(2S)-2-amino-3-phenylpropanamide

• ChemBase ID: 3656
• Molecular Formular: C9H12N2O
• Molecular Mass: 164.20438
• Monoisotopic Mass: 164.09496301
• SMILES: N[C@H](C(=O)N)Cc1ccccc1
• Canonical SMILES: N[C@H](C(=O)N)Cc1ccccc1
• InChI: InChI=1S/C9H12N2O/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H2,11,12)/t8-/m0/s1
• InChIKey: OBSIQMZKFXFYLV-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-phenylpropanamide
• IUPAC Traditional name: phenylalanine amide; @phenylalanine amide
• Synonyms: (αS)-α-Amino-benzenepropanamide; (S)-α-Amino-hydrocinnamamide; L-Phenylalaninamide; L-Phenylalanine Amide; (2S)-2-Amino-3-phenylpropionyl Amide; (S)-2-Amino-3-phenyl-propionamide; L-Phenylalaninamide; L-PHENYLALANINAMIDE; Phenylalanine Amide

Database IDs

• CAS Number: 5241-58-7
• MDL Number: MFCD00038146
• Beilstein Number: 6270941
• PubChem SID: 46507043; 24898253; 24887355; 160967094
• PubChem CID: 445694

CALCULATED PROPERTIES

JChem

• Acid pKa: 16.337788
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -2.131882
• LogD (pH = 7.4): -0.43836388
• Log P: 0.27067244
• Molar Refractivity: 46.9385 cm^3
• Polarizability: 18.586464 Å^3
• Polar Surface Area: 69.11 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.1
• LOG S: -1.77
• Solubility (Water): 2.77e+00 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Off-White Solid
• Melting Point: 93-95°C

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0% (HPLC)
• Grade: purum
• Empirical Formula (Hill Notation): C9H12N2O

DETAILS

MP Biomedicals - 05216599

MP Biomedicals Rare Chemical collection

DrugBank - DB04029

Drug information: experimental

Sigma Aldrich - P1883

Biochem/physiol Actions
L-Phenylalaninamide is a chiral selector.

Sigma Aldrich - 80314

Other Notes
Amino acid for posttranslational amidation of peptides by CPDY1

Toronto Research Chemicals - A626085

Protected amino acid

REFERENCES

• Villiers, B., et al.: ChemBioChem. 10, 671 (2009)
• Fransson, R., et al.: J. Med. Chem., 53, 2383 (2009)
• Watts, R., et al.: Biochem., 49, 2177 (2009)