5-methylcytidine profile

5-methylcytidine is a modified nucleoside found in DNA and RNA. It is formed by the methylation of the cytosine base at the 5' position. This modification is catalyzed by DNA methyltransferases (DNMTs) in DNA and RNA methyltransferases (RNMTs) in RNA. 5-methylcytidine plays a crucial role in various biological processes, including gene regulation, development, and immunity. In DNA, 5-methylcytidine is a key epigenetic mark that can influence gene expression without altering the underlying DNA sequence. Its presence in CpG dinucleotides is associated with gene silencing, while its absence is often linked to gene activation. 5-methylcytidine in RNA is also implicated in gene regulation and other cellular processes. Its synthesis and function are currently under intense research, as it is believed to be involved in various diseases, including cancer. Research on 5-methylcytidine focuses on understanding its role in gene regulation, disease pathogenesis, and potential therapeutic applications.'

ID Source	ID
PubMed CID	92918
CHEMBL ID	72086
CHEBI ID	20607
SCHEMBL ID	41572
MeSH ID	M0066660

Synonym
CHEMBL72086
AKOS015841917
4-amino-1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidin-2-one
5-methylcytidine
2140-61-6
5-methylcytidine, >=99%
CHEBI:20607 ,
M1931
4-amino-1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidin-2-one
5-methyl-cytidine
A815317
nsc 363933
einecs 218-390-8
unii-tl9pb228dc
tl9pb228dc ,
AKOS015896918
BRD-K65963527-001-01-8
S6138
AM83948
SCHEMBL41572
J-700100
4-amino-1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidin-2(1h)-one
4-amino-1-.beta.-d-arabinofuranosyl-5-methylpyrimidin-2(1h)-one
cytarabine impurity i [ep impurity]
cytidine, 5-methyl-
AC-32357
bdbm200216
4-amino-1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2-dihydropyrimidin-2-one
adenosine receptor agonist, 13
HY-113135
CS-0061684
DS-8104
Q238546
DTXSID401016977
C74035
PD018047

Excerpt	Relevance	Reference
" This inverse dose-response relationship mimics the previously reported effect of 5-methyl cytidine on mammary tumour growth in C3H mice."	( Inhibition of urethan induced lung tumour growth in strain A mice by 5-methyl cytidine. Theiss, JC, 1980)	0.26

Class	Description
methylcytidine	Any member of the class of cytidines that is cytidine substituted by at least one methyl group.
[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)
Adenosine receptor A3	Homo sapiens (human)	Ki	8.0200	0.0000	0.9306	10.0000	AID1802102
Adenosine receptor A2a	Homo sapiens (human)	Ki	8.0200	0.0000	1.0609	9.7920	AID1802102
Adenosine receptor A1	Homo sapiens (human)	Ki	8.0200	0.0002	0.9316	10.0000	AID1802102
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
inflammatory response	Adenosine receptor A3	Homo sapiens (human)
signal transduction	Adenosine receptor A3	Homo sapiens (human)
activation of adenylate cyclase activity	Adenosine receptor A3	Homo sapiens (human)
regulation of heart contraction	Adenosine receptor A3	Homo sapiens (human)
negative regulation of cell population proliferation	Adenosine receptor A3	Homo sapiens (human)
response to wounding	Adenosine receptor A3	Homo sapiens (human)
regulation of norepinephrine secretion	Adenosine receptor A3	Homo sapiens (human)
negative regulation of cell migration	Adenosine receptor A3	Homo sapiens (human)
negative regulation of NF-kappaB transcription factor activity	Adenosine receptor A3	Homo sapiens (human)
presynaptic modulation of chemical synaptic transmission	Adenosine receptor A3	Homo sapiens (human)
G protein-coupled adenosine receptor signaling pathway	Adenosine receptor A3	Homo sapiens (human)
synaptic transmission, dopaminergic	Adenosine receptor A2a	Homo sapiens (human)
response to amphetamine	Adenosine receptor A2a	Homo sapiens (human)
regulation of DNA-templated transcription	Adenosine receptor A2a	Homo sapiens (human)
phagocytosis	Adenosine receptor A2a	Homo sapiens (human)
apoptotic process	Adenosine receptor A2a	Homo sapiens (human)
inflammatory response	Adenosine receptor A2a	Homo sapiens (human)
cellular defense response	Adenosine receptor A2a	Homo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathway	Adenosine receptor A2a	Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathway	Adenosine receptor A2a	Homo sapiens (human)
protein kinase C-activating G protein-coupled receptor signaling pathway	Adenosine receptor A2a	Homo sapiens (human)
cell-cell signaling	Adenosine receptor A2a	Homo sapiens (human)
synaptic transmission, cholinergic	Adenosine receptor A2a	Homo sapiens (human)
central nervous system development	Adenosine receptor A2a	Homo sapiens (human)
blood coagulation	Adenosine receptor A2a	Homo sapiens (human)
sensory perception	Adenosine receptor A2a	Homo sapiens (human)
locomotory behavior	Adenosine receptor A2a	Homo sapiens (human)
blood circulation	Adenosine receptor A2a	Homo sapiens (human)
negative regulation of cell population proliferation	Adenosine receptor A2a	Homo sapiens (human)
response to xenobiotic stimulus	Adenosine receptor A2a	Homo sapiens (human)
response to inorganic substance	Adenosine receptor A2a	Homo sapiens (human)
positive regulation of glutamate secretion	Adenosine receptor A2a	Homo sapiens (human)
positive regulation of acetylcholine secretion, neurotransmission	Adenosine receptor A2a	Homo sapiens (human)
regulation of norepinephrine secretion	Adenosine receptor A2a	Homo sapiens (human)
response to purine-containing compound	Adenosine receptor A2a	Homo sapiens (human)
response to caffeine	Adenosine receptor A2a	Homo sapiens (human)
positive regulation of synaptic transmission, GABAergic	Adenosine receptor A2a	Homo sapiens (human)
synaptic transmission, glutamatergic	Adenosine receptor A2a	Homo sapiens (human)
positive regulation of urine volume	Adenosine receptor A2a	Homo sapiens (human)
vasodilation	Adenosine receptor A2a	Homo sapiens (human)
eating behavior	Adenosine receptor A2a	Homo sapiens (human)
negative regulation of vascular permeability	Adenosine receptor A2a	Homo sapiens (human)
negative regulation of neuron apoptotic process	Adenosine receptor A2a	Homo sapiens (human)
positive regulation of circadian sleep/wake cycle, sleep	Adenosine receptor A2a	Homo sapiens (human)
negative regulation of alpha-beta T cell activation	Adenosine receptor A2a	Homo sapiens (human)
astrocyte activation	Adenosine receptor A2a	Homo sapiens (human)
neuron projection morphogenesis	Adenosine receptor A2a	Homo sapiens (human)
positive regulation of protein secretion	Adenosine receptor A2a	Homo sapiens (human)
negative regulation of inflammatory response	Adenosine receptor A2a	Homo sapiens (human)
regulation of mitochondrial membrane potential	Adenosine receptor A2a	Homo sapiens (human)
membrane depolarization	Adenosine receptor A2a	Homo sapiens (human)
regulation of calcium ion transport	Adenosine receptor A2a	Homo sapiens (human)
positive regulation of synaptic transmission, glutamatergic	Adenosine receptor A2a	Homo sapiens (human)
excitatory postsynaptic potential	Adenosine receptor A2a	Homo sapiens (human)
inhibitory postsynaptic potential	Adenosine receptor A2a	Homo sapiens (human)
prepulse inhibition	Adenosine receptor A2a	Homo sapiens (human)
apoptotic signaling pathway	Adenosine receptor A2a	Homo sapiens (human)
presynaptic modulation of chemical synaptic transmission	Adenosine receptor A2a	Homo sapiens (human)
positive regulation of long-term synaptic potentiation	Adenosine receptor A2a	Homo sapiens (human)
positive regulation of apoptotic signaling pathway	Adenosine receptor A2a	Homo sapiens (human)
G protein-coupled adenosine receptor signaling pathway	Adenosine receptor A2a	Homo sapiens (human)
temperature homeostasis	Adenosine receptor A1	Homo sapiens (human)
response to hypoxia	Adenosine receptor A1	Homo sapiens (human)
G protein-coupled adenosine receptor signaling pathway	Adenosine receptor A1	Homo sapiens (human)
regulation of respiratory gaseous exchange by nervous system process	Adenosine receptor A1	Homo sapiens (human)
negative regulation of acute inflammatory response	Adenosine receptor A1	Homo sapiens (human)
negative regulation of leukocyte migration	Adenosine receptor A1	Homo sapiens (human)
positive regulation of peptide secretion	Adenosine receptor A1	Homo sapiens (human)
positive regulation of systemic arterial blood pressure	Adenosine receptor A1	Homo sapiens (human)
negative regulation of systemic arterial blood pressure	Adenosine receptor A1	Homo sapiens (human)
regulation of glomerular filtration	Adenosine receptor A1	Homo sapiens (human)
protein targeting to membrane	Adenosine receptor A1	Homo sapiens (human)
phagocytosis	Adenosine receptor A1	Homo sapiens (human)
inflammatory response	Adenosine receptor A1	Homo sapiens (human)
signal transduction	Adenosine receptor A1	Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathway	Adenosine receptor A1	Homo sapiens (human)
cell-cell signaling	Adenosine receptor A1	Homo sapiens (human)
nervous system development	Adenosine receptor A1	Homo sapiens (human)
negative regulation of cell population proliferation	Adenosine receptor A1	Homo sapiens (human)
response to inorganic substance	Adenosine receptor A1	Homo sapiens (human)
negative regulation of glutamate secretion	Adenosine receptor A1	Homo sapiens (human)
response to purine-containing compound	Adenosine receptor A1	Homo sapiens (human)
lipid catabolic process	Adenosine receptor A1	Homo sapiens (human)
negative regulation of synaptic transmission, GABAergic	Adenosine receptor A1	Homo sapiens (human)
positive regulation of nucleoside transport	Adenosine receptor A1	Homo sapiens (human)
negative regulation of neurotrophin production	Adenosine receptor A1	Homo sapiens (human)
positive regulation of protein dephosphorylation	Adenosine receptor A1	Homo sapiens (human)
vasodilation	Adenosine receptor A1	Homo sapiens (human)
negative regulation of circadian sleep/wake cycle, non-REM sleep	Adenosine receptor A1	Homo sapiens (human)
negative regulation of apoptotic process	Adenosine receptor A1	Homo sapiens (human)
positive regulation of potassium ion transport	Adenosine receptor A1	Homo sapiens (human)
positive regulation of MAPK cascade	Adenosine receptor A1	Homo sapiens (human)
negative regulation of hormone secretion	Adenosine receptor A1	Homo sapiens (human)
cognition	Adenosine receptor A1	Homo sapiens (human)
leukocyte migration	Adenosine receptor A1	Homo sapiens (human)
detection of temperature stimulus involved in sensory perception of pain	Adenosine receptor A1	Homo sapiens (human)
negative regulation of lipid catabolic process	Adenosine receptor A1	Homo sapiens (human)
positive regulation of lipid catabolic process	Adenosine receptor A1	Homo sapiens (human)
regulation of sensory perception of pain	Adenosine receptor A1	Homo sapiens (human)
negative regulation of synaptic transmission, glutamatergic	Adenosine receptor A1	Homo sapiens (human)
fatty acid homeostasis	Adenosine receptor A1	Homo sapiens (human)
excitatory postsynaptic potential	Adenosine receptor A1	Homo sapiens (human)
long-term synaptic depression	Adenosine receptor A1	Homo sapiens (human)
mucus secretion	Adenosine receptor A1	Homo sapiens (human)
negative regulation of mucus secretion	Adenosine receptor A1	Homo sapiens (human)
triglyceride homeostasis	Adenosine receptor A1	Homo sapiens (human)
regulation of cardiac muscle cell contraction	Adenosine receptor A1	Homo sapiens (human)
apoptotic signaling pathway	Adenosine receptor A1	Homo sapiens (human)
regulation of presynaptic cytosolic calcium ion concentration	Adenosine receptor A1	Homo sapiens (human)
negative regulation of long-term synaptic potentiation	Adenosine receptor A1	Homo sapiens (human)
negative regulation of long-term synaptic depression	Adenosine receptor A1	Homo sapiens (human)
G protein-coupled receptor signaling pathway	Adenosine receptor A1	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
G protein-coupled adenosine receptor activity	Adenosine receptor A3	Homo sapiens (human)
G protein-coupled adenosine receptor activity	Adenosine receptor A2a	Homo sapiens (human)
protein binding	Adenosine receptor A2a	Homo sapiens (human)
calmodulin binding	Adenosine receptor A2a	Homo sapiens (human)
lipid binding	Adenosine receptor A2a	Homo sapiens (human)
enzyme binding	Adenosine receptor A2a	Homo sapiens (human)
type 5 metabotropic glutamate receptor binding	Adenosine receptor A2a	Homo sapiens (human)
identical protein binding	Adenosine receptor A2a	Homo sapiens (human)
protein-containing complex binding	Adenosine receptor A2a	Homo sapiens (human)
alpha-actinin binding	Adenosine receptor A2a	Homo sapiens (human)
G protein-coupled receptor binding	Adenosine receptor A1	Homo sapiens (human)
purine nucleoside binding	Adenosine receptor A1	Homo sapiens (human)
protein binding	Adenosine receptor A1	Homo sapiens (human)
heat shock protein binding	Adenosine receptor A1	Homo sapiens (human)
G-protein beta/gamma-subunit complex binding	Adenosine receptor A1	Homo sapiens (human)
heterotrimeric G-protein binding	Adenosine receptor A1	Homo sapiens (human)
protein heterodimerization activity	Adenosine receptor A1	Homo sapiens (human)
G protein-coupled adenosine receptor activity	Adenosine receptor A1	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
plasma membrane	Adenosine receptor A3	Homo sapiens (human)
presynaptic membrane	Adenosine receptor A3	Homo sapiens (human)
Schaffer collateral - CA1 synapse	Adenosine receptor A3	Homo sapiens (human)
dendrite	Adenosine receptor A3	Homo sapiens (human)
plasma membrane	Adenosine receptor A3	Homo sapiens (human)
synapse	Adenosine receptor A3	Homo sapiens (human)
plasma membrane	Adenosine receptor A2a	Homo sapiens (human)
intermediate filament	Adenosine receptor A2a	Homo sapiens (human)
plasma membrane	Adenosine receptor A2a	Homo sapiens (human)
membrane	Adenosine receptor A2a	Homo sapiens (human)
dendrite	Adenosine receptor A2a	Homo sapiens (human)
axolemma	Adenosine receptor A2a	Homo sapiens (human)
asymmetric synapse	Adenosine receptor A2a	Homo sapiens (human)
presynaptic membrane	Adenosine receptor A2a	Homo sapiens (human)
neuronal cell body	Adenosine receptor A2a	Homo sapiens (human)
postsynaptic membrane	Adenosine receptor A2a	Homo sapiens (human)
presynaptic active zone	Adenosine receptor A2a	Homo sapiens (human)
glutamatergic synapse	Adenosine receptor A2a	Homo sapiens (human)
plasma membrane	Adenosine receptor A1	Homo sapiens (human)
plasma membrane	Adenosine receptor A1	Homo sapiens (human)
basolateral plasma membrane	Adenosine receptor A1	Homo sapiens (human)
axolemma	Adenosine receptor A1	Homo sapiens (human)
asymmetric synapse	Adenosine receptor A1	Homo sapiens (human)
presynaptic membrane	Adenosine receptor A1	Homo sapiens (human)
neuronal cell body	Adenosine receptor A1	Homo sapiens (human)
terminal bouton	Adenosine receptor A1	Homo sapiens (human)
dendritic spine	Adenosine receptor A1	Homo sapiens (human)
calyx of Held	Adenosine receptor A1	Homo sapiens (human)
postsynaptic membrane	Adenosine receptor A1	Homo sapiens (human)
presynaptic active zone	Adenosine receptor A1	Homo sapiens (human)
synapse	Adenosine receptor A1	Homo sapiens (human)
dendrite	Adenosine receptor A1	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Assay ID	Title	Year	Journal	Article
AID99187	Inhibition of L1210/arac cell proliferation at 200 ug/mL; IA means Inactive	1989	Journal of medicinal chemistry, Jan, Volume: 32, Issue:1	Synthesis and cytostatic and antiviral activities of 1-beta-D-ribofuranosyl-5-alkylcytosine (5-alkylcytidine) cyclic 3',5'-monophosphates.
AID99156	Inhibition of L1210/0 cell proliferation	1989	Journal of medicinal chemistry, Jan, Volume: 32, Issue:1	Synthesis and cytostatic and antiviral activities of 1-beta-D-ribofuranosyl-5-alkylcytosine (5-alkylcytidine) cyclic 3',5'-monophosphates.
AID216185	Anti-Herpes simplex virus type-1 activity in vero cells using plaque inhibition assay	1999	Journal of medicinal chemistry, Aug-26, Volume: 42, Issue:17	Virtual combinatorial syntheses and computational screening of new potential anti-herpes compounds.
AID1802102	Radioligand Binding Assay from Article 10.1021/acschembio.6b00357: \\Structure-Based Screening of Uncharted Chemical Space for Atypical Adenosine Receptor Agonists\\	2016	ACS chemical biology, 10-21, Volume: 11, Issue:10	Structure-Based Screening of Uncharted Chemical Space for Atypical Adenosine Receptor Agonists.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	14 (13.59)	18.7374
1990's	15 (14.56)	18.2507
2000's	14 (13.59)	29.6817
2010's	44 (42.72)	24.3611
2020's	16 (15.53)	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 (8.57%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	96 (91.43%)	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]	3.23	1	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
adipic acid adipic acid : An alpha,omega-dicarboxylic acid that is the 1,4-dicarboxy derivative of butane.	2	1	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	food acidity regulator; human xenobiotic metabolite
malic acid malic acid : A 2-hydroxydicarboxylic acid that is succinic acid in which one of the hydrogens attached to a carbon is replaced by a hydroxy group.. 2-hydroxydicarboxylic acid : Any dicarboxylic acid carrying a hydroxy group on the carbon atom at position alpha to the carboxy group.	7.17	1	2-hydroxydicarboxylic acid; C4-dicarboxylic acid	food acidity regulator; fundamental metabolite
cytosine [no description available]	4.24	5	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.	2.37	2	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
sulfites Sulfites: Inorganic salts of sulfurous acid.. sulfites : Any sulfurous acid derivative that is a salt or an ester of sulfurous acid.. organosulfonate oxoanion : An organic anion obtained by deprotonation of the sufonate group(s) of any organosulfonic acid.. sulfite : A sulfur oxoanion that is the conjugate base of hydrogen sulfite (H2SO3).	2.11	1	divalent inorganic anion; sulfur oxide; sulfur oxoanion
succinic acid Succinic Acid: A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawley's Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851). succinic acid : An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.	2	1	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
thymine [no description available]	2.01	1	pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	2.01	1	pyrimidine nucleobase; pyrimidone	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; prodrug; Saccharomyces cerevisiae metabolite
urethane [no description available]	1.95	1	carbamate ester	fungal metabolite; mutagen
thymidine [no description available]	2.72	3	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
uridine [no description available]	4.84	10	uridines	drug metabolite; fundamental metabolite; human metabolite
cytidine monophosphate Cytidine Monophosphate: Cytidine (dihydrogen phosphate). A cytosine nucleotide containing one phosphate group esterified to the sugar moiety in the 2', 3' or 5' position.. cytidine 5'-monophosphate : A pyrimidine ribonucleoside 5'-monophosphate having cytosine as the nucleobase.	2.39	2	cytidine 5'-phosphate; pyrimidine ribonucleoside 5'-monophosphate	Escherichia coli metabolite; human metabolite; mouse metabolite
cytidine [no description available]	8.88	98	cytidines	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
phenacyl bromide phenacyl bromide: structure. phenacyl bromide : An alpha-bromoketone that is acetophenone substituted by a bromo group at position 2.	2.06	1	acetophenones; alpha-bromoketone	metabolite
cordycepin [no description available]	2	1	3'-deoxyribonucleoside; adenosines	antimetabolite; nucleoside antibiotic
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	2.47	2	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
formaldoxime formaldoxime: structure in first source. nitrone : A nitrogen ylide obtained by oxygenation of any imine.	2	1
2,6-lutidine 2,6-dimethylpyridine : A member of the class of methylpyridines that is pyridine carrying methyl substituents at positions 2 and 6.	2.02	1	methylpyridines
tropine [no description available]	2	1
azacitidine Azacitidine: A pyrimidine analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent.. 5-azacytidine : An N-glycosyl-1,3,5-triazine that is 4-amino-1,3,5-triazin-2(1H)-one substituted by a beta-D-ribofuranosyl residue via an N-glycosidic linkage. An antineoplastic agent, it is used in the treatment of myeloid leukaemia.	2.54	2	N-glycosyl-1,3,5-triazine; nucleoside analogue	antineoplastic agent
2-aminopurine 2-Aminopurine: A purine that is an isomer of ADENINE (6-aminopurine).. aminopurine : Any purine having at least one amino substituent.. 2-aminopurine : The parent compound of the 2-aminopurines, comprising a purine core carrying an amino substituent at the 2-position.	1.98	1	2-aminopurines; nucleobase analogue	antimetabolite
5-nitrobarbituric acid [no description available]	2	1
deoxycytidine [no description available]	3.14	5	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
deoxyuridine [no description available]	2	1	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
deoxycytidine monophosphate Deoxycytidine Monophosphate: Deoxycytidine (dihydrogen phosphate). A deoxycytosine nucleotide containing one phosphate group esterified to the deoxyribose moiety in the 2'-,3'- or 5- positions.. 2'-deoxycytosine 5'-monophosphate : A pyrimidine 2'-deoxyribonucleoside 5'-monophosphate having cytosine as the nucleobase.	2.01	1	2'-deoxycytidine phosphate; pyrimidine 2'-deoxyribonucleoside 5'-monophosphate	Escherichia coli metabolite; mouse metabolite
pseudouridine [no description available]	5.33	6	pseudouridines	fundamental metabolite
cyclic cmp Cyclic CMP: A cyclic nucleotide formed from CYTIDINE TRIPHOSPHATE by the action of cytidylate cyclase. It is a potential cyclic nucleotide intracellular mediator of signal transductions.. 3',5'-cyclic CMP : A 3',5'-cyclic pyrimidine nucleotide having cytosine as the nucleobase.	1.97	1	3',5'-cyclic pyrimidine nucleotide	human metabolite
3-deazaadenosine 3-deazaadenosine: RN given refers to parent cpd.	2.13	1
osmium Osmium: A very hard, gray, toxic, and nearly infusible metal element, atomic number 76, atomic weight 190.2, symbol Os.	2.17	1	iron group element atom; platinum group metal atom
tungstate [no description available]	7.21	1	divalent inorganic anion; tungsten oxoanion
1-methyladenosine [no description available]	3.79	3	methyladenosine	human metabolite
2,6-diaminopurine 9H-purine-2,6-diamine : A member of the class of 2,6-diaminopurines that is 9H-purine in which the hydrogens at positions 2 and 6 are replaced by amino groups.	1.98	1	2,6-diaminopurines; primary amino compound	antineoplastic agent
zidovudine Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.	2.25	1	azide; pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
ribavirin Rebetron: Rebetron is tradename	2.46	2	1-ribosyltriazole; aromatic amide; monocarboxylic acid amide; primary carboxamide	anticoronaviral agent; antiinfective agent; antimetabolite; antiviral agent; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	6.25	11	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
5-methylcytosine 5-Methylcytosine: A methylated nucleotide base found in eukaryotic DNA. In ANIMALS, the DNA METHYLATION of CYTOSINE to form 5-methylcytosine is found primarily in the palindromic sequence CpG. In PLANTS, the methylated sequence is CpNpGp, where N can be any base.. 5-methylcytosine : A pyrimidine that is a derivative of cytosine, having a methyl group at the 5-position.	4.13	4	methylcytosine; pyrimidines	human metabolite
methylthymidine methylthymidine: RN given refers to N-3-methylthymidine	2.21	1
1-methylinosine 1-methylinosine : Inosine carrying a methyl substituent at position 1 on the hypoxanthine ring.	2	1	inosines	metabolite
phosphoramidic acid phosphoramidic acid: urease inhibitor; RN given refers to parent cpd; structure; do not confuse with phosphoramidites, which are organophosphorus compounds	1.98	1	phosphoric acid derivative
6-methyladenine 6-methyladenine: structure. 6-methyladenine : A methyladenine that is 9H-purin-6-amine substituted by a methyl group at the amino nitrogen.	3.23	1	6-alkylaminopurine; methyladenine	human metabolite
nebularine nebularine: structure. nebularine : A purine ribonucleoside that is 9H-purine attached to a beta-D-ribofuranosyl residue at position 9 via a glycosidic (N-glycosyl) linkage.	2	1	purine ribonucleoside; purines D-ribonucleoside	fungal metabolite
5-nitrouracil 5-nitrouracil: prevents thymidine degradation. 5-nitrouracil : A C-nitro compound consisting of uracil having a nitro group at the 5-position.	2	1	C-nitro compound
5-hydroxymethylcytosine 5-(hydroxymethyl)cytosine : A nucleobase analogue that is cytosine in which the hydrogen at position 5 is replaced by a hydroxymethyl group.	2.9	3	aminopyrimidine; aromatic primary alcohol; nucleobase analogue; pyrimidone	human metabolite; mouse metabolite
2-aminoadenosine [no description available]	1.98	1	purine nucleoside
4'-azidothymidine 4'-azidothymidine: inhibits HIV replication in human lymphocytes	7.25	1
4,4'-azobis(phenol) 4,4'-azobis(phenol): isolated from fungus Agaricus xanthodermus; structure given in first source	2	1
n-methyladenosine N-methyladenosine: is a inhibitor of cell differentiation. N(6)-methyladenosine : A methyladenosine compound with one methyl group attached to N(6) of the adenine nucleobase.	5.75	7	methyladenosine
2'-o-methyluridine [no description available]	2.17	1	methyluridine
2'-o-methyladenosine cordysinin B : A member of the class of adenosines that is adenosine in which the hydroxy group at position 2' is replaced by a methoxy group. It has been isolated from the mycelia of Cordyceps sinensis.	2	1	adenosines; ether	fungal metabolite
deoxy-5-methylcytidylic acid 2'-deoxy-5-methyl-5'-cytidylic acid : A pyrimidine 2'-deoxyribonucleoside 5'-monophosphate having 5-methylcytidine as the nucleobase.	2.01	1	2'-deoxycytidine phosphate; pyrimidine 2'-deoxyribonucleoside 5'-monophosphate
hydrogen sulfite [no description available]	2.11	1	sulfur oxoanion	human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
n-acetylcytidine N(4)-acetylcytidine : Cytidine in which one of the exocyclic amino hydrogens is substituted by an acetyl group.	3.41	1	acetamides; cytidines; secondary carboxamide	metabolite
2'-o-methylcytidine [no description available]	2.72	3	methylcytidine
phosphorodithioic acid dithiophosphoric acid : A phosphorothioic acid that is the phosphoric acid having two of its oxygen atoms replaced by sulfur atoms.	2.15	1	phosphorothioic acid
1-deazaadenosine 1-deazaadenosine: inhibits nucleic acid & protein synthesis; structure given in first source	2.13	1
5-hydroxymethyldeoxycytidine monophosphate 5-hydroxymethyl-2'-deoxycytidine: structure in first source	2.52	2
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	2	1	divalent inorganic anion; phosphite ion
5-methyldeoxycytidine [no description available]	2.7	3	2'-deoxycytidine
ribothymidine ribothymidine : A methyluridine having a single methyl substituent at the 5-position on the uracil ring.	3.31	6	methyluridine	antigen; Escherichia coli metabolite; human metabolite
zeatin Zeatin: An aminopurine factor in plant extracts that induces cell division. (Grant & Hackh's Chemical Dict, 5th ed)	2.01	1	zeatin	plant metabolite
thioguanine anhydrous Thioguanine: An antineoplastic compound which also has antimetabolite action. The drug is used in the therapy of acute leukemia.. tioguanine : A 2-aminopurine that is the 6-thiono derivative of 2-amino-1,9-dihydro-6H-purine. Incorporates into DNA and inhibits synthesis. Used in the treatment of leukaemia.	2.02	1	2-aminopurines	anticoronaviral agent; antimetabolite; antineoplastic agent
thiouridine Thiouridine: A photoactivable URIDINE analog that is used as an affinity label.. 4-thiouridine : A thiouridine in which the oxygen replaced by sulfur is that at C-4.	2.08	1	nucleoside analogue; thiouridine	affinity label; antimetabolite
cystine [no description available]	2.6	1
2-thiouridine [no description available]	2.08	1	nucleoside analogue; thiouridine
7-hydroxycoumarin 7-oxycoumarin: derivatives have anti-oxidant properties. umbelliferone : A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7.	2	1	hydroxycoumarin	fluorescent probe; food component; plant metabolite
sirolimus Sirolimus: A macrolide compound obtained from Streptomyces hygroscopicus that acts by selectively blocking the transcriptional activation of cytokines thereby inhibiting cytokine production. It is bioactive only when bound to IMMUNOPHILINS. Sirolimus is a potent immunosuppressant and possesses both antifungal and antineoplastic properties.. sirolimus : A macrolide lactam isolated from Streptomyces hygroscopicus consisting of a 29-membered ring containing 4 trans double bonds, three of which are conjugated. It is an antibiotic, immunosupressive and antineoplastic agent.	2.08	1	antibiotic antifungal drug; cyclic acetal; cyclic ketone; ether; macrolide lactam; organic heterotricyclic compound; secondary alcohol	antibacterial drug; anticoronaviral agent; antineoplastic agent; bacterial metabolite; geroprotector; immunosuppressive agent; mTOR inhibitor
phosphorus Phosphorus: A non-metal element that has the atomic symbol P, atomic number 15, and atomic weight 31. It is an essential element that takes part in a broad variety of biochemical reactions.	6.97	1	monoatomic phosphorus; nonmetal atom; pnictogen	macronutrient
glucuronyl glucosamine glycan sulfate [no description available]	3.31	1
s-nitroso-n-acetylpenicillamine S-Nitroso-N-Acetylpenicillamine: A sulfur-containing alkyl thionitrite that is one of the NITRIC OXIDE DONORS.	2.02	1	nitroso compound; nitrosothio compound	nitric oxide donor; vasodilator agent
nitrofurantoin Nitrofurantoin: A urinary anti-infective agent effective against most gram-positive and gram-negative organisms. Although sulfonamides and antibiotics are usually the agents of choice for urinary tract infections, nitrofurantoin is widely used for prophylaxis and long-term suppression.. nitrofurantoin : An imidazolidine-2,4-dione that is hydantoin substituted at position 1 by a [(5-nitro-2-furyl)methylene]amino group. An antibiotic that damages bacterial DNA.	2	1	imidazolidine-2,4-dione; nitrofuran antibiotic; organonitrogen heterocyclic antibiotic; organooxygen heterocyclic antibiotic	antibacterial drug; antiinfective agent; hepatotoxic agent
lipid a Lipid A: Lipid A is the biologically active component of lipopolysaccharides. It shows strong endotoxic activity and exhibits immunogenic properties.. lipid A : The glycolipid moiety of bacterial lipopolysaccharide (R can be either hydrogen or a fatty acyl group).	2.15	1	dodecanoate ester; lipid A; tetradecanoate ester	Escherichia coli metabolite
phosphoramidite phosphoramidite: structure in first source. phosphoramidite : A compound with the general formula (RO)2PNR2. Phosphoramidites can be regarded as phosphites that have an NR2 instead of an OH group, or as amides of phosphorous acid.	2.55	2
3-methylcytidine [no description available]	2.42	2	methylcytidine
5-Hydroxymethylcytidine 5-hydroxymethylcytidine: an epigenetic modification marker of DNA and RNA	4.21	4	pyrimidine nucleoside
oligonucleotides [no description available]	2.95	4
anticodon Anticodon: The sequential set of three nucleotides in TRANSFER RNA that interacts with its complement in MESSENGER RNA, the CODON, during translation in the ribosome.	2.68	3
s-adenosylmethionine (R)-S-adenosyl-L-methionine : An S-adenosyl-L-methionine that has R-configuration.. S-adenosyl-L-methionine zwitterion : A zwitterionic tautomer of S-adenosyl-L-methionine arising from shift of the proton from the carboxy group to the amino group.. (R)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has R-configuration; major species at pH 7.3.. (S)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has S-configuration; major species at pH 7.3.. S-adenosyl-L-methionine : A sulfonium compound that is the S-adenosyl derivative of L-methionine. It is an intermediate in the metabolic pathway of methionine.	1.96	1	organic cation; sulfonium compound	coenzyme; cofactor; human metabolite; micronutrient; Mycoplasma genitalium metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
3-methyluridine 3-methyluridine: isolated from normal human urine & is a minor constituent of tRNA form yeast, rat and human liver; structure	2.52	2
deoxyguanosine [no description available]	2.1	1	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanine [no description available]	1.98	1	2-aminopurines; oxopurine; purine nucleobase	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanosine ribonucleoside : Any nucleoside where the sugar component is D-ribose.	2	1	guanosines; purines D-ribonucleoside	fundamental metabolite
inosine [no description available]	3.82	3	inosines; purines D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
2'-o-methylguanosine 2'-O-methylguanosine : Guanosine with the hydrogen on the hydroxyl at position C-2' substituted with a methyl group.	2	1	methylguanosine	metabolite

Condition	Relationship Strength	Studies
Leukemia L 1210 [description not available]	1.97	1
Colorectal Cancer [description not available]	2.31	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.	2.31	1
Benign Neoplasms, Brain [description not available]	2.41	1
Astrocytoma, Grade IV [description not available]	2.41	1
Brain Neoplasms Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.	2.41	1
Glioblastoma A malignant form of astrocytoma histologically characterized by pleomorphism of cells, nuclear atypia, microhemorrhage, and necrosis. They may arise in any region of the central nervous system, with a predilection for the cerebral hemispheres, basal ganglia, and commissural pathways. Clinical presentation most frequently occurs in the fifth or sixth decade of life with focal neurologic signs or seizures.	2.41	1
Cancer of Prostate [description not available]	2.44	2
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	2.44	2
Isochromosomes Metacentric chromosomes produced during MEIOSIS or MITOSIS when the CENTROMERE splits transversely instead of longitudinally. The chromosomes produced by this abnormal division are one chromosome having the two long arms of the original chromosome, but no short arms, and the other chromosome consisting of the two short arms and no long arms. Each of these isochromosomes constitutes a simultaneous duplication and deletion.	2.31	1
Benign Neoplasms [description not available]	4.34	4
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.	4.34	4
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.08	1
Acute Confusional Senile Dementia [description not available]	2.08	1
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	2.48	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)	2.08	1
Genome Instability [description not available]	2.1	1
Follicular Thyroid Carcinoma [description not available]	2.11	1
Familial Nonmedullary Thyroid Cancer [description not available]	2.11	1
Adenoma, Basal Cell [description not available]	2.4	2
Carcinoma, Anaplastic [description not available]	2.42	2
Carcinoma, Papillary A malignant neoplasm characterized by the formation of numerous, irregular, finger-like projections of fibrous stroma that is covered with a surface layer of neoplastic epithelial cells. (Stedman, 25th ed)	2.11	1
Cancer of the Thyroid [description not available]	2.11	1
Adenoma A benign epithelial tumor with a glandular organization.	2.4	2
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	2.42	2
Thyroid Neoplasms Tumors or cancer of the THYROID GLAND.	7.11	1
Adenocarcinoma, Follicular An adenocarcinoma of the thyroid gland, in which the cells are arranged in the form of follicles. (From Dorland, 27th ed)	2.11	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.05	1
Adenocarcinoma, Basal Cell [description not available]	2.05	1
Carcinoma, Epidermoid [description not available]	2.05	1
Cancer of Cervix [description not available]	2.05	1
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	2.05	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)	2.05	1
Uterine Cervical Neoplasms Tumors or cancer of the UTERINE CERVIX.	2.05	1
ALS - Amyotrophic Lateral Sclerosis [description not available]	2.07	1
Amyotrophic Lateral Sclerosis A degenerative disorder affecting upper MOTOR NEURONS in the brain and lower motor neurons in the brain stem and SPINAL CORD. Disease onset is usually after the age of 50 and the process is usually fatal within 3 to 6 years. Clinical manifestations include progressive weakness, atrophy, FASCICULATION, hyperreflexia, DYSARTHRIA, dysphagia, and eventual paralysis of respiratory function. Pathologic features include the replacement of motor neurons with fibrous ASTROCYTES and atrophy of anterior SPINAL NERVE ROOTS and corticospinal tracts. (From Adams et al., Principles of Neurology, 6th ed, pp1089-94)	2.07	1
Airway Remodeling The structural changes in the number, mass, size and/or composition of the airway tissues.	2.08	1
Asthma, Bronchial [description not available]	2.08	1
Asthma A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL).	2.08	1
Chronic Hepatitis C [description not available]	2.02	1
Hepatitis C, Chronic INFLAMMATION of the LIVER in humans that is caused by HEPATITIS C VIRUS lasting six months or more. Chronic hepatitis C can lead to LIVER CIRRHOSIS.	2.02	1
Experimental Neoplasms [description not available]	3.28	2
Carcinoma, Ehrlich Tumor A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.	1.96	1
Cancer of Lung [description not available]	1.95	1
Lung Neoplasms Tumors or cancer of the LUNG.	1.95	1
Hepatitis, Viral, Non-A, Non-B, Parenterally-Transmitted [description not available]	2	1
Hepatitis C INFLAMMATION of the LIVER in humans caused by HEPATITIS C VIRUS, a single-stranded RNA virus. Its incubation period is 30-90 days. Hepatitis C is transmitted primarily by contaminated blood parenterally and is often associated with transfusion and intravenous drug abuse. However, in a significant number of cases, the source of hepatitis C infection is unknown.	2	1
Cell Transformation, Viral An inheritable change in cells manifested by changes in cell division and growth and alterations in cell surface properties. It is induced by infection with a transforming virus.	2	1
Experimental Leukemia [description not available]	1.97	1

5-methylcytidine

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