Kinetin riboside

Details

• Internal ID: 7ba4eeb1-d44b-47ab-b3f4-c1267cfec07d
• Taxonomy: Nucleosides, nucleotides, and analogues > Purine nucleosides
• IUPAC Name: (2R,3R,4S,5R)-2-[6-(furan-2-ylmethylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• SMILES (Canonical): C1=COC(=C1)CNC2=C3C(=NC=N2)N(C=N3)C4C(C(C(O4)CO)O)O
• SMILES (Isomeric): C1=COC(=C1)CNC2=C3C(=NC=N2)N(C=N3)[C@H]4[C@@H]([C@@H]([C@H](O4)CO)O)O
• InChI: InChI=1S/C15H17N5O5/c21-5-9-11(22)12(23)15(25-9)20-7-19-10-13(17-6-18-14(10)20)16-4-8-2-1-3-24-8/h1-3,6-7,9,11-12,15,21-23H,4-5H2,(H,16,17,18)/t9-,11-,12-,15-/m1/s1
• InChI Key: CAGLGYNQQSIUGX-SDBHATRESA-N
• Popularity: 107 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₇N₅O₅
• Molecular Weight: 347.33 g/mol
• Exact Mass: 347.12296866 g/mol
• Topological Polar Surface Area (TPSA): 139.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): -0.36
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• 4338-47-0
• 6-Furfurylaminopurine riboside
• N6-Furfuryladenosine
• Ribosylkinetin
• CHEMBL411066
• (2R,3R,4S,5R)-2-(6-((Furan-2-ylmethyl)amino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
• NSC 120958
• N-(2-Furanylmethyl)adenosine
• N(sup 6)-Furfuryladenosine
• EINECS 224-389-3
• BRN 0059588
• (2R,3R,4S,5R)-2-[6-(furan-2-ylmethylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• N-(2-Furanylmethyl)-1H-purin-6-amine riboside
• Kinetin-9-riboside
• MFCD00037987
• Spectrum_001277
• SpecPlus_000551
• Spectrum2_001453
• Spectrum3_001101
• Spectrum4_001930
• Spectrum5_000687
• BSPBio_002802
• KBioGR_002280
• KBioSS_001757
• 4-26-00-03686 (Beilstein Handbook Reference)
• MLS002207023
• (-)-KINETIN RIBOSIDE
• DivK1c_006647
• SPBio_001345
• SCHEMBL3190252
• N6-(2-furanylmethyl)-adenosine
• CHEBI:95050
• KBio1_001591
• KBio2_001757
• KBio2_004325
• KBio2_006893
• KBio3_002022
• DTXSID20874669
• CAGLGYNQQSIUGX-SDBHATRESA-N
• (2R,3R,4S,5R)-2-(6-(furan-2-ylmethylamino)-9H-purin-9-yl)-5-(hydroxymethyl)-tetrahydrofuran-3,4-diol
• BDBM50241447
• CCG-38867
• AKOS024282559
• CS-6377
• SDCCGMLS-0066656.P001
• (3S,2R,4R,5R)-5-{6-[(2-furylmethyl)amino]purin-9-yl}-2-(hydroxymethyl)oxolane- 3,4-diol
• SMP1_000170
• NCGC00017361-02
• NCGC00017361-03
• NCGC00017361-04
• NCGC00142491-01
• NCGC00142491-02
• NCGC00142491-03
• AS-76879
• SMR001223878
• HY-101055
• F12926
• SR-05000002609
• SR-05000002609-1
• BRD-K94325918-001-02-0
• BRD-K94325918-001-05-3
• Q27166818
• Kinetin riboside, proapoptotic anitproliferative plant growth regulator
• (2R,3R,4S,5R)-2-[6-(2-furanylmethylamino)-9-purinyl]-5-(hydroxymethyl)oxolane-3,4-diol
• (2R,3R,4S,5R)-2-(6-(furan-2-ylmethylamino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6664	66.64%
Caco-2	-	0.8749	87.49%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Nucleus	0.3494	34.94%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9485	94.85%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8482	84.82%
P-glycoprotein inhibitior	-	0.7694	76.94%
P-glycoprotein substrate	-	0.7853	78.53%
CYP3A4 substrate	+	0.5107	51.07%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8550	85.50%
CYP3A4 inhibition	-	0.9716	97.16%
CYP2C9 inhibition	-	0.9569	95.69%
CYP2C19 inhibition	-	0.9516	95.16%
CYP2D6 inhibition	-	0.9637	96.37%
CYP1A2 inhibition	-	0.9538	95.38%
CYP2C8 inhibition	-	0.7000	70.00%
CYP inhibitory promiscuity	-	0.9286	92.86%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6380	63.80%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9852	98.52%
Skin irritation	-	0.7399	73.99%
Skin corrosion	-	0.9372	93.72%
Ames mutagenesis	+	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	1.0000	100.00%
Hepatotoxicity	-	0.6684	66.84%
skin sensitisation	-	0.8504	85.04%
Respiratory toxicity	+	0.9222	92.22%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.8911	89.11%
Acute Oral Toxicity (c)	II	0.4836	48.36%
Estrogen receptor binding	+	0.8027	80.27%
Androgen receptor binding	+	0.6316	63.16%
Thyroid receptor binding	+	0.6419	64.19%
Glucocorticoid receptor binding	-	0.4895	48.95%
Aromatase binding	+	0.8929	89.29%
PPAR gamma	+	0.6953	69.53%
Honey bee toxicity	-	0.8918	89.18%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	-	0.8986	89.86%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL256	P0DMS8	Adenosine A3 receptor	22 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3589	P55263	Adenosine kinase	98.51%	98.05%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.95%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.40%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.18%	95.93%
CHEMBL3038469	P24941	CDK2/Cyclin A	92.12%	91.38%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.94%	94.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	88.85%	95.83%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	88.77%	80.33%
CHEMBL3401	O75469	Pregnane X receptor	87.52%	94.73%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	86.24%	100.00%
CHEMBL3979	Q03181	Peroxisome proliferator-activated receptor delta	84.79%	93.95%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	84.53%	93.10%
CHEMBL2581	P07339	Cathepsin D	83.71%	98.95%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.33%	89.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.88%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.30%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.42%	99.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.03%	96.00%

Plants that contains it

• Cocos nucifera

Cross-Links

• PubChem: 20345
• LOTUS: LTS0146271
• wikiData: Q27166818