(2S)-2-{[(2S)-2-[(2S)-2-{[(2S)-2-{[(tert-butoxy)carbonyl]amino}propanoyl]oxy}-3-methylbutanamido]propanoyl]oxy}-3-methylbutanoic acid hydrate

• ChemBase ID: 155025
• Molecular Formular: C21H38N2O10
• Molecular Mass: 478.53382
• Monoisotopic Mass: 478.25264543
• SMILES: C[C@@H](C(=O)O[C@@H](C(C)C)C(=O)O)NC(=O)[C@H](C(C)C)OC(=O)[C@H](C)NC(=O)OC(C)(C)C.O
• Canonical SMILES: O=C(OC(C)(C)C)N[C@H](C(=O)O[C@H](C(=O)N[C@H](C(=O)O[C@H](C(=O)O)C(C)C)C)C(C)C)C.O
• InChI: InChI=1S/C21H36N2O9.H2O/c1-10(2)14(30-19(28)13(6)23-20(29)32-21(7,8)9)16(24)22-12(5)18(27)31-15(11(3)4)17(25)26;/h10-15H,1-9H3,(H,22,24)(H,23,29)(H,25,26);1H2/t12-,13-,14-,15-;/m0./s1
• InChIKey: CARNRIDSPYICIM-WFGXUCIJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S)-2-[(2S)-2-{[(2S)-2-{[(tert-butoxy)carbonyl]amino}propanoyl]oxy}-3-methylbutanamido]propanoyl]oxy}-3-methylbutanoic acid hydrate
• IUPAC Traditional name: (2S)-2-{[(2S)-2-[(2S)-2-{[(2S)-2-[(tert-butoxycarbonyl)amino]propanoyl]oxy}-3-methylbutanamido]propanoyl]oxy}-3-methylbutanoic acid hydrate
• Synonyms: N-[(1,1-Dimethylethoxy)carbonyl]-L-alanyl-(2S)-2-hydroxy-3-methylbutanoyl-L-Alanine-(1S)-1-carboxy-2-methylpropyl ester hydrate; N-[(1,1-Dimethylethoxy)carbonyl]-L-alanyl-(2S)-2-hydroxy-3-methylbutanoyl-L-alanyl-(2S)-2-hydroxy-3-methylbutanoic acid hydrate; NSC 668036 hydrate

Database IDs

• CAS Number: 144678-63-7(anhydrous)
• MDL Number: MFCD20036264
• PubChem SID: 162249163
• PubChem CID: 71312059

CALCULATED PROPERTIES

• Acid pKa: 3.5283198
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.5727084
• LogD (pH = 7.4): -0.8296067
• Log P: 2.5371408
• Molar Refractivity: 111.3541 cm^3
• Polarizability: 44.7746 Å^3
• Polar Surface Area: 157.33 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: ≥5 mg/mL
• Apperance: white to tan powder

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C21H36N2O9 · xH2O

DETAILS

Sigma Aldrich - SML0046

Biochem/physiol Actions
NSC 668036 binds to the PDZ domain of the Wnt-pathway signaling molecule Disheveled (Dvl), blocking the binding and activation of Dvl by Frizzled. In Xenopus embryos, NSC 668036 inhibited Wnt3A-induced expression of the target gene Siamois and formation of secondary axes.