Deoxyuridine monophosphate

"dUMP" and "DUMP" redirect here. For other uses, see Dump (disambiguation).

Deoxyuridine monophosphate (dUMP), also known as deoxyuridylic acid or deoxyuridylate in its conjugate acid and conjugate base forms, respectively, is a deoxynucleotide.

Deoxyuridine monophosphate

Names
IUPAC name 2′-Deoxyuridylic acid
Systematic IUPAC name [(2R,3S,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
Other names dUMP
Identifiers
CAS Number	964-26-1 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL211312 N
ChemSpider	58574 N
ECHA InfoCard	100.012.290
MeSH	uridine-4'-monophosphate
PubChem CID	688
UNII	N9J10KFG94 Y
CompTox Dashboard (EPA)	DTXSID20242223
InChI InChI=1S/C9H13N2O8P/c12-5-3-8(11-2-1-7(13)10-9(11)14)19-6(5)4-18-20(15,16)17/h1-2,5-6,8,12H,3-4H2,(H,10,13,14)(H2,15,16,17)/t5-,6+,8+/m0/s1 N Key: JSRLJPSBLDHEIO-SHYZEUOFSA-N N InChI=1/C9H13N2O8P/c12-5-3-8(11-2-1-7(13)10-9(11)14)19-6(5)4-18-20(15,16)17/h1-2,5-6,8,12H,3-4H2,(H,10,13,14)(H2,15,16,17)/t5-,6+,8+/m0/s1 Key: JSRLJPSBLDHEIO-SHYZEUOFBW
SMILES O=P(O)(O)OC[C@H]2O[C@@H](N\1C(=O)NC(=O)/C=C/1)C[C@@H]2O
Properties
Chemical formula	C9H13N2O8P
Molar mass	308.182
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

It is an intermediate in the metabolism of deoxyribonucleotides.

Biosynthesis

Deoxyuridine monophosphate (dUMP) is the deoxygenated form of uridine monophosphate (UMP), and is the precursor to deoxythymidine monophosphate (dTMP), a component of DNA nucleotide biosynthesis.^[1] By replacing the hydroxyl group at the 2' carbon of ribose with a hydrogen, UMP becomes deoxygenated to dUMP.

The synthesis of deoxyuridine monophosphate (dUMP) is a multi-step process that begins with uridine monophosphate (UMP), the product of pyrimidine biosynthesis.^[2] The enzyme nucleoside monophosphate kinase converts UMP and ATP to uridine diphosphate (UDP) and ADP.

In the presence of excess ATP, the enzyme ribonucleotide reductase initiates a chain reaction with UDP, which catalyzes the formation of deoxyuridine diphosphate (dUDP), which is then converted to deoxyuridine triphosphate (dUTP), then deoxyuridine monophosphate (dUMP) via the addition or removal of phosphate groups.^[3]

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles.^{[§ 1]}

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|alt=Fluorouracil (5-FU) Activity edit]]

Fluorouracil (5-FU) Activity edit

1. The interactive pathway map can be edited at WikiPathways: "FluoropyrimidineActivity_WP1601".

See also

• DCMP deaminase
• Uridine monophosphate

Notes

1. Berg, J. M.; Tymoczko, J. L.; Stryer, L. (2002). Biochemistry (5th ed.). New York: W H Freeman. ISBN 978-1-4641-2610-9.
2. Shambaugh, G. E. (June 1979). "Pyrimidine biosynthesis". The American Journal of Clinical Nutrition. 32 (6): 1290–1297. doi:10.1093/ajcn/32.6.1290. PMID 35970.
3. Garrett, Reginald H.; Grisham, Charles M. (2013). Biochemistry (6th ed.). Belmont, CA: Brooks/Cole, Cengage Learning. p. 949. ISBN 9781133106296.