o-Tyrosine (BioDeep_00000017742)
human metabolite Endogenous blood metabolite Volatile Flavor Compounds
代谢物信息卡片
化学式: C9H11NO3 (181.0738896)
中文名称: L-2-羟基苯丙氨酸, DL-邻酪氨酸, DL-o-酪氨酸
谱图信息:
最多检出来源 Homo sapiens(feces) 6.04%
分子结构信息
SMILES: C1=CC=C(C(=C1)CC(C(=O)O)N)O
InChI: 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)
描述信息
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) [HMDB]
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).
同义名列表
17 个代谢物同义名
2-Amino-3-(2-hydroxyphenyl)propanoic acid; 2-Amino-3-(2-hydroxyphenyl)propanoate; DL-3-(O-Hydroxyphenyl)alanine; 3-(O-Hydroxyphenyl)DL-alanine; 2-Hydroxy-DL-phenylalanine; Phenylalanine, 2-hydroxy-; 2-Hydroxy-phenylalanine; 2-Tyrosine, (DL)-isomer; 2-Tyrosine, (L)-isomer; 2-Tyrosine, (D)-isomer; 2-Hydroxyphenylalanine; DL- O-Tyrosine; Ortho-tyrosine; DL-o-Tyrosine; 2-Tyrosine; o-Tyrosine; DL-o-Tyrosine
数据库引用编号
15 个数据库交叉引用编号
- ChEBI: CHEBI:89461
- ChEBI: CHEBI:91038
- PubChem: 91482
- HMDB: HMDB0006050
- ChEMBL: CHEMBL107813
- Wikipedia: Tyrosine
- MetaCyc: CPD0-923
- foodb: FDB023822
- chemspider: 82607
- CAS: 2370-61-8
- CAS: 709-16-0
- PMhub: MS000000009
- RefMet: 2-Hydroxyphenylalanine
- PubChem: 6950574
- RefMet: o-Tyrosine
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Angus Lindsay, Preston M McCourt, Peter Karachunski, Dawn A Lowe, James M Ervasti. Xanthine oxidase is hyper-active in Duchenne muscular dystrophy.
Free radical biology & medicine.
2018 12; 129(?):364-371. doi:
10.1016/j.freeradbiomed.2018.10.404. [PMID: 30312761] - Lívia Szélig, Szilárd Kun, Gábor Woth, Gergő A Molnár, Zita Zrínyi, Emese Kátai, János Lantos, István Wittmann, Lajos Bogár, Attila Miseta, Csaba Csontos. Time courses of changes of para-, meta-, and ortho-tyrosine in septic patients: A pilot study.
Redox report : communications in free radical research.
2016 Jul; 21(4):180-9. doi:
10.1179/1351000215y.0000000028. [PMID: 26193242] - Szilárd Kun, Esztella Mikolás, Gergo A Molnár, Eszter Sélley, Boglárka Laczy, Botond Csiky, Tibor Kovács, István Wittmann. Association of plasma ortho-tyrosine/para-tyrosine ratio with responsiveness of erythropoiesis-stimulating agent in dialyzed patients.
Redox report : communications in free radical research.
2014 Sep; 19(5):190-8. doi:
10.1179/1351000214y.0000000090. [PMID: 24693974] - Nasser Zare, Reza Farjaminezhad, Rasool Asghari-Zakaria, Manoochehr Farjaminezhad. Enhanced thebaine production in Papaver bracteatum cell suspension culture by combination of elicitation and precursor feeding.
Natural product research.
2014; 28(10):711-7. doi:
10.1080/14786419.2013.878936. [PMID: 24499458] - Raúl A Ruggiero, Juan Bruzzo, Paula Chiarella, Oscar D Bustuoabad, Roberto P Meiss, Christiane D Pasqualini. Concomitant tumor resistance: the role of tyrosine isomers in the mechanisms of metastases control.
Cancer research.
2012 Mar; 72(5):1043-50. doi:
10.1158/0008-5472.can-11-2964. [PMID: 22315349] - Raúl A Ruggiero, Juan Bruzzo, Paula Chiarella, Pedro di Gianni, Martín A Isturiz, Susana Linskens, Norma Speziale, Roberto P Meiss, Oscar D Bustuoabad, Christiane D Pasqualini. Tyrosine isomers mediate the classical phenomenon of concomitant tumor resistance.
Cancer research.
2011 Nov; 71(22):7113-24. doi:
10.1158/0008-5472.can-11-0581. [PMID: 22084446] - Pál Brasnyó, Gergo A Molnár, Márton Mohás, Lajos Markó, Boglárka Laczy, Judit Cseh, Esztella Mikolás, István András Szijártó, Akos Mérei, Richárd Halmai, László G Mészáros, Balázs Sümegi, István Wittmann. Resveratrol improves insulin sensitivity, reduces oxidative stress and activates the Akt pathway in type 2 diabetic patients.
The British journal of nutrition.
2011 Aug; 106(3):383-9. doi:
10.1017/s0007114511000316. [PMID: 21385509] - Alberto Plaza, Giuseppe Bifulco, Milena Masullo, John R Lloyd, Jessica L Keffer, Patrick L Colin, John N A Hooper, Lori J Bell, Carole A Bewley. Mutremdamide A and koshikamides C-H, peptide inhibitors of HIV-1 entry from different Theonella species.
The Journal of organic chemistry.
2010 Jul; 75(13):4344-55. doi:
10.1021/jo100076g. [PMID: 20402515] - Rønnaug Solberg, Jannicke H Andresen, Raquel Escrig, Maximo Vento, Ola Didrik Saugstad. Resuscitation of hypoxic newborn piglets with oxygen induces a dose-dependent increase in markers of oxidation.
Pediatric research.
2007 Nov; 62(5):559-63. doi:
10.1203/pdr.0b013e318156e8aa. [PMID: 18049371] - Chutima Matayatsuk, Anne Poljak, Sonia Bustamante, George A Smythe, Ruchaneekorn W Kalpravidh, Pornpan Sirankapracha, Suthat Fucharoen, Prapin Wilairat. Quantitative determination of ortho- and meta-tyrosine as biomarkers of protein oxidative damage in beta-thalassemia.
Redox report : communications in free radical research.
2007; 12(5):219-28. doi:
10.1179/135100007x200272. [PMID: 17925094] - Gergõ A Molnár, Zoltán Wagner, Lajos Markó, Tamás Kó Szegi, Márton Mohás, Béla Kocsis, Zoltán Matus, László Wagner, Mónika Tamaskó, István Mazák, Boglárka Laczy, Judit Nagy, István Wittmann. Urinary ortho-tyrosine excretion in diabetes mellitus and renal failure: evidence for hydroxyl radical production.
Kidney international.
2005 Nov; 68(5):2281-7. doi:
10.1111/j.1523-1755.2005.00687.x. [PMID: 16221230] - P Dandona, P Mohanty, W Hamouda, H Ghanim, A Aljada, R Garg, V Kumar. Inhibitory effect of a two day fast on reactive oxygen species (ROS) generation by leucocytes and plasma ortho-tyrosine and meta-tyrosine concentrations.
The Journal of clinical endocrinology and metabolism.
2001 Jun; 86(6):2899-902. doi:
10.1210/jcem.86.6.7745. [PMID: 11397907] - E A Kirk, J W Heinecke, R C LeBoeuf. Iron overload diminishes atherosclerosis in apoE-deficient mice.
The Journal of clinical investigation.
2001 Jun; 107(12):1545-53. doi:
10.1172/jci7664. [PMID: 11413162] - S Pennathur, J D Wagner, C Leeuwenburgh, K N Litwak, J W Heinecke. A hydroxyl radical-like species oxidizes cynomolgus monkey artery wall proteins in early diabetic vascular disease.
The Journal of clinical investigation.
2001 Apr; 107(7):853-60. doi:
10.1172/jci11194. [PMID: 11285304] - M J Manary, C Leeuwenburgh, J W Heinecke. Increased oxidative stress in kwashiorkor.
The Journal of pediatrics.
2000 Sep; 137(3):421-4. doi:
10.1067/mpd.2000.107512. [PMID: 10969271] - C H Magsino, W Hamouda, V Bapna, H Ghanim, I A Abu-Reish, A Aljada, P Dandona. Nadolol inhibits reactive oxygen species generation by leukocytes and linoleic acid oxidation.
The American journal of cardiology.
2000 Aug; 86(4):443-8. doi:
10.1016/s0002-9149(00)00962-0. [PMID: 10946040] - C H Magsino, W Hamouda, H Ghanim, R Browne, A Aljada, P Dandona. Effect of triiodothyronine on reactive oxygen species generation by leukocytes, indices of oxidative damage, and antioxidant reserve.
Metabolism: clinical and experimental.
2000 Jun; 49(6):799-803. doi:
10.1053/meta.2000.6263. [PMID: 10877210] - C Leeuwenburgh, P Hansen, A Shaish, J O Holloszy, J W Heinecke. Markers of protein oxidation by hydroxyl radical and reactive nitrogen species in tissues of aging rats.
The American journal of physiology.
1998 02; 274(2):R453-61. doi:
10.1152/ajpregu.1998.274.2.r453. [PMID: 9486304] - B Lubec, J Golej, M Marx, M Weninger, H Hoeger. L-arginine reduces kidney lipid peroxidation, glycoxidation and collagen accumulation in the aging NMRI mouse.
Renal physiology and biochemistry.
1995 Mar; 18(2):97-102. doi:
10.1159/000173905. [PMID: 7539539] - L R Karam, D S Bergtold, M G Simic. Biomarkers of OH radical damage in vivo.
Free radical research communications.
1991; 12-13 Pt 1(?):11-6. doi:
10.3109/10715769109145762. [PMID: 1649078] - S Ishimitsu, S Fujimoto, A Ohara. High-performance liquid chromatographic determination of m-tyrosine and o-tyrosine in rat urine.
Journal of chromatography.
1989 Apr; 489(2):377-83. doi:
10.1016/s0378-4347(00)82917-5. [PMID: 2753962]