Xanthosine

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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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)
SMILES (Isomeric)
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	949 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₀H₁₂N₄O₆
Molecular Weight	284.23 g/mol
Exact Mass	284.07568412 g/mol
Topological Polar Surface Area (TPSA)	146.00 Å²
XlogP	-2.40
Atomic LogP (AlogP)	-2.98
H-Bond Acceptor	8
H-Bond Donor	5
Rotatable Bonds	2

Synonyms

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146-80-5

Xanthine riboside

BM66HT53C3

1H-Purine-2,6-dione, 3,9-dihydro-9-beta-D-ribofuranosyl-

9 beta-D-ribofuranosylxanthine

CHEBI:18107

DTXSID90861829

NSC-18930

9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-2,6-dione

9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-9H-purine-2,6-diol

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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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

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
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

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Arabidopsis thaliana

Camellia sinensis

Hyacinthoides non-scripta

Tribulus terrestris