N-Acetyl-L-tyrosine (CHEM018707)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:28:05 UTC
Update Date2016-10-28 10:01:37 UTC
Accession NumberCHEM018707
Identification
Common NameN-Acetyl-L-tyrosine
ClassSmall Molecule
DescriptionAn N-acetyltyrosine in which the chiral centre has L configuration.
Contaminant Sources
  • Cosmetic Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
N-Acetyl-4-hydroxyphenylalanineChEBI
N-AcetyltyrosineChEBI
(2S)-2-Acetylamino-3-(4-hydroxyphenyl)propanoateHMDB
(2S)-2-Acetylamino-3-(4-hydroxyphenyl)propanoic acidHMDB
L-N-Acetyl-tyrosineHMDB
L-N-AcetyltyrosineHMDB
N-Acetyl-tyrosineHMDB
N-Acetyltyrosine, (DL)-isomerHMDB
Acetyl-L-tyrosineHMDB
N-Acetyltyrosine, (D)-isomerHMDB
Chemical FormulaC11H13NO4
Average Molecular Mass223.225 g/mol
Monoisotopic Mass223.084 g/mol
CAS Registry Number537-55-3
IUPAC Name(2S)-2-acetamido-3-(4-hydroxyphenyl)propanoic acid
Traditional Nameacetyl-L-tyrosine
SMILESCC(=O)N[C@@H](CC1=CC=C(O)C=C1)C(O)=O
InChI IdentifierInChI=1S/C11H13NO4/c1-7(13)12-10(11(15)16)6-8-2-4-9(14)5-3-8/h2-5,10,14H,6H2,1H3,(H,12,13)(H,15,16)/t10-/m0/s1
InChI KeyCAHKINHBCWCHCF-JTQLQIEISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentTyrosine and derivatives
Alternative Parents
Substituents
  • Tyrosine or derivatives
  • Phenylalanine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • 3-phenylpropanoic-acid
  • Amphetamine or derivatives
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.51 g/LALOGPS
logP1.03ALOGPS
logP0.59ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.67ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity56.54 m³·mol⁻¹ChemAxon
Polarizability22.25 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-02t9-1790000000-9484167b29dc57768b67Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-004i-1921000000-91d4d68bb345a8a8a747Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-02t9-1790000000-9484167b29dc57768b67Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-1921000000-91d4d68bb345a8a8a747Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9810000000-1b2e358b53063de15d83Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0uml-9574000000-9aeba0b3dc5069db4126Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0059-0900000000-1a298550f3c63022066cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-1900000000-489314daf5773f9fa91eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9300000000-3a02844e3f23883a2818Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-1900000000-c90d231f8d22d9f26ddcSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-ccea38bdb004d86be263Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000l-2900000000-318d79dc731f181122e3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-9500000000-5884fdc7247228527651Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00kr-5900000000-9612848117c7c187b999Spectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-0072-8940000000-b6f543bf9466f5d0a83fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-9300000000-b45eebbf975e26ab166bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-00dr-1940000000-33b69b7977f9d9af1050Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a4i-9600000000-a990ee67ce972fd9112eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a59-6900000000-faa99ebaf3b7d2305237Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9300000000-0995fa9131d49c7c9568Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00ko-6900000000-2dc778488fd30e78d38aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0089-2940000000-9ba200b376edff696810Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-28b05f6697d1910b23f9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9200000000-9bcdc6b13b9c4ec88928Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-7301664a6d8d33145cdfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05gi-0960000000-521b33c688de6d5af3c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0540-0910000000-11b06e8237181862ad09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4900000000-0ed4f6b83b0e699609daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1690000000-1c3495d31ad780bf247cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05ir-4920000000-04fd94657e89950888efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9400000000-a5cd6e5756fee449095eSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB11102
HMDB IDHMDB0000866
FooDB IDFDB022288
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkN-Acetyl-L-tyrosine
Chemspider ID61606
ChEBI ID21563
PubChem Compound ID68310
Kegg Compound IDC01657
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11020336
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11440179
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=1445836
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15777090
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21210840
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21365350
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21793504
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23000314
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=3931451
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=6803462
12. Liu, Aifu. Preparation of N-acetyl-L-tyrosine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 5 pp.
13. Rao NR, Bhat PG, Pattabiraman TN: Estimation of serum alpha 2-macroglobulin based on the esterolytic activity of bound alpha-chymotrypsin. Biochem Med. 1984 Dec;32(3):357-63.
14. Hoffer LJ, Sher K, Saboohi F, Bernier P, MacNamara EM, Rinzler D: N-acetyl-L-tyrosine as a tyrosine source in adult parenteral nutrition. JPEN J Parenter Enteral Nutr. 2003 Nov-Dec;27(6):419-22.
15. Dietze EC, Grillo MP, Kalhorn T, Nieslanik BS, Jochheim CM, Atkins WM: Thiol ester hydrolysis catalyzed by glutathione S-transferase A1-1. Biochemistry. 1998 Oct 20;37(42):14948-57.
16. Druml W, Hubl W, Roth E, Lochs H: Utilization of tyrosine-containing dipeptides and N-acetyl-tyrosine in hepatic failure. Hepatology. 1995 Apr;21(4):923-8.
17. Van Goudoever JB, Sulkers EJ, Timmerman M, Huijmans JG, Langer K, Carnielli VP, Sauer PJ: Amino acid solutions for premature neonates during the first week of life: the role of N-acetyl-L-cysteine and N-acetyl-L-tyrosine. JPEN J Parenter Enteral Nutr. 1994 Sep-Oct;18(5):404-8.
18. Drabik G, Naskalski JW: Chlorination of N-acetyltyrosine with HOCl, chloramines, and myeloperoxidase-hydrogen peroxide-chloride system. Acta Biochim Pol. 2001;48(1):271-5.
19. Fu S, Wang H, Davies M, Dean R: Reactions of hypochlorous acid with tyrosine and peptidyl-tyrosyl residues give dichlorinated and aldehydic products in addition to 3-chlorotyrosine. J Biol Chem. 2000 Apr 14;275(15):10851-8.
20. Sass JO, Mohr V, Olbrich H, Engelke U, Horvath J, Fliegauf M, Loges NT, Schweitzer-Krantz S, Moebus R, Weiler P, Kispert A, Superti-Furga A, Wevers RA, Omran H: Mutations in ACY1, the gene encoding aminoacylase 1, cause a novel inborn error of metabolism. Am J Hum Genet. 2006 Mar;78(3):401-9. Epub 2006 Jan 18.
21. Van Damme P, Hole K, Pimenta-Marques A, Helsens K, Vandekerckhove J, Martinho RG, Gevaert K, Arnesen T: NatF contributes to an evolutionary shift in protein N-terminal acetylation and is important for normal chromosome segregation. PLoS Genet. 2011 Jul;7(7):e1002169. doi: 10.1371/journal.pgen.1002169. Epub 2011 Jul 7.
22. Ree R, Varland S, Arnesen T: Spotlight on protein N-terminal acetylation. Exp Mol Med. 2018 Jul 27;50(7):1-13. doi: 10.1038/s12276-018-0116-z.
23. Tanaka H, Sirich TL, Plummer NS, Weaver DS, Meyer TW: An Enlarged Profile of Uremic Solutes. PLoS One. 2015 Aug 28;10(8):e0135657. doi: 10.1371/journal.pone.0135657. eCollection 2015.
24. Toyohara T, Akiyama Y, Suzuki T, Takeuchi Y, Mishima E, Tanemoto M, Momose A, Toki N, Sato H, Nakayama M, Hozawa A, Tsuji I, Ito S, Soga T, Abe T: Metabolomic profiling of uremic solutes in CKD patients. Hypertens Res. 2010 Sep;33(9):944-52. doi: 10.1038/hr.2010.113. Epub 2010 Jul 8.
25. Vanholder R, Baurmeister U, Brunet P, Cohen G, Glorieux G, Jankowski J: A bench to bedside view of uremic toxins. J Am Soc Nephrol. 2008 May;19(5):863-70. doi: 10.1681/ASN.2007121377. Epub 2008 Feb 20.
26. Matsumura T, Uryu O, Matsuhisa F, Tajiri K, Matsumoto H, Hayakawa Y: N-acetyl-l-tyrosine is an intrinsic triggering factor of mitohormesis in stressed animals. EMBO Rep. 2020 May 6;21(5):e49211. doi: 10.15252/embr.201949211. Epub 2020 Mar 2.
27. Hayakawa Y: N-acetyltyrosine-induced redox signaling in hormesis. Biochim Biophys Acta Mol Cell Res. 2021 May;1868(6):118990. doi: 10.1016/j.bbamcr.2021.118990. Epub 2021 Feb 20.