Phenylalanine
C₉H₁₁NO₂·165.192 g/mol·Amino Acids·CID 6140
Amino AcidEssentialAromatic
An essential amino acid with a benzyl side chain. Precursor to tyrosine, and through it to dopamine, norepinephrine, and melanin. People with phenylketonuria (PKU) cannot metabolize it — hence the warning on aspartame-containing products.
IUPAC: (2S)-2-amino-3-phenylpropanoic acid
Also known as: phenylalanine, 63-91-2, (S)-2-Amino-3-phenylpropanoic acid, (2S)-2-amino-3-phenylpropanoic acid, 3-Phenyl-L-alanine (+14 more)
Molecular Structure
Molecular Propertiesmass · H-bonds · stereo
Molecular Weight
165.190g/mol
Exact Mass
165.078979Da
Monoisotopic Mass
165.078979Da
XLogP
-1.5
Polar Surface Area
63.3Ų
Complexity
153
Formal Charge
0
H-Bond Donors
2
H-Bond Acceptors
3
Rotatable Bonds
3
Heavy Atoms
12
Stereo Centers
1
Bond Stereo
0
Drug-Likeness (Lipinski's Rule of Five)
✓ 165.2 g/mol
MW ≤ 500
✓ -1.5
LogP ≤ 5
✓ 2
H-bond donors ≤ 5
✓ 3
H-bond acceptors ≤ 10
Passes all rules — good oral bioavailability predicted
Chemical IdentifiersSMILES · InChI
InChI
InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m0/s1
Constituent Elements
Isomers8 compounds with formula C₉H₁₁NO₂
ethyl 4-aminobenzoate
CID 2337 · 165.2 g/mol
methyl 2-(methylamino)benzoate
CID 6826 · 165.2 g/mol
2-ethoxybenzamide
CID 3282 · 165.2 g/mol
(2R)-2-amino-3-phenylpropanoic acid
CID 71567 · 165.2 g/mol
(3-methylphenyl) N-methylcarbamate
CID 14322 · 165.2 g/mol
N-(4-methoxyphenyl)acetamide
CID 5827 · 165.2 g/mol
ethyl 2-aminobenzoate
CID 6877 · 165.2 g/mol
2-amino-3-phenylpropanoic acid
CID 994 · 165.2 g/mol