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

Details

• Internal ID: af6de76a-ee9e-4eff-a5c2-dd2ba46311e0
• Taxonomy: Nucleosides, nucleotides, and analogues > Purine nucleosides
• IUPAC Name: 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one
• SMILES (Canonical): C1=NC(=O)C2=C(N1)N(C=N2)C3C(C(C(O3)CO)O)O
• SMILES (Isomeric): C1=NC(=O)C2=C(N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O
• InChI: InChI=1S/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7-,10-/m1/s1
• InChI Key: UGQMRVRMYYASKQ-KQYNXXCUSA-N
• Popularity: 108 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: -2.10
• Atomic LogP (AlogP): -2.27
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6680	66.80%
Caco-2	-	0.9502	95.02%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Nucleus	0.4950	49.50%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9207	92.07%
OATP1B3 inhibitior	+	0.9504	95.04%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9188	91.88%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	-	0.9217	92.17%
CYP3A4 substrate	-	0.5657	56.57%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8757	87.57%
CYP3A4 inhibition	-	0.9825	98.25%
CYP2C9 inhibition	-	0.9637	96.37%
CYP2C19 inhibition	-	0.9607	96.07%
CYP2D6 inhibition	-	0.9629	96.29%
CYP1A2 inhibition	-	0.8425	84.25%
CYP2C8 inhibition	-	0.9360	93.60%
CYP inhibitory promiscuity	-	0.9540	95.40%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6628	66.28%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9443	94.43%
Skin irritation	-	0.7717	77.17%
Skin corrosion	-	0.9423	94.23%
Ames mutagenesis	+	0.7109	71.09%
Human Ether-a-go-go-Related Gene inhibition	-	0.7271	72.71%
Micronuclear	+	0.9700	97.00%
Hepatotoxicity	+	0.6349	63.49%
skin sensitisation	-	0.8686	86.86%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.8179	81.79%
Acute Oral Toxicity (c)	III	0.5175	51.75%
Estrogen receptor binding	-	0.6354	63.54%
Androgen receptor binding	+	0.5804	58.04%
Thyroid receptor binding	-	0.5156	51.56%
Glucocorticoid receptor binding	-	0.4760	47.60%
Aromatase binding	+	0.8198	81.98%
PPAR gamma	+	0.6782	67.82%
Honey bee toxicity	-	0.8729	87.29%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	-	0.8379	83.79%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293232	Q16637	Survival motor neuron protein	1258.9 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.47%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.07%	95.93%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.26%	94.00%
CHEMBL2581	P07339	Cathepsin D	88.01%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.33%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	86.72%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.63%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.10%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.74%	91.11%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.63%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.32%	97.09%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	82.22%	100.00%
CHEMBL2850	P49840	Glycogen synthase kinase-3 alpha	82.06%	88.84%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	81.83%	80.33%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.42%	90.08%

Plants that contains it

• Allium tuberosum
• Arabidopsis thaliana
• Capsicum annuum
• Cichorium pumilum
• Euryale ferox
• Fritillaria cirrhosa
• Fritillaria delavayi
• Fritillaria monantha
• Fritillaria pallidiflora
• Fritillaria przewalskii
• Fritillaria taipaiensis
• Fritillaria thunbergii
• Fritillaria unibracteata
• Fritillaria verticillata
• Fritillaria walujewii
• Pinellia ternata
• Reboulia hemisphaerica
• Typha angustifolia
• Typha orientalis
• Ziziphus jujuba

Cross-Links

• PubChem: 6021
• NPASS: NPC54320
• ChEMBL: CHEMBL1556
• LOTUS: LTS0273582
• wikiData: Q422564