Zeatin riboside

Details

• Internal ID: b9a5e9d6-9b9e-449e-9a27-3e05af76d90b
• Taxonomy: Nucleosides, nucleotides, and analogues > Purine nucleosides
• IUPAC Name: (2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-[[(E)-4-hydroxy-3-methylbut-2-enyl]amino]purin-9-yl]oxolane-3,4-diol
• SMILES (Canonical): CC(=CCNC1=C2C(=NC=N1)N(C=N2)C3C(C(C(O3)CO)O)O)CO
• SMILES (Isomeric): C/C(=C\CNC1=C2C(=NC=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)/CO
• InChI: InChI=1S/C15H21N5O5/c1-8(4-21)2-3-16-13-10-14(18-6-17-13)20(7-19-10)15-12(24)11(23)9(5-22)25-15/h2,6-7,9,11-12,15,21-24H,3-5H2,1H3,(H,16,17,18)/b8-2+/t9-,11-,12-,15-/m1/s1
• InChI Key: GOSWTRUMMSCNCW-HNNGNKQASA-N
• Popularity: 533 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₁N₅O₅
• Molecular Weight: 351.36 g/mol
• Exact Mass: 351.15426879 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -1.21
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

• Zeatin riboside
• Ribosylzeatin
• 9-Ribosyl-trans-zeatin
• N-(4-Hydroxy-3-methyl-2-butenyl)adenosine
• (E)-N-(4-Hydroxy-3-methyl-2-butenyl)adenosine
• 7LG4D082A9
• N-[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]adenosine
• CHEBI:71693
• n-((2e)-4-hydroxy-3-methylbut-2-en-1-yl)adenosine
• DTXSID00891556
• RefChem:898921
• DTXCID701030649
• trans-Zeatin-riboside
• trans-Zeatinriboside
• Trans-zeatin riboside
• 28542-78-1
• MFCD00036809
• Adenosine, N-[(2E)-4-hydroxy-3-methyl-2-butenyl]-
• C15H21N5O5
• (2R,3R,4S,5R)-2-(6-(((E)-4-Hydroxy-3-methylbut-2-en-1-yl)amino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
• 9-(beta-D-Ribofuranosyl)-trans-zeatin
• 9-beta-D-ribosyl-trans-zeatin
• 9-beta-D-ribofuranosyl-trans-zeatin
• trans-zeatin 9-beta-D-ribofuranoside
• N6-(trans-4-Hydroxy-3-methyl-2-buten-1-yl)adenosine
• (2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-[[(E)-4-hydroxy-3-methylbut-2-enyl]amino]purin-9-yl]oxolane-3,4-diol
• Adenosine, N-(4-hydroxy-3-methyl-2-butenyl)-, (E)-
• 6-((E)-4-hydroxy-3-methylbut-2-enylamino)-9-b-Dribofuranosylpurine
• (2R,3R,4S,5R)-2-(6-((4-Hydroxy-3-methylbut-2-en-1-yl)amino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
• UNII-7LG4D082A9
• 6-[(E)-4-Hydroxy-3-methylbut-2-enylamino]-9-b-D-ribofuranosylpurine
• 6-[(E)-4-Hydroxy-3-methylbut-2-enylamino]-9-beta-D-ribofuranosylpurine
• Ribosyl-trans-zeatin
• Zeatin ribonucleoside
• AC1O5UJN
• UPCMLD-DP150
• Adenosine, N-(4-hydroxy-3-methyl-2-butenyl)-
• Zeatin riboside, trans-isomer
• trans-Zeatin-riboside, ~95%
• SCHEMBL4058989
• 9-.beta.-D-Ribofuranosylzeatin
• Zeatin 9-.beta.-ribonucleoside
• SCHEMBL29373945
• UPCMLD-DP150:001
• UPCMLD-DP150:002
• DTXSID101017776
• (2R,3R,4S,5R)-2-(6-{[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]amino}-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• MSK15112
• Q3V
• CZ-007
• s5678
• 9-(|A-D-Ribofuranosyl)-trans-zeatin
• AKOS016003311
• CCG-268042
• CS-W011867
• HY-W011151
• NZ30302
• Zeatin, 9-beta-ribofuranosyl-, trans-
• 9-(I(2)-D-Ribofuranosyl)-trans-zeatin
• NCGC00161675-01
• AC-32196
• DA-58705
• DS-11490
• SY076414
• M02693
• 025Z532
• N-[(2E)-4-Hydroxy-3-methyl-2-buten-1-yl]adenosine
• Q27139815
• Adenosine,N-[(2E)-4-hydroxy-3-methyl-2-buten-1-yl]-
• 17493EE6-B91F-4EAF-901B-25B5904BCD54
• 6-(4-Hydroxy-3-methyl-2-butenylamino)-9-D-ribofuranosylpurine
• Adenosine, N-[(2E)-4-hydroxy-3-methyl-2-buten-1-yl]- [
• trans-Zeatin-riboside, BioReagent, plant cell culture tested, ~95%
• 6-[(E)-4-Hydroxy-3-methylbut-2-enylamino]-9-beta-D-ribofuranosylpurine, 97%

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8965	89.65%
Caco-2	-	0.8733	87.33%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Plasma membrane	0.3833	38.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9222	92.22%
OATP1B3 inhibitior	+	0.9418	94.18%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9552	95.52%
P-glycoprotein inhibitior	-	0.8815	88.15%
P-glycoprotein substrate	-	0.7601	76.01%
CYP3A4 substrate	+	0.5334	53.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8682	86.82%
CYP3A4 inhibition	-	0.9889	98.89%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9385	93.85%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.8174	81.74%
CYP inhibitory promiscuity	-	0.9345	93.45%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5932	59.32%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.9690	96.90%
Skin irritation	-	0.7477	74.77%
Skin corrosion	-	0.9257	92.57%
Ames mutagenesis	+	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5142	51.42%
Micronuclear	+	0.9700	97.00%
Hepatotoxicity	-	0.6078	60.78%
skin sensitisation	-	0.8482	84.82%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.6332	63.32%
Acute Oral Toxicity (c)	III	0.5119	51.19%
Estrogen receptor binding	+	0.7210	72.10%
Androgen receptor binding	+	0.6789	67.89%
Thyroid receptor binding	+	0.6128	61.28%
Glucocorticoid receptor binding	-	0.4918	49.18%
Aromatase binding	+	0.8143	81.43%
PPAR gamma	+	0.6051	60.51%
Honey bee toxicity	-	0.8391	83.91%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.8100	81.00%
Fish aquatic toxicity	+	0.7614	76.14%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3589	P55263	Adenosine kinase	98.40%	98.05%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.22%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	95.91%	95.93%
CHEMBL3401	O75469	Pregnane X receptor	94.04%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.45%	91.11%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	91.67%	80.33%
CHEMBL3038469	P24941	CDK2/Cyclin A	88.58%	91.38%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	87.91%	93.10%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	86.49%	95.64%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.71%	89.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.46%	95.83%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.05%	99.17%
CHEMBL5524	Q99873	Protein-arginine N-methyltransferase 1	84.35%	96.67%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.58%	94.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.15%	96.90%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	82.95%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.31%	96.00%
CHEMBL2581	P07339	Cathepsin D	81.02%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.42%	86.33%

Plants that contains it

• Abies balsamea
• Arabidopsis thaliana
• Brassica napus
• Ipomoea batatas
• Lablab purpureus subsp. purpureus
• Medicago sativa
• Phaseolus vulgaris
• Picea sitchensis
• Pinus radiata
• Pseudotsuga menziesii
• Sicyos edulis
• Triticum aestivum
• Zea mays

Cross-Links

• PubChem: 6440982
• NPASS: NPC27600
• LOTUS: LTS0254495
• wikiData: Q27139815