2-[6-(benzylamino)-9H-purin-9-yl]-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 133959
• Molecular Formular: C18H21N5O5
• Molecular Mass: 387.38984
• Monoisotopic Mass: 387.1542688
• SMILES: c1ccc(cc1)CNc1c2c(ncn1)n(cn2)C1C(C(C(C(O1)CO)O)O)O
• Canonical SMILES: OCC1OC(C(C(C1O)O)O)n1cnc2c1ncnc2NCc1ccccc1
• InChI: InChI=1S/C18H21N5O5/c24-7-11-13(25)14(26)15(27)18(28-11)23-9-22-12-16(20-8-21-17(12)23)19-6-10-4-2-1-3-5-10/h1-5,8-9,11,13-15,18,24-27H,6-7H2,(H,19,20,21)
• InChIKey: KRUUBWXADMDQSI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[6-(benzylamino)-9H-purin-9-yl]-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: 2-[6-(benzylamino)purin-9-yl]-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: N6-Benzyladenine 9-glucoside; 6-Benzylaminopurine 9-(β-D-glucoside)

Database IDs

• CAS Number: 4294-17-1
• MDL Number: MFCD00189345
• PubChem SID: 24892052; 162228236
• PubChem CID: 4686241

CALCULATED PROPERTIES

• Acid pKa: 12.357906
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -0.7803244
• LogD (pH = 7.4): -0.69631255
• Log P: -0.6951216
• Molar Refractivity: 99.2641 cm^3
• Polarizability: 38.351044 Å^3
• Polar Surface Area: 145.78 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - B8148

General description
Major metabolite of the cytokinin, 6-benzylaminopurine (BAP).1