(2E)-2-methyl-4-[(7H-purin-6-yl)amino](2-13C,4,4-2H2)but-2-en-1-ol

• ChemBase ID: 179636
• Molecular Formular: C10H13N5O
• Molecular Mass: 220.23577484
• Monoisotopic Mass: 220.1153649
• SMILES: n1cnc2c(c1NC/C=[13C](/CO)\C)[nH]cn2
• Canonical SMILES: OC/[13C](=C/CNc1ncnc2c1[nH]cn2)/C
• InChI: InChI=1S/C10H13N5O/c1-7(4-16)2-3-11-9-8-10(13-5-12-8)15-6-14-9/h2,5-6,16H,3-4H2,1H3,(H2,11,12,13,14,15)/b7-2+/i7+1
• InChIKey: UZKQTCBAMSWPJD-XNNRWQJPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-2-methyl-4-[(7H-purin-6-yl)amino](2-^1^3C,4,4-^2H₂)but-2-en-1-ol
• IUPAC Traditional name: (2E)-2-methyl-4-(7H-purin-6-ylamino)(2-^1^3C,4,4-^2H₂)but-2-en-1-ol
• Synonyms: 2E)-2-Methyl-4-(9H-purin-6-ylamino)-2-buten-1-ol-13C,d2; 6-(4-Hydroxy-3-methyl-trans-2-butenylamino)purine-13C,d2; N6-(4-Hydroxy-3-methyl-trans-2-butenyl)adenine-13C,d2; ZT-13C,d2; ZTA-13C,d2; Zeatin-13C,d2; (E)-Zeatin-13C,d2; Zeatine-13C,d2; trans-Zeatin-13C,d2

Database IDs

• PubChem SID: 164235546
• PubChem CID: 71753019

CALCULATED PROPERTIES

• Acid pKa: 10.212545
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.35780478
• LogD (pH = 7.4): -0.194451
• Log P: -0.19129121
• Molar Refractivity: 64.6058 cm^3
• Polarizability: 22.938023 Å^3
• Polar Surface Area: 86.72 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - Z273002

Labelled Zeatin. It is purified from Zea mays, is a member of the cytokinin group of plant growth factors, the activity of which is attributed to its more stable trans form. Trans-Zeatin inhibits UVB-induced matrix metalloproteinase-1 expression via MAP k

REFERENCES

• Murashige, T., et al.: Physiol. Plant, 15, 473 (1962)
• Brenneisen, P., et al.: J. Biol. Chem., 273, 5279 (1962)
• Choi, M., et al.: J. Dermatol. Sci., 46, 127 (1962)
• Bae, J., et al.: Food Chem. Toxicol., 46, 1298 (1962)