Dopaquinone (BioDeep_00000004487)

 

Secondary id: BioDeep_00000897502, BioDeep_00001869513, BioDeep_00001872407

human metabolite Endogenous natural product


代谢物信息卡片


(2S)-2-amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid

化学式: C9H9NO4 (195.0532)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(feces) 34.4%

分子结构信息

SMILES: C1=CC(=O)C(=O)C=C1CC(C(=O)O)N
InChI: InChI=1S/C9H9NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6H,3,10H2,(H,13,14)

描述信息

Dopaquinone, also known as o-dopaquinone or L-dopaquinone, is a member of the class of compounds known as L-alpha-amino acids. L-alpha-amino acids are alpha-amino acids which have the L-configuration of the alpha-carbon atom. Dopaquinone is slightly soluble (in water) and a moderately acidic compound (based on its pKa). L-Dopaquinone is a metabolite of L-DOPA and a precursor of melanin. Melanin is synthesized from tyrosine by hydroxylation to dihydroxyphenylalanine (DOPA) and subsequent oxidation to dopaquinone. Both reactions are catalyzed by the enzyme tyrosinase, which is the rate-limiting step. Dopaquinone has an ortho-quinone ring, which is known to be neurotoxic and highly reactive with many other compounds (PMID: 413870). Dopaquinone typically combines with cysteine to form pheomelanin (a pigment-polymer). Alternatively, dopaquinone can be converted to leucodopachrome and eventually to eumelanin (also a pigment-polymer). Dopaquinone can be found in skin and feces. Within the cell, dopaquinone is primarily located in the cytoplasm. Dopaquinone is involved in several metabolic disorders, some of which include transient tyrosinemia, hawkinsinuria, tyrosinemia type I, and alkaptonuria. Chronically high levels of dopaquinone are associated with Parkinsons disease (PD). Many Parkinsons patients are treated with L-DOPA. However, long-term treatment with L-DOPA may actually worsen symptoms or result in neurotic and psychotic symptoms. These may be due to dopachrome and dopaquinone accumulating in the brain of L-DOPA treated patients (PMID: 19131041, PMID: 12373519).
Dopaquinone is a substrate of enzyme monophenol monooxygenase [EC 1.14.18.1] in tyrosine metabolism pathway (KEGG). [HMDB]

同义名列表

9 个代谢物同义名

(2S)-2-amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid; (S)-2-Amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid; (S)-2-Amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoate; 4-(2-Carboxy-2-aminoethyl)-1,2-benzoquinone; Dopaquinone, (S)-isomer; L-dopaquinone; O-Dopaquinone; Dopaquinone; Dopaquinone



数据库引用编号

21 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(2)

BioCyc(0)

PlantCyc(0)

代谢反应

60 个相关的代谢反应过程信息。

Reactome(33)

BioCyc(0)

WikiPathways(3)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(24)

PharmGKB(0)

14 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 ANXA5, APOB, CAT, DDC, FASN, MITF, SMO, SNCA, TH, TYR, TYRP1
Peripheral membrane protein 1 ANXA5
Endosome membrane 2 APOB, TYRP1
Endoplasmic reticulum membrane 1 APOB
Nucleus 4 MITF, SMO, SNCA, TH
cytosol 13 ANXA5, APOB, CAT, DCT, DDC, FASN, GCLM, GSR, MITF, PAH, SMO, SNCA, TH
dendrite 2 SMO, TH
nucleoplasm 3 MITF, MNT, SMO
Cell membrane 1 SMO
Cell projection, axon 2 SNCA, TH
Multi-pass membrane protein 1 SMO
Synapse 1 SNCA
cell cortex 1 SNCA
cell surface 1 APOH
Golgi apparatus 2 FASN, SMO
Golgi membrane 1 INS
growth cone 1 SNCA
lysosomal membrane 1 MITF
neuronal cell body 2 APOB, SNCA
postsynapse 1 SNCA
sarcolemma 1 ANXA5
smooth endoplasmic reticulum 2 APOB, TH
synaptic vesicle 1 TH
Lysosome 2 SNCA, TYR
plasma membrane 5 APOB, DCT, FASN, SMO, SNCA
synaptic vesicle membrane 1 SNCA
terminal bouton 1 TH
Membrane 5 ANXA5, CAT, DCT, FASN, SNCA
axon 2 SNCA, TH
extracellular exosome 10 ANXA5, APOB, APOH, CAT, DDC, FASN, GPX3, GSR, SERPINF1, SMO
Lysosome membrane 1 MITF
endoplasmic reticulum 1 SMO
extracellular space 6 APOB, APOH, GPX3, INS, SERPINF1, SNCA
lysosomal lumen 1 APOB
perinuclear region of cytoplasm 4 SERPINF1, SNCA, TH, TYR
mitochondrion 4 CAT, GSR, SNCA, TH
protein-containing complex 3 CAT, MITF, SNCA
intracellular membrane-bounded organelle 5 APOB, CAT, DCT, SMO, TYR
Single-pass type I membrane protein 3 DCT, TYR, TYRP1
Secreted 6 APOB, APOH, GPX3, INS, SERPINF1, SNCA
extracellular region 8 ANXA5, APOB, APOH, CAT, GPX3, INS, SERPINF1, SNCA
cytoplasmic side of plasma membrane 1 TH
mitochondrial matrix 2 CAT, GSR
Cell projection, cilium 1 SMO
ciliary membrane 1 SMO
nuclear membrane 1 SMO
external side of plasma membrane 2 ANXA5, GSR
chylomicron 2 APOB, APOH
high-density lipoprotein particle 1 APOH
low-density lipoprotein particle 1 APOB
very-low-density lipoprotein particle 2 APOB, APOH
actin cytoskeleton 1 SNCA
perikaryon 1 TH
cytoplasmic vesicle 1 TH
Melanosome membrane 4 DCT, TH, TYR, TYRP1
Early endosome 1 APOB
Golgi-associated vesicle 1 TYR
Cytoplasm, perinuclear region 1 TH
focal adhesion 2 ANXA5, CAT
Peroxisome 1 CAT
basement membrane 1 SERPINF1
intracellular vesicle 1 TYRP1
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 3 ANXA5, APOH, SERPINF1
ciliary tip 1 SMO
Late endosome 1 SMO
Zymogen granule membrane 1 ANXA5
neuron projection 1 TH
cilium 1 SMO
chromatin 2 MITF, MNT
supramolecular fiber 1 SNCA
centriole 1 SMO
endosome lumen 2 APOB, INS
Lipid droplet 1 APOB
Melanosome 5 DCT, FASN, SERPINF1, TYR, TYRP1
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 2 CAT, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 APOB, INS
axon terminus 1 SNCA
endocytic vesicle membrane 1 SMO
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
endoplasmic reticulum exit site 1 APOB
9+0 non-motile cilium 1 SMO
vesicle membrane 1 ANXA5
clathrin-coated endocytic vesicle membrane 2 APOB, TYRP1
axon hillock 1 SERPINF1
endoplasmic reticulum-Golgi intermediate compartment 1 SMO
endocytic vesicle lumen 1 APOB
chylomicron remnant 1 APOB
intermediate-density lipoprotein particle 1 APOB
platelet dense granule lumen 1 APOH
catalase complex 1 CAT
mature chylomicron 1 APOB
inclusion body 1 SNCA
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle 1 TH
endothelial microparticle 1 ANXA5
glutamate-cysteine ligase complex 1 GCLM
glycogen granule 1 FASN


文献列表

  • Yehyang Kim, Sohun Lee, Ji Hye Ryu, Kee Dong Yoon, Song Seok Shin. Effect of Aurea Helianthus stem extract on anti-melanogenesis. Bioscience, biotechnology, and biochemistry. 2018 Nov; 82(11):1871-1879. doi: 10.1080/09168451.2018.1506311. [PMID: 30146944]
  • Beata Gasowska, Hubert Wojtasek, Józef Hurek, Marcin Drag, Kornel Nowak, Paweł Kafarski. Redox reaction between amino-(3,4-dihydroxyphenyl)methyl phosphonic acid and dopaquinone is responsible for the apparent inhibitory effect on tyrosinase. European journal of biochemistry. 2002 Aug; 269(16):4098-104. doi: 10.1046/j.1432-1033.2002.03103.x. [PMID: 12180986]
  • K Tsukamoto, M Furue, Y Sato, O Takayama, R Akasu, N Ohtake, K Wakamatsu, S Ito, K Tamaki, S Shimada. Generalized melanosis in metastatic malignant melanoma: the possible role of DOPAquinone metabolites. Dermatology (Basel, Switzerland). 1998; 197(4):338-42. doi: 10.1159/000018028. [PMID: 9873171]
  • G Prota. The role of peroxidase in melanogenesis revisited. Pigment cell research. 1992; Suppl 2(?):25-31. doi: 10.1111/j.1600-0749.1990.tb00344.x. [PMID: 1329073]