Cytidine-5'-Triphosphate

Identification

Name
Cytidine-5'-Triphosphate
Accession Number
DB02431  (EXPT01053)
Type
Small Molecule
Groups
Experimental
Description

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

Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
K0118UX80T
CAS number
65-47-4
Weight
Average: 483.1563
Monoisotopic: 482.984511771
Chemical Formula
C9H16N3O14P3
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)[[email protected]@H]1O[[email protected]](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[[email protected]@H](O)[[email protected]]1O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U3-deoxy-manno-octulosonate cytidylyltransferaseNot AvailableEscherichia coli
UUridine-cytidine kinase 2Not AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/a-21:0/i-22:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/a-25:0/i-19:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/a-25:0/i-22:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-12:0/18:2(9Z,11Z))Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-12:0/i-13:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-12:0/i-16:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-12:0/i-17:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-13:0/i-14:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-14:0/a-21:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-14:0/i-14:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-14:0/i-16:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-14:0/i-24:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-15:0/a-21:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-15:0/i-19:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-16:0/i-18:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-16:0/i-20:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-16:0/i-21:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-16:0/i-24:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-17:0/a-15:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-17:0/i-13:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-17:0/i-19:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-17:0/i-20:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-17:0/i-21:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-17:0/i-22:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-18:0/18:2(9Z,11Z))Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-18:0/i-17:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-19:0/a-13:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-19:0/a-17:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-19:0/a-25:0)Disease
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-19:0/i-14:0)Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB00082
KEGG Compound
C00063
PubChem Compound
6176
PubChem Substance
46507556
ChemSpider
5941
ChEBI
17677
ChEMBL
CHEMBL223533
HET
CTP
PDB Entries
1coz / 1gq9 / 1h7g / 1i52 / 1kfd / 1miy / 1r89 / 1raa / 1rab / 1rac
show 105 more

Clinical Trials

Clinical Trials
Not Available

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-4.3ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)0.91ChemAxon
pKa (Strongest Basic)-0.54ChemAxon
Physiological Charge-3ChemAxon
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-MSNot Available
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, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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
Pentose phosphate / Pentose-5-phosphate / Glycosyl compound / N-glycosyl compound / Monosaccharide phosphate / Hydroxypyrimidine / Monoalkyl phosphate / Hydropyrimidine / Organic phosphoric acid derivative / Alkyl phosphate
show 16 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
cytidine 5'-phosphate, pyrimidine ribonucleoside 5'-triphosphate (CHEBI:17677) / Ribonucleotides, Coenzymes (C00063)

Targets

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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Human
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. [PubMed:17139284]
  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. [PubMed:17016423]
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. [PubMed:17139284]
  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. [PubMed:17016423]
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. [PubMed:17139284]
  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. [PubMed:17016423]
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. [PubMed:17139284]
  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. [PubMed:17016423]
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. [PubMed:17139284]
  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. [PubMed:17016423]
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 on June 13, 2005 07:24 / Updated on November 09, 2017 03:14