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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-02-28 10:36:16 UTC

Update Date

2021-09-14 15:20:03 UTC

HMDB ID

HMDB0001885

Secondary Accession Numbers

HMDB01885

Metabolite Identification

Common Name

3-Chlorotyrosine

Description

3-Chlorotyrosine, a specific marker of myeloperoxidase-catalyzed oxidation, is markedly elevated in low density lipoprotein isolated from human atherosclerotic intima. (PMID 9151778 ). In particular, myeloperoxidase halogenates tyrosine residues in plasma proteins and and generates 3-chlorotyrosine (CY). The detection of free chlorotyrosine in blood or urine arises from the degradation of these chlorinated proteins. CY concentrations may be useful for monitoring the activation of neutrophils in asthmatic patients (PMID 15196282 ).

Structure

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

Untitled Document-1
  Mrv1652305261923562D          

 14 14  0  0  0  0            999 V2000
   -2.4750   -1.0717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750    0.3572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -1.0717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.3572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.0717    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12  7  1  0  0  0  0
 10 13  1  0  0  0  0
  9 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001885

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(CC1=CC(Cl)=C(O)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H10ClNO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14)

> <INCHI_KEY>
ACWBBAGYTKWBCD-UHFFFAOYSA-N

> <FORMULA>
C9H10ClNO3

> <MOLECULAR_WEIGHT>
215.634

> <EXACT_MASS>
215.034920898

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
20.351929982702742

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-(3-chloro-4-hydroxyphenyl)propanoic acid

> <ALOGPS_LOGP>
-1.65

> <JCHEM_LOGP>
-0.8850358142060988

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.922885095364729

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5613557553897812

> <JCHEM_PKA_STRONGEST_BASIC>
9.470030440170163

> <JCHEM_POLAR_SURFACE_AREA>
83.55

> <JCHEM_REFRACTIVITY>
51.90200000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
monochlorotyrosine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Untitled Document-1                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0      -4.620  -2.001   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -3.850  -0.667   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.620   0.667   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.310  -0.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.540   0.667   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -1.540  -2.001   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       0.000   0.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.770  -0.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.310  -0.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.080   0.667   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.310   2.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.770   2.001   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.620   0.667   0.000  0.00  0.00           O+0
HETATM   14 Cl   UNK     0       3.080  -2.001   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4    7                                                       
CONECT    6    4                                                            
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13   10                                                            
CONECT   14    9                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Chloro-L-tyrosine	HMDB
Chlorotyrosine	HMDB
L-(8CI)-3-chloro-tyrosine	HMDB
Monochlorotyrosine	HMDB
3-Chlorotyrosine, (L)-isomer	HMDB
3-Chlorotyrosine hydrochloride, (L)-isomer	HMDB
2-Amino-3-(3-chloro-4-hydroxyphenyl)propanoate	HMDB

Chemical Formula

C₉H₁₀ClNO₃

Average Molecular Weight

215.634

Monoisotopic Molecular Weight

215.034920898

IUPAC Name

2-amino-3-(3-chloro-4-hydroxyphenyl)propanoic acid

Traditional Name

monochlorotyrosine

CAS Registry Number

7423-93-0

SMILES

NC(CC1=CC(Cl)=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C9H10ClNO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14)

InChI Key

ACWBBAGYTKWBCD-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
2-chlorophenol
2-halophenol
1-hydroxy-2-unsubstituted benzenoid
Halobenzene
Chlorobenzene
Phenol
Aralkylamine
Aryl halide
Benzenoid
Aryl chloride
Monocyclic benzene moiety
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Organohalogen compound
Primary aliphatic amine
Organochloride
Organonitrogen compound
Organooxygen compound
Primary amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Circulatory system disorder

Cardiac disorder

Myocardial infarction (HMDB: HMDB0001885)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17512353)

Cell

Leukocyte (HMDB: HMDB0001885)

Excreta

Biofluid or Excreta

Urine (PMID: 15196282)

Cellular substructure

Cytoplasm (HMDB: HMDB0001885)

Source

Endogenous

Endogenous (HMDB: HMDB0001885)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Asthma (HMDB: HMDB0001885)

Role

Industrial application

Pharmaceutical industry

Biomarker

Asthma (MarkerDB: MDB00000351)

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

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.01 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-0.89	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	1.56	ChemAxon
pKa (Strongest Basic)	9.47	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	51.9 m³·mol⁻¹	ChemAxon
Polarizability	20.35 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
AllCCS	[M+H]+	145.962	32859911
AllCCS	[M-H]-	143.181	32859911
DeepCCS	[M+H]+	140.287	30932474
DeepCCS	[M-H]-	136.85	30932474
DeepCCS	[M-2H]-	173.807	30932474
DeepCCS	[M+Na]+	149.345	30932474
AllCCS	[M+H]+	146.0	32859911
AllCCS	[M+H-H2O]+	142.0	32859911
AllCCS	[M+NH4]+	149.6	32859911
AllCCS	[M+Na]+	150.7	32859911
AllCCS	[M-H]-	143.2	32859911
AllCCS	[M+Na-2H]-	143.9	32859911
AllCCS	[M+HCOO]-	144.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Chlorotyrosine	NC(CC1=CC(Cl)=C(O)C=C1)C(O)=O	3198.8	Standard polar	33892256
3-Chlorotyrosine	NC(CC1=CC(Cl)=C(O)C=C1)C(O)=O	1991.9	Standard non polar	33892256
3-Chlorotyrosine	NC(CC1=CC(Cl)=C(O)C=C1)C(O)=O	1964.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Chlorotyrosine,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CC(N)C(=O)O)C=C1Cl	2047.1	Semi standard non polar	33892256
3-Chlorotyrosine,1TMS,isomer #2	C[Si](C)(C)OC(=O)C(N)CC1=CC=C(O)C(Cl)=C1	1927.1	Semi standard non polar	33892256
3-Chlorotyrosine,1TMS,isomer #3	C[Si](C)(C)NC(CC1=CC=C(O)C(Cl)=C1)C(=O)O	1984.3	Semi standard non polar	33892256
3-Chlorotyrosine,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(N)CC1=CC=C(O[Si](C)(C)C)C(Cl)=C1	2021.9	Semi standard non polar	33892256
3-Chlorotyrosine,2TMS,isomer #2	C[Si](C)(C)NC(CC1=CC=C(O[Si](C)(C)C)C(Cl)=C1)C(=O)O	2061.6	Semi standard non polar	33892256
3-Chlorotyrosine,2TMS,isomer #3	C[Si](C)(C)NC(CC1=CC=C(O)C(Cl)=C1)C(=O)O[Si](C)(C)C	1956.1	Semi standard non polar	33892256
3-Chlorotyrosine,2TMS,isomer #4	C[Si](C)(C)N(C(CC1=CC=C(O)C(Cl)=C1)C(=O)O)[Si](C)(C)C	2139.3	Semi standard non polar	33892256
3-Chlorotyrosine,3TMS,isomer #1	C[Si](C)(C)NC(CC1=CC=C(O[Si](C)(C)C)C(Cl)=C1)C(=O)O[Si](C)(C)C	2047.5	Semi standard non polar	33892256
3-Chlorotyrosine,3TMS,isomer #1	C[Si](C)(C)NC(CC1=CC=C(O[Si](C)(C)C)C(Cl)=C1)C(=O)O[Si](C)(C)C	2066.9	Standard non polar	33892256
3-Chlorotyrosine,3TMS,isomer #1	C[Si](C)(C)NC(CC1=CC=C(O[Si](C)(C)C)C(Cl)=C1)C(=O)O[Si](C)(C)C	2197.2	Standard polar	33892256
3-Chlorotyrosine,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1Cl	2225.7	Semi standard non polar	33892256
3-Chlorotyrosine,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1Cl	2143.0	Standard non polar	33892256
3-Chlorotyrosine,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1Cl	2373.8	Standard polar	33892256
3-Chlorotyrosine,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(CC1=CC=C(O)C(Cl)=C1)N([Si](C)(C)C)[Si](C)(C)C	2142.2	Semi standard non polar	33892256
3-Chlorotyrosine,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(CC1=CC=C(O)C(Cl)=C1)N([Si](C)(C)C)[Si](C)(C)C	2130.7	Standard non polar	33892256
3-Chlorotyrosine,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(CC1=CC=C(O)C(Cl)=C1)N([Si](C)(C)C)[Si](C)(C)C	2325.6	Standard polar	33892256
3-Chlorotyrosine,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C)C(Cl)=C1)N([Si](C)(C)C)[Si](C)(C)C	2263.1	Semi standard non polar	33892256
3-Chlorotyrosine,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C)C(Cl)=C1)N([Si](C)(C)C)[Si](C)(C)C	2202.8	Standard non polar	33892256
3-Chlorotyrosine,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C)C(Cl)=C1)N([Si](C)(C)C)[Si](C)(C)C	2158.5	Standard polar	33892256
3-Chlorotyrosine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CC(N)C(=O)O)C=C1Cl	2292.7	Semi standard non polar	33892256
3-Chlorotyrosine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(N)CC1=CC=C(O)C(Cl)=C1	2197.6	Semi standard non polar	33892256
3-Chlorotyrosine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(CC1=CC=C(O)C(Cl)=C1)C(=O)O	2255.4	Semi standard non polar	33892256
3-Chlorotyrosine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(N)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(Cl)=C1	2544.7	Semi standard non polar	33892256
3-Chlorotyrosine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(Cl)=C1)C(=O)O	2600.2	Semi standard non polar	33892256
3-Chlorotyrosine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(CC1=CC=C(O)C(Cl)=C1)C(=O)O[Si](C)(C)C(C)(C)C	2439.1	Semi standard non polar	33892256
3-Chlorotyrosine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C(CC1=CC=C(O)C(Cl)=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2574.4	Semi standard non polar	33892256
3-Chlorotyrosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(Cl)=C1)C(=O)O[Si](C)(C)C(C)(C)C	2807.4	Semi standard non polar	33892256
3-Chlorotyrosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(Cl)=C1)C(=O)O[Si](C)(C)C(C)(C)C	2691.2	Standard non polar	33892256
3-Chlorotyrosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(Cl)=C1)C(=O)O[Si](C)(C)C(C)(C)C	2570.0	Standard polar	33892256
3-Chlorotyrosine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1Cl	2943.0	Semi standard non polar	33892256
3-Chlorotyrosine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1Cl	2742.0	Standard non polar	33892256
3-Chlorotyrosine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1Cl	2648.4	Standard polar	33892256
3-Chlorotyrosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O)C(Cl)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2800.9	Semi standard non polar	33892256
3-Chlorotyrosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O)C(Cl)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2746.9	Standard non polar	33892256
3-Chlorotyrosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O)C(Cl)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2595.2	Standard polar	33892256
3-Chlorotyrosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(Cl)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3165.1	Semi standard non polar	33892256
3-Chlorotyrosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(Cl)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2941.3	Standard non polar	33892256
3-Chlorotyrosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(Cl)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2586.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Chlorotyrosine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-4900000000-c69773ca1577b5149033	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Chlorotyrosine GC-MS (2 TMS) - 70eV, Positive	splash10-006x-9551000000-ae9ee1bced5f2211d2c6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Chlorotyrosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Chlorotyrosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Chlorotyrosine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Chlorotyrosine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Chlorotyrosine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Chlorotyrosine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Chlorotyrosine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Chlorotyrosine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Chlorotyrosine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Chlorotyrosine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Chlorotyrosine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Chlorotyrosine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Chlorotyrosine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Chlorotyrosine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Chlorotyrosine GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-03	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-Chlorotyrosine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-01b9-0970000000-69b92cf990ab75e60cd9	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Chlorotyrosine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-00di-0900000000-efa66d19cc56269a53f2	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Chlorotyrosine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-003i-0900000000-d47f0bce2c489e27a354	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Chlorotyrosine 10V, Positive-QTOF	splash10-00di-0900000000-87217a1412566be24da9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Chlorotyrosine 20V, Positive-QTOF	splash10-00dr-0900000000-dae748b289c1e6116ce1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Chlorotyrosine 40V, Positive-QTOF	splash10-003i-4900000000-f3432f54f8baa6410135	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Chlorotyrosine 20V, Positive-QTOF	splash10-05gi-0900000000-31e3ad885494620cd5e7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Chlorotyrosine 40V, Negative-QTOF	splash10-000i-9300000000-03ca45ea8b987214f17e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Chlorotyrosine 10V, Positive-QTOF	splash10-00di-0900000000-71323d2fd7f1009df049	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Chlorotyrosine 40V, Positive-QTOF	splash10-003l-5900000000-15bb19b70f8df303c8b5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Chlorotyrosine 10V, Negative-QTOF	splash10-03dj-1970000000-9e6a8919711cd6c66943	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Chlorotyrosine 20V, Negative-QTOF	splash10-014i-1900000000-6cfece7111fafd3c3f68	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chlorotyrosine 10V, Positive-QTOF	splash10-00xs-0930000000-bf8bb76dcd41eaae17b7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chlorotyrosine 20V, Positive-QTOF	splash10-00di-0900000000-73207308b5015b532d84	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chlorotyrosine 40V, Positive-QTOF	splash10-01ox-1900000000-0207fc9d2438bcc14490	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chlorotyrosine 10V, Negative-QTOF	splash10-03di-0390000000-2d17d72b84125bbf4529	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chlorotyrosine 20V, Negative-QTOF	splash10-03ka-1950000000-51d2b9fa36efbd91b16b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chlorotyrosine 40V, Negative-QTOF	splash10-00di-8900000000-26312333ed317f499326	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chlorotyrosine 10V, Negative-QTOF	splash10-03di-3390000000-9f599b58715e5e4112c4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chlorotyrosine 20V, Negative-QTOF	splash10-00di-9310000000-c0e0710e12f760e22787	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chlorotyrosine 40V, Negative-QTOF	splash10-0089-9100000000-dc1f3da8ed37d54aa528	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chlorotyrosine 10V, Positive-QTOF	splash10-00xr-0960000000-aef407ba4424f751016e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chlorotyrosine 20V, Positive-QTOF	splash10-00di-0900000000-6a43a80631ee697e2ffd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chlorotyrosine 40V, Positive-QTOF	splash10-0fai-2900000000-c17c4101c57449acbc9d	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Leukocyte

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	6.96 +/- 3.578 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	0.0007 +/- 0.0005 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	15196282	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.58 +/- 0.18 uM	Adult (>18 years old)	Both	Myocardial infarction	17512353	details
Urine	Detected and Quantified	10.886 +/- 8.573 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	0.0023 +/- 0.0016 umol/mmol creatinine	Adult (>18 years old)	Both	Asthma	15196282	details

Associated Disorders and Diseases

Disease References

Myocardial infarction
Mocatta TJ, Pilbrow AP, Cameron VA, Senthilmohan R, Frampton CM, Richards AM, Winterbourn CC: Plasma concentrations of myeloperoxidase predict mortality after myocardial infarction. J Am Coll Cardiol. 2007 May 22;49(20):1993-2000. Epub 2007 May 4. [PubMed:17512353 ]
Asthma
Mita H, Higashi N, Taniguchi M, Higashi A, Kawagishi Y, Akiyama K: Urinary 3-bromotyrosine and 3-chlorotyrosine concentrations in asthmatic patients: lack of increase in 3-bromotyrosine concentration in urine and plasma proteins in aspirin-induced asthma after intravenous aspirin challenge. Clin Exp Allergy. 2004 Jun;34(6):931-8. [PubMed:15196282 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

600807 (Asthma)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022723

KNApSAcK ID

Not Available

Chemspider ID

106510

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6369

PubChem Compound

119226

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000351

Good Scents ID

Not Available

References

Synthesis Reference

Bouchilloux, Simone. Chlorination of L-tyrosine. Bulletin de la Societe de Chimie Biologique (1955), 37 255-8.

Material Safety Data Sheet (MSDS)

Not Available

General References

Gaut JP, Byun J, Tran HD, Heinecke JW: Artifact-free quantification of free 3-chlorotyrosine, 3-bromotyrosine, and 3-nitrotyrosine in human plasma by electron capture-negative chemical ionization gas chromatography mass spectrometry and liquid chromatography-electrospray ionization tandem mass spectrometry. Anal Biochem. 2002 Jan 15;300(2):252-9. [PubMed:11779118 ]
Jasin HE: Oxidative modification of inflammatory synovial fluid immunoglobulin G. Inflammation. 1993 Apr;17(2):167-81. [PubMed:8387962 ]
Lamb NJ, Quinlan GJ, Westerman ST, Gutteridge JM, Evans TW: Nitration of proteins in bronchoalveolar lavage fluid from patients with acute respiratory distress syndrome receiving inhaled nitric oxide. Am J Respir Crit Care Med. 1999 Sep;160(3):1031-4. [PubMed:10471637 ]
Rosen H, Crowley JR, Heinecke JW: Human neutrophils use the myeloperoxidase-hydrogen peroxide-chloride system to chlorinate but not nitrate bacterial proteins during phagocytosis. J Biol Chem. 2002 Aug 23;277(34):30463-8. Epub 2002 Jun 11. [PubMed:12060654 ]
Kettle AJ: Detection of 3-chlorotyrosine in proteins exposed to neutrophil oxidants. Methods Enzymol. 1999;300:111-20. [PubMed:9919515 ]
Buss IH, Senthilmohan R, Darlow BA, Mogridge N, Kettle AJ, Winterbourn CC: 3-Chlorotyrosine as a marker of protein damage by myeloperoxidase in tracheal aspirates from preterm infants: association with adverse respiratory outcome. Pediatr Res. 2003 Mar;53(3):455-62. [PubMed:12595594 ]
Khan J, Brennand DM, Bradley N, Gao B, Bruckdorfer R, Jacobs M: 3-Nitrotyrosine in the proteins of human plasma determined by an ELISA method. Biochem J. 1998 Mar 1;330 ( Pt 2):795-801. [PubMed:9480893 ]
Mita H, Higashi N, Taniguchi M, Higashi A, Kawagishi Y, Akiyama K: Urinary 3-bromotyrosine and 3-chlorotyrosine concentrations in asthmatic patients: lack of increase in 3-bromotyrosine concentration in urine and plasma proteins in aspirin-induced asthma after intravenous aspirin challenge. Clin Exp Allergy. 2004 Jun;34(6):931-8. [PubMed:15196282 ]
Hazen SL, Heinecke JW: 3-Chlorotyrosine, a specific marker of myeloperoxidase-catalyzed oxidation, is markedly elevated in low density lipoprotein isolated from human atherosclerotic intima. J Clin Invest. 1997 May 1;99(9):2075-81. [PubMed:9151778 ]

Showing metabocard for 3-Chlorotyrosine (HMDB0001885)

MOL for HMDB0001885 (3-Chlorotyrosine)

3D MOL for HMDB0001885 (3-Chlorotyrosine)

3D SDF for HMDB0001885 (3-Chlorotyrosine)

3D-SDF for HMDB0001885 (3-Chlorotyrosine)

PDB for HMDB0001885 (3-Chlorotyrosine)

3D PDB for HMDB0001885 (3-Chlorotyrosine)

SMILES for HMDB0001885 (3-Chlorotyrosine)

INCHI for HMDB0001885 (3-Chlorotyrosine)

Structure for HMDB0001885 (3-Chlorotyrosine)

3D Structure for HMDB0001885 (3-Chlorotyrosine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra