Riboprine

Details

• Internal ID: 64208699-21c7-4c00-9153-03f7717dba30
• Taxonomy: Nucleosides, nucleotides, and analogues > Purine nucleosides
• IUPAC Name: (2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(3-methylbut-2-enylamino)purin-9-yl]oxolane-3,4-diol
• SMILES (Canonical): CC(=CCNC1=C2C(=NC=N1)N(C=N2)C3C(C(C(O3)CO)O)O)C
• SMILES (Isomeric): CC(=CCNC1=C2C(=NC=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)C
• InChI: InChI=1S/C15H21N5O4/c1-8(2)3-4-16-13-10-14(18-6-17-13)20(7-19-10)15-12(23)11(22)9(5-21)24-15/h3,6-7,9,11-12,15,21-23H,4-5H2,1-2H3,(H,16,17,18)/t9-,11-,12-,15-/m1/s1
• InChI Key: USVMJSALORZVDV-SDBHATRESA-N
• Popularity: 349 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₁N₅O₄
• Molecular Weight: 335.36 g/mol
• Exact Mass: 335.15935417 g/mol
• Topological Polar Surface Area (TPSA): 126.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): -0.18
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• Riboprine
• Isopentenyladenosine
• N6-Isopentenyladenosine
• 2iPA
• Riboprina
• Isopentenyladenosine riboside
• Riboprinum
• ADENOSINE, N-(3-METHYL-2-BUTENYL)-
• 2-IPA
• 6-(3-Methyl-2-butenylamino)purine riboside
• N-(3-methylbut-2-en-1-yl)adenosine
• N-Isopentenyladenosine
• 8EU82FAZ5J
• NSC-105546
• N6-(2-isopentenyl)-adenosine
• DTXSID1057828
• CHEBI:62881
• N(6)-(Delta(2)-isopentenyl)adenosine
• (2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(3-methylbut-2-enylamino)purin-9-yl]oxolane-3,4-diol
• DTXCID2031617
• (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-(3-methylbut-2-enylamino)purin-9-yl)oxolane-3,4-diol
• RefChem:923758
• 231-771-3
• N6-(3-Methyl-2-butenyl)adenosine
• N6-(2-Isopentenyl)adenosine
• N-(3-Methyl-2-butenyl)adenosine
• N6-ISOPENTENYLADENOSINE-D6
• Isopentenyl adenosine
• 6-(gamma,gamma-Dimethylallylamino)purine riboside
• MFCD00005741
• Dimethylallyladenosine
• Isopentenyl adenine riboside
• N(6)-(2-isopentenyl)adenosine
• N-(3-methylbut-2-enyl)adenosine
• N(6)-(3-methyl-2-butenyl)adenosine
• SQ 22558
• ZK 20 242
• 6-(3,3-Dimethylallylamino)-9-(b-D-ribofuranosyl)purine
• Riboprine [USAN:INN]
• Riboprinum [INN-Latin]
• 6-N-((3-Methyl-2-butenyl)amino)-9-.beta.-D-ribofuranosyl-9H-purine
• Riboprina [INN-Spanish]
• 2iP Riboside
• (2R,3S,4R,5R)-2-(Hydroxymethyl)-5-(6-((3-methylbut-2-en-1-yl)amino)-9H-purin-9-yl)tetrahydrofuran-3,4-diol
• i6a
• N(sup 6)-Isopentenyladenosine
• N(sup 6)-Dimethylallyladenosine
• EINECS 231-771-3
• N(sup 6)-(2-Isopentenyl)adenosine
• UNII-8EU82FAZ5J
• NSC 105546
• Riboprin
• N(sup 6)-(delta(sup 2)-Isopentenyl)adenosine
• Ribosyl-deoxyzeatin
• ZIR
• RIBOPRINE [INN]
• 6-N-((3-Methyl-2-butenyl)amino)-9beta-D-ribofuranosylpurine
• 9beta-D-Ribofuranosyl-9H-purine, N-(3-methyl-2-butenylamino)-
• Riboprine (USAN/INN)
• N6-Dimethylallyladenosine
• RIBOPRINE [USAN]
• 6-N-((3-Methyl-2-butenyl)amino)-9-beta-D-ribofuranosyl-9H-purine
• SCHEMBL4599
• 6-N-((3-Methyl-2-butenyl)amino)-9.beta.-D-ribofuranosylpurine
• CHEMBL452867
• orb1303128
• SCHEMBL29552839
• 6-(3,3-Dimethylallylamino)-9-(beta-D-ribofuranosyl)purine
• MSK15113
• Tox21_113776
• AKOS016009606
• CS-W011925
• DB11933
• DS-5147
• HY-W011209
• ND08001
• NCGC00253650-01
• BP-58623
• SY077310
• adenosine, N(6)-(3-methyl-2-butenyl)-
• Adenosine, N-(3-methyl-2-buten-1-yl)-
• CAS-7724-76-7
• 2iP Riboside; N6-(2-Isopentenyl)adenosine
• N6-(.DELTA.2-Isopentenyl)adenine riboside
• N6-(3,3-Dimethylallylamino)purine riboside
• N6-(.gamma.,.gamma.-Dimethylallyl)adenosine
• NS00037896
• D05726
• 724G767
• F239110
• Q973089
• SR-01000883994
• SR-01000883994-1
• 6-( gamma , gamma -Dimethylallylamino)purine riboside
• N6-(| currency2-isopentenyl)adenosine pound IPA)
• (2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(3-methylbut-2-enylamino)purin-9-yl]tetrahydrofuran-3,4-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8673	86.73%
Caco-2	-	0.8579	85.79%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.2994	29.94%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9263	92.63%
OATP1B3 inhibitior	+	0.9417	94.17%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9700	97.00%
P-glycoprotein inhibitior	-	0.8674	86.74%
P-glycoprotein substrate	-	0.8311	83.11%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8682	86.82%
CYP3A4 inhibition	-	0.9661	96.61%
CYP2C9 inhibition	-	0.9233	92.33%
CYP2C19 inhibition	-	0.9103	91.03%
CYP2D6 inhibition	-	0.9290	92.90%
CYP1A2 inhibition	-	0.8874	88.74%
CYP2C8 inhibition	-	0.8488	84.88%
CYP inhibitory promiscuity	-	0.9190	91.90%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5971	59.71%
Eye corrosion	-	0.9860	98.60%
Eye irritation	-	0.9621	96.21%
Skin irritation	-	0.7503	75.03%
Skin corrosion	-	0.9261	92.61%
Ames mutagenesis	+	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5879	58.79%
Micronuclear	+	0.9700	97.00%
Hepatotoxicity	-	0.5932	59.32%
skin sensitisation	-	0.8432	84.32%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.5935	59.35%
Acute Oral Toxicity (c)	III	0.5234	52.34%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.6585	65.85%
Thyroid receptor binding	+	0.7036	70.36%
Glucocorticoid receptor binding	-	0.5207	52.07%
Aromatase binding	+	0.8070	80.70%
PPAR gamma	+	0.6165	61.65%
Honey bee toxicity	-	0.8429	84.29%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.8200	82.00%
Fish aquatic toxicity	-	0.4291	42.91%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3589	P55263	Adenosine kinase	98.34%	98.05%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.46%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	95.13%	95.93%
CHEMBL3401	O75469	Pregnane X receptor	94.82%	94.73%
CHEMBL3038469	P24941	CDK2/Cyclin A	94.40%	91.38%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.69%	91.11%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	90.33%	93.10%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	89.11%	80.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	87.12%	95.83%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.98%	99.17%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.08%	96.90%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.58%	94.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	83.16%	95.64%
CHEMBL5524	Q99873	Protein-arginine N-methyltransferase 1	83.13%	96.67%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	82.77%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.09%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.75%	95.89%

Plants that contains it

• Arabidopsis thaliana
• Ginkgo biloba

Cross-Links

• PubChem: 24405
• NPASS: NPC239737
• ChEMBL: CHEMBL452867
• LOTUS: LTS0001872
• wikiData: Q973089