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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-10-09 21:09:49 UTC |
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HMDB ID | HMDB0000095 |
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Secondary Accession Numbers | |
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Metabolite 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 | |
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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 | Cytidine monophosphate | HMDB | Cytosine 5'-monophosphate | HMDB | Cytosine 5’-monophosphate | HMDB |
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Chemical Formula | C9H14N3O8P |
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Average Molecular Weight | 323.1965 |
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Monoisotopic Molecular Weight | 323.051850951 |
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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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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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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 233 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0002-9511000000-b038dcf334a34dfe4149 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-01ot-9414000000-5835e3555d5546f12c1f | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-03di-0902000000-617172aee10f02d2ad2b | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-03di-0900000000-ae1e8fc6db6222910637 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-03di-2900000000-c9ec8c41f82341b9225e | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0229-0409000000-f28cc32ecb27c7712081 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive | splash10-03di-0902000000-9a79f63e713af4d035ab | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-03di-1900000000-a5ef2297cb197b2d13e2 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-00ba-9003000000-fed24d718a29a060134b | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-00ba-9003000000-331ea098a652ec08d560 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-00ba-9003000000-fed24d718a29a060134b | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-00ba-9003000000-331ea098a652ec08d560 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0229-0409000000-f28cc32ecb27c7712081 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-03di-0902000000-9a79f63e713af4d035ab | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-03di-1900000000-25254e2c3fbbfd5e145b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0901000000-75b42cbe789350bd13b0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-4900000000-fa026ae4d1a84f43102e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-7900000000-5adaadd61efb1191857e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0200-9848000000-0ac0c37265bd767019b2 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9200000000-5dd0a8c928cf323e5d75 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-73255a3373b4f1f51b4d | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | - Extracellular
- Mitochondria
- Nucleus
- Lysosome
- Golgi apparatus
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Biospecimen Locations | |
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Tissue Locations | - All Tissues
- Placenta
- Prostate
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Pathways | |
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Normal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 1.27 +/- 0.75 uM | Adult (>18 years old) | Female | Normal | | details | Saliva | Detected and Quantified | 0.0573 +/- 0.176 uM | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected and Quantified | 0.0965 +/- 0.0870 uM | Adult (>18 years old) | Female | Normal | | details |
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Abnormal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Saliva | Detected and Quantified | 0.90 +/- 0.71 uM | Adult (>18 years old) | Male | Alzheimer's disease | | details | Saliva | Detected and Quantified | 1.02 +/- 0.31 uM | Adult (>18 years old) | Male | Frontotemporal lobe dementia | | details | Saliva | Detected and Quantified | 0.63 +/- 0.64 uM | Adult (>18 years old) | Both | Lewy body disease | | details |
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Associated Disorders and Diseases |
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Disease References | Colorectal cancer |
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- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
| Alzheimer's disease |
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- Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
| Frontotemporal dementia |
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- Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
| Lewy body disease |
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- Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | DB03403 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB030736 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 5901 |
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KEGG Compound ID | C00055 |
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BioCyc ID | CMP |
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BiGG ID | 33689 |
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Wikipedia Link | Cytidine monophosphate |
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METLIN ID | Not Available |
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PubChem Compound | 6131 |
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PDB ID | Not Available |
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ChEBI ID | 17361 |
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Food Biomarker Ontology | Not Available |
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VMH ID | CMP |
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MarkerDB ID | MDB00029866 |
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References |
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Synthesis Reference | Zhou, Jingkang. Method for preparing cytidine 5'-monophosphate. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 12 pp. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - 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 ]
- 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 ]
- 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 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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