N-acetyltryptophan (CHEM003375)

Record Information
Version1.0
Creation Date2014-08-29 06:51:08 UTC
Update Date2026-04-05 18:47:37 UTC
Accession NumberCHEM003375
Identification
Common NameN-acetyltryptophan
ClassSmall 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
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(S)-N-AcetyltryptophanHMDB
Ac-TrpHMDB
Acetyl-L-TrpHMDB
Acetyl-L-tryptophanHMDB
AcetyltryptophanHMDB
N-Acetyl-L-tryptophanHMDB
Tryptophan, acetylHMDB
N-AcetyltryptophanMeSH
(2S)-2-Acetamido-3-(1H-indol-3-yl)propanoic acidHMDB
(2S)-2-Acetamido-3-(1H-indol-3-yl)propionic acidHMDB
L-N-AcetyltryptophanHMDB
NATHMDB
Chemical FormulaC13H14N2O3
Average Molecular Mass246.262 g/mol
Monoisotopic Mass246.100 g/mol
CAS Registry Number1218-34-4
IUPAC Name(2S)-2-[(1-hydroxyethylidene)amino]-3-(1H-indol-3-yl)propanoic acid
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 IdentifierInChI=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 KeyDZTHIGRZJZPRDV-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Isovaleric AciduriaSMP00238 Not Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point189.5°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.49 g/LALOGPS
logP1.45ALOGPS
logP1.81ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)4.17ChemAxon
pKa (Strongest Basic)1.52ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area85.68 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity66.17 m³·mol⁻¹ChemAxon
Polarizability25.25 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0013713
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID74640
PubChem Compound ID700653
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.