Xanthosine monophosphate

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Xanthosine monophosphate
Names

IUPAC name 5'-xanthylic acid
Other names xanthine ribotide, XMP
Identifiers
CAS Number	523-98-8
3D model (JSmol)	Interactive image
ChEBI	CHEBI:15652
ChemSpider	66054
KEGG	C00655
MeSH	Xanthosine+monophosphate
PubChem CID	122280
UNII	Y29K672ETF
CompTox Dashboard (EPA)	DTXSID20966674
InChI InChI=1S/C10H13N4O9P/c15-5-3(1-22-24(19,20)21)23-9(6(5)16)14-2-11-4-7(14)12-10(18)13-8(4)17/h2-3,5-6,9,15-16H,1H2,(H2,19,20,21)(H2,12,13,17,18)/t3-,5-,6-,9-/m1/s1Key: DCTLYFZHFGENCW-UUOKFMHZSA-N InChI=1/C10H13N4O9P/c15-5-3(1-22-24(19,20)21)23-9(6(5)16)14-2-11-4-7(14)12-10(18)13-8(4)17/h2-3,5-6,9,15-16H,1H2,(H2,19,20,21)(H2,12,13,17,18)/t3-,5-,6-,9-/m1/s1Key: DCTLYFZHFGENCW-UUOKFMHZBH
SMILES C1=NC2=C(N13(((O3)COP(=O)(O)O)O)O)NC(=O)NC2=O
Properties
Chemical formula	C₁₀H₁₃N₄O₉P
Molar mass	364.206 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Xanthosine monophosphate (xanthylate) is an intermediate in purine metabolism. It is a ribonucleoside monophosphate. It is formed from IMP via the action of IMP dehydrogenase, and it forms GMP via the action of GMP synthase. Also, XMP can be released from XTP by enzyme deoxyribonucleoside triphosphate pyrophosphohydrolase containing (d)XTPase activity.

It is abbreviated XMP.

References

McMurry, John (2007). Organic chemistry: a biological approach. Cengage Learning. pp. 1007–. ISBN 9780495015253. Retrieved 26 March 2012.
Davies O, Mendes P, Smallbone K, Malys N (2012). "Characterisation of multiple substrate-specific (d)ITP/(d)XTPase and modelling of deaminated purine nucleotide metabolism" (PDF). BMB Reports. 45 (4): 259–64. doi:10.5483/BMBRep.2012.45.4.259. PMID 22531138.
Gogia, S.; Balaram, H.; Puranik, M. (May 2011). "Hypoxanthine guanine phosphoribosyltransferase distorts the purine ring of nucleotide substrates and perturbs the pKa of bound xanthosine monophosphate". Biochemistry. 50 (19): 4184–93. doi:10.1021/bi102039b. PMID 21486037.

Sigel, H; Operschall, BP; Griesser, R (2009). "Xanthosine 5'-monophosphate (XMP). Acid-base and metal ion-binding properties of a chameleon-like nucleotide" (PDF). Chemical Society Reviews. 38 (8): 2465–94. doi:10.1039/b902181g. PMID 19623361. S2CID 205726340. Archived from the original (PDF) on 2020-01-01.
Egli, M; Pallan, PS (2010). "Crystallographic studies of chemically modified nucleic acids: A backward glance". Chemistry & Biodiversity. 7 (1): 60–89. doi:10.1002/cbdv.200900177. PMC 2905155. PMID 20087997.

Nucleic acid constituents

Nucleobase

Nucleoside

Ribonucleoside	Adenosine Guanosine 5-Methyluridine Uridine 5-Methylcytidine Cytidine Pseudouridine Inosine N-Methyladenosine Xanthosine Wybutosine
Deoxyribonucleoside	Deoxyadenosine Deoxyguanosine Thymidine Deoxyuridine Deoxycytidine Deoxyinosine Deoxyxanthosine

Nucleotide
(Nucleoside monophosphate)

Ribonucleotide	AMP GMP mUMP UMP CMP IMP XMP
Deoxyribonucleotide	dAMP dGMP dTMP dUMP dCMP dIMP dXMP
Cyclic nucleotide	cAMP cGMP c-di-GMP c-di-AMP cADPR cGAMP

Nucleoside diphosphate

ADP GDP mUDP UDP CDP Xanthosine diphosphate
dADP dGDP dTDP dUDP dCDP

Nucleoside triphosphate

ATP GTP mUTP UTP CTP ITP XTP
dATP dGTP dTTP dUTP dCTP dITP dXTP

Nucleotide metabolic intermediates

purine
metabolism

anabolism

R5P→IMP:	Ribose 5-phosphate (R5P) Phosphoribosyl pyrophosphate (PRPP) Phosphoribosylamine (PRA) Glycineamide ribonucleotide (GAR) Phosphoribosyl-N-formylglycineamide (FGAR) 5′-Phosphoribosylformylglycinamidine (FGAM) 5-Aminoimidazole ribotide (AIR) 5′-Phosphoribosyl-4-carboxy-5-aminoimidazole (CAIR) Phosphoribosylaminoimidazolesuccinocarboxamide (SAICAR) AICA ribonucleotide (AICAR) 5-Formamidoimidazole-4-carboxamide ribotide (FAICAR)
IMP→AMP:	Adenylosuccinate
IMP→GMP:	Xanthosine monophosphate

catabolism

pyrimidine
metabolism

anabolism

catabolism

uracil:	β-Alanine Dihydrouracil 3-Ureidopropionic acid
thymine:	3-Aminoisobutyric acid Dihydrothymine β-Ureidoisobutyric acid

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References

Further reading