(2S)-2-{[2-(2,3-dihydro-1H-inden-5-yloxy)-9-[(4-phenylphenyl)methyl]-9H-purin-6-yl]amino}-3-phenylpropan-1-ol hydrate

• ChemBase ID: 154101
• Molecular Formular: C36H35N5O3
• Molecular Mass: 585.6948
• Monoisotopic Mass: 585.27399001
• SMILES: c1ccc(cc1)C[C@@H](CO)Nc1c2c(nc(n1)Oc1ccc3c(c1)CCC3)n(cn2)Cc1ccc(cc1)c1ccccc1.O
• Canonical SMILES: OC[C@@H](Nc1nc(Oc2ccc3c(c2)CCC3)nc2c1ncn2Cc1ccc(cc1)c1ccccc1)Cc1ccccc1.O
• InChI: InChI=1S/C36H33N5O2.H2O/c42-23-31(20-25-8-3-1-4-9-25)38-34-33-35(40-36(39-34)43-32-19-18-28-12-7-13-30(28)21-32)41(24-37-33)22-26-14-16-29(17-15-26)27-10-5-2-6-11-27;/h1-6,8-11,14-19,21,24,31,42H,7,12-13,20,22-23H2,(H,38,39,40);1H2/t31-;/m0./s1
• InChIKey: FZYHXSYFDLKPQY-YNMZEGNTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[2-(2,3-dihydro-1H-inden-5-yloxy)-9-[(4-phenylphenyl)methyl]-9H-purin-6-yl]amino}-3-phenylpropan-1-ol hydrate
• IUPAC Traditional name: (2S)-2-{[2-(2,3-dihydro-1H-inden-5-yloxy)-9-[(4-phenylphenyl)methyl]purin-6-yl]amino}-3-phenylpropan-1-ol hydrate
• Synonyms: (2S)-2-[2-(Indan-5-yloxy)-9-(1,1′-biphenyl-4-yl)methyl)-9H-purin-6-ylamino]-3-phenyl-propan-1-ol hydrate; QS11 hydrate

Database IDs

• CAS Number: 944328-88-5(anhydrous)
• MDL Number: MFCD12912439
• PubChem SID: 162248240
• PubChem CID: 71311792

CALCULATED PROPERTIES

• Acid pKa: 14.787619
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 7.9356074
• LogD (pH = 7.4): 7.9356236
• Log P: 7.935624
• Molar Refractivity: 171.1363 cm^3
• Polarizability: 66.3412 Å^3
• Polar Surface Area: 85.09 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: white powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C36H33N5O2 · xH2O

DETAILS

Sigma Aldrich - Q4972

Biochem/physiol Actions
QS11 is an inhibitor of GTPase activating protein of ADP-ribosylation factor 1 (ARFGAP1), as well as a synergizer of the Wnt/β-catenin signaling pathway. The Wnt/β-catenin signaling pathway regulates cell morphology, motility, proliferation, and differentiation during development. The GTPase activating protein of ADP-ribosylation factors (ARFGAPs) regulates the small GTPase ADP-ribosylation factors (ARFs) that mediate a number of biological processes, including vesicle trafficking and cytoskeleton reorganization. QS-11 binds and inhibits GTPase activating protein of ADP-ribosylation factor1 (ARFGAP1). Inhibition of ARFGAPs increases the level of activated ARF and subsequent β-catenin translocation leading to pathway activation.