3-{1-[(benzyloxy)carbonyl]-5-methyl-1H-indol-3-yl}-2-[(2-phenoxyphenyl)formamido]propanoic acid

• ChemBase ID: 153146
• Molecular Formular: C33H28N2O6
• Molecular Mass: 548.58522
• Monoisotopic Mass: 548.19473663
• SMILES: Cc1ccc2c(c1)c(cn2C(=O)OCc1ccccc1)CC(C(=O)O)NC(=O)c1ccccc1Oc1ccccc1
• Canonical SMILES: Cc1ccc2c(c1)c(CC(C(=O)O)NC(=O)c1ccccc1Oc1ccccc1)cn2C(=O)OCc1ccccc1
• InChI: InChI=1S/C33H28N2O6/c1-22-16-17-29-27(18-22)24(20-35(29)33(39)40-21-23-10-4-2-5-11-23)19-28(32(37)38)34-31(36)26-14-8-9-15-30(26)41-25-12-6-3-7-13-25/h2-18,20,28H,19,21H2,1H3,(H,34,36)(H,37,38)
• InChIKey: FHNQOOZTZWBWQO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{1-[(benzyloxy)carbonyl]-5-methyl-1H-indol-3-yl}-2-[(2-phenoxyphenyl)formamido]propanoic acid
• IUPAC Traditional name: 3-{1-[(benzyloxy)carbonyl]-5-methylindol-3-yl}-2-[(2-phenoxyphenyl)formamido]propanoic acid
• Synonyms: 5-Methyl-N-(2-phenoxybenzoyl)-1-[(phenylmethoxy)carbonyl]-D/L-tryptophan; R5C3

Database IDs

• CAS Number: 753504-14-2
• MDL Number: MFCD08705330
• PubChem SID: 162247286; 24724593
• PubChem CID: 16079003

CALCULATED PROPERTIES

• Acid pKa: 3.4001276
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.439225
• LogD (pH = 7.4): 3.1237957
• Log P: 6.52668
• Molar Refractivity: 153.1056 cm^3
• Polarizability: 60.10214 Å^3
• Polar Surface Area: 106.86 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble18 mg/mL
• Apperance: solid

Safety Information

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

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C33H28N2O6

DETAILS

Sigma Aldrich - R7529

Biochem/physiol Actions
R5C3 is an MDM2 inhibitor, 2-phenoxybenzoyl-tryptophan derivative. Reported as a novel probe for high throughput fluorescence polarization binding assay. Useful in drug screening for small molecule inhibitors of MDM2-binding to p53.