Allopurinol riboside

Details

• Internal ID: cf6cdc2c-d6fe-4c10-b980-4cd57c1b6745
• Taxonomy: Nucleosides, nucleotides, and analogues > Pyrazolo[3,4-d]pyrimidine glycosides
• IUPAC Name: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5H-pyrazolo[3,4-d]pyrimidin-4-one
• SMILES (Canonical): C1=NN(C2=C1C(=O)NC=N2)C3C(C(C(O3)CO)O)O
• SMILES (Isomeric): C1=NN(C2=C1C(=O)NC=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O
• InChI: InChI=1S/C10H12N4O5/c15-2-5-6(16)7(17)10(19-5)14-8-4(1-13-14)9(18)12-3-11-8/h1,3,5-7,10,15-17H,2H2,(H,11,12,18)/t5-,6-,7-,10-/m1/s1
• InChI Key: KFQUAMTWOJHPEJ-DAGMQNCNSA-N
• Popularity: 46 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₂N₄O₅
• Molecular Weight: 268.23 g/mol
• Exact Mass: 268.08076950 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: -2.30
• Atomic LogP (AlogP): -2.27
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• 16220-07-8
• Allopurinol ribonucleoside
• Allopurinol-1-ribonucleoside
• WZS8452SEC
• 4-Hydroxy[3,4-d]pyrazolopyrimidine riboside
• CHEMBL1688966
• CHEBI:74074
• 4H-Pyrazolo[3,4-d]pyrimidin-4-one, 1,5-dihydro-1-beta-D-ribofuranosyl-
• 4-Hydroxy(3,4-d)pyrazolopyrimidine riboside
• 1-[(2R,3R,4S,5R)-3,4-DIHYDROXY-5-(HYDROXYMETHYL)OXOLAN-2-YL]-5H-PYRAZOLO[3,4-D]PYRIMIDIN-4-ONE
• 4H-Pyrazolo(3,4-d)pyrimidin-4-one, 1,5-dihydro-1-.beta.-D-ribofuranosyl-
• UNII-WZS8452SEC
• 4H-Pyrazolo(3,4-d)pyrimidin-4-one, 1,5-dihydro-1-beta-D-ribofuranosyl-
• NSC-138437
• NSC-252629
• NSC 138437
• 8-Aza-7-deazainosine
• CHEMBL603304
• SCHEMBL6912039
• SCHEMBL11672972
• SCHEMBL11673117
• 4-Hydroxy-1beta-D-ribofuranosylpyrazolo(3,4-d)pyrimidine
• KFQUAMTWOJHPEJ-DAGMQNCNSA-N
• 1-beta-D-Ribofuranosyl-1H-pyrazolo[3,4-d]pyrimidine-4-one
• BDBM50366805
• AKOS040740689
• CS-6408
• MS-23785
• HY-101397
• 4-Hydroxy-1H-pyrazolo[3,4-D]pyrimidine riboside
• Q27144387
• 1-.beta.-D-ribofuranosylpyrazolo[3,4-d]pyrimidine-4-one
• 1H-Pyrazolo[3,4-d]pyrimidin-4-ol, 1-.beta.-D-ribofuranosyl-
• 1,5-Dihydro-1-beta-D-ribofuranosyl-4H-pyrazolo(3,4-d)pyrimidin-4-one
• 1-(beta-D-ribofuranosyl)-1,7-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
• 1-(.beta.-D-Ribofuranosyl)-1,5-dihydro-4H- pyrazolo-[3,4-d]pyrimidin-4-one
• (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(4-hydroxypyrazolo[3,4-d]pyrimidin-1-yl)tetrahydrofuran-3,4-diol
• 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one
• 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-2H-pyrazolo[3,4-d]pyrimidin-4-one
• 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5H-pyrazolo[3,4-d]pyrimidin-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7393	73.93%
Caco-2	-	0.9267	92.67%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.4682	46.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9089	90.89%
OATP1B3 inhibitior	+	0.9482	94.82%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9566	95.66%
P-glycoprotein inhibitior	-	0.9232	92.32%
P-glycoprotein substrate	-	0.8614	86.14%
CYP3A4 substrate	-	0.5344	53.44%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8714	87.14%
CYP3A4 inhibition	-	0.9644	96.44%
CYP2C9 inhibition	-	0.9346	93.46%
CYP2C19 inhibition	-	0.9245	92.45%
CYP2D6 inhibition	-	0.9455	94.55%
CYP1A2 inhibition	-	0.8534	85.34%
CYP2C8 inhibition	-	0.9315	93.15%
CYP inhibitory promiscuity	-	0.9427	94.27%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7069	70.69%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9323	93.23%
Skin irritation	-	0.7856	78.56%
Skin corrosion	-	0.9411	94.11%
Ames mutagenesis	-	0.5354	53.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6822	68.22%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	-	0.5180	51.80%
skin sensitisation	-	0.8612	86.12%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6551	65.51%
Acute Oral Toxicity (c)	III	0.6349	63.49%
Estrogen receptor binding	-	0.5733	57.33%
Androgen receptor binding	-	0.5353	53.53%
Thyroid receptor binding	-	0.5768	57.68%
Glucocorticoid receptor binding	-	0.5757	57.57%
Aromatase binding	+	0.7632	76.32%
PPAR gamma	+	0.6981	69.81%
Honey bee toxicity	-	0.8657	86.57%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	-	0.7811	78.11%

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	94.15%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.26%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.11%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.86%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.44%	94.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	88.40%	89.34%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.10%	95.56%
CHEMBL3384	Q16512	Protein kinase N1	86.72%	80.71%
CHEMBL3535	O76083	Phosphodiesterase 9A	86.58%	98.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.86%	89.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.50%	95.83%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.75%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.31%	86.92%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 135407110
• LOTUS: LTS0162087
• wikiData: Q27144387