Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 14:57:09 UTC

HMDB ID

HMDB0001434

Secondary Accession Numbers

HMDB0005881
HMDB01434
HMDB05881

Metabolite Identification

Common Name

3-Methoxytyrosine

Description

3-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652305261923572D          

 15 15  0  0  0  0            999 V2000
10000.732310000.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4470 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.161810000.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8766 9999.9999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.161810001.2359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.4470 9999.1770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.878910000.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1633 9999.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8789 9998.7640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.021210000.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.306710000.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.592210000.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5922 9999.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3066 9998.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0212 9999.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  7  8  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 10  1  0  0  0  0
 13  9  1  0  0  0  0
 12  7  1  0  0  0  0
  1 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001434

> <DATABASE_NAME>
hmdb

> <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_KEY>
PFDUUKDQEHURQC-UHFFFAOYSA-N

> <FORMULA>
C10H13NO4

> <MOLECULAR_WEIGHT>
211.2145

> <EXACT_MASS>
211.084457909

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.008178839374537

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoic acid

> <ALOGPS_LOGP>
-2.09

> <JCHEM_LOGP>
-1.6462719247074558

> <ALOGPS_LOGS>
-1.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.067630231890497

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7533966175828115

> <JCHEM_PKA_STRONGEST_BASIC>
9.330820827231552

> <JCHEM_POLAR_SURFACE_AREA>
92.78000000000002

> <JCHEM_REFRACTIVITY>
53.56040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.96e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-O-methyldopa

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0    8668.0348667.436   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8669.3688666.666   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8670.7028667.436   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8672.0368666.666   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8670.7028668.974   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0    8669.3688665.130   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0    8662.7078667.436   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8661.3718666.665   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8662.7078664.359   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8666.7068666.668   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8665.3738667.438   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8664.0398666.668   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8664.0398665.128   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8665.3728664.358   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8666.7068665.128   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2                                                            
CONECT    7    8   12                                                       
CONECT    8    7                                                            
CONECT    9   13                                                            
CONECT   10   11   15    1                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13    7                                                  
CONECT   13   12   14    9                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0259656
HETATM    1  C1  UNL     1      -2.681   2.367  -0.421  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.891   0.979  -0.521  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.944   0.039  -0.136  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.707   0.386   0.382  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.225  -0.563   0.761  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.532  -0.184   1.309  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.601  -0.015   0.263  1.00  0.00           C  
HETATM    8  N1  UNL     1       2.838  -1.220  -0.495  1.00  0.00           N  
HETATM    9  C7  UNL     1       2.338   1.125  -0.643  1.00  0.00           C  
HETATM   10  O2  UNL     1       2.331   1.016  -1.894  1.00  0.00           O  
HETATM   11  O3  UNL     1       2.085   2.381  -0.113  1.00  0.00           O  
HETATM   12  C8  UNL     1      -0.131  -1.885   0.600  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.375  -2.249   0.078  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.269  -1.286  -0.284  1.00  0.00           C  
HETATM   15  O4  UNL     1      -3.507  -1.646  -0.803  1.00  0.00           O  
HETATM   16  H1  UNL     1      -1.682   2.602  -0.860  1.00  0.00           H  
HETATM   17  H2  UNL     1      -3.459   2.883  -1.040  1.00  0.00           H  
HETATM   18  H3  UNL     1      -2.749   2.636   0.652  1.00  0.00           H  
HETATM   19  H4  UNL     1      -0.490   1.434   0.482  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.466   0.770   1.871  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.926  -0.938   2.045  1.00  0.00           H  
HETATM   22  H7  UNL     1       3.547   0.220   0.806  1.00  0.00           H  
HETATM   23  H8  UNL     1       2.825  -2.054   0.130  1.00  0.00           H  
HETATM   24  H9  UNL     1       3.802  -1.126  -0.933  1.00  0.00           H  
HETATM   25  H10 UNL     1       1.264   2.918  -0.277  1.00  0.00           H  
HETATM   26  H11 UNL     1       0.523  -2.698   0.865  1.00  0.00           H  
HETATM   27  H12 UNL     1      -1.636  -3.295  -0.040  1.00  0.00           H  
HETATM   28  H13 UNL     1      -3.782  -2.598  -0.927  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3
CONECT    3    4    4   14
CONECT    4    5   19
CONECT    5    6   12   12
CONECT    6    7   20   21
CONECT    7    8    9   22
CONECT    8   23   24
CONECT    9   10   10   11
CONECT   11   25
CONECT   12   13   26
CONECT   13   14   14   27
CONECT   14   15
CONECT   15   28
END

View in JSmol View NMR Assignments View Stereo Labels

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 Weight

211.2145

Monoisotopic Molecular Weight

211.084457909

IUPAC Name

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

Traditional Name

3-O-methyldopa

CAS Registry Number

7636-26-2

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 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 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	148.3	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002060
[M+H]+	Not Available	153.5	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002060

Predicted Molecular 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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	150.706	31661259
DarkChem	[M-H]-	149.12	31661259
AllCCS	[M+H]+	147.884	32859911
AllCCS	[M-H]-	146.057	32859911
DeepCCS	[M+H]+	147.852	30932474
DeepCCS	[M-H]-	145.494	30932474
DeepCCS	[M-2H]-	179.724	30932474
DeepCCS	[M+Na]+	154.713	30932474
AllCCS	[M+H]+	147.9	32859911
AllCCS	[M+H-H2O]+	143.9	32859911
AllCCS	[M+NH4]+	151.6	32859911
AllCCS	[M+Na]+	152.6	32859911
AllCCS	[M-H]-	146.1	32859911
AllCCS	[M+Na-2H]-	146.6	32859911
AllCCS	[M+HCOO]-	147.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methoxytyrosine	COC1=C(O)C=CC(CC(N)C(O)=O)=C1	3309.9	Standard polar	33892256
3-Methoxytyrosine	COC1=C(O)C=CC(CC(N)C(O)=O)=C1	2002.9	Standard non polar	33892256
3-Methoxytyrosine	COC1=C(O)C=CC(CC(N)C(O)=O)=C1	2016.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methoxytyrosine,1TMS,isomer #1	COC1=CC(CC(N)C(=O)O)=CC=C1O[Si](C)(C)C	2045.6	Semi standard non polar	33892256
3-Methoxytyrosine,1TMS,isomer #2	COC1=CC(CC(N)C(=O)O[Si](C)(C)C)=CC=C1O	1967.4	Semi standard non polar	33892256
3-Methoxytyrosine,1TMS,isomer #3	COC1=CC(CC(N[Si](C)(C)C)C(=O)O)=CC=C1O	2053.7	Semi standard non polar	33892256
3-Methoxytyrosine,2TMS,isomer #1	COC1=CC(CC(N)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2030.3	Semi standard non polar	33892256
3-Methoxytyrosine,2TMS,isomer #2	COC1=CC(CC(N[Si](C)(C)C)C(=O)O)=CC=C1O[Si](C)(C)C	2066.6	Semi standard non polar	33892256
3-Methoxytyrosine,2TMS,isomer #3	COC1=CC(CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O	2008.8	Semi standard non polar	33892256
3-Methoxytyrosine,2TMS,isomer #4	COC1=CC(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O	2181.7	Semi standard non polar	33892256
3-Methoxytyrosine,3TMS,isomer #1	COC1=CC(CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2044.7	Semi standard non polar	33892256
3-Methoxytyrosine,3TMS,isomer #1	COC1=CC(CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2086.1	Standard non polar	33892256
3-Methoxytyrosine,3TMS,isomer #1	COC1=CC(CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2339.8	Standard polar	33892256
3-Methoxytyrosine,3TMS,isomer #2	COC1=CC(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2216.2	Semi standard non polar	33892256
3-Methoxytyrosine,3TMS,isomer #2	COC1=CC(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2158.2	Standard non polar	33892256
3-Methoxytyrosine,3TMS,isomer #2	COC1=CC(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2510.3	Standard polar	33892256
3-Methoxytyrosine,3TMS,isomer #3	COC1=CC(CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O	2169.3	Semi standard non polar	33892256
3-Methoxytyrosine,3TMS,isomer #3	COC1=CC(CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O	2245.5	Standard non polar	33892256
3-Methoxytyrosine,3TMS,isomer #3	COC1=CC(CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O	2514.8	Standard polar	33892256
3-Methoxytyrosine,4TMS,isomer #1	COC1=CC(CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2262.6	Semi standard non polar	33892256
3-Methoxytyrosine,4TMS,isomer #1	COC1=CC(CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2204.8	Standard non polar	33892256
3-Methoxytyrosine,4TMS,isomer #1	COC1=CC(CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2289.8	Standard polar	33892256
3-Methoxytyrosine,1TBDMS,isomer #1	COC1=CC(CC(N)C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	2300.0	Semi standard non polar	33892256
3-Methoxytyrosine,1TBDMS,isomer #2	COC1=CC(CC(N)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	2232.7	Semi standard non polar	33892256
3-Methoxytyrosine,1TBDMS,isomer #3	COC1=CC(CC(N[Si](C)(C)C(C)(C)C)C(=O)O)=CC=C1O	2317.9	Semi standard non polar	33892256
3-Methoxytyrosine,2TBDMS,isomer #1	COC1=CC(CC(N)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2523.2	Semi standard non polar	33892256
3-Methoxytyrosine,2TBDMS,isomer #2	COC1=CC(CC(N[Si](C)(C)C(C)(C)C)C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	2558.2	Semi standard non polar	33892256
3-Methoxytyrosine,2TBDMS,isomer #3	COC1=CC(CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	2502.2	Semi standard non polar	33892256
3-Methoxytyrosine,2TBDMS,isomer #4	COC1=CC(CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O	2653.2	Semi standard non polar	33892256
3-Methoxytyrosine,3TBDMS,isomer #1	COC1=CC(CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2755.7	Semi standard non polar	33892256
3-Methoxytyrosine,3TBDMS,isomer #1	COC1=CC(CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2721.3	Standard non polar	33892256
3-Methoxytyrosine,3TBDMS,isomer #1	COC1=CC(CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2701.6	Standard polar	33892256
3-Methoxytyrosine,3TBDMS,isomer #2	COC1=CC(CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2920.5	Semi standard non polar	33892256
3-Methoxytyrosine,3TBDMS,isomer #2	COC1=CC(CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2768.7	Standard non polar	33892256
3-Methoxytyrosine,3TBDMS,isomer #2	COC1=CC(CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2777.7	Standard polar	33892256
3-Methoxytyrosine,3TBDMS,isomer #3	COC1=CC(CC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O	2865.6	Semi standard non polar	33892256
3-Methoxytyrosine,3TBDMS,isomer #3	COC1=CC(CC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O	2859.6	Standard non polar	33892256
3-Methoxytyrosine,3TBDMS,isomer #3	COC1=CC(CC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O	2767.5	Standard polar	33892256
3-Methoxytyrosine,4TBDMS,isomer #1	COC1=CC(CC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3149.6	Semi standard non polar	33892256
3-Methoxytyrosine,4TBDMS,isomer #1	COC1=CC(CC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2963.0	Standard non polar	33892256
3-Methoxytyrosine,4TBDMS,isomer #1	COC1=CC(CC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2701.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxytyrosine GC-MS (Non-derivatized) - 70eV, Positive	splash10-014u-3900000000-eb354ce752704e5a36dd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxytyrosine GC-MS (2 TMS) - 70eV, Positive	splash10-007c-9472000000-abcc1fa0d3b31f69223e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxytyrosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxytyrosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxytyrosine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxytyrosine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxytyrosine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxytyrosine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxytyrosine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxytyrosine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxytyrosine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxytyrosine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxytyrosine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxytyrosine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxytyrosine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxytyrosine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxytyrosine GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methoxytyrosine 6V, Negative-QTOF	splash10-00di-1920000000-7d54920357df11daddb1	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxytyrosine 10V, Positive-QTOF	splash10-02t9-0930000000-c2ec893f0b2d690b8149	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxytyrosine 20V, Positive-QTOF	splash10-014i-0900000000-a91930d8f8538ef1574f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxytyrosine 40V, Positive-QTOF	splash10-000i-3900000000-1cea4dc97d1eb674a768	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxytyrosine 10V, Negative-QTOF	splash10-03di-0290000000-37322740518e056012f1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxytyrosine 20V, Negative-QTOF	splash10-03di-1950000000-7d97cb07b9e8e3079548	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxytyrosine 40V, Negative-QTOF	splash10-00di-7900000000-e99315a95aa2bdd3c30c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxytyrosine 10V, Negative-QTOF	splash10-03di-0090000000-78e52f9c7af96bfee33a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxytyrosine 20V, Negative-QTOF	splash10-00di-6900000000-70c616cb8fba2824ccdf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxytyrosine 40V, Negative-QTOF	splash10-0fkc-9500000000-4e3895853fa75df2bcb1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxytyrosine 10V, Positive-QTOF	splash10-03xr-0980000000-e506ae114e636e7fe4a5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxytyrosine 20V, Positive-QTOF	splash10-03di-1910000000-edbdead984fe371e39de	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxytyrosine 40V, Positive-QTOF	splash10-052r-4900000000-7cc4de1760e6f692036f	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 500 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.089 +/- 0.032 uM	Adult (>18 years old)	Both	Normal	1770109	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.05 (0.00-0.10) uM	Infant (0-1 year old)	Not Specified	Normal	16288991	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	<0.300 uM	Newborn (0-30 days old)	Not Specified	Normal	17068770	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0-0.310 uM	Newborn (0-30 days old)	Not Specified	Normal	27912044	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.024-0.148 uM	Children (1-13 years old)	Not Specified	Normal	18294893	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	<0.3 uM	Children (1-13 years old)	Not Specified	Normal	18294893	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	<0.05 uM	Children (1-13 years old)	Male	Normal	18502672	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.025 +/- 0.025 uM	Adult (>18 years old)	Not Specified	Normal	1281049	details
Urine	Detected and Quantified	0.06 +/- 0.04 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	1770109	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.17625 (0.59-2.86) uM	Newborn (0-30 days old)	Not Specified	PNPO deficiency	18294893	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0105 (0.008-0.013) uM	Children (1-13 years old)	Male	sepiapterin reductase deficiency	18502672	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.2 +/- 0.0 uM	Infant (0-1 year old)	Male	Aromatic L-amino acid decarboxylase deficiency	16288991	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.885-5.604 uM	Newborn (0-30 days old)	Both	Pyridoxamine 5-prime-phosphate oxidase deficiency	17068770	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.508-0.586 uM	Newborn (0-30 days old)	Female	Epilepsy, early-onset, vitamin B6-dependent	27912044	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.2 (1.0-1.6) uM	Adult (>18 years old)	Not Specified	Aromatic L-amino acid decarboxylase deficiency	1281049	details

Associated Disorders and Diseases

Disease References

Aromatic L-amino acid decarboxylase deficiency
Hyland K, Clayton PT: Aromatic L-amino acid decarboxylase deficiency: diagnostic methodology. Clin Chem. 1992 Dec;38(12):2405-10. [PubMed:1281049 ] 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
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 ] 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
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
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)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022620

KNApSAcK ID

Not Available

Chemspider ID

1607

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000324

Good Scents 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.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Hyland K, Clayton PT: Aromatic L-amino acid decarboxylase deficiency: diagnostic methodology. Clin Chem. 1992 Dec;38(12):2405-10. [PubMed:1281049 ]
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 ]
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 ]

Showing metabocard for 3-Methoxytyrosine (HMDB0001434)

MOL for HMDB0001434 (3-Methoxytyrosine)

3D MOL for HMDB0001434 (3-Methoxytyrosine)

3D SDF for HMDB0001434 (3-Methoxytyrosine)

3D-SDF for HMDB0001434 (3-Methoxytyrosine)

PDB for HMDB0001434 (3-Methoxytyrosine)

3D PDB for HMDB0001434 (3-Methoxytyrosine)

SMILES for HMDB0001434 (3-Methoxytyrosine)

INCHI for HMDB0001434 (3-Methoxytyrosine)

Structure for HMDB0001434 (3-Methoxytyrosine)

3D Structure for HMDB0001434 (3-Methoxytyrosine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra