Record Information |
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Version | 1.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2021-08-19 23:57:59 UTC |
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NP-MRD ID | NP0000267 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Cytidine monophosphate |
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Description | Cytidine monophosphate, also known as 5'-cytidylic acid and abbreviated CMP, is a nucleotide. It is an ester of phosphoric acid with the nucleoside cytidine. CMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase cytosine. Cytidine monophosphate (CMP) is derived from cytidine triphosphate (CTP) with subsequent loss of two phosphates. The synthesis of the pyrimidines CTP and UTP occurs in the cytoplasm and starts with the formation of carbamoyl phosphate from glutamine and CO2. Next, aspartate undergoes a condensation reaction with carbamoyl-phosphate to form orotic acid. In a subsequent cyclization reaction, the enzyme Aspartate carbamoyltransferase forms N-carbamoyl-aspartate which is converted into dihydroorotic acid by Dihydroorotase. The latter is converted to orotate by Dihydroorotate oxidase. Orotate is covalently linked with a phosphorylated ribosyl unit with Orotate phosphoribosyltransferase (aka "PRPP transferase") catalyzing reaction, yielding orotidine monophosphate (OMP). Orotidine-5-phosphate is decarboxylated by Orotidine-5'-phosphate decarboxylase to form uridine monophosphate (UMP). UMP is phosphorylated by two kinases to uridine triphosphate (UTP) via two sequential reactions with ATP. CTP is subsequently formed by amination of UTP by the catalytic activity of CTP synthetase. Cytosine monophosphate (CMP) and uridine monophosphate (UMP) have been prescribed for the treatment of neuromuscular affections in humans. Patients treated with CMP/UMP recover from altered neurological functions. Additionally, the administration of CMP/UMP appears to favour the entry of glucose in the muscle and CMP/UMP may be important in maintaining the level of hepatic glycogen constant during exercise. [PMID:18663991 ]. |
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Structure | NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O 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 |
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Synonyms | Value | Source |
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CMP | ChEBI | Cytidine-5'-monophosphate | ChEBI | Cytidylate | ChEBI | Cytidylic acid | ChEBI | pC | ChEBI | Cytidine-5'-monophosphoric acid | Generator | Cytidine monophosphoric acid | Generator | Cytidine 5'-monophosphate | HMDB | Cytidine 5'-monophosphoric acid | HMDB | 5'-CMP | HMDB | 5-Cytidylate | HMDB | 5-Cytidylic acid | HMDB | Cytidine 5'-monophosphorate | HMDB | Cytidine 5'-phosphate | HMDB | Cytidine 5'-phosphorate | HMDB | Cytidine 5'-phosphoric acid | HMDB | Cytidine mono(dihydrogen phosphate) | HMDB | Acid, cytidylic | HMDB | monoPhosphate, cytidine | HMDB | 5’-CMP | HMDB | Cytidine 5’-monophosphate | HMDB | Cytidine 5’-monophosphoric acid | HMDB | Cytidine 5’-phosphate | HMDB | Cytidine 5’-phosphoric acid | HMDB | Cytosine 5'-monophosphate | HMDB | Cytosine 5’-monophosphate | HMDB | Cytidine monophosphate | HMDB |
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Chemical Formula | C9H14N3O8P |
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Average Mass | 323.1965 Da |
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Monoisotopic Mass | 323.05185 Da |
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IUPAC Name | {[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid |
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Traditional Name | cytidine monophosphate |
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CAS Registry Number | 63-37-6 |
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SMILES | NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O |
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InChI Identifier | 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 |
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InChI Key | IERHLVCPSMICTF-XVFCMESISA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Pyrimidine nucleotides |
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Sub Class | Pyrimidine ribonucleotides |
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Direct Parent | Pyrimidine ribonucleoside monophosphates |
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Alternative Parents | |
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Substituents | - Pyrimidine ribonucleoside monophosphate
- Pentose phosphate
- Pentose-5-phosphate
- Glycosyl compound
- N-glycosyl compound
- Monosaccharide phosphate
- Pentose monosaccharide
- Aminopyrimidine
- Pyrimidone
- Monoalkyl phosphate
- Hydropyrimidine
- Monosaccharide
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Pyrimidine
- Alkyl phosphate
- Imidolactam
- Tetrahydrofuran
- Heteroaromatic compound
- Secondary alcohol
- 1,2-diol
- Oxacycle
- Organoheterocyclic compound
- Azacycle
- Organopnictogen compound
- Amine
- Alcohol
- Organic oxide
- Organonitrogen compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic nitrogen compound
- Primary amine
- Organic oxygen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Experimental Properties | |
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Predicted Properties | |
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General References | - Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- Hirono A, Fujii H, Miyajima H, Kawakatsu T, Hiyoshi Y, Miwa S: Three families with hereditary hemolytic anemia and pyrimidine 5'-nucleotidase deficiency: electrophoretic and kinetic studies. Clin Chim Acta. 1983 May 30;130(2):189-97. [PubMed:6307548 ]
- Okahira S, Nishikawa F, Nishikawa S, Akazawa T, Seya T, Matsumoto M: Interferon-beta induction through toll-like receptor 3 depends on double-stranded RNA structure. DNA Cell Biol. 2005 Oct;24(10):614-23. [PubMed:16225392 ]
- Daunter B, Newlands J: Seminal plasma biochemistry II: seminal plasma and spermatozoal cytidine monophosphate-sialic acid synthetase and sialyltransferase activities. Andrologia. 1981 May-Jun;13(3):215-24. [PubMed:6267956 ]
- Schmukler M, Jewett PB, Levy CC: The effects of polyamines on a residue-specific human plasma ribonuclease. J Biol Chem. 1975 Mar 25;250(6):2206-12. [PubMed:234961 ]
- Paglia DE, Valentine WN, Keitt AS, Brockway RA, Nakatani M: Pyrimidine nucleotidase deficiency with active dephosphorylation of dTMP: evidence for existence of thymidine nucleotidase in human erythrocytes. Blood. 1983 Nov;62(5):1147-9. [PubMed:6313098 ]
- Yates AJ, Warner JK: Behavior of sugar derivatives in procedures for ganglioside isolation. Lipids. 1984 Jul;19(7):562-9. [PubMed:6748871 ]
- Li YP, Curley G, Lopez M, Chavez M, Glew R, Aragon A, Kumar H, Baca OG: Protein-tyrosine phosphatase activity of Coxiella burnetii that inhibits human neutrophils. Acta Virol. 1996 Nov-Dec;40(5-6):263-72. [PubMed:9171454 ]
- Hirono A, Fujii H, Natori H, Kurokawa I, Miwa S: Chromatographic analysis of human erythrocyte pyrimidine 5'-nucleotidase from five patients with pyrimidine 5'-nucleotidase deficiency. Br J Haematol. 1987 Jan;65(1):35-41. [PubMed:3028466 ]
- Gella A, Ponce J, Cusso R, Durany N: Effect of the nucleotides CMP and UMP on exhaustion in exercise rats. J Physiol Biochem. 2008 Mar;64(1):9-17. [PubMed:18663991 ]
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