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
Structure for Cytidine-5'-Monophosphate (DB03403)
- 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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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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- 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
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Cytidine 5'-Monophosphate Disodium Salt 383W8FIS5C Not Available AJCAHIYEOVKFDR-IAIGYFSYSA-M
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- Pentose phosphates / 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
- General References
- Not Available
- External Links
- 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 89 more
Clinical Trials
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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 183.4541939 predictedDarkChem Lite v0.1.0 [M-H]- 184.0609939 predictedDarkChem Lite v0.1.0 [M-H]- 181.9972939 predictedDarkChem Lite v0.1.0 [M-H]- 158.85307 predictedDeepCCS 1.0 (2019) [M+H]+ 182.8225939 predictedDarkChem Lite v0.1.0 [M+H]+ 183.3511939 predictedDarkChem Lite v0.1.0 [M+H]+ 182.3312939 predictedDarkChem Lite v0.1.0 [M+H]+ 161.24864 predictedDeepCCS 1.0 (2019) [M+Na]+ 182.5314939 predictedDarkChem Lite v0.1.0 [M+Na]+ 183.1577939 predictedDarkChem Lite v0.1.0 [M+Na]+ 181.5032939 predictedDarkChem Lite v0.1.0 [M+Na]+ 168.59941 predictedDeepCCS 1.0 (2019)
Targets
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- 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
- 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
- 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
- Molecular Weight
- 16897.37 Da
References
- 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
- Molecular Weight
- 41689.74 Da
References
- 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
- Molecular Weight
- 22222.175 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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]
- 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
- Molecular Weight
- 16519.835 Da
References
- 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
- Molecular Weight
- 24746.03 Da
References
- 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
- 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
- Molecular Weight
- 34544.37 Da
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52