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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 14:57:09 UTC
HMDB IDHMDB0001434
Secondary Accession Numbers
  • HMDB0005881
  • HMDB01434
  • HMDB05881
Metabolite Identification
Common Name3-Methoxytyrosine
Description3-Methoxytyrosine, also known as 3-O-methyldopa or vanilalanine, 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. 3-Methoxytyrosine is one of the main biochemical markers for Aromatic L-amino acid decarboxylase (AADC, EC4.1.1.28) deficiency, an inborn error of metabolism that affects serotonin and dopamine biosynthesis. Chronically high levels of 3-methoxytyrosine are associated with aromatic L-amino acid decarboxylase (AADC, 28) deficiency, an inborn error of metabolism that affects serotonin and dopamine biosynthesis. 3-Methoxytyrosine is a potentially toxic compound. 3-Methoxytyrosine, with regard to humans, has been found to be associated with several diseases such as epilepsy, early-onset, vitamin b6-dependent and pyridoxamine 5-prime-phosphate oxidase deficiency; 3-methoxytyrosine has also been linked to several inborn metabolic disorders including sepiapterin reductase deficiency and aromatic l-amino acid decarboxylase deficiency.
Structure
Thumb
Synonyms
ValueSource
3-Methoxy-tyrosineHMDB
3-O-MethyldopaHMDB, MeSH
L-3-Methoxy tyrosineHMDB
L-3-MethoxytyrosineHMDB, MeSH
L-4-Hydroxy-3-methoxyphenylalanineHMDB
VanilalanineHMDB
3-Methoxytyrosine, (L-tyr)-isomerMeSH, HMDB
3-Methoxytyrosine, (D-tyr)-isomerMeSH, HMDB
3-Methoxytyrosine, (L-tyr)-isomer, alpha-(14)C-labeledMeSH, HMDB
3-Methoxytyrosine, (DL-tyr)-isomerMeSH, HMDB
2-Amino-3-(4-hydroxy-3-methoxyphenyl)propanoateGenerator, HMDB
3-O-Methyl-dopaMeSH, HMDB
3-OMD CPDMeSH, HMDB
3-MethoxydopaMeSH, HMDB
3-MethoxytyrosineMeSH
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=C(O)C=CC(CC(N)C(O)=O)=C1
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 KeyPFDUUKDQEHURQC-UHFFFAOYSA-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
  • 3-phenylpropanoic-acid
  • Alpha-amino acid
  • Amphetamine or derivatives
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Amino acid
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Primary amine
  • Amine
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available148.3http://allccs.zhulab.cn/database/detail?ID=AllCCS00002060
[M+H]+Not Available153.5http://allccs.zhulab.cn/database/detail?ID=AllCCS00002060
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 Quantified0.885-5.604 uMNewborn (0-30 days old)BothPyridoxamine 5-prime-phosphate oxidase deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.508-0.586 uMNewborn (0-30 days old)FemaleEpilepsy, early-onset, vitamin B6-dependent 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. [PubMed: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. [PubMed:16288991 ]
Pyridoxamine 5-prime-phosphate oxidase deficiency
  1. Ormazabal A, Oppenheim M, Serrano M, Garcia-Cazorla A, Campistol J, Ribes A, Ruiz A, Moreno J, Hyland K, Clayton P, Heales S, Artuch R: Pyridoxal 5'-phosphate values in cerebrospinal fluid: reference values and diagnosis of PNPO deficiency in paediatric patients. Mol Genet Metab. 2008 Jun;94(2):173-7. doi: 10.1016/j.ymgme.2008.01.004. Epub 2008 Feb 21. [PubMed:18294893 ]
  2. Plecko B, Paul K, Paschke E, Stoeckler-Ipsiroglu S, Struys E, Jakobs C, Hartmann H, Luecke T, di Capua M, Korenke C, Hikel C, Reutershahn E, Freilinger M, Baumeister F, Bosch F, Erwa W: Biochemical and molecular characterization of 18 patients with pyridoxine-dependent epilepsy and mutations of the antiquitin (ALDH7A1) gene. Hum Mutat. 2007 Jan;28(1):19-26. [PubMed:17068770 ]
Sepiapterin reductase deficiency
  1. Verbeek MM, Willemsen MA, Wevers RA, Lagerwerf AJ, Abeling NG, Blau N, Thony B, Vargiami E, Zafeiriou DI: Two Greek siblings with sepiapterin reductase deficiency. Mol Genet Metab. 2008 Aug;94(4):403-9. doi: 10.1016/j.ymgme.2008.04.003. Epub 2008 May 27. [PubMed:18502672 ]
Epilepsy, early-onset, vitamin B6-dependent
  1. Darin N, Reid E, Prunetti L, Samuelsson L, Husain RA, Wilson M, El Yacoubi B, Footitt E, Chong WK, Wilson LC, Prunty H, Pope S, Heales S, Lascelles K, Champion M, Wassmer E, Veggiotti P, de Crecy-Lagard V, Mills PB, Clayton PT: Mutations in PROSC Disrupt Cellular Pyridoxal Phosphate Homeostasis and Cause Vitamin-B6-Dependent Epilepsy. Am J Hum Genet. 2016 Dec 1;99(6):1325-1337. doi: 10.1016/j.ajhg.2016.10.011. [PubMed:27912044 ]
Associated OMIM IDs
  • 608643 (Aromatic L-amino acid decarboxylase deficiency)
  • 610090 (Pyridoxamine 5-prime-phosphate oxidase deficiency)
  • 182125 (Sepiapterin reductase deficiency)
  • 617290 (Epilepsy, early-onset, vitamin B6-dependent)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022620
KNApSAcK IDNot Available
Chemspider ID1607
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000324
Good Scents 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)Not Available
General References
  1. Hyland K, Clayton PT: Aromatic L-amino acid decarboxylase deficiency: diagnostic methodology. Clin Chem. 1992 Dec;38(12):2405-10. [PubMed: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. [PubMed: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. [PubMed:16288991 ]