- 関
- UMP、uridine monophosphate
WordNet
- street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
- any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
- having the characteristics of an acid; "an acid reaction"
PrepTutorEJDIC
- 酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/11/18 12:47:31」(JST)
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Uridine monophosphate
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| Names |
| IUPAC name
[(2R,3S,4R,5R)-5-(2,4-Dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
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| Other names
Uridylic acid; Uridine 5'-monophosphate; 5'-Uridylic acid; Uridine 5'-phosphate; Uridine phosphate; 5'-UMP; Uridine 5'-phosphoric acid
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| Identifiers |
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CAS Number
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3D model (JSmol)
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| ChemSpider |
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| ECHA InfoCard |
100.000.371 |
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IUPHAR/BPS
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| MeSH |
Uridine+monophosphate |
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InChI
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InChI=1S/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1 N
Key: DJJCXFVJDGTHFX-XVFCMESISA-N N
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InChI=1/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
Key: DJJCXFVJDGTHFX-XVFCMESIBD
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SMILES
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c1cn(c(=O)[nH]c1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O
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| Properties |
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Chemical formula
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C9H13N2O9P |
| Molar mass |
324.18 g·mol−1 |
| Melting point |
202 °C (396 °F; 475 K) (decomposes)[1] |
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Solubility in water
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good, also in methanol [1] |
| Acidity (pKa) |
1.0, 6.4, 9.5 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| N verify (what is YN ?) |
| Infobox references |
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Uridine monophosphate (UMP), also known as 5′-uridylic acid (conjugate base uridylate), is a nucleotide that is used as a monomer in RNA. It is an ester of phosphoric acid with the nucleoside uridine. UMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase uracil; hence, it is a ribonucleotide monophosphate. As a substituent or radical its name takes the form of the prefix uridylyl-. The deoxy form is abbreviated dUMP.
Contents
- 1 Biosynthesis
- 2 Effects on animal intelligence
- 3 In foods
- 4 See also
- 5 References
Biosynthesis
Uridine monophosphate is formed from Orotidine 5'-monophosphate (orotidylic acid) in a decarboxylation reaction catalyzed by the enzyme orotidylate decarboxylase. Uncatalyzed, the decarboxylation reaction is extremely slow (estimated to occur on average one time per 78 million years). Adequately catalyzed, the reaction takes place once per second, an increase of 1017-fold.[2]
In humans, the orotidylate decarboxylase function is carried out by the protein UMP synthase.[3] Defective UMP synthase can result in orotic aciduria, a metabolic disorder.
Effects on animal intelligence
In a study, gerbils fed a combination of uridine monophosphate, choline, and docosahexaenoic acid (DHA) were found to have significantly improved performance in running mazes over those not fed the supplements, implying an increase in cognitive function.[4][5]
In foods
In brain research studies, uridine monophosphate is used as a convenient delivery compound for uridine.[6] Uridine is the active component of this compound. Uridine is present in many foods, mainly in the form of RNA. Non-phosphorylated uridine is not bioavailable beyond first-pass metabolism, as it is almost entirely catabolised in the liver and gastrointestinal tract.[7]
See also
- Nucleoside
- Nucleotide
- DNA
- RNA
- Oligonucleotide
- Pyrimidine biosynthesis
References
- ^ a b M. Lide, D. R. Lide: CRC Handbook of Chemistry and Physics. 87. Auflage, S. 3-56, CRC Press, 1998, ISBN 978-0-8493-0594-8
- ^ Berg J, Tymoczko JL, Stryer L (2006). Biochemistry (6th ed.). San Francisco: W. H. Freeman. ISBN 0-7167-8724-5.
- ^ Analysis of UMP synthase gene and mRNA structure in hereditary orotic aciduria fibroblasts
- ^ Holguin, S.; Martinez, J.; Chow, C.; Wurtman, R. (2008). "Dietary uridine enhances the improvement in learning and memory produced by administering DHA to gerbils". The FASEB Journal. 22 (11): 3938–3946. doi:10.1096/fj.08-112425. PMC 2574024 . PMID 18606862.
- ^ Get Smart About What You Eat And You Might Actually Improve Your Intelligence. ScienceDaily, July 3, 2008
- ^ Wurtman; et al. (2009). "Use of phosphatide precursors to promote synaptogenesis". Annual Review of Nutrition. 29: 59–87. doi:10.1146/annurev-nutr-080508-141059. PMID 19400698.
- ^ Gasser; et al. (1981). "Novel single-pass exchange of circulating uridine in rat liver". Science. 213 (4509): 777–8. doi:10.1126/science.7256279. PMID 7256279.
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Nucleic acid constituents
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| Nucleobase |
- Purine
- Adenine
- Guanine
- Hypoxanthine
- Xanthine
- Purine analogue
- Pyrimidine
- Uracil
- Thymine
- Cytosine
- Pyrimidine analogue
- Unnatural base pair (UBP)
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| Nucleoside |
| Ribonucleoside |
- Adenosine
- Guanosine
- 5-Methyluridine
- Uridine
- 5-Methylcytidine
- Cytidine
- Inosine
- Xanthosine
- Wybutosine
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| Deoxyribonucleoside |
- Deoxyadenosine
- Deoxyguanosine
- Thymidine
- Deoxyuridine
- Deoxycytidine
- Deoxyinosine
- Deoxyxanthosine
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Nucleotide
(Nucleoside monophosphate) |
| Ribonucleotide |
- AMP
- GMP
- m5UMP
- UMP
- CMP
- IMP
- XMP
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| Deoxyribonucleotide |
- dAMP
- dGMP
- dTMP
- dUMP
- dCMP
- dIMP
- dXMP
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| Cyclic nucleotide |
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| Nucleoside diphosphate |
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| Nucleoside triphosphate |
- ATP
- GTP
- m5UTP
- UTP
- CTP
- ITP
- XTP
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- dATP
- dGTP
- dTTP
- dUTP
- dCTP
- dITP
- dXTP
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Nucleotide metabolic intermediates
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| Purine metabolism |
| Anabolism |
| R5P→IMP: |
- R5P
- PRPP
- PRA
- GAR
- FGAR
- FGAM
- AIR
- CAIR
- SAICAR
- AICAR
- FAICAR
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| IMP→AMP: |
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| IMP→GMP: |
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| Catabolism |
- Hypoxanthine
- Xanthine
- Uric acid
- 5-Hydroxyisourate
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| Pyrimidine metabolism |
| Anabolism |
- Carbamoyl phosphate
- Carbamoyl aspartic acid
- 4,5-Dihydroorotic acid
- Orotic acid
- Orotidine 5'-monophosphate
- Uridine monophosphate
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| Catabolism |
| uracil: |
- Dihydrouracil
- 3-Ureidopropionic acid
- β-Alanine
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| thymine: |
- Dihydrothymine
- β-Ureidoisobutyric acid
- 3-Aminoisobutyric acid
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UpToDate Contents
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English Journal
- Hereditary Orotic Aciduria and the Excretion of Orotidine.
- Nyhan WL1, Gangoiti JA1.
- Neuropediatrics.Neuropediatrics.2016 Dec;47(6):408-409. Epub 2016 Aug 30.
- Objective Orotic aciduria and deficiency of uridine monophosphate synthetase have been observed in a patient, studied over 10 years, who had no megaloblastic anemia. Excretion of orotic acid and orotidine were 8.24 and 0.52 mmol/mol of creatinine. The ratio of 15.85 differed appreciably from that
- PMID 27574833
- Identification of Chemical Compounds That Inhibit Protein Synthesis in Pseudomonas aeruginosa.
- Palmer SO1, Hu Y1, Keniry M2, Bullard JM3.
- Journal of biomolecular screening.J Biomol Screen.2016 Nov 21. pii: 1087057116679591. [Epub ahead of print]
- Four inhibitory compounds were identified using a poly-uridylic acid (polyU) mRNA-directed aminoacylation/translation (A/T) protein synthesis system composed of phenylalanyl-tRNA synthetases (PheRS), ribosomes, and ribosomal factors from Pseudomonas aeruginosa in an in vitro screen of a synthetic co
- PMID 27872201
- Reverse of Acute and Chronic Morphine Tolerance by Lithocholic Acid via Down-Regulating UGT2B7.
- Yang Z1, Li L2, Hu H1, Xu M1, Gu J3, Wang ZJ4, Yu L1, Zeng S1.
- Frontiers in pharmacology.Front Pharmacol.2016 Nov 1;7:404. eCollection 2016.
- Lithocholic acid (LCA) deposited in human livers always induces drastic pains which need analgesic drug, like morphine to release. Our research showed that LCA can effectively inhibit uridine 5'-diphospho-glucuronosyltransferase 2B7 (UGT2B7) in morphine tolerance-like human normal liver cells, HL-77
- PMID 27847477
Japanese Journal
- Effects of 5'-uridylic acid feeding on postprandial plasma concentrations of metabolites and metabolic hormones in pre-weaning goats
- OHTANI Yoshihisa,KOBAYASHI Yosuke,TAKAHASHI Tatsuyuki,HAGA Satoshi,TAKAGI Mutsuo,MASHIKO Takanori,KATOH Kazuo,OBARA Yoshiaki
- Animal science journal 80(5), 570-576, 2009-10-01
- NAID 10027887559
- Base Specificity and Primary Structure of Poly U-preferential Ribonuclease from Chicken Liver
- Uchida Takashi,Hayano Kumi,Iwama Masanori [他],WATANABE Hideaki,SANDA Akihiro,OHGI Kazuko,IRIE Masachika
- Bioscience, biotechnology, and biochemistry 60(12), 1982-1988, 1996-12-23
- … The sequence study of this enzyme and comparison of the amino acid sequence of the enzyme with homologous RNases from oyster and Drosophila melanogaster suggested that RNase CL_1 consists of three peptides with 17, 19, and 163 amino acid residues. … The amino acid sequence of these three peptides were identified. … The amino acid sequence of RNase CL_1 had 62 (31.2%) and 63 residues (31.6%) identical with oyster RNase and D. …
- NAID 110002678418
- 2. 新しいターゲットと方法 時分割ラウエ法による動的結晶構造解析
- 野中 孝昌
- 日本結晶学会誌 38(1), 35-40, 1996-02-28
- … Omit Fourier difference maps clearly showed the sulfate anion molecule or the 3'-uridylic acid molecule bound to the catalytic center of ribonuclease A. …
- NAID 10002024699
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- 関
- dUMP