Nebularine

Details

• Internal ID: 9742d5ce-285a-428b-9cba-b7874ef54aef
• Taxonomy: Nucleosides, nucleotides, and analogues > Purine nucleosides
• IUPAC Name: (2R,3S,4R,5R)-2-(hydroxymethyl)-5-purin-9-yloxolane-3,4-diol
• SMILES (Canonical): C1=C2C(=NC=N1)N(C=N2)C3C(C(C(O3)CO)O)O
• SMILES (Isomeric): C1=C2C(=NC=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O
• InChI: InChI=1S/C10H12N4O4/c15-2-6-7(16)8(17)10(18-6)14-4-13-5-1-11-3-12-9(5)14/h1,3-4,6-8,10,15-17H,2H2/t6-,7-,8-,10-/m1/s1
• InChI Key: MRWXACSTFXYYMV-FDDDBJFASA-N
• Popularity: 177 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₂N₄O₄
• Molecular Weight: 252.23 g/mol
• Exact Mass: 252.08585488 g/mol
• Topological Polar Surface Area (TPSA): 114.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -1.56
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• 550-33-4
• Purine riboside
• Purine ribonucleoside
• Purine nucleoside
• N-D-Ribosylpurine
• Purine, ribosyl-
• Isopurine, ribosyl-
• (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(9H-purin-9-yl)tetrahydrofuran-3,4-diol
• 9-(beta-D-Ribofuranosyl)purine
• B8B604PS4P
• 9-beta-Ribofuranosylpurine
• CHEMBL1399702
• CHEBI:18255
• (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(9H-purin-9-yl)oxolane-3,4-diol
• 9-(beta-D-ribofuranosyl)-9H-purine
• 9-beta-D-Ribofuranosyl-9H-purine
• Nebularin E)
• 1fkw
• 9H-Purine, 9beta-D-ribofuranosyl-
• EINECS 208-981-9
• 9H-Purine, 9-beta-D-ribofuranosyl-
• BRN 0091539
• UNII-B8B604PS4P
• NSC-65423
• 9-.beta.-D-Ribofuranosyl-9H-purine
• 9H-Purine, 9.beta.-D-ribofuranosyl-
• PUR
• NEBULARINE [MI]
• Lopac0_000423
• SCHEMBL93409
• 4-26-00-01740 (Beilstein Handbook Reference)
• MRWXACSTFXYYMV-FDDDBJFASA-N
• DTXSID701015580
• HMS3261E08
• Tox21_500423
• BDBM50335291
• HB3992
• MFCD00022819
• AKOS027327572
• CCG-204515
• DB04440
• LP00423
• SDCCGSBI-0050408.P002
• NCGC00093846-01
• NCGC00093846-02
• NCGC00093846-03
• NCGC00093846-04
• NCGC00261108-01
• AS-35125
• EU-0100423
• C01736
• D 8296
• EN300-7400810
• SR-01000075836
• Q3874106
• SR-01000075836-1
• 9-(beta-D-Ribofuranosyl)-9H-purine; 6-deaminoadenosine
• Z3002630759
• (2R,3S,4R,5R)-2-(hydroxymethyl)-5-purin-9-yl-tetrahydrofuran-3,4-diol
• (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(9H-purin-9-yl)-tetrahydrofuran-3,4-diol;NSC 65423;Nebularine;Purinosine;NSC65423;ST055522

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5915	59.15%
Caco-2	-	0.8658	86.58%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Nucleus	0.3657	36.57%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9319	93.19%
OATP1B3 inhibitior	+	0.9496	94.96%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9332	93.32%
P-glycoprotein inhibitior	-	0.9353	93.53%
P-glycoprotein substrate	-	0.9213	92.13%
CYP3A4 substrate	-	0.5979	59.79%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8302	83.02%
CYP3A4 inhibition	-	0.9813	98.13%
CYP2C9 inhibition	-	0.9618	96.18%
CYP2C19 inhibition	-	0.9530	95.30%
CYP2D6 inhibition	-	0.9698	96.98%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.7586	75.86%
CYP inhibitory promiscuity	-	0.9629	96.29%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6334	63.34%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.8520	85.20%
Skin irritation	-	0.7630	76.30%
Skin corrosion	-	0.9397	93.97%
Ames mutagenesis	-	0.6645	66.45%
Human Ether-a-go-go-Related Gene inhibition	-	0.5895	58.95%
Micronuclear	+	0.9700	97.00%
Hepatotoxicity	-	0.5545	55.45%
skin sensitisation	-	0.8676	86.76%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.7798	77.98%
Acute Oral Toxicity (c)	III	0.4474	44.74%
Estrogen receptor binding	-	0.6600	66.00%
Androgen receptor binding	+	0.5373	53.73%
Thyroid receptor binding	+	0.5475	54.75%
Glucocorticoid receptor binding	+	0.5687	56.87%
Aromatase binding	+	0.6973	69.73%
PPAR gamma	+	0.5206	52.06%
Honey bee toxicity	-	0.9166	91.66%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	-	0.9114	91.14%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293237	P54132	Bloom syndrome protein	1.1 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3589	P55263	Adenosine kinase	97.71%	98.05%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.00%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.11%	97.36%
CHEMBL226	P30542	Adenosine A1 receptor	92.23%	95.93%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	90.21%	98.46%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.18%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.60%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	86.59%	94.73%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	85.02%	80.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.08%	89.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	83.73%	95.64%
CHEMBL5524	Q99873	Protein-arginine N-methyltransferase 1	82.79%	96.67%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	82.64%	93.10%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.39%	86.33%
CHEMBL3038469	P24941	CDK2/Cyclin A	82.33%	91.38%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	81.87%	100.00%

Plants that contains it

• Medicago sativa

Cross-Links

• PubChem: 68368
• LOTUS: LTS0017469
• wikiData: Q3874106