Page last updated: 2024-12-05

deoxycytidine monophosphate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Deoxycytidine monophosphate (dCMP) is a nucleotide that serves as a building block for DNA. It is synthesized through the phosphorylation of deoxycytidine, a process catalyzed by the enzyme deoxycytidine kinase. dCMP plays a crucial role in DNA replication and repair. It is incorporated into the growing DNA strand by DNA polymerase. Studies on dCMP focus on its role in DNA synthesis, its potential as a therapeutic target for cancer treatment, and its involvement in various metabolic disorders.'

Deoxycytidine Monophosphate: Deoxycytidine (dihydrogen phosphate). A deoxycytosine nucleotide containing one phosphate group esterified to the deoxyribose moiety in the 2'-,3'- or 5- positions. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

2'-deoxycytosine 5'-monophosphate : A pyrimidine 2'-deoxyribonucleoside 5'-monophosphate having cytosine as the nucleobase. [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]

Cross-References

ID SourceID
PubMed CID13945
CHEMBL ID374699
CHEBI ID15918
SCHEMBL ID48317
MeSH IDM0005999

Synonyms (54)

Synonym
cytidine 5'-(dihydrogen phosphate)
2'-deoxy-5'-cytidylic acid
CHEBI:15918 ,
2'-deoxycytosine 5'-monophosphate
2'-deoxycytidine-5'-monophosphate
2'-deoxycytidine 5'-monophosphate
1032-65-1
deoxycytidylate
C00239
deoxycytidine monophosphate
deoxycytidylic acid
DCMP ,
2'-deoxycytidine 5'-monophosphate, sigma grade, >=95.0%
1NJA
1NJC
DB03798
1NJE
D3673
2'-deoxycytidinemonophosphate
CHEMBL374699
[(2r,3s,5r)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
13085-50-2
2'-deoxycytidine-5'-monophosphoric acid
w7a9174xql ,
1beta-deoxyribofuranosylcytosine-5'-phosphate,d
einecs 213-849-9
unii-w7a9174xql
5'-cytidylic acid, 2'-deoxy-
S3268
2'-deoxycytidine 5'-monophosphate hydrate
AKOS015892753
2'-deoxycytidine-5'-monophosphate free acid
HG1127
deoxycytidine 5'-monophosphate
SCHEMBL48317
deoxycytidine-5'-monophosphoric acid
W-200691
((2r,3s,5r)-5-(4-amino-2-oxopyrimidin-1(2h)-yl)-3-hydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate
mfcd00006546
{[(2r,3s,5r)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
2'-deoxycytidine 5'-monophosphate sodium salt
AS-64039
2_-deoxycytidine 5_-monophosphate
2'-deoxycytidine-5'-monophosphorate
2'-deoxycytidine-5'-phosphate
HY-W009216
deoxycytidine dihydrogen phosphate
Q2742455
CS-W009932
DTXSID20908251
29795-73-1
2'-DEOXYCYTIDINE-5'-MONOPHOSPHATEFREE ACID
oligodeoxycytidylic acid d(pc)3*ammonium
BP-58812

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Differences in pharmacokinetic properties between the antiviral monomers and the heterodimers were evaluated using liposomal formulations of 3H-labelled AZT heterodimers as model compounds."( In vitro anti-human immunodeficiency virus and anti-hepatitis B virus activities and pharmacokinetic properties of heterodinucleoside phosphates containing AZT or ddC.
Kuster, H; Peghini, PA; Schott, H; Schwendener, RA; Zahner, R, 1998
)
0.3
" Plasma HI-113 concentrations were measured by analytical high-performance liquid chromatography and the pharmacokinetic parameters were estimated using the WinNonlin program."( In vivo pharmacokinetics and metabolism of anti-human immunodeficiency virus agent D4T-5'-[p-bromophenyl methoxyalaninyl phosphate] (SAMPIDINE) in mice.
Chen, CL; Uckun, FM; Venkatachalam, TK; Zhu, ZH, 2001
)
0.31

Dosage Studied

ExcerptRelevanceReference
" The amount of GMA-DNA adducts increased with GMA dosage within 0-125 mg/kg dosages, degree of the overall level of GMA-DNA adducts in various organs were kidney > liver > white blood cells > testis."( [Study on GMA-DNA adducts in vivo].
Lei, H; Li, Z; Tan, M; Xu, J; Zuo, J, 1999
)
0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
Escherichia coli metaboliteAny bacterial metabolite produced during a metabolic reaction in Escherichia coli.
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
2'-deoxycytidine phosphate
pyrimidine 2'-deoxyribonucleoside 5'-monophosphate
[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]

Pathways (9)

PathwayProteinsCompounds
Pyrimidine Metabolism2353
beta-Ureidopropionase Deficiency2353
UMP Synthase Deficiency (Orotic Aciduria)2353
Dihydropyrimidinase Deficiency2353
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)2353
Pyrimidine Deoxyribonucleosides Salvage815
Pyrimidine Nucleotides and Nucleosides metabolism ( Pyrimidine Nucleotides and Nucleosides metabolism )4549
ATP + dCMP = ADP + dCDP ( Pyrimidine Nucleotides and Nucleosides metabolism )14
Biochemical pathways: part I0466
Pyrimidine metabolism038

Protein Targets (7)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Thymidylate SynthaseLacticaseibacillus caseiKd54.43000.490033.5180160.0000AID977611
Chain A, Thymidylate SynthaseLacticaseibacillus caseiKd54.43000.490033.5180160.0000AID977611
Chain A, Thymidylate SynthaseLacticaseibacillus caseiKd54.43000.490033.5180160.0000AID977611
Chain A, Thymidylate SynthaseLacticaseibacillus caseiKd54.43000.490033.5180160.0000AID977611
Chain A, Thymidylate SynthaseLacticaseibacillus caseiKd54.43000.490033.5180160.0000AID977611
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

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

Biological Processes (11)

Processvia Protein(s)Taxonomy
'de novo' pyrimidine nucleobase biosynthetic processUMP-CMP kinase Homo sapiens (human)
UMP biosynthetic processUMP-CMP kinase Homo sapiens (human)
UDP biosynthetic processUMP-CMP kinase Homo sapiens (human)
pyrimidine ribonucleotide biosynthetic processUMP-CMP kinase Homo sapiens (human)
nucleobase-containing small molecule interconversionUMP-CMP kinase Homo sapiens (human)
nucleoside monophosphate phosphorylationUMP-CMP kinase Homo sapiens (human)
CDP biosynthetic processUMP-CMP kinase Homo sapiens (human)
pyrimidine nucleotide metabolic processDeoxycytidylate deaminaseHomo sapiens (human)
nucleotide biosynthetic processDeoxycytidylate deaminaseHomo sapiens (human)
nucleoside salvageDeoxycytidylate deaminaseHomo sapiens (human)
cytidine deaminationDeoxycytidylate deaminaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (13)

Processvia Protein(s)Taxonomy
nucleoside diphosphate kinase activityUMP-CMP kinase Homo sapiens (human)
uridine kinase activityUMP-CMP kinase Homo sapiens (human)
ATP bindingUMP-CMP kinase Homo sapiens (human)
UMP kinase activityUMP-CMP kinase Homo sapiens (human)
CMP kinase activityUMP-CMP kinase Homo sapiens (human)
dCMP kinase activityUMP-CMP kinase Homo sapiens (human)
nucleoside monophosphate kinase activityUMP-CMP kinase Homo sapiens (human)
cytidylate kinase activityUMP-CMP kinase Homo sapiens (human)
protein bindingDeoxycytidylate deaminaseHomo sapiens (human)
zinc ion bindingDeoxycytidylate deaminaseHomo sapiens (human)
identical protein bindingDeoxycytidylate deaminaseHomo sapiens (human)
deoxyribonucleoside 5'-monophosphate N-glycosidase activityDeoxycytidylate deaminaseHomo sapiens (human)
dCMP deaminase activityDeoxycytidylate deaminaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
nucleoplasmUMP-CMP kinase Homo sapiens (human)
nucleolusUMP-CMP kinase Homo sapiens (human)
cytosolUMP-CMP kinase Homo sapiens (human)
extracellular exosomeUMP-CMP kinase Homo sapiens (human)
cytoplasmUMP-CMP kinase Homo sapiens (human)
nucleusUMP-CMP kinase Homo sapiens (human)
cytosolDeoxycytidylate deaminaseHomo sapiens (human)
cytoplasmDeoxycytidylate deaminaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID1811Experimentally measured binding affinity data derived from PDB1996Biochemistry, Apr-23, Volume: 35, Issue:16
Partitioning roles of side chains in affinity, orientation, and catalysis with structures for mutant complexes: asparagine-229 in thymidylate synthase.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB1996Biochemistry, Apr-23, Volume: 35, Issue:16
Partitioning roles of side chains in affinity, orientation, and catalysis with structures for mutant complexes: asparagine-229 in thymidylate synthase.
AID612651Activity of recombinant human ADAL1 expressed in Escherichia coli by UV-spectrophotometry2011Journal of medicinal chemistry, Aug-25, Volume: 54, Issue:16
Adenosine deaminase-like protein 1 (ADAL1): characterization and substrate specificity in the hydrolysis of N(6)- or O(6)-substituted purine or 2-aminopurine nucleoside monophosphates.
AID553328Binding affinity to human recombinant UCK by circular dichroism analysis2011Journal of medicinal chemistry, Jan-13, Volume: 54, Issue:1
Novel antiviral C5-substituted pyrimidine acyclic nucleoside phosphonates selected as human thymidylate kinase substrates.
AID431231Ratio of Kcat to Km for cloned deoxycytidylate deaminase in human HepG2 cells by spectrophotometric analysis2008Antimicrobial agents and chemotherapy, Feb, Volume: 52, Issue:2
The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.
AID278935Ratio of Kcat to Km for YMPK activity expressed in Huh7 cells2007Antimicrobial agents and chemotherapy, Feb, Volume: 51, Issue:2
Mechanism of activation of beta-D-2'-deoxy-2'-fluoro-2'-c-methylcytidine and inhibition of hepatitis C virus NS5B RNA polymerase.
AID278934Activity of human YMPK expressed in Huh7 cells assessed as phosphorylation by coupled enzyme assay2007Antimicrobial agents and chemotherapy, Feb, Volume: 51, Issue:2
Mechanism of activation of beta-D-2'-deoxy-2'-fluoro-2'-c-methylcytidine and inhibition of hepatitis C virus NS5B RNA polymerase.
AID431229Activity of cloned deoxycytidylate deaminase in human HepG2 cells by spectrophotometric analysis2008Antimicrobial agents and chemotherapy, Feb, Volume: 52, Issue:2
The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (256)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990107 (41.80)18.7374
1990's57 (22.27)18.2507
2000's46 (17.97)29.6817
2010's33 (12.89)24.3611
2020's13 (5.08)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 34.05

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index34.05 (24.57)
Research Supply Index5.58 (2.92)
Research Growth Index4.45 (4.65)
Search Engine Demand Index45.70 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (34.05)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews9 (3.40%)6.00%
Case Studies3 (1.13%)4.05%
Observational0 (0.00%)0.25%
Other253 (95.47%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]