indoline profile

Indoline is a bicyclic aromatic heterocycle consisting of a benzene ring fused to a pyrrolidine ring. It is a colorless liquid with a characteristic amine-like odor. Indoline is a versatile building block in organic synthesis and finds applications in various fields, including pharmaceuticals, agrochemicals, and materials science. It serves as a precursor to various biologically active compounds and is involved in the synthesis of indole alkaloids, such as strychnine and reserpine. Indoline derivatives exhibit a wide range of pharmacological activities, including anti-inflammatory, analgesic, antidepressant, and anticancer properties. Furthermore, indoline derivatives have shown promise as potential therapeutic agents for neurodegenerative diseases, such as Alzheimer's disease. '

indoline: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	10328
CHEMBL ID	388803
CHEBI ID	43295
SCHEMBL ID	5629
MeSH ID	M0161583

Synonym
BIDD:GT0113
AC-531
dihydroindole
5-20-06-00238 (beilstein handbook reference)
unii-6dpt9ab2nk
6dpt9ab2nk ,
1h-indole, 2,3-dihydro-
indoline
brn 0111915
einecs 207-816-8
1-azaindan
ai3-39164
2,3-dihydro-1h-indole
AG-690/11351758
2,3-dihydroindole
496-15-1
inchi=1/c8h9n/c1-2-4-8-7(3-1)5-6-9-8/h1-4,9h,5-6h
indoline, reagentplus(r), 99%
CHEBI:43295 ,
STK182863
CHEMBL388803
I0033
AKOS000119725
A22086
BBL004502
indoline, 19
bdbm92697
FT-0627227
SCHEMBL5629
PS-5755
DTXSID9052133
2,3-dihydro-1 h-indole
aza-indane
AM85791
indole, 2,3-dihydro-
1h-indole, dihydro-
mfcd00005705
azaindane
CS-W009145
F2190-0413
indoline, purum, >=98.0% (gc)
indoline, vetec(tm) reagent grade, 98%
Q2613101
SY012760
indoline-
P19974
SB66078
(2,4-dimethylphenyl)thio]aceticacid
EN300-19816
Z104475582

Excerpt	Reference	Relevance
"The indoline is a scaffold with significantly less historical studies and FDA-approved drugs and it has attracted new interest in drug design and development."	( Indole and Indoline Scaffolds in Antimicrobials: Overview, Synthesis and Recent Advances in Antimicrobial Research. Lupton, HK; Nieto, MJ, 2021)	1.49

Excerpt	Reference	Relevance
"Indoline has been reported as an efficient anticancer fragment to design novel anticancer agents."	( Discovery of indoline derivatives as anticancer agents via inhibition of tubulin polymerization. Chen, P; Hu, T; Li, MM; Li, YR; Liu, X; Meng, LW; Song, J; Wang, SY; Yu, GX; Zhang, HY; Zhang, SY, 2021)	1.71

Excerpt	Reference	Relevance
" A small number of indoline fXa inhibitors were profiled in a dog pharmacokinetic model, one of which demonstrated pharmacokinetic parameters similar to that of clinical candidate razaxaban."	( Design, structure-activity relationship, and pharmacokinetic profile of pyrazole-based indoline factor Xa inhibitors. Bai, S; Ellis, CD; He, K; He, MY; Jacobson, IC; Knabb, RM; Lam, PY; Luettgen, JM; Quan, ML; Rossi, KA; Varnes, JG; Wacker, DA; Wexler, RR, 2007)	0.89

Excerpt	Reference	Relevance
" Some of the antagonists showed good oral bioavailability and/or good brain penetration."	( Identification of novel and orally active spiroindoline NPY Y5 receptor antagonists. Fukami, T; Gao, YD; Gomori, A; Haga, Y; Hidaka, M; Ishihara, A; Iwaasa, H; Kanatani, A; Kitazawa, H; Macneil, DJ; Moriya, M; Nonoshita, K; Okamoto, O; Sakamoto, T; Shibata, T; Takahashi, T; Yang, L, 2009)	0.61
" In particular, spiropiperidine indoline-substituted diaryl ureas are described as potent, orally bioavailable small-molecule P2Y1 antagonists with improved activity in functional assays and improved oral bioavailability in rats."	( Conformationally constrained ortho-anilino diaryl ureas: discovery of 1-(2-(1'-neopentylspiro[indoline-3,4'-piperidine]-1-yl)phenyl)-3-(4-(trifluoromethoxy)phenyl)urea, a potent, selective, and bioavailable P2Y1 antagonist. Abell, LM; Bostwick, JS; Bouthillier, G; Chang, M; Gao, Q; Hiebert, S; Hua, J; Huang, CS; L'Heureux, A; Lam, PY; Liu, E; Lloyd, J; Ma, B; McDonnell, PA; Pi, Z; Price, LA; Qiao, JX; Rehfuss, R; Ruel, R; Schnur, DM; Schumacher, WA; Spronk, SA; Steinbacher, TE; Thibeault, C; Wang, TC; Wexler, RR; Wu, Q; Zheng, J, 2013)	0.89
" KAE609 was well absorbed and extensively metabolized such that low levels of parent compound (≤11% of the dose) were detected in feces."	( Identification of Three Novel Ring Expansion Metabolites of KAE609, a New Spiroindolone Agent for the Treatment of Malaria, in Rats, Dogs, and Humans. Eggimann, FK; Einolf, HJ; Favara, S; Forseth, RR; Gu, H; He, H; Huskey, SE; Kittelmann, M; Li, H; Lin, MM; Luneau, A; Mangold, JB; Simon, O; Vargas, A; Wang, L; Zhang, J; Zhu, CQ, 2016)	0.43
" KAE609 was well absorbed and extensively metabolized, such that KAE609 accounted for approximately 32% of the dose in feces."	( KAE609 (Cipargamin), a New Spiroindolone Agent for the Treatment of Malaria: Evaluation of the Absorption, Distribution, Metabolism, and Excretion of a Single Oral 300-mg Dose of [14C]KAE609 in Healthy Male Subjects. Fredenhagen, A; Huskey, SE; Jain, JP; Jian, Z; Kühnöl, J; Luneau, A; Mangold, JB; Miao, Z; Stein, DS; Sunkara, G; Yang, F; Yang, Z; Zhu, CQ, 2016)	0.43
" Compound 13b, in particular, has a bioavailability of 22% and achieved a 96% tumor growth inhibition in an MDA-MB-468 xenograft study."	( Design and optimization of (3-aryl-1H-indazol-6-yl)spiro[cyclopropane-1,3'-indolin]-2'-ones as potent PLK4 inhibitors with oral antitumor efficacy. Awrey, DE; Ban, F; Beletskaya, I; Edwards, L; Feher, M; Forrest, BT; Green, E; Hodgson, R; Kiarash, R; Laufer, R; Li, SW; Liu, Y; Luo, X; Mak, TW; Mao, G; Mason, JM; Pan, G; Patel, NK; Pauls, HW; Sampson, PB; Wei, X, 2016)	0.43

Excerpt	Relevance	Reference
" After oral dosing of KAE609 to rats and dogs, the major radioactive component in plasma was KAE609."	( Identification of Three Novel Ring Expansion Metabolites of KAE609, a New Spiroindolone Agent for the Treatment of Malaria, in Rats, Dogs, and Humans. Eggimann, FK; Einolf, HJ; Favara, S; Forseth, RR; Gu, H; He, H; Huskey, SE; Kittelmann, M; Li, H; Lin, MM; Luneau, A; Mangold, JB; Simon, O; Vargas, A; Wang, L; Zhang, J; Zhu, CQ, 2016)	0.43
" Subjects reported semen discoloration after dosing in prior studies; therefore, semen samples were collected once from each subject to further evaluate this clinical observation."	( KAE609 (Cipargamin), a New Spiroindolone Agent for the Treatment of Malaria: Evaluation of the Absorption, Distribution, Metabolism, and Excretion of a Single Oral 300-mg Dose of [14C]KAE609 in Healthy Male Subjects. Fredenhagen, A; Huskey, SE; Jain, JP; Jian, Z; Kühnöl, J; Luneau, A; Mangold, JB; Miao, Z; Stein, DS; Sunkara, G; Yang, F; Yang, Z; Zhu, CQ, 2016)	0.43

Class	Description
indoles	Any compound containing an indole skeleton.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
regulation of DNA-templated transcription	Trp operon repressor	Escherichia coli K-12
regulation of DNA-templated transcription	Trp operon repressor	Escherichia coli K-12
negative regulation of DNA-templated transcription	Trp operon repressor	Escherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
DNA binding	Trp operon repressor	Escherichia coli K-12
DNA-binding transcription factor activity	Trp operon repressor	Escherichia coli K-12
sequence-specific DNA binding	Trp operon repressor	Escherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
cytoplasm	Trp operon repressor	Escherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Assay ID	Title	Year	Journal	Article
AID1799822	Binding Assay from Article : \\The structural basis for the interaction between L-tryptophan and the Escherichia coli trp aporepressor.\\	1987	The Journal of biological chemistry, Apr-05, Volume: 262, Issue:10	The structural basis for the interaction between L-tryptophan and the Escherichia coli trp aporepressor.
AID1369963	Cytoprotective activity against H2O2-induced oxidative stress in mouse RAW264.7 cells assessed as cell viability at 10 nM incubated for 2 hrs prior to H2O2 addition measured after 24 hrs by MTT assay (Rvb = 68 to 72.8%)	2018	Journal of medicinal chemistry, 05-10, Volume: 61, Issue:9	Synthesis and Biological Evaluation of Derivatives of Indoline as Highly Potent Antioxidant and Anti-inflammatory Agents.
AID281482	Inhibition of human intestinal carboxylesterase expressed in sf21 cells up to 100 uM	2007	Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8	Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
AID281483	Inhibition of human liver CE1 expressed in sf21 cells up to 100 uM	2007	Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8	Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
AID281484	Inhibition of rabbit liver carboxylesterase expressed in sf21 cells up to 100 uM	2007	Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8	Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	11 (2.61)	18.7374
1990's	6 (1.43)	18.2507
2000's	98 (23.28)	29.6817
2010's	244 (57.96)	24.3611
2020's	62 (14.73)	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	0 (0.00%)	5.53%
Reviews	9 (2.11%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	418 (97.89%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
ethylene dichloride ethylene dichloride: RN given refers to 1,2-isomer; structure given in first source. 1,2-dichloroethane : A member of the class of chloroethanes substituted by two chloro groups at positions 1 and 2.	2.1	1	chloroethanes	hepatotoxic agent; mutagen; non-polar solvent
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.	2.49	2	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
adenine [no description available]	7.05	1	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
beta-alanine [no description available]	2	1	amino acid zwitterion; beta-amino acid	agonist; fundamental metabolite; human metabolite; inhibitor; neurotransmitter
benzene [no description available]	7.97	4	aromatic annulene; benzenes; volatile organic compound	carcinogenic agent; environmental contaminant; non-polar solvent
benzoic acid Benzoic Acid: A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid.. benzoic acid : A compound comprising a benzene ring core carrying a carboxylic acid substituent.. aromatic carboxylic acid : Any carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.	2.47	2	benzoic acids	algal metabolite; antimicrobial food preservative; drug allergen; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; human xenobiotic metabolite; plant metabolite
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)	2.41	1	halide anion; monoatomic bromine
carbamates [no description available]	2.78	3	amino-acid anion
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).	3.01	4	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	2.77	3	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
coumarin 2H-chromen-2-one: coumarin derivative	2.1	1	coumarins	fluorescent dye; human metabolite; plant metabolite
2,3-diaminopropionic acid 3-aminoalanine : A diamino acid that is alanine in which one of the hydrogens of the methyl group is replaced by an amino group.	2	1	alanine derivative; amino acid zwitterion; beta-amino acid; diamino acid; non-proteinogenic alpha-amino acid	Escherichia coli 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.	2.1	1	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
alpha-glycerophosphoric acid [no description available]	2.02	1	glycerol monophosphate	algal metabolite; human metabolite
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.	8.6	8	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
hydroxylamine amino alcohol : An alcohol containing an amino functional group in addition to the alcohol-defining hydroxy group.	2.21	1	hydroxylamines	algal metabolite; bacterial xenobiotic metabolite; EC 1.1.3.13 (alcohol oxidase) inhibitor; EC 4.2.1.22 (cystathionine beta-synthase) inhibitor; EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor; nitric oxide donor; nucleophilic reagent
indole [no description available]	4.08	15	indole; polycyclic heteroarene	Escherichia coli metabolite
iodine Iodine: A nonmetallic element of the halogen group that is represented by the atomic symbol I, atomic number 53, and atomic weight of 126.90. It is a nutritionally essential element, especially important in thyroid hormone synthesis. In solution, it has anti-infective properties and is used topically.. diiodine : Molecule comprising two covalently bonded iodine atoms with overall zero charge..	2.17	1	diatomic iodine	nutrient
thioctic acid Thioctic Acid: An octanoic acid bridged with two sulfurs so that it is sometimes also called a pentanoic acid in some naming schemes. It is biosynthesized by cleavage of LINOLEIC ACID and is a coenzyme of oxoglutarate dehydrogenase (KETOGLUTARATE DEHYDROGENASE COMPLEX). It is used in DIETARY SUPPLEMENTS.	2.31	1	dithiolanes; heterocyclic fatty acid; thia fatty acid	fundamental metabolite; geroprotector
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.	7.01	1	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]	2.01	1	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
acetanilide acetanilide: a phenylacetamide; use ACETANILIDES for the plural group meaning of the singular term. N-phenylacetamide : A member of the class of acetamides that is acetamide in which one of the hydrogens attached to the nitrogen is substituted by a phenyl group.	7.1	1	acetamides; anilide	analgesic
naphthalene [no description available]	2	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.	7.49	2	metal allergen; nickel group element atom	epitope; micronutrient
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	2.58	2	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
nitroxyl nitroxyl: hydroxamic acid oxidized to nitroxyl free radical. nitroxyl : A nitrogen oxoacid consisting of an oxygen atom double-bonded to an NH group.	2.13	1	nitrogen oxoacid
phenanthrene phenanthrene : A polycyclic aromatic hydrocarbon composed of three fused benzene rings which takes its name from the two terms 'phenyl' and 'anthracene.'	2	1	ortho-fused polycyclic arene; ortho-fused tricyclic hydrocarbon; phenanthrenes	environmental contaminant; mouse metabolite
phosphoric acid phosphoric acid: concise etchant is 37% H3PO4. phosphoric acid : A phosphorus oxoacid that consists of one oxo and three hydroxy groups joined covalently to a central phosphorus atom.	7.78	3	phosphoric acids	algal metabolite; fertilizer; human metabolite; NMR chemical shift reference compound; solvent
pyrazole 1H-pyrazole : The 1H-tautomer of pyrazole.	7.03	1	pyrazole
pyridine azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.	2.84	3	azaarene; mancude organic heteromonocyclic parent; monocyclic heteroarene; pyridines	environmental contaminant; NMR chemical shift reference compound
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.	2.43	2	2-oxo monocarboxylic acid	cofactor; fundamental metabolite
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	2	1	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
tryptamine [no description available]	7.5	2	aminoalkylindole; aralkylamino compound; indole alkaloid; tryptamines	human metabolite; mouse metabolite; plant metabolite
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	2.06	1	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.	7.99	4	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	2.47	2	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
4-diphenylacetoxy-1,1-dimethylpiperidinium 4-diphenylacetoxy-1,1-dimethylpiperidinium: muscarinic receptor antagonist; RN given refers to parent cpd; do not confuse abbreviation 4-DAMP with a similar cpd which does not contain dimethyl groups. 4-DAMP(1+) : A quaternary ammonium salt obtained by formal methylation of the tertiary amino function of 4-diphenylacetoxy-N-methylpiperidine.	1.99	1	quaternary ammonium ion	cholinergic antagonist; muscarinic antagonist
5-hydroxydecanoate 5-hydroxydecanoic acid: Potassium Channel Blocker; RN refers to parent cpd	2.01	1	medium-chain fatty acid
benzamide benzamide : An aromatic amide that consists of benzene bearing a single carboxamido substituent. The parent of the class of benzamides.	2.02	1	benzamides
chlorthalidone Chlorthalidone: A benzenesulfonamide-phthalimidine that tautomerizes to a BENZOPHENONES form. It is considered a thiazide-like diuretic.	1.93	1	isoindoles; monochlorobenzenes; sulfonamide
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.	7.11	1	ether; volatile organic compound	inhalation anaesthetic; non-polar solvent; refrigerant
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.	2.13	1	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
hydroxyurea [no description available]	2	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
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).	7.25	1	carbohydrazide	antitubercular agent; drug allergen
kojic acid [no description available]	2.1	1	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
methoxyamine methoxyamine: analytical reagent for aldehydes and ketones; strong irritant, can probably produce methemoglobinemia; RN given refers to parent cpd; structure	2	1	organooxygen compound
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.	2.04	1	benzylisoquinoline alkaloid; dimethoxybenzene; isoquinolines	antispasmodic drug; vasodilator agent
piracetam Piracetam: A compound suggested to be both a nootropic and a neuroprotective agent.	2.15	1	organonitrogen compound; organooxygen compound
pirenzepine Pirenzepine: An antimuscarinic agent that inhibits gastric secretion at lower doses than are required to affect gastrointestinal motility, salivary, central nervous system, cardiovascular, ocular, and urinary function. It promotes the healing of duodenal ulcers and due to its cytoprotective action is beneficial in the prevention of duodenal ulcer recurrence. It also potentiates the effect of other antiulcer agents such as CIMETIDINE and RANITIDINE. It is generally well tolerated by patients.	1.99	1	pyridobenzodiazepine	anti-ulcer drug; antispasmodic drug; muscarinic antagonist
tyramine [no description available]	2.08	1	monoamine molecular messenger; primary amino compound; tyramines	EC 3.1.1.8 (cholinesterase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter
vesamicol vesamicol: RN given refers to parent cpd; structure	7.15	1	piperidines
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.	1.93	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
benzimidazole 1H-benzimidazole : The 1H-tautomer of benzimidazole.	2.42	2	benzimidazole; polycyclic heteroarene
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.	1.93	1	3-oxo-Delta(4) steroid; oxaspiro compound; steroid lactone; thioester	aldosterone antagonist; antihypertensive agent; diuretic; environmental contaminant; xenobiotic
aldosterone [no description available]	6.93	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
estrone Hydroxyestrones: Estrone derivatives substituted with one or more hydroxyl groups in any position. They are important metabolites of estrone and other estrogens.	7.6	1	17-oxo steroid; 3-hydroxy steroid; phenolic steroid; phenols	antineoplastic agent; bone density conservation agent; estrogen; human metabolite; mouse metabolite
(4-(m-chlorophenylcarbamoyloxy)-2-butynyl)trimethylammonium chloride (4-(m-Chlorophenylcarbamoyloxy)-2-butynyl)trimethylammonium Chloride: A drug that selectively activates certain subclasses of muscarinic receptors and also activates postganglionic nicotinic receptors. It is commonly used experimentally to distinguish muscarinic receptor subtypes.	1.99	1
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.	2.74	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
serine Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.	2.43	2	L-alpha-amino acid; proteinogenic amino acid; serine family amino acid; serine zwitterion; serine	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
aspartic acid Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.	2	1	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
cyanides Cyanides: Inorganic salts of HYDROGEN CYANIDE containing the -CN radical. The concept also includes isocyanides. It is distinguished from NITRILES, which denotes organic compounds containing the -CN radical.. cyanides : Salts and C-organyl derivatives of hydrogen cyanide, HC#N.. isocyanide : The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)).. cyanide : A pseudohalide anion that is the conjugate base of hydrogen cyanide.	2.73	3	pseudohalide anion	EC 1.9.3.1 (cytochrome c oxidase) inhibitor
physostigmine Physostigmine: A cholinesterase inhibitor that is rapidly absorbed through membranes. It can be applied topically to the conjunctiva. It also can cross the blood-brain barrier and is used when central nervous system effects are desired, as in the treatment of severe anticholinergic toxicity.	2.44	2	carbamate ester; indole alkaloid	antidote to curare poisoning; EC 3.1.1.8 (cholinesterase) inhibitor; miotic
2,3,4,6-tetrachlorophenol 2,3,4,6-tetrachlorophenol: RN given refers to parent cpd; see also record for tetrachlorophenol with locants for chloro groups not specified. 2,3,4,6-tetrachlorophenol : A tetrachlorophenol in which the chlorines are located at positions 2, 3, 4, and 6.	2.03	1	tetrachlorophenol	xenobiotic metabolite
galactose galactopyranose : The pyranose form of galactose.	7.15	1	D-galactose; galactopyranose	Escherichia coli metabolite; mouse metabolite
carbostyril Quinolones: A group of derivatives of naphthyridine carboxylic acid, quinoline carboxylic acid, or NALIDIXIC ACID.. quinolin-2(1H)-one : A quinolone that is 1,2-dihydroquinoline substituted by an oxo group at position 2.	2.05	1	monohydroxyquinoline; quinolone	bacterial xenobiotic metabolite
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.	2.03	1	benzenes; primary alcohol	Aspergillus metabolite; fragrance; plant growth retardant; plant metabolite; Saccharomyces cerevisiae metabolite
adenosine monophosphate Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.	2.31	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
methicillin Methicillin: One of the PENICILLINS which is resistant to PENICILLINASE but susceptible to a penicillin-binding protein. It is inactivated by gastric acid so administered by injection.. methicillin : A penicillin that is 6-aminopenicillanic acid in which one of the amino hydrogens is replaced by a 2,6-dimethoxybenzoyl group.	7.08	1	penicillin allergen; penicillin	antibacterial drug
aniline [no description available]	3.54	8	anilines; primary arylamine
phenylalanine Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.	2.44	2	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
egtazic acid Egtazic Acid: A chelating agent relatively more specific for calcium and less toxic than EDETIC ACID.. ethylene glycol bis(2-aminoethyl)tetraacetic acid : A diether that is ethylene glycol in which the hydrogens of the hydroxy groups have been replaced by 2-[bis(carboxymethyl)amino]ethyl group respectively.	3.15	1	diether; tertiary amino compound; tetracarboxylic acid	chelator
asparagine Asparagine: A non-essential amino acid that is involved in the metabolic control of cell functions in nerve and brain tissue. It is biosynthesized from ASPARTIC ACID and AMMONIA by asparagine synthetase. (From Concise Encyclopedia Biochemistry and Molecular Biology, 3rd ed). asparagine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 2-amino-2-oxoethyl group.	2.05	1	amino acid zwitterion; asparagine; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
histidine Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.	2.05	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.	2.7	3	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
acetylene [no description available]	7.05	1	alkyne; gas molecular entity; terminal acetylenic compound
propane Propane: A three carbon alkane with the formula H3CCH2CH3.	2.05	1	alkane; gas molecular entity	food propellant
cyclopropane cyclopropane : A cycloalkane composed of three carbon atoms to form a ring.	4.09	4	cycloalkane; cyclopropanes	inhalation anaesthetic
trimethylchlorosilane trimethylsilyl chloride: structure in first source. chlorotrimethylsilane : A silyl chloride consisting of a central silicon atom covalently bound to one chloro and three methyl groups. Chlorotrimethylsilane is a derivatisation agent used in gas chromatography/mass spectrometry applications.	2.08	1	silyl chloride	chromatographic reagent
trifluoroethanol Trifluoroethanol: A non-aqueous co-solvent that serves as tool to study protein folding. It is also used in various pharmaceutical, chemical and engineering applications.	2.41	1	fluoroalcohol
divinyl sulfone divinyl sulfone: cross-linking reagent for agarose gels. divinyl sulfone : A sulfone compound having two S-vinyl substituents.	2.05	1	sulfone	cross-linking reagent
acrylamide [no description available]	7.06	1	acrylamides; N-acylammonia; primary carboxamide	alkylating agent; carcinogenic agent; Maillard reaction product; mutagen; neurotoxin
dichlorodicyanobenzoquinone dichlorodicyanobenzoquinone: request from searcher	2.55	2
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.	2.03	1	phthalimides
carbazole carbazole: structure in first source	3.18	1	carbazole
5-bromoisatin [no description available]	2.03	1	indoles	anticoronaviral agent
2-nitrotoluene nitrotoluene : Any member of the class of toluenes bearing one or more nitro substituents on the benzene ring.	2	1	mononitrotoluene	carcinogenic agent; environmental contaminant
quinoline [no description available]	7.05	1	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinolines
isatin 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;	3.42	7	indoledione	EC 1.4.3.4 (monoamine oxidase) inhibitor; plant metabolite
phenidone phenidone: photographic developer; RN given refers to parent cpd; structure	2	1
diphenyl diphenyl: RN given refers to unlabeled cpd; structure	2	1	aromatic fungicide; benzenes; biphenyls	antifungal agrochemical; antimicrobial food preservative
xanthenes Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.	2.1	1	xanthene
indene indene: structure in first source. 1H-indene : An ortho-fused bicyclic arene comprising of benzene and cyclopentene rings.	2.41	2	indene; ortho-fused bicyclic arene
benzothiophene [no description available]	2.17	1	1-benzothiophenes; benzothiophene
benzothiazole benzothiazole: structure. benzothiazole : An organic heterobicyclic compound that is a fusion product between benzene and thiazole. The parent of the class of benzothiazoles.	1.97	1	benzothiazoles	environmental contaminant; plant metabolite; xenobiotic
2-methylindole 2-methylindole: SKATOLE refers to 3-methylindole; RN given refers to parent cpd; structure. 2-methyl-1H-indole : A methylindole that is 1H-indole substituted by a methyl group at position 2.	7.01	1	methylindole
4-butyrolactone 4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.	2.08	1	butan-4-olide	metabolite; neurotoxin
nitrobenzene nitrobenzene : A nitroarene consisting of benzene carrying a single nitro substituent. An industrial chemical used widely in the production of aniline.	3.15	1	nitroarene; nitrobenzenes
3-dinitrobenzene dinitrobenzene : Any member of the class of nitrobenzenes that consists of a benzene ring substituted by two nitro groups. A closed class.. 1,3-dinitrobenzene : A dinitrobenzene that is benzene disubstituted at positions 1 and 3 with nitro groups.	2.13	1	dinitrobenzene	neurotoxin
styrene Styrene: A colorless, toxic liquid with a strong aromatic odor. It is used to make rubbers, polymers and copolymers, and polystyrene plastics.. styrene : A vinylarene that is benzene carrying a vinyl group. It has been isolated from the benzoin resin produced by Styrax species.	2.11	1	styrenes; vinylarene; volatile organic compound	mouse metabolite; mutagen; plant metabolite
benzylamine aminotoluene : Any member of the class of toluenes carrying one or more amino groups.	2.05	1	aralkylamine; primary amine	allergen; EC 3.5.5.1 (nitrilase) inhibitor; plant metabolite
benzonitrile benzonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a phenyl group.	2.1	1	benzenes; nitrile
ethyl cyanoacetate ethyl cyanoacetate: affect muscarinic and nicotinic receptors; RN given refers to unlabeled parent cpd	2.1	1
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
dicyanmethane malononitrile : A dinitrile that is methane substituted by two cyano groups.	2.5	2	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.	5.7	14	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.	7.52	2	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
piperidine [no description available]	3.59	2	azacycloalkane; piperidines; saturated organic heteromonocyclic parent; secondary amine	base; catalyst; human metabolite; non-polar solvent; plant metabolite; protic solvent; reagent
isoquinoline [no description available]	2.05	1	azaarene; isoquinolines; mancude organic heterobicyclic parent; ortho-fused heteroarene
2,5-norbornadiene [no description available]	2.05	1
1-naphthylamine 1-Naphthylamine: A suspected industrial carcinogen (and listed as such by OSHA). Its N-hydroxy metabolite is strongly carcinogenic and mutagenic.. naphthylamine : A primary arylamine that is naphthalene substituted by an amino group at unspecified position.. 1-naphthylamine : A naphthylamine that is naphthalene substituted by an amino group at position 1.	2.11	1	naphthylamine	human xenobiotic metabolite
iminodiacetic acid iminodiacetic acid: used as hepatobiliary imaging agent when labeled with Tc; RN given refers to parent cpd; structure. iminodiacetic acid : An amino dicarboxylic acid that is glycine in which one of the hydrogens attached to the nitrogen is substituted by a carboxymethyl group.	2.01	1	amino dicarboxylic acid; glycine derivative; non-proteinogenic alpha-amino acid	chelator
phthalazine phthalazine : An azaarene that is the 2,3-diaza analogue of naphthalene. The parent of the class of phthalazines.	7.07	1	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; phthalazines
cinnoline cinnoline: structure in first source. cinnoline : An azaarene that is the 1,2-diaza analogue of naphthalene. The parent of the class of cinnolines.	7.04	1	azaarene; cinnolines; mancude organic heterobicyclic parent; ortho-fused heteroarene
quinazolines Quinazolines: A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.. quinazoline : A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.. quinazolines : Any organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.	7.08	1	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
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
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	8.2	5	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
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.	2.07	1	1,3-oxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiazoles [no description available]	2.42	2	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
calcium gluconate [no description available]	2.21	1	calcium salt	nutraceutical
ephedrine Ephedrine: A phenethylamine found in EPHEDRA SINICA. PSEUDOEPHEDRINE is an isomer. It is an alpha- and beta-adrenergic agonist that may also enhance release of norepinephrine. It has been used for asthma, heart failure, rhinitis, and urinary incontinence, and for its central nervous system stimulatory effects in the treatment of narcolepsy and depression. It has become less extensively used with the advent of more selective agonists.. (-)-ephedrine : A phenethylamine alkaloid that is 2-phenylethanamine substituted by a methyl group at the amino nitrogen and a methyl and a hydroxy group at position 2 and 1 respectively.	2.05	1	phenethylamine alkaloid; phenylethanolamines	bacterial metabolite; environmental contaminant; nasal decongestant; plant metabolite; sympathomimetic agent; vasoconstrictor agent; xenobiotic
hydrazine diamine : Any polyamine that contains two amino groups.	2.98	4	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
phthalimidine phthalimidine: structure given in first source. isoindolin-1-one : A member of the class of isoindoles that is 2,3-dihydro-1H-isoindole in which the hydrogens at positon 1 are replaced by an oxo group.	2.41	1	gamma-lactam; isoindoles
kainic acid Kainic Acid: (2S-(2 alpha,3 beta,4 beta))-2-Carboxy-4-(1-methylethenyl)-3-pyrrolidineacetic acid. Ascaricide obtained from the red alga Digenea simplex. It is a potent excitatory amino acid agonist at some types of excitatory amino acid receptors and has been used to discriminate among receptor types. Like many excitatory amino acid agonists it can cause neurotoxicity and has been used experimentally for that purpose.	2.02	1	dicarboxylic acid; L-proline derivative; non-proteinogenic L-alpha-amino acid; pyrrolidinecarboxylic acid	antinematodal drug; excitatory amino acid agonist
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.	2.41	2	indanes; ortho-fused bicyclic hydrocarbon
coumaran 2,3-dihydrobenzofuran : A member of the class of 1-benzofurans that is the 2,3-dihydroderivative of benzofuran.	1.98	1	1-benzofurans	metabolite
tryptophol tryptophol : An indolyl alcohol that is ethanol substituted by a 1H-indol-3-yl group at position 2.	1.97	1	indolyl alcohol	auxin; plant metabolite; Saccharomyces cerevisiae metabolite
1-acetylisatin 1-acetylisatin: structure in first source	2.03	1	indoledione
nitrosobenzene [no description available]	2.1	1	benzenes; nitroso compound	xenobiotic metabolite
n-methylhydroxylamine [no description available]	2	1
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	2.03	1
pentamethylbenzene [no description available]	3.18	1	methylbenzene
2-phenylbenzothiazole 2-phenylbenzothiazole: structure given in first source	1.97	1
cyclopentenone 2-cyclopenten-1-one : An enone that is cyclopentanone having a C=C double bond at position 2.	7.79	3	alicyclic ketone; enone	Hsp70 inducer
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.	3	4	zinc molecular entity
5-methyltryptamine 5-methyltryptamine: RN given refers to parent cpd	1.97	1	tryptamines
meldrum's acid Meldrum's acid: structure given in first source	2.1	1
n-methylisatin N-methylisatin: structure given in first source	2.03	1
tetramethylthiourea [no description available]	2.08	1	thioureas
copper(ii) nitrate copper(II) nitrate : An inorganic nitrate salt having copper(2+) as the couterion.	2.25	1	inorganic nitrate salt
2-(2-hydroxyphenyl)benzothiazole 2-(1,3-benzothiazol-2-yl)phenol : A member of the class of benzothiazoles that is 1,3-benzothiazole substituted by a 2-hydroxyphenyl group at position 2.	1.97	1	benzothiazoles; phenols	geroprotector
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.	7.59	2	carbon oxoanion
2-amino-1,3,4-thiadiazole 2-amino-1,3,4-thiadiazole: structure; RN given refers to parent cpd	2.1	1
1-indanol [no description available]	1.98	1	aromatic alcohol; indanes; secondary alcohol	xenobiotic
iridium Iridium: A metallic element with the atomic symbol Ir, atomic number 77, and atomic weight 192.22.	3	4	cobalt group element atom; platinum group metal atom
manganese Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.	3.24	5	elemental manganese; manganese group element atom	Escherichia coli metabolite; micronutrient
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.	5.01	36	metal allergen; nickel group element atom; platinum group metal atom
platinum Platinum: A heavy, soft, whitish metal, resembling tin, with atomic number 78, atomic weight 195.084, symbol Pt. It is used in manufacturing equipment for laboratory and industrial use. It occurs as a black powder (platinum black) and as a spongy substance (spongy platinum) and may have been known in Pliny's time as alutiae.	7.05	1	elemental platinum; nickel group element atom; platinum group metal 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.	4.25	16	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.	3.36	6	iron group element atom; platinum group metal atom
silver Silver: An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.	2.5	2	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.	2.49	2	titanium group element atom
tungsten Tungsten: A metallic element with the atomic symbol W, atomic number 74, and atomic weight 183.85. It is used in many manufacturing applications, including increasing the hardness, toughness, and tensile strength of steel; manufacture of filaments for incandescent light bulbs; and in contact points for automotive and electrical apparatus.	2.05	1	chromium group element atom	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.	3.45	7	copper group element atom; elemental gold
ferric chloride ferric chloride: RN given refers to cpd with MF of Fe-Cl3; used to induce experimental arterial thrombosis to evaluate antithrombotic agents	2.77	3	iron coordination entity	astringent; Lewis acid
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.	7.11	1	mononuclear parent hydride; phosphanes; phosphine	carcinogenic agent; fumigant insecticide
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	2	1	dihydrogen
fluorine Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.	2.46	2	diatomic fluorine; gas molecular entity	NMR chemical shift reference compound
chlorine Chlorine: An element with atomic symbol Cl, atomic number 17, and atomic weight 35, and member of the halogen family.	2.1	1	diatomic chlorine; gas molecular entity	bleaching agent
titanium dioxide titanium dioxide: used medically as protectant against externally caused irritation & sunlight; high concentrations of dust may cause irritation to respiratory tract; RN given refers to titanium oxide (TiO2); structure. titanium dioxide : A titanium oxide with the formula TiO2. A naturally occurring oxide sourced from ilmenite, rutile and anatase, it has a wide range of applications.	2.49	2	titanium oxides	food colouring
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.	2.06	1
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	2.5	2	benzenes; phenyl acetates
pyrrolidine [no description available]	9.08	4	azacycloalkane; pyrrolidines; saturated organic heteromonocyclic parent
chloroprene Chloroprene: Toxic, possibly carcinogenic, monomer of neoprene, a synthetic rubber; causes damage to skin, lungs, CNS, kidneys, liver, blood cells and fetuses. Synonym: 2-chlorobutadiene.	2.11	1	chloroolefin
alkenes [no description available]	3.96	12
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	3.34	6	pseudohalide anion	mitochondrial respiratory-chain inhibitor
5-Methoxyisatin [no description available]	2.03	1	indoles	anticoronaviral agent
dihydroalprenolol Dihydroalprenolol: Hydrogenated alprenolol derivative where the extra hydrogens are often tritiated. This radiolabeled form of ALPRENOLOL, a beta-adrenergic blocker, is used to label the beta-adrenergic receptor for isolation and study.	2.02	1
indoxyl 3-hydroxyindole: inhibits amyloid fibril formation; structure in first source	2.53	2	heteroaryl hydroxy compound; hydroxyindoles
zileuton [no description available]	2	1	1-benzothiophenes; ureas	anti-asthmatic drug; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; ferroptosis inhibitor; leukotriene antagonist; non-steroidal anti-inflammatory drug
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.	2.5	2	one-carbon compound; perfluoroalkanesulfonic acid
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.	2.11	1	D-glucopyranose	epitope; mouse metabolite
milnacipran Milnacipran: A cyclopropanecarboxamide serotonin and norepinephrine reuptake inhibitor (SNRI) that is used in the treatment of FIBROMYALGIA.	2.04	1	acetamides
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.	8.05	4	1,2,3-triazole
triflic anhydride triflic anhydride: structure in first source	2.01	1	organosulfonic anhydride
n-phenylphthalimide N-phenylphthalimide: structure given in first source	2.03	1
hordenine [no description available]	2.08	1	phenethylamine alkaloid	human metabolite; mouse metabolite
4-aminoquinoline [no description available]	7.25	1
1,2,3,4-tetrahydroquinoline 1,2,3,4-tetrahydroquinoline: structure in first source. 1,2,3,4-tetrahydroquinoline : A member of the class of quinolines that is the 1,2,3,4-tetrahydro derivative of quinoline.	8.51	7	quinolines
methanesulfonamide [no description available]	7.05	1
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.	2.05	1	carbohydrazide; one-carbon compound
rivastigmine [no description available]	2.15	1	carbamate ester; tertiary amino compound	cholinergic drug; EC 3.1.1.8 (cholinesterase) inhibitor; neuroprotective agent
methylenecyclopropane methylenecyclopropane: structure in first source	7.06	1
1,8-diazabicyclo(5.4.0)undec-7-ene [no description available]	2.05	1
1,3-bis(diphenylphosphino)propane 1,3-bis(diphenylphosphino)propane: structure in first source	2.05	1
5-Chloro-1H-indole-2,3-dione [no description available]	2.03	1	indoles	anticoronaviral agent
5-iodoisatin 5-iodoisatin: structure in first source	2.03	1	indoles	anticoronaviral agent
firefly luciferin Firefly Luciferin: A benzothaizole which is oxidized by LUCIFERASES, FIREFLY to cause emission of light (LUMINESCENCE).. Photinus luciferin : A 1,3-thiazolemonocarboxylic acid consisting of 3,5-dihydrothiophene-4-carboxylic acid having a 6-hydroxybenzothiazol-2-yl group at the 2-position.	1.97	1	1,3-thiazolemonocarboxylic acid; benzothiazoles; imidothioate	luciferin
n-acetyldehydroalanine methyl ester N-acetyldehydroalanine methyl ester: modifies amino & sulfhydryl groups in amino acids & proteins; structure	2.04	1
virantmycin virantmycin: has potent antifungal activity & potent inhibitory activity against DNA & RNA viruses; from Streptomyces nitrosporeus No. AM-2722; structure in 2nd source	2.47	2
hippadine hippadine: isolated from Crinum bulbs	7.02	1
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.	7.02	1	cobalt group element atom; metal allergen	micronutrient
vitamin b 6 Vitamin B 6: VITAMIN B 6 refers to several PICOLINES (especially PYRIDOXINE; PYRIDOXAL; & PYRIDOXAMINE) that are efficiently converted by the body to PYRIDOXAL PHOSPHATE which is a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, and aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into PYRIDOXAMINE phosphate. Although pyridoxine and Vitamin B 6 are still frequently used as synonyms, especially by medical researchers, this practice is erroneous and sometimes misleading (EE Snell; Ann NY Acad Sci, vol 585 pg 1, 1990). Most of vitamin B6 is eventually degraded to PYRIDOXIC ACID and excreted in the urine.	2.06	1
cyanates Cyanates: Organic salts of cyanic acid containing the -OCN radical.. cyanates : Salts and esters of cyanic acid, HOC#N; compounds carrying the cyanate functional group -O-C#N.. isocyanates : Organonitrogen compounds that are derivatives of isocyanic acid; compounds containing the isocyanate functional group -N=C=O (as opposed to the cyanate group, -O-C#N).	2.05	1
tryptophan methyl ester tryptophan methyl ester: RN given refers to parent cpd(DL)-isomer	1.97	1
chlorodimedone [no description available]	2.06	1
benzyne benzyne: structure in first source. benzyne : 1,2-didehydrobenzene and its derivatives formed by substitution.	9.09	4	aryne; benzyne
carbene carbene: electrically neutral species H2C: and its derivatives, in which the carbon is covalently bonded to two univalent groups of any kind or a divalent group and bears two nonbonding electrons; carbene is the name of the parent hydride :CH2 ; hence, the name dichlorocarbene for :CCl2. However, names for acyclic and cyclic hydrocarbons containing one or more divalent carbon atoms are derived from the name of the corresponding all-4-hydrocarbon using the suffix -ylidene; methylene carbene also available. carbene : The electrically neutral species H2C(2.) and its derivatives, in which the carbon is covalently bonded to two univalent groups of any kind or a divalent group and bears two nonbonding electrons, which may be spin-paired (singlet state) or spin-non-paired (triplet state).	2.79	3	carbene; methanediyl
dehydroalanine 2-ammonioprop-2-enoate : An amino acid zwitterion resulting from a transfer of a proton from the carboxy group to the amino group of 2-aminoacrylic acid.. 2-aminoacrylic acid : A 2,3-dehydroamino acid that is alanine which has been dehydrogenated to introduce a double bond between positions 2 and 3.	2.02	1	2,3-dehydroamino acid; alpha,beta-unsaturated monocarboxylic acid; amino acid zwitterion; enamine; non-proteinogenic alpha-amino acid	alkylating agent; human metabolite; mouse metabolite
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.	2.41	1	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.	2.52	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.	2.83	3	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
pyrindamycin a pyrindamycin A: isolated from Streptomyces sp. SF2582	2.01	1
dirhodium tetraacetate dirhodium tetraacetate: structure given in first source	2.06	1
thionium [no description available]	7.45	2
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	2.02	1	oxygen hydride; oxygen radical; reactive oxygen species
aristololactam bii aristololactam BII: isolated from Saururus cernuus; structure given in first source	2.02	1
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	2.06	1	divalent inorganic anion; phosphite ion
aflatoxin b1 Aflatoxin B1: A potent hepatotoxic and hepatocarcinogenic mycotoxin produced by the Aspergillus flavus group of fungi. It is also mutagenic, teratogenic, and causes immunosuppression in animals. It is found as a contaminant in peanuts, cottonseed meal, corn, and other grains. The mycotoxin requires epoxidation to aflatoxin B1 2,3-oxide for activation. Microsomal monooxygenases biotransform the toxin to the less toxic metabolites aflatoxin M1 and Q1.. aflatoxin B1 : An aflatoxin having a tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4 and 11.	2.05	1	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
1,4,7-triazacyclononane 1,4,7-triazacyclononane: structure given in first source	7.02	1	azacycloalkane; crown amine; saturated organic heteromonocyclic parent
phenserine phenserine: a carbamate analog of physostigmine; a long-acting inhibitor of cholinesterase	7.02	1
5-Fluoroisatin [no description available]	2.03	1	indoles	anticoronaviral agent
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	2.96	4
2-oxindole 2-oxindole: RN given refers to parent cpd; structure. indolin-2-one : An indolinone carrying an oxo group at position 2.	3.57	8	gamma-lactam; indolinone
anhydrolycorinone anhydrolycorinone: structure in first source	7.02	1	phenanthridines
diazonamide a diazonamide A: structure in first source	2.07	1
strychnine Strychnine: An alkaloid found in the seeds of STRYCHNOS NUX-VOMICA. It is a competitive antagonist at glycine receptors and thus a convulsant. It has been used as an analeptic, in the treatment of nonketotic hyperglycinemia and sleep apnea, and as a rat poison.. strychnine : A monoterpenoid indole alkaloid that is strychnidine bearing a keto substituent at the 10-position.	1.93	1	monoterpenoid indole alkaloid; organic heteroheptacyclic compound	avicide; cholinergic antagonist; glycine receptor antagonist; neurotransmitter agent; rodenticide
physovenine physovenine: structure given in first source	2.05	1	indoles
indoleglycerol phosphate indoleglycerol phosphate: inducer of tryptophan synthase. (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate : The (1S,2R)-diastereomer of 1-C-(indol-3-yl)glycerol 3-phosphate.	2.44	2	1-C-(indol-3-yl)glycerol 3-phosphate
di-tert-butyldiaziridinone di-tert-butyldiaziridinone: structure in first source	2.1	1
n-fluorobenzenesulfonimide N-fluorobenzenesulfonimide: structure in first source	2.08	1
xantphos xantphos: structure in first source	2.1	1
glycosides [no description available]	7.49	2
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	2.06	1	stilbene
thiohydantoins Thiohydantoins: Sulfur analogs of hydantoins with one or both carbonyl groups replaced by thiocarbonyl groups.	2.15	1
1-[(3,4-dichlorophenyl)methyl]indole-2,3-dione [no description available]	2.03	1	indoles
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	4	one-carbon compound; thioureas; ureas	antioxidant; chromophore
tempo TEMPO: structure. TEMPO : A member of the class of aminoxyls that is piperidine that carries an oxidanediyl group at position 1 and methyl groups at positions 2, 2, 6, and 6, respectively.	2.07	1	aminoxyls; piperidines	catalyst; ferroptosis inhibitor; radical scavenger
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
lithium Lithium: An element in the alkali metals family. It has the atomic symbol Li, atomic number 3, and atomic weight [6.938; 6.997]. Salts of lithium are used in treating BIPOLAR DISORDER.	2.72	3	alkali metal atom
perophoramidine perophoramidine: from the Philippine ascidian Perophora namei; structure in first source	7.03	1
pactimibe [no description available]	2.05	1
chloramine-b chloramine-B: RN given refers to parent cpd	7.1	1
5-Nitroisatin [no description available]	2.03	1	indoles	anticoronaviral agent
pyrroloquinoline pyrroloquinoline: check to see if actually PYRROLOQUINOLINE QUINONE (PQQ COFACTOR)	2.11	1
epinephrine ircinal A: from an Indonesian Acanthostrongylophora sponge with activity against infectious, tropical parasitic, and Alzheimer's diseases; structure in first source	3.41	1
quercetin [no description available]	2.17	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
pulmicort Budesonide: A glucocorticoid used in the management of ASTHMA, the treatment of various skin disorders, and allergic RHINITIS.. budesonide : A glucocorticoid steroid having a highly oxygenated pregna-1,4-diene structure. It is used mainly in the treatment of asthma and non-infectious rhinitis and for treatment and prevention of nasal polyposis.	2.17	1	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; cyclic acetal; glucocorticoid; primary alpha-hydroxy ketone	anti-inflammatory drug; bronchodilator agent; drug allergen
heptaphylline heptaphylline: cytotoxic carbazole alkaloid from the roots of Clausena harmandiana; structure in first source	3.59	2	carbazoles	metabolite
semaxinib semaxanib : An oxindole that is 3-methyleneoxindole in which one of the hydrogens of the methylene group is replaced by a 3,5-dimethylpyrrol-2-yl group.	3.13	1	olefinic compound; oxindoles; pyrroles	angiogenesis modulating agent; antineoplastic agent; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; vascular endothelial growth factor receptor antagonist
cesium Cesium: A member of the alkali metals. It has an atomic symbol Cs, atomic number 50, and atomic weight 132.91. Cesium has many industrial applications, including the construction of atomic clocks based on its atomic vibrational frequency.	2.05	1	alkali metal atom
thallium Thallium: A heavy, bluish white metal, atomic number 81, atomic weight [204.382; 204.385], symbol Tl.. thallium : A metallic element first identified and named from the brilliant green line in its flame spectrum (from Greek thetaalphalambdalambdaomicronsigma, a green shoot).	2.03	1	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.	2.95	4	chalcogen; nonmetal atom	macronutrient
minfiensine minfiensine: structure in first source	2.49	2
deoxyribose [no description available]	2.02	1	deoxypentose	human metabolite; mouse metabolite; Saccharomyces cerevisiae 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.	2.58	2	boron group element atom; metalloid atom; nonmetal atom	micronutrient
carbocyanines Carbocyanines: Compounds that contain three methine groups. They are frequently used as cationic dyes used for differential staining of biological materials.	2.1	1	cyanine dye; organic iodide salt	fluorochrome
mannich bases Mannich Bases: Ketonic amines prepared from the condensation of a ketone with formaldehyde and ammonia or a primary or secondary amine. A Mannich base can act as the equivalent of an alpha,beta unsaturated ketone in synthesis or can be reduced to form physiologically active amino alcohols.	7.58	2
abiraterone acetate Abiraterone Acetate: An androstene derivative that inhibits STEROID 17-ALPHA-HYDROXYLASE and is used as an ANTINEOPLASTIC AGENT in the treatment of metastatic castration-resistant PROSTATE CANCER.. abiraterone acetate : A sterol ester obtained by formal condensation of the 3-hydroxy group of abiraterone with the carboxy group of acetic acid. A prodrug that is converted in vivo into abiraterone. Used for treatment of metastatic castrate-resistant prostate cancer.	2.41	1	pyridines; sterol ester	antineoplastic agent; EC 1.14.99.9 (steroid 17alpha-monooxygenase) inhibitor; prodrug
flustramine c flustramine C: structure in first source	2.06	1
stephacidin a stephacidin A: from Aspergillus ochraceus; structure in first source	7.07	1
stachybotrin c stachybotrin C: isolated from Stachybotrys parvispora; structure in first source	2.03	1
kapakahine f kapakahine F: from the marine sponge Cribrochalina olemda; structure in first source	2.05	1
asperazine asperazine: structure in first source	7.41	1
losartan potassium Erythropoietin: Glycoprotein hormone, secreted chiefly by the KIDNEY in the adult and the LIVER in the FETUS, that acts on erythroid stem cells of the BONE MARROW to stimulate proliferation and differentiation.	2.01	1
titanocene titanocene: C10-H10-Ti. titanocene : A bis(eta(5)-cyclopentadienyl)metal(II) having Ti(II) as the metal(II) species. The parent of the class of titanonocenes.	7.04	1
mdv 3100 [no description available]	2.15	1	(trifluoromethyl)benzenes; benzamides; imidazolidinone; monofluorobenzenes; nitrile; thiocarbonyl compound	androgen antagonist; antineoplastic agent
oligonucleotides [no description available]	2.25	1
hoe 33342 bisbenzimide ethoxide trihydrochloride: benzimidazole fluorescent dye	2.08	1
5-n-acetylardeemin 5-N-acetylardeemin: structure given in first source; reverses multiple drug resistance in tumor cells and potentiates cyctotoxicity of vinblastine; from Aspergillus fischeri var. brasiliensis	2.06	1
sodium nitrite Sodium Nitrite: Nitrous acid sodium salt. Used in many industrial processes, in meat curing, coloring, and preserving, and as a reagent in ANALYTICAL CHEMISTRY TECHNIQUES. It is used therapeutically as an antidote in cyanide poisoning. The compound is toxic and mutagenic and will react in vivo with secondary or tertiary amines thereby producing highly carcinogenic nitrosamines.. sodium nitrite : An inorganic sodium salt having nitrite as the counterion. Used as a food preservative and antidote to cyanide poisoning.	2.15	1	inorganic sodium salt; nitrite salt	antidote to cyanide poisoning; antihypertensive agent; antimicrobial food preservative; food antioxidant; poison
merocyanine dye merocyanine dye: fluorescent dye used for studying axons 2 position on pyrimidine ring may be S or O; RN given refers to Na salt; structure	2.5	2
communesin f communesin F: structure in first source	2.06	1
vincorine vincorine: structure in first source	2.06	1
piperidines Piperidines: A family of hexahydropyridines.	4.66	8
nitd 609 NITD 609: an antimalarial and coccidiostat; structure in first source	2.53	2
communesin b communesin B: from ethyl acetate extract of Penicillium sp., derived from the Mediterranean sponge Axinella verrucosa; structure in first source	2.45	2
picrinine picrinine: structure in first source. picrinine : A natural product with formula C20H22N2O3 that is the member of the akuammiline family of alkaloids, first isolated in 1965 from the leaves of Alstonia scholaris.	2.11	1	alkaloid ester; indole alkaloid; methyl ester; organic heteropentacyclic compound; polycyclic ether	analgesic; anti-asthmatic agent; anti-inflammatory agent; antitussive; plant metabolite
aza-pinacol aza-pinacol: structure in first source	2.11	1
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.	3.58	2	benzenes; hydroxycoumarin; methyl ketone
communesin a communesin A: structure in first source	2.06	1
oxaline oxaline: a fungal alkaloid from the culture broth of Penicillium oxalicum; structure in first source. oxaline : An indole alkaloid with a heterotetracyclic skeleton isolated from Penicillium oxalicum and has been shown to exhibit cytotoxic activity.	7.02	1
neoxaline neoxaline: alkaloid isolated from fermentation broth of Aspergillus japonicus	7.02	1
s 8932 [no description available]	2.31	1	aromatic amine; C-nucleoside; carboxylic ester; nitrile; phosphoramidate ester; pyrrolotriazine	anticoronaviral agent; antiviral drug; prodrug
lundurine a lundurine A: originally isolated from Kopsia tenuis; structure in first source	2.1	1	monoterpenoid indole alkaloid
guanine [no description available]	2.13	1	2-aminopurines; oxopurine; purine nucleobase	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
asperazine a asperazine A: from an endophytic fungus Aspergillus niger; structure in first source	7.41	1
dinitrobenzenes Dinitrobenzenes: Benzene derivatives which are substituted with two nitro groups in the ortho, meta or para positions.	2.13	1
stephacidin b stephacidin B: from Aspergillus ochraceus; structure in first source	2.07	1
pyrimidinones Pyrimidinones: Heterocyclic compounds known as 2-pyrimidones (or 2-hydroxypyrimidines) and 4-pyrimidones (or 4-hydroxypyrimidines) with the general formula C4H4N2O.	2.06	1
chloropeptin i chloropeptin I: inhibitor of gp120-CD4 binding; isolated from Streptomyces; structure in first source. chloropeptin I : A heterodetic cyclic peptide consisting of N-acylated trytophan, 3,5-dichloro-4-hydroxyphenylglycine, 4-hydroxyphenylglycine, 3,5-dichloro-4-hydroxyphenylglycyl, tyrosine and 4-hydroxyphenylglycine residues joined in sequence and in which the side-chain of the central 4-hydroxyphenylglycine residue is attached to the side-chain of the tryptophan via a C3-C7 bond and to the side-chain of the tyrosine via an ether bond from C5. It is isolated from the culture broth of Streptomyces and has anti-HIV-1 activity.	2.03	1
phenanthrenes Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.	2	1

Condition	Relationship Strength	Studies
Cancer of Prostate [description not available]	2.9	3
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	2.9	3
2019 Novel Coronavirus Disease [description not available]	2.6	1
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	3.57	2
Congenital Zika Syndrome [description not available]	2.6	1
Zika Virus Infection A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.	2.6	1
AIDS Seroconversion [description not available]	2.6	1
HIV Coinfection [description not available]	2.6	1
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).	2.6	1
Cryptogenic Fibrosing Alveolitis [description not available]	2.6	1
Cirrhosis [description not available]	2.6	1
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	7.6	1
Idiopathic Pulmonary Fibrosis A common interstitial lung disease of unknown etiology, usually occurring between 50-70 years of age. Clinically, it is characterized by an insidious onset of breathlessness with exertion and a nonproductive cough, leading to progressive DYSPNEA. Pathological features show scant interstitial inflammation, patchy collagen fibrosis, prominent fibroblast proliferation foci, and microscopic honeycomb change.	7.6	1
Break-Bone Fever [description not available]	2.21	1
Dengue An acute febrile disease transmitted by the bite of AEDES mosquitoes infected with DENGUE VIRUS. It is self-limiting and characterized by fever, myalgia, headache, and rash. SEVERE DENGUE is a more virulent form of dengue.	2.21	1
Esophageal Squamous Cell Carcinoma A carcinoma that originates usually from cells on the surface of the middle and lower third of the ESOPHAGUS. Tumor cells exhibit typical squamous morphology and form large polypoid lesions. Mutations in RNF6, LZTS1, TGFBR2, DEC1, and WWOX1 genes are associated with this cancer.	7.21	1
Cancer of Esophagus [description not available]	2.21	1
Esophageal Neoplasms Tumors or cancer of the ESOPHAGUS.	2.21	1
Benign Neoplasms [description not available]	4.4	7
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	4.4	7
Allergic Encephalomyelitis [description not available]	2.25	1
Breast Cancer [description not available]	2.52	2
Breast Neoplasms Tumors or cancer of the human BREAST.	2.52	2
Allergic Bronchopulmonary Mycosis [description not available]	3.23	1
Bone Cancer [description not available]	2.15	1
Leucocythaemia [description not available]	2.15	1
Osteogenic Sarcoma [description not available]	2.54	2
Bone Neoplasms Tumors or cancer located in bone tissue or specific BONES.	2.15	1
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)	2.15	1
Osteosarcoma A sarcoma originating in bone-forming cells, affecting the ends of long bones. It is the most common and most malignant of sarcomas of the bones, and occurs chiefly among 10- to 25-year-old youths. (From Stedman, 25th ed)	2.54	2
Cognitive Decline [description not available]	2.15	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.8	3
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	2.15	1
Cognitive Dysfunction Diminished or impaired mental and/or intellectual function.	2.15	1
Carcinoma, Basal Cell, Pigmented [description not available]	2.15	1
Cancer of Skin [description not available]	2.15	1
Carcinoma, Basal Cell A malignant skin neoplasm that seldom metastasizes but has potentialities for local invasion and destruction. Clinically it is divided into types: nodular, cicatricial, morphaic, and erythematoid (pagetoid). They develop on hair-bearing skin, most commonly on sun-exposed areas. Approximately 85% are found on the head and neck area and the remaining 15% on the trunk and limbs. (From DeVita Jr et al., Cancer: Principles & Practice of Oncology, 3d ed, p1471)	2.15	1
Skin Neoplasms Tumors or cancer of the SKIN.	2.15	1
Cardiac Failure [description not available]	2.38	2
Blood Pressure, High [description not available]	2.38	2
Heart Failure A heterogeneous condition in which the heart is unable to pump out sufficient blood to meet the metabolic need of the body. Heart failure can be caused by structural defects, functional abnormalities (VENTRICULAR DYSFUNCTION), or a sudden overload beyond its capacity. Chronic heart failure is more common than acute heart failure which results from sudden insult to cardiac function, such as MYOCARDIAL INFARCTION.	2.38	2
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.	2.38	2
Anasarca [description not available]	2.38	2
Ache [description not available]	2.17	1
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	7.38	2
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	2.17	1
Carcinogenesis The origin, production or development of cancer through genotypic and phenotypic changes which upset the normal balance between cell proliferation and cell death. Carcinogenesis generally requires a constellation of steps, which may occur quickly or over a period of many years.	2.17	1
Extravascular Hemolysis [description not available]	2.53	2
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	2.53	2
Carcinoma, Non-Small Cell Lung [description not available]	2.21	1
B-Cell Lymphoma [description not available]	2.21	1
Carcinoma, Non-Small-Cell Lung A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.	2.21	1
Lymphoma, B-Cell A group of heterogeneous lymphoid tumors generally expressing one or more B-cell antigens or representing malignant transformations of B-lymphocytes.	2.21	1
Lung Adenocarcinoma [description not available]	2.08	1
Adenocarcinoma, Basal Cell [description not available]	2.08	1
Cancer of Lung [description not available]	2.08	1
Adenocarcinoma of Lung A carcinoma originating in the lung and the most common lung cancer type in never-smokers. Malignant cells exhibit distinct features such as glandular epithelial, or tubular morphology. Mutations in KRAS, EGFR, BRAF, and ERBB2 genes are associated with this cancer.	2.08	1
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	2.08	1
Lung Neoplasms Tumors or cancer of the LUNG.	2.08	1
Blood Clot [description not available]	2.1	1
Thrombosis Formation and development of a thrombus or blood clot in the blood vessel.	2.1	1
Acute Confusional Senile Dementia [description not available]	2.11	1
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)	2.11	1
African Sleeping Sickness [description not available]	2.11	1
Trypanosomiasis, African A disease endemic among people and animals in Central Africa. It is caused by various species of trypanosomes, particularly T. gambiense and T. rhodesiense. Its second host is the TSETSE FLY. Involvement of the central nervous system produces African sleeping sickness. Nagana is a rapidly fatal trypanosomiasis of horses and other animals.	2.11	1
Infections, Plasmodium [description not available]	2.53	2
Malaria A protozoan disease caused in humans by four species of the PLASMODIUM genus: PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PLASMODIUM OVALE; and PLASMODIUM MALARIAE; and transmitted by the bite of an infected female mosquito of the genus ANOPHELES. Malaria is endemic in parts of Asia, Africa, Central and South America, Oceania, and certain Caribbean islands. It is characterized by extreme exhaustion associated with paroxysms of high FEVER; SWEATING; shaking CHILLS; and ANEMIA. Malaria in ANIMALS is caused by other species of plasmodia.	2.53	2
Adenoma, Prostatic [description not available]	2.13	1
Prostatic Hyperplasia Increase in constituent cells in the PROSTATE, leading to enlargement of the organ (hypertrophy) and adverse impact on the lower urinary tract function. This can be caused by increased rate of cell proliferation, reduced rate of cell death, or both.	2.13	1
Carcinoma, Epidermoid [description not available]	2.13	1
Cancer of Mouth [description not available]	2.13	1
Carcinoma, Squamous Cell A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)	2.13	1
Mouth Neoplasms Tumors or cancer of the MOUTH.	2.13	1
Community Acquired Infection [description not available]	2.15	1
Innate Inflammatory Response [description not available]	2.13	1
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.	7.13	1
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.	7.13	1
Ulcer A lesion on the surface of the skin or a mucous surface, produced by the sloughing of inflammatory necrotic tissue.	7.13	1
Colitis Gravis [description not available]	2.15	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.	2.15	1
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.05	1
Colorectal Cancer [description not available]	2.05	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.	2.05	1
Polyarthritis [description not available]	2.06	1
Allodynia [description not available]	2.06	1
Arthritis Acute or chronic inflammation of JOINTS.	2.06	1
Electrolytes Substances that dissociate into two or more ions, to some extent, in water. Solutions of electrolytes thus conduct an electric current and can be decomposed by it (ELECTROLYSIS). (Grant & Hackh's Chemical Dictionary, 5th ed)	2.06	1
Arrhythmia [description not available]	2.06	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.	2.06	1
Diabetes Mellitus, Adult-Onset [description not available]	2.08	1
Weight Reduction [description not available]	2.08	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.	2.08	1
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	2.08	1
Weight Loss Decrease in existing BODY WEIGHT.	2.08	1
Heart Disease, Ischemic [description not available]	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
Premenstrual Tension A term used to describe the psychological aspects of PREMENSTRUAL SYNDROME, such as the indescribable tension, depression, hostility, and increased seizure activity in women with seizure disorder.	1.93	1
Premenstrual Syndrome A combination of distressing physical, psychologic, or behavioral changes that occur during the luteal phase of the menstrual cycle. Symptoms of PMS are diverse (such as pain, water-retention, anxiety, cravings, and depression) and they diminish markedly 2 or 3 days after the initiation of menses.	1.93	1
Cirrhosis, Liver [description not available]	1.93	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.	1.93	1
Cardiac Edema [description not available]	6.93	1
Edema, Cardiac Abnormal fluid retention by the body due to impaired cardiac function or heart failure. It is usually characterized by increase in venous and capillary pressure, and swollen legs when standing. It is different from the generalized edema caused by renal dysfunction (NEPHROTIC SYNDROME).	1.93	1
Contracture Prolonged shortening of the muscle or other soft tissue around a joint, preventing movement of the joint.	1.93	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.	7.37	2

indoline

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