Tryptophan (abbreviated as Trp or W; encoded by the codon UGG) is an ɑ-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated –+NH3 form under biological conditions), an α-carboxylic acid group (which is in the deprotonated –COO- form under biological conditions), and a side chain indole, classifying it as a non-polar, aromatic amino acid. It is essential in humans, meaning the body cannot synthesize it and thus it must be obtained from the diet.
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IUPAC name
Tryptophan or (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
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Other names
2-Amino-3-(1H-indol-3-yl)propanoic acid
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CAS Number
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73-22-3 |
ChEBI | CHEBI:27897 |
ChEMBL | ChEMBL54976 |
ChemSpider | 6066 |
DrugBank | DB00150 |
IUPHAR/BPS
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717 |
Jmol interactive 3D | Image |
KEGG | D00020 |
PubChem | 6305 |
UNII | 8DUH1N11BX |
InChI[show]
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SMILES[show]
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Chemical formula
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C11H12N2O2 |
Molar mass | 204.23 g·mol−1 |
Solubility in water
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Soluble: 0.23 g/L at 0 °C,
11.4 g/L at 25 °C, |
Solubility | Soluble in hot alcohol, alkali hydroxides; insoluble in chloroform. |
Acidity (pKa) | 2.38 (carboxyl), 9.39 (amino)[1] |
ATC code | N06AX02 |
Structure and
properties |
Refractive index (n), Dielectric constant (εr), etc. |
Thermodynamic
data |
Phase behaviour solid–liquid–gas |
Spectral data
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UV, IR, NMR, MS |