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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-05-18 14:04:03 UTC
Update Date2020-02-26 21:39:04 UTC
HMDB IDHMDB0013713
Secondary Accession Numbers
  • HMDB13713
Metabolite Identification
Common NameN-Acetyltryptophan
DescriptionN-Acetyltryptophan, also known as acetyl-L-Trp or NAT, belongs to the class of organic compounds known as N-acyl-L-alpha-amino acids. These are N-acylated alpha-amino acids that have the L-configuration of the alpha-carbon atom. N-Acetyltryptophan has been used as a protein stabilizer. It prevents protein molecules from oxidative degradation by scavenging oxygen dissolved in protein solutions (PMID: 21903216 ). N-Acetyltryptophan is a catabolite of tryptophan converted by the gut microbiota. After absorption through the intestinal epithelium, tryptophan catabolites enter the bloodstream and are later excreted in the urine (PMID: 28916042 ).
Structure
Data?1582753144
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 Weight246.2619
Monoisotopic Molecular Weight246.100442324
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
CAS Registry Number1218-34-4
SMILES
CC(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)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 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
Ontology
Disposition

Biological location:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point189.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0udi-0390000000-bf959d5e1aab8cd794f3Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-1490000000-855cbd5624936bf3e2a1Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-0390000000-bf959d5e1aab8cd794f3Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-1490000000-855cbd5624936bf3e2a1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9550000000-f9186fd00d73708a5b17Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00fr-9134000000-6e66aca41e26bf891facSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f6t-0390000000-bee3f00676dbb20cddc3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-0960000000-ffc38c580062532632f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900000000-5e314622f2cf80867542Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1290000000-2f09bb4277a17573a1d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfs-6890000000-cf484d59c551e83dba23Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mo-9500000000-49f44fec5a91f601a9b4Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Not AvailableMaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified1.291 umol/mmol creatinineAdult (>18 years old)Female
Pregnancy
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound700653
PDB IDNot Available
ChEBI ID74640
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:21903216 ]
  2. Pavlova T, Vidova V, Bienertova-Vasku J, Janku P, Almasi M, Klanova J, Spacil Z: Urinary intermediates of tryptophan as indicators of the gut microbial metabolism. Anal Chim Acta. 2017 Sep 22;987:72-80. doi: 10.1016/j.aca.2017.08.022. Epub 2017 Aug 26. [PubMed:28916042 ]