trans-Zeatin-riboside - 10mM in DMSO , CAS No.6025-53-2

CAS: 6025-53-2 Cat. No.: T425005 Molecular Weight: 351.36 Beilstein Registry Number: 5460894 PubChem CID: 6440982

GRADE & PURITY 10mM in DMSO

Synonyms

(E)-N-(4-Hydroxy-3-methyl-2-butenyl)adenosine | Adenosine, N-[(2E)-4-hydroxy-3-methyl-2-butenyl]- | n-((2e)-4-hydroxy-3-methylbut-2-en-1-yl)adenosine | (2R,3R,4S,5R)-2-(6-((4-Hydroxy-3-methylbut-2-en-1-yl)amino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrof

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Specifications

Synonyms

(E)-N-(4-Hydroxy-3-methyl-2-butenyl)adenosine | Adenosine, N-[(2E)-4-hydroxy-3-methyl-2-butenyl]- | n-((2e)-4-hydroxy-3-methylbut-2-en-1-yl)adenosine | (2R, 3R, 4S, 5R)-2-(6-((4-Hydroxy-3-methylbut-2-en-1-yl)amino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrof

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Koenig RL; Morris RO; Polacco JC Trans-zeatin-riboside is a kind of cytokinin precursor, which is an important long-distance signalling form in xylem vessels.It serves as an inhibitory factor in root xylem sap by negatively modulating adventitious root fo

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

• Canonical Smiles: C\C(CO)=C/CNc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O
• 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
• InChIKey: GOSWTRUMMSCNCW-HNNGNKQASA-N
• 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
• Isomeric SMILES: C/C(=C\CNC1=C2C(=NC=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)/CO
• WGK Germany: 3
• Alternate CAS: 28542-78-1
• PubChem CID: 6440982
• Molecular Weight: 351.36
• Beilstein: 5460894

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Class Purine nucleosides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Class: Purine nucleosides
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Purine nucleosides
• Alternative Parents: Glycosylamines 6-alkylaminopurines Pentoses Secondary alkylarylamines Aminopyrimidines and derivatives N-substituted imidazoles Imidolactams Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Oxacyclic compounds Azacyclic compounds Primary alcohols Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Purine nucleoside - Glycosyl compound - N-glycosyl compound - 6-alkylaminopurine - 6-aminopurine - Pentose monosaccharide - Imidazopyrimidine - Purine - Aminopyrimidine - Secondary aliphatic/aromatic amine - Monosaccharide - N-substituted imidazole - Pyrimidine - Imidolactam - Tetrahydrofuran - Azole - Imidazole - Heteroaromatic compound - Secondary alcohol - Organoheterocyclic compound - Azacycle - Secondary amine - Oxacycle - Amine - Organic nitrogen compound - Alcohol - Hydrocarbon derivative - Organopnictogen compound - Organonitrogen compound - Organooxygen compound - Organic oxygen compound - Primary alcohol - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
• External Descriptors: nucleoside analogue - 9-ribosylzeatin

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Molecular Weight: 351.360 g/mol
• XLogP3: -0.100
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 351.154 Da
• Monoisotopic Mass: 351.154 Da
• Topological Polar Surface Area: 146.000 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 481.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Huifeng Deng, Yanqun Yang, Jianbin Ju, Yu Jiang, Xiaowen Huang, Zhenyu Li, Rui Shi, Guihua Ruan, Yipeng Huang.  (2024)  Rapid analysis of six cytokinins in tomato plants using phenylboronic acid and ionic liquid functionalized monolithic capillary column combined with UHPLC-MS/MS.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:39580982] [10.1016/j.chroma.2024.465540]