5,6-dihydroxyindole-2-carboxylic acid (BioDeep_00001868723)

Main id: BioDeep_00000005430

 

natural product


代谢物信息卡片


5,6-Dihydroxy-1H-indole-2-carboxylic acid

化学式: C9H7NO4 (193.0375)
中文名称: 5,6-二羟基吲哚-2-羧酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=C2C=C(NC2=CC(=C1O)O)C(=O)O
InChI: InChI=1S/C9H7NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h1-3,10-12H,(H,13,14)

描述信息

A dihydroxyindole that is indole-2-carboxylic acid substituted by hydroxy groups at positions 5 and 6.

同义名列表

2 个代谢物同义名

5,6-dihydroxyindole-2-carboxylic acid; 5,6-Dihydroxy-1H-indole-2-carboxylic acid



数据库引用编号

11 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

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)

9 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 BCL2, CAT, DDT, HPGDS, IVL, LORICRIN, MIF, MITF, PTGS2, TYR, TYRP1
Peripheral membrane protein 3 ERVW-1, HSD17B6, PTGS2
Endosome membrane 1 TYRP1
Endoplasmic reticulum membrane 3 BCL2, PMEL, PTGS2
Nucleus 3 BCL2, FLG, MITF
cytosol 10 BCL2, CAT, COMT, DCT, FLG, HPGDS, IVL, LORICRIN, MIF, MITF
dendrite 1 COMT
nuclear body 1 IVL
centrosome 1 IVL
nucleoplasm 4 HPGDS, LORICRIN, MIF, MITF
Cell membrane 3 COMT, GPR35, TNF
Cytoplasmic granule 1 FLG
Early endosome membrane 1 HSD17B6
Multi-pass membrane protein 1 GPR35
Synapse 1 COMT
cell surface 2 MIF, TNF
glutamatergic synapse 1 FLG
Golgi apparatus 1 PMEL
lysosomal membrane 1 MITF
neuronal cell body 1 TNF
postsynapse 1 FLG
Lysosome 1 TYR
plasma membrane 8 COMT, DCT, ERVW-1, FLG, GPR35, MIF, PMEL, TNF
Membrane 6 BCL2, CAT, COMT, DCT, FLG, PMEL
axon 1 COMT
caveola 1 PTGS2
extracellular exosome 6 CAT, COMT, DDT, IVL, MIF, PMEL
Lysosome membrane 1 MITF
Lumenal side 1 HSD17B6
endoplasmic reticulum 4 BCL2, HSD17B6, PMEL, PTGS2
extracellular space 3 DDT, MIF, TNF
perinuclear region of cytoplasm 1 TYR
mitochondrion 2 BCL2, CAT
protein-containing complex 4 BCL2, CAT, MITF, PTGS2
intracellular membrane-bounded organelle 6 CAT, COMT, DCT, HPGDS, HSD17B6, TYR
Microsome membrane 2 HSD17B6, PTGS2
Single-pass type I membrane protein 5 DCT, ERVW-1, PMEL, TYR, TYRP1
Secreted 2 MIF, PMEL
extracellular region 4 CAT, FLG, MIF, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
mitochondrial matrix 1 CAT
Extracellular side 1 COMT
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 1 TNF
Endosome, multivesicular body 1 PMEL
Extracellular vesicle 1 PMEL
cytoplasmic vesicle 1 FLG
Melanosome membrane 4 DCT, PMEL, TYR, TYRP1
Golgi-associated vesicle 1 TYR
recycling endosome 1 TNF
Single-pass type II membrane protein 2 COMT, TNF
vesicle 1 MIF
Membrane raft 1 TNF
pore complex 1 BCL2
focal adhesion 1 CAT
Peroxisome 1 CAT
intracellular vesicle 1 TYRP1
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 1 FLG
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
receptor complex 1 FLG
neuron projection 1 PTGS2
chromatin 1 MITF
phagocytic cup 1 TNF
cytoplasmic ribonucleoprotein granule 1 FLG
Cornified envelope 3 FLG, IVL, LORICRIN
Melanosome 4 DCT, PMEL, TYR, TYRP1
myelin sheath 1 BCL2
multivesicular body membrane 1 PMEL
ficolin-1-rich granule lumen 2 CAT, MIF
secretory granule lumen 2 CAT, MIF
endoplasmic reticulum lumen 1 PTGS2
Golgi apparatus, cis-Golgi network membrane 1 PMEL
clathrin-coated endocytic vesicle membrane 1 TYRP1
[Transmembrane protein]: Cell membrane 1 ERVW-1
[Surface protein]: Cell membrane 1 ERVW-1
cis-Golgi network membrane 1 PMEL
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
multivesicular body, internal vesicle 1 PMEL
catalase complex 1 CAT
keratohyalin granule 1 FLG
BAD-BCL-2 complex 1 BCL2
[Isoform Soluble]: Cytoplasm 1 COMT
[Isoform Membrane-bound]: Cell membrane 1 COMT
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
[Syncytin-1]: Virion 1 ERVW-1


文献列表

  • Marcela Valko-Rokytovská, Beáta Hubková, Anna Birková, Jana Mašlanková, Marek Stupák, Marianna Zábavníková, Beáta Čižmárová, Mária Mareková. Specific Urinary Metabolites in Malignant Melanoma. Medicina (Kaunas, Lithuania). 2019 May; 55(5):. doi: 10.3390/medicina55050145. [PMID: 31100919]
  • Raffaella Micillo, Mariagrazia Iacomino, Marco Perfetti, Lucia Panzella, Kenzo Koike, Gerardino D'Errico, Marco d'Ischia, Alessandra Napolitano. Unexpected impact of esterification on the antioxidant activity and (photo)stability of a eumelanin from 5,6-dihydroxyindole-2-carboxylic acid. Pigment cell & melanoma research. 2018 07; 31(4):475-483. doi: 10.1111/pcmr.12689. [PMID: 29350885]
  • S K Shanuja, S Iswarya, A Gnanamani. Marine fungal DHICA as a UVB protectant: Assessment under in vitro and in vivo conditions. Journal of photochemistry and photobiology. B, Biology. 2018 Feb; 179(?):139-148. doi: 10.1016/j.jphotobiol.2018.01.010. [PMID: 29367149]
  • Takeo Iwata, Hisaaki Taniguchi, Masamichi Kuwajima, Takako Taniguchi, Yuko Okuda, Akiko Sukeno, Kyoko Ishimoto, Noriko Mizusawa, Katsuhiko Yoshimoto. The action of D-dopachrome tautomerase as an adipokine in adipocyte lipid metabolism. PloS one. 2012; 7(3):e33402. doi: 10.1371/journal.pone.0033402. [PMID: 22428043]
  • Lucia Panzella, Alessandra Napolitano, Marco d'Ischia. Is DHICA the key to dopachrome tautomerase and melanocyte functions?. Pigment cell & melanoma research. 2011 Feb; 24(1):248-9. doi: 10.1111/j.1755-148x.2010.00771.x. [PMID: 20846176]
  • Colleen M Trantow, Adam Hedberg-Buenz, Sachiyo Iwashita, Steven A Moore, Michael G Anderson. Elevated oxidative membrane damage associated with genetic modifiers of Lyst-mutant phenotypes. PLoS genetics. 2010 Jul; 6(7):e1001008. doi: 10.1371/journal.pgen.1001008. [PMID: 20617205]
  • A Khemis, A Kaiafa, C Queille-Roussel, L Duteil, J P Ortonne. Evaluation of efficacy and safety of rucinol serum in patients with melasma: a randomized controlled trial. The British journal of dermatology. 2007 May; 156(5):997-1004. doi: 10.1111/j.1365-2133.2007.07814.x. [PMID: 17388924]
  • Tomohisa Hirobe, Kazumasa Wakamatsu, Shosuke Ito. Changes in the proliferation and differentiation of neonatal mouse pink-eyed dilution melanocytes in the presence of excess tyrosine. Pigment cell research. 2003 Dec; 16(6):619-28. doi: 10.1046/j.1600-0749.2003.00091.x. [PMID: 14629719]
  • Tomohisa Hirobe, Kazumasa Wakamatsu, Shosuke Ito, Hiroyuki Abe, Yoko Kawa, Masako Mizoguchi. Stimulation of the proliferation and differentiation of mouse pink-eyed dilution epidermal melanocytes by excess tyrosine in serum-free primary culture. Journal of cellular physiology. 2002 May; 191(2):162-72. doi: 10.1002/jcp.10085. [PMID: 12064459]
  • C Kipp, A R Young. The soluble eumelanin precursor 5,6-dihydroxyindole-2-carboxylic acid enhances oxidative damage in human keratinocyte DNA after UVA irradiation. Photochemistry and photobiology. 1999 Aug; 70(2):191-8. doi: . [PMID: 10461458]
  • S Memoli, A Napolitano, M d'Ischia, G Misuraca, A Palumbo, G Prota. Diffusible melanin-related metabolites are potent inhibitors of lipid peroxidation. Biochimica et biophysica acta. 1997 May; 1346(1):61-8. doi: 10.1016/s0005-2760(97)00018-0. [PMID: 9187303]
  • T Horikoshi, S Ito, K Wakamatsu, H Onodera, H Eguchi. Evaluation of melanin-related metabolites as markers of melanoma progression. Cancer. 1994 Feb; 73(3):629-36. doi: 10.1002/1097-0142(19940201)73:3<629::aid-cncr2820730321>3.0.co;2-w. [PMID: 8299084]
  • A Kammeyer, L A Oomen, S Pavel. Preparation of monoclonal mouse antibodies against two specific eu-melanin related compounds. Journal of immunological methods. 1992 Nov; 156(1):61-7. doi: 10.1016/0022-1759(92)90011-h. [PMID: 1431163]
  • K Yamada, N Walsh, H Hara, K Jimbow, H Chen, S Ito. Measurement of eumelanin precursor metabolites in the urine as a new marker for melanoma metastases. Archives of dermatology. 1992 Apr; 128(4):491-4. doi: . [PMID: 1580656]
  • 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]
  • K Wakamatsu, S Ito. Preparation of eumelanin-related metabolites 5,6-dihydroxyindole, 5,6-dihydroxyindole-2-carboxylic acid, and their O-methyl derivatives. Analytical biochemistry. 1988 May; 170(2):335-40. doi: 10.1016/0003-2697(88)90639-2. [PMID: 3394933]
  • C Hansson. Some indolic compounds as markers of the melanocyte activity. Acta dermato-venereologica. Supplementum. 1988; 138(?):1-60. doi: . [PMID: 3176811]
  • C Hansson. A quantitative method for determination of 5,6-dihydroxyindole-2-carboxylic acid using high-pressure liquid chromatography with fluorometric detection. Analytical biochemistry. 1983 Jun; 131(2):379-84. doi: 10.1016/0003-2697(83)90187-2. [PMID: 6614473]
  • C Hansson. Demonstration of 5,6-dihydroxyindole-2-carboxylic acid, a melanin precursor, in normal urine. Acta dermato-venereologica. 1983; 63(2):147-9. doi: NULL. [PMID: 6189330]
  • S Pavel, F A Muskiet, G T Nagel, J Duchon. [Identification of some indolic acids in urine using mass fragmentography (author's transl)]. Sbornik lekarsky. 1981 May; 83(5):121-7. doi: NULL. [PMID: 7256174]