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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2023-02-21 17:18:19 UTC

HMDB ID

HMDB0014903

Secondary Accession Numbers

HMDB14903

Metabolite Identification

Common Name

Metyrosine

Description

Metyrosine is only found in individuals that have used or taken this drug. It is an inhibitor of the enzyme tyrosine 3-monooxygenase, and consequently of the synthesis of catecholamines. It is used to control the symptoms of excessive sympathetic stimulation in patients with pheochromocytoma. (Martindale, The Extra Pharmacopoeia, 30th ed)Metyrosine inhibits tyrosine hydroxylase, which catalyzes the first transformation in catecholamine biosynthesis, i.e., the conversion of tyrosine to dihydroxyphenylalanine (DOPA). Because the first step is also the rate-limiting step, blockade of tyrosine hydroxylase activity results in decreased endogenous levels of catecholamines and their synthesis. This consequently, depletes the levels of the catecholamines dopamine, adrenaline and noradrenaline in the body,usually measured as decreased urinary excretion of catecholamines and their metabolites. One main end result of the catecholamine depletion is a decrease in blood presure.

Structure

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

765
  Mrv0541 02231214592D          

 14 14  0  0  1  0            999 V2000
    3.7935    2.4751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.4751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916    0.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  9  2  0  0  0  0
  3 14  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  7 10  2  0  0  0  0
  7 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  2  0  0  0  0
 12 14  2  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014903

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@](N)(CC1=CC=C(O)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H13NO3/c1-10(11,9(13)14)6-7-2-4-8(12)5-3-7/h2-5,12H,6,11H2,1H3,(H,13,14)/t10-/m0/s1

> <INCHI_KEY>
NHTGHBARYWONDQ-JTQLQIEISA-N

> <FORMULA>
C10H13NO3

> <MOLECULAR_WEIGHT>
195.2151

> <EXACT_MASS>
195.089543287

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
19.898168653060495

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid

> <ALOGPS_LOGP>
-1.91

> <JCHEM_LOGP>
-1.0558642369962035

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.29383753269354

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.0631347229761277

> <JCHEM_PKA_STRONGEST_BASIC>
9.926935245424286

> <JCHEM_POLAR_SURFACE_AREA>
83.55

> <JCHEM_REFRACTIVITY>
51.81050000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.48e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
metyrosine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 765                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       7.081   4.620   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.415   2.310   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       4.414  -4.620   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       4.977   3.644   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       5.748   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.518   0.976   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.080  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414  -3.080   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3   14                                                            
CONECT    4    5                                                            
CONECT    5    4    6    8    9                                             
CONECT    6    5    7                                                       
CONECT    7    6   10   11                                                  
CONECT    8    5                                                            
CONECT    9    1    2    5                                                  
CONECT   10    7   12                                                       
CONECT   11    7   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   14                                                       
CONECT   14    3   12   13                                                  
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0014903
HETATM    1  C1  UNL     1      -1.537  -1.197   1.027  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.759  -0.268  -0.148  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.957  -0.766  -0.842  1.00  0.00           N  
HETATM    4  C3  UNL     1      -0.630  -0.377  -1.144  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.684  -0.044  -0.623  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.196   1.232  -0.666  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.462   1.522  -0.156  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.216   0.529   0.399  1.00  0.00           C  
HETATM    9  O1  UNL     1       4.481   0.829   0.906  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.726  -0.743   0.451  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.465  -1.028  -0.058  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.980   1.079   0.372  1.00  0.00           C  
HETATM   13  O2  UNL     1      -1.076   1.663   1.001  1.00  0.00           O  
HETATM   14  O3  UNL     1      -3.184   1.748   0.189  1.00  0.00           O  
HETATM   15  H1  UNL     1      -1.167  -2.190   0.664  1.00  0.00           H  
HETATM   16  H2  UNL     1      -2.489  -1.320   1.567  1.00  0.00           H  
HETATM   17  H3  UNL     1      -0.825  -0.730   1.741  1.00  0.00           H  
HETATM   18  H4  UNL     1      -3.586   0.005  -1.106  1.00  0.00           H  
HETATM   19  H5  UNL     1      -2.717  -1.407  -1.612  1.00  0.00           H  
HETATM   20  H6  UNL     1      -0.645  -1.450  -1.497  1.00  0.00           H  
HETATM   21  H7  UNL     1      -0.846   0.219  -2.052  1.00  0.00           H  
HETATM   22  H8  UNL     1       0.657   2.066  -1.090  1.00  0.00           H  
HETATM   23  H9  UNL     1       2.875   2.521  -0.184  1.00  0.00           H  
HETATM   24  H10 UNL     1       5.073   0.133   1.324  1.00  0.00           H  
HETATM   25  H11 UNL     1       3.342  -1.513   0.895  1.00  0.00           H  
HETATM   26  H12 UNL     1       1.144  -2.063   0.020  1.00  0.00           H  
HETATM   27  H13 UNL     1      -3.922   1.549   0.858  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    4   12
CONECT    3   18   19
CONECT    4    5   20   21
CONECT    5    6    6   11
CONECT    6    7   22
CONECT    7    8    8   23
CONECT    8    9   10
CONECT    9   24
CONECT   10   11   11   25
CONECT   11   26
CONECT   12   13   13   14
CONECT   14   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(-)-alpha-Methyl-L-tyrosine	ChEBI
(S)-alpha-Methyltyrosine	ChEBI
alpha-Methyl-L-p-tyrosine	ChEBI
alpha-Methyl-p-tyrosine	ChEBI
alpha-Methyl-para-tyrosine	ChEBI
alpha-Methyltyrosine	ChEBI
L-alpha-Methyltyrosine	ChEBI
Methyltyrosine	ChEBI
Metirosina	ChEBI
Metirosine	ChEBI
Metirosinum	ChEBI
Demser	Kegg
(-)-a-Methyl-L-tyrosine	Generator
(-)-Α-methyl-L-tyrosine	Generator
(S)-a-Methyltyrosine	Generator
(S)-Α-methyltyrosine	Generator
a-Methyl-L-p-tyrosine	Generator
Α-methyl-L-p-tyrosine	Generator
a-Methyl-p-tyrosine	Generator
Α-methyl-p-tyrosine	Generator
a-Methyl-para-tyrosine	Generator
Α-methyl-para-tyrosine	Generator
a-Methyltyrosine	Generator
Α-methyltyrosine	Generator
L-a-Methyltyrosine	Generator
L-Α-methyltyrosine	Generator
alpha Methyltyrosine hydrochloride	HMDB
alpha-Methyltyrosine, (+,-)-isomer	HMDB
alpha MPT	HMDB
alpha Methyl para tyrosine	HMDB
alpha-MPT	HMDB
alpha-Methyltyrosine, (D,L)-isomer	HMDB
alpha-Methyltyrosine, (L)-isomer	HMDB
Hydrochloride, alpha-methyltyrosine	HMDB
Metyrosine merck brand	HMDB
Racemetirosine	HMDB
alpha Methyl p tyrosine	HMDB
Merck brand OF metyrosine	HMDB
Merck sharp and dohme brand OF metyrosine	HMDB
alpha Methyltyrosine	HMDB
alpha-Methyltyrosine hydrochloride	HMDB
alpha-Methyl- DL-tyrosine	HMDB
a-Methyl-L-tyrosine	HMDB
Α-methyl-L-tyrosine	HMDB
Metyrosine	ChEBI

Chemical Formula

C₁₀H₁₃NO₃

Average Molecular Weight

195.2151

Monoisotopic Molecular Weight

195.089543287

IUPAC Name

(2S)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid

Traditional Name

metyrosine

CAS Registry Number

672-87-7

SMILES

C[C@](N)(CC1=CC=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C10H13NO3/c1-10(11,9(13)14)6-7-2-4-8(12)5-3-7/h2-5,12H,6,11H2,1H3,(H,13,14)/t10-/m0/s1

InChI Key

NHTGHBARYWONDQ-JTQLQIEISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

3-phenylpropanoic-acid
Alpha-amino acid
Alpha-amino acid or derivatives
Amphetamine or derivatives
D-alpha-amino acid
Phenylpropane
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Monocyclic benzene moiety
Benzenoid
Amino acid or derivatives
Amino acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Primary aliphatic amine
Organooxygen compound
Primary amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:6912 )
L-tyrosine derivative (CHEBI:6912 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Source

Exogenous

Exogenous (HMDB: HMDB0014903)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	312.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.48 g/L	Not Available
LogP	-1.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.48 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-1.1	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	2.06	ChemAxon
pKa (Strongest Basic)	9.93	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	83.55 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	51.81 m³·mol⁻¹	ChemAxon
Polarizability	19.9 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]+	145.433	31661259
DarkChem	[M-H]-	145.733	31661259
DeepCCS	[M+H]+	140.562	30932474
DeepCCS	[M-H]-	138.17	30932474
DeepCCS	[M-2H]-	173.25	30932474
DeepCCS	[M+Na]+	148.109	30932474
AllCCS	[M+H]+	143.1	32859911
AllCCS	[M+H-H2O]+	139.0	32859911
AllCCS	[M+NH4]+	146.9	32859911
AllCCS	[M+Na]+	148.0	32859911
AllCCS	[M-H]-	143.2	32859911
AllCCS	[M+Na-2H]-	144.0	32859911
AllCCS	[M+HCOO]-	144.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Metyrosine	C[C@](N)(CC1=CC=C(O)C=C1)C(O)=O	3174.7	Standard polar	33892256
Metyrosine	C[C@](N)(CC1=CC=C(O)C=C1)C(O)=O	1820.9	Standard non polar	33892256
Metyrosine	C[C@](N)(CC1=CC=C(O)C=C1)C(O)=O	2023.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Metyrosine,1TMS,isomer #1	C[C@](N)(CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O	1911.2	Semi standard non polar	33892256
Metyrosine,1TMS,isomer #2	C[C@](N)(CC1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C	1942.8	Semi standard non polar	33892256
Metyrosine,1TMS,isomer #3	C[C@@](CC1=CC=C(O)C=C1)(N[Si](C)(C)C)C(=O)O	2019.3	Semi standard non polar	33892256
Metyrosine,2TMS,isomer #1	C[C@](N)(CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C	1892.9	Semi standard non polar	33892256
Metyrosine,2TMS,isomer #2	C[C@@](CC1=CC=C(O[Si](C)(C)C)C=C1)(N[Si](C)(C)C)C(=O)O	1972.4	Semi standard non polar	33892256
Metyrosine,2TMS,isomer #3	C[C@@](CC1=CC=C(O)C=C1)(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	2003.8	Semi standard non polar	33892256
Metyrosine,2TMS,isomer #4	C[C@](CC1=CC=C(O)C=C1)(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2163.8	Semi standard non polar	33892256
Metyrosine,3TMS,isomer #1	C[C@@](CC1=CC=C(O[Si](C)(C)C)C=C1)(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1959.0	Semi standard non polar	33892256
Metyrosine,3TMS,isomer #1	C[C@@](CC1=CC=C(O[Si](C)(C)C)C=C1)(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1943.7	Standard non polar	33892256
Metyrosine,3TMS,isomer #1	C[C@@](CC1=CC=C(O[Si](C)(C)C)C=C1)(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	2054.2	Standard polar	33892256
Metyrosine,3TMS,isomer #2	C[C@](CC1=CC=C(O[Si](C)(C)C)C=C1)(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2149.5	Semi standard non polar	33892256
Metyrosine,3TMS,isomer #2	C[C@](CC1=CC=C(O[Si](C)(C)C)C=C1)(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2020.3	Standard non polar	33892256
Metyrosine,3TMS,isomer #2	C[C@](CC1=CC=C(O[Si](C)(C)C)C=C1)(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2276.4	Standard polar	33892256
Metyrosine,3TMS,isomer #3	C[C@](CC1=CC=C(O)C=C1)(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2137.3	Semi standard non polar	33892256
Metyrosine,3TMS,isomer #3	C[C@](CC1=CC=C(O)C=C1)(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2101.7	Standard non polar	33892256
Metyrosine,3TMS,isomer #3	C[C@](CC1=CC=C(O)C=C1)(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2227.9	Standard polar	33892256
Metyrosine,4TMS,isomer #1	C[C@](CC1=CC=C(O[Si](C)(C)C)C=C1)(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2169.9	Semi standard non polar	33892256
Metyrosine,4TMS,isomer #1	C[C@](CC1=CC=C(O[Si](C)(C)C)C=C1)(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2076.7	Standard non polar	33892256
Metyrosine,4TMS,isomer #1	C[C@](CC1=CC=C(O[Si](C)(C)C)C=C1)(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2048.3	Standard polar	33892256
Metyrosine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@](C)(N)C(=O)O)C=C1	2167.2	Semi standard non polar	33892256
Metyrosine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@](C)(N)CC1=CC=C(O)C=C1	2193.3	Semi standard non polar	33892256
Metyrosine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@](C)(CC1=CC=C(O)C=C1)C(=O)O	2248.4	Semi standard non polar	33892256
Metyrosine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@](C)(N)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2440.0	Semi standard non polar	33892256
Metyrosine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@](C)(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O	2509.5	Semi standard non polar	33892256
Metyrosine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@](C)(CC1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	2496.4	Semi standard non polar	33892256
Metyrosine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@](C)(CC1=CC=C(O)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2608.4	Semi standard non polar	33892256
Metyrosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@](C)(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	2687.2	Semi standard non polar	33892256
Metyrosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@](C)(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	2546.0	Standard non polar	33892256
Metyrosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@](C)(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	2418.9	Standard polar	33892256
Metyrosine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@](C)(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2884.6	Semi standard non polar	33892256
Metyrosine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@](C)(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2622.0	Standard non polar	33892256
Metyrosine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@](C)(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2543.8	Standard polar	33892256
Metyrosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@](C)(CC1=CC=C(O)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2813.5	Semi standard non polar	33892256
Metyrosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@](C)(CC1=CC=C(O)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2688.1	Standard non polar	33892256
Metyrosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@](C)(CC1=CC=C(O)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2489.9	Standard polar	33892256
Metyrosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@](C)(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3081.2	Semi standard non polar	33892256
Metyrosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@](C)(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2813.8	Standard non polar	33892256
Metyrosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@](C)(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2458.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Metyrosine GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-4900000000-946ec0a9cb27d9dde874	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metyrosine GC-MS (2 TMS) - 70eV, Positive	splash10-00fu-9651000000-11b1bed7129ec3e5c27a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metyrosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metyrosine 10V, Positive-QTOF	splash10-0udi-0900000000-7b2e7907b466193628f3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metyrosine 20V, Positive-QTOF	splash10-0udi-0900000000-8ee69272ff1683e7b679	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metyrosine 40V, Positive-QTOF	splash10-0a6r-3900000000-95f4506f225bff0a13e3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metyrosine 10V, Negative-QTOF	splash10-0006-3900000000-9aec0e31d6c52c6d4218	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metyrosine 20V, Negative-QTOF	splash10-000i-9500000000-ea5a5dcd5c96018a361e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metyrosine 40V, Negative-QTOF	splash10-0kac-7900000000-25650809bb77fee5eb83	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metyrosine 10V, Positive-QTOF	splash10-0ug1-0900000000-01322d7fad379ffae336	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metyrosine 20V, Positive-QTOF	splash10-053r-0900000000-0f9c6bd0ffbe22e32c94	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metyrosine 40V, Positive-QTOF	splash10-004i-9200000000-30cb5b9f46a657686267	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metyrosine 10V, Negative-QTOF	splash10-0f6x-1900000000-3caf5c634bee6695a462	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metyrosine 20V, Negative-QTOF	splash10-001i-3900000000-a9dda666c5606b501480	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metyrosine 40V, Negative-QTOF	splash10-0536-7900000000-2d7f96942196ae0b76e0	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00765	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00765	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00765

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

390103

KEGG Compound ID

C07921

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Metirosine

METLIN ID

Not Available

PubChem Compound

441350

PDB ID

Not Available

ChEBI ID

6912

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Tyrosine 3-monooxygenase

General function:: Involved in monooxygenase activity
Specific function:: Plays an important role in the physiology of adrenergic neurons.
Gene Name:: TH
Uniprot ID:: P07101
Molecular weight:: 55611.26

References

Nasrallah HA, Donnelly EF, Bigelow LB, Rivera-Calimlim L, Rogol A, Potkin S, Rauscher FP, Wyatt RJ: Inhibition of dopamine synthesis in chronic schizophrenia. Clinical ineffectiveness of metyrosine. Arch Gen Psychiatry. 1977 Jun;34(6):649-55. [PubMed:17374 ]
Yoshimoto Y, Nakaso K, Nakashima K: L-dopa and dopamine enhance the formation of aggregates under proteasome inhibition in PC12 cells. FEBS Lett. 2005 Feb 14;579(5):1197-202. Epub 2005 Jan 21. [PubMed:15710413 ]
Shore PA, Dorris RL: On a prime role for newly synthesized dopamine in striatal function. Eur J Pharmacol. 1975 Feb;30(2):315-8. [PubMed:1168577 ]
Moore KE, Demarest KT, Johnston CA: Influence of prolactin on dopaminergic neuronal systems in the hypothalamus. Fed Proc. 1980 Sep;39(11):2912-6. [PubMed:7409209 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Metyrosine (HMDB0014903)

MOL for HMDB0014903 (Metyrosine)

3D MOL for HMDB0014903 (Metyrosine)

3D SDF for HMDB0014903 (Metyrosine)

3D-SDF for HMDB0014903 (Metyrosine)

PDB for HMDB0014903 (Metyrosine)

3D PDB for HMDB0014903 (Metyrosine)

SMILES for HMDB0014903 (Metyrosine)

INCHI for HMDB0014903 (Metyrosine)

Structure for HMDB0014903 (Metyrosine)

3D Structure for HMDB0014903 (Metyrosine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

References