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Xanthosine-5'-monophosphate

CAT: 0013-GTR19241190-01Size: 10 mgDry Ice: NoHazardous: No
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Description
Xanthosine 5'-monophosphate (XMP) is a key nucleotide intermediate biosynthesized from inosine monophosphate (IMP) via IMP dehydrogenase. It is widely used in research on purine metabolism, enzyme kinetics, and the study of antiviral and anticancer agents targeting this pathway in biochemical assays.
CAS Number
523-98-8
Field of Research
Metabolism Research
Smiles
O=C1C2=C (N (C=N2) [C@@H]3O[C@H] (COP (=O) (O) O) [C@@H] (O) [C@H]3O) NC (=O) N1
Molecular Formula
C10H13N4O9P
Molecular Weight
364.21
Storage Conditions
-20°C
Notes
For research use only.

Chemical Information

5'-Xanthylic acid

5'-xanthylic acid is a purine ribonucleoside 5'-monophosphate having xanthine as the nucleobase. It has a role as a metabolite, a mouse metabolite and an Escherichia coli metabolite. It is a purine ribonucleoside 5'-monophosphate and a xanthosine 5'-phosphate. It is a conjugate acid of a 5'-xanthylate(2-).

CAS Number523-98-8
PubChem CID73323
IUPAC Name[(2R,3S,4R,5R)-5-(2,6-dioxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
Molecular FormulaC10H13N4O9P
Molecular Weight364.21
XLogP-4
Topological Polar Surface Area192
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count10
Rotatable Bond Count4
Heavy Atom Count24
Formal Charge0
Complexity585
SMILES
C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)NC(=O)NC2=O
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/s1
InChIKey
DCTLYFZHFGENCW-UUOKFMHZSA-N
Chemical Structure
2D Structure
2D structure of 5'-Xanthylic acid
CAS: 523-98-8
CID: 73323
Formula: C10H13N4O9P
MW: 364.21
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight364.21
XLogP3-4
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count10
Rotatable Bond Count4
Exact Mass364.04201500
Monoisotopic Mass364.04201500
Topological Polar Surface Area192 Ų
Heavy Atom Count24
Formal Charge0
Complexity585
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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