3-(4-Hydroxyphenyl)pyruvate (BioDeep_00000897613)
代谢物信息卡片
化学式: C9H7O4- (179.0344322)
中文名称:
谱图信息:
最多检出来源 Viridiplantae(plant) 55.1%
分子结构信息
SMILES: C1=CC(=CC=C1CC(=O)C(=O)[O-])O
InChI: InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)/p-1
描述信息
A 2-oxo monocarboxylic acid anion obtained by removal of a proton from the carboxylic acid group of 3-(4-hydroxyphenyl)pyruvic acid.
COVID info from COVID-19 Disease Map
Corona-virus
Coronavirus
SARS-CoV-2
COVID-19
SARS-CoV
COVID19
SARS2
SARS
同义名列表
1 个代谢物同义名
数据库引用编号
分类词条
相关代谢途径
Reactome(0)
BioCyc(8)
PlantCyc(4)
代谢反应
20 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(10)
- tyrosine degradation II:
4-hydroxyphenylpyruvate + H+ + O2 ⟶ 4-hydroxyphenylacetate + CO2 + H2O
- tyrosine degradation I:
2-oxoglutarate + tyr ⟶ 4-hydroxyphenylpyruvate + glt
- L-tyrosine degradation III:
4-tyrosol + NAD+ ⟶ (4-hydroxyphenyl)acetaldehyde + H+ + NADH
- (S)-reticuline biosynthesis I:
3-(4-hydroxyphenyl)pyruvate + H+ ⟶ (4-hydroxyphenyl)acetaldehyde + CO2
- tyrosine degradation:
pyruvate + tyr ⟶ 4-hydroxyphenylpyruvate + ala
- tyrosine degradation III:
4-hydroxyphenylpyruvate + ala ⟶ pyruvate + tyr
- tyrosine degradation III:
pyruvate + tyr ⟶ 4-hydroxyphenylpyruvate + ala
- L-tyrosine degradation II:
3-(4-hydroxyphenyl)pyruvate + O2 ⟶ (4-hydroxyphenyl)acetate + CO2
- factor 420 biosynthesis:
4-hydroxyphenylpyruvate + ARP + H2O + SAM ⟶ 5'-deoxyadenosine + 7,8-didemethyl-8-hydroxy-5-deazariboflavin + H+ + ammonium + met + oxalate
- factor 420 biosynthesis:
4-hydroxyphenylpyruvate + ARP + H2O + SAM ⟶ 5'-deoxyadenosine + 7,8-didemethyl-8-hydroxy-5-deazariboflavin + H+ + ammonium + met + oxalate
Plant Reactome(0)
INOH(0)
PlantCyc(9)
- (S)-reticuline biosynthesis I:
(6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2 + tyramine ⟶ (6R)-4a-hydroxy-tetrahydrobiopterin + dopamine
- (S)-reticuline biosynthesis I:
(6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2 + tyramine ⟶ (6R)-4a-hydroxy-tetrahydrobiopterin + dopamine
- 4-hydroxy-4-methyl-L-glutamate biosynthesis:
4-hydroxy-4-methyl-2-oxoglutarate ⟶ pyruvate
- 4-hydroxy-4-methyl-L-glutamate biosynthesis:
4-hydroxy-4-methyl-2-oxoglutarate ⟶ pyruvate
- Organic Nitrogen Assimilation:
H+ + H2O + adenine ⟶ ammonium + hypoxanthine
- Organic Nitrogen Assimilation:
H+ + H2O + adenine ⟶ ammonium + hypoxanthine
- Organic Nitrogen Assimilation:
H+ + H2O + adenine ⟶ ammonium + hypoxanthine
- Organic Nitrogen Assimilation:
H+ + H2O + adenine ⟶ ammonium + hypoxanthine
- Organic Nitrogen Assimilation:
NAD+ + glu ⟶ 2-oxoglutarate + H+ + NADH + gln
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
0 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
- Anne Jahn, Maike Petersen. Hydroxy(phenyl)pyruvic acid reductase in Actaea racemosa L.: a putative enzyme in cimicifugic and fukinolic acid biosynthesis.
Planta.
2024 Mar; 259(5):102. doi:
10.1007/s00425-024-04382-6
. [PMID: 38549005] - Huan Lu, Yingze Liu, Mengshuo Li, Heping Han, Fengyan Zhou, Alex Nyporko, Qin Yu, Sheng Qiang, Stephen Powles. Multiple Metabolic Enzymes Can Be Involved in Cross-Resistance to 4-Hydroxyphenylpyruvate-Dioxygenase-Inhibiting Herbicides in Wild Radish.
Journal of agricultural and food chemistry.
2023 Jun; 71(24):9302-9313. doi:
10.1021/acs.jafc.3c01231
. [PMID: 37170102] - Jia-Xu Nan, Jing-Fang Yang, Hong-Yan Lin, Yao-Chao Yan, Shao-Meng Zhou, Xue-Fang Wei, Qiong Chen, Wen-Chao Yang, Ren-Yu Qu, Guang-Fu Yang. Synthesis and Herbicidal Activity of Triketone-Aminopyridines as Potent p-Hydroxyphenylpyruvate Dioxygenase Inhibitors.
Journal of agricultural and food chemistry.
2021 May; 69(20):5734-5745. doi:
10.1021/acs.jafc.0c07782
. [PMID: 33999624] - S L Curtis, B P Norman, A M Milan, J A Gallagher, B Olsson, L R Ranganath, N B Roberts. Interference of hydroxyphenylpyruvic acid, hydroxyphenyllactic acid and tyrosine on routine serum and urine clinical chemistry assays; implications for biochemical monitoring of patients with alkaptonuria treated with nitisinone.
Clinical biochemistry.
2019 Sep; 71(?):24-30. doi:
10.1016/j.clinbiochem.2019.06.010
. [PMID: 31228435] - Guo-Quan Wang, Jun-Feng Chen, Bo Yi, He-Xin Tan, Lei Zhang, Wan-Sheng Chen. HPPR encodes the hydroxyphenylpyruvate reductase required for the biosynthesis of hydrophilic phenolic acids in Salvia miltiorrhiza.
Chinese journal of natural medicines.
2017 Dec; 15(12):917-927. doi:
10.1016/s1875-5364(18)30008-6
. [PMID: 29329649] - Ying Fu, Yi-Na Sun, Ke-Han Yi, Ming-Qiang Li, Hai-Feng Cao, Jia-Zhong Li, Fei Ye. 3D Pharmacophore-Based Virtual Screening and Docking Approaches toward the Discovery of Novel HPPD Inhibitors.
Molecules (Basel, Switzerland).
2017 Jun; 22(6):. doi:
10.3390/molecules22060959
. [PMID: 28598377] - Minmin Wang, Kyoko Toda, Hiroshi A Maeda. Biochemical properties and subcellular localization of tyrosine aminotransferases in Arabidopsis thaliana.
Phytochemistry.
2016 Dec; 132(?):16-25. doi:
10.1016/j.phytochem.2016.09.007
. [PMID: 27726859] - Daniel P Killeen, Lesley Larsen, Franck E Dayan, Keith C Gordon, Nigel B Perry, John W van Klink. Nortriketones: Antimicrobial Trimethylated Acylphloroglucinols from Ma̅nuka (Leptospermum scoparium).
Journal of natural products.
2016 Mar; 79(3):564-9. doi:
10.1021/acs.jnatprod.5b00968
. [PMID: 26731565] - Valeria A Kostevich, Alexey V Sokolov, Natalia A Grudinina, Elena T Zakharova, Valeria R Samygina, Vadim B Vasilyev. Interaction of macrophage migration inhibitory factor with ceruloplasmin: role of labile copper ions.
Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine.
2015 Oct; 28(5):817-26. doi:
10.1007/s10534-015-9868-2
. [PMID: 26091949] - Ilya Gertsman, Jon A Gangoiti, William L Nyhan, Bruce A Barshop. Perturbations of tyrosine metabolism promote the indolepyruvate pathway via tryptophan in host and microbiome.
Molecular genetics and metabolism.
2015 Mar; 114(3):431-7. doi:
10.1016/j.ymgme.2015.01.005
. [PMID: 25680927] - Matthew A Bedewitz, Elsa Góngora-Castillo, Joseph B Uebler, Eliana Gonzales-Vigil, Krystle E Wiegert-Rininger, Kevin L Childs, John P Hamilton, Brieanne Vaillancourt, Yun-Soo Yeo, Joseph Chappell, Dean DellaPenna, A Daniel Jones, C Robin Buell, Cornelius S Barry. A root-expressed L-phenylalanine:4-hydroxyphenylpyruvate aminotransferase is required for tropane alkaloid biosynthesis in Atropa belladonna.
The Plant cell.
2014 Sep; 26(9):3745-62. doi:
10.1105/tpc.114.130534
. [PMID: 25228340] - Ruy J Cruz, Tomoyuki Harada, Eizaburo Sasatomi, Mitchell P Fink. Effects of ethyl pyruvate and other α-keto carboxylic acid derivatives in a rat model of multivisceral ischemia and reperfusion.
The Journal of surgical research.
2011 Jan; 165(1):151-7. doi:
10.1016/j.jss.2009.07.008
. [PMID: 19959189] - James Cartwright, Richard M Green. Tyrosine-derived 4-hydroxyphenylpyruvate reacts with ketone test fields of 3 commercially available urine dipsticks.
Veterinary clinical pathology.
2010 Sep; 39(3):354-7. doi:
10.1111/j.1939-165x.2010.00231.x
. [PMID: 20487432] - Ju Qian, Liu Guiping, Liu Xiujun, Han Xincai, Liu Hongmei. Influence of growth regulators and sucrose concentrations on growth and rosmarinic acid production in calli and suspension cultures of Coleus blumei.
Natural product research.
2009; 23(2):127-37. doi:
10.1080/14786410801890338
. [PMID: 19173121] - Hyung-Doo Park, Dong Hwan Lee, Tae-Youn Choi, You Kyoung Lee, Jong-Won Kim, Chang-Seok Ki, Yong-Wha Lee. Clinical, biochemical, and genetic analysis of a Korean neonate with hereditary tyrosinemia type 1.
Clinical chemistry and laboratory medicine.
2009; 47(8):930-3. doi:
10.1515/cclm.2009.223
. [PMID: 19569981] - Jihad T Al-Ratrout, Mohammed Al-Muzian, Mona Al-Nazer, Naseem A Ansari. Plantar keratoderma: a manifestation of tyrosinemia type II (Richner-Hanhart syndrome).
Annals of Saudi medicine.
2005 Sep; 25(5):422-4. doi:
10.5144/0256-4947.2005.422
. [PMID: 16270769] - R E Williams, E A Lock. D-serine-induced nephrotoxicity: possible interaction with tyrosine metabolism.
Toxicology.
2004 Sep; 201(1-3):231-8. doi:
10.1016/j.tox.2004.05.001
. [PMID: 15297036] - F Wu, M Fu, X Wei, W Yang, R Hu, L Guo. [Fluorescence quenching method for the determination of p-hydroxyphenylpyruvic acid].
Guang pu xue yu guang pu fen xi = Guang pu.
2001 Jun; 21(3):359-61. doi:
. [PMID: 12947668]
- A El Sawalhy, J R Seed, J E Hall, H El Attar. Increased excretion of aromatic amino acid catabolites in animals infected with Trypanosoma brucei evansi.
The Journal of parasitology.
1998 Jun; 84(3):469-73. doi:
. [PMID: 9645841]
- Kh K Karshiev. [Effects of ultraviolet irradiation of blood and sodium hypochlorite on aromatic amino acid metabolism in phlegmons of the maxillofacial region].
Vestnik khirurgii imeni I. I. Grekova.
1998; 157(6):72-3. doi:
NULL
. [PMID: 10672668] - J C Deutsch. Determination of p-hydroxyphenylpyruvate, p-hydroxyphenyllactate and tyrosine in normal human plasma by gas chromatography-mass spectrometry isotope-dilution assay.
Journal of chromatography. B, Biomedical sciences and applications.
1997 Mar; 690(1-2):1-6. doi:
10.1016/s0378-4347(96)00411-2
. [PMID: 9106023] - G A Mitchell. Inhibition of 4-hydroxyphenylpyruvate dioxygenase by 2-(2-nitro-4-trifluoromethylbenzoyl)-cyclohexane-1,3-dione and 2-(2-chloro-4-methanesulfonylbenzoyl)-cyclohexane-1,3-dione.
Human & experimental toxicology.
1996 Feb; 15(2):179-81. doi:
10.1177/096032719601500209
. [PMID: 8645506] - M K Ellis, A C Whitfield, L A Gowans, T R Auton, W M Provan, E A Lock, L L Smith. Inhibition of 4-hydroxyphenylpyruvate dioxygenase by 2-(2-nitro-4-trifluoromethylbenzoyl)-cyclohexane-1,3-dione and 2-(2-chloro-4-methanesulfonylbenzoyl)-cyclohexane-1,3-dione.
Toxicology and applied pharmacology.
1995 Jul; 133(1):12-9. doi:
10.1006/taap.1995.1121
. [PMID: 7597701] - M Borden, J Holm, J Leslie, L Sweetman, W L Nyhan, L Fleisher, H Nadler, D Lewis, C R Scott. Hawkinsinuria in two families.
American journal of medical genetics.
1992 Sep; 44(1):52-6. doi:
10.1002/ajmg.1320440113
. [PMID: 1519651] - G Y Wu, J R Thompson. The effect of glutamine on protein turnover in chick skeletal muscle in vitro.
The Biochemical journal.
1990 Jan; 265(2):593-8. doi:
10.1042/bj2650593
. [PMID: 2302190] - Kh Kurbanov, N A Spiridonova. [Tyrosine and methionine metabolism in various states of melaninogenesis].
Biokhimiia (Moscow, Russia).
1990 Jan; 55(1):165-72. doi:
. [PMID: 1971518]
- E Mönch, J Kneer, C Jakobs, M Arnold, H Diehl, U Batzler. Examination of urine metabolites in the newborn period and during protein loading tests at 6 months of age--Part 1.
European journal of pediatrics.
1990; 149 Suppl 1(?):S17-24. doi:
10.1007/bf02126294
. [PMID: 2091926] - T O Frommel, J R Seed, J Sechelski. Changes in albumin levels in blood and urine of Microtus montanus chronically infected with Trypanosoma brucei gambiense.
The Journal of parasitology.
1988 Dec; 74(6):957-62. doi:
NULL
. [PMID: 3057169] - A G Antoshechkin, L A Zuyeva, L A Maximova. Excretion of phenylpyruvic, 4-hydroxyphenylpyruvic and indolyl-3-acetic acids by the skin fibroblasts from a phenylketonuric child.
Journal of inherited metabolic disease.
1988; 11(3):299-301. doi:
10.1007/bf01800373
. [PMID: 3148072] - M Matsuo, K Saiki, J Tanabe, H Nakamura, T Matsuo. Citrullinaemia: an infantile form with p-hydroxyphenylpyruvic and p-hydroxyphenyllactic acidurias.
Journal of inherited metabolic disease.
1987; 10(3):276. doi:
10.1007/bf01800080
. [PMID: 3123792] - J E Hall, J R Seed. Increased urinary excretion of aromatic amino acid catabolites by Microtus montanus chronically infected with Trypanosoma brucei gambiense.
Comparative biochemistry and physiology. B, Comparative biochemistry.
1984; 77(4):755-60. doi:
10.1016/0305-0491(84)90309-2
. [PMID: 6375946] - N Furukawa, T Hayano, N Sato, F Inoue, Y Machida, A Kinugasa, S Imashuku, T Kusunoki, T Takamatisu. The enzyme defects in hereditary tyrosinaemia type I.
Journal of inherited metabolic disease.
1984; 7 Suppl 2(?):137-8. doi:
10.1007/978-94-009-5612-4_43
. [PMID: 6434869] - M Yanaka, J Okumura. Effects of dietary protein level and ascorbic acid supplementation on the contents of tyrosine metabolites in droppings and plasma of chicks fed a diet containing excess tyrosine.
Poultry science.
1983 Dec; 62(12):2433-41. doi:
10.3382/ps.0622433
. [PMID: 6689445] - H Machino, Y Miki, T Kawatsu, K Kida, H Matsuda. Successful dietary control of tyrosinemia II.
Journal of the American Academy of Dermatology.
1983 Oct; 9(4):533-9. doi:
10.1016/s0190-9622(83)70165-9
. [PMID: 6195199] - F Endo, A Kitano, I Uehara, N Nagata, I Matsuda, T Shinka, T Kuhara, I Matsumoto. Four-hydroxyphenylpyruvic acid oxidase deficiency with normal fumarylacetoacetase: a new variant form of hereditary hypertyrosinemia.
Pediatric research.
1983 Feb; 17(2):92-6. doi:
10.1203/00006450-198302000-00002
. [PMID: 6828337] - J R Seed, J E Hall, C C Price. A physiological mechanism to explain pathogenesis in African trypanosomiasis.
Contributions to microbiology and immunology.
1983; 7(?):83-94. doi:
NULL
. [PMID: 6337778] - P Sampathkumar, J F Morrison. Chorismate mutase-prephenate dehydrogenase from Escherichia coli. Kinetic mechanism of the prephenate dehydrogenase reaction.
Biochimica et biophysica acta.
1982 Apr; 702(2):212-9. doi:
10.1016/0167-4838(82)90505-2
. [PMID: 7044425] - J R Seed, J E Hall, J Sechelski. Phenylalanine metabolism in Microtus montanus chronically infected with Trypanosoma brucei gambiense.
Comparative biochemistry and physiology. B, Comparative biochemistry.
1982; 71(2):209-15. doi:
10.1016/0305-0491(82)90242-5
. [PMID: 7037281] - P Riederer, G P Reynolds. Determination of a wide range of urinary amine metabolites using a simple high-performance liquid chromatographic technique.
Journal of chromatography.
1981 Sep; 225(1):179-84. doi:
10.1016/s0378-4347(00)80257-1
. [PMID: 6170650] - B M Nordlinger, J T Fulenwider, B A Faraj, R A Bethel, D Rudman. Tyrosine metabolism in cirrhosis: acquired alkaptonuria.
Surgical forum.
1978; 29(?):442-4. doi:
NULL
. [PMID: 401217] - S A Fernbach, R E Summons, W E Pereira, A M Duffield. Metabolic studies of transient tyrosinemia in premature infants.
Pediatric research.
1975 Apr; 9(4):172-6. doi:
10.1203/00006450-197504000-00006
. [PMID: 1143952] - W E KNOX, M LeMAY-KNOX. The oxidation in liver of l-tyrosine to acetoacetate through p-hydroxyphenylpyruvate and homogentisic acid.
The Biochemical journal.
1951 Oct; 49(5):686-93. doi:
10.1042/bj0490686
. [PMID: 14886367] - . .
.
. doi:
. [PMID: 15284489]