ContaminantDB: 3-Methoxytyrosine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:16:49 UTC

Update Date

2016-11-09 01:09:06 UTC

Accession Number

CHEM003257

Identification

Common Name

3-Methoxytyrosine

Class

Small Molecule

Description

3-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. (1, 2, 3).

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
T3DB toxins

Contaminant Type

Amine
Animal Toxin
Ether
Food Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Methoxy-tyrosine	HMDB
3-O-Methyldopa	HMDB, MeSH
L-3-Methoxy tyrosine	HMDB
L-3-Methoxytyrosine	HMDB, MeSH
L-4-Hydroxy-3-methoxyphenylalanine	HMDB
Vanilalanine	HMDB
3-Methoxytyrosine, (L-tyr)-isomer	MeSH, HMDB
3-Methoxytyrosine, (D-tyr)-isomer	MeSH, HMDB
3-Methoxytyrosine, (L-tyr)-isomer, alpha-(14)C-labeled	MeSH, HMDB
3-Methoxytyrosine, (DL-tyr)-isomer	MeSH, HMDB
2-Amino-3-(4-hydroxy-3-methoxyphenyl)propanoate	Generator, HMDB
3-O-Methyl-dopa	MeSH, HMDB
3-OMD CPD	MeSH, HMDB
3-Methoxydopa	MeSH, HMDB
3-Methoxytyrosine	MeSH

Chemical Formula

C₁₀H₁₃NO₄

Average Molecular Mass

211.215 g/mol

Monoisotopic Mass

211.084 g/mol

CAS Registry Number

7636-26-2

IUPAC Name

2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoic acid

Traditional Name

3-O-methyldopa

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 Key

PFDUUKDQEHURQC-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Tyrosine 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

a guaiacol (CPD-11496 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Aromatic L-Aminoacid Decarboxylase Deficiency	SMP00170	Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.96 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-1.6	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	1.75	ChemAxon
pKa (Strongest Basic)	9.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.78 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	53.56 m³·mol⁻¹	ChemAxon
Polarizability	21.01 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014u-3900000000-eb354ce752704e5a36dd	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-007c-9472000000-abcc1fa0d3b31f69223e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Negative	splash10-00di-1920000000-7d54920357df11daddb1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-02t9-0930000000-c2ec893f0b2d690b8149	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-a91930d8f8538ef1574f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-3900000000-1cea4dc97d1eb674a768	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0290000000-37322740518e056012f1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-1950000000-7d97cb07b9e8e3079548	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-7900000000-e99315a95aa2bdd3c30c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0090000000-78e52f9c7af96bfee33a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-6900000000-70c616cb8fba2824ccdf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fkc-9500000000-4e3895853fa75df2bcb1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03xr-0980000000-e506ae114e636e7fe4a5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1910000000-edbdead984fe371e39de	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052r-4900000000-7cc4de1760e6f692036f	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Methoxytyrosine is one of the main biochemical markers for aromatic L-amino acid decarboxylase deficiency, an inborn error of metabolism that affects serotonin and dopamine biosynthesis. 3-Methoxytyrosine is elevated in CSF, plasma, and urine. Catechol-O-methyl transferase is the enzyme in charge of 3-methoxytyrosine formation, which is produced from L-DOPA in many organs. Nevertheless, its half-life (15 hours approximately) is longer than the L-DOPA 's half-life, which is about one hour. This means that it is accumulated in the plasma and the brain of chronic L-DOPA therapy patients such as people suffering from Parkinson's disease. 3-Methoxytyrosine has some effects on L-DOPA related motor dysfunction, inhibition of striatal uptake of tyrosine, competition with L-DOPA for the blood–brain barrier transporter system and inhibition of dopamine release. 3-Methoxytyrosine increases homocysteine levels, and this amino acid induces cardiovascular disease and neuronal damage. Some other toxic effects could be oxidative DNA damage which can cause cell death, a decrease in locomotor activities and diminishment in mitochondrial membrane potential. (Wikipedia)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Minimum Risk Level

Not Available

Health Effects

Chronically high levels of 3-methoxytyrosine are associated with Aromatic L-Amino acid Decarboxylase Deficiency.

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0259656

FooDB ID

FDB022620

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

1607

ChEBI ID

Not Available

PubChem Compound ID

Not Available

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Zampella 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.

MSDS

Link

General References

Not Available

3-Methoxytyrosine (CHEM003257)

Structure for CHEM003257: 3-Methoxytyrosine