| Record Information |
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| Version | 2.0 |
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| Created at | 2005-11-16 15:48:42 UTC |
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| Updated at | 2022-01-09 19:25:59 UTC |
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| NP-MRD ID | NP0000377 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | L-Tyrosine |
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| Description | Tyrosine (Tyr) or L-tyrosine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-tyrosine is one of 20 proteinogenic amino acids, i.E., The amino acids used in the biosynthesis of proteins. Tyrosine is found in all organisms ranging from bacteria to plants to animals. It is classified as a non-polar, uncharged (at physiological pH) aromatic amino acid. Tyrosine is a non-essential amino acid, meaning the body can synthesize it – usually from phenylalanine. The conversion of phenylalanine to tyrosine is catalyzed by the enzyme phenylalanine hydroxylase, a monooxygenase. This enzyme catalyzes the reaction causing the addition of a hydroxyl group to the end of the 6-carbon aromatic ring of phenylalanine, such that it becomes tyrosine. Tyrosine is found in many high-protein food products such as chicken, turkey, fish, milk, yogurt, cottage cheese, cheese, peanuts, almonds, pumpkin seeds, sesame seeds, soy products, lima beans, avocados and bananas. Tyrosine is one of the few amino acids that readily passes the blood-brain barrier. Once in the brain, it is a precursor for the neurotransmitters dopamine, norepinephrine and epinephrine, better known as adrenalin. These neurotransmitters are an important part of the body's sympathetic nervous system, and their concentrations in the body and brain are directly dependent upon dietary tyrosine. Tyrosine is not found in large concentrations throughout the body, probably because it is rapidly metabolized. Folic acid, copper and vitamin C are cofactor nutrients of these reactions. Tyrosine is also the precursor for hormones, including thyroid hormones (diiodotyrosine), catecholestrogens and the major human pigment, melanin. Tyrosine is an important amino acid in many proteins, peptides and even enkephalins, the body's natural pain reliever. Valine and other branched amino acids, and possibly tryptophan and phenylalanine may reduce tyrosine absorption. A number of genetic errors of tyrosine metabolism have been identified, such as hawkinsinuria and tyrosinemia I. The most common feature of these diseases is the increased amount of tyrosine in the blood, which is marked by decreased motor activity, lethargy and poor feeding. Infection and intellectual deficits may occur. Vitamin C supplements can help reverse these disease symptoms. Some adults also develop elevated tyrosine in their blood. This typically indicates a need for more vitamin C. More tyrosine is needed under stress, and tyrosine supplements prevent the stress-induced depletion of norepinephrine and can help aleviate biochemical depression. However, tyrosine may not be good for treating psychosis. Many antipsychotic medications apparently function by inhibiting tyrosine metabolism. L-Dopa, which is directly used in Parkinson's, is made from tyrosine. Tyrosine, the nutrient, can be used as an adjunct in the treatment of Parkinson's. Peripheral metabolism of tyrosine necessitates large doses of tyrosine, however, compared to L-Dopa (http://Www.Dcnutrition.Com). In addition to its role as a precursor for neurotransmitters, tyrosine plays an important role for the function of many proteins. Within many proteins or enzymes, certain tyrosine residues can be tagged (at the hydroxyl group) with a phosphate group (phosphorylated) by specialized protein kinases. In its phosphorylated form, tyrosine is called phosphotyrosine. Tyrosine phosphorylation is considered to be one of the key steps in signal transduction and regulation of enzymatic activity. Tyrosine (or its precursor phenylalanine) is also needed to synthesize the benzoquinone structure which forms part of coenzyme Q10. |
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| Structure | N[C@@H](CC1=CC=C(O)C=C1)C(O)=O InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1 |
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| Synonyms | | Value | Source |
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| (-)-alpha-Amino-p-hydroxyhydrocinnamic acid | ChEBI | | (2S)-2-Amino-3-(4-hydroxyphenyl)propanoic acid | ChEBI | | (S)-(-)-Tyrosine | ChEBI | | (S)-2-Amino-3-(p-hydroxyphenyl)propionic acid | ChEBI | | (S)-3-(p-Hydroxyphenyl)alanine | ChEBI | | (S)-alpha-Amino-4-hydroxybenzenepropanoic acid | ChEBI | | (S)-Tyrosine | ChEBI | | 4-Hydroxy-L-phenylalanine | ChEBI | | L-Tyrosin | ChEBI | | Tyr | ChEBI | | TYROSINE | ChEBI | | Y | ChEBI | | (-)-a-Amino-p-hydroxyhydrocinnamate | Generator | | (-)-a-Amino-p-hydroxyhydrocinnamic acid | Generator | | (-)-alpha-Amino-p-hydroxyhydrocinnamate | Generator | | (-)-Α-amino-p-hydroxyhydrocinnamate | Generator | | (-)-Α-amino-p-hydroxyhydrocinnamic acid | Generator | | (2S)-2-Amino-3-(4-hydroxyphenyl)propanoate | Generator | | (S)-2-Amino-3-(p-hydroxyphenyl)propionate | Generator | | (S)-a-Amino-4-hydroxybenzenepropanoate | Generator | | (S)-a-Amino-4-hydroxybenzenepropanoic acid | Generator | | (S)-alpha-Amino-4-hydroxybenzenepropanoate | Generator | | (S)-Α-amino-4-hydroxybenzenepropanoate | Generator | | (S)-Α-amino-4-hydroxybenzenepropanoic acid | Generator | | (S)-a-Amino-4-hydroxy-benzenepropanoate | HMDB | | (S)-a-Amino-4-hydroxy-benzenepropanoic acid | HMDB | | (S)-alpha-Amino-4-hydroxy-benzenepropanoate | HMDB | | (S)-alpha-Amino-4-hydroxy-benzenepropanoic acid | HMDB | | 2-Amino-3-(4-hydroxyphen yl)-2-amino-3-(4-hydroxyphenyl)-propanoate | HMDB | | 2-Amino-3-(4-hydroxyphen yl)-2-amino-3-(4-hydroxyphenyl)-propanoic acid | HMDB | | 3-(4-Hydroxyphenyl)-L-alanine | HMDB | | Benzenepropanoate | HMDB | | Benzenepropanoic acid | HMDB | | L-p-Tyrosine | HMDB | | p-Tyrosine | HMDB | | L Tyrosine | HMDB | | Tyrosine, L-isomer | HMDB | | Tyrosine, L isomer | HMDB | | Para tyrosine | HMDB | | Para-tyrosine | HMDB |
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| Chemical Formula | C9H11NO3 |
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| Average Mass | 181.1885 Da |
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| Monoisotopic Mass | 181.07389 Da |
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| IUPAC Name | (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid |
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| Traditional Name | L-tyrosine |
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| CAS Registry Number | 60-18-4 |
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| SMILES | N[C@@H](CC1=CC=C(O)C=C1)C(O)=O |
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| InChI Identifier | InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1 |
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| InChI Key | OUYCCCASQSFEME-QMMMGPOBSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, simulated) | Ahselim | | | 2022-01-09 | View Spectrum | | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, simulated) | varshavi.d26@gmail.com | Not Available | Not Available | 2021-08-01 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, simulated) | varshavi.d26@gmail.com | Not Available | Not Available | 2021-08-01 | View Spectrum |
| | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Amino acids, peptides, and analogues |
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| Direct Parent | Tyrosine and derivatives |
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| Alternative Parents | |
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| Substituents | - Tyrosine or derivatives
- Phenylalanine or derivatives
- 3-phenylpropanoic-acid
- Alpha-amino acid
- Amphetamine or derivatives
- L-alpha-amino acid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Aralkylamine
- Monocyclic benzene moiety
- Benzenoid
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Amine
- Primary aliphatic amine
- Organic nitrogen compound
- Carbonyl group
- Organopnictogen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Primary amine
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 343 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 0.48 mg/mL | Not Available | | LogP | -2.26 | Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995). |
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| Predicted Properties | |
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| General References | - Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [PubMed:12097436 ]
- Nicholson JK, O'Flynn MP, Sadler PJ, Macleod AF, Juul SM, Sonksen PH: Proton-nuclear-magnetic-resonance studies of serum, plasma and urine from fasting normal and diabetic subjects. Biochem J. 1984 Jan 15;217(2):365-75. [PubMed:6696735 ]
- Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. [PubMed:12834252 ]
- Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. [PubMed:9849813 ]
- Eklundh T, Eriksson M, Sjoberg S, Nordin C: Monoamine precursors, transmitters and metabolites in cerebrospinal fluid: a prospective study in healthy male subjects. J Psychiatr Res. 1996 May-Jun;30(3):201-8. [PubMed:8884658 ]
- Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. [PubMed:6198473 ]
- Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. [PubMed:15911239 ]
- Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. [PubMed:12297216 ]
- Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. [PubMed:14992292 ]
- Deng C, Shang C, Hu Y, Zhang X: Rapid diagnosis of phenylketonuria and other aminoacidemias by quantitative analysis of amino acids in neonatal blood spots by gas chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Jul 25;775(1):115-20. [PubMed:12101068 ]
- Flamen P, Bernheim N, Deron P, Caveliers V, Chavatte K, Franken PR, Bossuyt A: Iodine-123 alpha-methyl-l-tyrosine single-photon emission tomography for the visualization of head and neck squamous cell carcinomas. Eur J Nucl Med. 1998 Feb;25(2):177-81. [PubMed:9473267 ]
- Ishiwata K, Tsukada H, Kubota K, Nariai T, Harada N, Kawamura K, Kimura Y, Oda K, Iwata R, Ishii K: Preclinical and clinical evaluation of O-[11C]methyl-L-tyrosine for tumor imaging by positron emission tomography. Nucl Med Biol. 2005 Apr;32(3):253-62. [PubMed:15820760 ]
- Wannemacher RW Jr, Klainer AS, Dinterman RE, Beisel WR: The significance and mechanism of an increased serum phenylalanine-tyrosine ratio during infection. Am J Clin Nutr. 1976 Sep;29(9):997-1006. [PubMed:822705 ]
- Molnar GA, Wagner Z, Marko L, Ko Szegi T, Mohas M, Kocsis B, Matus Z, Wagner L, Tamasko M, Mazak I, Laczy B, Nagy J, Wittmann I: Urinary ortho-tyrosine excretion in diabetes mellitus and renal failure: evidence for hydroxyl radical production. Kidney Int. 2005 Nov;68(5):2281-7. [PubMed:16221230 ]
- Molnar GA, Nemes V, Biro Z, Ludany A, Wagner Z, Wittmann I: Accumulation of the hydroxyl free radical markers meta-, ortho-tyrosine and DOPA in cataractous lenses is accompanied by a lower protein and phenylalanine content of the water-soluble phase. Free Radic Res. 2005 Dec;39(12):1359-66. [PubMed:16298866 ]
- Hoffhines AJ, Damoc E, Bridges KG, Leary JA, Moore KL: Detection and purification of tyrosine-sulfated proteins using a novel anti-sulfotyrosine monoclonal antibody. J Biol Chem. 2006 Dec 8;281(49):37877-87. Epub 2006 Oct 17. [PubMed:17046811 ]
- Dowlati Y, Ravindran AV, Maheux M, Steiner M, Stewart DE, Meyer JH: No effect of oral tyrosine on total tyrosine levels in breast milk: implications for dietary supplementation in early postpartum. Arch Womens Ment Health. 2014 Dec;17(6):541-8. doi: 10.1007/s00737-014-0441-8. [PubMed:25015680 ]
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