XANTHOSINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H12N4O6
Molecular Weight	284.2255
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=NC3=C2NC(=O)NC3=O

InChI

InChIKey=UBORTCNDUKBEOP-UUOKFMHZSA-N

InChI=1S/C10H12N4O6/c15-1-3-5(16)6(17)9(20-3)14-2-11-4-7(14)12-10(19)13-8(4)18/h2-3,5-6,9,15-17H,1H2,(H2,12,13,18,19)/t3-,5-,6-,9-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C10H12N4O6
Molecular Weight	284.2255
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Essential region for 3-N methylation in N-methyltransferases involved in caffeine biosynthesis.	2010-05-18	20469646
Expression for caffeine biosynthesis and related enzymes in Camellia sinensis.	2010-05-18	20469645
An ab initio and AIM investigation into the hydration of 2-thioxanthine.	2010-03-23	20331849
Homeostatic imbalance of purine catabolism in first-episode neuroleptic-naïve patients with schizophrenia.	2010-03-03	20209081
Interpreting metabolomic profiles using unbiased pathway models.	2010-02-26	20195502
Evaluation of inosin-5'-monophosphate dehydrogenase activity during maintenance therapy with tacrolimus.	2010-02	20175815
Crystal structure of the ATPPase subunit and its substrate-dependent association with the GATase subunit: a novel regulatory mechanism for a two-subunit-type GMP synthetase from Pyrococcus horikoshii OT3.	2010-01-15	19900465
Opioid use affects antioxidant activity and purine metabolism: preliminary results.	2009-12	19760630
Alterations in tryptophan and purine metabolism in cocaine addiction: a metabolomic study.	2009-10	19649617
A fast capillary electrophoresis method for separation and quantification of modified nucleosides in urinary samples.	2009-08-01	19552424
Xanthosine 5'-monophosphate (XMP). Acid-base and metal ion-binding properties of a chameleon-like nucleotide.	2009-08	19623361
Radiation metabolomics. 2. Dose- and time-dependent urinary excretion of deaminated purines and pyrimidines after sublethal gamma-radiation exposure in mice.	2009-07	19580506
Prediction of breast cancer by profiling of urinary RNA metabolites using Support Vector Machine-based feature selection.	2009-04-05	19344524
In vivo expansion of the mammary stem/ progenitor cell population by xanthosine infusion.	2009-04	19176874
Chemical constituents from the seeds of Trifolium alexandrinum.	2008-12	19085418
A kinetic alignment of orthologous inosine-5'-monophosphate dehydrogenases.	2008-08-19	18642884
Expression of caffeine biosynthesis genes in tea (Camellia sinensis).	2008-06-07	18533472
ITPase activity in dry blood spots is comparable with that in fresh erythrocytes.	2008-06	18600522
Significance analysis of microarray for relative quantitation of LC/MS data in proteomics.	2008-04-10	18402702
Structure and inhibition of orotidine 5'-monophosphate decarboxylase from Plasmodium falciparum.	2008-03-25	18303855
Retraction notice to "Validation and application of a high-performance liquid chromatographic-based assay for determination of the inosine 5'-monophosphate dehydrogenase activity in erythrocytes." [J. Chromatogr. B 842 (2006) 1-7].	2008-03-15	18441551
Dimerization of N-methyltransferases involved in caffeine biosynthesis.	2008-03	17976385
Horizontal gene transfer and the evolution of transcriptional regulation in Escherichia coli.	2008-01-07	18179685
Structure and redox properties of radicals derived from one-electron oxidised methylxanthines.	2008	18544230
CFP and YFP, but not GFP, provide stable fluorescent marking of rat hepatic adult stem cells.	2008	18401450
Molecular basis of the antimutagenic activity of the house-cleaning inosine triphosphate pyrophosphatase RdgB from Escherichia coli.	2007-12-07	17976651
Metabolic signature of breast cancer cell line MCF-7: profiling of modified nucleosides via LC-IT MS coupling.	2007-11-29	18047657
RNA analysis by MEKC with LIF detection.	2007-11	17922502
The structure of two N-methyltransferases from the caffeine biosynthetic pathway.	2007-06	17434991
Structure-based design, synthesis, evaluation, and crystal structures of transition state analogue inhibitors of inosine monophosphate cyclohydrolase.	2007-04-27	17324932
Cloning, expression, crystallization and preliminary X-ray analysis of the XMT and DXMT N-methyltransferases from Coffea canephora (robusta).	2007-04-01	17401201
Antiviral activity of tiazofurin and mycophenolic acid against Grapevine leafroll-associated virus 3 in Vitis vinifera explants.	2007-03	17125850
The phosphofructokinase-B (MJ0406) from Methanocaldococcus jannaschii represents a nucleoside kinase with a broad substrate specificity.	2007-01	17021658
Evidence for intramolecular aromatic-ring stacking in the physiological pH range of the monodeprotonated xanthine residue in mixed-ligand complexes containing xanthosinate 5'-monophosphate (XMP).	2006-12-14	17117222
Transgenic tobacco plants producing caffeine: a potential new strategy for insect pest control.	2006-12	17091387
Functional characterization of nucleoside transporter gene replacements in Leishmania donovani.	2006-12	17050001
Profiles of purine biosynthesis, salvage and degradation in disks of potato (Solanum tuberosum L.) tubers.	2006-12	16845529
Recent advances in structure and function of cytosolic IMP-GMP specific 5'-nucleotidase II (cN-II).	2006-11	18404470
First joint italian-german purine club meeting "progress in purinergic receptor pharmacology and function".	2006-11	18404458
Acid-base and metal-ion-binding properties of xanthosine 5'-monophosphate (XMP) in aqueous solution: complex stabilities, isomeric equilibria, and extent of macrochelation.	2006-10-25	16888737
[Nucleoside-5'-triphosphate hydrolysis in the liver and kidney of rats with chronic alloxan diabetes].	2006-10-19	17044594
Determination of inosine monophosphate dehydrogenase activity in human CD4+ cells isolated from whole blood during mycophenolic acid therapy.	2006-10	17038874
Validation and application of a high-performance liquid chromatographic-based assay for determination of the inosine 5'-monophosphate dehydrogenase activity in erythrocytes.	2006-09-14	16725387
The EF-G-like GTPase Snu114p regulates spliceosome dynamics mediated by Brr2p, a DExD/H box ATPase.	2006-08-04	16885028
In-source CID of guanosine: gas phase ion-molecule reactions.	2006-08	16750381
Calcium-stimulated guanosine--inosine nucleosidase from yellow lupin (Lupinus luteus).	2006-07	16820181
Modified nucleosides: an accurate tumour marker for clinical diagnosis of cancer, early detection and therapy control.	2006-06-05	16685264
Caffeine biosynthesis and adenine metabolism in transgenic Coffea canephora plants with reduced expression of N-methyltransferase genes.	2006-05	16624354
A combined computational and experimental study of the hydrogen-bonded dimers of xanthine and hypoxanthine.	2005-03-03	16833495
Solvatochromism of a novel betaine dye derived from purine.	2005-02-10	16838944

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:55:36 GMT 2025` Edited by `admin` on `Mon Mar 31 19:55:36 GMT 2025`
Record UNII	BM66HT53C3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

XANTHOSINE

Systematic Name

English

NSC-18930

Preferred Name

English

XANTHOSINE [MI]

Common Name

English

XANTHINE RIBOSIDE

Common Name

English

9-.BETA.-D-RIBOFURANOSYL XANTHINE

Common Name

English

1H-PURINE-2,6-DIONE, 3,9-DIHYDRO-9-.BETA.-D-RIBOFURANOSYL-

Systematic Name

English

Code System Code Type Description

ECHA (EC/EINECS)

205-679-9