(2R,3S,4R,5R)-2-(hydroxymethyl)-5-{6-[(3-methylbut-2-en-1-yl)amino]-9H-purin-9-yl}oxolane-3,4-diol

• ChemBase ID: 105928
• Molecular Formular: C15H21N5O4
• Molecular Mass: 335.35834
• Monoisotopic Mass: 335.15935418
• SMILES: n1c2c(ncnc2NCC=C(C)C)n(c1)[C@@H]1O[C@@H]([C@@H](O)[C@H]1O)CO
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2NCC=C(C)C
• InChI: InChI=1S/C15H21N5O4/c1-8(2)3-4-16-13-10-14(18-6-17-13)20(7-19-10)15-12(23)11(22)9(5-21)24-15/h3,6-7,9,11-12,15,21-23H,4-5H2,1-2H3,(H,16,17,18)/t9-,11-,12-,15-/m1/s1
• InChIKey: USVMJSALORZVDV-SDBHATRESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4R,5R)-2-(hydroxymethyl)-5-{6-[(3-methylbut-2-en-1-yl)amino]-9H-purin-9-yl}oxolane-3,4-diol
• IUPAC Traditional name: isopentenyladenosine
• Synonyms: 2iP Riboside; 6-(3,3-Dimethylallylamino)purine riboside; N6-(γ,γ-Dimethylallyl)adenosine; N6-(2-Isopentenyl)adenosine; N^6-(Δ^2-Isopentenyl)adenosine; 6-(γ,γ-DIMETHYLALLYLAMINO) PURINE RIBOSIDE; 6-(γ,γ-Dimethylallylamino)purine riboside; 6-(3,3-二甲基烯丙基氨基)嘌呤核苷; N6-(γ,γ-二甲基烯丙基)腺苷; N6-(2-异戊烯基)腺苷; 利波腺苷; 6-(γ,γ-二甲基烯丙基氨基)嘌呤核苷

Database IDs

• CAS Number: 7724-76-7; 33156-15-9
• EC Number: 231-771-3
• MDL Number: MFCD00005741
• PubChem SID: 24894095; 162092682
• PubChem CID: 24405

CALCULATED PROPERTIES

• Acid pKa: 12.45397
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.513864
• LogD (pH = 7.4): -0.4292136
• Log P: -0.4280137
• Molar Refractivity: 87.8072 cm^3
• Polarizability: 33.413445 Å^3
• Polar Surface Area: 125.55 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: 0°C
• RTECS: AU7404910
• 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: 98%
• Empirical Formula (Hill Notation): C15H21N5O4

DETAILS

MP Biomedicals - 02195143

Crystalline
A cytokinin, natural component of certain tRNA's, possessing antitumor and immunosuppressant activity.

Sigma Aldrich - D7036

Linkage
Similar to D 7257, but produced by Sigma.

REFERENCES

• Plant Physiol. , 50 : 616 (1972).
• Biochim. Biophys. Acta , 281 : 488 (1972).