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Human Metabolome Database Version 2.5

 

Showing metabocard for N-Acetyl-L-tyrosine (HMDB00866)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2005-11-16 15:48:42
Update Date 2009-07-13 13:16:28
Accession Number HMDB00866
Secondary Accession Numbers Not Available
Common Name N-Acetyl-L-tyrosine
Description Acetyltyrosine 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/).
Synonyms
  1. (2S)-2-Acetylamino-3-(4-hydroxyphenyl)propanoate
  2. (2S)-2-Acetylamino-3-(4-hydroxyphenyl)propanoic acid
  3. L-N-Acetyltyrosine
  4. L-N-acetyl-Tyrosine
  5. N-Acetyl-L-tyrosine
  6. N-Acetyl-tyrosine
  7. N-Acetyltyrosine
  8. N-acetyl-4-hydroxyphenylalanine
Chemical IUPAC Name 2-acetylamino-3-(4-hydroxyphenyl)-propanoic acid
Chemical Formula C11H13NO4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Amino acids and Amino Acid conjugates
Class
  • Amino Acids
Sub Class
  • NA
Family
  • Mammalian Metabolite
Species
  • phenol or hydroxyhetarene
  • carboxylic acid
  • secondary carboxylic acid amide
  • aromatic compound
Biofunction
  • Protein synthesis, amino acid biosynthesis
Application
—
Source
  • Endogenous
Average Molecular Weight 223.225
Monoisotopic Molecular Weight 223.084457
Isomeric SMILES CC(=O)N[C@@H](CC1=CC=C(O)C=C1)C(O)=O
Canonical SMILES CC(=O)NC(CC1=CC=C(O)C=C1)C(O)=O
KEGG Compound ID C01657 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00866 Link Image
Metagene Link HMDB00866 Link Image
METLIN ID Not Available
PubChem Compound 68310 Link Image
PubChem Substance 3154274 Link Image
ChEBI ID 28828 Link Image
CAS Registry Number 537-55-3
InChI Identifier InChI=1/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
Synthesis Reference Liu, Aifu. Preparation of N-acetyl-L-tyrosine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 5 pp.
Melting Point (Experimental) 149 - 152 oC
Experimental Water Solubility 297 mg/mL [HMP expt] Source: PhysProp
Predicted Water Solubility 9.38 mg/mL [MEYLAN,WM et al. (1996)]; 2.51 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 1.03 [Predicted by ALOGPS]; -1.5 [Predicted by PubChem via XLOGP]; 1.48 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Varian)
Show Experimental Conditions Link Image
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
Show Experimental Conditions Link Image
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
Show Experimental Conditions Link Image
High Energy
Download File
Show Experimental Conditions Link Image
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm (Predicted from Solubility)
Biofluid Location
  • Blood
  • Urine
Tissue Location Not Available
Concentrations (Normal)
Biofluid Urine
Value 1.00 (0.00-2.00) umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Condition Normal
Comments Not Available
References
Concentrations (Abnormal)
Biofluid Blood
Value 331.0 +/- 74.0 uM
Age Newborn:0-30 days old
Sex Both
Condition Preterm birth
Comments Not Available
References
  • 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. [PubMed Link Image]
Biofluid Urine
Value 115.00 (30.00-200.00) umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Condition Tyrosinemia I
Comments Not Available
References
Biofluid Urine
Value 10 +/- 2 umol/mmol creatinine
Age Infant:0-1 yr old
Sex Male
Condition Aromatic L-amino acid decarboxylase deficiency
Comments Not Available
References
  • 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. [PubMed Link Image]
Associated Disorders
Condition References
Aromatic L-amino acid decarboxylase deficiency
  • 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. [PubMed Link Image]
Preterm birth
  • 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. [PubMed Link Image]
Tyrosinemia I
OMIM ID Not Available
Pathways Not Available
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. [PubMed Link Image]
  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. [PubMed Link Image]
  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. [PubMed Link Image]
  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. [PubMed Link Image]
  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. [PubMed Link Image]
  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. [PubMed Link Image]
  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. [PubMed Link Image]
Metabolic Enzymes
  1. Glycine N-acyltransferase
  2. Glycine N-acyltransferase-like protein 1
  3. Glycine N-acyltransferase-like protein 2
Enzyme 1 [top]
Enzyme 1 ID 12971
Enzyme 1 Name Glycine N-acyltransferase
Enzyme 1 Synonyms
  1. Acyl-CoA:glycine N-acyltransferase
  2. AAc
  3. Aralkyl acyl-CoA N-acyltransferase
  4. Aralkyl acyl-CoA:amino acid N-acyltransferase
  5. HRP-1(CLP)
Enzyme 1 Gene Name GLYAT
Enzyme 1 Protein Sequence >Glycine N-acyltransferase 
MMLPLQGAQMLQMLEKSLRKSLPASLKVYGTVFHINHGNPFNLKAVVDKWPDFNTVVVCP
QEQDMTDDLDHYTNTYQIYSKDPQNCQEFLGSPELINWKQHLQIQSSQPSLNEAIQNLAA
IKSFKVKQTQRILYMAAETAKELTPFLLKSKILSPSGGKPKAINQEMFKLSSMDVTHAHL
VNKFWHFGGNERSQRFIERCIQTFPTCCLLGPEGTPVCWDLMDQTGEMRMAGTLPEYRLH
GLVTYVIYSHAQKLGKLGFPVYSHVDYSNEAMQKMSYTLQHVPIPRSWNQWNCVPL
Enzyme 1 Number of Residues 296
Enzyme 1 Molecular Weight 33898
Enzyme 1 Theoretical pI 8.28
Enzyme 1 GO Classification Not Available
Enzyme 1 General Function Not Available
Enzyme 1 Specific Function Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Can conjugate a multitude of substrates to form a variety of N-acylglycines
Enzyme 1 Pathways Not Available
Enzyme 1 Reactions
  • Acyl-CoA + glycine = CoA + N-acylglycine
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 2554941 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q6IB77 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name GLYAT_HUMAN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence Not Available
Enzyme 1 GenBank Gene ID AF023466 Link Image
Enzyme 1 GeneCard ID Q6IB77 Link Image
Enzyme 1 GenAtlas ID GLYAT Link Image
Enzyme 1 HGNC ID HGNC:13734 Link Image
Enzyme 1 Chromosome Location Not Available
Enzyme 1 Locus Not Available
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References Not Available
Enzyme 1 Metabolite References Not Available
Enzyme 2 [top]
Enzyme 2 ID 12972
Enzyme 2 Name Glycine N-acyltransferase-like protein 1
Enzyme 2 Synonyms
  1. Acyl-CoA:glycine N-acyltransferase-like protein 1
Enzyme 2 Gene Name GLYATL1
Enzyme 2 Protein Sequence >Glycine N-acyltransferase-like protein 1 
MILLNNSHKLLALYKSLARSIPESLKVYGSVYHINHGNPFNMEVLVDSWPEYQMVIIRPQ
KQEMTDDMDSYTNVYRMFSKEPQKSEEVLKNCEIVNWKQRLQIQGLQESLGEGIRVATFS
KSVKVEHSRALLLVTEDILKLNASSKSKLGSWAETGHPDDEFESETPNFKYAQLDVSYSG
LVNDNWKRGKNERSLHYIKRCIEDLPAACMLGPEGVPVSWVTMDPSCEVGMAYSMEKYRR
TGNMARVMVRYMKYLRQKNIPFYISVLEENEDSRRFVGQFGFFEASCEWHQWTCYPQNLV
PF
Enzyme 2 Number of Residues 302
Enzyme 2 Molecular Weight 35102
Enzyme 2 Theoretical pI 6.86
Enzyme 2 GO Classification Not Available
Enzyme 2 General Function Not Available
Enzyme 2 Specific Function Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Can conjugate a multitude of substrates to form a variety of N-acylglycines
Enzyme 2 Pathways Not Available
Enzyme 2 Reactions
  • Acyl-CoA + glycine = CoA + N-acylglycine
Enzyme 2 Pfam Domain Function
Enzyme 2 Signals
  • None
Enzyme 2 Transmembrane Regions
  • None
Enzyme 2 Essentiality Not Available
Enzyme 2 GenBank ID Protein 71384826 Link Image
Enzyme 2 UniProtKB/Swiss-Prot ID Q969I3 Link Image
Enzyme 2 UniProtKB/Swiss-Prot Entry Name GLYL1_HUMAN Link Image
Enzyme 2 PDB ID Not Available
Enzyme 2 Cellular Location Not Available
Enzyme 2 Gene Sequence Not Available
Enzyme 2 GenBank Gene ID DQ084381 Link Image
Enzyme 2 GeneCard ID Q969I3 Link Image
Enzyme 2 GenAtlas ID GLYATL1 Link Image
Enzyme 2 HGNC ID HGNC:30519 Link Image
Enzyme 2 Chromosome Location Not Available
Enzyme 2 Locus Not Available
Enzyme 2 SNPs SNPJam Report Link Image
Enzyme 2 General References Not Available
Enzyme 2 Metabolite References Not Available
Enzyme 3 [top]
Enzyme 3 ID 12973
Enzyme 3 Name Glycine N-acyltransferase-like protein 2
Enzyme 3 Synonyms
  1. Acyl-CoA:glycine N-acyltransferase-like protein 2
Enzyme 3 Gene Name GLYATL2
Enzyme 3 Protein Sequence >Glycine N-acyltransferase-like protein 2 
MLVLHNSQKLQILYKSLEKSIPESIKVYGAIFNIKDKNPFNMEVLVDAWPDYQIVITRPQ
KQEMKDDQDHYTNTYHIFTKAPDKLEEVLSYSNVISWEQTLQIQGCQEGLDEAIRKVATS
KSVQVDYMKTILFIPELPKKHKTSSNDKMELFEVDDDNKEGNFSNMFLDASHAGLVNEHW
AFGKNERSLKYIERCLQDFLGFGVLGPEGQLVSWIVMEQSCELRMGYTVPKYRHQGNMLQ
IGYHLEKYLSQKEIPFYFHVADNNEKSLQALNNLGFKICPCGWHQWKCTPKKYC
Enzyme 3 Number of Residues 294
Enzyme 3 Molecular Weight 34278
Enzyme 3 Theoretical pI 6.67
Enzyme 3 GO Classification Not Available
Enzyme 3 General Function Not Available
Enzyme 3 Specific Function Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Can conjugate a multitude of substrates to form a variety of N-acylglycines
Enzyme 3 Pathways Not Available
Enzyme 3 Reactions
  • Acyl-CoA + glycine = CoA + N-acylglycine
Enzyme 3 Pfam Domain Function
Enzyme 3 Signals
  • None
Enzyme 3 Transmembrane Regions
  • None
Enzyme 3 Essentiality Not Available
Enzyme 3 GenBank ID Protein 29243559 Link Image
Enzyme 3 UniProtKB/Swiss-Prot ID Q8WU03 Link Image
Enzyme 3 UniProtKB/Swiss-Prot Entry Name GLYL2_HUMAN Link Image
Enzyme 3 PDB ID Not Available
Enzyme 3 Cellular Location Not Available
Enzyme 3 Gene Sequence Not Available
Enzyme 3 GenBank Gene ID AF426250 Link Image
Enzyme 3 GeneCard ID Q8WU03 Link Image
Enzyme 3 GenAtlas ID GLYATL2 Link Image
Enzyme 3 HGNC ID HGNC:24178 Link Image
Enzyme 3 Chromosome Location Not Available
Enzyme 3 Locus Not Available
Enzyme 3 SNPs SNPJam Report Link Image
Enzyme 3 General References Not Available
Enzyme 3 Metabolite References Not Available