(2R,3S,5R)-2-(4-{[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]amino}-1H-imidazo[4,5-d]pyridazin-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 170779
• Molecular Formular: C15H21N5O5
• Molecular Mass: 351.35774
• Monoisotopic Mass: 351.1542688
• SMILES: n1ncc2c(c1NC/C=C(/CO)\C)ncn2[C@H]1[C@H](C([C@H](O1)CO)O)O
• Canonical SMILES: OC/C(=C/CNc1nncc2c1ncn2[C@@H]1O[C@@H](C([C@@H]1O)O)CO)/C
• InChI: InChI=1S/C15H21N5O5/c1-8(5-21)2-3-16-14-11-9(4-18-19-14)20(7-17-11)15-13(24)12(23)10(6-22)25-15/h2,4,7,10,12-13,15,21-24H,3,5-6H2,1H3,(H,16,19)/b8-2+/t10-,12?,13+,15-/m1/s1
• InChIKey: HTHPRLCFWPOOIP-BBTRJMPKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,5R)-2-(4-{[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]amino}-1H-imidazo[4,5-d]pyridazin-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3S,5R)-2-(4-{[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]amino}imidazo[4,5-d]pyridazin-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: trans-Zeatin Riboside; 6-[(E)-4-Hydroxy-3-methylbut-2-enylamino]-9-β-D-ribofuranosylpurine

Database IDs

• CAS Number: 1009341-51-8
• PubChem SID: 164226689
• PubChem CID: 71749128

CALCULATED PROPERTIES

• Acid pKa: 12.453981
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -2.3512642
• LogD (pH = 7.4): -2.3501964
• Log P: -2.350179
• Molar Refractivity: 90.6714 cm^3
• Polarizability: 34.72466 Å^3
• Polar Surface Area: 145.78 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethanol; Methanol; Water
• Apperance: Off White Powder-Tan Coloured Cast
• Melting Point: 180-182°C

DETAILS

Toronto Research Chemicals - H946500

A well-known, highly active stimulant of cell divisions in plant tissue cultures.

REFERENCES

• D.S. Letham: Phytochemistry, 12, 2445 (1973)