(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

• ChemBase ID: 105742
• Molecular Formular: C15H21N5O5
• Molecular Mass: 351.35774
• Monoisotopic Mass: 351.1542688
• SMILES: n1c2c(ncnc2NC/C=C(\C)/CO)n(c1)[C@@H]1O[C@@H]([C@@H](O)[C@H]1O)CO
• Canonical SMILES: OC/C(=C/CNc1ncnc2c1ncn2[C@@H]1O[C@@H]([C@H]([C@H]1O)O)CO)/C
• 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
• InChIKey: GOSWTRUMMSCNCW-HNNGNKQASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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
• IUPAC Traditional name: trans-zeatin riboside
• Synonyms: Zeatin riboside mixed Isomers; 9-(β-D-Ribofuranosyl)-trans-zeatin; N6-(trans-4-Hydroxy-3-methyl-2-buten-1-yl)adenosine; trans-Zeatin-riboside; trans-ZEATIN RIBOSIDE

Database IDs

• CAS Number: 28542-78-1; 6025-53-2
• MDL Number: MFCD00036809
• Beilstein Number: 5460894
• PubChem SID: 24902169; 162093824; 24902164; 24902179
• PubChem CID: 6440982

CALCULATED PROPERTIES

• Acid pKa: 12.453119
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -1.7946335
• LogD (pH = 7.4): -1.7099848
• Log P: -1.7087848
• Molar Refractivity: 89.5819 cm^3
• Polarizability: 34.083046 Å^3
• Polar Surface Area: 145.78 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetic acid: soluble50 mg/mL, clear, colorless
• Melting Point: 176-179 °C

Safety Information

• Storage Condition: 0°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ~95%; ≥95% (HPLC)
• Suitability: plant cell culture tested
• Empirical Formula (Hill Notation): C15H21N5O5

DETAILS

MP Biomedicals - 02193903

Purity: ~95%

Sigma Aldrich - Z3541

Biochem/physiol Actions
Koenig RL; Morris RO; Polacco JC

Sigma Aldrich - Z0375

Biochem/physiol Actions
Koenig RL; Morris RO; Polacco JC

Sigma Aldrich - Z0751

Other Notes
Consists of an approximately equal mixture of cis- and trans-isomers; actual percentage given on the label.

Sigma Aldrich - 96089

Other Notes
Cytokinin. Isolation and analysis of cytokinins1
Biochem/physiol Actions
Koenig RL; Morris RO; Polacco JC