Formula of the 20 common amino acids

The formula of an amino acid comprises, bound to a carbon (alpha carbon):

o a carboxyl group -COOH

o an amine group -NH2
o an atom of hydrogen -H
o a variable radical -R, that is the functional group (in red in the table) of the amino acid.

Chemically speaking, an amino acid is a carboxylic acid which has an amine group attached to it. The general linear
formula of an amino acid is R-CH(NH2)-COOH.

The 20 common amino acids are grouped in classes according to their side chains:

Click here for IMGT classes of the 20 common amino acids 'Physicochemical' properties.

Structural formula

Amino acids with uncharged side chains

POLAR SIDE CHAINS NON POLAR SIDE CHAINS

SERINE GLYCINE

THREONINE ALANINE

TYROSINE CYSTEINE (1)

ASPARAGINE VALINE
 GLUTAMINE LEUCINE

ISOLEUCINE

PROLINE

METHIONINE

PHENYLALANINE

TRYPTOPHAN

Amino acids with charged side chains

Charged side chains are POLAR.

ACIDIC SIDE CHAINS BASIC SIDE CHAINS

ASPARTIC
LYSINE
ACID
 GLUTAMIC
ARGININE
ACID

HISTIDINE

1. (1)
 Paired cysteines allow disulfide bonds to form in proteins: -CH2-S-S-CH2-

Molecular and linear formulas

Amino acid Abbreviations Molecular formula Linear formula

Alanine Ala A C3H7NO2 CH3-CH(NH2)-COOH

Arginine Arg R C6H14N4O2 HN=C(NH2)-NH-(CH2)3-CH(NH2)-COOH

Asparagine Asn N C4H8N2O3 H2N-CO-CH2-CH(NH2)-COOH

Aspartic acid Asp D C4H7NO4 HOOC-CH2-CH(NH2)-COOH

Cysteine Cys C C3H7NO2S HS-CH2-CH(NH2)-COOH

Glutamine Gln Q C5H10N2O3 H2N-CO-(CH2)2-CH(NH2)-COOH

Glutamic acid Glu E C5H9NO4 HOOC-(CH2)2-CH(NH2)-COOH

Glycine Gly G C2H5NO2 NH2-CH2-COOH

Histidine His H C6H9N3O2 NH-CH=N-CH=C-CH2-CH(NH2)-COOH

Isoleucine Ile I C6H13NO2 CH3-CH2-CH(CH3)-CH(NH2)-COOH

Leucine Leu L C6H13NO2 (CH3)2-CH-CH2-CH(NH2)-COOH

Lysine Lys K C6H14N2O2 H2N-(CH2)4-CH(NH2)-COOH

 Methionine Met M C5H11NO2S CH3-S-(CH2)2-CH(NH2)-COOH

Phenylalanin
Phe F C9H11NO2 Ph-CH2-CH(NH2)-COOH
e

Proline Pro P C5H9NO2 NH-(CH2)3-CH-COOH

Serine Ser S C3H7NO3 HO-CH2-CH(NH2)-COOH

Threonine Thr T C4H9NO3 CH3-CH(OH)-CH(NH2)-COOH

Tryptophan Trp W C11H12N2O2 Ph-NH-CH=C-CH2-CH(NH2)-COOH

Tyrosine Tyr Y C9H11NO3 HO-Ph-CH2-CH(NH2)-COOH

Valine Val V C5H11NO2 (CH3)2-CH-CH(NH2)-COOH

Structural details of the side chains: formula, 3D model and atoms

nomenclature
The general formula of an amino acid is composed by a carbon alpha atom, a carboxyl group, a side chain group and
an amino group.

o Molecular formula: structural formula with the carbon alpha atom and the radical of each amino acid.
o 3D molecular model: a ball and stick model of the amino acids is shown. Oxygen, hydrogen, nitrogen and
sulfur atoms are represented by colored spheres (Oxygen: red, Hydrogen: white, Nitrogen: blue, Sulfur:
yellow). The carbon alpha atom is represented by black sticks and other carbons by grey sticks.
o Atoms nomenclature:

 CA : Carbon alpha
 HB : Hydrogen of carbon beta
 HN : Hydrogen of nitrogen
 OXT : Oxygen of hydroxyl
 HXT : Hydrogen of hydroxyl
 o Representation of an amino acid example (cystein) engaged in a peptide chain and showing the carbone
alpha and the carbone beta.

AMINO MOLECULAR
3D MOLECULAR MODEL ATOMS NOMENCLATURE
ACID FORMULA

ALANINE

ARGININE
ASPARAGI
NE

ASPARTIC
ACID

CYSTEINE
GLUTAMIN
E

GLUTAMIC
ACID

GLYCINE

HISTIDINE
ISOLEUCIN
E

LEUCINE

LYSINE
METHIONIN
E

PHENYLAL
ANINE

PROLINE

SERINE
THREONIN
E

TRYPTOPH
AN

TYROSINE
VALINE