2-aminopyrimidine profile

2-Aminopyrimidine is a heterocyclic organic compound that serves as a building block for the synthesis of various pharmaceuticals and agrochemicals. It is used as a starting material for the production of drugs such as trimethoprim, a widely used antibiotic, and pyrimethamine, an antimalarial drug. 2-aminopyrimidine is also involved in the synthesis of herbicides, fungicides, and other agricultural chemicals. The compound has been extensively studied due to its biological activity and its potential for use in the development of new drugs and other chemical products. Research efforts have focused on its synthesis, modification, and evaluation of its biological properties, including its anti-inflammatory, antibacterial, and anticancer activities.'

pyrimidin-2-amine : An aminopyrimidine carrying an amino group at position 2. [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]

aminopyrimidine : A member of the class of pyrimidines that is pyrimidine substituted by at least one amino group and its derivatives. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

ID Source	ID
PubMed CID	7978
CHEMBL ID	88580
CHEBI ID	38618
MeSH ID	M0059066

Synonym
AC-15596
aminopyrimidine
pyrimidinamine
einecs 203-648-4
2-pyridiylamine
nsc 1912
ai3-24128
pyrimidine, 1,2-dihydro-2-imine-
CHEMBL88580 ,
1,2-dihydro-2-iminopyrimidine
nsc-1912
2-aminopyrimidine
nsc1912
pyrimidine, 2-amino-
2-pyrimidiylamine
109-12-6
2-pyrimidinamine
pyrimidin-2-ylamine
CHEBI:38618 ,
pyrimidin-2-amine
STK317800
2-aminopyrimidine, 97%
LGA ,
A0412
AKOS000119323
A801969
pyrimidin-2-yl-amine
2-amino-pyrimidine
unii-ob8i17p2g4
ob8i17p2g4 ,
amino pyrimidine
27043-39-6
bdbm50354823
FT-0611272
153824-54-5
AM690
MB00175
amino-pyrimidine
2-amino pyrimidine
pyrimidine-2-amine
pyrimidyl amine
Q-200239
551920-04-8
F3329-0410
mfcd00006089
sulfadiazine impurity a, european pharmacopoeia (ep) reference standard
2-aminopyrimidine, vetec(tm) reagent grade, 97%
pyrimidin-2-amine; sulfadiazine imp. a (pharmeuropa); sulfadiazine impurity a
2(1h)-pyrimidinimine (9ci)
A927973
CS-W020110
iminopyrimidine
2(1h)-pyrimidinimine, (e)- (9ci)
2(1h)-pyrimidinimine, (z)- (9ci)
176773-05-0
176773-04-9
DTXSID70870459
Q27117919
AS-13594
sulfadiazine impurity a [ep impurity]
pyrimidine, 1,2-dihydro-2-imino-
EN300-17309
sulfadiazine impurity a
2-aminpirimidina
2-aminopirimidina
HY-41340

Excerpt	Reference	Relevance
" The results from this study suggest that the Fenton oxidation process could remove sulfadiazine, but also increase solution toxicity due to the presence of more toxic products."	( Chemical oxidation of sulfadiazine by the Fenton process: kinetics, pathways, toxicity evaluation. Li, WJ; Xiao, AG; Yang, JF; Ying, GG; Zhou, SB, 2014)	0.4

Excerpt	Reference	Relevance
" Optimization at the C2 and C4-positions of pyrimidine ring of Cerdulatinib led to the discovery of a potent and orally bioavailable 2,4-diaminopyrimidine-5-carboxamide based JAK3 selective inhibitor (11i)."	( Discovery of diaminopyrimidine-carboxamide derivatives as JAK3 inhibitors. Argade, A; Bahekar, R; Bandyopadhyay, D; Chatterjee, A; Desai, J; Desai, RC; Ghoshdastidar, K; Gite, A; Gite, S; Kumar, J; Mahapatra, J; Panchal, N; Patel, B; Patel, D; Patel, H; S, S; Soman, S; Sundar, R, 2020)	0.56

Class	Description
aminopyrimidine	A member of the class of pyrimidines that is pyrimidine substituted by at least one amino group and its derivatives.
[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)
Botulinum neurotoxin type A	Clostridium botulinum	IC50 (µMol)	4.6000	0.5000	3.1692	7.2000	AID1434686
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Heat shock protein HSP 90-alpha	Homo sapiens (human)	Kd	19.0000	0.0003	0.9488	9.8000	AID621858
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
telomere maintenance via telomerase	Heat shock protein HSP 90-alpha	Homo sapiens (human)
neuron migration	Heat shock protein HSP 90-alpha	Homo sapiens (human)
positive regulation of protein phosphorylation	Heat shock protein HSP 90-alpha	Homo sapiens (human)
activation of innate immune response	Heat shock protein HSP 90-alpha	Homo sapiens (human)
positive regulation of defense response to virus by host	Heat shock protein HSP 90-alpha	Homo sapiens (human)
skeletal muscle contraction	Heat shock protein HSP 90-alpha	Homo sapiens (human)
mitochondrial transport	Heat shock protein HSP 90-alpha	Homo sapiens (human)
response to unfolded protein	Heat shock protein HSP 90-alpha	Homo sapiens (human)
response to heat	Heat shock protein HSP 90-alpha	Homo sapiens (human)
response to cold	Heat shock protein HSP 90-alpha	Homo sapiens (human)
response to xenobiotic stimulus	Heat shock protein HSP 90-alpha	Homo sapiens (human)
response to salt stress	Heat shock protein HSP 90-alpha	Homo sapiens (human)
positive regulation of lamellipodium assembly	Heat shock protein HSP 90-alpha	Homo sapiens (human)
cardiac muscle cell apoptotic process	Heat shock protein HSP 90-alpha	Homo sapiens (human)
regulation of protein ubiquitination	Heat shock protein HSP 90-alpha	Homo sapiens (human)
positive regulation of protein polymerization	Heat shock protein HSP 90-alpha	Homo sapiens (human)
positive regulation of interferon-beta production	Heat shock protein HSP 90-alpha	Homo sapiens (human)
regulation of protein localization	Heat shock protein HSP 90-alpha	Homo sapiens (human)
protein refolding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
response to cocaine	Heat shock protein HSP 90-alpha	Homo sapiens (human)
positive regulation of protein import into nucleus	Heat shock protein HSP 90-alpha	Homo sapiens (human)
regulation of apoptotic process	Heat shock protein HSP 90-alpha	Homo sapiens (human)
regulation of protein-containing complex assembly	Heat shock protein HSP 90-alpha	Homo sapiens (human)
protein unfolding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
response to estrogen	Heat shock protein HSP 90-alpha	Homo sapiens (human)
protein insertion into mitochondrial outer membrane	Heat shock protein HSP 90-alpha	Homo sapiens (human)
positive regulation of nitric oxide biosynthetic process	Heat shock protein HSP 90-alpha	Homo sapiens (human)
positive regulation of protein catabolic process	Heat shock protein HSP 90-alpha	Homo sapiens (human)
positive regulation of cell size	Heat shock protein HSP 90-alpha	Homo sapiens (human)
response to antibiotic	Heat shock protein HSP 90-alpha	Homo sapiens (human)
protein stabilization	Heat shock protein HSP 90-alpha	Homo sapiens (human)
chaperone-mediated protein complex assembly	Heat shock protein HSP 90-alpha	Homo sapiens (human)
positive regulation of cardiac muscle contraction	Heat shock protein HSP 90-alpha	Homo sapiens (human)
chaperone-mediated autophagy	Heat shock protein HSP 90-alpha	Homo sapiens (human)
cellular response to virus	Heat shock protein HSP 90-alpha	Homo sapiens (human)
regulation of postsynaptic membrane neurotransmitter receptor levels	Heat shock protein HSP 90-alpha	Homo sapiens (human)
positive regulation of tau-protein kinase activity	Heat shock protein HSP 90-alpha	Homo sapiens (human)
telomerase holoenzyme complex assembly	Heat shock protein HSP 90-alpha	Homo sapiens (human)
cellular response to heat	Heat shock protein HSP 90-alpha	Homo sapiens (human)
protein folding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
superoxide anion generation	Neutrophil cytosol factor 1	Homo sapiens (human)
protein targeting to membrane	Neutrophil cytosol factor 1	Homo sapiens (human)
superoxide metabolic process	Neutrophil cytosol factor 1	Homo sapiens (human)
cellular defense response	Neutrophil cytosol factor 1	Homo sapiens (human)
cellular response to reactive oxygen species	Neutrophil cytosol factor 1	Homo sapiens (human)
superoxide anion generation	Neutrophil cytosol factor 1	Homo sapiens (human)
innate immune response	Neutrophil cytosol factor 1	Homo sapiens (human)
respiratory burst	Neutrophil cytosol factor 1	Homo sapiens (human)
positive regulation of epidermal growth factor-activated receptor activity	Neutrophil cytosol factor 1	Homo sapiens (human)
positive regulation of DNA-templated transcription	Neutrophil cytosol factor 1	Homo sapiens (human)
positive regulation of JNK cascade	Neutrophil cytosol factor 1	Homo sapiens (human)
positive regulation of phosphatidylinositol 3-kinase/protein kinase B signal transduction	Neutrophil cytosol factor 1	Homo sapiens (human)
regulation of respiratory burst involved in inflammatory response	Neutrophil cytosol factor 1	Homo sapiens (human)
cellular response to cadmium ion	Neutrophil cytosol factor 1	Homo sapiens (human)
cellular response to glucose stimulus	Neutrophil cytosol factor 1	Homo sapiens (human)
cellular response to testosterone stimulus	Neutrophil cytosol factor 1	Homo sapiens (human)
positive regulation of p38MAPK cascade	Neutrophil cytosol factor 1	Homo sapiens (human)
reactive oxygen species biosynthetic process	Neutrophil cytosol factor 1	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
UTP binding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
CTP binding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
RNA binding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
mRNA binding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
protein binding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
ATP binding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
GTP binding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
ATP hydrolysis activity	Heat shock protein HSP 90-alpha	Homo sapiens (human)
sulfonylurea receptor binding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
protein phosphatase binding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
MHC class II protein complex binding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
nitric-oxide synthase regulator activity	Heat shock protein HSP 90-alpha	Homo sapiens (human)
TPR domain binding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
ubiquitin protein ligase binding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
dATP binding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
identical protein binding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
protein homodimerization activity	Heat shock protein HSP 90-alpha	Homo sapiens (human)
histone deacetylase binding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
transmembrane transporter binding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
tau protein binding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
GTPase binding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
Rho GDP-dissociation inhibitor binding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
DNA polymerase binding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
scaffold protein binding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
disordered domain specific binding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
ATP-dependent protein folding chaperone	Heat shock protein HSP 90-alpha	Homo sapiens (human)
protein tyrosine kinase binding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
unfolded protein binding	Heat shock protein HSP 90-alpha	Homo sapiens (human)
protein transmembrane transporter activity	Botulinum neurotoxin type A	Clostridium botulinum
protein binding	Neutrophil cytosol factor 1	Homo sapiens (human)
electron transfer activity	Neutrophil cytosol factor 1	Homo sapiens (human)
superoxide-generating NAD(P)H oxidase activity	Neutrophil cytosol factor 1	Homo sapiens (human)
SH3 domain binding	Neutrophil cytosol factor 1	Homo sapiens (human)
phosphatidylinositol binding	Neutrophil cytosol factor 1	Homo sapiens (human)
phosphatidylinositol-3,4-bisphosphate binding	Neutrophil cytosol factor 1	Homo sapiens (human)
superoxide-generating NADPH oxidase activator activity	Neutrophil cytosol factor 1	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
extracellular region	Heat shock protein HSP 90-alpha	Homo sapiens (human)
nucleus	Heat shock protein HSP 90-alpha	Homo sapiens (human)
nucleoplasm	Heat shock protein HSP 90-alpha	Homo sapiens (human)
cytoplasm	Heat shock protein HSP 90-alpha	Homo sapiens (human)
mitochondrion	Heat shock protein HSP 90-alpha	Homo sapiens (human)
cytosol	Heat shock protein HSP 90-alpha	Homo sapiens (human)
plasma membrane	Heat shock protein HSP 90-alpha	Homo sapiens (human)
cell surface	Heat shock protein HSP 90-alpha	Homo sapiens (human)
membrane	Heat shock protein HSP 90-alpha	Homo sapiens (human)
basolateral plasma membrane	Heat shock protein HSP 90-alpha	Homo sapiens (human)
apical plasma membrane	Heat shock protein HSP 90-alpha	Homo sapiens (human)
brush border membrane	Heat shock protein HSP 90-alpha	Homo sapiens (human)
secretory granule lumen	Heat shock protein HSP 90-alpha	Homo sapiens (human)
melanosome	Heat shock protein HSP 90-alpha	Homo sapiens (human)
neuronal cell body	Heat shock protein HSP 90-alpha	Homo sapiens (human)
lysosomal lumen	Heat shock protein HSP 90-alpha	Homo sapiens (human)
dendritic growth cone	Heat shock protein HSP 90-alpha	Homo sapiens (human)
axonal growth cone	Heat shock protein HSP 90-alpha	Homo sapiens (human)
perinuclear region of cytoplasm	Heat shock protein HSP 90-alpha	Homo sapiens (human)
collagen-containing extracellular matrix	Heat shock protein HSP 90-alpha	Homo sapiens (human)
extracellular exosome	Heat shock protein HSP 90-alpha	Homo sapiens (human)
endocytic vesicle lumen	Heat shock protein HSP 90-alpha	Homo sapiens (human)
sperm mitochondrial sheath	Heat shock protein HSP 90-alpha	Homo sapiens (human)
sperm plasma membrane	Heat shock protein HSP 90-alpha	Homo sapiens (human)
ficolin-1-rich granule lumen	Heat shock protein HSP 90-alpha	Homo sapiens (human)
protein-containing complex	Heat shock protein HSP 90-alpha	Homo sapiens (human)
plasma membrane	Heat shock protein HSP 90-alpha	Homo sapiens (human)
neuronal cell body	Heat shock protein HSP 90-alpha	Homo sapiens (human)
perinuclear region of cytoplasm	Heat shock protein HSP 90-alpha	Homo sapiens (human)
myelin sheath	Heat shock protein HSP 90-alpha	Homo sapiens (human)
cytosol	Heat shock protein HSP 90-alpha	Homo sapiens (human)
nucleus	Heat shock protein HSP 90-alpha	Homo sapiens (human)
cytosol	Neutrophil cytosol factor 1	Homo sapiens (human)
plasma membrane	Neutrophil cytosol factor 1	Homo sapiens (human)
cytoplasmic side of plasma membrane	Neutrophil cytosol factor 1	Homo sapiens (human)
membrane	Neutrophil cytosol factor 1	Homo sapiens (human)
dendrite	Neutrophil cytosol factor 1	Homo sapiens (human)
phagolysosome	Neutrophil cytosol factor 1	Homo sapiens (human)
NADPH oxidase complex	Neutrophil cytosol factor 1	Homo sapiens (human)
neuronal cell body	Neutrophil cytosol factor 1	Homo sapiens (human)
cytoplasm	Neutrophil cytosol factor 1	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Assay ID	Title	Year	Journal	Article
AID1175065	Binding affinity to HIV-1 TAR RNA by Tat-TAR fluorimetric competition assay	2014	Bioorganic & medicinal chemistry letters, Dec-15, Volume: 24, Issue:24	Fragment based search for small molecule inhibitors of HIV-1 Tat-TAR.
AID1582668	Covalent inhibition of recombinant human His-tagged p47phox SH3A-B domain (151 to 285 residues) expressed in Escherichia coli BL21 (DE3) cells interaction with Cy5-p22phox149-162 incubated for 10 mins by fluorescence polarization competition assay	2020	Journal of medicinal chemistry, 02-13, Volume: 63, Issue:3	Developing Inhibitors of the p47phox-p22phox Protein-Protein Interaction by Fragment-Based Drug Discovery.
AID238163	Displacement of PRP-1 peptide from mouse Tec kinase SH3 domain by fluorescence polarization; No binding	2004	Journal of medicinal chemistry, Oct-21, Volume: 47, Issue:22	Identification and specificity studies of small-molecule ligands for SH3 protein domains.
AID53455	Maximal noneffective concentration for inhibition of DNA gyrase using supercoiling assay.	2000	Journal of medicinal chemistry, Jul-13, Volume: 43, Issue:14	Novel inhibitors of DNA gyrase: 3D structure based biased needle screening, hit validation by biophysical methods, and 3D guided optimization. A promising alternative to random screening.
AID1582677	Binding affinity to immobilized recombinant human His-tagged p47phox SH3A-B domain (151 to 285 residues) expressed in Escherichia coli BL21 (DE3) cells assessed as maximal response by SPR assay relative to quinolin-2-amine	2020	Journal of medicinal chemistry, 02-13, Volume: 63, Issue:3	Developing Inhibitors of the p47phox-p22phox Protein-Protein Interaction by Fragment-Based Drug Discovery.
AID17269	Dissociation constant determined by heteronuclear 1H/15N correlation NMR spectroscopy	2000	Journal of medicinal chemistry, Jul-13, Volume: 43, Issue:14	Novel inhibitors of DNA gyrase: 3D structure based biased needle screening, hit validation by biophysical methods, and 3D guided optimization. A promising alternative to random screening.
AID239887	Ionization constant (pKa) for the compound	2004	Journal of medicinal chemistry, Oct-21, Volume: 47, Issue:22	Identification and specificity studies of small-molecule ligands for SH3 protein domains.
AID1434686	Inhibition of protease activity of recombinant full length Clostridium botulinum Hall BoNT/A light chain using SNAP-25 peptide (187 to 203 residues) as substrate after 5 mins by HPLC analysis	2017	Bioorganic & medicinal chemistry letters, 02-01, Volume: 27, Issue:3	A matrix-focused structure-activity and binding site flexibility study of quinolinol inhibitors of botulinum neurotoxin serotype A.
AID1530048	Inhibition of Streptococcus pyogenes SrtA deltaN81 mutant expressed in Escherichia coli BL21(DE3) at 100 uM using Abz-LPETA-Dap(Dnp) as substrate preincubated for 10 mins followed by substrate addition measured every min for 2.5 hrs by fluorimetric assay	2019	European journal of medicinal chemistry, Jan-01, Volume: 161	Identification of potential antivirulence agents by substitution-oriented screening for inhibitors of Streptococcus pyogenes sortase A.
AID621858	Binding affinity to human HSP90alpha assessed as 2D1H-15N chemical shift perturbation by NMR spectroscopy	2011	Bioorganic & medicinal chemistry letters, Oct-01, Volume: 21, Issue:19	Lead generation of heat shock protein 90 inhibitors by a combination of fragment-based approach, virtual screening, and structure-based drug design.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	4 (3.45)	18.7374
1990's	4 (3.45)	18.2507
2000's	13 (11.21)	29.6817
2010's	66 (56.90)	24.3611
2020's	29 (25.00)	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	3 (2.52%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	116 (97.48%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
adenine [no description available]	2.07	1	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
benzaldehyde [no description available]	2.15	1	benzaldehydes	EC 3.1.1.3 (triacylglycerol lipase) inhibitor; EC 3.5.5.1 (nitrilase) inhibitor; flavouring agent; fragrance; odorant receptor agonist; plant metabolite
formic acid formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.	2.1	1	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
cytosine [no description available]	2.64	3	aminopyrimidine; pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	2.31	1	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
imidazole imidazole: RN given refers to parent cpd. 1H-imidazole : An imidazole tautomer which has the migrating hydrogen at position 1.	3.21	1	imidazole
indole [no description available]	2.31	1	indole; polycyclic heteroarene	Escherichia coli metabolite
indoleacetic acid indoleacetic acid: RN given refers to unlabeled parent cpd; structure in Merck Index, 9th ed, #4841. auxin : Any of a group of compounds, both naturally occurring and synthetic, that induce cell elongation in plant stems (from Greek alphaupsilonxialphanuomega, "to grow").. indole-3-acetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.	2.21	1	indole-3-acetic acids; monocarboxylic acid	auxin; human metabolite; mouse metabolite; plant hormone; plant metabolite
melatonin [no description available]	2.21	1	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
n-acetylserotonin N-acetylserotonin : An N-acylserotonin resulting from the formal condensation of the primary amino group of serotonin with the carboxy group of acetic acid.	2.21	1	acetamides; N-acylserotonin; phenols	antioxidant; human metabolite; mouse metabolite; tropomyosin-related kinase B receptor agonist
nickel Nickel: A trace element with the atomic symbol Ni, atomic number 28, and atomic weight 58.69. It is a cofactor of the enzyme UREASE.. nickel ion : A nickel atom having a net electric charge.. nickel atom : Chemical element (nickel group element atom) with atomic number 28.	2.03	1	metal allergen; nickel group element atom	epitope; micronutrient
niacinamide nicotinamide : A pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group.	2.05	1	pyridine alkaloid; pyridinecarboxamide; vitamin B3	anti-inflammatory agent; antioxidant; cofactor; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; Escherichia coli metabolite; geroprotector; human urinary metabolite; metabolite; mouse metabolite; neuroprotective agent; Saccharomyces cerevisiae metabolite; Sir2 inhibitor
oxalic acid Oxalic Acid: A strong dicarboxylic acid occurring in many plants and vegetables. It is produced in the body by metabolism of glyoxylic acid or ascorbic acid. It is not metabolized but excreted in the urine. It is used as an analytical reagent and general reducing agent.. oxalic acid : An alpha,omega-dicarboxylic acid that is ethane substituted by carboxyl groups at positions 1 and 2.	2.1	1	alpha,omega-dicarboxylic acid	algal metabolite; human metabolite; plant metabolite
triphosphoric acid triphosphoric acid: used as water softener, peptizing agent, emulsifier & dispersing agent; ingredient of cleansers; meat preservative; RN given refers to parent cpd; structure	2	1	acyclic phosphorus acid anhydride; phosphorus oxoacid
picolinic acid picolinic acid: iron-chelating agent that inhibits DNA synthesis; may interfere with iron-dependent production of stable free organic radical which is essential for ribonucleotide reductase formation of deoxyribonucleotides; RN given refers to parent cpd; structure in Merck Index, 9th ed, #7206. picolinic acid : A pyridinemonocarboxylic acid in which the carboxy group is located at position 2. It is an intermediate in the metabolism of tryptophan.	2.21	1	pyridinemonocarboxylic acid	human metabolite; MALDI matrix material
pyrazole 1H-pyrazole : The 1H-tautomer of pyrazole.	7.66	2	pyrazole
pyridine azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.	7.05	1	azaarene; mancude organic heteromonocyclic parent; monocyclic heteroarene; pyridines	environmental contaminant; NMR chemical shift reference compound
thymine [no description available]	2.06	1	pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite
tryptophan [no description available]	2.21	1	alpha-amino acid; amino acid zwitterion; aminoalkylindole; aromatic amino acid; polar amino acid	Daphnia magna metabolite
tryptamine [no description available]	2.21	1	aminoalkylindole; aralkylamino compound; indole alkaloid; tryptamines	human metabolite; mouse metabolite; plant metabolite
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	2.52	2	pyrimidine nucleobase; pyrimidone	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; prodrug; Saccharomyces cerevisiae metabolite
1-(1-naphthyl)piperazine 1-(1-naphthyl)piperazine: serotonin agonist; structure given in first source	2.25	1	N-arylpiperazine
4-aminopyridine [no description available]	2.03	1	aminopyridine; aromatic amine	avicide; orphan drug; potassium channel blocker
5-methoxytryptamine 5-Methoxytryptamine: Serotonin derivative proposed as potentiator for hypnotics and sedatives.. 5-methoxytryptamine : A member of the class of tryptamines that is the methyl ether derivative of serotonin.	2.21	1	aromatic ether; primary amino compound; tryptamines	5-hydroxytryptamine 2A receptor agonist; 5-hydroxytryptamine 2B receptor agonist; 5-hydroxytryptamine 2C receptor agonist; antioxidant; cardioprotective agent; human metabolite; mouse metabolite; neuroprotective agent; radiation protective agent; serotonergic agonist
oxyquinoline Oxyquinoline: An antiseptic with mild fungistatic, bacteriostatic, anthelmintic, and amebicidal action. It is also used as a reagent and metal chelator, as a carrier for radio-indium for diagnostic purposes, and its halogenated derivatives are used in addition as topical anti-infective agents and oral antiamebics.. quinolin-8-ol : A monohydroxyquinoline that is quinoline substituted by a hydroxy group at position 8. Its fungicidal properties are used for the control of grey mould on vines and tomatoes.	2.58	2	monohydroxyquinoline	antibacterial agent; antifungal agrochemical; antiseptic drug; iron chelator
theophylline [no description available]	2.21	1	dimethylxanthine	adenosine receptor antagonist; anti-asthmatic drug; anti-inflammatory agent; bronchodilator agent; drug metabolite; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; fungal metabolite; human blood serum metabolite; immunomodulator; muscle relaxant; vasodilator agent
aspirin Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.	2.07	1	benzoic acids; phenyl acetates; salicylates	anticoagulant; antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; EC 1.1.1.188 (prostaglandin-F synthase) inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; plant activator; platelet aggregation inhibitor; prostaglandin antagonist; teratogenic agent
cloxyquin cloxyquin: has antitubercular activity; structure in first source	2.15	1	organochlorine compound; quinolines
deferiprone Deferiprone: A pyridone derivative and iron chelator that is used in the treatment of IRON OVERLOAD in patients with THALASSEMIA.. deferiprone : A member of the class of 4-pyridones that is pyridin-4(1H)-one substituted at positions 1 and 2 by methyl groups and at position 3 by a hydroxy group. A lipid-soluble iron-chelator used for treatment of thalassaemia.	2.25	1	4-pyridones	iron chelator; protective agent
ebselen ebselen : A benzoselenazole that is 1,2-benzoselenazol-3-one carrying an additional phenyl substituent at position 2. Acts as a mimic of glutathione peroxidase.	2.25	1	benzoselenazole	anti-inflammatory drug; antibacterial agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antioxidant; apoptosis inducer; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; EC 3.1.3.25 (inositol-phosphate phosphatase) inhibitor; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; EC 3.5.4.1 (cytosine deaminase) inhibitor; EC 5.1.3.2 (UDP-glucose 4-epimerase) inhibitor; enzyme mimic; ferroptosis inhibitor; genotoxin; hepatoprotective agent; neuroprotective agent; radical scavenger
erythrosine Fluoresceins: A family of spiro(isobenzofuran-1(3H),9'-(9H)xanthen)-3-one derivatives. These are used as dyes, as indicators for various metals, and as fluorescent labels in immunoassays.	1.99	1
flucytosine Flucytosine: A fluorinated cytosine analog that is used as an antifungal agent.. flucytosine : An organofluorine compound that is cytosine that is substituted at position 5 by a fluorine. A prodrug for the antifungal 5-fluorouracil, it is used for the treatment of systemic fungal infections.	2.07	1	aminopyrimidine; nucleoside analogue; organofluorine compound; pyrimidine antifungal drug; pyrimidone	prodrug
flufenamic acid Flufenamic Acid: An anthranilic acid derivative with analgesic, anti-inflammatory, and antipyretic properties. It is used in musculoskeletal and joint disorders and administered by mouth and topically. (From Martindale, The Extra Pharmacopoeia, 30th ed, p16). flufenamic acid : An aromatic amino acid consisting of anthranilic acid carrying an N-(trifluoromethyl)phenyl substituent. An analgesic and anti-inflammatory, it is used in rheumatic disorders.	2.6	1	aromatic amino acid; organofluorine compound	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
guanidine Guanidine: A strong organic base existing primarily as guanidium ions at physiological pH. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed) It is also used in the treatment of myasthenia and as a fluorescent probe in HPLC.. guanidine : An aminocarboxamidine, the parent compound of the guanidines.	2.05	1	carboxamidine; guanidines; one-carbon compound
haloperidol Haloperidol: A phenyl-piperidinyl-butyrophenone that is used primarily to treat SCHIZOPHRENIA and other PSYCHOSES. It is also used in schizoaffective disorder, DELUSIONAL DISORDERS, ballism, and TOURETTE SYNDROME (a drug of choice) and occasionally as adjunctive therapy in INTELLECTUAL DISABILITY and the chorea of HUNTINGTON DISEASE. It is a potent antiemetic and is used in the treatment of intractable HICCUPS. (From AMA Drug Evaluations Annual, 1994, p279). haloperidol : A compound composed of a central piperidine structure with hydroxy and p-chlorophenyl substituents at position 4 and an N-linked p-fluorobutyrophenone moiety.	2.11	1	aromatic ketone; hydroxypiperidine; monochlorobenzenes; organofluorine compound; tertiary alcohol	antidyskinesia agent; antiemetic; dopaminergic antagonist; first generation antipsychotic; serotonergic antagonist
propranolol Propranolol: A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs.. propranolol : A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.	2.21	1	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic
protoporphyrin ix protoporphyrin IX: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7685. protoporphyrin : A cyclic tetrapyrrole that consists of porphyrin bearing four methyl substituents at positions 3, 8, 13 and 17, two vinyl substituents at positions 7 and 12 and two 2-carboxyethyl substituents at positions 2 and 18. The parent of the class of protoporphyrins.	2.07	1
quipazine Quipazine: A pharmacologic congener of serotonin that contracts smooth muscle and has actions similar to those of tricyclic antidepressants. It has been proposed as an oxytocic.	2.25	1	piperazines; pyridines
resorcinol resorcinol: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7951. resorcinol : A benzenediol that is benzene dihydroxylated at positions 1 and 3.	2.55	2	benzenediol; phenolic donor; resorcinols	erythropoietin inhibitor; sensitiser
sulfadiazine Sulfadiazine: One of the short-acting SULFONAMIDES used in combination with PYRIMETHAMINE to treat toxoplasmosis in patients with acquired immunodeficiency syndrome and in newborns with congenital infections.. sulfadiazine : A sulfonamide consisting of pyrimidine with a 4-aminobenzenesulfonamido group at the 2-position.. diazine : The parent structure of the diazines.	8.22	5	pyrimidines; substituted aniline; sulfonamide antibiotic; sulfonamide	antiinfective agent; antimicrobial agent; antiprotozoal drug; coccidiostat; drug allergen; EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; xenobiotic
sulfamonomethoxine Sulfamonomethoxine: Long acting sulfonamide antibacterial agent.	2.21	1	benzenes; sulfonamide
sulfapyridine Sulfapyridine: Antibacterial, potentially toxic, used to treat certain skin diseases.. sulfapyridine : A sulfonamide consisting of pyridine with a 4-aminobenzenesulfonamido group at the 2-position.	2.21	1	pyridines; substituted aniline; sulfonamide antibiotic; sulfonamide	antiinfective agent; dermatologic drug; drug allergen; environmental contaminant; xenobiotic
delavirdine Delavirdine: A potent, non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1.. delavirdine : The amide resulting from the formal condensation of 5-[(methylsulfonyl)amino]-1H-indole-2-carboxylic acid and 4-amino group of 1-[3-(isopropylamino)pyridin-2-yl]piperazine, delavirdine is a non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1. Viral resistance emerges rapidly when delavirdine is used alone, so it is therefore used (as the methanesulfonic acid salt) with other antiretrovirals for combination therapy of HIV infection.	2.6	1	aminopyridine; indolecarboxamide; N-acylpiperazine; sulfonamide	antiviral drug; HIV-1 reverse transcriptase inhibitor
guanidine hydrochloride [no description available]	2.1	1	one-carbon compound; organic chloride salt	protein denaturant
idoxuridine [no description available]	2.17	1	organoiodine compound; pyrimidine 2'-deoxyribonucleoside	antiviral drug; DNA synthesis inhibitor
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.	2.48	2	monohydroxyquinoline; quinolone	bacterial xenobiotic metabolite
aniline [no description available]	2.03	1	anilines; primary arylamine
dimethylformamide Dimethylformamide: A formamide in which the amino hydrogens are replaced by methyl groups.. N,N-dimethylformamide : A member of the class of formamides that is formamide in which the amino hydrogens are replaced by methyl groups.	2.15	1	formamides; volatile organic compound	geroprotector; hepatotoxic agent; polar aprotic solvent
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	7.15	1	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
salicylaldehyde o-hydroxybenzaldehyde: structure in first source	2.03	1	hydroxybenzaldehyde	nematicide; plant metabolite
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	3.21	1	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
quinoline [no description available]	7.76	3	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;	7.1	1	indoledione	EC 1.4.3.4 (monoamine oxidase) inhibitor; plant metabolite
2-naphthylamine 2-Naphthylamine: A naphthalene derivative with carcinogenic action.. 2-naphthylamine : A naphthylamine carrying the amino group at position 2.	2.48	2	naphthylamine	carcinogenic agent
2-methylquinoline 2-methylquinoline: RN given refers to parent cpd. methylquinoline : Any member of the class of quinolines carrying at least one methyl substituent.. quinaldine : A quinoline compound in which the quinoline skeleton is substituted at C-2 with a methyl group.	2.25	1	quinolines
quinaldic acid [no description available]	2.21	1	quinolinemonocarboxylic acid	human metabolite; Saccharomyces cerevisiae metabolite
isophthaloyl dichloride [no description available]	2.08	1
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.	2.31	1	pyrrole; secondary amine
2-aminobenzothiazole [no description available]	2.48	2	benzothiazoles
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.	3.59	2	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
indazoles Indazoles: A group of heterocyclic aromatic organic compounds consisting of the fusion of BENZENE and PYRAZOLES.	2.43	2	indazole
indolizine [no description available]	2.04	1	indolizines; mancude organic heterobicyclic parent
thiazoles [no description available]	2.21	1	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
1,2,4-triazole 1,2,4-triazole: RN given refers to 1H-1,2,4-triazole	2.11	1	1,2,4-triazole
pyrimidine pyrimidine : The parent compound of the pyrimidines; a diazine having the two nitrogens at the 1- and 3-positions.	3.41	1	diazine; pyrimidines	Daphnia magna metabolite
hydrazine diamine : Any polyamine that contains two amino groups.	2.05	1	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
cyanamide Cyanamide: A cyanide compound which has been used as a fertilizer, defoliant and in many manufacturing processes. It often occurs as the calcium salt, sometimes also referred to as cyanamide. The citrated calcium salt is used in the treatment of alcoholism.. cyanamide : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by an amino group.	7.15	1	nitrile; one-carbon compound	EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor
3-aminopyridine [no description available]	2.15	1
indole-3-carbaldehyde indole-3-carbaldehyde: metabolite of tryptophan; structure. indole-3-carbaldehyde : A heteroarenecarbaldehyde that is indole in which the hydrogen at position 3 has been replaced by a formyl group.	2.21	1	heteroarenecarbaldehyde; indole alkaloid; indoles	bacterial metabolite; human xenobiotic metabolite; marine metabolite; plant metabolite
2,4-pyridinedicarboxylic acid lutidinic acid : A pyridinedicarboxylic acid carrying carboxy groups at positions 2 and 4.	2.21	1	pyridinedicarboxylic acid
alpha-aminopyridine alpha-aminopyridine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #485. aminopyridine : Compounds containing a pyridine skeleton substituted by one or more amine groups.	3.78	10
thiophene-2-carboxylate thiophene-2-carboxylic acid : A thiophenecarboxylic acid in which the carboxy group is located at position 2.	2.21	1	thiophenecarboxylic acid
8-aminoquinoline [no description available]	2.25	1
6-aminoquinoline [no description available]	2.25	1
6-hydroxyquinoline quinolin-6-ol : A monohydroxyquinoline that is quinoline substituted by a hydroxy group at position 6.	2.21	1	monohydroxyquinoline
1,2-Dihydroquinolin-2-imine [no description available]	2.48	2	aminoquinoline
5-aminoquinoline [no description available]	2.25	1
8-hydroxy-2-methylquinoline 8-hydroxy-2-methylquinoline: structure in first source	2.15	1	hydroxyquinoline
2-cyclohexen-1-one 2-cyclohexen-1-one: RN given refers to unlabeled cpd with specified locant for double bond. cyclohexenone : The parent compound of the cyclohexenones, composed of cyclohexanone having one double bond in the ring.. cyclohex-2-enone : A cyclohexenone having its C=C double bond at the 2-position.	2.11	1	cyclohexenone
2-aminobenzimidazole 2-aminobenzimidazole: metabolite of benomyl; RN given refers to parent cpd. 2-aminobenzimidazole : A member of the class of benzimidazoles that is benzimidazole in which the hydrogen at position 2 is replaced by an amino group.	2.1	1	benzimidazoles	marine xenobiotic metabolite
pyrrole-2-carboxaldehyde 2-pyrrolecarboxaldehyde: structure in first source. pyrrole-2-carboxaldehyde : A pyrrole carrying a formyl substituent at the 2-position.	2.21	1	1,3-thiazole-2-carbaldehyde; pyrroles
5-methoxyindole 5-methoxyindole: structure in first source	2.21	1	indoles
potassium hydroxide potassium hydroxide: RN given refers to cpd with MF of K-OH	2.31	1	alkali metal hydroxide
isonicotinamide isonicotinamide : A pyridinecarboxamide that is the monocarboxylic acid amide derivative of isonicotinic acid.	7.05	1	pyridinecarboxamide
manganese Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.	2.03	1	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.	2.17	1	metal allergen; nickel group element atom; platinum group metal atom
chromium Chromium: A trace element that plays a role in glucose metabolism. It has the atomic symbol Cr, atomic number 24, and atomic weight 52. According to the Fourth Annual Report on Carcinogens (NTP85-002,1985), chromium and some of its compounds have been listed as known carcinogens.. chromium ion : An chromium atom having a net electric charge.. chromium atom : A chromium group element atom that has atomic number 24.	2.03	1	chromium group element atom; metal allergen	micronutrient
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.	2.11	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.	2.02	1	benzenes; phenyl acetates
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	2.21	1	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
2,4-diaminoquinazoline [no description available]	2.1	1
neocuproine neocuproine: Spectrophotometric determination of copper and ultramicro blood sugar determinations; structure; RN given refers to parent cpd. neocuproine : A member of the class of phenanthrolines that is 1,10-phenanthroline bearing two methyl substituents at positions 2 and 9.	2.21	1	phenanthrolines	chelator; copper chelator
chloranilic acid chloranilic acid: structure	7.15	1
isocytosine 2-amino-4-hydroxypyrimidine : An aminopyrimidine in which the pyrimidine ring bears amino and hydroxy substituents at positions 2 and 4, respectively.	2.21	1	aminopyrimidine; pyrimidine nucleobase; pyrimidone
2,4-diaminopyrimidine 2,6-diaminopyrimidine: structure in first source. pyrimidine-2,4-diamine : An aminopyrimidine in which a pyrimidine nucleus is substituted with amino groups at C-2 and C-4.	2.25	1	aminopyrimidine
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.	2.81	3	1,2,3-triazole
4-fluorobenzaldehyde [no description available]	2.15	1
4-aminoquinoline [no description available]	7.53	2
4-aminopyrimidine [no description available]	4.2	5	aminopyrimidine
n-acetylhistamine N-acetylhistamine : A member of the class of acetamides that is acetamide comprising histamine having an acetyl group attached to the side-chain amino function.	2.21	1	acetamides; imidazoles	human metabolite
6-aminouracil [no description available]	2.07	1	pyrimidone
1-(4-pyridyl)piperazine 1-(4-pyridyl)piperazine: structure in first source	2.25	1
isaxonine isaxonine: promotes nerve growth	6.98	1	aminopyrimidine
indole-2-carboxylic acid [no description available]	2.21	1	indolyl carboxylic acid
1-aminoisoquinoline [no description available]	2.77	3
4-aminopyrazolo(3,4-d)pyrimidine 4-aminopyrazolo(3,4-d)pyrimidine: adenine analog which suppresses growth of E coli & Bacillus cereus; inhibits cell growth & purine biosynthesis in rat hepatoma	2.07	1
dimethylformamide-dimethylacetal dimethylformamide-dimethylacetal: RN given refers to unlabeled cpd; structure. N,N-dimethylformamide dimethyl acetal : An acetal obtained by formal condensation of N,N-dimethylformamide with methanol. N,N-dimethylformamide dimethyl acetal is a derivatisation agent used in gas-chromatography applications	2.15	1	acetal; tertiary amino compound	chromatographic reagent
2-aminopyrazine [no description available]	2.06	1	pyrazines
4-amino-2-methylquinoline 4-amino-2-methylquinoline: used to induce miniature endplate potentials	2.25	1
2-aminoimidazole 2-aminoimidazole: from catabolism of arginine	2.06	1
5-chloroindole-2-carboxylate 5-chloroindole-2-carboxylate: N-methyl-D-aspartate glycine site antagonist	2.21	1	indolyl carboxylic acid
fibrinogen Fibrinogen: Plasma glycoprotein clotted by thrombin, composed of a dimer of three non-identical pairs of polypeptide chains (alpha, beta, gamma) held together by disulfide bonds. Fibrinogen clotting is a sol-gel change involving complex molecular arrangements: whereas fibrinogen is cleaved by thrombin to form polypeptides A and B, the proteolytic action of other enzymes yields different fibrinogen degradation products.. D-iditol : The D-enantiomer of iditol.	2.17	1	iditol	fungal metabolite
4,5-dichlorophthalic acid [no description available]	7.05	1
benzo(b)thiophene-2-carboxylic acid benzo(b)thiophene-2-carboxylic acid: for prevention of osteoporosis; structure given in first source	2.21	1
hydroxybenzindazole hydroxybenzindazole: structure	2.06	1
epibatidine epibatidine: a powerful, though toxic, pain killer produced by the poison arrow frog, Epipedobates tricolor; structure given in first source; more potent than morphine but acts at nicotine rather than opiate receptors	2.1	1
tryptoline tryptoline: neurotoxic factor that may be involved in development of Parkinson's disease; enzymatic prep from human brain converts tryptamine to tryptoline; RN given refers to parent cpd; structure	2.21	1	beta-carbolines
imidazole-4-acetic acid hydrochloride [no description available]	2.21	1
fenton's reagent Fenton's reagent: used for oxidizing sugars & alcohols	2.1	1
carbodiimides Carbodiimides: Compounds with the general formula RN=C=NR, where R is a hydrocarbyl group.. methanediimine : A carbodiimide in which both nitrogens are unsubstituted.	7.05	1	carbodiimide
zinc hematoporphyrin [no description available]	2.01	1
sorafenib [no description available]	2.31	1	(trifluoromethyl)benzenes; aromatic ether; monochlorobenzenes; phenylureas; pyridinecarboxamide	angiogenesis inhibitor; anticoronaviral agent; antineoplastic agent; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; ferroptosis inducer; tyrosine kinase inhibitor
5-iodouridine 5-iodouridine: RN given refers to unlabeled cpd	2.17	1
thiobarbituric acid thiobarbituric acid: RN given refers to parent cpd. 2-thiobarbituric acid : A barbiturate, the structure of which is that of barbituric acid in which the oxygen at C-2 is replaced by sulfur.	2.11	1	barbiturates	allergen; reagent
nadp [no description available]	1.98	1
bacteriochlorophylls Bacteriochlorophylls: Pyrrole containing pigments found in photosynthetic bacteria.	2.01	1
tanespimycin CP 127374: analog of herbimycin A	2.06	1	1,4-benzoquinones; ansamycin; carbamate ester; organic heterobicyclic compound; secondary amino compound	antineoplastic agent; apoptosis inducer; Hsp90 inhibitor
crizotinib Crizotinib: A piperidine and aminopyridine derivative that acts as an inhibitor of RECEPTOR PROTEIN-TYROSINE KINASES, including ANAPLASTIC LYMPHOMA KINASE (ALK) and HEPATOCYTE GROWTH FACTOR RECEPTOR (HGFR; c-Met). It is used in the treatment of NON-SMALL CELL LUNG CANCER.. crizotinib : A 3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[1-(piperidin-4-yl)pyrazol-4-yl]pyridin-2-amine that has R configuration at the chiral centre. The active enantiomer, it acts as a kinase inhibitor and is used for the treatment of patients with locally advanced or metastatic non-small cell lung cancer (NSCLC)	2.17	1	3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[1-(piperidin-4-yl)pyrazol-4-yl]pyridin-2-amine	antineoplastic agent; biomarker; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor
jaw [no description available]	3.21	1	indolecarboxamide
oligonucleotides [no description available]	2.17	1
heme Heme: The color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins.. ferroheme : Any iron(II)--porphyrin coordination complex.. ferroheme b : Heme b in which the iron has oxidation state +2.. heme : A heme is any tetrapyrrolic chelate of iron.	2.07	1
novobiocin Novobiocin: An antibiotic compound derived from Streptomyces niveus. It has a chemical structure similar to coumarin. Novobiocin binds to DNA gyrase, and blocks adenosine triphosphatase (ATPase) activity. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p189). novobiocin : A coumarin-derived antibiotic obtained from Streptomyces niveus.	2	1	carbamate ester; ether; hexoside; hydroxycoumarin; monocarboxylic acid amide; monosaccharide derivative; phenols	antibacterial agent; antimicrobial agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; Escherichia coli metabolite; hepatoprotective agent
cc-292 spebrutinib: inhibits Bruton's tyrosine kinase; structure in first source	2.6	1

Condition	Relationship Strength	Studies
Benign Neoplasms [description not available]	3.76	3
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.	3.76	3
Cancer of Pancreas [description not available]	3.33	4
Pancreatic Neoplasms Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).	3.33	4
Acute Myelogenous Leukemia [description not available]	3.61	5
Leukemia, Myeloid, Acute Clonal expansion of myeloid blasts in bone marrow, blood, and other tissue. Myeloid leukemias develop from changes in cells that normally produce NEUTROPHILS; BASOPHILS; EOSINOPHILS; and MONOCYTES.	3.61	5
Acute Promyelocytic Leukemia [description not available]	2.21	1
Leukemia, Promyelocytic, Acute An acute myeloid leukemia in which abnormal PROMYELOCYTES predominate. It is frequently associated with DISSEMINATED INTRAVASCULAR COAGULATION.	2.21	1
Adjuvant Arthritis [description not available]	2.25	1
Acute Confusional Senile Dementia [description not available]	2.61	2
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)	2.61	2
Hepatocellular Carcinoma [description not available]	2.72	2
Cancer of Liver [description not available]	2.72	2
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	2.72	2
Liver Neoplasms Tumors or cancer of the LIVER.	2.72	2
African Lymphoma [description not available]	2.31	1
Burkitt Lymphoma A form of undifferentiated malignant LYMPHOMA usually found in central Africa, but also reported in other parts of the world. It is commonly manifested as a large osteolytic lesion in the jaw or as an abdominal mass. B-cell antigens are expressed on the immature cells that make up the tumor in virtually all cases of Burkitt lymphoma. The Epstein-Barr virus (HERPESVIRUS 4, HUMAN) has been isolated from Burkitt lymphoma cases in Africa and it is implicated as the causative agent in these cases; however, most non-African cases are EBV-negative.	2.31	1
Lung Injury, Acute [description not available]	2.31	1
Innate Inflammatory Response [description not available]	3.5	2
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	3.5	2
Acute Lung Injury A condition of lung damage that is characterized by bilateral pulmonary infiltrates (PULMONARY EDEMA) rich in NEUTROPHILS, and in the absence of clinical HEART FAILURE. This can represent a spectrum of pulmonary lesions, endothelial and epithelial, due to numerous factors (physical, chemical, or biological).	2.31	1
Protein Aggregation, Pathological A biochemical phenomenon in which misfolded proteins aggregate either intra- or extracellularly. Triggered by factors such as MUTATION; POST-TRANSLATIONAL MODIFICATIONS, and environmental stress, it is generally associated with ALZHEIMER DISEASE; PARKINSON DISEASE; HUNTINGTON DISEASE; and TYPE 2 DIABETES MELLITUS.	2.17	1
Cancer of Lung [description not available]	2.17	1
Lung Neoplasms Tumors or cancer of the LUNG.	2.17	1
Epithelial Ovarian Cancer [description not available]	2.21	1
Cancer of Ovary [description not available]	2.21	1
Carcinoma, Ovarian Epithelial A malignant neoplasm that originates in cells on the surface EPITHELIUM of the ovary and is the most common form of ovarian cancer. There are five histologic subtypes: papillary serous, endometrioid, mucinous, clear cell, and transitional cell. Mutations in BRCA1, OPCML, PRKN, PIK3CA, AKT1, CTNNB1, RRAS2, and CDH1 genes are associated with this cancer.	2.21	1
Ovarian Neoplasms Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.	2.21	1
Infections, Plasmodium [description not available]	2.1	1
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.	7.1	1
Anochlesia [description not available]	2.11	1
Hutchinson Gilford Progeria Syndrome [description not available]	2.13	1
Progeria An abnormal congenital condition, associated with defects in the LAMIN TYPE A gene, which is characterized by premature aging in children, where all the changes of cell senescence occur. It is manifested by premature graying; hair loss; hearing loss (DEAFNESS); cataracts (CATARACT); ARTHRITIS; OSTEOPOROSIS; DIABETES MELLITUS; atrophy of subcutaneous fat; skeletal hypoplasia; elevated urinary HYALURONIC ACID; and accelerated ATHEROSCLEROSIS. Many affected individuals develop malignant tumors, especially SARCOMA.	2.13	1
Hyperplasia An increase in the number of cells in a tissue or organ without tumor formation. It differs from HYPERTROPHY, which is an increase in bulk without an increase in the number of cells.	2.04	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.96	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	1.99	1

2-aminopyrimidine

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