(4aR,6S,7R,7aS)-6-(4-{[(1S)-2,3-dihydro-1H-inden-1-yl]amino}-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(4-methoxyphenyl)-hexahydro-2H-cyclopenta[d][1,3]dioxin-7-ol

• ChemBase ID: 167738
• Molecular Formular: C29H30N4O4
• Molecular Mass: 498.5729
• Monoisotopic Mass: 498.22670546
• SMILES: n1cnc2c(c1N[C@@H]1c3c(CC1)cccc3)ccn2[C@@H]1[C@H]([C@@H]2[C@H](C1)COC(O2)c1ccc(cc1)OC)O
• Canonical SMILES: COc1ccc(cc1)C1OC[C@@H]2[C@H](O1)[C@H](O)[C@H](C2)n1ccc2c1ncnc2N[C@H]1CCc2c1cccc2
• InChI: InChI=1S/C29H30N4O4/c1-35-20-9-6-18(7-10-20)29-36-15-19-14-24(25(34)26(19)37-29)33-13-12-22-27(30-16-31-28(22)33)32-23-11-8-17-4-2-3-5-21(17)23/h2-7,9-10,12-13,16,19,23-26,29,34H,8,11,14-15H2,1H3,(H,30,31,32)/t19-,23+,24+,25-,26+,29?/m1/s1
• InChIKey: MPHAQTOCAUGHAB-VFIKIOMUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4aR,6S,7R,7aS)-6-(4-{[(1S)-2,3-dihydro-1H-inden-1-yl]amino}-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(4-methoxyphenyl)-hexahydro-2H-cyclopenta[d][1,3]dioxin-7-ol
• IUPAC Traditional name: (4aR,6S,7R,7aS)-6-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]pyrrolo[2,3-d]pyrimidin-7-yl}-2-(4-methoxyphenyl)-hexahydro-2H-cyclopenta[d][1,3]dioxin-7-ol
• Synonyms: (4aS,6R,7S,7aR)-6-[4-[[(1S)-2,3-Dihydro-1H-inden-1-yl]amino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl]hexahydro-2-(4-methoxyphenyl)-cyclopenta-1,3-dioxin-7-ol

Database IDs

• CAS Number: 905580-87-2
• PubChem SID: 162261871
• PubChem CID: 71316207

CALCULATED PROPERTIES

• Acid pKa: 13.503391
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 2.7701836
• LogD (pH = 7.4): 4.0698524
• Log P: 4.2577224
• Molar Refractivity: 140.1433 cm^3
• Polarizability: 53.989548 Å^3
• Polar Surface Area: 90.66 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Off-white Foam

DETAILS

Toronto Research Chemicals - D449890

Used in the preparation of nucleoside derivatives as antitumor agents, E1 activating enzymes and MLN4924, an inhibitor of NEDD8-activating enzyme.

REFERENCES

• Soucy, T. et al.; Nature 458, 732 (2009)