Homogentisic acid (BioDeep_00000001653)

 

Secondary id: BioDeep_00000400106, BioDeep_00000400430, BioDeep_00000412634

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Chemicals and Drugs Toxin BioNovoGene_Lab2019


代谢物信息卡片


2-(2,5-dihydroxyphenyl)acetic acid

化学式: C8H8O4 (168.0423)
中文名称: 高龙胆酸, 尿黑酸
谱图信息: 最多检出来源 Homo sapiens(plant) 19.64%

Reviewed

Last reviewed on 2024-07-25.

Cite this Page

Homogentisic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/homogentisic_acid (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000001653). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1=CC(=C(C=C1O)CC(=O)O)O
InChI: InChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)

描述信息

Homogentisic acid, also known as melanic acid, is an intermediate in the breakdown or catabolism of tyrosine and phenylalanine. It is generated from the compound p-hydroxyphenylpyruvate through the enzyme p-hydroxyphenylpyruvate dehydrogenase. The resulting homogentisic acid is then broken down into 4-maleylacetoacetate via the enzyme homogentisate 1,2-dioxygenase. Homogentisic acid is also found in other organisms. For instance, it can found in Arbutus unedo (strawberry-tree) honey, in the bacterial plant pathogen Xanthomonas campestris as well as in the yeast Yarrowia lipolytica where it is associated with the production of brown pigments. Homogentisic acid can be oxidatively dimerized to form hipposudoric acid, one of the main constituents of the blood sweat of hippopotamuses. When present in sufficiently high levels, homogentisic acid can function as an osteotoxin and a renal toxin. An osteotoxin is a substance that causes damage to bones and/or joints. A renal toxin causes damage to the kidneys. Chronically high levels of homogentisic acid are associated with alkaptonuria (OMIM: 203500), an inborn error of metabolism. Alkaptonuria is a rare inherited genetic disorder in which the body cannot process the amino acids phenylalanine and tyrosine. It is caused by a mutation in the enzyme homogentisate 1,2-dioxygenase (EC 1.13.11.5), which leads to an accumulation of homogentisic acid in the blood and tissues. Homogentisic acid and its oxidized form benzoquinone acetic acid are excreted in the urine, giving it an unusually dark color. The accumulating homogentisic acid (and benzoquinone acetic acid) causes damage to cartilage (ochronosis, leading to osteoarthritis) and heart valves as well as precipitating as kidney stones and stones in other organs. More specifically, homogentisic acid can be converted to benzoquinone acetic acid (BQA), and the resulting BQA can be readily converted to polymers that resemble the dark skin pigment melanin. These polymers are deposited in the collagen, a connective tissue protein, of particular tissues such as cartilage. This process is called ochronosis (as the tissue looks ochre); ochronotic tissue is stiffened and unusually brittle, impairing its normal function and causing damage. Homogentisic acid is the primary precursor of melanin synthesis in Vibrio cholerae.
2-(3,6-dihydroxyphenyl)acetic acid, also known as homogentisic acid or homogentisate, is a member of the class of compounds known as 2(hydroxyphenyl)acetic acids. 2(hydroxyphenyl)acetic acids are phenylacetic acids that carry a hydroxyl group at the 2-position. 2-(3,6-dihydroxyphenyl)acetic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 2-(3,6-dihydroxyphenyl)acetic acid can be found in a number of food items such as gooseberry, angelica, chinese broccoli, and cucumber, which makes 2-(3,6-dihydroxyphenyl)acetic acid a potential biomarker for the consumption of these food products. 2-(3,6-dihydroxyphenyl)acetic acid can be found primarily in blood, feces, and urine, as well as in human cartilage, connective tissue and kidney tissues. In humans, 2-(3,6-dihydroxyphenyl)acetic acid is involved in few metabolic pathways, which include disulfiram action pathway, phenylalanine and tyrosine metabolism, and tyrosine metabolism. 2-(3,6-dihydroxyphenyl)acetic acid is also involved in several metabolic disorders, some of which include dopamine beta-hydroxylase deficiency, tyrosinemia type 3 (TYRO3), alkaptonuria, and tyrosinemia type 2 (or richner-hanhart syndrome). Moreover, 2-(3,6-dihydroxyphenyl)acetic acid is found to be associated with alkaptonuria. 2-(3,6-dihydroxyphenyl)acetic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Apart from treatment of the complications (such as pain relief using NSAIDs and joint replacement for the cartilage damage), vitamin C has been used to reduce the ochronosis and lowering of the homogentisic acid levels may be attempted with a low-protein diet. Recently the drug nitisinone has been found to suppress homogentisic acid production. Nitrisinone inhibits the enzyme, 4-hydroxyphenylpyruvate dioxygenase, responsible for converting tyrosine to homogentisic acid, thereby blocking the production and accumulation of homogentisic acid. Nitisinone treatment has been shown to cause a 95\\\\% reduction in plasma and urinary homogentisic acid (T3DB).
Acquisition and generation of the data is financially supported in part by CREST/JST.
CONFIDENCE standard compound; INTERNAL_ID 118
KEIO_ID H060
Homogentisic acid is a specific metabolite in urine and serum, which is used for diagnosis of alkaptonuria.
Homogentisic acid is a specific metabolite in urine and serum, which is used for diagnosis of alkaptonuria.

同义名列表

24 个代谢物同义名

2-(2,5-dihydroxyphenyl)acetic acid; 2-(3,6-DIHYDROXYPHENYL)acetIC ACID; (2,5-Dihydroxyphenyl)-acetic acid; 2,5-Dihydroxy-benzeneacetic acid; 2,5-Dihydroxy-alpha-toluic acid; 2-(3,6-DIHYDROXYPHENYL)acetate; 2,5-Dihydroxyphenylacetic acid; (2,5-Dihydroxyphenyl)-acetate; 2,5-Dihydroxy-benzeneacetate; 2,5-Dihydroxy-alpha-toluate; 2,5-Dihydroxy-a-toluic acid; 2,5-Dihydroxyphenylacetate; 2,5-Dihydroxy-a-toluate; Homogentisinic acid; Acid, homogentisic; Homogentisate acid; Homogentisic acid; Homogentisinate; Homogentisate; Melanic acid; Alcapton; Homogentisic acid; Homogentisate; Homogentisic acid



数据库引用编号

35 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

40 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(39)

PharmGKB(0)

44 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。

亚细胞结构定位 关联基因列表
Cytoplasm 11 CAT, DAO, FDPS, GGPS1, GSTZ1, HPD, NFE2L2, SNCA, TH, TYR, VIM
Peripheral membrane protein 3 DAO, HPD, HSD17B6
Endosome membrane 1 TF
Endoplasmic reticulum membrane 1 HPD
Nucleus 3 NFE2L2, SNCA, TH
cytosol 13 CAT, DAO, FAH, FDPS, GGPS1, GSTZ1, HPD, NFE2L2, PAH, SNCA, TAT, TH, VIM
dendrite 2 GLRA1, TH
phagocytic vesicle 1 VIM
centrosome 1 NFE2L2
nucleoplasm 4 FDPS, GGPS1, NFE2L2, UTP25
RNA polymerase II transcription regulator complex 1 NFE2L2
Cell membrane 3 DAO, GLRA1, VIM
Cell projection, axon 2 SNCA, TH
Early endosome membrane 1 HSD17B6
Multi-pass membrane protein 1 GLRA1
Golgi apparatus membrane 1 HPD
Synapse 2 GLRA1, SNCA
cell cortex 1 SNCA
cell surface 2 TF, TNR
glutamatergic synapse 1 TNR
Golgi apparatus 2 NFE2L2, SI
Golgi membrane 1 HPD
growth cone 1 SNCA
neuronal cell body 2 GLRA1, SNCA
postsynapse 2 GLRA1, SNCA
smooth endoplasmic reticulum 1 TH
synaptic vesicle 1 TH
Cytoplasm, cytosol 2 DAO, NFE2L2
Lysosome 2 SNCA, TYR
plasma membrane 7 DAO, GLRA1, NFE2L2, SI, SNCA, TF, VIM
presynaptic active zone 1 DAO
synaptic vesicle membrane 1 SNCA
terminal bouton 1 TH
Membrane 5 CAT, FDPS, GLRA1, SI, SNCA
apical plasma membrane 2 SI, TF
axon 3 SNCA, TH, VIM
brush border 1 SI
extracellular exosome 7 CAT, DAO, FAH, HPD, SI, TF, VIM
Lumenal side 1 HSD17B6
endoplasmic reticulum 1 HSD17B6
extracellular space 4 DAO, SNCA, TF, TNR
perinuclear region of cytoplasm 5 GGPS1, SNCA, TF, TH, TYR
Schaffer collateral - CA1 synapse 1 TNR
bicellular tight junction 1 DAO
mitochondrion 4 CAT, GSTZ1, SNCA, TH
protein-containing complex 2 CAT, SNCA
intracellular membrane-bounded organelle 4 CAT, GLRA1, HSD17B6, TYR
Microsome membrane 1 HSD17B6
Single-pass type I membrane protein 1 TYR
Secreted 3 DAO, SNCA, TF
extracellular region 5 CAT, DAO, SNCA, TF, TNR
cytoplasmic side of plasma membrane 1 TH
basal part of cell 1 TF
mitochondrial matrix 3 CAT, FDPS, GSTZ1
Extracellular side 1 DAO
external side of plasma membrane 1 GLRA1
Secreted, extracellular space, extracellular matrix 1 TNR
actin cytoskeleton 1 SNCA
perikaryon 2 GLRA1, TH
Z disc 1 GGPS1
cytoplasmic vesicle 2 TF, TH
nucleolus 1 UTP25
Melanosome membrane 2 TH, TYR
Early endosome 1 TF
clathrin-coated pit 1 TF
Golgi-associated vesicle 1 TYR
recycling endosome 1 TF
vesicle 1 TF
postsynaptic membrane 1 GLRA1
Cytoplasm, perinuclear region 2 GGPS1, TH
Membrane raft 1 TNR
Cytoplasm, cytoskeleton 1 VIM
focal adhesion 2 CAT, VIM
Peroxisome 4 CAT, DAO, FDPS, VIM
Peroxisome matrix 2 CAT, DAO
peroxisomal matrix 2 CAT, DAO
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 1 TNR
intermediate filament 1 VIM
Postsynaptic cell membrane 1 GLRA1
Late endosome 1 TF
neuron projection 3 GLRA1, TH, VIM
chromatin 1 NFE2L2
mediator complex 1 NFE2L2
cell leading edge 1 VIM
cell projection 2 DAO, GLRA1
supramolecular fiber 1 SNCA
cytoskeleton 1 VIM
Secreted, extracellular space 1 DAO
Nucleus, nucleolus 1 UTP25
blood microparticle 1 TF
transmembrane transporter complex 1 GLRA1
chloride channel complex 1 GLRA1
microtubule organizing center 1 VIM
Cell projection, dendrite 1 GLRA1
Melanosome 1 TYR
intermediate filament cytoskeleton 1 VIM
Cytoplasm, myofibril, sarcomere, Z line 1 GGPS1
basal plasma membrane 1 TF
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 2 CAT, TF
HFE-transferrin receptor complex 1 TF
endoplasmic reticulum lumen 1 TF
nuclear matrix 1 VIM
axon terminus 1 SNCA
specific granule lumen 1 DAO
endocytic vesicle 1 TF
small-subunit processome 1 UTP25
perineuronal net 1 TNR
Nucleus matrix 1 VIM
clathrin-coated endocytic vesicle membrane 1 TF
protein-DNA complex 1 NFE2L2
inhibitory synapse 1 GLRA1
vesicle coat 1 TF
catalase complex 1 CAT
inclusion body 1 SNCA
glycinergic synapse 1 GLRA1
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle 1 TH
tenascin complex 1 TNR
dense body 1 TF


文献列表

  • Andreja Jurič, Ana Huđek Turković, Irena Brčić Karačonji, Saša Prđun, Dragan Bubalo, Ksenija Durgo. Cytotoxic activity of strawberry tree (Arbutus unedo L.) honey, its extract, and homogentisic acid on CAL 27, HepG2, and Caco-2 cell lines. Arhiv za higijenu rada i toksikologiju. 2022 Jul; 73(2):158-168. doi: 10.2478/aiht-2022-73-3653. [PMID: 35792769]
  • A K Annamalai, M Gurnell. Black urine-alkaptonuria. QJM : monthly journal of the Association of Physicians. 2022 06; 115(6):397-398. doi: 10.1093/qjmed/hcac098. [PMID: 35394539]
  • Saifei Liu, Liyang Xie, Jiaxuan Su, Binnian Tian, Anfei Fang, Yang Yu, Chaowei Bi, Yuheng Yang. Integrated Metabolo-transcriptomics Reveals the Defense Response of Homogentisic Acid in Wheat against Puccinia striiformis f. sp. tritici. Journal of agricultural and food chemistry. 2022 Mar; 70(12):3719-3729. doi: 10.1021/acs.jafc.2c00231. [PMID: 35293725]
  • Andrea Soltysova, Alexandr Kuzin, Elena Samarkina, Andrea Zatkova. Alkaptonuria in Russia. European journal of human genetics : EJHG. 2022 02; 30(2):237-242. doi: 10.1038/s41431-021-00955-1. [PMID: 34504318]
  • Andrea Bernini, Elena Petricci, Andrea Atrei, Maria Camilla Baratto, Fabrizio Manetti, Annalisa Santucci. A molecular spectroscopy approach for the investigation of early phase ochronotic pigment development in Alkaptonuria. Scientific reports. 2021 11; 11(1):22562. doi: 10.1038/s41598-021-01670-z. [PMID: 34799606]
  • Camille Kumps, Julien Stanovici, Emmelie Chaibi, Belinda Campos-Xavier, Despina Christina Pavlidou, Christel Tran. Black cartilage: Incidentally discovered articular ochronosis during arthroplasty. Journal of inherited metabolic disease. 2021 11; 44(6):1503-1504. doi: 10.1002/jimd.12417. [PMID: 34264534]
  • Lakshminarayan R Ranganath, Milad Khedr, Sobhan Vinjamuri, James A Gallagher. Characterizing the alkaptonuria joint and spine phenotype and assessing the effect of homogentisic acid lowering therapy in a large cohort of 87 patients. Journal of inherited metabolic disease. 2021 05; 44(3):666-676. doi: 10.1002/jimd.12363. [PMID: 33452825]
  • Wladimir Bocca Vieira de Rezende Pinto, Igor Braga Farias, Bruno de Mattos Lombardi Badia, José Marcos Vieira de Albuquerque Filho, Roberta Ismael Lacerda Machado, Paulo Victor Sgobbi de Souza, Acary Souza Bulle Oliveira. Cervical Spondylotic Myelopathy Secondary to Ochronotic Vertebral Arthropathy. Neurology. 2021 03; 96(13):627-628. doi: 10.1212/wnl.0000000000011663. [PMID: 33568539]
  • Rajat Dhyani, Krishna Shankar, Ankita Bhatt, Shubham Jain, Ajmal Hussain, Naveen Kumar Navani. Homogentisic Acid-Based Whole-Cell Biosensor for Detection of Alkaptonuria Disease. Analytical chemistry. 2021 03; 93(10):4521-4527. doi: 10.1021/acs.analchem.0c04914. [PMID: 33655752]
  • Philip Chu, Maria C Cuellar, Sonali J Bracken, Teresa K Tarrant. A Mimic of Ankylosing Spondylitis, Ochronosis: Case Report and Review of the Literature. Current allergy and asthma reports. 2021 03; 21(3):19. doi: 10.1007/s11882-021-01002-1. [PMID: 33666743]
  • Maria Lucia Schiavone, Lia Millucci, Giulia Bernardini, Daniela Giustarini, Ranieri Rossi, Barbara Marzocchi, Annalisa Santucci. Homogentisic acid affects human osteoblastic functionality by oxidative stress and alteration of the Wnt/β-catenin signaling pathway. Journal of cellular physiology. 2020 10; 235(10):6808-6816. doi: 10.1002/jcp.29575. [PMID: 31989660]
  • Lakshminarayan R Ranganath, Eftychia Eirini Psarelli, Jean-Baptiste Arnoux, Daniela Braconi, Michael Briggs, Anders Bröijersén, Nadia Loftus, Helen Bygott, Trevor F Cox, Andrew S Davison, Jane P Dillon, Michael Fisher, Richard FitzGerald, Federica Genovese, Helena Glasova, Anthony K Hall, Andrew T Hughes, Juliette H Hughes, Richard Imrich, Jonathan C Jarvis, Milad Khedr, Dinny Laan, Kim-Hanh Le Quan Sang, Emily Luangrath, Ol'ga Lukáčová, Anna M Milan, Alpesh Mistry, Vanda Mlynáriková, Brendan P Norman, Birgitta Olsson, Nicholas P Rhodes, Jozef Rovenský, Mattias Rudebeck, Annalisa Santucci, Ella Shweihdi, Ciarán Scott, Jana Sedláková, Nicolas Sireau, Roman Stančík, Johan Szamosi, Sophie Taylor, Christa van Kan, Sobhan Vinjamuri, Eva Vrtíková, Chris Webb, Elizabeth West, Elizabeth Záňová, Andrea Zatkova, James A Gallagher. Efficacy and safety of once-daily nitisinone for patients with alkaptonuria (SONIA 2): an international, multicentre, open-label, randomised controlled trial. The lancet. Diabetes & endocrinology. 2020 09; 8(9):762-772. doi: 10.1016/s2213-8587(20)30228-x. [PMID: 32822600]
  • Takuho Kishi, Akira Kotani, Tomonari Umemura, Hideki Hakamata. HPLC with electrochemical detection for determining homogentisic acid and its application to urine from rats fed tyrosine-enriched food. Journal of pharmaceutical and biomedical analysis. 2020 Jul; 186(?):113253. doi: 10.1016/j.jpba.2020.113253. [PMID: 32305737]
  • Lakshminarayan R Ranganath, Anna M Milan, Andrew T Hughes, Milad Khedr, Andrew S Davison, Ella Shweihdi, Brendan P Norman, Juliette H Hughes, Helen Bygott, Emily Luangrath, Richard Fitzgerald, Eftychia E Psarelli, Christa van Kan, Dinny Laan, Birgitta Olsson, Mattias Rudebeck, Louise Mankowitz, Nicolas Sireau, Jean-Baptiste Arnoux, Kim-Hanh Le Quan Sang, Jonathan C Jarvis, Federica Genovese, Daniela Braconi, Annalisa Santucci, Andrea Zatkova, Helena Glasova, Roman Stančík, Richard Imrich, Nicholas P Rhodes, James A Gallagher. Homogentisic acid is not only eliminated by glomerular filtration and tubular secretion but also produced in the kidney in alkaptonuria. Journal of inherited metabolic disease. 2020 07; 43(4):737-747. doi: 10.1002/jimd.12181. [PMID: 31609457]
  • Shirisha Avadhanula, Wendy J Introne, Sungyoung Auh, Steven J Soldin, Brian Stolze, Debra Regier, Carla Ciccone, Fady Hannah-Shmouni, Armando C Filie, Kenneth D Burman, Joanna Klubo-Gwiezdzinska. Assessment of Thyroid Function in Patients With Alkaptonuria. JAMA network open. 2020 03; 3(3):e201357. doi: 10.1001/jamanetworkopen.2020.1357. [PMID: 32202644]
  • Sho Hosokawa, Kenichi Shukuya, Keisuke Sogabe, Yasukazu Ejima, Tatsuya Morinishi, Eiichiro Hirakawa, Hiroyuki Ohsaki, Tatsuo Shimosawa, Yasunori Tokuhara. Novel absorbance peak of gentisic acid following the oxidation reaction. PloS one. 2020; 15(4):e0232263. doi: 10.1371/journal.pone.0232263. [PMID: 32348369]
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  • Minviluz G Stacey, Rebecca E Cahoon, Hanh T Nguyen, Yaya Cui, Shirley Sato, Cuong T Nguyen, Nongnat Phoka, Kerry M Clark, Yan Liang, Joe Forrester, Josef Batek, Phat Tien Do, David A Sleper, Thomas E Clemente, Edgar B Cahoon, Gary Stacey. Identification of Homogentisate Dioxygenase as a Target for Vitamin E Biofortification in Oilseeds. Plant physiology. 2016 11; 172(3):1506-1518. doi: 10.1104/pp.16.00941. [PMID: 27660165]
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  • Marcella Laschi, Giulia Bernardini, Elena Dreassi, Lia Millucci, Michela Geminiani, Daniela Braconi, Barbara Marzocchi, Maurizio Botta, Fabrizio Manetti, Annalisa Santucci. Inhibition of para-Hydroxyphenylpyruvate Dioxygenase by Analogues of the Herbicide Nitisinone As a Strategy to Decrease Homogentisic Acid Levels, the Causative Agent of Alkaptonuria. ChemMedChem. 2016 Apr; 11(7):674-8. doi: 10.1002/cmdc.201500578. [PMID: 26947423]
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