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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:09:43 UTC
HMDB IDHMDB00998
Secondary Accession NumbersNone
Metabolite Identification
Common NamedCTP
DescriptionDeoxycytidine triphosphate (dCTP) is a cytidine nucleotide triphosphate that is used whenever DNA is synthesized, such as in the polymerase chain reaction. e.g.:.
Structure
Thumb
Synonyms
  1. 2'-Deoxycytidine-5'-triphosphate
  2. dCTP
  3. Deoxy-CTP
  4. Deoxycytidine-triphosphate
Chemical FormulaC9H16N3O13P3
Average Molecular Weight467.1569
Monoisotopic Molecular Weight466.989597149
IUPAC Name({[({[(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
Traditional Name({[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid
CAS Registry Number2056-98-6
SMILES
NC1=NC(=O)N(C=C1)[C@H]1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O1
InChI Identifier
InChI=1S/C9H16N3O13P3/c10-7-1-2-12(9(14)11-7)8-3-5(13)6(23-8)4-22-27(18,19)25-28(20,21)24-26(15,16)17/h1-2,5-6,8,13H,3-4H2,(H,18,19)(H,20,21)(H2,10,11,14)(H2,15,16,17)/t5-,6+,8+/m0/s1
InChI KeyRGWHQCVHVJXOKC-SHYZEUOFSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPyrimidine Nucleotides
Sub ClassPyrimidine Deoxyribonucleotides
Other Descriptors
  • 2'-deoxycytidine phosphate(ChEBI)
  • Aromatic Heteropolycyclic Compounds
  • Deoxyribonucleotides(KEGG)
  • Pyrimidine Deoxyribonucleotides
  • pyrimidine 2'-deoxyribonucleoside 5'-triphosphate(ChEBI)
Substituents
  • Aminopyrimidine
  • Hydropyrimidine
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Phosphoric Acid Ester
  • Pyrimidine
  • Pyrimidone
  • Secondary Alcohol
Direct ParentPyrimidine 2'-deoxyribonucleoside Triphosphates
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility11.8ALOGPS
logP-0.52ALOGPS
logP-3.6ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)0.95ChemAxon
pKa (Strongest Basic)-0.05ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area247.97 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity85.65 m3·mol-1ChemAxon
Polarizability35.21 Å3ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Biofluid Locations
  • Blood
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Pyrimidine MetabolismSMP00046map00240
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified29.0 +/- 19.0 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022359
KNApSAcK IDNot Available
Chemspider ID58601
KEGG Compound IDC00458
BioCyc IDDCTP
BiGG ID35027
Wikipedia LinkdCTP
NuGOwiki LinkHMDB00998
Metagene LinkHMDB00998
METLIN ID5929
PubChem Compound65091
PDB IDDCP
ChEBI ID16311
References
Synthesis ReferenceHinz M; Gottschling D; Eritja R; Seliger H Synthesis and properties of 2'-deoxycytidine triphosphate carrying c-myc tag sequence. Nucleosides, nucleotides & nucleic acids (2000), 19(10-12), 1543-52.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yamauchi T, Ueda T: A sensitive new method for clinically monitoring cytarabine concentrations at the DNA level in leukemic cells. Biochem Pharmacol. 2005 Jun 15;69(12):1795-803. Epub 2005 Apr 26. Pubmed: 15935150
  2. Brzezianska E, Zdzieszynska M, Gos R, Lewinski A: [Genetic analysis of rhodopsin and peripherin genes in patients with autosomal dominant retinitis pigmentosa (adRP) in Polish families] Klin Oczna. 2004;106(6):743-8. Pubmed: 15787173
  3. van 't Wout AB: Gene expression profiling of HIV-1 infection using cDNA microarrays. Methods Mol Biol. 2005;304:455-9. Pubmed: 16061997
  4. Moriarty TJ, Marie-Egyptienne DT, Autexier C: Regulation of 5' template usage and incorporation of noncognate nucleotides by human telomerase. RNA. 2005 Sep;11(9):1448-60. Pubmed: 16120835
  5. Choi JY, Guengerich FP: Adduct size limits efficient and error-free bypass across bulky N2-guanine DNA lesions by human DNA polymerase eta. J Mol Biol. 2005 Sep 9;352(1):72-90. Pubmed: 16061253

Enzymes

General function:
Involved in protein binding
Specific function:
Required for optimal DNA polymerase delta activity
Gene Name:
POLD3
Uniprot ID:
Q15054
Molecular weight:
51400.0
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate. Inhibitor of p53-induced apoptosis.
Gene Name:
NME6
Uniprot ID:
O75414
Molecular weight:
22002.965
Reactions
Adenosine triphosphate + dCDP → ADP + dCTPdetails
General function:
Involved in ATP binding
Specific function:
May contribute to UTP accumulation needed for blast transformation and proliferation.
Gene Name:
UCKL1
Uniprot ID:
Q9NWZ5
Molecular weight:
59465.77
Reactions
dCTP + Uridine → dCDP + Uridine 5'-monophosphatedetails
dCTP + Cytidine → dCDP + Cytidine monophosphatedetails
General function:
Involved in ATP binding
Specific function:
Phosphorylates uridine and cytidine to uridine monophosphate and cytidine monophosphate. Does not phosphorylate deoxyribonucleosides or purine ribonucleosides. Can use ATP or GTP as a phosphate donor. Can also phosphorylate cytidine and uridine nucleoside analogs such as 6-azauridine, 5-fluorouridine, 4-thiouridine, 5-bromouridine, N(4)-acetylcytidine, N(4)-benzoylcytidine, 5-fluorocytidine, 2-thiocytidine, 5-methylcytidine, and N(4)-anisoylcytidine.
Gene Name:
UCK2
Uniprot ID:
Q9BZX2
Molecular weight:
29298.92
Reactions
dCTP + Uridine → dCDP + Uridine 5'-monophosphatedetails
dCTP + Cytidine → dCDP + Cytidine monophosphatedetails
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. Possesses nucleoside-diphosphate kinase, serine/threonine-specific protein kinase, geranyl and farnesyl pyrophosphate kinase, histidine protein kinase and 3'-5' exonuclease activities. Involved in cell proliferation, differentiation and development, signal transduction, G protein-coupled receptor endocytosis, and gene expression. Required for neural development including neural patterning and cell fate determination.
Gene Name:
NME1
Uniprot ID:
P15531
Molecular weight:
17148.635
Reactions
Adenosine triphosphate + dCDP → ADP + dCTPdetails
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. Negatively regulates Rho activity by interacting with AKAP13/LBC. Acts as a transcriptional activator of the MYC gene; binds DNA non-specifically (PubMed:8392752). Exhibits histidine protein kinase activity.
Gene Name:
NME2
Uniprot ID:
P22392
Molecular weight:
30136.92
Reactions
Adenosine triphosphate + dCDP → ADP + dCTPdetails
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP (By similarity).
Gene Name:
NME4
Uniprot ID:
O00746
Molecular weight:
20658.45
Reactions
Adenosine triphosphate + dCDP → ADP + dCTPdetails
General function:
Involved in binding
Specific function:
May activate or repress transcription via interactions with sequence specific DNA-binding proteins. Repression may be mediated at least in part by histone deacetylase activity (HDAC activity)
Gene Name:
MYBBP1A
Uniprot ID:
Q9BQG0
Molecular weight:
148853.2
General function:
Involved in DNA binding
Specific function:
Has a DNA polymerase activity on nicked double-stranded DNA and on a singly primed DNA template. The enzyme activity is resistant to aphidicolin, and inhibited by dideoxynucleotides. Exhibites a single-stranded DNA-dependent ATPase activity. Could be involved in the repair of interstrand cross-links.
Gene Name:
POLQ
Uniprot ID:
O75417
Molecular weight:
289616.715
General function:
Involved in damaged DNA binding
Specific function:
Error-prone DNA polymerase specifically involved in DNA repair. Plays an important role in translesion synthesis, where the normal high-fidelity DNA polymerases cannot proceed and DNA synthesis stalls. Favors Hoogsteen base-pairing in the active site. Inserts the correct base with high-fidelity opposite an adenosine template. Exhibits low fidelity and efficiency opposite a thymidine template, where it will preferentially insert guanosine. May play a role in hypermutation of immunogobulin genes. Forms a Schiff base with 5'-deoxyribose phosphate at abasic sites, but may not have lyase activity.
Gene Name:
POLI
Uniprot ID:
Q9UNA4
Molecular weight:
83005.335
General function:
Involved in DNA binding
Specific function:
Repair polymerase. Involved in base excision repair (BER) responsible for repair of lesions that give rise to abasic (AP) sites in DNA. Has both DNA polymerase and terminal transferase activities. Has a 5'-deoxyribose-5-phosphate lyase (dRP lyase) activity.
Gene Name:
POLL
Uniprot ID:
Q9UGP5
Molecular weight:
63481.66
General function:
Involved in DNA binding
Specific function:
Gap-filling polymerase involved in repair of DNA double-strand breaks by non-homologous end joining (NHEJ). Participates in immunoglobulin (Ig) light chain gene rearrangement in V(D)J recombination.
Gene Name:
POLM
Uniprot ID:
Q9NP87
Molecular weight:
54815.075
General function:
Involved in sequence-specific DNA binding
Specific function:
Forms a complex with DNA polymerase epsilon subunit CHRAC1 and binds naked DNA, which is then incorporated into chromatin, aided by the nucleosome-remodeling activity of ISWI/SNF2H and ACF1.
Gene Name:
POLE3
Uniprot ID:
Q9NRF9
Molecular weight:
16859.4
Reactions
dCTP + DNA → Pyrophosphate + DNAdetails
General function:
Involved in nucleotide binding
Specific function:
Plays an essential role in the initiation of DNA replication. During the S phase of the cell cycle, the DNA polymerase alpha complex (composed of a catalytic subunit POLA1/p180, a regulatory subunit POLA2/p70 and two primase subunits PRIM1/p49 and PRIM2/p58) is recruited to DNA at the replicative forks via direct interactions with MCM10 and WDHD1. The primase subunit of the polymerase alpha complex initiates DNA synthesis by oligomerising short RNA primers on both leading and lagging strands. These primers are initially extended by the polymerase alpha catalytic subunit and subsequently transferred to polymerase delta and polymerase epsilon for processive synthesis on the lagging and leading strand, respectively. The reason this transfer occurs is because the polymerase alpha has limited processivity and lacks intrinsic 3' exonuclease activity for proofreading error, and therefore is not well suited for replicating long complexes.
Gene Name:
POLA1
Uniprot ID:
P09884
Molecular weight:
165911.405
Reactions
dCTP + DNA → Pyrophosphate + DNAdetails
General function:
Involved in DNA binding
Specific function:
Repair polymerase that plays a key role in base-excision repair. Has 5'-deoxyribose-5-phosphate lyase (dRP lyase) activity that removes the 5' sugar phosphate and also acts as a DNA polymerase that adds one nucleotide to the 3' end of the arising single-nucleotide gap. Conducts 'gap-filling' DNA synthesis in a stepwise distributive fashion rather than in a processive fashion as for other DNA polymerases.
Gene Name:
POLB
Uniprot ID:
P06746
Molecular weight:
38177.34
General function:
Involved in nucleotide binding
Specific function:
Possesses two enzymatic activities: DNA synthesis (polymerase) and an exonucleolytic activity that degrades single stranded DNA in the 3'- to 5'-direction. Required with its accessory proteins (proliferating cell nuclear antigen (PCNA) and replication factor C (RFC) or activator 1) for leading strand synthesis. Also involved in completing Okazaki fragments initiated by the DNA polymerase alpha/primase complex.
Gene Name:
POLD1
Uniprot ID:
P28340
Molecular weight:
123629.95
Reactions
dCTP + DNA → Pyrophosphate + DNAdetails
General function:
Involved in nucleotide binding
Specific function:
Participates in DNA repair and in chromosomal DNA replication.
Gene Name:
POLE
Uniprot ID:
Q07864
Molecular weight:
261515.525
Reactions
dCTP + DNA → Pyrophosphate + DNAdetails
General function:
Involved in DNA binding
Specific function:
Participates in DNA repair and in chromosomal DNA replication.
Gene Name:
POLE2
Uniprot ID:
P56282
Molecular weight:
56417.05
Reactions
dCTP + DNA → Pyrophosphate + DNAdetails
General function:
Involved in DNA binding
Specific function:
Involved in the replication of mitochondrial DNA. Associates with mitochondrial DNA.
Gene Name:
POLG
Uniprot ID:
P54098
Molecular weight:
139561.06
General function:
Involved in damaged DNA binding
Specific function:
DNA polymerase specifically involved in DNA repair. Plays an important role in translesion synthesis, where the normal high fidelity DNA polymerases cannot proceed and DNA synthesis stalls. Plays an important role in the repair of UV-induced pyrimidine dimers. Depending on the context, it inserts the correct base, but causes frequent base transitions and transversions. May play a role in hypermutation at immunoglobulin genes. Forms a Schiff base with 5'-deoxyribose phosphate at abasic sites, but does not have lyase activity. Targets POLI to replication foci.
Gene Name:
POLH
Uniprot ID:
Q9Y253
Molecular weight:
78412.77
General function:
Involved in sequence-specific DNA binding
Specific function:
May play a role in allowing polymerase epsilon to carry out its replication and/or repair function.
Gene Name:
POLE4
Uniprot ID:
Q9NR33
Molecular weight:
12208.63
Reactions
dCTP + DNA → Pyrophosphate + DNAdetails
General function:
Involved in nucleotide binding
Specific function:
Interacts with MAD2L2 to form the error prone DNA polymerase zeta involved in translesion DNA synthesis.
Gene Name:
REV3L
Uniprot ID:
O60673
Molecular weight:
352772.565
General function:
Involved in damaged DNA binding
Specific function:
DNA polymerase specifically involved in DNA repair. Plays an important role in translesion synthesis, where the normal high-fidelity DNA polymerases cannot proceed and DNA synthesis stalls. Depending on the context, it inserts the correct base, but causes frequent base transitions, transversions and frameshifts. Lacks 3'-5' proofreading exonuclease activity. Forms a Schiff base with 5'-deoxyribose phosphate at abasic sites, but does not have lyase activity.
Gene Name:
POLK
Uniprot ID:
Q9UBT6
Molecular weight:
98807.815
General function:
Involved in ATP binding
Specific function:
Phosphorylates uridine and cytidine to uridine monophosphate and cytidine monophosphate. Does not phosphorylate deoxyribonucleosides or purine ribonucleosides. Can use ATP or GTP as a phosphate donor. Can also phosphorylate cytidine and uridine nucleoside analogs such as 6-azauridine, 5-fluorouridine, 4-thiouridine, 5-bromouridine, N(4)-acetylcytidine, N(4)-benzoylcytidine, 5-fluorocytidine, 2-thiocytidine, 5-methylcytidine, and N(4)-anisoylcytidine.
Gene Name:
UCK1
Uniprot ID:
Q9HA47
Molecular weight:
22760.43
Reactions
dCTP + Uridine → dCDP + Uridine 5'-monophosphatedetails
dCTP + Cytidine → dCDP + Cytidine monophosphatedetails
General function:
Not Available
Specific function:
Hydrolyzes deoxynucleoside triphosphates (dNTPs) to the corresponding nucleoside monophosphates. Has a strong preference for modified dCTP. Activity is highest with 5-iodo-dCTP, followed by 5-bromo-dCTP, unmodified dCTP, 5-methyl-dCTP and 5-chloro-dCTP. Hydrolyzes 2-chloro-dATP and 2-hydroxy-dATP with lower efficiency, and has even lower activity with unmodified dATP, dTTP and dUTP (in vitro). Does not hydrolyze ATP, UTP, ITP, GTP, dADP, dCDP or dGTP. May protect DNA or RNA against the incorporation of non-canonical nucleotide triphosphates. May protect cells against inappropriate methylation of CpG islands by DNA methyltransferases (By similarity).
Gene Name:
DCTPP1
Uniprot ID:
Q9H773
Molecular weight:
18680.645
Reactions
dCTP + Water → dCMP + Pyrophosphatedetails
General function:
Not Available
Specific function:
The function of the small subunit is not yet clear.
Gene Name:
POLD2
Uniprot ID:
P49005
Molecular weight:
51289.0
Reactions
dCTP + DNA → Pyrophosphate + DNAdetails
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate. Probably has a role in normal hematopoiesis by inhibition of granulocyte differentiation and induction of apoptosis.
Gene Name:
NME3
Uniprot ID:
Q13232
Molecular weight:
19014.85
Reactions
Adenosine triphosphate + dCDP → ADP + dCTPdetails
General function:
Not Available
Specific function:
Does not seem to have NDK kinase activity. Confers protection from cell death by Bax and alters the cellular levels of several antioxidant enzymes including Gpx5. May play a role in spermiogenesis by increasing the ability of late-stage spermatids to eliminate reactive oxygen species (By similarity).
Gene Name:
NME5
Uniprot ID:
P56597
Molecular weight:
Not Available
Reactions
Adenosine triphosphate + dCDP → ADP + dCTPdetails
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate.
Gene Name:
NME7
Uniprot ID:
Q9Y5B8
Molecular weight:
42491.365
Reactions
Adenosine triphosphate + dCDP → ADP + dCTPdetails
General function:
Not Available
Specific function:
DNA primase is the polymerase that synthesizes small RNA primers for the Okazaki fragments made during discontinuous DNA replication.
Gene Name:
PRIM1
Uniprot ID:
P49642
Molecular weight:
Not Available
Reactions
dCTP + DNA → Pyrophosphate + DNAdetails
General function:
Not Available
Specific function:
DNA primase is the polymerase that synthesizes small RNA primers for the Okazaki fragments made during discontinuous DNA replication.
Gene Name:
PRIM2
Uniprot ID:
P49643
Molecular weight:
Not Available
Reactions
dCTP + DNA → Pyrophosphate + DNAdetails