Information on EC 2.7.1.74 - deoxycytidine kinase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
2.7.1.74
-
RECOMMENDED NAME
GeneOntology No.
deoxycytidine kinase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
NTP + deoxycytidine = NDP + dCMP
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
phospho group transfer
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Metabolic pathways
-
-
purine deoxyribonucleosides salvage
-
-
purine metabolism
-
-
Purine metabolism
-
-
pyrimidine deoxyribonucleosides salvage
-
-
Pyrimidine metabolism
-
-
SYSTEMATIC NAME
IUBMB Comments
NTP:deoxycytidine 5'-phosphotransferase
Cytosine arabinoside can act as acceptor; all natural nucleoside triphosphates (except dCTP) can act as donors.
CAS REGISTRY NUMBER
COMMENTARY hide
9039-45-6
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain KM
-
-
Manually annotated by BRENDA team
strain KM
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Mus musculus C57BL/6J
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2',2'-difluoro-2'-deoxyguanosine + ATP
ADP + 2',2'-difluoro-2'-deoxyguanosine 5'-phosphate
show the reaction diagram
-
-
-
-
?
2'-fluoro-2'-deoxyarabinosylcytidine + ATP
ADP + 2'-fluoro-2'-deoxyarabinosylcytidine 5'-phosphate
show the reaction diagram
-
-
-
-
?
2'-fluoro-2'-deoxycytidine + ATP
ADP + 2'-fluoro-2'-deoxycytidine 5'-phosphate
show the reaction diagram
-
-
-
-
?
2'-O-methyl-cytidine + ATP
ADP + 2'-O-methyl-cytidine 5'-phosphate
show the reaction diagram
-
-
-
-
?
2-chloro-2'-deoxyadenosine + NTP
NDP + 2-chloro-2'-deoxy-AMP
show the reaction diagram
3'-O-methyl-2'-deoxycytidine + ATP
ADP + 3'-O-methyl-2'-deoxycytidine 5'-phosphate
show the reaction diagram
-
-
-
-
?
4'-thio-2'-deoxycytidine + UTP
UDP + 4'-thio-2'-deoxycytidine 5'-phosphate
show the reaction diagram
-
-
-
-
?
4'-thio-beta-D-arabinofuranosylcytosine + UTP
UDP + 4'-thio-beta-D-arabinofuranosylcytosine 5'-phosphate
show the reaction diagram
-
-
-
-
?
9-(beta-D-arabinofuranosyl)-adenine + ATP
9-(beta-D-arabinofuranosyl)-adenine 5'-phosphate + ADP
show the reaction diagram
-
-
-
-
?
9-beta-D-arabinofuranosylguanine + NTP
NDP + 9-beta-D-arabinofuranosylguanine 5'-phosphate
show the reaction diagram
ATP + (-)-beta-2',3'-dideoxy-3'-thiacytidine
ADP + (-)-beta-2',3'-dideoxy-3'-thiacytidine 5'-phosphate
show the reaction diagram
ATP + (E)-5-(2-bromovinyl)-2'-deoxyuridine
ADP + ?
show the reaction diagram
-
substrate of enzyme mutant R104M/D133A, poor substrate of the wild-type enzyme
-
-
?
ATP + 1-(2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl)cytosine
ADP + 1-(2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl)cytosine monophosphate
show the reaction diagram
ATP + 1-(2'-deoxy-2'-fluoro-beta-L-arabinofuranosyl)-5-bromocytosine
ADP + 1-(2'-deoxy-2'-fluoro-beta-L-arabinofuranosyl)-5-bromocytosine monophosphate
show the reaction diagram
ATP + 1-(2'-deoxy-2'-fluoro-beta-L-arabinofuranosyl)-5-chlorocytosine
ADP + 1-(2'-deoxy-2'-fluoro-beta-L-arabinofuranosyl)-5-chlorocytosine monophosphate
show the reaction diagram
ATP + 1-(2'-deoxy-2'-fluoro-beta-L-arabinofuranosyl)-5-methylcytosine
ADP + 1-(2'-deoxy-2'-fluoro-beta-L-arabinofuranosyl)-5-methylcytosine monophosphate
show the reaction diagram
ATP + 1-(2-deoxy-beta-D-ribofuranosyl)-isocarbostyril
ADP + ?
show the reaction diagram
-
poor substrate, 1.4% of the activity with 2'-deoxycytidine
-
-
?
ATP + 1-beta-D-arabinofuranosylcytosine
ADP + 1-beta-D-arabinofuranosylcytosine 5'-phosphate
show the reaction diagram
-
-
-
-
-
ATP + 1-beta-D-arabinosylcytosine
ADP + 1-beta-D-arabinosylcytosine 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + 2',2'-difluoro-2'-deoxycytidine
ADP + 2',2'-difluoro-2'-deoxycytidine 5'-phosphate
show the reaction diagram
-
i.e. gemcitabine
-
-
?
ATP + 2',2'-difluorodeoxycytidine
ADP + 2',2'-difluorodeoxycytidine 5'-monophosphate
show the reaction diagram
-
i.e. gemcitabine
-
-
?
ATP + 2',2'-difluorodeoxycytidine
ADP + 2',2'-difluorodeoxycytidine 5'-phosphate
show the reaction diagram
ATP + 2',2'-difluorodeoxycytidine
ADP + 2',2'-difluorodeoxycytidine monophosphate
show the reaction diagram
ATP + 2',3'-dideoxycytidine
ADP + 2',3'-dideoxycytidine 5'-phosphate
show the reaction diagram
i.e. zalcitabine
-
-
?
ATP + 2'-deoxy-3'-thiacytidine
ADP + 2'-deoxy-3'-thiacytidine 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + 2'-deoxyadenosine
ADP + 2'-deoxyadenosine 5'-phosphate
show the reaction diagram
ATP + 2'-deoxycytidine
ADP + 2'-deoxy-CMP
show the reaction diagram
-
-
-
-
?
ATP + 2'-deoxycytidine
ADP + 2'-deoxycytidine 5'-phosphate
show the reaction diagram
ATP + 2'-deoxycytidine
ADP + 5'-dCMP
show the reaction diagram
ATP + 2'-deoxyguanosine
ADP + 2'-deoxyguanosine 5'-phosphate
show the reaction diagram
ATP + 2,5-difluoro-4-[1-(2-deoxy-beta-L-ribofuranosyl)]-aniline
ADP + ?
show the reaction diagram
-
nucleoside mimic, 14.6% of the activity with 2'-deoxycytidine
-
-
?
ATP + 2-chloro-2'-deoxyadenosine
ADP + 2-chloro-2'-deoxyadenosine 5'-phosphate
show the reaction diagram
ATP + 2-chlorodeoxyadenosine
ADP + 2-chlorodeoxyadenosine 5'-phosphate
show the reaction diagram
-
i.e. cladribine
-
-
?
ATP + 5-(3-pyridyl)-2'-deoxycytidine
ADP + 5-(3-pyridyl)-2'-deoxycytidine 5'-phosphate
show the reaction diagram
-
cytosolic enzyme, poor substrate
-
-
?
ATP + 5-(4-pyridyl)-2'-deoxycytidine
ADP + 5-(4-pyridyl)-2'-deoxycytidine 5'-phosphate
show the reaction diagram
-
cytosolic enzyme, poor substrate
-
-
?
ATP + 5-bromodeoxycytidine
ADP + 5-bromo-dCMP
show the reaction diagram
-
-
-
-
?
ATP + 5-iododeoxycytidine
ADP + 5-iodo-dCMP
show the reaction diagram
-
-
-
-
?
ATP + 5-methyldeoxycytidine
ADP + 5-methyl-dCMP
show the reaction diagram
-
-
-
-
?
ATP + 5-propynyldeoxycytidine
ADP + 5-propynyl-dCMP
show the reaction diagram
-
-
-
-
?
ATP + adenosine
ADP + adenosine 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + arabinosyl adenine
ADP + arabinosyl adenine 5'-phosphate
show the reaction diagram
-
-
-
?
ATP + arabinosyl cytosine
ADP + arabinosyl cytosine 5'-phosphate
show the reaction diagram
ATP + beta-L-2',3'-dideoxy-3'-thiacytidine
ADP + beta-L-2',3'-dideoxy-3'-thiacytidine 5'-phosphate
show the reaction diagram
-
-
-
?
ATP + cladribine
ADP + cladribine 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + clofarabine
ADP + clofarabine 5'-phosphate
show the reaction diagram
ATP + cytarabine
ADP + cytarabine 5'-phosphate
show the reaction diagram
ATP + cytidine
ADP + ?
show the reaction diagram
ATP + cytidine
ADP + cytidine 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + D-2'-deoxycytidine
ADP + D-2'-deoxycytidine 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + D-deoxycytidine
ADP + D-dCMP
show the reaction diagram
-
-
-
-
?
ATP + D-deoxythymidine
ADP + D-dTMP
show the reaction diagram
-
-
-
-
?
ATP + D-deoxyuridine
ADP + D-dUMP
show the reaction diagram
-
-
-
-
?
ATP + deoxyadenosine
ADP + dAMP
show the reaction diagram
ATP + deoxycytidine
ADP + ?
show the reaction diagram
ATP + deoxycytidine
ADP + dCMP
show the reaction diagram
ATP + deoxyguanosine
ADP + dGMP
show the reaction diagram
ATP + dideoxythymidine
ADP + dideoxythymidine 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + difluoro-arabinofuranosyl adenine
ADP + difluoro-arabinofuranosyl adenine 5'-phosphate
show the reaction diagram
i.e. fludarabine
-
-
?
ATP + difluorodeoxycytidine
ADP + difluorodeoxycytidine 5'-phosphate
show the reaction diagram
i.e. gemcitabine
-
-
?
ATP + fludarabine
ADP + fludarabine 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + gemcitabine
ADP + gemcitabine 5'-phosphate
show the reaction diagram
ATP + gemcitabine
ADP + phospho-gemcitabine
show the reaction diagram
-
-
-
-
?
ATP + L-2',3'-dideoxy-3'-thiacytidine
ADP + L-2',3'-dideoxy-3'-thiacytidine 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + L-2'-deoxycytidine
ADP + L-2'-deoxycytidine 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + L-deoxyuridine
ADP + L-dUMP
show the reaction diagram
-
-
-
-
?
ATP + L-thymidine
?
show the reaction diagram
-
human dCK, in addition to being able to phosphorylate both purines and pyrimidines, has the special ability to accept L-nucleosides as substrates
-
-
?
ATP + L-thymidine
ADP + L-dTMP
show the reaction diagram
-
-
-
-
?
ATP + lamivudine
ADP + lamivudine 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + thymidine
ADP + TMP
show the reaction diagram
ATP + troxacitabine
ADP + troxacitabine 5'-phosphate
show the reaction diagram
-
-
-
-
?
beta-D-3'-hydroxymethyl-2',3'dideoxycytidine + ATP
ADP + beta-D-3'-hydroxymethyl-2',3'dideoxycytidine 5'-phosphate
show the reaction diagram
-
-
-
-
?
CTP + 2'-deoxycytidine
CDP + 2'-deoxy-CMP
show the reaction diagram
CTP + deoxycytidine
CDP + dCMP
show the reaction diagram
dATP + deoxycytidine
dADP + dCMP
show the reaction diagram
dCTP + 2'-deoxycytidine
dCDP + 2'-deoxy-CMP
show the reaction diagram
-
only in the absence of ATP
-
-
?
dCTP + deoxycytidine
dCDP + dCMP
show the reaction diagram
dGTP + 2'-deoxycytidine
dGDP + 2'-deoxy-CMP
show the reaction diagram
dGTP + deoxycytidine
dGDP + dCMP
show the reaction diagram
dTTP + 2'-deoxycytidine
dTDP + 2'-deoxy-CMP
show the reaction diagram
dTTP + deoxycytidine
dTDP + dCMP
show the reaction diagram
-
-
-
-
?
dUTP + 2'-deoxycytidine
dUDP + 2'-deoxy-CMP
show the reaction diagram
GTP + 2'-deoxycytidine
GDP + 2'-deoxy-CMP
show the reaction diagram
GTP + deoxycytidine
GDP + dCMP
show the reaction diagram
-
optimal activity with GTP as phosphoryl donor
-
-
?
NTP + (-)-beta-2',3'-dideoxy-3'-thiacytidine
NDP + (-)-beta-2',3'-dideoxy-3'-thiacytidine 5'-phosphate
show the reaction diagram
-
activation of the clinically relevant substrate
-
-
?
NTP + 1-beta-D-arabinofuranosylcytosine
NDP + 1-beta-D-arabinofuranosylcytosine 5'-phosphate
show the reaction diagram
NTP + 1-beta-D-arabinosylcytosine
NDP + 1-beta-D-arabinosylcytosine 5'-phosphate
show the reaction diagram
-
i.e. cytaribine, activation of the pharmaceutically relevant substrate which is commonly used in the treatment of lymphoproliferative malignancies
-
-
?
NTP + 2',2'-difluoro-2'-deoxycytidine
NDP + 2',2'-difluoro-2'-deoxycytidine 5'-phosphate
show the reaction diagram
NTP + 2',2'-difluorodeoxycytidine
NDP + 2',2'-difluorodeoxycytidine 5'-phosphate
show the reaction diagram
NTP + 2',3'-dideoxycytidine
NDP + 2',3'-dideoxycytidine 5'-phosphate
show the reaction diagram
NTP + 2'-deoxy-3'-thiacytidine
NDP + 2'-deoxy-3'-thiacytidine 5'-phosphate
show the reaction diagram
NTP + 2'-deoxyadenosine
NDP + 2'-deoxyadenosine 5'-phosphate
show the reaction diagram
NTP + 2'-deoxycytidine
NDP + 2'-deoxycytidine 5'-phosphate
show the reaction diagram
NTP + 2'-deoxyguanosine
NDP + 2'-deoxyguanosine 5'-phosphate
show the reaction diagram
NTP + 2-chloro-2'-deoxyadenosine
NDP + 2-chloro-2'-deoxyadenosine 5'-phosphate
show the reaction diagram
NTP + 2-chloro-9-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-9H-purin-6-amine
NDP + 2-chloro-9-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-9H-purin-6-amine 5'-phosphate
show the reaction diagram
-
i.e. clofarabine, rate-limiting step in the activation of the prodrug, precursor of an effective chemotherapeutic agent for leukemias and other haematological malignancies
-
-
?
NTP + 9-beta-D-arabinofuranosyl-2-fluoroadenine
NDP + 9-beta-D-arabinofuranosyl-2-fluoroadenine 5'-phosphate
show the reaction diagram
-
-
-
-
?
NTP + 9-beta-D-arabinosyl 2-fluoroadenine
NDP + 9-beta-D-arabinosyl 2-fluoroadenine 5'-phosphate
show the reaction diagram
NTP + 9-beta-D-arabinosyl-2-fluoroadenine
NDP + 9-beta-D-arabinosyl-2-fluoroadenine 5'-phosphate
show the reaction diagram
-
phosphorylation of chemotherapeutically important nucleoside analogues
-
-
?
NTP + beta-D-2'-deoxythioguanosine
NDP + ?
show the reaction diagram
-
not alpha-isomer
-
-
?
NTP + cytosine arabinoside
NDP + cytosine arabinoside 5'-monophosphate
show the reaction diagram
NTP + deoxyadenosine
NDP + dAMP
show the reaction diagram
NTP + deoxycytidine
NDP + dCMP
show the reaction diagram
NTP + deoxyguanosine
NDP + dGMP
show the reaction diagram
NTP + deoxythymidine
NDP + dTMP
show the reaction diagram
-
mitochondrial isozyme, better than deoxycytidine, not cytosolic isozyme I
-
-
?
NTP + deoxyuridine
NDP + dUMP
show the reaction diagram
NTP + troxacitabine
?
show the reaction diagram
-
activation of the clinically relevant substrate
-
-
?
UTP + (-)-beta-2',3'-dideoxy-3'-thiacytidine
UDP + (-)-beta-2',3'-dideoxy-3'-thiacytidine 5'-phosphate
show the reaction diagram
-
-
-
-
?
UTP + 1-beta-D-arabinofuranosylcytosine
UDP + 1-beta-D-arabinofuranosylcytosine 5'-phosphate
show the reaction diagram
-
i.e. cytarabine
-
-
?
UTP + 2',2'-difluorodeoxycytidine
UDP + 2',2'-difluorodeoxycytidine 5'-phosphate
show the reaction diagram
-
i.e. gemcitabine
-
-
?
UTP + 2',3'-dideoxycytidine
UDP + 2',3'-dideoxycytidine 5'-phosphate
show the reaction diagram
UTP + 2'-deoxy-3'-thiacytidine
UDP + 2'-deoxy-3'-thiacytidine 5'-phosphate
show the reaction diagram
UTP + 2'-deoxyadenosine
UDP + 2'-deoxyadenosine 5'-phosphate
show the reaction diagram
UTP + 2'-deoxycytidine
UDP + 2'-deoxy-CMP
show the reaction diagram
UTP + 2'-deoxycytidine
UDP + 2'-deoxycytidine 5'-phosphate
show the reaction diagram
UTP + 2'-deoxyguanosine
UDP + 2'-deoxyguanosine 5'-phosphate
show the reaction diagram
UTP + 2-chloro-2'-deoxyadenosine
UDP + 2-chloro-2'-deoxyadenosine 5'-phosphate
show the reaction diagram
UTP + 2-chlorodeoxyadenosine
UDP + 2-chlorodeoxyadenosine 5'-phosphate
show the reaction diagram
-
i.e. cladribine
-
-
?
UTP + 2-fluoro-9-beta-D-arabinofuranosyladenine
UDP + 2-fluoro-9-beta-D-arabinofuranosyladenine 5'-phosphate
show the reaction diagram
-
i.e. fludarabine
-
-
?
UTP + 9-beta-D-arabinofuranosylguanine
UDP + 9-beta-D-arabinofuranosylguanine 5'-phosphate
show the reaction diagram
-
i.e. nelarabine
-
-
?
UTP + adenosine
UDP + adenosine 5'-phosphate
show the reaction diagram
-
-
-
-
?
UTP + arabinosyl adenine
UDP + arabinosyl adenine 5'-phosphate
show the reaction diagram
-
-
-
?
UTP + arabinosyl cytosine
UDP + arabinosyl cytosine 5'-phosphate
show the reaction diagram
UTP + beta-L-2',3'-dideoxy-3'-thiacytidine
UDP + beta-L-2',3'-dideoxy-3'-thiacytidine 5'-phosphate
show the reaction diagram
-
-
-
?
UTP + beta-L-dioxolane-cytidine
UDP + beta-L-dioxolane-cytidine 5'-phosphate
show the reaction diagram
antitumor drug
-
-
?
UTP + cladribine
UDP + cladribine 5'-phosphate
show the reaction diagram
-
-
-
-
?
UTP + clofarabine
UDP + clofarabine 5'-phosphate
show the reaction diagram
-
-
-
-
?
UTP + cytidine
UDP + cytidine 5'-phosphate
show the reaction diagram
-
-
-
-
?
UTP + D-2'-deoxycytidine
UDP + D-2'-deoxycytidine 5'-phosphate
show the reaction diagram
-
-
-
-
?
UTP + deoxyadenosine
UDP + dAMP
show the reaction diagram
-
-
-
-
?
UTP + deoxycytidine
UDP + dCMP
show the reaction diagram
UTP + deoxyguanosine
UDP + dGMP
show the reaction diagram
-
-
-
-
?
UTP + difluoro-arabinofuranosyl adenine
UDP + difluoro-arabinofuranosyl adenine 5'-phosphate
show the reaction diagram
i.e. fludarabine
-
-
?
UTP + difluorodeoxycytidine
UDP + difluorodeoxycytidine 5'-phosphate
show the reaction diagram
i.e. gemcitabine
-
-
?
UTP + fludarabine
UDP + fludarabine 5'-phosphate
show the reaction diagram
-
-
-
-
?
UTP + fludarabine
UDP + phospho-fludarabine
show the reaction diagram
-
-
-
-
?
UTP + gemcitabine
UDP + gemcitabine 5'-phosphate
show the reaction diagram
-
-
-
-
?
UTP + L-2',3'-dideoxy-3'-thiacytidine
UDP + L-2',3'-dideoxy-3'-thiacytidine 5'-phosphate
show the reaction diagram
-
-
-
-
?
UTP + L-2'-deoxycytidine
UDP + L-2'-deoxycytidine 5'-phosphate
show the reaction diagram
-
-
-
-
?
UTP + troxacitabine
UDP + troxacitabine 5'-phosphate
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
ATP + 2',2'-difluorodeoxycytidine
ADP + 2',2'-difluorodeoxycytidine monophosphate
show the reaction diagram
-
i.e. gemcitabine, transport and metabolism in vivo, overview
-
-
?
ATP + 2'-deoxyadenosine
ADP + 2'-deoxyadenosine 5'-phosphate
show the reaction diagram
ATP + 2'-deoxycytidine
ADP + 2'-deoxycytidine 5'-phosphate
show the reaction diagram
ATP + 2'-deoxyguanosine
ADP + 2'-deoxyguanosine 5'-phosphate
show the reaction diagram
ATP + 2-chlorodeoxyadenosine
ADP + 2-chlorodeoxyadenosine 5'-phosphate
show the reaction diagram
-
i.e. cladribine
-
-
?
ATP + 5-methyldeoxycytidine
ADP + 5-methyl-dCMP
show the reaction diagram
-
-
-
-
?
ATP + cladribine
ADP + cladribine 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + clofarabine
ADP + clofarabine 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + cytarabine
ADP + cytarabine 5'-phosphate
show the reaction diagram
-
drug against acute myeloid and lymphoblastic leukemia
-
-
?
ATP + deoxyadenosine
ADP + dAMP
show the reaction diagram
ATP + deoxycytidine
ADP + ?
show the reaction diagram
ATP + deoxycytidine
ADP + dCMP
show the reaction diagram
ATP + deoxyguanosine
ADP + dGMP
show the reaction diagram
ATP + fludarabine
ADP + fludarabine 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + L-thymidine
?
show the reaction diagram
-
human dCK, in addition to being able to phosphorylate both purines and pyrimidines, has the special ability to accept L-nucleosides as substrates
-
-
?
NTP + (-)-beta-2',3'-dideoxy-3'-thiacytidine
NDP + (-)-beta-2',3'-dideoxy-3'-thiacytidine 5'-phosphate
show the reaction diagram
-
activation of the clinically relevant substrate
-
-
?
NTP + 1-beta-D-arabinofuranosylcytosine
NDP + 1-beta-D-arabinofuranosylcytosine 5'-phosphate
show the reaction diagram
NTP + 1-beta-D-arabinosylcytosine
NDP + 1-beta-D-arabinosylcytosine 5'-phosphate
show the reaction diagram
-
i.e. cytaribine, activation of the pharmaceutically relevant substrate which is commonly used in the treatment of lymphoproliferative malignancies
-
-
?
NTP + 2',2'-difluorodeoxycytidine
NDP + 2',2'-difluorodeoxycytidine 5'-phosphate
show the reaction diagram
NTP + 2',3'-dideoxycytidine
NDP + 2',3'-dideoxycytidine 5'-phosphate
show the reaction diagram
NTP + 2'-deoxy-3'-thiacytidine
NDP + 2'-deoxy-3'-thiacytidine 5'-phosphate
show the reaction diagram
NTP + 2'-deoxyadenosine
NDP + 2'-deoxyadenosine 5'-phosphate
show the reaction diagram
NTP + 2'-deoxycytidine
NDP + 2'-deoxycytidine 5'-phosphate
show the reaction diagram
NTP + 2'-deoxyguanosine
NDP + 2'-deoxyguanosine 5'-phosphate
show the reaction diagram
NTP + 2-chloro-2'-deoxyadenosine
NDP + 2-chloro-2'-deoxyadenosine 5'-phosphate
show the reaction diagram
NTP + 2-chloro-9-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-9H-purin-6-amine
NDP + 2-chloro-9-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-9H-purin-6-amine 5'-phosphate
show the reaction diagram
-
i.e. clofarabine, rate-limiting step in the activation of the prodrug, precursor of an effective chemotherapeutic agent for leukemias and other haematological malignancies
-
-
?
NTP + 9-beta-D-arabinosyl 2-fluoroadenine
NDP + 9-beta-D-arabinosyl 2-fluoroadenine 5'-phosphate
show the reaction diagram
NTP + 9-beta-D-arabinosyl-2-fluoroadenine
NDP + 9-beta-D-arabinosyl-2-fluoroadenine 5'-phosphate
show the reaction diagram
-
phosphorylation of chemotherapeutically important nucleoside analogues
-
-
?
NTP + deoxycytidine
NDP + dCMP
show the reaction diagram
-
-
-
-
?
NTP + troxacitabine
?
show the reaction diagram
-
activation of the clinically relevant substrate
-
-
?
UTP + 2',3'-dideoxycytidine
UDP + 2',3'-dideoxycytidine 5'-phosphate
show the reaction diagram
-
i.e. zalcitabine, activation of the pharmaceutically relevant substrate which is used for the treatment of HIV infections
-
-
?
UTP + 2'-deoxy-3'-thiacytidine
UDP + 2'-deoxy-3'-thiacytidine 5'-phosphate
show the reaction diagram
-
i.e. lamivudine, activation of the pharmaceutically relevant substrate which is used for the treatment of HIV infections
-
-
?
UTP + 2'-deoxyadenosine
UDP + 2'-deoxyadenosine 5'-phosphate
show the reaction diagram
UTP + 2'-deoxycytidine
UDP + 2'-deoxycytidine 5'-phosphate
show the reaction diagram
UTP + 2'-deoxyguanosine
UDP + 2'-deoxyguanosine 5'-phosphate
show the reaction diagram
UTP + cladribine
UDP + cladribine 5'-phosphate
show the reaction diagram
-
-
-
-
?
UTP + clofarabine
UDP + clofarabine 5'-phosphate
show the reaction diagram
-
-
-
-
?
UTP + deoxyadenosine
UDP + dAMP
show the reaction diagram
-
-
-
-
?
UTP + deoxycytidine
UDP + dCMP
show the reaction diagram
UTP + deoxyguanosine
UDP + dGMP
show the reaction diagram
-
-
-
-
?
UTP + fludarabine
UDP + phospho-fludarabine
show the reaction diagram
-
-
-
-
?
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
-
enzyme lalso utilizes other nucleoside triphosphates as phosphate donors
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
CdCl2
-
activation, in the absence of dithiothreitol
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2'-deoxy-5-fluorocytidine
-
-
2'-deoxycytidine
-
-
2'-O-methylcytidine
-
-
2-(2-[1-[6-(1-benzothiophen-2-yl)pyrimidin-4-yl]piperidin-4-yl]ethoxy)-5-fluoropyrimidin-4-amine
-
-
2-([1-[6-(1-benzothiophen-2-yl)pyrimidin-4-yl]piperidin-4-yl]methoxy)-5-fluoropyrimidin-4-amine
-
-
2-([1-[6-(1-benzothiophen-2-yl)pyrimidin-4-yl]piperidin-4-yl]oxy)-5-fluoropyrimidin-4-amine
-
-
2-([1-[6-(2-chlorophenoxy)pyrimidin-4-yl]piperidin-4-yl]oxy)-5-fluoropyrimidin-4-amine
-
-
2-([1-[6-(2-ethylphenoxy)pyrimidin-4-yl]piperidin-4-yl]oxy)-5-fluoropyrimidin-4-amine
-
-
2-([1-[6-(3-chlorophenoxy)pyrimidin-4-yl]piperidin-4-yl]oxy)-5-fluoropyrimidin-4-amine
-
-
2-([1-[6-(4-chloro-2-methylphenoxy)pyrimidin-4-yl]piperidin-4-yl]oxy)-5-fluoropyrimidin-4-amine
-
-
2-([1-[6-(4-chlorophenoxy)pyrimidin-4-yl]piperidin-4-yl]oxy)-5-fluoropyrimidin-4-amine
-
-
2-([1-[6-(biphenyl-2-yloxy)pyrimidin-4-yl]piperidin-4-yl]oxy)-5-fluoropyrimidin-4-amine
-
-
2-([6-[4-(4-amino-2-oxopyrimidin-1(2H)-yl)piperidin-1-yl]-5-fluoropyrimidin-4-yl]oxy)benzonitrile
-
-
2-chloroadenosine
-
-
2-[(6-[4-[(4-amino-5-fluoropyrimidin-2-yl)oxy]piperidin-1-yl]-2-bromopyrimidin-4-yl)oxy]benzonitrile
-
-
2-[(6-[4-[(4-amino-5-fluoropyrimidin-2-yl)oxy]piperidin-1-yl]-2-methylpyrimidin-4-yl)oxy]benzonitrile
-
-
2-[(6-[4-[(4-amino-5-fluoropyrimidin-2-yl)oxy]piperidin-1-yl]-5-fluoropyrimidin-4-yl)oxy]-5-methoxybenzonitrile
-
-
2-[(6-[4-[(4-amino-5-fluoropyrimidin-2-yl)oxy]piperidin-1-yl]-5-fluoropyrimidin-4-yl)oxy]benzonitrile
-
-
2-[(6-[4-[(4-amino-5-fluoropyrimidin-2-yl)oxy]piperidin-1-yl]-5-methylpyrimidin-4-yl)oxy]benzonitrile
-
-
2-[(6-[4-[(4-amino-5-fluoropyrimidin-2-yl)oxy]piperidin-1-yl]pyrimidin-4-yl)oxy]-5-methoxybenzonitrile
-
-
2-[(6-[4-[(4-amino-5-fluoropyrimidin-2-yl)oxy]piperidin-1-yl]pyrimidin-4-yl)oxy]benzonitrile
-
-
2-[(6-[4-[(4-aminopyrimidin-2-yl)oxy]piperidin-1-yl]-5-fluoropyrimidin-4-yl)oxy]benzonitrile
-
-
2-[[6-(1-benzothiophen-2-yl)pyrimidin-4-yl]oxy]-5-fluoropyrimidin-4-amine
-
-
3'-O-methyl-2'deoxycytidine
-
-
3'-[[(1S,3S)-3-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)cyclopentyl]sulfamoyl]biphenyl-4-carboxamide
-
-
3-[(6-[4-[(4-amino-5-fluoropyrimidin-2-yl)oxy]piperidin-1-yl]-2-fluoropyrimidin-4-yl)oxy]-4-methoxybenzonitrile
-
-
3-[(6-[4-[(4-amino-5-fluoropyrimidin-2-yl)oxy]piperidin-1-yl]-5-fluoropyrimidin-4-yl)oxy]-4-methoxybenzonitrile
-
-
3-[(6-[4-[(4-amino-5-fluoropyrimidin-2-yl)oxy]piperidin-1-yl]-5-fluoropyrimidin-4-yl)oxy]benzonitrile
-
-
3-[(6-[4-[(4-amino-5-fluoropyrimidin-2-yl)oxy]piperidin-1-yl]pyrimidin-4-yl)oxy]benzonitrile
-
-
4'-thio-beta-D-arabinofuranosylcytosine
-
IC50 0.000024 mM
4-(1-benzothiophen-2-yl)-6-[4-(2-oxo-2-pyrrolidin-1-ylethyl)piperazin-1-yl]pyrimidine
5'-O-ethyl-2'-deoxycytidine
-
-
5'-O-methyl-2'-deoxycytidine
-
-
5-chloro-4'-thio-beta-D-arabinofuranosylcytosine
-
IC50 0.051 mM
5-Fluoro-2'-deoxycytidine
5-fluoro-2-([1-[5-fluoro-6-(4-methoxyphenoxy)pyrimidin-4-yl]piperidin-4-yl]oxy)pyrimidin-4-amine
-
-
5-fluoro-2-([1-[6-(2-fluorophenoxy)pyrimidin-4-yl]piperidin-4-yl]oxy)pyrimidin-4-amine
-
-
5-fluoro-2-([1-[6-(2-methoxyphenoxy)pyrimidin-4-yl]piperidin-4-yl]oxy)pyrimidin-4-amine
-
-
5-fluoro-2-([1-[6-(2-methylphenoxy)pyrimidin-4-yl]piperidin-4-yl]oxy)pyrimidin-4-amine
-
-
5-fluoro-2-([1-[6-(3-methoxyphenoxy)pyrimidin-4-yl]piperidin-4-yl]oxy)pyrimidin-4-amine
-
-
5-fluoro-2-([1-[6-(4-methoxyphenoxy)pyrimidin-4-yl]piperidin-4-yl]oxy)pyrimidin-4-amine
-
-
5-fluoro-2-([1-[6-(4-methylphenoxy)pyrimidin-4-yl]piperidin-4-yl]oxy)pyrimidin-4-amine
-
-
5-fluoro-2-[[1-(6-phenoxypyrimidin-4-yl)piperidin-4-yl]oxy]pyrimidin-4-amine
-
-
5-fluoro-4'-thio-beta-D-arabinofuranosylcytosine
-
IC50 0.0000020 mM
adenosine arabinoside
-
weak, not with deoxyadenosine as substrate
alpha-D-2'-Deoxythioguanosine
-
-
Ba2+
-
-
CDP
-
strong
Cu2+
-
-
cytidine
cytosine arabinoside
Cytosine arabinoside monophosphate
-
strong
Cytosine arabinoside triphosphate
dADP
-
strong
deoxyadenosine
deoxycytidine
deoxyguanosine
deoxythymidine
Dideoxyadenosine
-
-
Dideoxycytidine
-
-
Dinitrophenol
-
weak
dioxane
-
-
dUTP
-
-
GSSG
-
thiol reagents protect or reverse
H-7
-
reduces the enzyme activation caused by the addition of 2-chloro-2-deoxyadenosine
IAA
-
weak
lambda protein phosphatase
-
-
-
LP-375752
-
i.e. 2-[4-(6-benzo[b]thiophen-2-yl-pyrimidin-4-yl)-piperazin-1-yl]-1-pyrrolidin-1-yl-ethanone
LP-503392
-
i.e. 2-thio-2'-deoxycytidine
N-ethylmaleimide
N-[(1S,3S)-3-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)cyclopentyl]-2',4'-dichlorobiphenyl-3-sulfonamide
-
-
N-[(1S,3S)-3-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)cyclopentyl]-2'-chlorobiphenyl-3-sulfonamide
-
-
N-[(1S,3S)-3-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)cyclopentyl]-3'-chlorobiphenyl-3-carboxamide
-
-
N-[(1S,3S)-3-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)cyclopentyl]-3'-chlorobiphenyl-3-sulfonamide
-
-
N-[(1S,3S)-3-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)cyclopentyl]-3-bromobenzenesulfonamide
-
-
N-[(1S,3S)-3-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)cyclopentyl]-4''-chloro-2''-methyl-1,1':4',1''-terphenyl-3-carboxamide
-
-
N-[(1S,3S)-3-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)cyclopentyl]-4''-chloro-2''-methyl-1,1':4',1''-terphenyl-3-sulfonamide
-
-
N-[(1S,3S)-3-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)cyclopentyl]-4'-(methylsulfonyl)biphenyl-3-sulfonamide
-
-
N-[(1S,3S)-3-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)cyclopentyl]-4'-chlorobiphenyl-3-sulfonamide
-
-
N-[(1S,3S)-3-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)cyclopentyl]-4'-cyanobiphenyl-3-sulfonamide
-
-
N-[(1S,3S)-3-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)cyclopentyl]-4'-formylbiphenyl-3-sulfonamide
-
-
N-[(1S,3S)-3-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)cyclopentyl]-4'-methoxybiphenyl-3-carboxamide
-
-
N-[(1S,3S)-3-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)cyclopentyl]-4'-methoxybiphenyl-3-sulfonamide
-
-
N-[(1S,3S)-3-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)cyclopentyl]-4'-methylbiphenyl-3-sulfonamide
-
-
N-[(1S,3S)-3-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)cyclopentyl]-4-(1-benzothiophen-2-yl)pyridine-2-carboxamide
-
potent, selective, and orally bioavailable inhibitor of dCK
N-[(1S,3S)-3-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)cyclopentyl]-4-bromobenzenesulfonamide
-
-
N-[(1S,3S)-3-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)cyclopentyl]-4-nitrobenzenesulfonamide
-
-
N-[(1S,3S)-3-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)cyclopentyl]benzenesulfonamide
-
-
N-[(1S,3S)-3-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)cyclopentyl]biphenyl-3-carboxamide
-
-
N-[(1S,3S)-3-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)cyclopentyl]biphenyl-3-sulfonamide
-
-
N6-Phenyladenosine
-
-
NaCl
-
at 0.2-0.4 M, stimulation of 2-deoxycytidine and 2-chlorodeoxyadenosine phosphorylation, but inhibition of 2-deoxyguanosine phosphorylation
Non-substrate inhibitors
-
-
-
Nucleoside analogs
-
related to deoxycytidine, deoxyadenosine or deoxyguanosine
Nucleosides
p-chloromercuribenzoate
-
thiol reagents protect or reverse
P1,P4-diadenosine 5'-tetraphosphate
-
not di-, tri- or pentaphosphate derivative
protein phosphatase lambda
-
-
-
Sodium diphosphate
-
not monophosphate
sorbitol
-
-
staurosporine
-
reduces the enzyme activation caused by the addition of 2-chloro-2-deoxyadenosine
Substrate derivatives
-
overview
-
suramin
-
no effect in unirradiated cells, complete abolishment of UV-C light induced activation
tetrahydrouridine
-
-
Tris-maleate buffer
-
-
Trypsin
-
substrates or dNTP protect corresponding active site
-
Urea
-
-
Uridine arabinoside
-
weak, cytosolic isozyme I
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1-beta-D-arabinosylcytosine
-
i.e. cytarabine, 0.001 mM, stimulation
2'-deoxyadenosine/deoxycoformycin
-
no stimulation of enzyme activity by either compound if applied alone, with both compound at 0.01 mM 2.4fold activation occurs
-
2'-deoxythymidine-5'-thiosulphate
-
in intact cells, activation, reversed by 2-deoxycytidine
2-chloro-2'-arabino-fluoro-2'-deoxyadenosine
-
0.001 mM, stimulation
2-chloro-2'-deoxy-2'-fluoro-arabinosyladenine
-
stimulation
2-chloro-2'-deoxyadenosine
2-fluoro-1-beta-D-arabinosyladenine
-
i.e. fludarabine, 0.001 mM, stimulation
ABCG2
-
the ABC transporter activates the enzyme and reduces intracellular accumulation of clofarabine
-
AG-490
-
-
aphidicolin
arabinosylcytidine
-
stimulation
ATP
-
substrate activation, at high concentrations of deoxycytidine
bovine serum albumin
-
activation
-
calyculin A
-
inhibitor of protein phosphatases, activation
CHAPS
-
slight stimulation, deoxycytidine as substrate
daidzein
-
-
deoxyadenosine
-
activation, deoxycytidine as substrate, mitochondrial isozyme
deoxyguanosine
-
activation, deoxycytidine as substrate, mitochondrial isozyme
dithiothreitol
etoposide
gamma-radiation
-
0.5-2 GY dosage, activation
-
genistein
NaCl
-
at 0.2-0.4 M, stimulation of 2-deoxycytidine and 2-chlorodeoxyadenosine phosphorylation, but inhibition of 2-deoxyguanosine phosphorylation
NaF
-
15 mM, 1 h, activity about twice as high as initial level
okadaic acid
-
-
paclitaxel
-
paclitaxel increases dCK (10% to 50%) activity
PD 153035
-
i.e. 4-(3-bromoanilino)-6,7-dimethoxy-quinazinoline
PD 98059
-
i.e. 2'-amino-3'-methoxyflavone, in absence of deoxycytidine
PD-98059
-
-
SB 203580
-
in absence of deoxycytidine
Sodium cholate
-
slight stimulation, deoxycytidine as substrate
TTP
-
stimulation, cytosolic isozyme I
tyrphostin A47
-
-
UDP
-
stimulation, mitochondrial isozyme
Uridine arabinoside
-
activation, deoxycytidine as substrate, mitochondrial isozyme
Zwittergent 3-14
-
slight stimulation, deoxycytidine as substrate
additional information
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.003 - 0.015
(-)-beta-2',3'-dideoxy-3'-thiacytidine
0.00076
1-(2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl)cytosine
-
pH 7.6, 37C, recombinant enzyme
0.00654
1-(2'-deoxy-2'-fluoro-beta-L-arabinofuranosyl)-5-bromocytosine
-
pH 7.6, 37C, recombinant enzyme
0.00061
1-(2'-deoxy-2'-fluoro-beta-L-arabinofuranosyl)-5-chlorocytosine
-
pH 7.6, 37C, recombinant enzyme
0.00102
1-(2'-deoxy-2'-fluoro-beta-L-arabinofuranosyl)-5-methylcytosine
-
pH 7.6, 37C, recombinant enzyme
0.003 - 0.024
1-beta-D-arabinofuranosylcytosine
0.0131 - 0.1365
1-beta-D-arabinosylcytosine
0.0062 - 0.015
2',2'-difluorodeoxycytidine
0.15 - 0.67
2',3'-dideoxycytidine
0.0085 - 1.437
2'-deoxyadenosine
0.00005 - 0.0089
2'-deoxycytidine
0.021 - 2.266
2'-deoxyguanosine
0.0013
2,5-difluoro-4-[1-(2-deoxy-beta-L-ribofuranosyl)]-aniline
-
pH 7.6, 37C, recombinant enzyme
0.00099 - 0.024
2-chloro-2'-deoxyadenosine
0.0051 - 0.078
2-chlorodeoxyadenosine
0.00032
4'-thio-2'-deoxycytidine
-
cosubstrate ATP 37C, pH 8.0
0.02 - 0.088
4'-thio-beta-D-arabinofuranosylcytosine
2 - 5
9-beta-D-arabinofuranosylguanine
0.001 - 0.2
ATP
0.00041 - 0.015
beta-D-arabinofuranosylcytosine
0.00065 - 0.0155
cladribine
0.0087 - 0.0325
clofarabine
0.0013
CTP
-
cosubstrate 2'-deoxycytidine, 37C, pH 7.4
0.45 - 1.4
cytidine
0.002 - 0.04
cytosine arabinoside
0.0243 - 0.144
D-thymidine
0.12 - 0.89
deoxyadenosine
0.00007 - 0.071
deoxycytidine
0.15 - 3
deoxyguanosine
0.001
dTTP
-
cosubstrate 2'-deoxycytidine, 37C, pH 7.4
0.028 - 0.551
fludarabine
0.0161 - 0.0562
gemcitabine
0.0009
GTP
-
cosubstrate 2'-deoxycytidine, 37C, pH 7.4
0.0178 - 0.138
L-thymidine
0.00388 - 3.485
thymidine
0.011 - 0.058
troxacitabine
0.0005 - 0.0578
UTP
additional information
additional information