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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:26 UTC
HMDB IDHMDB00866
Secondary Accession NumbersNone
Metabolite Identification
Common NameN-Acetyl-L-tyrosine
DescriptionAcetyltyrosine is a side chain reaction of tyrosine. It converts to tyrosine and then can be used in neurotransmitter treatment as a precursor of cathecholamine (http://www.neuroassist.com/).
Structure
Thumb
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
Chemical FormulaC11H13NO4
Average Molecular Weight223.2252
Monoisotopic Molecular Weight223.084457909
IUPAC Name(2S)-2-acetamido-3-(4-hydroxyphenyl)propanoic acid
Traditional Nameacetyl-L-tyrosine
CAS Registry Number537-55-3
SMILES
CC(=O)N[C@@H](CC1=CC=C(O)C=C1)C(O)=O
InChI Identifier
InChI=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 KeyInChIKey=CAHKINHBCWCHCF-JTQLQIEISA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-acyl-aliphatic-alpha amino acids. These are alpha amino acids carrying a N-acylated aliphatic chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-aliphatic-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-aliphatic-alpha amino acid
  • 3-phenylpropanoic-acid
  • N-acyl-l-alpha-amino acid
  • Amphetamine or derivatives
  • Phenol
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Acetamide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point149 - 152 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility297 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.51 mg/mLALOGPS
logP1.03ALOGPS
logP0.59ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)3.67ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity56.54 m3·mol-1ChemAxon
Polarizability22.21 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-02t9-1790000000-9484167b29dc57768b67View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-004i-1921000000-91d4d68bb345a8a8a747View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0059-0900000000-1a298550f3c63022066cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-1900000000-489314daf5773f9fa91eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9300000000-3a02844e3f23883a2818View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected and Quantified<10 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified331.0 +/- 74.0 uMNewborn (0-30 days old)BothPreterm birth details
UrineDetected and Quantified1.00 (0.00-2.00) umol/mmol creatinineAdult (>18 years old)BothTyrosinemia I details
UrineDetected and Quantified115.00 (30.00-200.00) umol/mmol creatinineChildren (1-13 years old)BothTyrosinemia I details
UrineDetected and Quantified10 +/- 2 umol/mmol creatinineInfant (0-1 year old)MaleAromatic L-amino acid decarboxylase deficiency details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
Associated Disorders and Diseases
Disease References
Aromatic L-amino acid decarboxylase deficiency
  1. Abdenur JE, Abeling N, Specola N, Jorge L, Schenone AB, van Cruchten AC, Chamoles NA: Aromatic l-aminoacid decarboxylase deficiency: unusual neonatal presentation and additional findings in organic acid analysis. Mol Genet Metab. 2006 Jan;87(1):48-53. Epub 2005 Nov 9. [16288991 ]
Preterm birth
  1. 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. [7815670 ]
Tyrosinemia I
  1. MetaGene [Link]
Associated OMIM IDs
  • 107930 (Aromatic L-amino acid decarboxylase deficiency)
  • 276700 (Tyrosinemia I)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022288
KNApSAcK IDNot Available
Chemspider ID61606
KEGG Compound IDC01657
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00866
Metagene LinkHMDB00866
METLIN IDNot Available
PubChem Compound68310
PDB ID3NF
ChEBI ID201465
References
Synthesis ReferenceLiu, Aifu. Preparation of N-acetyl-L-tyrosine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 5 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [6083782 ]
  2. 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. [14621123 ]
  3. 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. [9778372 ]
  4. 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. [7705801 ]
  5. 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. [7815670 ]
  6. 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. [11440179 ]
  7. 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. [10753880 ]

Enzymes

General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
GLYAT
Uniprot ID:
Q6IB77
Molecular weight:
18506.33
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Acyltransferase which transfers an acyl group to the N-terminus of glutamine. Can use phenylacetyl-CoA as an acyl donor.
Gene Name:
GLYATL1
Uniprot ID:
Q969I3
Molecular weight:
35100.895
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Conjugates numerous substrates, such as arachidonoyl-CoA and saturated medium and long-chain acyl-CoAs ranging from chain-length C8:0-CoA to C18:0-CoA, to form a variety of N-acylglycines. Shows a preference for monounsaturated fatty acid oleoyl-CoA (C18:1-CoA) as an acyl donor. Does not exhibit any activity toward C22:6-CoA and chenodeoxycholoyl-CoA, nor toward serine or alanine.
Gene Name:
GLYATL2
Uniprot ID:
Q8WU03
Molecular weight:
34277.055