L-Dopachrome (BioDeep_00000004741)

 

Secondary id: BioDeep_00001869227

human metabolite Endogenous natural product


代谢物信息卡片


(2S)-2,3,5,6-Tetrahydro-5,6-dioxo-1H-indole-2-carboxylic acid

化学式: C9H7NO4 (193.0375)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 24.16%

分子结构信息

SMILES: C1C(NC2=CC(=O)C(=O)C=C21)C(=O)O
InChI: InChI=1S/C9H7NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h2-3,6,10H,1H2,(H,13,14)

描述信息

Dopachrome is a cyclization product of L-DOPA and is an intermediate in the biosynthesis of melanin. Dopaquinone has an ortho-quinone ring, which is known to be neurotoxic and highly reactive with many other compounds (PMID: 413870). Dopachrome spontaneously gives rise to 5,6-dihydroxyindole (DHI) or it can be enzymatically metabolized by dopachrome tautomerase to give 5,6-dihydroxyindole-2-carboxylic acid (DHICA). DHI and its oxidation products are also toxic to cells. Many Parkinsons patients are treated with L-DOPA. However, long-term treatment with L-DOPA may actually worsen symptoms or may 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).
The non-decarboxylative tautomerization of L-dopachrome to 5,6-dihydroxyindole-2-carboxylic acid in the melanin biosynthetic pathway is catalyzed by Tyrosinase-related protein-2, a melanocyte-specific enzyme. (PMID 11095412) [HMDB]

同义名列表

6 个代谢物同义名

(2S)-2,3,5,6-Tetrahydro-5,6-dioxo-1H-indole-2-carboxylic acid; (2S)-5,6-Dioxo-2,3,5,6-tetrahydro-1H-indole-2-carboxylic acid; (2S)-5,6-dioxo-2,4,5,6-tetrahydro-1H-indole-2-carboxylic acid; 2-L-Carboxy-2,3-dihydroindole-5,6-quinone; L-Dopachrome; Dopachrome



数据库引用编号

20 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

63 个相关的代谢反应过程信息。

Reactome(36)

BioCyc(0)

WikiPathways(2)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(25)

PharmGKB(0)

11 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 15 ANXA5, CAT, DCTN4, DDC, DDT, DHCR24, ELANE, MIF, MITF, NQO1, TH, TLR7, TLR9, TYR, TYRP1
Peripheral membrane protein 2 ANXA5, HSD17B6
Endosome membrane 3 TLR7, TLR9, TYRP1
Endoplasmic reticulum membrane 4 DHCR24, MLANA, TLR7, TLR9
Nucleus 5 DCTN4, DHCR24, MITF, NQO1, TH
cytosol 9 ANXA5, CAT, DCTN4, DDC, ELANE, MIF, MITF, NQO1, TH
dendrite 2 NQO1, TH
phagocytic vesicle 2 ELANE, TLR9
trans-Golgi network 1 MLANA
centrosome 1 DCTN4
nucleoplasm 3 MIF, MITF, MNT
Cell projection, axon 1 TH
Early endosome membrane 2 HSD17B6, TLR9
Golgi apparatus membrane 2 DHCR24, TLR9
Synapse 1 NQO1
cell cortex 1 DCTN4
cell surface 2 ELANE, MIF
Golgi apparatus 1 MLANA
Golgi membrane 3 DHCR24, TLR7, TLR9
lysosomal membrane 2 CP, MITF
neuronal cell body 1 NQO1
sarcolemma 1 ANXA5
smooth endoplasmic reticulum 1 TH
synaptic vesicle 1 TH
Cytoplasm, cytosol 1 NQO1
Lysosome 3 TLR7, TLR9, TYR
endosome 2 TLR7, TLR9
plasma membrane 5 CP, MIF, MLANA, TLR7, TLR9
terminal bouton 1 TH
Membrane 6 ANXA5, CAT, DHCR24, NQO1, TLR7, TLR9
apical plasma membrane 1 TLR9
axon 1 TH
basolateral plasma membrane 1 TLR9
extracellular exosome 7 ANXA5, CAT, CP, DDC, DDT, ELANE, MIF
Lysosome membrane 1 MITF
Lumenal side 1 HSD17B6
endoplasmic reticulum 4 DHCR24, HSD17B6, TLR7, TLR9
extracellular space 5 CP, CXCL8, DDT, ELANE, MIF
perinuclear region of cytoplasm 2 TH, TYR
mitochondrion 2 CAT, TH
protein-containing complex 2 CAT, MITF
intracellular membrane-bounded organelle 3 CAT, HSD17B6, TYR
Microsome membrane 1 HSD17B6
Single-pass type I membrane protein 4 TLR7, TLR9, TYR, TYRP1
Secreted 3 CP, CXCL8, MIF
extracellular region 7 ANXA5, CAT, CP, CXCL8, ELANE, MIF, TLR9
cytoplasmic side of plasma membrane 1 TH
Single-pass membrane protein 1 DHCR24
mitochondrial matrix 1 CAT
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 DCTN4
external side of plasma membrane 1 ANXA5
perikaryon 1 TH
cytoplasmic vesicle 1 TH
Melanosome membrane 4 MLANA, TH, TYR, TYRP1
Golgi-associated vesicle 1 TYR
vesicle 1 MIF
Cytoplasm, perinuclear region 1 TH
Cytoplasm, cytoskeleton 1 DCTN4
focal adhesion 3 ANXA5, CAT, DCTN4
Peroxisome 1 CAT
intracellular vesicle 1 TYRP1
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 2 ANXA5, ELANE
secretory granule 1 ELANE
Cytoplasm, myofibril, sarcomere 1 DCTN4
sarcomere 1 DCTN4
receptor complex 1 TLR7
Zymogen granule membrane 1 ANXA5
neuron projection 1 TH
chromatin 2 MITF, MNT
spindle pole 1 DCTN4
Cytoplasm, cell cortex 1 DCTN4
blood microparticle 1 CP
Endomembrane system 1 TLR7
Melanosome 3 MLANA, TYR, TYRP1
stress fiber 1 DCTN4
ficolin-1-rich granule lumen 2 CAT, MIF
secretory granule lumen 2 CAT, MIF
endoplasmic reticulum lumen 1 CP
transcription repressor complex 1 ELANE
specific granule lumen 1 ELANE
dynactin complex 1 DCTN4
kinetochore 1 DCTN4
azurophil granule lumen 1 ELANE
cytoplasmic dynein complex 1 DCTN4
vesicle membrane 1 ANXA5
clathrin-coated endocytic vesicle membrane 1 TYRP1
Cytoplasm, cytoskeleton, stress fiber 1 DCTN4
endolysosome membrane 2 TLR7, TLR9
early phagosome 2 TLR7, TLR9
Cytoplasmic vesicle, phagosome 3 ELANE, TLR7, TLR9
catalase complex 1 CAT
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle 1 TH
endothelial microparticle 1 ANXA5
endolysosome 1 TLR9


文献列表

  • A Cherqui, B Duvic, C Reibel, M Brehélin. Cooperation of dopachrome conversion factor with phenoloxidase in the eumelanin pathway in haemolymph of Locusta migratoria (Insecta). Insect biochemistry and molecular biology. 1998 Nov; 28(11):839-48. doi: 10.1016/s0965-1748(98)00076-9. [PMID: 9818385]
  • H Matsuda, M Higashino, Y Nakai, M Iinuma, M Kubo, F A Lang. Studies of cuticle drugs from natural sources. IV. Inhibitory effects of some Arctostaphylos plants on melanin biosynthesis. Biological & pharmaceutical bulletin. 1996 Jan; 19(1):153-6. doi: 10.1248/bpb.19.153. [PMID: 8820931]
  • H Matsuda, S Nakamura, M Kubo. Studies of cuticle drugs from natural sources. II. Inhibitory effects of Prunus plants on melanin biosynthesis. Biological & pharmaceutical bulletin. 1994 Oct; 17(10):1417-20. doi: 10.1248/bpb.17.1417. [PMID: 7874069]
  • G Odh, A Hindemith, A M Rosengren, E Rosengren, H Rorsman. Isolation of a new tautomerase monitored by the conversion of D-dopachrome to 5,6-dihydroxyindole. Biochemical and biophysical research communications. 1993 Dec; 197(2):619-24. doi: 10.1006/bbrc.1993.2524. [PMID: 8267597]
  • M Miranda, C di Ilio, A Bonfigli, A Arcadi, G Pitari, S Dupre, G Federici, G del Boccio. A study on the in vitro interaction between tyrosinase and glutathione S-transferase. Biochimica et biophysica acta. 1987 Jul; 913(3):386-94. doi: 10.1016/0167-4838(87)90150-6. [PMID: 3109490]