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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:40 UTC
HMDB IDHMDB01434
Secondary Accession Numbers
  • HMDB05881
Metabolite Identification
Common Name3-Methoxytyrosine
Description3-Methoxytyrosine is one of the main biochemical markers for Aromatic L-amino acid decarboxylase (AADC, EC 4.1.1.28) deficiency, an inborn error of metabolism that affects serotonin and dopamine biosynthesis. Patients are usually detected in infancy due to developmental delay, hypotonia, and extrapyramidal movements. Diagnosis is based on an abnormal neurotransmitter metabolite profile in CSF and reduced AADC activity in plasma. 3-methoxytyrosine is elevated in CSF, plasma, and urine. (PMID 1357595 , 1281049 , 16288991 ).
Structure
Thumb
Synonyms
ValueSource
3-Methoxy-tyrosineHMDB
3-O-MethyldopaHMDB
L-3-Methoxy tyrosineHMDB
L-3-MethoxytyrosineHMDB
L-4-Hydroxy-3-methoxyphenylalanineHMDB
VanilalanineHMDB
Chemical FormulaC10H13NO4
Average Molecular Weight211.2145
Monoisotopic Molecular Weight211.084457909
IUPAC Name2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoic acid
Traditional Name3-O-methyldopa
CAS Registry Number7636-26-2
SMILES
COC1=CC(CC(N)C(O)=O)=CC=C1O
InChI Identifier
InChI=1S/C10H13NO4/c1-15-9-5-6(2-3-8(9)12)4-7(11)10(13)14/h2-3,5,7,12H,4,11H2,1H3,(H,13,14)
InChI KeyInChIKey=PFDUUKDQEHURQC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • Methoxyphenol
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Aralkylamine
  • Phenol
  • Amino fatty acid
  • Alkyl aryl ether
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.96 mg/mLALOGPS
logP-2.1ALOGPS
logP-1.6ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.75ChemAxon
pKa (Strongest Basic)9.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.78 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.56 m3·mol-1ChemAxon
Polarizability21.01 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.089 +/- 0.032 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.05 (0.00-0.10) uMInfant (0-1 year old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.024-0.148 uMChildren (1-13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified<0.3 uMChildren (1-13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified<0.05 uMChildren (1-13 years old)MaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.025 +/- 0.025 uMAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.06 +/- 0.04 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified1.17625 (0.59-2.86) uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0105 (0.008-0.013) uMChildren (1-13 years old)Malesepiapterin reductase deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified1.2 +/- 0.0 uMInfant (0-1 year old)MaleAromatic L-amino acid decarboxylase deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified1.2 (1.0-1.6) uMAdult (>18 years old)Not SpecifiedAromatic L-amino acid decarboxylase deficiency details
Associated Disorders and Diseases
Disease References
Aromatic L-amino acid decarboxylase deficiency
  1. Hyland K, Clayton PT: Aromatic L-amino acid decarboxylase deficiency: diagnostic methodology. Clin Chem. 1992 Dec;38(12):2405-10. [1281049 ]
  2. 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 ]
Associated OMIM IDs
  • 107930 (Aromatic L-amino acid decarboxylase deficiency)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022620
KNApSAcK IDNot Available
Chemspider ID1607
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01434
Metagene LinkHMDB01434
METLIN IDNot Available
PubChem Compound1670
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceZampella Angela; D'Orsi Rosa; Sepe Valentina; Casapullo Agostino; Monti Maria Chiara; D'Auria Maria Valeria Concise synthesis of all stereoisomers of beta-methoxytyrosine and determination of the absolute configuration of the residue in callipeltin A. Organic letters (2005), 7(16), 3585-8.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Hyland K, Clayton PT: Aromatic L-amino acid decarboxylase deficiency: diagnostic methodology. Clin Chem. 1992 Dec;38(12):2405-10. [1281049 ]
  2. Hyland K, Surtees RA, Rodeck C, Clayton PT: Aromatic L-amino acid decarboxylase deficiency: clinical features, diagnosis, and treatment of a new inborn error of neurotransmitter amine synthesis. Neurology. 1992 Oct;42(10):1980-8. [1357595 ]
  3. 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 ]