NAV

Cytidine-5'-Monophosphate

Identification

Generic Name
Cytidine-5'-Monophosphate
DrugBank Accession Number
DB03403
Background

A pyrimidine ribonucleoside 5'-monophosphate having cytosine as the nucleobase.

Type
Small Molecule
Groups
Experimental
Structure
 3D
Similar Structures
Weight
Average: 323.1965
Monoisotopic: 323.051850951
Chemical Formula
C9H14N3O8P
Synonyms
  • 5'-CMP
  • CMP
  • Cytidine monophosphate
  • cytidylate
  • Cytidylic acid
  • pC

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
Target Actions Organism
UUridine-cytidine kinase 2 Not Available Humans
U3-deoxy-manno-octulosonate cytidylyltransferase Not Available Escherichia coli
U2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Not Available Shigella flexneri
UBifunctional enzyme IspD/IspF Not Available Campylobacter jejuni subsp. jejuni serotype O:2 (strain NCTC 11168)
UUMP-CMP kinase Not Available Humans
U2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Not Available Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)
UCytidylate kinase Not Available Escherichia coli (strain K12)
UCoenzyme A biosynthesis bifunctional protein CoaBC Not Available Escherichia coli (strain K12)
UAlpha-2,3-/2,8-sialyltransferase Not Available Campylobacter jejuni
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
Not Available
Pharmacogenomic Effects/ADRsBrowse all" title="" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug InteractionsLearn More" title="" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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

Products

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Product Ingredients
Ingredient UNII CAS InChI Key
Cytidine 5'-Monophosphate Disodium Salt 383W8FIS5C Not Available AJCAHIYEOVKFDR-IAIGYFSYSA-M

Categories

Drug Categories
Chemical TaxonomyProvided byClassyfire
Description
This compound belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleotides
Sub Class
Pyrimidine ribonucleotides
Direct Parent
Pyrimidine ribonucleoside monophosphates
Alternative Parents
磷酸戊糖s/Glycosylamines/Monosaccharide phosphates/Monoalkyl phosphates/Aminopyrimidines and derivatives/Pyrimidones/Imidolactams/Hydropyrimidines/Heteroaromatic compounds/Tetrahydrofurans
show 8 more
Substituents
1,2-diol/Alcohol/Alkyl phosphate/Amine/Aminopyrimidine/Aromatic heteromonocyclic compound/Azacycle/Glycosyl compound/Heteroaromatic compound/Hydrocarbon derivative
show 25 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrimidine ribonucleoside 5'-monophosphate, cytidine 5'-phosphate (CHEBI:17361)/Ribonucleotides (C00055)
Affected organisms
Not Available

Chemical Identifiers

UNII
F469818O25
CAS number
63-37-6
InChI Key
IERHLVCPSMICTF-XVFCMESISA-N
InChI
InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(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}phosphonic acid
SMILES
NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O

References

一般References
Not Available
Human Metabolome Database
HMDB0000095
KEGG Compound
C00055
PubChem Compound
6131
PubChem Substance
46505057
ChemSpider
5901
BindingDB
50310540
ChEBI
17361
ChEMBL
CHEMBL307679
ZINC
ZINC000003861744
PDBe Ligand
C5P
PDB Entries
1gqc/1h47/1h48/1h7f/1h7t/1iv4/1jy8/1knj/1lp6/1me0…
show 88 more

Clinical Trials

Clinical TrialsLearn More" title="" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count

Pharmacoeconomics

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

Properties

State
Solid
Experimental Properties
Property Value Source
melting point (°C) 233 dec °C PhysProp
Predicted Properties
Property Value Source
Water Solubility 16.3 mg/mL ALOGPS
logP -2 ALOGPS
logP -2.9 Chemaxon
logS -1.3 ALOGPS
pKa (Strongest Acidic) 1.15 Chemaxon
pKa (Strongest Basic) 4.19 Chemaxon
Physiological Charge -2 Chemaxon
Hydrogen Acceptor Count 9 Chemaxon
Hydrogen Donor Count 5 Chemaxon
Polar Surface Area 175.14 Å2 Chemaxon
Rotatable Bond Count 4 Chemaxon
Refractivity 65.42 m3·mol-1 Chemaxon
Polarizability 26.9 Å3 Chemaxon
Number of Rings 2 Chemaxon
Bioavailability 1 Chemaxon
Rule of Five Yes Chemaxon
Ghose Filter No Chemaxon
Veber's Rule No Chemaxon
MDDR-like Rule No Chemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Spectrum Spectrum Type Splash Key
Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available
MS/MS Spectrum - Quattro_QQQ 10V, Positive LC-MS/MS splash10-03di-0902000000-617172aee10f02d2ad2b
MS/MS Spectrum - Quattro_QQQ 25V, Positive LC-MS/MS splash10-03di-0900000000-ae1e8fc6db6222910637
MS/MS Spectrum - Quattro_QQQ 40V, Positive LC-MS/MS splash10-03di-2900000000-c9ec8c41f82341b9225e
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive LC-MS/MS splash10-0229-0409000000-f28cc32ecb27c7712081
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive LC-MS/MS splash10-03di-0902000000-9a79f63e713af4d035ab
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive LC-MS/MS splash10-03di-1900000000-a5ef2297cb197b2d13e2
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative LC-MS/MS splash10-00ba-9003000000-fed24d718a29a060134b
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative LC-MS/MS splash10-00ba-9003000000-331ea098a652ec08d560
Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negative LC-MS/MS splash10-00ba-9003000000-fed24d718a29a060134b
LC-MS/MS Spectrum - LC-ESI-QTOF , negative LC-MS/MS splash10-00ba-9003000000-331ea098a652ec08d560
LC-MS/MS Spectrum - LC-ESI-QTOF , positive LC-MS/MS splash10-0229-0409000000-f28cc32ecb27c7712081
LC-MS/MS Spectrum - LC-ESI-QTOF , positive LC-MS/MS splash10-03di-0902000000-9a79f63e713af4d035ab
LC-MS/MS Spectrum - LC-ESI-QTOF , positive LC-MS/MS splash10-03di-1900000000-25254e2c3fbbfd5e145b
1H NMR Spectrum 1D NMR 不是Applicable
1H NMR Spectrum 1D NMR 不是Applicable
13C NMR Spectrum 1D NMR 不是Applicable
[1H,13C] 2D NMR Spectrum 2D NMR 不是Applicable

Targets

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Details 1.Uridine-cytidine kinase 2
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
分子量
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]
Details 2.3-deoxy-manno-octulosonate cytidylyltransferase
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
分子量
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]
Details 3.2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase
Kind
Protein
Organism
Shigella flexneri
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Involved in the biosynthesis of isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP), two major building blocks of isoprenoid compounds. Catalyzes the conversion of 4-diphosphocytidy...
Gene Name
ispF
Uniprot ID
P62619
Uniprot Name
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase
分子量
16897.37 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]
Details 4.Bifunctional enzyme IspD/IspF
Kind
Protein
Organism
Campylobacter jejuni subsp. jejuni serotype O:2 (strain NCTC 11168)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Bifunctional enzyme that catalyzes the formation of 4-diphosphocytidyl-2-C-methyl-D-erythritol from CTP and 2-C-methyl-D-erythritol 4-phosphate (MEP) (IspD), and catalyzes the conversion of 4-dipho...
Gene Name
ispDF
Uniprot ID
Q9PM68
Uniprot Name
Bifunctional enzyme IspD/IspF
分子量
41689.74 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]
Details 5.UMP-CMP kinase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Uridylate kinase activity
Specific Function
Catalyzes the phosphorylation of pyrimidine nucleoside monophosphates at the expense of ATP. Plays an important role in de novo pyrimidine nucleotide biosynthesis. Has preference for UMP and CMP as...
Gene Name
CMPK1
Uniprot ID
P30085
Uniprot Name
UMP-CMP kinase
分子量
22222.175 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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Details 6.2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase
Kind
Protein
Organism
Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Involved in the biosynthesis of isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP), two major building blocks of isoprenoid compounds. Catalyzes the conversion of 4-diphosphocytidy...
Gene Name
ispF
Uniprot ID
Q8RQP5
Uniprot Name
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase
分子量
16519.835 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]
Details 7.Cytidylate kinase
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Cytidylate kinase activity
Specific Function
ATP, dATP, and GTP are equally effective as phosphate donors. CMP and dCMP are the best phosphate acceptors.
Gene Name
cmk
Uniprot ID
P0A6I0
Uniprot Name
Cytidylate kinase
分子量
24746.03 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]
Details 8.Coenzyme A biosynthesis bifunctional protein CoaBC
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
分子量
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]
Details 9.Alpha-2,3-/2,8-sialyltransferase
Kind
Protein
Organism
Campylobacter jejuni
Pharmacological action
Unknown
General Function
Transferase activity, transferring glycosyl groups
Specific Function
Not Available
Gene Name
cst-II
Uniprot ID
Q9LAK3
Uniprot Name
Alpha-2,3-/2,8-sialyltransferase
分子量
34544.37 Da

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52