Xanthosine

Details

• Internal ID: ee35e01e-bf3d-493b-9de2-7f01d2783ff8
• Taxonomy: Nucleosides, nucleotides, and analogues > Purine nucleosides
• IUPAC Name: 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-2,6-dione
• SMILES (Canonical): C1=NC2=C(N1C3C(C(C(O3)CO)O)O)NC(=O)NC2=O
• SMILES (Isomeric): C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)NC(=O)NC2=O
• InChI: 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
• InChI Key: UBORTCNDUKBEOP-UUOKFMHZSA-N
• Popularity: 854 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₂N₄O₆
• Molecular Weight: 284.23 g/mol
• Exact Mass: 284.07568412 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: -2.40
• Atomic LogP (AlogP): -2.98
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 2

Synonyms

• 146-80-5
• Xanthine riboside
• 9-beta-D-Ribofuranosylxanthine
• 2,3-Dihydroxanthosine
• beta-D-Ribofuranoside, xanthine-9
• UNII-BM66HT53C3
• 9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purine-2,6-diol
• AI3-52693
• BM66HT53C3
• CHEBI:18107
• EINECS 205-679-9
• NSC 18930
• 1H-Purine-2,6-dione, 3,9-dihydro-9-beta-D-ribofuranosyl-
• 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-2,6-dione
• xanthosin
• NSC-18930
• 4UO
• XANTHOSINE [MI]
• Xanthosine, 9-beta-D-
• 9-D-Ribofuranosylxanthine
• bmse000128
• 2,3-Dihydro-2-oxoinosine
• 9-b-D-Ribofuranosylxanthine
• 9-delta-Ribofuranosylxanthine
• 1H-Purine-2,6-dione, 3,9-dihydro-9-.beta.-D-ribofuranosyl-
• SCHEMBL133792
• 9 beta-D-ribofuranosylxanthine
• CHEMBL402439
• xanthine 9-beta-D-ribofuranoside
• DTXSID90861829
• 9-beta-delta-Ribofuranosylxanthine
• C10H12N4O6
• s9369
• AKOS024282554
• CCG-267285
• CS-W012243
• GS-3230
• HY-W011527
• 9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-dihydropurine -2,6-dione
• 9-.BETA.-D-RIBOFURANOSYL XANTHINE
• X0008
• C01762
• A848549
• Q408788
• 3,9-Dihydro-9-D-ribofuranosyl-1H-purine-2,6-dione
• 2,3-Dihydro-2-Oxoinosine; Nsc 18930; Stk246877;
• 3,9-Dihydro-9-b-D-ribofuranosyl-1H-purine-2,6-dione
• 3,9-Dihydro-9-delta-ribofuranosyl-1H-purine-2,6-dione
• 185DA837-1A29-446F-A96C-EBBA1B464566
• 9-beta-D-ribofuranosyl-3,9-dihydro-1H-purine-2,6-dione
• 3,9-Dihydro-9-beta-delta-ribofuranosyl-1H-purine-2,6-dione
• 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purine-2,6-diol
• 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purine-2,6-diol
• 9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purine-2,6(3H,9H)-dione
• 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,3,6,9-tetrahydro-1H-purine-2,6-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6714	67.14%
Caco-2	-	0.9688	96.88%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Nucleus	0.5391	53.91%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9235	92.35%
OATP1B3 inhibitior	+	0.9495	94.95%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9405	94.05%
P-glycoprotein inhibitior	-	0.9246	92.46%
P-glycoprotein substrate	-	0.9228	92.28%
CYP3A4 substrate	-	0.5741	57.41%
CYP2C9 substrate	-	0.7939	79.39%
CYP2D6 substrate	-	0.8681	86.81%
CYP3A4 inhibition	-	0.9842	98.42%
CYP2C9 inhibition	-	0.9704	97.04%
CYP2C19 inhibition	-	0.9521	95.21%
CYP2D6 inhibition	-	0.9527	95.27%
CYP1A2 inhibition	-	0.8027	80.27%
CYP2C8 inhibition	-	0.9492	94.92%
CYP inhibitory promiscuity	-	0.9904	99.04%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6658	66.58%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9505	95.05%
Skin irritation	-	0.7465	74.65%
Skin corrosion	-	0.9412	94.12%
Ames mutagenesis	-	0.5461	54.61%
Human Ether-a-go-go-Related Gene inhibition	-	0.6336	63.36%
Micronuclear	+	0.9800	98.00%
Hepatotoxicity	+	0.5780	57.80%
skin sensitisation	-	0.8434	84.34%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.6559	65.59%
Acute Oral Toxicity (c)	III	0.5593	55.93%
Estrogen receptor binding	-	0.6700	67.00%
Androgen receptor binding	-	0.4838	48.38%
Thyroid receptor binding	-	0.5477	54.77%
Glucocorticoid receptor binding	-	0.5838	58.38%
Aromatase binding	+	0.7373	73.73%
PPAR gamma	+	0.6442	64.42%
Honey bee toxicity	-	0.9137	91.37%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.8400	84.00%
Fish aquatic toxicity	-	0.7655	76.55%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.67%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.81%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	91.56%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.00%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.41%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.71%	94.45%
CHEMBL2424504	P29375	Lysine-specific demethylase 5A	84.00%	99.23%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	83.76%	80.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.46%	89.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	81.76%	90.08%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.72%	95.56%
CHEMBL2581	P07339	Cathepsin D	81.36%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	80.75%	95.93%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	80.16%	95.48%

Plants that contains it

• Arabidopsis thaliana
• Camellia sinensis
• Hyacinthoides non-scripta
• Tribulus terrestris

Cross-Links

• PubChem: 64959
• NPASS: NPC311197
• LOTUS: LTS0192214
• wikiData: Q408788