Cytidine-5'-Triphosphate

Identification

Generic Name
Cytidine-5'-Triphosphate
DrugBank Accession Number
DB02431
Background

Cytidine 5'-(tetrahydrogen triphosphate). A cytosine nucleotide containing three phosphate groups esterified to the sugar moiety. [PubChem]

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 483.1563
Monoisotopic: 482.984511771
Chemical Formula
C9H16N3O14P3
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
U3-deoxy-manno-octulosonate cytidylyltransferaseNot AvailableEscherichia coli
UUridine-cytidine kinase 2Not AvailableHumans
U2-C-methyl-D-erythritol 4-phosphate cytidylyltransferaseNot AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
UGlycerol-3-phosphate cytidylyltransferaseNot AvailableBacillus subtilis (strain 168)
U2-C-methyl-D-erythritol 4-phosphate cytidylyltransferaseNot AvailableEscherichia coli (strain K12)
UCoenzyme A biosynthesis bifunctional protein CoaBCNot AvailableEscherichia coli (strain K12)
UCCA-adding enzymeNot AvailableGeobacillus stearothermophilus
UGlucose-1-phosphate cytidylyltransferaseNot AvailableSalmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Pyrimidine MetabolismMetabolic
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)Disease
Sialuria or French Type SialuriaDisease
Sialuria or French Type SialuriaDisease
Salla Disease/Infantile Sialic Acid Storage DiseaseDisease
Clarithromycin Action PathwayDrug action
Roxithromycin Action PathwayDrug action
Gentamicin Action PathwayDrug action
Oxytetracycline Action PathwayDrug action
Tetracycline Action PathwayDrug action
Tay-Sachs DiseaseDisease
Arbekacin Action PathwayDrug action
Troleandomycin Action PathwayDrug action
Josamycin Action PathwayDrug action
Phosphatidylcholine Biosynthesis PC(14:0/14:0)Metabolic
Phosphatidylcholine Biosynthesis PC(14:0/15:0)Metabolic
Phosphatidylcholine Biosynthesis PC(14:0/16:1(9Z))Metabolic
Phosphatidylcholine Biosynthesis PC(14:0/18:2(9Z,12Z))Metabolic
Phosphatidylcholine Biosynthesis PC(14:0/20:0)Metabolic
Phosphatidylcholine Biosynthesis PC(14:0/20:1(11Z))Metabolic
Phosphatidylcholine Biosynthesis PC(14:0/20:2(11Z,14Z))Metabolic
Phosphatidylcholine Biosynthesis PC(14:0/20:4(5Z,8Z,11Z,14Z))Metabolic
Phosphatidylcholine Biosynthesis PC(14:0/20:5(5Z,8Z,11Z,14Z,17Z))Metabolic
Phosphatidylcholine Biosynthesis PC(14:0/22:5(4Z,7Z,10Z,13Z,16Z))Metabolic
Phosphatidylcholine Biosynthesis PC(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))Metabolic
Phosphatidylcholine Biosynthesis PC(14:1(9Z)/14:0)Metabolic
Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:0)Metabolic
Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:1(9Z))Metabolic
Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:3(9Z,12Z,15Z))Metabolic
Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:2(13Z,16Z))Metabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Pentose phosphates
Alternative Parents
Glycosylamines / Monosaccharide phosphates / Monoalkyl phosphates / Hydroxypyrimidines / Hydropyrimidines / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / 1,2-diols / Oxacyclic compounds
show 5 more
Substituents
1,2-diol / Alcohol / Alkyl phosphate / Aromatic heteromonocyclic compound / Azacycle / Glycosyl compound / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Hydroxypyrimidine
show 16 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
cytidine 5'-phosphate, pyrimidine ribonucleoside 5'-triphosphate (CHEBI:17677) / Ribonucleotides, Coenzymes (C00063)
Affected organisms
Not Available

Chemical Identifiers

UNII
K0118UX80T
CAS number
65-47-4
InChI Key
PCDQPRRSZKQHHS-XVFCMESISA-N
InChI
InChI=1S/C9H16N3O14P3/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
IUPAC Name
({[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
SMILES
NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O

References

General References
Not Available
Human Metabolome Database
HMDB0000082
KEGG Compound
C00063
PubChem Compound
6176
PubChem Substance
46507556
ChemSpider
5941
ChEBI
17677
ChEMBL
CHEMBL223533
ZINC
ZINC000003861746
PDBe Ligand
CTP
PDB Entries
1coz / 1gq9 / 1h7g / 1i52 / 1kfd / 1miy / 1r89 / 1raa / 1rab / 1rac
show 158 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility11.2 mg/mLALOGPS
logP-0.34ALOGPS
logP-3.9Chemaxon
logS-1.6ALOGPS
pKa (Strongest Acidic)0.89Chemaxon
pKa (Strongest Basic)4.34Chemaxon
Physiological Charge-4Chemaxon
Hydrogen Acceptor Count13Chemaxon
Hydrogen Donor Count7Chemaxon
Polar Surface Area268.2 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity87.16 m3·mol-1Chemaxon
Polarizability35.87 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8988
Blood Brain Barrier+0.9126
Caco-2 permeable-0.7763
P-glycoprotein substrateNon-substrate0.7622
P-glycoprotein inhibitor INon-inhibitor0.9175
P-glycoprotein inhibitor IINon-inhibitor0.9806
Renal organic cation transporterNon-inhibitor0.96
CYP450 2C9 substrateNon-substrate0.7402
CYP450 2D6 substrateNon-substrate0.8462
CYP450 3A4 substrateNon-substrate0.596
CYP450 1A2 substrateNon-inhibitor0.9167
CYP450 2C9 inhibitorNon-inhibitor0.9233
CYP450 2D6 inhibitorNon-inhibitor0.9134
CYP450 2C19 inhibitorNon-inhibitor0.9043
CYP450 3A4 inhibitorNon-inhibitor0.9438
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.974
Ames testNon AMES toxic0.9125
CarcinogenicityNon-carcinogens0.9062
BiodegradationNot ready biodegradable0.7826
Rat acute toxicity2.2404 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9834
hERG inhibition (predictor II)Non-inhibitor0.8137
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-002b-8965400000-028238d320c37d90d959
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-00b9-5685900000-b067d3b0af4c194d5224
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-0a4i-0309200000-33e695326ec0d28103b4
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-057j-1926700000-417741bbe965170223c0
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0000900000-8f684efa3b15a6d623e8
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0200900000-b00bd64601267250af63
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0w29-0729300000-ddc493303af1fa4ee39d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-4204900000-b8db0b410702384aebc8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0901000000-0dcceb952bcead9c9e7b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-056r-9403100000-76781aad836fed600293
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-210.2874806
predicted
DarkChem Lite v0.1.0
[M-H]-215.5509806
predicted
DarkChem Lite v0.1.0
[M-H]-171.67966
predicted
DeepCCS 1.0 (2019)
[M+H]+213.4982806
predicted
DarkChem Lite v0.1.0
[M+H]+215.8098806
predicted
DarkChem Lite v0.1.0
[M+H]+174.47644
predicted
DeepCCS 1.0 (2019)
[M+Na]+212.9355806
predicted
DarkChem Lite v0.1.0
[M+Na]+214.0247806
predicted
DarkChem Lite v0.1.0
[M+Na]+182.65567
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Escherichia coli
Pharmacological action
Unknown
General Function
3-deoxy-manno-octulosonate cytidylyltransferase activity
Specific Function
Activates KDO (a required 8-carbon sugar) for incorporation into bacterial lipopolysaccharide in Gram-negative bacteria.
Gene Name
kpsU
Uniprot ID
P42216
Uniprot Name
3-deoxy-manno-octulosonate cytidylyltransferase
Molecular Weight
27158.885 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Uridine kinase activity
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 don...
Gene Name
UCK2
Uniprot ID
Q9BZX2
Uniprot Name
Uridine-cytidine kinase 2
Molecular Weight
29298.92 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Kind
Protein
Organism
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Pharmacological action
Unknown
General Function
2-c-methyl-d-erythritol 4-phosphate cytidylyltransferase activity
Specific Function
Catalyzes the formation of 4-diphosphocytidyl-2-C-methyl-D-erythritol from CTP and 2-C-methyl-D-erythritol 4-phosphate (MEP).
Gene Name
ispD
Uniprot ID
Q9X1B3
Uniprot Name
2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase
Molecular Weight
25370.055 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Provides activated glycerol phosphate for teichoic acid synthesis, via incorporation into both the linkage unit and the teichoic acid polymer by TagB and TagF.
Gene Name
tagD
Uniprot ID
P27623
Uniprot Name
Glycerol-3-phosphate cytidylyltransferase
Molecular Weight
15271.45 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Magnesium ion binding
Specific Function
Catalyzes the formation of 4-diphosphocytidyl-2-C-methyl-D-erythritol from CTP and 2-C-methyl-D-erythritol 4-phosphate (MEP).
Gene Name
ispD
Uniprot ID
Q46893
Uniprot Name
2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase
Molecular Weight
25736.995 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Phosphopantothenoylcysteine decarboxylase activity
Specific Function
Catalyzes two steps in the biosynthesis of coenzyme A. In the first step cysteine is conjugated to 4'-phosphopantothenate to form 4-phosphopantothenoylcysteine, in the latter compound is decarboxyl...
Gene Name
coaBC
Uniprot ID
P0ABQ0
Uniprot Name
Coenzyme A biosynthesis bifunctional protein CoaBC
Molecular Weight
43437.685 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Kind
Protein
Organism
Geobacillus stearothermophilus
Pharmacological action
Unknown
General Function
Trna cytidylyltransferase activity
Specific Function
Catalyzes the addition and repair of the essential 3'-terminal CCA sequence in tRNAs without using a nucleic acid template. Adds these three nucleotides in the order of C, C, and A to the tRNA nucl...
Gene Name
cca
Uniprot ID
Q7SIB1
Uniprot Name
CCA-adding enzyme
Molecular Weight
45368.875 Da
Kind
Protein
Organism
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Pharmacological action
Unknown
General Function
Nucleotide binding
Specific Function
Involved in the biosynthesis of the tyvelose, a 3,6-dideoxyhexose found in the O-antigen of the surface lipopolysaccharides. It catalyzes the transfer of a CMP moiety from CTP to glucose 1-phosphat...
Gene Name
rfbF
Uniprot ID
P26396
Uniprot Name
Glucose-1-phosphate cytidylyltransferase
Molecular Weight
29035.34 Da

Drug created at June 13, 2005 13:24 / Updated at July 02, 2020 13:16