MiMeDB: Showing metabocard for o-Tyrosine (MMDBc0000613)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:51:08 UTC

Update Date

2024-04-30 19:33:17 UTC

Metabolite ID

MMDBc0000613

Metabolite Identification

Common Name

o-Tyrosine

Description

o-Tyrosine is a normal human metabolite. Its presence is possible due to the hydroxylation of l-phenylalanine by hydroxyl radical (*OH), and is proposed as an hydroxy radical biomarker of oxidative damage to proteins. o-Tyrosine might also be included in the diet and absorbed. It has been associated with disease such as Kwashiorkor, a severe form of protein-energy malnutrition. However, many publications mention that the results are inconclusive, and o-tyrosine is not selectively altered by antioxidant intervention, exercise training or age. (PMID:14670743 , 10969271 , 9887186 ).

Structure

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

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      30.061 -11.026   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      35.396  -6.406   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      32.729  -6.406   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      35.396  -9.486   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      32.729  -9.486   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      34.062  -8.716   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      32.729 -11.026   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      31.395 -11.796   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      34.062 -11.796   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      34.062  -7.176   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      31.395 -13.336   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      34.062 -13.336   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      32.729 -14.106   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2   10                                                            
CONECT    3   10                                                            
CONECT    4    6                                                            
CONECT    5    6    7                                                       
CONECT    6    4    5   10                                                  
CONECT    7    5    8    9                                                  
CONECT    8    1    7   11                                                  
CONECT    9    7   12                                                       
CONECT   10    2    3    6                                                  
CONECT   11    8   13                                                       
CONECT   12    9   13                                                       
CONECT   13   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

Synonyms

Value	Source
2-Amino-3-(2-hydroxyphenyl)propanoic acid	ChEBI
2-Amino-3-(2-hydroxyphenyl)propanoate	Generator
2-Hydroxy-DL-phenylalanine	HMDB
2-Hydroxy-phenylalanine	HMDB
2-Hydroxyphenylalanine	HMDB
2-Tyrosine	HMDB
3-(O-Hydroxyphenyl)DL-alanine	HMDB
DL- O-Tyrosine	HMDB
DL-3-(O-Hydroxyphenyl)alanine	HMDB
DL-O-Tyrosine	HMDB
Ortho-tyrosine	HMDB
2-Tyrosine, (D)-isomer	HMDB
2-Tyrosine, (DL)-isomer	HMDB
2-Tyrosine, (L)-isomer	HMDB

Molecular Formula

C₉H₁₁NO₃

Average Mass

181.1885

Monoisotopic Mass

181.073893223

IUPAC Name

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

Traditional Name

2-tyrosine

CAS Registry Number

Not Available

SMILES

NC(CC1=CC=CC=C1O)C(O)=O

InChI Identifier

InChI=1S/C9H11NO3/c10-7(9(12)13)5-6-3-1-2-4-8(6)11/h1-4,7,11H,5,10H2,(H,12,13)

InChI Key

WRFPVMFCRNYQNR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine 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

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
3-phenylpropanoic-acid
Amphetamine or derivatives
Alpha-amino acid
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Aralkylamine
Phenol
Monocyclic benzene moiety
Benzenoid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

an amino acid derivative (CPD-11757 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	5.57 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-1.5	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	2.01	ChemAxon
pKa (Strongest Basic)	8.88	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	47.1 m³·mol⁻¹	ChemAxon
Polarizability	17.76 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-4900000000-aa81f75d9ed4e977df68	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0a4i-5491000000-9a9969815e032107fc44	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-0900000000-ebb473b1eb9270c27a26	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-015i-0900000000-d3b4c59468db65e33b80	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00kf-9700000000-cf7cdfd040ca5a451fa2	2012-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0019-0900000000-01ee9c831970c7f79ede	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-04fdaa25b741b52c551e	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9300000000-639776ec42cd7c70b706	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1900000000-9911c42139ecbba3b834	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05fr-7900000000-b4167e456277ba9ec5ba	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fu-9200000000-159e5a860c481d106109	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00lr-0900000000-0789c3bec09b7b71842e	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0aor-2900000000-294b1d1404168e5de571	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05mo-9800000000-9ac4c7e756ac9d42572d	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00li-0900000000-1d0af1b840230361c6f8	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0aou-2900000000-66a3f07b95f44b6d0341	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-06c2ec0981d6e289ea4f	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	29291809

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected but not Quantified	NULL	NULL	Normal	HMDB	21543078
Human Feces	Detected but not Quantified	Adult (>18 years old)	Female	Normal	HMDB	26709303
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified				HMDB

External Links

HMDB ID

HMDB0247350

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023822

KNApSAcK ID

Not Available

Chemspider ID

82607

KEGG Compound ID

Not Available

BioCyc ID

CPD0-923

BiGG ID

Not Available

Wikipedia Link

Tyrosine

METLIN ID

Not Available

PubChem Compound

91482

PDB ID

Not Available

ChEBI ID

91038

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Leeuwenburgh C, Hansen PA, Holloszy JO, Heinecke JW: Oxidized amino acids in the urine of aging rats: potential markers for assessing oxidative stress in vivo. Am J Physiol. 1999 Jan;276(1):R128-35. doi: 10.1152/ajpregu.1999.276.1.R128. [PubMed:9887186 ]
Manary MJ, Leeuwenburgh C, Heinecke JW: Increased oxidative stress in kwashiorkor. J Pediatr. 2000 Sep;137(3):421-4. doi: 10.1067/mpd.2000.107512. [PubMed:10969271 ]
Orhan H, Vermeulen NP, Tump C, Zappey H, Meerman JH: Simultaneous determination of tyrosine, phenylalanine and deoxyguanosine oxidation products by liquid chromatography-tandem mass spectrometry as non-invasive biomarkers for oxidative damage. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Jan 25;799(2):245-54. doi: 10.1016/j.jchromb.2003.10.056. [PubMed:14670743 ]

Showing metabocard for o-Tyrosine (MMDBc0000613)

MOL for #<Metabolite:0x0000556b6b0125a8>

3D MOL for #<Metabolite:0x0000556b6b0125a8>

3D SDF for #<Metabolite:0x0000556b6b0125a8>

3D-SDF for #<Metabolite:0x0000556b6b0125a8>

PDB for #<Metabolite:0x0000556b6b0125a8>

3D PDB for #<Metabolite:0x0000556b6b0125a8>

SMILES for #<Metabolite:0x0000556b6b0125a8>

INCHI for #<Metabolite:0x0000556b6b0125a8>

Structure for #<Metabolite:0x0000556b6b0125a8>

3D Structure for #<Metabolite:0x0000556b6b0125a8>