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tryptophan

File:L-Tryptophan_-_L-Tryptophan.svg · Wikimedia Commons · See Wikimedia Commons

EntityQ181003· pop 66· linked from 2,729 articles

tryptophan

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Also known as L-Trp, (-)-Tryptophan, (2S)-2-amino-3-(1H-indol-3-yl)Propanoic acid, (S)-alpha-amino-1H-indole-3-propanoic acid, (S)-alpha-Amino-beta-(3-indolyl)-propionic acid, (S)-Tryptophan, (S)-α-amino-1H-indole-3-propanoic acid, L-(-)-Tryptophan

OverviewAI-generated

Tryptophan is a chemical compound with the formula C₁₁H₁₂N₂O₂. Its IUPAC name is (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid. The molecule has a mass of 204.09 and a pKa of 9.39. It features a charge of 0, an xlogp of -1.1, and a topological polar surface area of 79.1. The compound contains three hydrogen bond donors and three hydrogen bond acceptors.

The canonical SMILES notation for tryptophan is C1=CC=C2C(=C1)C(=CN2)CC(C(=O)O)N, while its isomeric SMILES is N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O. PubChem lists its weight as 204.22. The substance is associated with the NCI Thesaurus ID C29603.

In scientific literature, tryptophan is the subject of 80,629 PubMed entries. It is also referenced by 2,729 other encyclopedia articles.

Synthesized by Vinony from 20 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Chemical data

Formula
C11H12N2O2
Molecular weight
204.22 g/mol
IUPAC name
(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
SMILES
C1=CC=C2C(=C1)C(=CN2)C[C@@H](C(=O)O)N
InChIKey
QIVBCDIJIAJPQS-VIFPVBQESA-N
XLogP
-1.1
Polar surface area
79.1 Ų
H-bond donors
3
H-bond acceptors
3
Formal charge
0

via PubChem

Research

80,629 papers

via PubMed

~16 min read

Encyclopedic overview

22 sections
Contents
  • Function
  • Recommended dietary allowance
  • Dietary sources
  • Medical use
  • Depression
  • Insomnia
  • Side effects
  • Interactions
  • Isolation
  • Biosynthesis and industrial production
  • Society and culture
  • Showa Denko contamination scandal
  • Turkey meat and drowsiness hypothesis
  • Research
  • Yeast amino acid metabolism
  • Serotonin precursor
  • Psychedelic effects
  • Fluorescence
  • See also
  • References
  • Further reading
  • External links

thumb|Tryptophan ball and stick model spinning Tryptophan (symbol Trp or W) is an α-amino acid that is used in the biosynthesis of proteins. Tryptophan contains an α-amino group, an α-carboxylic acid group, and a side chain indole, making it a polar molecule with a non-polar aromatic beta carbon substituent. Tryptophan is also a precursor to the neurotransmitter serotonin, the hormone melatonin, and vitamin B3 (niacin). It is encoded by the codon UGG.

Like other amino acids, tryptophan is a zwitterion at physiological pH where the amino group is protonated (–; pKa = 9.39) and the carboxylic acid is deprotonated (–COO−; pKa = 2.38).

Excerpted from Wikipedia’s “tryptophan” article, available under the CC BY-SA 4.0 licence.

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