Cytidine-5'-Monophosphate
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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
- 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
- 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 / 1kdo / 1knj / 1lp6 … show 103 more
Clinical Trials
- Clinical Trials
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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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1. DetailsUridine-cytidine kinase 2
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Phosphorylates uridine and cytidine to uridine monophosphate and cytidine monophosphate (PubMed:11306702, PubMed:11494055). Does not phosphorylate deoxyribonucleosides or purine ribonucleosides (PubMed:11306702). Can use ATP or GTP as a phosphate donor (PubMed:11306702). 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 (PubMed:11306702)
- Specific Function
- ATP binding
- 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
- Activates KDO (a required 8-carbon sugar) for incorporation into bacterial lipopolysaccharide in Gram-negative bacteria.
- Specific Function
- 3-deoxy-manno-octulosonate cytidylyltransferase activity
- 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
- Involved in the biosynthesis of isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP), two major building blocks of isoprenoid compounds. Catalyzes the conversion of 4-diphosphocytidyl-2-C-methyl-D-erythritol 2-phosphate (CDP-ME2P) to 2-C-methyl-D-erythritol 2,4-cyclodiphosphate (ME-CPP) with a corresponding release of cytidine 5-monophosphate (CMP).
- Specific Function
- 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase activity
- Gene Name
- ispF
- Uniprot ID
- P62619
- Uniprot Name
- 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase
- Molecular Weight
- 16897.37 Da
References
4. DetailsBifunctional enzyme IspD/IspF
- Kind
- Protein
- Organism
- Campylobacter jejuni subsp. jejuni serotype O:2 (strain NCTC 11168)
- Pharmacological action
- Unknown
- General 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-diphosphocytidyl-2-C-methyl-D-erythritol 2-phosphate (CDP-ME2P) to 2-C-methyl-D-erythritol 2,4-cyclodiphosphate (ME-CPP) with a corresponding release of cytidine 5-monophosphate (CMP) (IspF).
- Specific Function
- 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase activity
- Gene Name
- ispDF
- Uniprot ID
- Q9PM68
- Uniprot Name
- Bifunctional enzyme IspD/IspF
- Molecular Weight
- 41689.74 Da
References
5. DetailsUMP-CMP kinase
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General 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 phosphate acceptors. Also displays broad nucleoside diphosphate kinase activity
- Specific Function
- (d)CMP kinase activity
- 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
- Involved in the biosynthesis of isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP), two major building blocks of isoprenoid compounds. Catalyzes the conversion of 4-diphosphocytidyl-2-C-methyl-D-erythritol 2-phosphate (CDP-ME2P) to 2-C-methyl-D-erythritol 2,4-cyclodiphosphate (ME-CPP) with a corresponding release of cytidine 5-monophosphate (CMP).
- Specific Function
- 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase activity
- Gene Name
- ispF
- Uniprot ID
- Q8RQP5
- Uniprot Name
- 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase
- Molecular Weight
- 16519.835 Da
References
7. DetailsCytidylate kinase
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- ATP, dATP, and GTP are equally effective as phosphate donors. CMP and dCMP are the best phosphate acceptors.
- Specific Function
- ATP binding
- 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
- Catalyzes two sequential steps in the biosynthesis of coenzyme A. In the first step cysteine is conjugated to 4'-phosphopantothenate to form 4-phosphopantothenoylcysteine (PubMed:11278255, PubMed:12140293, PubMed:14686929). In the second step the latter compound is decarboxylated to form 4'-phosphopantotheine (PubMed:10922366, PubMed:11358972).
- Specific Function
- FMN binding
- Gene Name
- coaBC
- Uniprot ID
- P0ABQ0
- Uniprot Name
- Coenzyme A biosynthesis bifunctional protein CoaBC
- Molecular Weight
- 43437.685 Da
References
9. DetailsAlpha-2,3-/2,8-sialyltransferase
- Kind
- Protein
- Organism
- Campylobacter jejuni
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- glycosyltransferase activity
- 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