxylic acid	human metabolite; mouse metabolite
5,5-dimethyl-1-pyrroline-1-oxide 5,5-dimethyl-1-pyrroline-1-oxide: do not confuse with DMPO (4',5'-dihydroxy-7-methoxy-4-phenyl-5,2'-oxidocoumarin). 5,5-dimethyl-1-pyrroline N-oxide : A member of the class of 1-pyrroline nitrones (1-pyrroline N-oxides) resulting from the formal N-oxidation of 5,5-dimethyl-1-pyrroline. Used as a spin trap for the study of radicals formed by enzymatic acetaldehyde oxidation.	1.99	1	1-pyrroline nitrones	neuroprotective agent; spin trapping reagent
phenytoin [no description available]	2.06	1	imidazolidine-2,4-dione	anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent
hydroxyindoleacetic acid (5-hydroxyindol-3-yl)acetic acid : A member of the class of indole-3-acetic acids that is indole-3-acetic acid substituted by a hydroxy group at C-5.	3.07	5	indole-3-acetic acids	drug metabolite; human metabolite; mouse metabolite
tacrine Tacrine: A cholinesterase inhibitor that crosses the blood-brain barrier. Tacrine has been used to counter the effects of muscle relaxants, as a respiratory stimulant, and in the treatment of Alzheimer's disease and other central nervous system disorders.. tacrine : A member of the class of acridines that is 1,2,3,4-tetrahydroacridine substituted by an amino group at position 9. It is used in the treatment of Alzheimer's disease.	8.01	3	acridines; aromatic amine	EC 3.1.1.7 (acetylcholinesterase) inhibitor
2,2'-azobis(2-amidinopropane) 2,2'-azobis(2-amidinopropane): water-soluble free-radical initiator	2.06	1	monoazo compound
acetazolamide Acetazolamide: One of the CARBONIC ANHYDRASE INHIBITORS that is sometimes effective against absence seizures. It is sometimes useful also as an adjunct in the treatment of tonic-clonic, myoclonic, and atonic seizures, particularly in women whose seizures occur or are exacerbated at specific times in the menstrual cycle. However, its usefulness is transient often because of rapid development of tolerance. Its antiepileptic effect may be due to its inhibitory effect on brain carbonic anhydrase, which leads to an increased transneuronal chloride gradient, increased chloride current, and increased inhibition. (From Smith and Reynard, Textbook of Pharmacology, 1991, p337)	3.41	1	monocarboxylic acid amide; sulfonamide; thiadiazoles	anticonvulsant; diuretic; EC 4.2.1.1 (carbonic anhydrase) inhibitor
alpha-methylserotonin alpha-methylserotonin: potent agonist at M & D receptors of serotonin; RN given refers to parent cpd	2.01	1	tryptamines	serotonergic agonist
theophylline [no description available]	2.37	2	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
aspirin Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.	2.11	1	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
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.	2.06	1	ethanolamines; monocarboxylic acid amide; propanolamine	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; sympatholytic agent; xenobiotic
azobenzene azobenzene: photosensor molecule known to undergo reversible isomerization from trans to cis on illumination with photons of appropriate wavelength; RN given refers to cpd without isomeric designation; structure. (E)-azobenzene : The (E)-isomer of azobenzene.. (Z)-azobenzene : The (Z)-isomer of azobenzene.. azobenzene : A molecule whose structure comprises two phenyl rings linked by a N=N double bond; the parent compound of the azobenzene class of compounds.	2.05	1	azobenzenes
bisacodyl Bisacodyl: A diphenylmethane stimulant laxative used for the treatment of CONSTIPATION and for bowel evacuation. (From Martindale, The Extra Pharmacopoeia, 30th ed, p871)	6.95	1	diarylmethane
bisindolylmaleimide i bisindolylmaleimide I: a bis(indolyl)maleimide	2.06	1
bu 224 BU 224: a selective imidazoline 2-receptor blocker	2	1	quinolines
caffeine [no description available]	2.05	1	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.	2.06	1	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.	2.77	3	aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug
ciprofloxacin Ciprofloxacin: A broad-spectrum antimicrobial carboxyfluoroquinoline.. ciprofloxacin : A quinolone that is quinolin-4(1H)-one bearing cyclopropyl, carboxylic acid, fluoro and piperazin-1-yl substituents at positions 1, 3, 6 and 7, respectively.	7.06	1	aminoquinoline; cyclopropanes; fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone; zwitterion	antibacterial drug; antiinfective agent; antimicrobial agent; DNA synthesis inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; environmental contaminant; topoisomerase IV inhibitor; xenobiotic
clonazepam Clonazepam: An anticonvulsant used for several types of seizures, including myotonic or atonic seizures, photosensitive epilepsy, and absence seizures, although tolerance may develop. It is seldom effective in generalized tonic-clonic or partial seizures. The mechanism of action appears to involve the enhancement of GAMMA-AMINOBUTYRIC ACID receptor responses.. clonazepam : 1,3-Dihydro-2H-1,4-benzodiazepin-2-one in which the hydrogens at positions 5 and 7 are substituted by 2-chlorophenyl and nitro groups, respectively. It is used in the treatment of all types of epilepsy and seizures, as well as myoclonus and associated abnormal movements, and panic disorders. However, its use can be limited by the development of tolerance and by sedation.	1.96	1	1,4-benzodiazepinone; monochlorobenzenes	anticonvulsant; anxiolytic drug; GABA modulator
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.	8.24	6	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; xenobiotic
dipyridamole Dipyridamole: A phosphodiesterase inhibitor that blocks uptake and metabolism of adenosine by erythrocytes and vascular endothelial cells. Dipyridamole also potentiates the antiaggregating action of prostacyclin. (From AMA Drug Evaluations Annual, 1994, p752). dipyridamole : A pyrimidopyrimidine that is 2,2',2'',2'''-(pyrimido[5,4-d]pyrimidine-2,6-diyldinitrilo)tetraethanol substituted by piperidin-1-yl groups at positions 4 and 8 respectively. A vasodilator agent, it inhibits the formation of blood clots.	2.36	2	piperidines; pyrimidopyrimidine; tertiary amino compound; tetrol	adenosine phosphodiesterase inhibitor; EC 3.5.4.4 (adenosine deaminase) inhibitor; platelet aggregation inhibitor; vasodilator agent
valproic acid Valproic Acid: A fatty acid with anticonvulsant and anti-manic properties that is used in the treatment of EPILEPSY and BIPOLAR DISORDER. The mechanisms of its therapeutic actions are not well understood. It may act by increasing GAMMA-AMINOBUTYRIC ACID levels in the brain or by altering the properties of VOLTAGE-GATED SODIUM CHANNELS.. valproic acid : A branched-chain saturated fatty acid that comprises of a propyl substituent on a pentanoic acid stem.	2.11	1	branched-chain fatty acid; branched-chain saturated fatty acid	anticonvulsant; antimanic drug; EC 3.5.1.98 (histone deacetylase) inhibitor; GABA agent; neuroprotective agent; psychotropic drug; teratogenic agent
racemetirosine alpha-Methyltyrosine: An inhibitor of the enzyme TYROSINE 3-MONOOXYGENASE, and consequently of the synthesis of catecholamines. It is used to control the symptoms of excessive sympathetic stimulation in patients with PHEOCHROMOCYTOMA. (Martindale, The Extra Pharmacopoeia, 30th ed)	2.41	2
ether Ether: A mobile, very volatile, highly flammable liquid used as an inhalation anesthetic and as a solvent for waxes, fats, oils, perfumes, alkaloids, and gums. It is mildly irritating to skin and mucous membranes.. ether : An organooxygen compound with formula ROR, where R is not hydrogen.. diethyl ether : An ether in which the oxygen atom is linked to two ethyl groups.	1.98	1	ether; volatile organic compound	inhalation anaesthetic; non-polar solvent; refrigerant
ethylenediamine ethylenediamine: RN given refers to parent cpd; edamine is the recommended contraction for the ethylenediamine radical. ethylenediamine : An alkane-alpha,omega-diamine in which the alkane is ethane.	2.05	1	alkane-alpha,omega-diamine	GABA agonist
flumazenil Flumazenil: A potent benzodiazepine receptor antagonist. Since it reverses the sedative and other actions of benzodiazepines, it has been suggested as an antidote to benzodiazepine overdoses.. flumazenil : An organic heterotricyclic compound that is 5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine which is substituted at positions 3, 5, 6, and 8 by ethoxycarbonyl, methyl, oxo, and fluoro groups, respectively. It is used as an antidote to benzodiazepine overdose.	1.99	1	ethyl ester; imidazobenzodiazepine; organofluorine compound	antidote to benzodiazepine poisoning; GABA antagonist
flunitrazepam Flunitrazepam: A benzodiazepine with pharmacologic actions similar to those of DIAZEPAM that can cause ANTEROGRADE AMNESIA. Some reports indicate that it is used as a date rape drug and suggest that it may precipitate violent behavior. The United States Government has banned the importation of this drug.. flunitrazepam : A 1,4-benzodiazepinone that is nitrazepam substituted by a methyl group at position 1 and by a fluoro group at position 2'. It is a potent hypnotic, sedative, and amnestic drug used to treat chronic insomnia.	1.97	1	1,4-benzodiazepinone; C-nitro compound; monofluorobenzenes	anxiolytic drug; GABAA receptor agonist; sedative
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.	2.59	2	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
gaboxadol gaboxadol: GABA agonist; inhibitor of GABA uptake systems; structure	2.17	1	oxazole
glyburide Glyburide: An antidiabetic sulfonylurea derivative with actions like those of chlorpropamide. glyburide : An N-sulfonylurea that is acetohexamide in which the acetyl group is replaced by a 2-(5-chloro-2-methoxybenzamido)ethyl group.	2.06	1	monochlorobenzenes; N-sulfonylurea	anti-arrhythmia drug; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor; hypoglycemic agent
guanethidine Guanethidine: An antihypertensive agent that acts by inhibiting selectively transmission in post-ganglionic adrenergic nerves. It is believed to act mainly by preventing the release of norepinephrine at nerve endings and causes depletion of norepinephrine in peripheral sympathetic nerve terminals as well as in tissues.. guanethidine : A member of the class of guanidines in which one of the hydrogens of the amino group has been replaced by a 2-azocan-1-ylethyl group.. guanethidine sulfate : A organic sulfate salt composed of two molecules of guanethidine and one of sulfuric acid.	1.99	1	azocanes; guanidines	adrenergic antagonist; antihypertensive agent; sympatholytic agent
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.	7.38	2	carboxamidine; guanidines; one-carbon compound
harmaline Harmaline: A beta-carboline alkaloid isolated from seeds of PEGANUM.. harmaline : A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7 and has been reduced across the 3,4 bond.	7.91	4	harmala alkaloid	oneirogen
miltefosine miltefosine: hexadecyl phosphocholine derivative of cisplatin; did not substantially activate HIV long terminal repeat; less toxic than cisplatin. miltefosine : A phospholipid that is the hexadecyl monoester of phosphocholine.	2.6	1	phosphocholines; phospholipid	anti-inflammatory agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antiprotozoal drug; apoptosis inducer; immunomodulator; protein kinase inhibitor
hexobarbital Hexobarbital: A barbiturate that is effective as a hypnotic and sedative.. hexobarbital : A member of the class of barbiturates taht is barbituric acid substituted at N-1 by methyl and at C-5 by methyl and cyclohex-1-enyl groups.	2.08	1	barbiturates
hydroxyurea [no description available]	1.96	1	one-carbon compound; ureas	antimetabolite; antimitotic; antineoplastic agent; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; genotoxin; immunomodulator; radical scavenger; teratogenic agent
phenelzine Phenelzine: One of the MONOAMINE OXIDASE INHIBITORS used to treat DEPRESSION; PHOBIC DISORDERS; and PANIC.	1.99	1	primary amine
ici 118551 [no description available]	2.06	1	indanes
imipramine Imipramine: The prototypical tricyclic antidepressant. It has been used in major depression, dysthymia, bipolar depression, attention-deficit disorders, agoraphobia, and panic disorders. It has less sedative effect than some other members of this therapeutic group.. imipramine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine substituted by a 3-(dimethylamino)propyl group at the nitrogen atom.	2.06	1	dibenzoazepine	adrenergic uptake inhibitor; antidepressant; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
indomethacin Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.	2.46	2	aromatic ether; indole-3-acetic acids; monochlorobenzenes; N-acylindole	analgesic; drug metabolite; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; gout suppressant; non-steroidal anti-inflammatory drug; xenobiotic metabolite; xenobiotic
iodoacetamide [no description available]	1.98	1
iproniazid [no description available]	3.94	12	carbohydrazide; pyridines
isoniazid Hydra: A genus of freshwater polyps in the family Hydridae, order Hydroida, class HYDROZOA. They are of special interest because of their complex organization and because their adult organization corresponds roughly to the gastrula of higher animals.. hydrazide : Compounds derived from oxoacids RkE(=O)l(OH)m (l =/= 0) by replacing -OH by -NRNR2 (R groups are commonly H). (IUPAC).	7.81	3	carbohydrazide	antitubercular agent; drug allergen
ketanserin Ketanserin: A selective serotonin receptor antagonist with weak adrenergic receptor blocking properties. The drug is effective in lowering blood pressure in essential hypertension. It also inhibits platelet aggregation. It is well tolerated and is particularly effective in older patients.. ketanserin : A member of the class of quinazolines that is quinazoline-2,4(1H,3H)-dione which is substituted at position 3 by a 2-[4-(p-fluorobenzoyl)piperidin-1-yl]ethyl group.	2.7	3	aromatic ketone; organofluorine compound; piperidines; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; cardiovascular drug; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; serotonergic antagonist
kojic acid [no description available]	2.49	2	4-pyranones; enol; primary alcohol	Aspergillus metabolite; EC 1.10.3.1 (catechol oxidase) inhibitor; EC 1.10.3.2 (laccase) inhibitor; EC 1.13.11.24 (quercetin 2,3-dioxygenase) inhibitor; EC 1.14.18.1 (tyrosinase) inhibitor; EC 1.4.3.3 (D-amino-acid oxidase) inhibitor; NF-kappaB inhibitor; skin lightening agent
lorazepam Lorazepam: A benzodiazepine used as an anti-anxiety agent with few side effects. It also has hypnotic, anticonvulsant, and considerable sedative properties and has been proposed as a preanesthetic agent.	2.67	3	benzodiazepine
6-anilino-5,8-quinolinedione 6-anilino-5,8-quinolinedione: structure given in first source; SRS-A & guanylate cyclase antagonist. 6-anilino-5,8-quinolinedione : A quinolone that is quinoline-5,8-dione in which the hydrogen at position 6 is replaced by an anilino group.	2.02	1	aminoquinoline; aromatic amine; p-quinones; quinolone	antineoplastic agent; EC 4.6.1.2 (guanylate cyclase) inhibitor
malathion Malathion: A wide spectrum aliphatic organophosphate insecticide widely used for both domestic and commercial agricultural purposes.. malathion : A racemate comprising equimolar amounts of (R) and (S)-malathion. It is a broad spectrum organophosphate proinsecticide used to control a wide range of pests including Coleoptera, Diptera, fruit flies, mosquitos and spider mites.. diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate : A diester that is diethyl succinate in which position 2 is substituted by a (dimethoxyphosphorothioyl)thio group.	7.25	1	diester; ethyl ester; organic thiophosphate
mecamylamine Mecamylamine: A nicotinic antagonist that is well absorbed from the gastrointestinal tract and crosses the blood-brain barrier. Mecamylamine has been used as a ganglionic blocker in treating hypertension, but, like most ganglionic blockers, is more often used now as a research tool.	2.13	1	primary aliphatic amine
methamidophos methamidophos: structure. methamidophos : An organic thiophosphate resulting from the N-deacylation of the proinsecticide acephate.	7.07	1	organic thiophosphate; organothiophosphate insecticide; phosphoramide	acaricide; agrochemical; avicide
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.	2.17	1	C-nitro compound; imidazoles; primary alcohol	antiamoebic agent; antibacterial drug; antimicrobial agent; antiparasitic agent; antitrichomonal drug; environmental contaminant; prodrug; radiosensitizing agent; xenobiotic
moclobemide Moclobemide: A reversible inhibitor of monoamine oxidase type A; (RIMA); (see MONOAMINE OXIDASE INHIBITORS) that has antidepressive properties.. moclobemide : A member of the class of benzamides that is benzamide substituted by a chloro group at position 4 and a 2-(morpholin-4-yl)ethyl group at the nitrogen atom. It acts as a reversible monoamine oxidase inhibitor and is used in the treatment of depression.	3.95	12	benzamides; monochlorobenzenes; morpholines	antidepressant; environmental contaminant; xenobiotic
ethylmaleimide Ethylmaleimide: A sulfhydryl reagent that is widely used in experimental biochemical studies.	1.98	1	maleimides	anticoronaviral agent; EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.1.1 (hexokinase) inhibitor
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.	4.15	15	aromatic ether; dichlorobenzene; terminal acetylenic compound; tertiary amino compound	antidepressant; EC 1.4.3.4 (monoamine oxidase) inhibitor
nalidixic acid [no description available]	2.49	2	1,8-naphthyridine derivative; monocarboxylic acid; quinolone antibiotic	antibacterial drug; antimicrobial agent; DNA synthesis inhibitor
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.	2.43	2	carbazoles
papaverine Papaverine: An alkaloid found in opium but not closely related to the other opium alkaloids in its structure or pharmacological actions. It is a direct-acting smooth muscle relaxant used in the treatment of impotence and as a vasodilator, especially for cerebral vasodilation. The mechanism of its pharmacological actions is not clear, but it apparently can inhibit phosphodiesterases and it may have direct actions on calcium channels.. papaverine : A benzylisoquinoline alkaloid that is isoquinoline substituted by methoxy groups at positions 6 and 7 and a 3,4-dimethoxybenzyl group at position 1. It has been isolated from Papaver somniferum.	1.95	1	benzylisoquinoline alkaloid; dimethoxybenzene; isoquinolines	antispasmodic drug; vasodilator agent
pargyline Pargyline: A monoamine oxidase inhibitor with antihypertensive properties.	3.11	5	aromatic amine
pentobarbital Pentobarbital: A short-acting barbiturate that is effective as a sedative and hypnotic (but not as an anti-anxiety) agent and is usually given orally. It is prescribed more frequently for sleep induction than for sedation but, like similar agents, may lose its effectiveness by the second week of continued administration. (From AMA Drug Evaluations Annual, 1994, p236). pentobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and sec-pentyl groups.	2.03	1	barbiturates	GABAA receptor agonist
phenolphthalein Phenolphthalein: An acid-base indicator which is colorless in acid solution, but turns pink to red as the solution becomes alkaline. It is used medicinally as a cathartic.	2.08	1	phenols
phenoxybenzamine Phenoxybenzamine: An alpha-adrenergic antagonist with long duration of action. It has been used to treat hypertension and as a peripheral vasodilator.	2.36	2	aromatic amine
piracetam Piracetam: A compound suggested to be both a nootropic and a neuroprotective agent.	1.98	1	organonitrogen compound; organooxygen compound
pyridoxal phosphate-6-azophenyl-2',4'-disulfonic acid pyridoxal phosphate-6-azophenyl-2',4'-disulfonic acid: a novel antagonist that selectively blocks P2 purinoceptor receptors; a useful tool to study co-transmission in tissues when ATP and coexisting neurotransmitters act in concert. 5'-phosphopyridoxal-6-azobenzene-2,4-disulfonic acid : An arenesulfonic acid that is pyridoxal 5'-phosphate carrying an additional 2,4-disulfophenylazo substituent at position 6.	2.4	2	arenesulfonic acid; azobenzenes; methylpyridines; monohydroxypyridine; organic phosphate; pyridinecarbaldehyde	purinergic receptor P2X antagonist
prazosin Prazosin: A selective adrenergic alpha-1 antagonist used in the treatment of HEART FAILURE; HYPERTENSION; PHEOCHROMOCYTOMA; RAYNAUD DISEASE; PROSTATIC HYPERTROPHY; and URINARY RETENTION.. prazosin : A member of the class of piperazines that is piperazine substituted by a furan-2-ylcarbonyl group and a 4-amino-6,7-dimethoxyquinazolin-2-yl group at positions 1 and 4 respectively.	2.71	3	aromatic ether; furans; monocarboxylic acid amide; piperazines; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
prilocaine Prilocaine: A local anesthetic that is similar pharmacologically to LIDOCAINE. Currently, it is used most often for infiltration anesthesia in dentistry.. prilocaine : An amino acid amide in which N-propyl-DL-alanine and 2-methylaniline have combined to form the amide bond; used as a local anaesthetic.	2.03	1	amino acid amide; monocarboxylic acid amide	anticonvulsant; local anaesthetic
primaquine Primaquine: An aminoquinoline that is given by mouth to produce a radical cure and prevent relapse of vivax and ovale malarias following treatment with a blood schizontocide. It has also been used to prevent transmission of falciparum malaria by those returning to areas where there is a potential for re-introduction of malaria. Adverse effects include anemias and GI disturbances. (From Martindale, The Extra Pharmacopeia, 30th ed, p404). primaquine : An N-substituted diamine that is pentane-1,4-diamine substituted by a 6-methoxyquinolin-8-yl group at the N(4) position. It is a drug used in the treatment of malaria and Pneumocystis pneumonia.	2.6	1	aminoquinoline; aromatic ether; N-substituted diamine	antimalarial
propidium Propidium: Quaternary ammonium analog of ethidium; an intercalating dye with a specific affinity to certain forms of DNA and, used as diiodide, to separate them in density gradients; also forms fluorescent complexes with cholinesterase which it inhibits.	2.44	2	phenanthridines; quaternary ammonium ion	fluorochrome; intercalator
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.	2.39	2	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic
protriptyline Protriptyline: Tricyclic antidepressant similar in action and side effects to IMIPRAMINE. It may produce excitation.	2.06	1	carbotricyclic compound	antidepressant
ritanserin Ritanserin: A selective and potent serotonin-2 antagonist that is effective in the treatment of a variety of syndromes related to anxiety and depression. The drug also improves the subjective quality of sleep and decreases portal pressure.. ritanserin : A thiazolopyrimidine that is 5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one which is substituted at position 7 by a methyl group and at position 6 by a 2-{4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl}ethyl group. A potent and long-acting seratonin (5-hydroxytryptamine, 5-HT) antagonist of the subtype 5-HT2 (Ki = 0.39 nM), it is used in the treatment of a variety of disorders including anxiety, depression and schizophrenia. It has little sedative action.	2.01	1	organofluorine compound; piperidines; thiazolopyrimidine	antidepressant; antipsychotic agent; anxiolytic drug; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; serotonergic antagonist
iodoacetic acid Iodoacetic Acid: A derivative of ACETIC ACID that contains one IODINE atom attached to its methyl group.. iodoacetic acid : A haloacetic acid that is acetic acid in which one of the hydrogens of the methyl group is replaced by an iodine atom.	2.39	2	haloacetic acid; organoiodine compound	alkylating agent
vorinostat Vorinostat: A hydroxamic acid and anilide derivative that acts as a HISTONE DEACETYLASE inhibitor. It is used in the treatment of CUTANEOUS T-CELL LYMPHOMA and SEZARY SYNDROME.. vorinostat : A dicarboxylic acid diamide comprising suberic (octanedioic) acid coupled to aniline and hydroxylamine. A histone deacetylase inhibitor, it is marketed under the name Zolinza for the treatment of cutaneous T cell lymphoma (CTCL).	2.08	1	dicarboxylic acid diamide; hydroxamic acid	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor
sulfamethazine Sulfamethazine: A sulfanilamide anti-infective agent. It has a spectrum of antimicrobial action similar to other sulfonamides.. sulfamethazine : A sulfonamide consisting of pyrimidine with methyl substituents at the 4- and 6-positions and a 4-aminobenzenesulfonamido group at the 2-position.	2	1	pyrimidines; sulfonamide antibiotic; sulfonamide	antibacterial drug; antiinfective agent; antimicrobial agent; carcinogenic agent; drug allergen; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; ligand; xenobiotic
sulfanilamide [no description available]	3.21	1	substituted aniline; sulfonamide antibiotic; sulfonamide	antibacterial agent; drug allergen; EC 4.2.1.1 (carbonic anhydrase) inhibitor
sulforaphane sulforaphane: from Cardaria draba L.. sulforaphane : An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.	2.08	1	isothiocyanate; sulfoxide	antineoplastic agent; antioxidant; EC 3.5.1.98 (histone deacetylase) inhibitor; plant metabolite
suramin Suramin: A polyanionic compound with an unknown mechanism of action. It is used parenterally in the treatment of African trypanosomiasis and it has been used clinically with diethylcarbamazine to kill the adult Onchocerca. (From AMA Drug Evaluations Annual, 1992, p1643) It has also been shown to have potent antineoplastic properties.. suramin : A member of the class of phenylureas that is urea in which each of the amino groups has been substituted by a 3-({2-methyl-5-[(4,6,8-trisulfo-1-naphthyl)carbamoyl]phenyl}carbamoyl)phenyl group. An activator of both the rabbit skeletal muscle RyR1 and sheep cardiac RyR2 isoform ryanodine receptor channels, it has been used for the treatment of human African trypanosomiasis for over 100 years.	1.99	1	naphthalenesulfonic acid; phenylureas; secondary carboxamide	angiogenesis inhibitor; antinematodal drug; antineoplastic agent; apoptosis inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; GABA antagonist; GABA-gated chloride channel antagonist; purinergic receptor P2 antagonist; ryanodine receptor agonist; trypanocidal drug
gatifloxacin Gatifloxacin: A fluoroquinolone antibacterial agent and DNA TOPOISOMERASE II inhibitor that is used as an ophthalmic solution for the treatment of BACTERIAL CONJUNCTIVITIS.. gatifloxacin : A monocarboxylic acid that is 4-oxo-1,4-dihydroquinoline-3-carboxylic acid which is substituted on the nitrogen by a cyclopropyl group and at positions 6, 7, and 8 by fluoro, 3-methylpiperazin-1-yl, and methoxy groups, respectively. Gatifloxacin is an antibiotic of the fourth-generation fluoroquinolone family, that like other members of that family, inhibits the bacterial topoisomerase type-II enzymes.	2.02	1	N-arylpiperazine; organofluorine compound; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antiinfective agent; antimicrobial agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
tilorone Tilorone: An antiviral agent used as its hydrochloride. It is the first recognized synthetic, low-molecular-weight compound that is an orally active interferon inducer, and is also reported to have antineoplastic and anti-inflammatory actions.. tilorone : A member of the class of fluoren-9-ones that is 9H-fluoren-9-one which is substituted by a 2-(diethylamino)ethoxy group at positions 2 and 7. It is an interferon inducer and a selective alpha7 nicotinic acetylcholine receptor (alpha7 nAChR) agonist. Its hydrochloride salt is used as an antiviral drug.	1.96	1	aromatic ether; diether; fluoren-9-ones; tertiary amino compound	anti-inflammatory agent; antineoplastic agent; antiviral agent; interferon inducer; nicotinic acetylcholine receptor agonist
trifluralin Trifluralin: A microtubule-disrupting pre-emergence herbicide.. trifluralin : A substituted aniline that is N,N-dipropylaniline substituted by a nitro groups at positions 2 and 6 and a trifluoromethyl group at position 4. It is an agrochemical used as a pre-emergence herbicide.	2.6	1	(trifluoromethyl)benzenes; C-nitro compound; substituted aniline	agrochemical; environmental contaminant; herbicide; xenobiotic
tyramine [no description available]	1.98	1	monoamine molecular messenger; primary amino compound; tyramines	EC 3.1.1.8 (cholinesterase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter
urethane [no description available]	1.98	1	carbamate ester	fungal metabolite; mutagen
mitomycin Mitomycin: An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.. mitomycin : A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.	2.01	1	mitomycin	alkylating agent; antineoplastic agent
reserpine Reserpine: An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria. Reserpine inhibits the uptake of norepinephrine into storage vesicles resulting in depletion of catecholamines and serotonin from central and peripheral axon terminals. It has been used as an antihypertensive and an antipsychotic as well as a research tool, but its adverse effects limit its clinical use.. reserpine : An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria.	2.01	1	alkaloid ester; methyl ester; yohimban alkaloid	adrenergic uptake inhibitor; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; first generation antipsychotic; plant metabolite; xenobiotic
phentolamine Phentolamine: A nonselective alpha-adrenergic antagonist. It is used in the treatment of hypertension and hypertensive emergencies, pheochromocytoma, vasospasm of RAYNAUD DISEASE and frostbite, clonidine withdrawal syndrome, impotence, and peripheral vascular disease.. phentolamine : A substituted aniline that is 3-aminophenol in which the hydrogens of the amino group are replaced by 4-methylphenyl and 4,5-dihydro-1H-imidazol-2-ylmethyl groups respectively. An alpha-adrenergic antagonist, it is used for the treatment of hypertension.	1.95	1	imidazoles; phenols; substituted aniline; tertiary amino compound	alpha-adrenergic antagonist; vasodilator agent
alloxan Alloxan: Acidic compound formed by oxidation of URIC ACID. It is isolated as an efflorescent crystalline hydrate.. alloxan : A member of the class of pyrimidones, the structure of which is that of perhydropyrimidine substituted at C-2, -4, -5 and -6 by oxo groups.	6.92	1	pyrimidone	hyperglycemic agent; metabolite
thymidine [no description available]	1.95	1	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
hydroxyproline Hydroxyproline: A hydroxylated form of the imino acid proline. A deficiency in ASCORBIC ACID can result in impaired hydroxyproline formation.. hydroxyproline : A proline derivative that is proline substituted by at least one hydroxy group.	2.38	2	4-hydroxyproline; L-alpha-amino acid zwitterion	human metabolite; mouse metabolite; plant metabolite
3,4-dichlorobenzoic acid 3,4-dichlorobenzoic acid: structure given in first source. 3,4-dichlorobenzoic acid : A chlorobenzoic acid carrying chloro substituents at positions 3 and 4.	2.41	1	chlorobenzoic acid
thyroxine Thyroxine: The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (MONOIODOTYROSINE) and the coupling of iodotyrosines (DIIODOTYROSINE) in the THYROGLOBULIN. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form TRIIODOTHYRONINE which exerts a broad spectrum of stimulatory effects on cell metabolism.. thyroxine : An iodothyronine compound having iodo substituents at the 3-, 3'-, 5- and 5'-positions.	2.05	1	2-halophenol; iodophenol; L-phenylalanine derivative; non-proteinogenic L-alpha-amino acid; thyroxine zwitterion; thyroxine	antithyroid drug; human metabolite; mouse metabolite; thyroid hormone
spironolactone Spironolactone: A potassium sparing diuretic that acts by antagonism of aldosterone in the distal renal tubules. It is used mainly in the treatment of refractory edema in patients with congestive heart failure, nephrotic syndrome, or hepatic cirrhosis. Its effects on the endocrine system are utilized in the treatments of hirsutism and acne but they can lead to adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p827). spironolactone : A steroid lactone that is 17alpha-pregn-4-ene-21,17-carbolactone substituted by an oxo group at position 3 and an alpha-acetylsulfanyl group at position 7.	2.54	2	3-oxo-Delta(4) steroid; oxaspiro compound; steroid lactone; thioester	aldosterone antagonist; antihypertensive agent; diuretic; environmental contaminant; xenobiotic
aldosterone [no description available]	1.95	1	11beta-hydroxy steroid; 18-oxo steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid hormone; mineralocorticoid; primary alpha-hydroxy ketone; steroid aldehyde	human metabolite; mouse metabolite
penicillamine Penicillamine: 3-Mercapto-D-valine. The most characteristic degradation product of the penicillin antibiotics. It is used as an antirheumatic and as a chelating agent in Wilson's disease.. penicillamine : An alpha-amino acid having the structure of valine substituted at the beta position with a sulfanyl group.	1.96	1	non-proteinogenic alpha-amino acid; penicillamine	antirheumatic drug; chelator; copper chelator; drug allergen
androsterone [no description available]	7.21	1	17-oxo steroid; 3alpha-hydroxy steroid; androstanoid; C19-steroid	androgen; anticonvulsant; human blood serum metabolite; human metabolite; human urinary metabolite; mouse metabolite; pheromone
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.	7.11	1	17-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; androstanoid	androgen; human metabolite; mouse metabolite
pentylenetetrazole Pentylenetetrazole: A pharmaceutical agent that displays activity as a central nervous system and respiratory stimulant. It is considered a non-competitive GAMMA-AMINOBUTYRIC ACID antagonist. Pentylenetetrazole has been used experimentally to study seizure phenomenon and to identify pharmaceuticals that may control seizure susceptibility.. pentetrazol : An organic heterobicyclic compound that is 1H-tetrazole in which the hydrogens at positions 1 and 5 are replaced by a pentane-1,5-diyl group. A central and respiratory stimulant, it was formerly used for the treatment of cough and other respiratory tract disorders, cardiovascular disorders including hypotension, and pruritis.	3.7	10	organic heterobicyclic compound; organonitrogen heterocyclic compound
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.	2.69	3	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
glutamine Glutamine: A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from GLUTAMIC ACID and AMMONIA. It is the principal carrier of NITROGEN in the body and is an important energy source for many cells.. L-glutamine : An optically active form of glutamine having L-configuration.. glutamine : An alpha-amino acid that consists of butyric acid bearing an amino substituent at position 2 and a carbamoyl substituent at position 4.	1.94	1	amino acid zwitterion; glutamine family amino acid; glutamine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
lysine Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.	7.39	2	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
allyl isothiocyanate allyl isothiocyanate: used in the manufacture of flavors, war gases; medical use as a counterirritant; structure. allyl isothiocyanate : An isothiocyanate with the formula CH2=CHCH2N=C=S. A colorless oil with boiling point 152degreeC, it is responsible for the pungent taste of mustard, horseradish, and wasabi.	2.08	1	alkenyl isothiocyanate; isothiocyanate	antimicrobial agent; antineoplastic agent; apoptosis inducer; lachrymator; metabolite
cyanides Cyanides: Inorganic salts of HYDROGEN CYANIDE containing the -CN radical. The concept also includes isocyanides. It is distinguished from NITRILES, which denotes organic compounds containing the -CN radical.. cyanides : Salts and C-organyl derivatives of hydrogen cyanide, HC#N.. isocyanide : The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)).. cyanide : A pseudohalide anion that is the conjugate base of hydrogen cyanide.	7.77	3	pseudohalide anion	EC 1.9.3.1 (cytochrome c oxidase) inhibitor
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	2.04	1	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
tubocurarine Tubocurarine: A neuromuscular blocker and active ingredient in CURARE; plant based alkaloid of Menispermaceae.. tubocurarine : A benzylisoquinoline alkaloid muscle relaxant which constitutes the active component of curare.. isoquinoline alkaloid : Any alkaloid that has a structure based on an isoquinoline nucleus. They are derived from the amino acids like tyrosine and phenylalanine.	1.95	1	bisbenzylisoquinoline alkaloid	drug allergen; muscle relaxant; nicotinic antagonist
apomorphine Apomorphine: A derivative of morphine that is a dopamine D2 agonist. It is a powerful emetic and has been used for that effect in acute poisoning. It has also been used in the diagnosis and treatment of parkinsonism, but its adverse effects limit its use.	2	1	aporphine alkaloid	alpha-adrenergic drug; antidyskinesia agent; antiparkinson drug; dopamine agonist; emetic; serotonergic drug
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	2.88	4	adenosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite; human 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.	3.22	5	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.	2.04	1	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.	2.17	1	benzoxazole	allelochemical; phytoalexin
levodopa Levodopa: The naturally occurring form of DIHYDROXYPHENYLALANINE and the immediate precursor of DOPAMINE. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to DOPAMINE. It is used for the treatment of PARKINSONIAN DISORDERS and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system.. L-dopa : An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease	1.98	1	amino acid zwitterion; dopa; L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	allelochemical; antidyskinesia agent; antiparkinson drug; dopaminergic agent; hapten; human metabolite; mouse metabolite; neurotoxin; plant growth retardant; plant metabolite; prodrug
edetic acid Edetic Acid: A chelating agent that sequesters a variety of polyvalent cations such as CALCIUM. It is used in pharmaceutical manufacturing and as a food additive.	2.66	3	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
phenylethyl alcohol Phenylethyl Alcohol: An antimicrobial, antiseptic, and disinfectant that is used also as an aromatic essence and preservative in pharmaceutics and perfumery.. 2-phenylethanol : A primary alcohol that is ethanol substituted by a phenyl group at position 2.	1.98	1	benzenes; primary alcohol	Aspergillus metabolite; fragrance; plant growth retardant; plant metabolite; Saccharomyces cerevisiae metabolite
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	1.97	1	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
adenosine monophosphate Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.	1.95	1	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
3-hydroxy-2-oxoindole 3-hydroxyindolin-2-one: structure in first source. 3-hydroxyindolin-2-one : An oxindole that is 1,3-dihydro-2H-indol-2-one substituted by a hydroxy group at position 3.	3.3	6	hydroxyindoles; oxindoles
methylene blue Methylene Blue: A compound consisting of dark green crystals or crystalline powder, having a bronze-like luster. Solutions in water or alcohol have a deep blue color. Methylene blue is used as a bacteriologic stain and as an indicator. It inhibits GUANYLATE CYCLASE, and has been used to treat cyanide poisoning and to lower levels of METHEMOGLOBIN.. methylene blue : An organic chloride salt having 3,7-bis(dimethylamino)phenothiazin-5-ium as the counterion. A commonly used dye that also exhibits antioxidant, antimalarial, antidepressant and cardioprotective properties.	2.07	1	organic chloride salt	acid-base indicator; antidepressant; antimalarial; antimicrobial agent; antioxidant; cardioprotective agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 4.6.1.2 (guanylate cyclase) inhibitor; fluorochrome; histological dye; neuroprotective agent; physical tracer
4-toluenesulfonic acid 4-toluenesulfonic acid: RN given refers to parent cpd; other RNs in 9th CI Form Index. toluene-4-sulfonic acid : An arenesulfonic acid that is benzenesulfonic acid in which the hydrogen at position 4 is replaced by a methyl group.	2.1	1	arenesulfonic acid; toluenes
uridine triphosphate Uridine Triphosphate: Uridine 5'-(tetrahydrogen triphosphate). A uracil nucleotide containing three phosphate groups esterified to the sugar moiety.	2.02	1	pyrimidine ribonucleoside 5'-triphosphate; uridine 5'-phosphate	Escherichia coli metabolite; mouse metabolite
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.	1.97	1	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
desoxycorticosterone Desoxycorticosterone: A steroid metabolite that is the 11-deoxy derivative of CORTICOSTERONE and the 21-hydroxy derivative of PROGESTERONE	6.93	1	20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; mineralocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
cycloheximide Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.	2.05	1	antibiotic fungicide; cyclic ketone; dicarboximide; piperidine antibiotic; piperidones; secondary alcohol	anticoronaviral agent; bacterial metabolite; ferroptosis inhibitor; neuroprotective agent; protein synthesis inhibitor
barbituric acid barbituric acid: RN given refers to parent cpd; structure from Merck Index, 9th ed, #966. barbituric acid : A barbiturate, the structure of which is that of perhydropyrimidine substituted at C-2, -4 and -6 by oxo groups. Barbituric acid is the parent compound of barbiturate drugs, although it is not itself pharmacologically active.	6.92	1	barbiturates	allergen; xenobiotic
mannitol [no description available]	2.03	1	mannitol	allergen; antiglaucoma drug; compatible osmolytes; Escherichia coli metabolite; food anticaking agent; food bulking agent; food humectant; food stabiliser; food thickening agent; hapten; metabolite; osmotic diuretic; sweetening agent
cytarabine [no description available]	2.25	1	beta-D-arabinoside; monosaccharide derivative; pyrimidine nucleoside	antimetabolite; antineoplastic agent; antiviral agent; immunosuppressive agent
dithionitrobenzoic acid Dithionitrobenzoic Acid: A standard reagent for the determination of reactive sulfhydryl groups by absorbance measurements. It is used primarily for the determination of sulfhydryl and disulfide groups in proteins. The color produced is due to the formation of a thio anion, 3-carboxyl-4-nitrothiophenolate.. dithionitrobenzoic acid : An organic disulfide that results from the formal oxidative dimerisation of 2-nitro-5-thiobenzoic acid. An indicator used to quantify the number or concentration of thiol groups.	1.98	1	nitrobenzoic acid; organic disulfide	indicator
phenacyl bromide phenacyl bromide: structure. phenacyl bromide : An alpha-bromoketone that is acetophenone substituted by a bromo group at position 2.	7.1	1	acetophenones; alpha-bromoketone	metabolite
ornithine Ornithine: An amino acid produced in the urea cycle by the splitting off of urea from arginine.. ornithine : An alpha-amino acid that is pentanoic acid bearing two amino substituents at positions 2 and 5.	1.94	1	non-proteinogenic L-alpha-amino acid; ornithine	algal metabolite; hepatoprotective agent; mouse metabolite
histidine Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.	2.03	1	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
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.	8.39	7	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
arginine Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.	7.68	3	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
ethylene Plastipore: high density polyethylene sponge biocompatible material; used as posts in dental bridges	2.91	3	alkene; gas molecular entity	plant hormone; refrigerant
acetylene [no description available]	7.96	4	alkyne; gas molecular entity; terminal acetylenic compound
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	boranes; mononuclear parent hydride
vinyl chloride Vinyl Chloride: A gas that has been used as an aerosol propellant and is the starting material for polyvinyl resins. Toxicity studies have shown various adverse effects, particularly the occurrence of liver neoplasms.. chloroethene : A monohaloethene that is ethene in which one of the hydrogens has been replaced by a chloro group.	1.98	1	chloroethenes; gas molecular entity; monohaloethene	carcinogenic agent
3-mercaptopropionic acid 3-Mercaptopropionic Acid: An inhibitor of glutamate decarboxylase. It decreases the GAMMA-AMINOBUTYRIC ACID concentration in the brain, thereby causing convulsions.. 3-mercaptopropanoic acid : A mercaptopropanoic acid that is propanoic acid carrying a sulfanyl group at position 3.	1.99	1	mercaptopropanoic acid	algal metabolite
isobutyraldehyde isobutyraldehyde : A member of the class of propanals that is propanal substituted by a methyl group at position 2.	2.05	1	2-methyl-branched fatty aldehyde; propanals	Saccharomyces cerevisiae metabolite
acrylic acid acrylic acid: RN given refers to parent cpd. acrylic acid : A alpha,beta-unsaturated monocarboxylic acid that is ethene substituted by a carboxy group.	2.06	1	alpha,beta-unsaturated monocarboxylic acid	metabolite
acenaphthenequinone acenaphthoquinone : An orthoquinone that is the 1,2-dioxo derivative of acenaphthene.	2.07	1	orthoquinones	chain carrier; epitope
rotenone Derris: A plant genus of the family FABACEAE. The root is a source of rotenoids (ROTENONE) and flavonoids. Some species of Pongamia have been reclassified to this genus and some to MILLETTIA. Some species of Deguelia have been reclassified to this genus.. rotenoid : Members of the class of tetrahydrochromenochromene that consists of a cis-fused tetrahydrochromeno[3,4-b]chromene skeleton and its substituted derivatives. The term was originally restricted to natural products, but is now also used to describe semi-synthetic and fully synthetic compounds.	3.3	3	organic heteropentacyclic compound; rotenones	antineoplastic agent; metabolite; mitochondrial NADH:ubiquinone reductase inhibitor; phytogenic insecticide; piscicide; toxin
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.	2.74	3	phthalimides
5-bromoisatin [no description available]	3.56	8	indoles	anticoronaviral agent
anthranilamide [no description available]	2.1	1	substituted aniline
1-naphthol 1-naphthol: RN given refers to parent cpd. 1-naphthol : A naphthol carrying a hydroxy group at position 1.. hydroxynaphthalene : Any member of the class of naphthalenes that is naphthalene carrying one or more hydroxy groups.	2.41	1	naphthol	genotoxin; human xenobiotic metabolite
quinoline [no description available]	8.78	2	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinolines
diphenyl diphenyl: RN given refers to unlabeled cpd; structure	2.64	3	aromatic fungicide; benzenes; biphenyls	antifungal agrochemical; antimicrobial food preservative
4-biphenylamine 4-biphenylamine: used in detection of sulfates, & as a carcinogen in cancer research; RN given refers to parent cpd; structure. biphenyl-4-amine : An aminobiphenyl that is biphenyl substituted by an amino group at position 4.	2.06	1	aminobiphenyl	carcinogenic agent
benzoylacetone [no description available]	6.96	1
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.	7.21	1	aromatic carboxylic acid; benzodioxoles; monocarboxylic acid	antifungal agent; EC 1.14.14.91 ( trans-cinnamate 4-monooxygenase) inhibitor; plant metabolite; vulnerary
indene indene: structure in first source. 1H-indene : An ortho-fused bicyclic arene comprising of benzene and cyclopentene rings.	2.03	1	indene; ortho-fused bicyclic arene
benzothiazole benzothiazole: structure. benzothiazole : An organic heterobicyclic compound that is a fusion product between benzene and thiazole. The parent of the class of benzothiazoles.	2.51	2	benzothiazoles	environmental contaminant; plant metabolite; xenobiotic
4-butyrolactone 4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.	3.3	6	butan-4-olide	metabolite; neurotoxin
furaldehyde Furaldehyde: A heterocyclic compound consisting of a furan where the hydrogen at position 2 is substituted by a formyl group.. furfural : An aldehyde that is furan with the hydrogen at position 2 substituted by a formyl group.	2.07	1	aldehyde; furans	Maillard reaction product; metabolite
thiophene-2-carboxaldehyde thiophene-2-carboxaldehyde: structure in first source. formylthiophene : An aldehyde that is thiophene substituted by a formyl group at position 2.	2.07	1	aldehyde; thiophenes	metabolite
trehalose alpha,alpha-trehalose : A trehalose in which both glucose residues have alpha-configuration at the anomeric carbon.	2.03	1	trehalose	Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
4-(dimethylamino)benzaldehyde p-dimethylaminobenzaldehyde: structure in first source. 4-(dimethylamino)benzaldehyde : A member of the class of benzaldehydes that is benzaldehyde carrying a dimethylamino substituent at position 4. Used as an indicator for detection of indoles and hydrazine.	2.03	1	benzaldehydes; substituted aniline; tertiary amino compound	chromogenic compound
benzylamine aminotoluene : Any member of the class of toluenes carrying one or more amino groups.	2.11	1	aralkylamine; primary amine	allergen; EC 3.5.5.1 (nitrilase) inhibitor; plant metabolite
quinuclidines Quinuclidines: A class of organic compounds which contain two rings that share a pair of bridgehead carbon atoms and contains an amine group.	2.49	2	quinuclidines; saturated organic heterobicyclic parent
ethyl cyanoacetate ethyl cyanoacetate: affect muscarinic and nicotinic receptors; RN given refers to unlabeled parent cpd	2.1	1
acrolein [no description available]	7.11	1	enal	herbicide; human xenobiotic metabolite; toxin
allyl alcohol allyl alcohol: structure. allylic alcohol : An alcohol where the hydroxy group is attached to a saturated carbon atom adjacent to a double bond (R groups may be H, organyl, etc.).. allyl alcohol : A propenol in which the C=C bond connects C-2 and C-3. It is has been found in garlic (Allium sativum). Formerly used as a herbicide for the control of various grass and weed seeds.	2.05	1	primary allylic alcohol; propenol	antibacterial agent; fungicide; herbicide; insecticide; plant metabolite
glyoxal [no description available]	1.95	1	dialdehyde	agrochemical; allergen; pesticide; plant growth regulator
3-hydroxybutanal [no description available]	3.36	6
cyclohexanone [no description available]	7.52	2	cyclohexanones	human xenobiotic metabolite
2-aminopyrimidine pyrimidin-2-amine : An aminopyrimidine carrying an amino group at position 2.. aminopyrimidine : A member of the class of pyrimidines that is pyrimidine substituted by at least one amino group and its derivatives.	7.1	1	aminopyrimidine
boron trifluoride etherate [no description available]	2.05	1
dicyanmethane malononitrile : A dinitrile that is methane substituted by two cyano groups.	3.47	7	aliphatic nitrile; dinitrile
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.	8.35	6	pyrrole; secondary amine
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	3.41	1	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	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.	7.07	1	cycloalkane; volatile organic compound	non-polar solvent
bis(2-chloroethyl)ether bis(2-chloroethyl)ether: structure	1.98	1	ether
acetol hydroxyacetone : A propanone that is acetone in which one of the methyl hydrogens is replaced by a hydroxy group.	2.07	1	methyl ketone; primary alcohol; primary alpha-hydroxy ketone; propanones	Escherichia coli metabolite; human metabolite; mouse metabolite
2'-hydroxyacetophenone 2-acetylphenol : A monohydroxyacetophenone that is acetophenone in which one of the hydrogens ortho to the acetyl group has been replaced by a hydroxy group.	7.48	2	monohydroxyacetophenone; phenols	flavouring agent
benzoin [no description available]	7.1	1	benzoins; secondary alpha-hydroxy ketone	EC 3.1.1.1 (carboxylesterase) inhibitor
anthracene acene : A polycyclic aromatic hydrocarbon consisting of fused benzene rings in a rectilinear arrangement.. acenes : Polycyclic aromatic hydrocarbons consisting of fused benzene rings in a rectilinear arrangement and their substitution derivatives.	6.92	1	acene; anthracenes; ortho-fused tricyclic hydrocarbon
benzil benzil: structure. benzil : An alpha-diketone that is ethane-1,2-dione substituted by phenyl groups at positions 1 and 2 respectively.	2.07	1	alpha-diketone; aromatic ketone
2-naphthol 2-naphthol: RN given refers to parent cpd. 2-naphthol : A naphthol carrying a hydroxy group at position 2.. naphthols : Any hydroxynaphthalene derivative that has a single hydroxy substituent.	2.82	2	naphthol	antinematodal drug; genotoxin; human urinary metabolite; human xenobiotic metabolite; mouse metabolite; radical scavenger
2-aminobenzothiazole [no description available]	2.17	1	benzothiazoles
shikimic acid Shikimic Acid: A tri-hydroxy cyclohexene carboxylic acid important in biosynthesis of so many compounds that the shikimate pathway is named after it.. shikimic acid : A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3R,4S,5R stereoisomer). It is an intermediate metabolite in plants and microorganisms.	2.41	1	alpha,beta-unsaturated monocarboxylic acid; cyclohexenecarboxylic acid; hydroxy monocarboxylic acid	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
4-aminodiphenyl ether [no description available]	2.06	1
2,6-diaminopyridine 2,6-diaminopyridine: structure in first source	7.05	1
sodium cyanide Sodium Cyanide: A highly poisonous compound that is an inhibitor of many metabolic processes and is used as a test reagent for the function of chemoreceptors. It is also used in many industrial processes.. sodium cyanide : A cyanide salt containing equal numbers of sodium cations and cyanide anions.	2.11	1	cyanide salt; one-carbon compound; sodium salt	EC 1.15.1.1 (superoxide dismutase) inhibitor
yohimbine Yohimbine: A plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of ERECTILE DYSFUNCTION.. yohimbine : An indole alkaloid with alpha2-adrenoceptor antagonist activity. It is produced by Corynanthe johimbe and Rauwolfia serpentina.	7.7	3	methyl 17-hydroxy-20xi-yohimban-16-carboxylate	alpha-adrenergic antagonist; dopamine receptor D2 antagonist; serotonergic antagonist
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.	2.01	1	dithiocarbamic acids	chelator; copper chelator
aziridine [no description available]	7.13	1	azacycloalkane; aziridines; saturated organic heteromonocyclic parent	alkylating agent
hydroxytryptophol Hydroxytryptophol: 5-Hydroxy-indole-3-ethanol.	1.96	1	indoles
phthalazine phthalazine : An azaarene that is the 2,3-diaza analogue of naphthalene. The parent of the class of phthalazines.	2.07	1	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; phthalazines
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.	8.34	6	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.	7.94	4	acridines; mancude organic heterotricyclic parent; polycyclic heteroarene	genotoxin
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.	7.31	1	1-benzofurans; benzofuran
triethylenediamine triethylenediamine: RN given refers to parent cpd. triethylenediamine : An organic heterobicylic compound that is piperazine with an ethane-1,2-diyl group forming a bridge between N1 and N4. It is typically used as a catalyst in polymerization reactions.	2.1	1	bridged compound; diamine; saturated organic heterobicyclic parent; tertiary amino compound	antioxidant; catalyst; reagent
adamantane Adamantane: A tricyclo bridged hydrocarbon.	3.5	2	adamantanes; polycyclic alkane
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.	2.8	3	1,3-oxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiazoles [no description available]	8.96	12	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	7.41	1	1,2,4-triazole
pyrimidine pyrimidine : The parent compound of the pyrimidines; a diazine having the two nitrogens at the 1- and 3-positions.	3.41	1	diazine; pyrimidines	Daphnia magna metabolite
hydrazine diamine : Any polyamine that contains two amino groups.	8.88	11	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.	2.21	1	aminoimidazole; monocarboxylic acid amide	mouse metabolite
citrulline citrulline : The parent compound of the citrulline class consisting of ornithine having a carbamoyl group at the N(5)-position.	1.94	1	amino acid zwitterion; citrulline	Daphnia magna metabolite; EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; protective agent; Saccharomyces cerevisiae metabolite
5-methylpyrazole-3-carboxylic acid 5-methylpyrazole-3-carboxylic acid: structure. 5-methyl-pyrazole-3-carboxylic acid : A memebr of the class of pyrazoles that is 1H-pyrazole with methyl and carboxylic acid group substituents at positions 5 and 3 respectively.	3.11	3	monocarboxylic acid; pyrazoles	metabolite
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.	2.06	1	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.	1.97	1	monofluorobenzenes	NMR chemical shift reference compound
ketene ketene: structure. ketene : Carbonyl compounds where the C=O bond is conjugated to an alkylidene group.	7.06	1	ketene
fusarium Fusarium: A mitosporic Hypocreales fungal genus, various species of which are important parasitic pathogens of plants and a variety of vertebrates. Teleomorphs include GIBBERELLA.	2.04	1
indirubin [no description available]	4.56	9
ninhydrin Ninhydrin: 2,2-Dihydroxy-1H-indene-1,3-(2H)-dione. Reagent toxic to skin and mucus membranes. It is used in chemical assay for peptide bonds, i.e., protein determinations and has radiosensitizing properties.. ninhydrin : A member of the class of indanones that is indane-1,3-dione bearing two additional hydroxy substituents at position 2.	3.11	5	aromatic ketone; beta-diketone; indanones; ketone hydrate	colour indicator; human metabolite
indole-3-carbaldehyde indole-3-carbaldehyde: metabolite of tryptophan; structure. indole-3-carbaldehyde : A heteroarenecarbaldehyde that is indole in which the hydrogen at position 3 has been replaced by a formyl group.	2.89	3	heteroarenecarbaldehyde; indole alkaloid; indoles	bacterial metabolite; human xenobiotic metabolite; marine metabolite; plant metabolite
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.	2.03	1	indanes; ortho-fused bicyclic hydrocarbon
indoline indoline: structure given in first source	3.42	7	indoles
butenolide butenolide: inhibits experimental allergic encephalomyelitis in rats. butenolide : A gamma-lactone that consists of a 2-furanone skeleton and its substituted derivatives.	7.06	1	butenolide
carvacrol carvacrol : A phenol that is a natural monoterpene derivative of cymene. An inhibitor of bacterial growth, it is used as a food additive. Potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1).	3.25	1	botanical anti-fungal agent; p-menthane monoterpenoid; phenols	agrochemical; antimicrobial agent; flavouring agent; TRPA1 channel agonist; volatile oil component
3-pyridinaldehyde pyridine-3-carbaldehyde : A pyridinecarbaldehyde that is pyridine substituted by a formyl group at position 3.	2.07	1	pyridinecarbaldehyde
4-hydroxyphenylethanol 4-hydroxyphenylethanol: in chest gland secretion of galagos. 2-(4-hydroxyphenyl)ethanol : A phenol substituted at position 4 by a 2-hydroxyethyl group.	1.98	1	phenols	anti-arrhythmia drug; antioxidant; cardiovascular drug; fungal metabolite; geroprotector; plant metabolite; protective agent
oxetane oxetane: structure. oxetane : A saturated organic heteromonocyclic parent that is a four-membered ring comprising of three carbon atoms and an oxygen atom.	2.07	1	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.	2.44	2
thiazolidines Thiazolidines: Reduced (protonated) form of THIAZOLES. They can be oxidized to THIAZOLIDINEDIONES.	8.19	5	thiazolidine
1-chloro-2-methylpropene [no description available]	1.98	1	organochlorine compound
azomycin azomycin: RN given refers to parent cpd with specified locant; structure	2.48	2	C-nitro compound; imidazoles	antitubercular agent
phenylacetylene phenylacetylene: can polymerize into DENDRIMERS	7.44	2	benzenes
maleimide [no description available]	7.08	1	dicarboximide; maleimides	EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
delta-valerolactone [no description available]	7.05	1	delta-lactone
n-butyl nitrite n-butyl nitrite: RN given refers to parent cpd; structure in Merck Index, 9th ed, #1570	2.15	1	nitroso compound
trinitrobenzenesulfonic acid Trinitrobenzenesulfonic Acid: A reagent that is used to neutralize peptide terminal amino groups.. 2,4,6-trinitrobenzenesulfonic acid : The arenesulfonic acid that is benzenesulfonic acid with three nitro substituents in the 2-, 4- and 6-positions.	2.1	1	arenesulfonic acid; C-nitro compound	epitope; explosive; reagent
nicotinic acid hydrazide nicotinic acid hydrazide: structural homolog of isoniazid; structure given in first source	2.11	1
methyl isothiocyanate methyl isothiocyanate: structure. methyl isothiocyanate : An isothiocyanate having a methyl group attached to the nitrogen. It is also the active nematicide of the pronematicide metam-sodium.	2.07	1	isothiocyanate	fumigant; lachrymator; nematicide
isopropyl methyl ketone [no description available]	6.96	1	ketone
1-acetylisatin 1-acetylisatin: structure in first source	2.95	4	indoledione
1,3-indandione 1,3-indandione : A member of the class of indanones that is indane in which the hydrogens at positions 2 and 4 have been replaced by oxo groups.	2.03	1	aromatic ketone; beta-diketone; indanones
5-methylisatin 5-methylisatin: structure in first source	3.31	6
2,4,6-triiodophenol [no description available]	2.05	1
phenacylamine phenacylamine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #6990	2.49	2	aromatic ketone
2-hydroxy benzimidazole 2-hydroxy benzimidazole: structure in first source	2.17	1
2-pyrrolidone 2-pyrrolidone: RN given refers to parent cpd. pyrrolidin-2-one : The simplest member of the class of pyrrolidin-2-ones, consisting of pyrrolidine in which the hydrogens at position 2 are replaced by an oxo group. The lactam arising by the formal intramolecular condensation of the amino and carboxy groups of gamma-aminobutyric acid (GABA).	2.07	1	pyrrolidin-2-ones	metabolite; polar solvent
homoserine homoserine : An alpha-amino acid that is glycine substituted at the alpha-position by a 2-hydroxyethyl group.. L-homoserine : The L-enantiomer of homoserine.	2.05	1	amino acid zwitterion; homoserine	algal metabolite; Escherichia coli metabolite; human metabolite; Saccharomyces cerevisiae metabolite
hempa Hempa: A chemosterilant agent that is anticipated to be a carcinogen.	1.98	1	phosphoramide	insect sterilant; mutagen
dimethyl methylphosphonate [no description available]	1.98	1
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.	2.1	1	organofluorine compound; secondary alcohol	drug metabolite
3,4-epoxy-1-butene 3,4-epoxy-1-butene: RN given refers to monomer	2.11	1
n-phenylmaleimide N-phenylmaleimide: structure in Merck Index, 9th ed, #7104	7.07	1
pyrrole-2-carboxaldehyde 2-pyrrolecarboxaldehyde: structure in first source. pyrrole-2-carboxaldehyde : A pyrrole carrying a formyl substituent at the 2-position.	2.07	1	1,3-thiazole-2-carbaldehyde; pyrroles
phenylglyoxal [no description available]	2.07	1	phenylacetaldehydes
4-vinylbenzoic acid [no description available]	2.01	1
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.	2.07	1	pyridinecarbaldehyde
copper carbonate copper carbonate: RN given refers to 1:1 Cu(+2) salt	2	1
sodium hydroxide Sodium Hydroxide: A highly caustic substance that is used to neutralize acids and make sodium salts. (From Merck Index, 11th ed)	2.02	1	alkali metal hydroxide
zinc oxide Zinc Oxide: A mild astringent and topical protectant with some antiseptic action. It is also used in bandages, pastes, ointments, dental cements, and as a sunblock.	2.1	1	zinc molecular entity
dimethylol dihydroxyethyleneurea dimethylol dihydroxyethyleneurea: used in cotton or cotton-polyester blend fabric	1.98	1
meldrum's acid Meldrum's acid: structure given in first source	2.1	1
n-methylisatin N-methylisatin: structure given in first source	3.82	11
3-aminobiphenyl 3-aminobiphenyl: structure given in first source	2.06	1
1,4-bis(2,3-epoxypropoxy)butane [no description available]	1.98	1
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.	3.47	7	carbon oxoanion
isopropyl glycidyl ether isopropyl glycidyl ether: RN & structure given in first source	1.98	1
diadenosine tetraphosphate P(1),P(4)-bis(5'-adenosyl) tetraphosphate : A diadenosyl tetraphosphate compound having the two 5'-adenosyl residues attached at the P(1)- and P(4)-positions.	2.06	1	diadenosyl tetraphosphate	Escherichia coli metabolite; mouse metabolite
iridium Iridium: A metallic element with the atomic symbol Ir, atomic number 77, and atomic weight 192.22.	2.48	2	cobalt group element atom; platinum group metal atom
lanthanum [no description available]	7.02	1	f-block element atom; lanthanoid atom; scandium group element atom
manganese Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.	2.11	1	elemental manganese; manganese group element atom	Escherichia coli metabolite; micronutrient
mercury Mercury: A silver metallic element that exists as a liquid at room temperature. It has the atomic symbol Hg (from hydrargyrum, liquid silver), atomic number 80, and atomic weight 200.59. Mercury is used in many industrial applications and its salts have been employed therapeutically as purgatives, antisyphilitics, disinfectants, and astringents. It can be absorbed through the skin and mucous membranes which leads to MERCURY POISONING. Because of its toxicity, the clinical use of mercury and mercurials is diminishing.. mercury(0) : Elemental mercury of oxidation state zero.	1.95	1	elemental mercury; zinc group element atom	neurotoxin
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.	3.47	7	metal allergen; nickel group element atom; platinum group metal atom
praseodymium Praseodymium: An element of the rare earth family of metals. It has the atomic symbol Pr, atomic number 59, and atomic weight 140.91.	7.02	1	f-block element atom; lanthanoid 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.	2.97	4	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.	7.07	1	iron group element atom; platinum group metal atom
scandium Scandium: An element of the rare earth family of metals. It has the atomic symbol Sc, atomic number 21, and atomic weight 45.	7.76	3	d-block element atom; rare earth metal atom; scandium group element atom
silver Silver: An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.	7.1	1	copper group element atom; elemental silver	Escherichia coli metabolite
titanium Titanium: A dark-gray, metallic element of widespread distribution but occurring in small amounts with atomic number, 22, atomic weight, 47.867 and symbol, Ti; specific gravity, 4.5; used for fixation of fractures.	2.06	1	titanium group element atom
cadmium Cadmium: An element with atomic symbol Cd, atomic number 48, and atomic weight 112.41. It is a metal and ingestion will lead to CADMIUM POISONING.. elemental cadmium : An element in the zinc group of the periodic table with atomic number 48, atomic mass 112, M.P. 321degreeC, and B.P. 765degreeC). An odourless, tasteless, and highly poisonous soft, ductile, lustrous metal with electropositive properties. It has eight stable isotopes: (106)Cd, (108)Cd,(110)Cd, (111)Cd, (112)Cd, (113)Cd, (114)Cd and (116)Cd, with (112)Cd and (114)Cd being the most common.	1.94	1	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.	7.04	1	chromium group element atom; metal allergen	micronutrient
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.	7.88	3	copper group element atom; elemental gold
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.	7.48	2	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	1	titanium group element atom
camptothecin NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source	2.75	3	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
nickel chloride nickel chloride: RN given refers to cpd with MF of Ni-Cl2. nickel dichloride : A compound of nickel and chloride in which the ratio of nickel (in the +2 oxidation state) to chloride is 1:2.	2.51	2	nickel coordination entity	calcium channel blocker; hapten
phosphine phosphane : The simplest phosphine, consisting of a single phosphorus atom with three hydrogens attached.. phosphine : Phosphane (PH3) and compounds derived from it by substituting one, two or three hydrogen atoms by hydrocarbyl groups: RPH2, R2PH, R3P (R =/= H) are called primary, secondary and tertiary phosphines, respectively. A specific phosphine is preferably named as a substituted phosphane.	2.13	1	mononuclear parent hydride; phosphanes; phosphine	carcinogenic agent; fumigant insecticide
bromine Bromine: A halogen with the atomic symbol Br, atomic number 35, and atomic weight 79.904. It is a volatile reddish-brown liquid that gives off suffocating vapors, is corrosive to the skin, and may cause severe gastroenteritis if ingested.	2.06	1	diatomic bromine
fluorine Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.	2.41	2	diatomic fluorine; gas molecular entity	NMR chemical shift reference compound
nitrous acid Nitrous Acid: Nitrous acid (HNO2). A weak acid that exists only in solution. It can form water-soluble nitrites and stable esters. (From Merck Index, 11th ed)	1.95	1	nitrogen oxoacid
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.	7.71	3	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
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.	2.71	3
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.	11.23	25	selegiline; terminal acetylenic compound	geroprotector
laxagetten 4,4'-diacetoxydiphenylpyridylemethane [no description available]	2.94	4
iodine [no description available]	2.41	1	halide anion; monoatomic iodine	human metabolite
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	3.32	6	benzenes; phenyl acetates
pyrrolidine [no description available]	8.19	5	azacycloalkane; pyrrolidines; saturated organic heteromonocyclic parent
1-chloro-2-propanol 1-chloro-2-propanol: RN given refers to cpd without isomeric designation. 1-chloropropan-2-ol : A secondary alcohol that is isopropanol in which one of the methyl hydrogen atoms is substituted by chlorine.	1.98	1	organochlorine compound; secondary alcohol
carticaine Carticaine: A thiophene-containing local anesthetic pharmacologically similar to MEPIVACAINE.	2.03	1	thiophenecarboxylic acid
alkenes [no description available]	8.77	10
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	2	1	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
adenylyl imidodiphosphate Adenylyl Imidodiphosphate: 5'-Adenylic acid, monoanhydride with imidodiphosphoric acid. An analog of ATP, in which the oxygen atom bridging the beta to the gamma phosphate is replaced by a nitrogen atom. It is a potent competitive inhibitor of soluble and membrane-bound mitochondrial ATPase and also inhibits ATP-dependent reactions of oxidative phosphorylation.	2.69	3	adenosine 5'-phosphate
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	4.68	8	pseudohalide anion	mitochondrial respiratory-chain inhibitor
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.	2.05	1	penicillin allergen; penicillin	antibacterial drug
oxovanadium iv oxovanadium IV: forms complexes with simple sugars	2.1	1	vanadium oxide
toloxatone toloxatone: oxazolidinone derivative; psychotropic drug; structure. toloxatone : A racemate consisting of equimolar amounts of (R)- and (S)-toloxatone. It is a reversible monoamine oxidase A inhibitor and antidepressant.. 5-(hydroxymethyl)-3-(3-methylphenyl)-1,3-oxazolidin-2-one : A member of the class of oxazolidinones that is 5-(hydroxymethyl)-1,3-oxazolidin-2-one substituted by a 3-methylphenyl group at position 3.	2.82	2	oxazolidinone; primary alcohol; toluenes
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	1	azide; pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
2-nitrobenzofuran [no description available]	2.41	1
etoposide [no description available]	2.44	2	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor
butaclamol [no description available]	2.06	1	amino alcohol; organic heteropentacyclic compound; tertiary alcohol; tertiary amino compound	dopaminergic antagonist
10-carboxymethyl-9-acridanone 10-carboxymethyl-9-acridanone: RN given refers to parent cpd	1.96	1	acridines
5-Methoxyisatin [no description available]	3.31	6	indoles	anticoronaviral agent
ng-nitroarginine methyl ester NG-Nitroarginine Methyl Ester: A non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.	2.76	3	alpha-amino acid ester; L-arginine derivative; methyl ester; N-nitro compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor
staurosporine [no description available]	2.44	2	indolocarbazole alkaloid; organic heterooctacyclic compound	apoptosis inducer; bacterial metabolite; EC 2.7.11.13 (protein kinase C) inhibitor; geroprotector
pergolide Pergolide: A long-acting dopamine agonist which has been used to treat PARKINSON DISEASE and HYPERPROLACTINEMIA but withdrawn from some markets due to potential for HEART VALVE DISEASES.. pergolide : A diamine that is ergoline in which the beta-hydrogen at position 8 is replaced by a (methylthio)methyl group and the hydrogen attached to the piperidine nitrogen (position 6) is replaced by a propyl group. A dopamine D2 receptor agonist which also has D1 and D2 agonist properties, it is used as the mesylate salt in the management of Parkinson's disease, although it was withdrawn from the U.S. and Canadian markets in 2007 due to an increased risk of cardiac valve dysfunction.	3.48	2	diamine; methyl sulfide; organic heterotetracyclic compound	antiparkinson drug; dopamine agonist
indoxyl 3-hydroxyindole: inhibits amyloid fibril formation; structure in first source	2	1	heteroaryl hydroxy compound; hydroxyindoles
pefloxacin Pefloxacin: A synthetic broad-spectrum fluoroquinolone antibacterial agent active against most gram-negative and gram-positive bacteria.. pefloxacin : A quinolone that is 4-oxo-1,4-dihydroquinoline which is substituted at positions 1, 3, 6 and 7 by ethyl, carboxy, fluorine, and 4-methylpiperazin-1-yl groups, respectively.	2.41	1	fluoroquinolone antibiotic; monocarboxylic acid; N-alkylpiperazine; N-arylpiperazine; quinolone antibiotic; quinolone	antibacterial drug; antiinfective agent; DNA synthesis inhibitor
fomesafen fomesafen: a protoporphyrinogen oxidase-inhibiting herbicide. fomesafen : An N-sulfonylcarboxamide that is N-(methylsulfonyl)benzamide in which the phenyl ring is substituted by a nitro group at position 2 and a 2-chloro-4-(trifluoromethyl)phenoxy group at position 5. A protoporphyrinogen oxidase inhibitor, it was specially developed for use (generally as the corresponding sodium salt, fomesafen-sodium) for post-emergence control of broad-leaf weeds in soya.	1.95	1	aromatic ether; C-nitro compound; monochlorobenzenes; N-sulfonylcarboxamide; organofluorine compound; phenols	agrochemical; EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor; herbicide
duloxetine hydrochloride Duloxetine Hydrochloride: A thiophene derivative and selective NEUROTRANSMITTER UPTAKE INHIBITOR for SEROTONIN and NORADRENALINE (SNRI). It is an ANTIDEPRESSIVE AGENT and ANXIOLYTIC, and is also used for the treatment of pain in patients with DIABETES MELLITUS and FIBROMYALGIA.. (S)-duloxetine hydrochloride : A duloxetine hydrochloride in which the duloxetine moiety has S configuration.	2.31	1	duloxetine hydrochloride	antidepressant
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	3.06	5	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
vanadates Vanadates: Oxyvanadium ions in various states of oxidation. They act primarily as ion transport inhibitors due to their inhibition of Na(+)-, K(+)-, and Ca(+)-ATPase transport systems. They also have insulin-like action, positive inotropic action on cardiac ventricular muscle, and other metabolic effects.. vanadate(3-) : A vanadium oxoanion that is a trianion with formula VO4 in which the vanadium is in the +5 oxidation state and is attached to four oxygen atoms.	2.1	1	trivalent inorganic anion; vanadium oxoanion	EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor
edda EDDA: RN given refers to parent cpd. ethylenediaminediacetic acid : An ethylenediamine derivative in which two of the four amine protons of ethylenediamine are replaced by carboxymethyl groups.	2.08	1	amino dicarboxylic acid; ethylenediamine derivative; glycine derivative; polyamino carboxylic acid	bacterial xenobiotic metabolite; chelator
trifluoromethanesulfonic acid trifluoromethanesulfonic acid: deblocking reagent for peptide synthesis; RN given refers to parent cpd. triflic acid : A one-carbon compound that is methanesulfonic acid in which the hydrogens attached to the methyl carbon have been replaced by fluorines.	2.58	2	one-carbon compound; perfluoroalkanesulfonic acid
ammonium peroxydisulfate ammonium persulfate : An inorganic ammonium salt in which two of the terminal hydroxy groups of peroxydisulfuric acid are deprotonated and associated with ammonium ions as counter-cations.	2.41	1
efavirenz efavirenz: HIV-1 reverse transcriptase inhibitor. efavirenz : 1,4-Dihydro-2H-3,1-benzoxazin-2-one substituted at the 4 position by cyclopropylethynyl and trifluoromethyl groups (S configuration) and at the 6 position by chlorine. A non-nucleoside reverse transcriptase inhibitor with activity against HIV, it is used with other antiretrovirals for combination therapy of HIV infection.	2.13	1	acetylenic compound; benzoxazine; cyclopropanes; organochlorine compound; organofluorine compound	antiviral drug; HIV-1 reverse transcriptase inhibitor
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	2	1	D-glucopyranose	epitope; mouse metabolite
thiazolyl blue thiazolyl blue: RN & II refers to bromide. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide : The bromide salt of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium.	2.45	2	organic bromide salt	colorimetric reagent; dye
aica ribonucleotide AICA ribonucleotide: purine precursor that has antineoplastic activity. AICA ribonucleotide : A 1-(phosphoribosyl)imidazolecarboxamide that is acadesine in which the hydroxy group at the 5' position has been converted to its monophosphate derivative.	2.21	1	1-(phosphoribosyl)imidazolecarboxamide; aminoimidazole	cardiovascular drug; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
n-methylisatin beta-4',4'-diethylthiosemicarbazone [no description available]	2.39	2
balofloxacin balofloxacin: showed potent bactericidal activity & inhibited the supercoiling activity of DNA gyrase of S. aureus, E. coli, & P aeruginosa; structure given in first source	7.05	1
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
thiamorpholine thiamorpholine: RN given refers to parent cpd. thiomorpholine : A saturated organic heteromonocyclic parent that is an analogue of morpholine where the oxygen atom is replaced by sulfur.	2.31	1	saturated organic heteromonocyclic parent; thiomorpholines
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.	6.06	33	1,2,3-triazole
pentafluoropropionic anhydride [no description available]	1.97	1
n-phenylphthalimide N-phenylphthalimide: structure given in first source	2.45	2
sesamol sesamol: constituent of sesame oil; RN given refers to parent cpd; structure in first source	7.1	1	benzodioxoles
alpha-methylene gamma-butyrolactone alpha-methylene gamma-butyrolactone : A butan-4-olide having a methylene group at the 3-position.	2.83	3	butan-4-olide	anti-ulcer drug; gastrointestinal drug
4-aminoquinoline [no description available]	2.46	2
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)	2.46	2	2-deoxy-2-((18)F)fluoro-D-glucose; 2-deoxy-2-fluoro-aldehydo-D-glucose
pirlindole pirlindole: RN given refers to parent cpd; synonym pyrazidol refers to mono-HCl; structure in Negwer, 5th ed, #2812	2	1	carbazoles
brinzolamide brinzolamide: an antiglaucoma agent	3.41	1	sulfonamide; thienothiazine	antiglaucoma drug; EC 4.2.1.1 (carbonic anhydrase) inhibitor
4-hydroxyquinoline 4-quinolone : A quinolone that is 1,4-dihydroquinoline substituted by an oxo group at position 4.	2.05	1	monohydroxyquinoline; quinolone
benzocyclobutene benzocyclobutene : A carbobicyclic compound that is benzene fused to a cyclobutane ring.	2.15	1	carbobicyclic compound	metabolite
indole-3-carboxylic acid indole-3-carboxylic acid : An indole-3-carboxylic acid carrying a carboxy group at position 3.	1.98	1	indol-3-yl carboxylic acid	bacterial metabolite; human metabolite
lazabemide lazabemide: structure given in first source	2.02	1
indole-2-carboxylic acid [no description available]	1.98	1	indolyl carboxylic acid
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.	2.8	3	carbohydrazide; one-carbon compound
pentafluorobenzyl bromide pentafluorobenzyl bromide : A member of the class benzyl bromides that is benzyl bromide in which the hydrogens at positions 2, 3, 4, 5 and 6 of the phenyl ring are replaced by fluoro groups. It is a versatile derivatization agent in chromatography and mass spectrometry.	1.97	1	benzyl bromides; fluorobenzenes
5-aminopyrazole 5-aminopyrazole: structure in first source	2.05	1
2-phenylisatogen 2-phenylisatogen: inhibitor of mitochondrial oxidative phosphorylation; structure	1.96	1
N-Benzylphthalimide [no description available]	2.06	1	isoindoles
5-hydroxy-2-oxindole 5-hydroxyoxindole: Monoamine Oxidase Inhibitor; structure in first source	2.43	2
3-acetylcoumarin 3-acetylcoumarin: structure given in first source. 3-acetylcoumarin : A member of the class of coumarins that is coumarin in which the hydrogen at position 3 is replaced by an acetyl group.	2.06	1	coumarins
rivastigmine [no description available]	2.41	1	carbamate ester; tertiary amino compound	cholinergic drug; EC 3.1.1.8 (cholinesterase) inhibitor; neuroprotective agent
2,3-dioxo-5-indolinesulfonic acid 2,3-dioxo-5-indolinesulfonic acid: reagent for modification of tryptophan residues in peptides & proteins	3.11	5
3-indazolinone 3-indazolinone: structure given in first source	2.17	1
trimethylsilyl cyanide [no description available]	2.48	2
5-Chloro-1H-indole-2,3-dione [no description available]	3.57	8	indoles	anticoronaviral agent
5-iodoisatin 5-iodoisatin: structure in first source	8.55	8	indoles	anticoronaviral agent
nicotine (S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.	1.98	1	3-(1-methylpyrrolidin-2-yl)pyridine	anxiolytic drug; biomarker; immunomodulator; mitogen; neurotoxin; nicotinic acetylcholine receptor agonist; peripheral nervous system drug; phytogenic insecticide; plant metabolite; psychotropic drug; teratogenic agent; xenobiotic
4-chloroindole [no description available]	2.11	1
alpha,beta-methyleneadenosine 5'-triphosphate alpha,beta-methyleneadenosine 5'-triphosphate: do not confuse with beta,gamma-methylene ATP; RN given refers to parent cpd	1.99	1	nucleoside triphosphate analogue
fosthiazate fosthiazate: structure in first source	2.07	1	organic phosphonate; organothiophosphate insecticide; phosphonic ester	agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; nematicide
pyrroline pyrroline: RN given refers to cpd with unspecified locant for dihydro moiety. pyrroline : Any organic heteromonocyclic compound with a structure based on a dihydropyrrole.	7.08	1	pyrroline
1-thiochromone [no description available]	2.1	1
6-bromoisatin 6-bromoisatin: anticancer compound from Dicathais orbita; structure in first source	8.33	6
allenolic acid allenolic acid: structure in first source	2.06	1	naphthols
3-hydroxy-3-phenacyloxindole [no description available]	7.13	1
combretastatin combretastatin: cytotoxic principle from South African tree COMBRETUM caffrum; structure given in first source; acts at COLCHICINE site of TUBULIN	2.13	1
4-chloroindole-3-acetic acid [no description available]	1.98	1	chloroindole-3-acetic acid	auxin
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.	2.99	4	cobalt group element atom; metal allergen	micronutrient
u 73122 1-(6-((3-methoxyestra-1,3,5(10)-trien-17-yl)amino)hexyl)-1H-pyrrole-2,5-dione: structure given in first source. U-73122 : An aza-steroid that is 3-O-methyl-17beta-estradiol in which the 17beta-hydroxy group is replaced by a 6-(maleimid-1-yl)hexylamino group. An inibitor of phospholipase C.	2.06	1	aromatic ether; aza-steroid; maleimides	EC 3.1.4.11 (phosphoinositide phospholipase C) inhibitor
paxilline paxilline: structure given in first source; RN given refers to (2R-(2alpha,4bbeta,6aalpha,12bbeta,12calpha,14abeta))-isomer. paxilline : An indole diterpene alkaloid with formula C27H33NO4 isolated from Penicillium paxilli. It is a potent inhibitor of large conductance Ca2(+)- and voltage-activated K(+) (BK)-type channels.	2.13	1	diterpene alkaloid; enone; organic heterohexacyclic compound; terpenoid indole alkaloid; tertiary alcohol	anticonvulsant; Aspergillus metabolite; EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor; genotoxin; geroprotector; mycotoxin; Penicillium metabolite; potassium channel blocker
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.	2.52	2	phosphite ion; trivalent inorganic anion
2'-5'-oligoadenylate trimer 2',5'-oligoadenylate: inhibits protein synthesis in cell-free systems	2.38	2
kt 5823 KT 5823: indolocarbazole; activates human neutrophils & fails to inhibit cGMP-dependent protein kinase phosphorylation of vimentin. KT 5823 : An organic heterooctacyclic compound that is 1H,1'H-2,2'-biindole in which the nitrogens have undergone formal oxidative coupling to positions 2 and 5 of methyl (3R)-3-methoxy-2-methyltetrahydrofuran-3-carboxylate (the 2S,3R,5R product), and in which the 3 and 3' positions of the biindole moiety have also undergone formal oxidative coupling to positions 3 and 4 of 1-methyl-1,5-dihydro-2H-pyrrol-2-one.	2.02	1	gamma-lactam; hemiaminal; indolocarbazole; methyl ester; organic heterooctacyclic compound	EC 2.7.11.12 (cGMP-dependent protein kinase) inhibitor
prolinamide prolinamide: RN given refers to cpd without isomeric designation. L-prolinamide : The carboxamide derivative of L-proline.	2.11	1	amino acid amide; L-proline derivative; pyrrolidinecarboxamide
1,3,4-thiadiazole 1,3,4-thiadiazole: structure given in first source	2.49	2	thiadiazole
benzyne benzyne: structure in first source. benzyne : 1,2-didehydrobenzene and its derivatives formed by substitution.	2.06	1	aryne; benzyne
stannane [no description available]	2.05	1	mononuclear parent hydride; tin hydride
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).	3.97	12	carbene; methanediyl
peroxynitrous acid Peroxynitrous Acid: A potent oxidant synthesized by the cell during its normal metabolism. Peroxynitrite is formed from the reaction of two free radicals, NITRIC OXIDE and the superoxide anion (SUPEROXIDES).	2.58	2	nitrogen oxoacid
1,3-indandione 1,2-indanedione: use for detection of latent fingerprints on porous surfaces; structure in first source	2.11	1
1-(1-(2-benzo(b)thienyl)cyclohexyl)piperidine 1-(1-(2-benzo(b)thienyl)cyclohexyl)piperidine: structure given in first source. 1-[1-(1-benzothiophen-2-yl)cyclohexyl]piperidine : A tertiary amino compound that consists of cyclohexane having piperidin-1-yl and benzothiophen-2-yl groups attached at position 1. A potent dopamine re-uptake inhibitor with a behavioral profile different from that of phencyclidine (PCP) and similar to that of cocaine.	2.06	1	1-benzothiophenes; piperidines; tertiary amino compound	dopamine uptake inhibitor
2,2'-pyridylisatogen tosylate 2,2'-pyridylisatogen tosylate: exerts inhibitory effect on action of ATP on smooth muscle; a P2Y1 purinoceptor antagonist; structure	4.95	12
safinamide safinamide: short-acting inhibitor of MOA-B; FCE 26743 is (S)-isomer, FCE 28073 is (R)-isomer; structure in first source	2.66	2	amino acid amide
quinone methide quinone methide: intermediate in eumelanin biosynthesis; structure given in first source. quinomethane : A methylidenecyclohexadienone, formally derived from a benzoquinone by replacement of one of the quinone oxygens by a methylidene group.	3.04	3	quinomethane
beta-lactams 2-azetidinone: structure in first source. azetidin-2-one : An unsubstituted beta-lactam compound.. beta-lactam : A lactam in which the amide bond is contained within a four-membered ring, which includes the amide nitrogen and the carbonyl carbon.	2.45	2	beta-lactam antibiotic allergen; beta-lactam
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.	3.63	9	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
tariquidar [no description available]	2.25	1	benzamides
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.	3.16	4	aromatic ether; cyclopropanes; fluoroquinolone antibiotic; pyrrolidinopiperidine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antibacterial drug
naproxen Naproxen: An anti-inflammatory agent with analgesic and antipyretic properties. Both the acid and its sodium salt are used in the treatment of rheumatoid arthritis and other rheumatic or musculoskeletal disorders, dysmenorrhea, and acute gout.. naproxen : A methoxynaphthalene that is 2-methoxynaphthalene substituted by a carboxy ethyl group at position 6. Naproxen is a non-steroidal anti-inflammatory drug commonly used for the reduction of pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, kidney stones, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis, bursitis, and for the treatment of primary dysmenorrhea. It works by inhibiting both the COX-1 and COX-2 enzymes.	2.31	1	methoxynaphthalene; monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; gout suppressant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	1.99	1	oxygen hydride; oxygen radical; reactive oxygen species
indium trichloride indium trichloride: RN given refers to parent cpd	2.07	1
fenton's reagent Fenton's reagent: used for oxidizing sugars & alcohols	1.99	1
aminoimidazole ribotide 5-amino-1-(5-phospho-beta-D-ribosyl)imidazole : A 1-(phosphoribosyl)imidazole that is 5-aminoimidazole in which the proton at position 1 has been replaced by a 5-phospho-beta-D-ribofuranosyl group.	2.21	1	1-(phosphoribosyl)imidazole; aminoimidazole	bacterial metabolite
isoindigotin isoindigotin: used in treatment of chronic granulocytic leukemia; structure given in first source	2.06	1
atropine tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate : A tropane alkaloid that is (1R,5)-8-methyl-8-azabicyclo[3.2.1]octane substituted by a (3-hydroxy-2-phenylpropanoyl)oxy group at position 3.	2.69	3
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	3.17	5	divalent inorganic anion; phosphite ion
spirobrassinin spirobrassinin: structure in first source	7.06	1
3-cyanoindole [no description available]	2.47	2
5-Fluoroisatin [no description available]	3.67	9	indoles	anticoronaviral agent
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	8.22	5
sodium bromide sodium bromide: RN given refers to parent cpd. sodium bromide : An inorganic sodium salt having bromide as the counterion.	2.05	1	bromide salt; inorganic sodium salt
withaferin a withaferin A: an antiestrogen and phytogenic antineoplastic agent isolated from leaves of Withania somnifera Dun.; structure. withaferin A : A withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 27 (the 4beta,5beta,6beta,22R stereoisomer). Isolated from Physalis longifolia, it exhibits cytotoxic activity.	2	1	27-hydroxy steroid; 4-hydroxy steroid; delta-lactone; enone; epoxy steroid; ergostanoid; primary alcohol; secondary alcohol; withanolide	antineoplastic agent; apoptosis inducer
u-104 SLC-0111: a carbonic anhydrase inhibitor; structure in first source	2.21	1
wortmannin [no description available]	2.06	1	acetate ester; cyclic ketone; delta-lactone; organic heteropentacyclic compound	anticoronaviral agent; antineoplastic agent; autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector; Penicillium metabolite; radiosensitizing agent
2-oxindole 2-oxindole: RN given refers to parent cpd; structure. indolin-2-one : An indolinone carrying an oxo group at position 2.	6.48	53	gamma-lactam; indolinone
indole-3-acetonitrile indole-3-acetonitrile: occurs in edible cruciferous vegetables. indole-3-acetonitrile : A nitrile that is acetonitrile where one of the methyl hydrogens is substituted by a 1H-indol-3-yl group.	2.06	1	indoles; nitrile	auxin; human xenobiotic metabolite; plant hormone; plant metabolite
glycogen glycogen : A polydisperse, highly branched glucan composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage, joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some cumulative alpha(1->6) links also may occur. The branches in glycogen typically contain 8 to 12 glucose residues.	2.66	3
bradykinin [no description available]	2.06	1	oligopeptide	human blood serum metabolite; vasodilator agent
meropenem Meropenem: A thienamycin derivative antibacterial agent that is more stable to renal dehydropeptidase I than IMIPENEM, but does not need to be given with an enzyme inhibitor such as CILASTATIN. It is used in the treatment of bacterial infections, including infections in immunocompromised patients.. meropenem : A carbapenemcarboxylic acid in which the azetidine and pyrroline rings carry 1-hydroxymethyl and in which the azetidine and pyrroline rings carry 1-hydroxymethyl and 5-(dimethylcarbamoyl)pyrrolidin-3-ylthio substituents respectively.	2.6	1	alpha,beta-unsaturated monocarboxylic acid; carbapenemcarboxylic acid; organic sulfide; pyrrolidinecarboxamide	antibacterial agent; antibacterial drug; drug allergen
indican [no description available]	7.03	1	beta-D-glucoside; exopolysaccharide; indolyl carbohydrate
sodium arsenite sodium arsenite : An inoganic sodium salt with formula with formula NaAsO2.	2.39	2	arsenic molecular entity; inorganic sodium salt	antibacterial agent; antifungal agent; antineoplastic agent; carcinogenic agent; herbicide; insecticide; rodenticide
ergosterol [no description available]	2	1	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; ergostanoid; phytosterols	fungal metabolite; Saccharomyces cerevisiae metabolite
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.	2.02	1	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
farnesol Farnesol: A colorless liquid extracted from oils of plants such as citronella, neroli, cyclamen, and tuberose. It is an intermediate step in the biological synthesis of cholesterol from mevalonic acid in vertebrates. It has a delicate odor and is used in perfumery. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). (2-trans,6-trans)-farnesol : The (2-trans,6-trans)-stereoisomer of farnesol.. farnesol : A farnesane sesquiterpenoid that is dodeca-2,6,10-triene substituted by methyl groups at positions 3, 7 and 11 and a hydroxy group at position 1.	2.02	1	farnesol	plant metabolite
tetragastrin Tetragastrin: L-Tryptophyl-L-methionyl-L-aspartyl-L-phenylalaninamide. The C-terminal tetrapeptide of gastrin. It is the smallest peptide fragment of gastrin which has the same physiological and pharmacological activity as gastrin.. tetragastrin : A tetrapeptide composed of L-tryptophan, L-methione, L-aspartic acid and L-phenylalaninamide residues joined in sequence.	2.03	1	peptidyl amide; tetrapeptide	anxiogenic; human metabolite
prostaglandin d2 Prostaglandin D2: The principal cyclooxygenase metabolite of arachidonic acid. It is released upon activation of mast cells and is also synthesized by alveolar macrophages. Among its many biological actions, the most important are its bronchoconstrictor, platelet-activating-factor-inhibitory, and cytotoxic effects.. prostaglandin D2 : A member of the class of prostaglandins D that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9 and 15 and an oxo group at position 11 (the 5Z,9alpha,13E,15S- stereoisomer).	2.45	2	prostaglandins D	human metabolite; mouse metabolite
zeatin Zeatin: An aminopurine factor in plant extracts that induces cell division. (Grant & Hackh's Chemical Dict, 5th ed)	1.98	1	zeatin	plant metabolite
h 89 N-(2-(4-bromocinnamylamino)ethyl)-5-isoquinolinesulfonamide: structure given in first source. N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide : A member of the class of isoquinolines that is the sulfonamide obtained by formal condensation of the sulfo group of isoquinoline-5-sulfonic acid with the primary amino group of N(1)-[3-(4-bromophenyl)prop-2-en-1-yl]ethane-1,2-diamine. It is a protein kinase A inhibitor.. (E)-N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide : A N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide in which the double bond adopts a trans-configuration.	2.06	1	N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide
imidazolidines [no description available]	2.84	3	azacycloalkane; imidazolidines; saturated organic heteromonocyclic parent
dactinomycin Dactinomycin: A compound composed of a two CYCLIC PEPTIDES attached to a phenoxazine that is derived from STREPTOMYCES parvullus. It binds to DNA and inhibits RNA synthesis (transcription), with chain elongation more sensitive than initiation, termination, or release. As a result of impaired mRNA production, protein synthesis also declines after dactinomycin therapy. (From AMA Drug Evaluations Annual, 1993, p2015)	1.98	1	actinomycin	mutagen
bms 433771 BMS 433771: a fusion inhibitor of respiratory syncytial virus; structure in first source	2.05	1
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.	2.03	1	one-carbon compound; organic sodium salt	antacid; food anticaking agent
oxazolidine oxazolidine: structure given in first source	7.55	2	oxazolidine
chalcone trans-chalcone : The trans-isomer of chalcone.	2.81	3	chalcone	EC 3.2.1.1 (alpha-amylase) inhibitor
isomethyleugenol Methylation: Addition of methyl groups. In histo-chemistry methylation is used to esterify carboxyl groups and remove sulfate groups by treating tissue sections with hot methanol in the presence of hydrochloric acid. (From Stedman, 25th ed)	3.2	5	isomethyleugenol
phenyl-n-tert-butylnitrone phenyl-N-tert-butylnitrone: a spin-trapping agent	1.99	1
1,4-diphenylbutadiene [no description available]	2.02	1	styrenes
4'-methoxychalcone 4'-methoxychalcone: RN given refers to compound with no isomeric designation	2.31	1	chalcones
arginine vasopressin Arginine Vasopressin: The predominant form of mammalian antidiuretic hormone. It is a nonapeptide containing an ARGININE at residue 8 and two disulfide-linked cysteines at residues of 1 and 6. Arg-vasopressin is used to treat DIABETES INSIPIDUS or to improve vasomotor tone and BLOOD PRESSURE.. argipressin : The predominant form of mammalian vasopressin (antidiuretic hormone). It is a nonapeptide containing an arginine at residue 8 and two disulfide-linked cysteines at residues of 1 and 6.	3.09	1	vasopressin	cardiovascular drug; hematologic agent; mitogen
acetyl-aspartyl-glutamyl-valyl-aspartal acetyl-aspartyl-glutamyl-valyl-aspartal: a capase inhibitor. Ac-Asp-Glu-Val-Asp-H : A tetrapeptide consisting of two L-aspartic acid residues, an L-glutamyl residue and an L-valine residue with an acetyl group at the N-terminal and with the C-terminal carboxy group reduced to an aldehyde. It is an inhibitor of caspase-3/7.	2.08	1	tetrapeptide	protease inhibitor
isopropyl thiogalactoside Isopropyl Thiogalactoside: A non-metabolizable galactose analog that induces expression of the LAC OPERON.. isopropyl beta-D-thiogalactopyranoside : An S-glycosyl compound consisting of beta-D-1-thiogalactose having an isopropyl group attached to the anomeric sulfur.	2.1	1	S-glycosyl compound
n(6)-cyclopentyladenosine [no description available]	2.02	1
7-diethylaminocoumarin-3-carboxylic acid [no description available]	2.06	1
methisazone Methisazone: An antiviral agent effective against pox viruses.	3.21	6
bemesetron [no description available]	2.06	1
isatin beta-thiosemicarbazone isatin beta-thiosemicarbazone: isatizon believed to be Russian synonym	4.71	30
2-mercaptobenzimidazole 2-mercaptobenzimidazole: purine synthesis antimetabolite; RN given refers to parent cpd	2.17	1
3-hydroxyquinolin-2(1h)-one 3-hydroxyquinolin-2(1H)-one: structure in first source. dihydroxyquinoline : Any hydroxyquinoline in which the number of hydroxy substituents is specified as two.	2.17	1	hydroxyquinoline; quinolone
7-methoxy-2-oxo-1-benzopyran-3-carboxylic acid ethyl ester [no description available]	2.06	1	coumarins
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.	8.11	4	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
rhodanine 2-mercaptothiazolinone: metabolite in urine from persons exposed to CS2; structure	7.17	1	thiazolidinone
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.	1.93	1	nucleobase analogue; thiocarbonyl compound	antithyroid drug; metabolite
4-aminostilbene 4-aminostilbene: RN given refers to cpd without isomeric designation	2.06	1
1-[(3,4-dichlorophenyl)methyl]indole-2,3-dione [no description available]	2.03	1	indoles
3-acetyl-7-methoxycoumarin 3-acetyl-7-methoxycoumarin: structure in first source	2.06	1	coumarins
thiosemicarbazide thiosemicarbazide: glutamate decarboxylase antagonist; structure given in first source. hydrazinecarbothioamide : A member of the class of thioureas that is thiourea in which a hydrogen of one of the amino groups is replaced by an amino group.	7	1	hydrazines; thiocarboxamide; thioureas
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.	3.91	12	one-carbon compound; thioureas; ureas	antioxidant; chromophore
indigo carmine Indigo Carmine: Indolesulfonic acid used as a dye in renal function testing for the detection of nitrates and chlorates, and in the testing of milk.. indigo carmine : An organic sodium salt resulting from the formal condensation of indigo carmine (acid form) with two equivalents of sodium hydroxide. It is an indicator at pH 11.5-14, changing from blue to yellow.	9.73	11
thiocarbohydrazide [no description available]	7.42	2	thiocarbonyl compound
ferric ferrocyanide ferric ferrocyanide: antidote to thallium poisoning; RN given refers to Fe(+3)[3:4] salt; structure	2.6	1
n-methyl-n-(tert-butyldimethylsilyl)trifluoroacetamide N-(tert-butyldimethylsilyl)-N-methyltrifluoroacetamide : An N-silyl compound that is N-methyltrifluoroacetamide in which the amide nitrogen is replaced by a tert-butyldimethylsilyl group.	1.97	1	monocarboxylic acid amide; N-silyl compound; trifluoroacetamide	chromatographic reagent
guanylthiourea Guanylthiourea: May protect against hypoxic damage; proposed for treatment of shock due to trauma or blood loss; also stimulates paretic gastrointestinal system.	1.95	1
nadp [no description available]	2.4	2
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	2.89	3
7-hydroxyindole [no description available]	7.46	2
6-Chlorobenzo[d]isoxazol-3-ol [no description available]	2.17	1	benzisoxazole
trisindoline trisindoline: an antibiotic indole trimer, produced by Vibrio separated from the marine sponge Hyrtios altum; structure given in first source	2.07	1
nsc73306 [no description available]	2.46	2
laccase Laccase: A copper-containing oxidoreductase enzyme that catalyzes the oxidation of 4-benzenediol to 4-benzosemiquinone. It also has activity towards a variety of O-quinols and P-quinols. It primarily found in FUNGI and is involved in LIGNIN degradation, pigment biosynthesis and detoxification of lignin-derived products.	2	1
quinine [no description available]	7.1	1	cinchona alkaloid	antimalarial; muscle relaxant; non-narcotic analgesic
methyldithiocarbazate methyldithiocarbazate: structure	7.6	1
sch 23390 SCH 23390: a selective D1-receptor antagonist. SCH 23390 : A benzazepine that is 2,3,4,5-tetrahydro-3-benzazepine bearing a phenyl substituent at position 1, a methyl substituent at position 3, a chloro substituent at position 7 and a hydroxy substituent at position 8.	2.06	1	benzazepine
rasagiline [no description available]	2.75	3	indanes; secondary amine; terminal acetylenic compound	EC 1.4.3.4 (monoamine oxidase) inhibitor; neuroprotective agent
2-(2-benzofuranyl)-2-imidazoline 2-(2-benzofuranyl)-2-imidazoline: structure given in first source	2	1	benzofurans
perophoramidine perophoramidine: from the Philippine ascidian Perophora namei; structure in first source	2.03	1
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	2.44	2
tert-butanesulfinamide tert-butanesulfinamide: structure in first source	2.1	1
sodium dodecyl sulfate Sodium Dodecyl Sulfate: An anionic surfactant, usually a mixture of sodium alkyl sulfates, mainly the lauryl; lowers surface tension of aqueous solutions; used as fat emulsifier, wetting agent, detergent in cosmetics, pharmaceuticals and toothpastes; also as research tool in protein biochemistry.. sodium dodecyl sulfate : An organic sodium salt that is the sodium salt of dodecyl hydrogen sulfate.	2.46	2	organic sodium salt	detergent; protein denaturant
alpha-chymotrypsin Chymotrypsin: A serine endopeptidase secreted by the pancreas as its zymogen, CHYMOTRYPSINOGEN and carried in the pancreatic juice to the duodenum where it is activated by TRYPSIN. It selectively cleaves aromatic amino acids on the carboxyl side.	2.46	2
7-deazapurine 7-deazapurine: structure in first source	7.6	1
17-ketosteroids 17-Ketosteroids: Steroids that contain a ketone group at position 17.. 17-oxo steroid : Any oxo steroid carrying the oxo group at position 17.	2.08	1
5-Nitroisatin [no description available]	3.3	6	indoles	anticoronaviral agent
quercetin [no description available]	1.96	1	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.	2.46	2	prostaglandins E	human metabolite; mouse metabolite; oxytocic
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	2.17	1	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
harmine Harmine: Alkaloid isolated from seeds of PEGANUM HARMALA; ZYGOPHYLLACEAE. It is identical to banisterine, or telepathine, from Banisteria caapi and is one of the active ingredients of hallucinogenic drinks made in the western Amazon region from related plants. It has no therapeutic use, but (as banisterine) was hailed as a cure for postencephalitic PARKINSON DISEASE in the 1920's.. harmine : A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7.	2.88	3	harmala alkaloid	anti-HIV agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; metabolite
humulene humulene: structure given in first source. (1E,4E,8E)-alpha-humulene : The (1E,4E,8E)-isomer of alpha-humulene.	1.98	1	alpha-humulene
dorzolamide dorzolamide: topically effective ocular hypotensive carbonic anhydrase inhibitor; RN refers to mono-HCl (4S-trans)-isomer. dorzolamide : 5,6-Dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide in which hydrogens at the 4 and 6 positions are substituted by ethylamino and methyl groups, respectively (4S, trans-configuration). A carbonic anhydrase inhibitor, it is used as the hydrochloride in ophthalmic solutions to lower increased intraocular pressure in the treatment of open-angle glaucoma and ocular hypertension.	3.41	1	sulfonamide; thiophenes	antiglaucoma drug; antihypertensive agent; EC 4.2.1.1 (carbonic anhydrase) inhibitor
naloxone Naloxone: A specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors.. naloxone : A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.	2.13	1	morphinane alkaloid; organic heteropentacyclic compound; tertiary alcohol	antidote to opioid poisoning; central nervous system depressant; mu-opioid receptor antagonist
morphine Meconium: The thick green-to-black mucilaginous material found in the intestines of a full-term fetus. It consists of secretions of the INTESTINAL GLANDS; BILE PIGMENTS; FATTY ACIDS; AMNIOTIC FLUID; and intrauterine debris. It constitutes the first stools passed by a newborn.	2.74	3	morphinane alkaloid; organic heteropentacyclic compound; tertiary amino compound	anaesthetic; drug allergen; environmental contaminant; geroprotector; mu-opioid receptor agonist; opioid analgesic; plant metabolite; vasodilator agent; xenobiotic
magnesium trisilicate magnesium trisilicate: RN given refers to parent cpd	2.08	1
12-hydroxy-5,8,10-heptadecatrienoic acid 12-hydroxy-5,8,10-heptadecatrienoic acid: metabolite of arachidonic acid in blood platelet suspension; RN given refers to cpd without isomeric designation	2.02	1	hydroxy polyunsaturated fatty acid; long-chain fatty acid; trienoic fatty acid	metabolite
su 11248 [no description available]	2.52	2	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
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	7.48	2	carbon group element atom; elemental lead; metal atom	neurotoxin
tin [no description available]	7.02	1	carbon group element atom; elemental tin; metal atom	micronutrient
8-(3-chlorostyryl)caffeine 8-(3-chlorostyryl)caffeine: adenosine antagonist. 8-(3-chlorostyryl)caffeine : Caffeine substituted at its 8-position by an (E)-3-chlorostyryl group.	2.05	1	monochlorobenzenes; trimethylxanthine	adenosine A2A receptor antagonist; EC 1.4.3.4 (monoamine oxidase) inhibitor
15-hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5,13-dienoic acid 15-Hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5,13-dienoic Acid: A stable prostaglandin endoperoxide analog which serves as a thromboxane mimetic. Its actions include mimicking the hydro-osmotic effect of VASOPRESSIN and activation of TYPE C PHOSPHOLIPASES. (From J Pharmacol Exp Ther 1983;224(1): 108-117; Biochem J 1984;222(1):103-110)	2.06	1
bismuth Bismuth: A metallic element that has the atomic symbol Bi, and atomic number 83. Its principal isotope is Bismuth 209.	2.31	1	metal atom; pnictogen
indium Indium: A metallic element, atomic number 49, atomic weight 114.818, symbol In. It is named from its blue line in the spectrum.. indium atom : A metallic element first identified and named from the brilliant indigo (Latin indicum) blue line in its flame spectrum.	3.31	6	boron group element atom
sulfur Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.	1.95	1	chalcogen; nonmetal atom	macronutrient
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.	2.66	3	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.	7.17	1	boron group element atom; metalloid atom; nonmetal atom	micronutrient
2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid 2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid: chromogen in glucose oxidase-peroxidase method for determining serum glucose; used in free radical scavenging assays; structure in first source	2.21	1
tetrodotoxin Tetrodotoxin: An aminoperhydroquinazoline poison found mainly in the liver and ovaries of fishes in the order TETRAODONTIFORMES, which are eaten. The toxin causes paresthesia and paralysis through interference with neuromuscular conduction.. tetrodotoxin : A quinazoline alkaloid that is a marine toxin isolated from fish such as puffer fish. It has been shown to exhibit potential neutotoxicity due to its ability to block voltage-gated sodium channels.	1.99	1	azatetracycloalkane; oxatetracycloalkane; quinazoline alkaloid	animal metabolite; bacterial metabolite; marine metabolite; neurotoxin; voltage-gated sodium channel blocker
allylsilane allylsilane: structure in first source	2.05	1
diphenyl phosphite diphenyl phosphite: a coupling agent for making sterically hindered peptide analogs; structure in first source	7.1	1
selenourea [no description available]	3.41	1
bambermycins Bambermycins: Antibiotic complex obtained from Streptomyces bambergiensis containing mainly Moenomycins A and C. They are used as feed additives and growth promoters for poultry, swine, and cattle.	2.1	1
4-oxo-2-nonenal 4-oxo-2-nonenal: reacts with 2'-deoxyguanosine; a product of lipid peroxidation; structure in first source. (E)-4-oxonon-2-enal : The enal that is (E)-non-2-enal substituted with an oxo group at C-4.	2.08	1	enal; enone	human metabolite
oxepins Oxepins: Compounds based on a 7-membered heterocyclic ring including an oxygen. They can be considered a medium ring ether. A natural source is the MONTANOA plant genus. Some dibenzo-dioxepins, called depsidones, are found in GARCINIA plants.	2.05	1
4-methyl-5-amino-1-formylisoquinoline thiosemicarbazone 4-methyl-5-amino-1-formylisoquinoline thiosemicarbazone: structure	2.05	1
mdl 201053 MDL 201053: Immunosuppressive Agent; RN given refers to compound with no isomeric designation	2.01	1
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.	4.47	23
thioacetazone Thioacetazone: A thiosemicarbazone that is used in association with other antimycobacterial agents in the initial and continuation phases of antituberculosis regimens. Thiacetazone containing regimens are less effective than the short-course regimen recommended by the International Union Against Tuberculosis and are used in some developing countries to reduce drug costs. (From Martindale, The Extra Pharmacopoeia, 30th ed, p217). thiosemicarbazone : A hydrazone resulting from the formal condensation of an aldehyde or ketone with the non-thioacylated nitrogen of thiosemicarbazide or its substituted derivatives.	2.05	1
3-aminopyridine-2-carboxaldehyde thiosemicarbazone 3-aminopyridine-2-carboxaldehyde thiosemicarbazone: a neuroprotective agent; structure given in first source	2.05	1
ag-041r AG-041R: structure in first source	2.11	1
sm 346 SM 346: 2-mercaptobenzimidazole derivative	2.6	1
mocetinostat mocetinostat: undergoing phase II clinical trials for treatment of cancer. mocetinostat : A benzamide obtained by formal condensation of the carboxy group of 4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid with one of the amino groups of benzene-1,2-diamine. It is an orally active and isotype-selective HDAC inhibitor which exhibits antitumour activity (IC50 = 0.15, 0.29, 1.66 and 0.59 muM for HDAC1, HDAC2, HDAC3 and HDAC11).	2.02	1	aminopyrimidine; benzamides; pyridines; secondary amino compound; secondary carboxamide; substituted aniline	antineoplastic agent; apoptosis inducer; autophagy inducer; cardioprotective agent; EC 3.5.1.98 (histone deacetylase) inhibitor; hepatotoxic agent
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.	2.04	1
680c91 680C91 : A fluoroindole that is 6-fluoroindole in which the hydrogen at position 3 has been replaced by a 2-(pyridin-3-yl)vinyl group (trans configuration). It is a selective inhibitor of tryptophan 2,3-dioxygenase (TDO), which directs the conversion of trypophan to kynurenin.	2.06	1	fluoroindole; olefinic compound; pyridines	EC 1.13.11.11 (tryptophan 2,3-dioxygenase) inhibitor
phosphoramidite phosphoramidite: structure in first source. phosphoramidite : A compound with the general formula (RO)2PNR2. Phosphoramidites can be regarded as phosphites that have an NR2 instead of an OH group, or as amides of phosphorous acid.	7.49	2
artenimol artenimol: derivative of antimalarial drug artemisinin (quinghaosu)	3.3	3
alpha-synuclein alpha-Synuclein: A synuclein that is a major component of LEWY BODIES and plays a role in SYNUCLEINOPATHIES, neurodegeneration and neuroprotection.	7.6	1
az10606120 AZ10606120: a P2X7 receptor antagonist	2.13	1
ningalin b ningalin B: structure in first source	2.25	1
oxadiazoles Oxadiazoles: Compounds containing five-membered heteroaromatic rings containing two carbons, two nitrogens, and one oxygen atom which exist in various regioisomeric forms.	9.11	4
ribose ribopyranose : The pyranose form of ribose.	3.06	1	D-ribose; ribopyranose
cobalt thiocyanate [no description available]	2.03	1
nutlin-3a nutlin 3: an MDM2 antagonist; structure in first source	2.61	2	stilbenoid
azastene azastene: inhibitor of ovarian & adrenal steroidogenesis in rats; progesterone antagonist	2.41	1
gliocladin c gliocladin C: structure in first source	2.06	1
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.	2.04	1
acid phosphatase Acid Phosphatase: An enzyme that catalyzes the conversion of an orthophosphoric monoester and water to an alcohol and orthophosphate. EC 3.1.3.2.	2.87	4
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	2.03	1	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
cytochrome c-t Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.	2.47	2
atrial natriuretic factor Atrial Natriuretic Factor: A potent natriuretic and vasodilatory peptide or mixture of different-sized low molecular weight PEPTIDES derived from a common precursor and secreted mainly by the HEART ATRIUM. All these peptides share a sequence of about 20 AMINO ACIDS.	5.22	9	polypeptide
ularitide Ularitide: a 32-amino acid peptide derived from (95-126 residues) of ANP PROHORMONE (1-126 residues); not biologically inactivated by a peptidase from dog kidney cortex membranes	1.99	1
brain natriuretic peptide, porcine brain natriuretic peptide, porcine: peptide made up of 32 amino acid residues; discovered in porcine brain and heart atria; BNP-26 is a synthetic analog of porcine brain natriuretic peptide	2	1
natriuretic peptide, c-type Natriuretic Peptide, C-Type: A PEPTIDE of 22 amino acids, derived mainly from cells of VASCULAR ENDOTHELIUM. It is also found in the BRAIN, major endocrine glands, and other tissues. It shares structural homology with ATRIAL NATRIURETIC FACTOR. It has vasorelaxant activity thus is important in the regulation of vascular tone and blood flow. Several high molecular weight forms containing the 22 amino acids have been identified.	2.69	3
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	2.11	1	glycoside
endothelin-1 Endothelin-1: A 21-amino acid peptide produced in a variety of tissues including endothelial and vascular smooth-muscle cells, neurons and astrocytes in the central nervous system, and endometrial cells. It acts as a modulator of vasomotor tone, cell proliferation, and hormone production. (N Eng J Med 1995;333(6):356-63)	2.06	1
chitosan [no description available]	3.11	4
sarkosyl sarkosyl: RN given is for sarkosyl L, the parent cpd; structure	2.02	1
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.	2.77	3
cyclopentylidene-[4-(4-chlorophenyl)thiazol-2-yl]hydrazone cyclopentylidene-[4-(4-chlorophenyl)thiazol-2-yl]hydrazone : A member of the class of 1,3-thiazole bearing 2-cyclopentylidenehydrazino and 4-chlorophenyl substituents at positions 2 and 4 respectively.	2.05	1	1,3-thiazoles; hydrazone; monochlorobenzenes	EC 2.3.1.48 (histone acetyltransferase) inhibitor
piperidines Piperidines: A family of hexahydropyridines.	2.06	1
madindoline a madindoline A: inhibits interleukin-6; isolated from Streptomyces; structure in first source	7.05	1
interleukin-8 Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.	2.02	1
communesin b communesin B: from ethyl acetate extract of Penicillium sp., derived from the Mediterranean sponge Axinella verrucosa; structure in first source	2.03	1
vasoactive intestinal peptide Vasoactive Intestinal Peptide: A highly basic, 28 amino acid neuropeptide released from intestinal mucosa. It has a wide range of biological actions affecting the cardiovascular, gastrointestinal, and respiratory systems and is neuroprotective. It binds special receptors (RECEPTORS, VASOACTIVE INTESTINAL PEPTIDE).	1.96	1
natriuretic peptide, brain Natriuretic Peptide, Brain: A PEPTIDE that is secreted by the BRAIN and the HEART ATRIA, stored mainly in cardiac ventricular MYOCARDIUM. It can cause NATRIURESIS; DIURESIS; VASODILATION; and inhibits secretion of RENIN and ALDOSTERONE. It improves heart function. It contains 32 AMINO ACIDS.	2.93	4	polypeptide
crotylsilane crotylsilane: structure in first source	2.03	1
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	1.95	1	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
salicylates Salicylates: The salts or esters of salicylic acids, or salicylate esters of an organic acid. Some of these have analgesic, antipyretic, and anti-inflammatory activities by inhibiting prostaglandin synthesis.. hydroxybenzoate : Any benzoate derivative carrying a single carboxylate group and at least one hydroxy substituent.. salicylates : Any salt or ester arising from reaction of the carboxy group of salicylic acid, or any ester resulting from the condensation of the phenolic hydroxy group of salicylic acid with an organic acid.. salicylate : A monohydroxybenzoate that is the conjugate base of salicylic acid.	1.95	1	monohydroxybenzoate	plant metabolite
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	3.09	4	benzenes; hydroxycoumarin; methyl ketone
4-hydroxycoumarin 2-hydroxychromone: structure	2.05	1	hydroxycoumarin
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.	2.08	1	aluminosilicate mineral; mixture	antidiarrhoeal drug; excipient
monosulfuron monosulfuron: structure in first source	2.06	1
2-fluoroethylazide 2-fluoroethylazide: used for click labeling; structure in first source	2.04	1
benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone: an interleukin-1beta converting enzyme (ICE)-like protease inhibitor	2.41	2
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	1.97	1
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.	2.36	2
beta-isocupreidine beta-isocupreidine: structure in first source	2.49	2
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.	2.31	1
amyloid beta-peptides amyloid beta-protein (1-40): although acutely neurotoxic in both rat & monkey cerebral cortex, neuronal degeneration in primates resembles more closely to that found in Alzheimer's disease; amino acid sequence has been determined	2.63	2
cyclic gmp Cyclic GMP: Guanosine cyclic 3',5'-(hydrogen phosphate). A guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger. Its levels increase in response to a variety of hormones, including acetylcholine, insulin, and oxytocin and it has been found to activate specific protein kinases. (From Merck Index, 11th ed). 3',5'-cyclic GMP : A 3',5'-cyclic purine nucleotide in which the purine nucleobase is specified as guanidine.	8.28	6	3',5'-cyclic purine nucleotide; guanyl ribonucleotide	Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
rifampin Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)	2.41	2	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
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.	2.73	3	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
thiolactomycin thiolactomycin: from actinomycetes; structure given in first source	2.05	1
pyrimidinones Pyrimidinones: Heterocyclic compounds known as 2-pyrimidones (or 2-hydroxypyrimidines) and 4-pyrimidones (or 4-hydroxypyrimidines) with the general formula C4H4N2O.	2.78	3

Condition	Relationship Strength	Studies
Plasmodium falciparum Malaria [description not available]	2.05	1
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.	2.05	1
Innate Inflammatory Response [description not available]	3.64	9
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.	8.64	9
Germinoblastoma [description not available]	2.75	3
Lymphoma A general term for various neoplastic diseases of the lymphoid tissue.	2.75	3
Benign Neoplasms [description not available]	6.61	23
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.	6.61	23
Leukemia, Lymphocytic, T Cell [description not available]	2.13	1
Leukemia, T-Cell A malignant disease of the T-LYMPHOCYTES in the bone marrow, thymus, and/or blood.	2.13	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.94	4
Neuroblastoma A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)	3.82	10
Cystic Fibrosis of Pancreas [description not available]	2.41	1
Infections, Pseudomonas [description not available]	2.41	1
Cystic Fibrosis An autosomal recessive genetic disease of the EXOCRINE GLANDS. It is caused by mutations in the gene encoding the CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR expressed in several organs including the LUNG, the PANCREAS, the BILIARY SYSTEM, and the SWEAT GLANDS. Cystic fibrosis is characterized by epithelial secretory dysfunction associated with ductal obstruction resulting in AIRWAY OBSTRUCTION; chronic RESPIRATORY INFECTIONS; PANCREATIC INSUFFICIENCY; maldigestion; salt depletion; and HEAT PROSTRATION.	2.41	1
Pseudomonas Infections Infections with bacteria of the genus PSEUDOMONAS.	2.41	1
Idiopathic Parkinson Disease [description not available]	5.02	9
Parkinson Disease A progressive, degenerative neurologic disease characterized by a TREMOR that is maximal at rest, retropulsion (i.e. a tendency to fall backwards), rigidity, stooped posture, slowness of voluntary movements, and a masklike facial expression. Pathologic features include loss of melanin containing neurons in the substantia nigra and other pigmented nuclei of the brainstem. LEWY BODIES are present in the substantia nigra and locus coeruleus but may also be found in a related condition (LEWY BODY DISEASE, DIFFUSE) characterized by dementia in combination with varying degrees of parkinsonism. (Adams et al., Principles of Neurology, 6th ed, p1059, pp1067-75)	5.02	9
Alcohol Withdrawal Associated Autonomic Hyperactivity [description not available]	1.96	1
Alcohol Abuse [description not available]	3.3	2
Alcohol Drinking Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.	2.38	2
Alcoholism A primary, chronic disease with genetic, psychosocial, and environmental factors influencing its development and manifestations. The disease is often progressive and fatal. It is characterized by impaired control over drinking, preoccupation with the drug alcohol, use of alcohol despite adverse consequences, and distortions in thinking, most notably denial. Each of these symptoms may be continuous or periodic. (Morse & Flavin for the Joint Commission of the National Council on Alcoholism and Drug Dependence and the American Society of Addiction Medicine to Study the Definition and Criteria for the Diagnosis of Alcoholism: in JAMA 1992;268:1012-4)	3.3	2
Anxiety Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.	10.64	13
Drug Withdrawal Symptoms [description not available]	1.98	1
Substance Withdrawal Syndrome Physiological and psychological symptoms associated with withdrawal from the use of a drug after prolonged administration or habituation. The concept includes withdrawal from smoking or drinking, as well as withdrawal from an administered drug.	1.98	1
Alloxan Diabetes [description not available]	2.44	2
Absence Seizure [description not available]	4.62	10
Seizures Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.	9.62	10
Aggression Behavior which may be manifested by destructive and attacking action which is verbal or physical, by covert attitudes of hostility or by obstructionism.	1.97	1
Abdominal Migraine [description not available]	2.38	2
Acute Disease Disease having a short and relatively severe course.	2.4	2
Migraine Disorders A class of disabling primary headache disorders, characterized by recurrent unilateral pulsatile headaches. The two major subtypes are common migraine (without aura) and classic migraine (with aura or neurological symptoms). (International Classification of Headache Disorders, 2nd ed. Cephalalgia 2004: suppl 1)	2.38	2
Anasarca [description not available]	3.3	6
Allodynia [description not available]	2.43	2
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	3.3	6
Bilateral Headache [description not available]	1.97	1
Headache The symptom of PAIN in the cranial region. It may be an isolated benign occurrence or manifestation of a wide variety of HEADACHE DISORDERS.	1.97	1
Nervous System Disorders [description not available]	2.37	2
Nervous System Diseases Diseases of the central and peripheral nervous system. This includes disorders of the brain, spinal cord, cranial nerves, peripheral nerves, nerve roots, autonomic nervous system, neuromuscular junction, and muscle.	2.37	2
Aura [description not available]	3.84	4
Epilepsy A disorder characterized by recurrent episodes of paroxysmal brain dysfunction due to a sudden, disorderly, and excessive neuronal discharge. Epilepsy classification systems are generally based upon: (1) clinical features of the seizure episodes (e.g., motor seizure), (2) etiology (e.g., post-traumatic), (3) anatomic site of seizure origin (e.g., frontal lobe seizure), (4) tendency to spread to other structures in the brain, and (5) temporal patterns (e.g., nocturnal epilepsy). (From Adams et al., Principles of Neurology, 6th ed, p313)	3.84	4
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	3.3	2
Acute Post-Traumatic Stress Disorder [description not available]	3.3	2
Combat Disorders Neurotic reactions to unusual, severe, or overwhelming military stress.	1.97	1
Stress Disorders, Post-Traumatic A class of traumatic stress disorders with symptoms that last more than one month.	3.3	2
Cancer of Liver [description not available]	2.81	3
Liver Neoplasms Tumors or cancer of the LIVER.	2.81	3
Breast Cancer [description not available]	5.48	13
Breast Neoplasms Tumors or cancer of the human BREAST.	5.48	13
Bacterial Disease [description not available]	4.15	4
Bacterial Infections Infections by bacteria, general or unspecified.	4.15	4
Adenocarcinoma, Basal Cell [description not available]	2.41	1
Colorectal Cancer [description not available]	7.82	3
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	2.41	1
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	2.82	3
Diabetes Mellitus A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.	2.41	1
Koch's Disease [description not available]	2.53	2
Tuberculosis Any of the infectious diseases of man and other animals caused by species of MYCOBACTERIUM TUBERCULOSIS.	7.53	2
Cerebral Malaria [description not available]	2.6	1
Adjuvant Arthritis [description not available]	2.41	1
Rheumatoid Arthritis [description not available]	7.41	1
Arthritis, Rheumatoid A chronic systemic disease, primarily of the joints, marked by inflammatory changes in the synovial membranes and articular structures, widespread fibrinoid degeneration of the collagen fibers in mesenchymal tissues, and by atrophy and rarefaction of bony structures. Etiology is unknown, but autoimmune mechanisms have been implicated.	2.41	1
Autosomal Dominant Juvenile Parkinson Disease [description not available]	4.55	8
Parkinsonian Disorders A group of disorders which feature impaired motor control characterized by bradykinesia, MUSCLE RIGIDITY; TREMOR; and postural instability. Parkinsonian diseases are generally divided into primary parkinsonism (see PARKINSON DISEASE), secondary parkinsonism (see PARKINSON DISEASE, SECONDARY) and inherited forms. These conditions are associated with dysfunction of dopaminergic or closely related motor integration neuronal pathways in the BASAL GANGLIA.	4.55	8
Nerve Pain [description not available]	2.52	2
Neuralgia Intense or aching pain that occurs along the course or distribution of a peripheral or cranial nerve.	2.52	2
Acute Confusional Senile Dementia [description not available]	3.61	7
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)	3.61	7
2019 Novel Coronavirus Disease [description not available]	2.6	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	4.15	15
Cancer of Ovary [description not available]	2.82	2
Ovarian Neoplasms Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.	2.82	2
Carcinoma, Ehrlich Tumor A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.	2.58	2
Ascites Accumulation or retention of free fluid within the peritoneal cavity.	2.21	1
Degenerative Diseases, Central Nervous System [description not available]	2.57	2
Neurodegenerative Diseases Hereditary and sporadic conditions which are characterized by progressive nervous system dysfunction. These disorders are often associated with atrophy of the affected central or peripheral nervous system structures.	2.57	2
Invasiveness, Neoplasm [description not available]	2.89	3
Diabetes Mellitus, Adult-Onset [description not available]	2.31	1
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	2.31	1
Leishmania Infection [description not available]	2.31	1
Leishmaniasis A disease caused by any of a number of species of protozoa in the genus LEISHMANIA. There are four major clinical types of this infection: cutaneous (Old and New World) (LEISHMANIASIS, CUTANEOUS), diffuse cutaneous (LEISHMANIASIS, DIFFUSE CUTANEOUS), mucocutaneous (LEISHMANIASIS, MUCOCUTANEOUS), and visceral (LEISHMANIASIS, VISCERAL).	2.31	1
Palmoplantaris Pustulosis [description not available]	2.31	1
Psoriasis A common genetically determined, chronic, inflammatory skin disease characterized by rounded erythematous, dry, scaling patches. The lesions have a predilection for nails, scalp, genitalia, extensor surfaces, and the lumbosacral region. Accelerated epidermopoiesis is considered to be the fundamental pathologic feature in psoriasis.	2.31	1
Herpes Simplex Virus Infection [description not available]	2.31	1
Herpes Simplex A group of acute infections caused by herpes simplex virus type 1 or type 2 that is characterized by the development of one or more small fluid-filled vesicles with a raised erythematous base on the skin or mucous membrane. It occurs as a primary infection or recurs due to a reactivation of a latent infection. (Dorland, 27th ed.)	2.31	1
Cancer of Colon [description not available]	3.14	4
Colonic Neoplasms Tumors or cancer of the COLON.	3.14	4
Malignant Melanoma [description not available]	2.31	1
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	2.31	1
MPTP Neurotoxicity Syndrome [description not available]	2.15	1
Metastase [description not available]	2.58	2
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	2.58	2
Experimental Neoplasms [description not available]	3.72	3
Colitis Gravis [description not available]	2.17	1
Colitis, Ulcerative Inflammation of the COLON that is predominantly confined to the MUCOSA. Its major symptoms include DIARRHEA, rectal BLEEDING, the passage of MUCUS, and ABDOMINAL PAIN.	2.17	1
Arbovirus Infections Infections caused by arthropod-borne viruses, general or unspecified.	3.12	1
ER-Negative PR-Negative HER2-Negative Breast Cancer [description not available]	2.57	2
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.	2.57	2
Food Poisoning [description not available]	2.17	1
Parasite Infections [description not available]	2.17	1
Sexually Transmitted Diseases Diseases due to or propagated by sexual contact.	2.17	1
Acute Myelogenous Leukemia [description not available]	2.25	1
Leukemia, Myeloid, Acute Clonal expansion of myeloid blasts in bone marrow, blood, and other tissue. Myeloid leukemias develop from changes in cells that normally produce NEUTROPHILS; BASOPHILS; EOSINOPHILS; and MONOCYTES.	2.25	1
Granulocytic Leukemia, Chronic [description not available]	2.08	1
Leukemia, Myelogenous, Chronic, BCR-ABL Positive Clonal hematopoetic disorder caused by an acquired genetic defect in PLURIPOTENT STEM CELLS. It starts in MYELOID CELLS of the bone marrow, invades the blood and then other organs. The condition progresses from a stable, more indolent, chronic phase (LEUKEMIA, MYELOID, CHRONIC PHASE) lasting up to 7 years, to an advanced phase composed of an accelerated phase (LEUKEMIA, MYELOID, ACCELERATED PHASE) and BLAST CRISIS.	2.08	1
Cancer of Lung [description not available]	2.44	2
Lung Neoplasms Tumors or cancer of the LUNG.	2.44	2
Chromosome-Defective Micronuclei [description not available]	2.08	1
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	7.75	3
Colitis Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.	7.1	1
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.08	1
Vaccinia The cutaneous and occasional systemic reactions associated with vaccination using smallpox (variola) vaccine.	3.55	9
Blood Pressure, High [description not available]	2.11	1
Hypertension Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.	2.11	1
Ache [description not available]	2.8	3
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	2.8	3
Infections, Trichomonas [description not available]	2.11	1
Trichomonas Infections Infections in birds and mammals produced by various species of Trichomonas.	2.11	1
Apoplexy [description not available]	2.13	1
Stroke A group of pathological conditions characterized by sudden, non-convulsive loss of neurological function due to BRAIN ISCHEMIA or INTRACRANIAL HEMORRHAGES. Stroke is classified by the type of tissue NECROSIS, such as the anatomic location, vasculature involved, etiology, age of the affected individual, and hemorrhagic vs. non-hemorrhagic nature. (From Adams et al., Principles of Neurology, 6th ed, pp777-810)	2.13	1
Injury, Myocardial Reperfusion [description not available]	2.45	2
Cytomegalovirus A genus of the family HERPESVIRIDAE, subfamily BETAHERPESVIRINAE, infecting the salivary glands, liver, spleen, lungs, eyes, and other organs, in which they produce characteristically enlarged cells with intranuclear inclusions. Infection with Cytomegalovirus is also seen as an opportunistic infection in AIDS.	2.11	1
Extravascular Hemolysis [description not available]	2.4	2
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	2.4	2
Hepatocellular Carcinoma [description not available]	2.53	2
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	2.53	2
Insulin Sensitivity [description not available]	2.13	1
Insulin Resistance Diminished effectiveness of INSULIN in lowering blood sugar levels: requiring the use of 200 units or more of insulin per day to prevent HYPERGLYCEMIA or KETOSIS.	2.13	1
HIV Coinfection [description not available]	2.5	2
HIV Infections Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).	2.5	2
Acute Promyelocytic Leukemia [description not available]	2.05	1
Leukemia, Promyelocytic, Acute An acute myeloid leukemia in which abnormal PROMYELOCYTES predominate. It is frequently associated with DISSEMINATED INTRAVASCULAR COAGULATION.	2.05	1
Asthma, Bronchial [description not available]	2.05	1
Asthma A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL).	7.05	1
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.	3.98	14
Injury, Ischemia-Reperfusion [description not available]	2.06	1
Reperfusion Injury Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.	2.06	1
Atherogenesis [description not available]	2.06	1
Atherosclerosis A thickening and loss of elasticity of the walls of ARTERIES that occurs with formation of ATHEROSCLEROTIC PLAQUES within the ARTERIAL INTIMA.	2.06	1
Female Genital Neoplasms [description not available]	2.07	1
Genital Neoplasms, Female Tumor or cancer of the female reproductive tract (GENITALIA, FEMALE).	2.07	1
Cardiovascular Stroke [description not available]	2.01	1
Heart Disease, Ischemic [description not available]	2.01	1
Myocardial Infarction NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).	2.01	1
Myocardial Ischemia A disorder of cardiac function caused by insufficient blood flow to the muscle tissue of the heart. The decreased blood flow may be due to narrowing of the coronary arteries (CORONARY ARTERY DISEASE), to obstruction by a thrombus (CORONARY THROMBOSIS), or less commonly, to diffuse narrowing of arterioles and other small vessels within the heart. Severe interruption of the blood supply to the myocardial tissue may result in necrosis of cardiac muscle (MYOCARDIAL INFARCTION).	2.01	1
Bradykinesia [description not available]	2.42	2
Acquired Immune Deficiency Syndrome [description not available]	2.93	1
Acquired Immunodeficiency Syndrome An acquired defect of cellular immunity associated with infection by the human immunodeficiency virus (HIV), a CD4-positive T-lymphocyte count under 200 cells/microliter or less than 14% of total lymphocytes, and increased susceptibility to opportunistic infections and malignant neoplasms. Clinical manifestations also include emaciation (wasting) and dementia. These elements reflect criteria for AIDS as defined by the CDC in 1993.	2.93	1
Amelia [description not available]	2.34	2
Viral Diseases [description not available]	2.34	2
Virus Diseases A general term for diseases caused by viruses.	2.34	2
Alastrim [description not available]	1.93	1
Smallpox An acute, highly contagious, often fatal infectious disease caused by an orthopoxvirus characterized by a biphasic febrile course and distinctive progressive skin eruptions. Vaccination has succeeded in eradicating smallpox worldwide. (Dorland, 28th ed)	1.93	1
Hypogammaglobulinemia [description not available]	1.93	1
Agammaglobulinemia An immunologic deficiency state characterized by an extremely low level of generally all classes of gamma-globulin in the blood.	1.93	1
Ectromelia, Infectious A viral infection of mice, causing edema and necrosis followed by limb loss.	1.93	1
Brain Inflammation [description not available]	2.35	2
Encephalitis Inflammation of the BRAIN due to infection, autoimmune processes, toxins, and other conditions. Viral infections (see ENCEPHALITIS, VIRAL) are a relatively frequent cause of this condition.	2.35	2
Leucocythaemia [description not available]	2.43	2
Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)	2.43	2
Encephalopathy, Toxic [description not available]	2.02	1
Anoxemia [description not available]	2.02	1
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	2.02	1
Anaplastic Astrocytoma [description not available]	2.02	1
Astrocytoma Neoplasms of the brain and spinal cord derived from glial cells which vary from histologically benign forms to highly anaplastic and malignant tumors. Fibrillary astrocytomas are the most common type and may be classified in order of increasing malignancy (grades I through IV). In the first two decades of life, astrocytomas tend to originate in the cerebellar hemispheres; in adults, they most frequently arise in the cerebrum and frequently undergo malignant transformation. (From Devita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2013-7; Holland et al., Cancer Medicine, 3d ed, p1082)	2.02	1
Arrhythmia [description not available]	2.02	1
Arrhythmias, Cardiac Any disturbances of the normal rhythmic beating of the heart or MYOCARDIAL CONTRACTION. Cardiac arrhythmias can be classified by the abnormalities in HEART RATE, disorders of electrical impulse generation, or impulse conduction.	2.02	1
AIDS-Related Opportunistic Infections Opportunistic infections found in patients who test positive for human immunodeficiency virus (HIV). The most common include PNEUMOCYSTIS PNEUMONIA, Kaposi's sarcoma, cryptosporidiosis, herpes simplex, toxoplasmosis, cryptococcosis, and infections with Mycobacterium avium complex, Microsporidium, and Cytomegalovirus.	2.02	1
HIV Human immunodeficiency virus. A non-taxonomic and historical term referring to any of two species, specifically HIV-1 and/or HIV-2. Prior to 1986, this was called human T-lymphotropic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV). From 1986-1990, it was an official species called HIV. Since 1991, HIV was no longer considered an official species name; the two species were designated HIV-1 and HIV-2.	7.4	2
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	2.41	2
Disease, Pulmonary [description not available]	2.04	1
Edema, Pulmonary [description not available]	2.04	1
Lung Diseases Pathological processes involving any part of the LUNG.	2.04	1
Pulmonary Edema Excessive accumulation of extravascular fluid in the lung, an indication of a serious underlying disease or disorder. Pulmonary edema prevents efficient PULMONARY GAS EXCHANGE in the PULMONARY ALVEOLI, and can be life-threatening.	2.04	1
Muscle Relaxation That phase of a muscle twitch during which a muscle returns to a resting position.	2.65	3
Binge Eating [description not available]	1.98	1
Bulimia Eating an excess amount of food in a short period of time, as seen in the disorder of BULIMIA NERVOSA. It is caused by an abnormal craving for food, or insatiable hunger also known as ox hunger.	6.98	1
Depression, Endogenous [description not available]	2.9	1
Depressive Disorder An affective disorder manifested by either a dysphoric mood or loss of interest or pleasure in usual activities. The mood disturbance is prominent and relatively persistent.	2.9	1
Chromosomal Translocation [description not available]	1.98	1
Nerve Degeneration Loss of functional activity and trophic degeneration of nerve axons and their terminal arborizations following the destruction of their cells of origin or interruption of their continuity with these cells. The pathology is characteristic of neurodegenerative diseases. Often the process of nerve degeneration is studied in research on neuroanatomical localization and correlation of the neurophysiology of neural pathways.	2.9	1
Alveolar Echinococcosis, Hepatic [description not available]	1.98	1
Anxiety Neuroses [description not available]	1.98	1
Age-Related Memory Disorders [description not available]	1.98	1
Anxiety Disorders Persistent and disabling ANXIETY.	1.98	1
Memory Disorders Disturbances in registering an impression, in the retention of an acquired impression, or in the recall of an impression. Memory impairments are associated with DEMENTIA; CRANIOCEREBRAL TRAUMA; ENCEPHALITIS; ALCOHOLISM (see also ALCOHOL AMNESTIC DISORDER); SCHIZOPHRENIA; and other conditions.	1.98	1
Brain Vascular Disorders [description not available]	1.98	1
Cerebrovascular Disorders A spectrum of pathological conditions of impaired blood flow in the brain. They can involve vessels (ARTERIES or VEINS) in the CEREBRUM, the CEREBELLUM, and the BRAIN STEM. Major categories include INTRACRANIAL ARTERIOVENOUS MALFORMATIONS; BRAIN ISCHEMIA; CEREBRAL HEMORRHAGE; and others.	1.98	1
Bilharziasis [description not available]	1.99	1
Schistosomiasis Infection with flukes (trematodes) of the genus SCHISTOSOMA. Three species produce the most frequent clinical diseases: SCHISTOSOMA HAEMATOBIUM (endemic in Africa and the Middle East), SCHISTOSOMA MANSONI (in Egypt, northern and southern Africa, some West Indies islands, northern 2/3 of South America), and SCHISTOSOMA JAPONICUM (in Japan, China, the Philippines, Celebes, Thailand, Laos). S. mansoni is often seen in Puerto Ricans living in the United States.	1.99	1
Behavior Disorders [description not available]	2.91	1
Mental Disorders Psychiatric illness or diseases manifested by breakdowns in the adaptational process expressed primarily as abnormalities of thought, feeling, and behavior producing either distress or impairment of function.	2.91	1
Leukemia L 1210 [description not available]	2.91	1
Pyrexia [description not available]	2.7	3
Fever An abnormal elevation of body temperature, usually as a result of a pathologic process.	2.7	3
Arthritis, Degenerative [description not available]	2	1
Osteoarthritis A progressive, degenerative joint disease, the most common form of arthritis, especially in older persons. The disease is thought to result not from the aging process but from biochemical changes and biomechanical stresses affecting articular cartilage. In the foreign literature it is often called osteoarthrosis deformans.	2	1
Enterovirus Infections Diseases caused by ENTEROVIRUS.	2.36	2
Cell Transformation, Neoplastic Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.	2.36	2
Experimental Leukemia [description not available]	1.95	1
Cell Transformation, Viral An inheritable change in cells manifested by changes in cell division and growth and alterations in cell surface properties. It is induced by infection with a transforming virus.	1.95	1
Fowl Paralysis [description not available]	1.95	1
Coronary Heart Disease [description not available]	1.95	1
Coronary Disease An imbalance between myocardial functional requirements and the capacity of the CORONARY VESSELS to supply sufficient blood flow. It is a form of MYOCARDIAL ISCHEMIA (insufficient blood supply to the heart muscle) caused by a decreased capacity of the coronary vessels.	1.95	1
Hemorrhagic Fevers, Viral A group of viral diseases of diverse etiology but having many similar clinical characteristics; increased capillary permeability, leukopenia, and thrombocytopenia are common to all. Hemorrhagic fevers are characterized by sudden onset, fever, headache, generalized myalgia, backache, conjunctivitis, and severe prostration, followed by various hemorrhagic symptoms. Hemorrhagic fever with kidney involvement is HEMORRHAGIC FEVER WITH RENAL SYNDROME.	1.95	1
Abscess, Amebic [description not available]	1.95	1
Amebiasis Infection with any of various amebae. It is an asymptomatic carrier state in most individuals, but diseases ranging from chronic, mild diarrhea to fulminant dysentery may occur.	1.95	1
Acute Liver Injury, Drug-Induced [description not available]	2.35	2
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	2.35	2
Chromosome Deletion Actual loss of portion of a chromosome.	1.97	1
Infections, Togaviridae [description not available]	1.96	1
Cystic Echinococcosis [description not available]	1.97	1
Chronic Illness [description not available]	1.95	1
Bile Duct Obstruction [description not available]	1.95	1
Cirrhosis, Liver [description not available]	1.95	1
Cholestasis Impairment of bile flow due to obstruction in small bile ducts (INTRAHEPATIC CHOLESTASIS) or obstruction in large bile ducts (EXTRAHEPATIC CHOLESTASIS).	1.95	1
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	1.95	1
Liver Cirrhosis Liver disease in which the normal microcirculation, the gross vascular anatomy, and the hepatic architecture have been variably destroyed and altered with fibrous septa surrounding regenerated or regenerating parenchymal nodules.	1.95	1

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