[3,5-bis(trifluoromethyl)phenyl]methyl (2S)-2-acetamido-3-(1H-indol-3-yl)propanoate

• ChemBase ID: 133947
• Molecular Formular: C22H18F6N2O3
• Molecular Mass: 472.3803392
• Monoisotopic Mass: 472.12216177
• SMILES: CC(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)OCc1cc(cc(c1)C(F)(F)F)C(F)(F)F
• Canonical SMILES: CC(=O)N[C@H](C(=O)OCc1cc(cc(c1)C(F)(F)F)C(F)(F)F)Cc1c[nH]c2c1cccc2
• InChI: InChI=1S/C22H18F6N2O3/c1-12(31)30-19(8-14-10-29-18-5-3-2-4-17(14)18)20(32)33-11-13-6-15(21(23,24)25)9-16(7-13)22(26,27)28/h2-7,9-10,19,29H,8,11H2,1H3,(H,30,31)/t19-/m0/s1
• InChIKey: BYYQYXVAWXAYQC-IBGZPJMESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [3,5-bis(trifluoromethyl)phenyl]methyl (2S)-2-acetamido-3-(1H-indol-3-yl)propanoate
• IUPAC Traditional name: [3,5-bis(trifluoromethyl)phenyl]methyl (2S)-2-acetamido-3-(1H-indol-3-yl)propanoate
• Synonyms: L-732,138; N-Acetyl-L-tryptophan 3,5-bis(trifluoromethyl)benzyl ester

Database IDs

• CAS Number: 148451-96-1
• MDL Number: MFCD00237267
• PubChem SID: 162228224; 24277690
• PubChem CID: 132837

CALCULATED PROPERTIES

• Acid pKa: 9.740959
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 4.6212654
• LogD (pH = 7.4): 4.6195374
• Log P: 4.621288
• Molar Refractivity: 106.9757 cm^3
• Polarizability: 40.412037 Å^3
• Polar Surface Area: 71.19 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: powder
• Melting Point: 147-148 °C(lit.)

Safety Information

• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... TACR1(6869)

Product Information

• Purity: ≥99% (TLC)

DETAILS

Sigma Aldrich - A5330

Biochem/physiol Actions
Competitive substance P receptor antagonist. It is approximately 1000-fold more potent at cloned human NK-1 receptors than at cloned human NK-2 and NK-3 receptors; and approximately 200-fold more potent at human NK-1 receptors than at rat NK-1 receptors. The IC50 for the human NK-1 receptor expressed in CHO cells is approximately 2 nM.