ContaminantDB: N-acetyltryptophan

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:51:08 UTC

Update Date

2026-04-05 18:47:37 UTC

Accession Number

CHEM003375

Identification

Common Name

N-acetyltryptophan

Class

Small Molecule

Description

N-acetyltryptophan has been used as a protein stabolizer. It prevents protein molecules from oxidative degradation by scavenging oxygen dissolved in protein solutions. (1).

Contaminant Sources

HMDB Contaminants - Urine
T3DB toxins

Contaminant Type

Amine
Animal Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-N-Acetyltryptophan	HMDB
Ac-Trp	HMDB
Acetyl-L-Trp	HMDB
Acetyl-L-tryptophan	HMDB
Acetyltryptophan	HMDB
N-Acetyl-L-tryptophan	HMDB
Tryptophan, acetyl	HMDB
N-Acetyltryptophan	MeSH
(2S)-2-Acetamido-3-(1H-indol-3-yl)propanoic acid	HMDB
(2S)-2-Acetamido-3-(1H-indol-3-yl)propionic acid	HMDB
L-N-Acetyltryptophan	HMDB
NAT	HMDB

Chemical Formula

C₁₃H₁₄N₂O₃

Average Molecular Mass

246.262 g/mol

Monoisotopic Mass

246.100 g/mol

CAS Registry Number

1218-34-4

IUPAC Name

Not Available

Traditional Name

(2S)-2-[(1-hydroxyethylidene)amino]-3-(1H-indol-3-yl)propanoic acid

SMILES

[H][C@@](CC1=CNC2=CC=CC=C12)(N=C(C)O)C(O)=O

InChI Identifier

InChI=1S/C13H14N2O3/c1-8(16)15-12(13(17)18)6-9-7-14-11-5-3-2-4-10(9)11/h2-5,7,12,14H,6H2,1H3,(H,15,16)(H,17,18)/t12-/m0/s1

InChI Key

DZTHIGRZJZPRDV-LBPRGKRZSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-L-alpha-amino acids

Alternative Parents

Substituents

N-acyl-l-alpha-amino acid
Indolyl carboxylic acid derivative
3-alkylindole
Indole
Indole or derivatives
Substituted pyrrole
Benzenoid
Acetamide
Heteroaromatic compound
Pyrrole
Carboxamide group
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

N-acetyl-L-amino acid (CHEBI:74640 )
L-tryptophan derivative (CHEBI:74640 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Isovaleric Aciduria	SMP00238	Not Available

Applications

Not Available

Biological Roles

metabolite

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	189.5°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.49 g/L	ALOGPS
logP	1.45	ALOGPS
logP	1.81	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	4.17	ChemAxon
pKa (Strongest Basic)	1.52	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	85.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	66.17 m³·mol⁻¹	ChemAxon
Polarizability	25.25 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0udi-0390000000-bf959d5e1aab8cd794f3	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0udi-1490000000-855cbd5624936bf3e2a1	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udi-0390000000-bf959d5e1aab8cd794f3	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udi-1490000000-855cbd5624936bf3e2a1	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9550000000-f9186fd00d73708a5b17	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00fr-9134000000-6e66aca41e26bf891fac	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-05o4-0900000000-281ce0ad760f7fc94b1c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0159-0900000000-ce991768eab82fbdbf84	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0603-9300000000-d07cb4937723d06edd48	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0600-9300000000-2c409c01a91d64e800d7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0f6t-3190000000-1203a50dbf1ce05d0ee5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9320000000-37f28cef4c5fd836b4f2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0pc9-0910000000-01c22859bbaf5182beff	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-0002-0790000000-5c560e793d549bcec815	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00l6-3900000000-9fecaf5dedd815d7ac9b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-0002-0690000000-87ef1c3dfb4287e7ad08	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4s-0900000000-e88cf6e618c54b9a2d65	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0k9i-0940000000-5ab9f2966f1604b51cb3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0pc9-0920000000-204470b43912cb6712bc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00lu-0900000000-b1fa15ca34966d5c3ebc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f6t-0390000000-bee3f00676dbb20cddc3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pb9-0960000000-ffc38c580062532632f8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0900000000-5e314622f2cf80867542	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-1290000000-2f09bb4277a17573a1d4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfs-6890000000-cf484d59c551e83dba23	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05mo-9500000000-49f44fec5a91f601a9b4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0fr2-2790000000-64600864aeea894a8f16	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01b9-9600000000-fee48c2c347edd3e362e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-7900000000-baeeeec89ae0148886b5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-054t-0390000000-e119f5a3710d3fba6328	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4u-0910000000-7fc91bffadf6c81532dc	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0013713

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

74640

PubChem Compound ID

700653

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=3141295

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=6538443

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=7229743

4. Fang L, Parti R, Hu P: Characterization of N-acetyltryptophan degradation products in concentrated human serum albumin solutions and development of an automated high performance liquid chromatography-mass spectrometry method for their quantitation. J Chromatogr A. 2011 Oct 14;1218(41):7316-24. doi: 10.1016/j.chroma.2011.08.044. Epub 2011 Aug 18.

N-acetyltryptophan (CHEM003375)

Structure for CHEM003375: N-acetyltryptophan